text:
|Publication number
|Publication type
|Application number
|PCT number
|Publication date
|Dec 26, 2000
|Filing date
|Feb 20, 1998
|Priority date
|Feb 26, 1997
|Fee status
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|Publication number
|David Rose, Horst Hoeffkes, Bernd Meinigke
|Original Assignee
|Henkel Kommanditgesellschaft Auf Aktien
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|BiBTeX, EndNote, RefMan
|Patent Citations (17), Non-Patent Citations (8), Referenced by (24), Classifications (25), Legal Events (5)
|External Links: USPTO, USPTO Assignment, Espacenet
This application is filed under 35 U.S.C. 371 and based on PCT/EP98/00986, filed Feb. 20, 1998.
1. Field of the Invention
This invention relates to new diazacycloheptane derivatives, to their use for coloring keratin fibers and to colorants containing these compounds.
2. Discussion of Related Art
By virtue of their intensive colors and good fastness properties, so-called oxidation colorants play a prominent role in the coloring of keratin fibers, particularly human hair. Oxidation colorants contain oxidation dye precursors, so-called primary intermediates and secondary intermediates. The primary intermediates form the actual dyes with one another or by coupling with one or more secondary intermediates in the presence of oxidizing agents or atmospheric oxygen.
Good oxidation dye precursors are expected to satisfy above all the following requirements: they must form the required color tones with sufficient intensity and fastness during the oxidative coupling reaction. In addition, they must be readily absorbed onto the fibers with no significant differences--particularly in the case of human hair--between damaged and freshly regrown hair (levelling behavior). They must be resistant to light, heat and the effect of chemical reducing agents, for example permanent wave lotions. Finally, if they are used to color hair, they should not overly stain the scalp and, above all, should be toxicologically and dermatologically safe.
The primary intermediates normally used are primary aromatic amines containing another free or substituted hydroxy or amino group in the para position or the ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof.
Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)-ethanol, (2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido-4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminohydroxy pyrimidine and 1,3-N,N'-bis-(2'-hydroxyethyl)-N,N'-bis-(4'-aminophenyl)-diamino-2-propanol.
The secondary intermediates are generally m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols. Particularly suitable secondary intermediates are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)-propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-4-hydroxypyridine, 2-methyl resorcinol and 5-methyl resorcinol.
In general, natural color tones cannot be obtained with a primary intermediate alone or with a special secondary intermediate/primary intermediate combination. In practice, therefore, combinations of various primary intermediates and secondary intermediates are used so that there is a constant need for new improved dye components.
Accordingly, the problem addressed by the present invention was to provide new primary intermediates which would satisfy the requirements oxidation dye precursors are expected to meet to a particular degree.
It has now been found that certain, hitherto unknown 1,4-diazacycloheptane derivatives satisfy the requirements primary intermediates are expected to meet to a particularly high degree. Thus, brilliant color tones, more especially in the brown and blue range, which are extremely fast to light and washing are obtained using these primary intermediates with most of the known secondary intermediates. In addition, the colors obtained are distinguished by extremely high fastness to cold waving and thermal stability and by excellent level dyeing behavior.
In a first embodiment, therefore, the present invention relates to 1,4-diazacycloheptane derivatives corresponding to general formula (I): ##STR2## R1, R2, R3 and R4 independently of one another represent hydrogen, a C1-4 alkyl or hydroxyalkyl group or a C2-4 dihydroxyalkyl group,
X and Y independently of one another represent hydrogen, chlorine, fluorine, a C1-4 alkyl, hydroxyalkyl, aminoalkyl or alkoxy group, a C2-4 dihydroxyalkyl group or an allyl group and
R5 and R6 independently of one another represent hydrogen or a C2-4 alkyl group.
These compounds can be produced by known organic synthesis methods. Particulars can be found in the following Synthesis Examples.
The outstanding suitability of these compounds as primary intermediates for oxidation colorants is also particularly surprising because the analogous piperidino compounds do not have any significant primary intermediate properties.
Since all the compounds according to the invention are amino compounds, the known acid addition salts can be prepared from them by the usual methods. Accordingly, all the disclosures of the present specification and, hence, the claimed scope of protection apply both to the 1,4-diazacycloheptane derivatives of formula (I) present in free form and to their water-soluble, physiologically compatible salts. Examples of such salts are the hydrochlorides, the hydrobromides, the sulfates, the phosphates, the acetates, the propionates, the citrates and the lactates.
The 1,4-diazacycloheptane derivatives corresponding to formula (I), in which the two substituents R5 and R6 at the 1,4-diazacycloheptane ring are hydrogens, have proved to be particularly suitable for the purposes of the invention.
Compounds corresponding to formula (I), in which at least three and, more particularly, all four of the groups R1,R2, R3 and R4 are hydrogens, are also preferred for the purposes of the invention.
Finally, those 1,4-diazacycloheptane derivatives of formula (I) in which the two substituents X and Y at the two aromatic rings independently of one another represent hydrogen, fluorine, chlorine or a C1-4 alkyl group, have also proved to be particularly suitable for the purposes of the invention. Hydrogen and methyl groups have proved to be most particularly advantageous groups X and Y.
Compounds with particularly outstanding suitability for the purposes of the invention are
N,N'-bis-(4-amino-2-methylphenyl)-1,4-diazacycloheptane and
Of these compounds, N,N'-bis-(4-aminophenyl)-1,4-diazacycloheptane and N,N'-bis-(4-amino-3-methylphenyl)-1,4-diazacycloheptane are preferred.
In a second embodiment, the present invention relates to the use of the above-mentioned 1,4-diazacycloheptane derivatives as primary intermediates in oxidation hair colorants.
Finally, in a third embodiment, the present invention relates to oxidation colorants for coloring keratin fibers containing secondary intermediates and primary intermediates in a water-containing carrier, characterized in that one of the above-mentioned 1,4-diazacycloheptane derivatives is present as the primary intermediate.
Keratin fibers in the context of the present invention include pelts, wool, feathers and, more particularly, human hair. Although the oxidation colorants according to the invention are particularly suitable for coloring keratin fibers, there is basically nothing to prevent them from being used in other fields, particularly in color photography.
The oxidation colorants according to the invention contain the primary intermediates according to the invention and, if desired, may contain other primary intermediates and secondary intermediates. So far as the other primary and secondary intermediates are concerned, reference is made to the compounds mentioned at the beginning of the present specification which represent preferred other dye components.
According to the invention, preferred primary intermediates are p-phenylenediamine, p-toluylenediamine, p-aminophenol, o-aminophenol, 1-(2'-hydroxyethyl)-2,5-diaminobenzene, N,N-bis-(2-hydroxyethyl) p-phenylenediamine, 2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido-4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2-hydroxyethylaminomethyl-4-aminophenol, 4,4'-diaminodiphenylamine, 4-amino-3-fluorophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, bis-(2-hydroxy-5-aminophenyl)-methane, 1,4-bis-(4-aminophenyl)-diazacycloheptane, 1,3-bis-(N-(2-hydroxyethyl)-N-(4-aminophenylamino))-2-propanol, 4-amino-2-(2-hydroxyethoxy)-phenol and 4,5-diaminopyrazole derivatives according to EP 0 740 741 or WO 94/08970 such as, for example, 4,5-diamino-1-(2'-hydroxyethyl)-pyrazole.
Most particularly preferred other primary intermediates are 2,4,5,6-tetraminopyrimidine, 1-(240 -hydroxyethyl)-2,5-diaminobenzene, 3-methyl-4-aminophenol, o-aminophenol, 2-aminomethyl- and 2-hydroxymethyl-4-aminophenol.
According to the invention, preferred secondary intermediates are 1-naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, o-aminophenol, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)-propane, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methyl resorcinol, 5-methyl resorcinol, 2,5-dimethyl resorcinol, 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2-amino-3-hydroxypyridine, 2,6-dihydroxy3,4-diaminopyridine, 3-amino-2-methylamino-6-methoxypyridine, 4-amino-2-hydroxytoluene, 2,6-bis-(2-hydroxyethylamino)-toluene, 2,4-diaminophenoxyethanol, 1-methoxy-2-amino-4-(2-hydroxyethylamino)-benzene, 2-methyl-4-chloro-5-aminophenol, 6-methyl-1,2,3,4-tetrahydroquinoxaline, 3,4-methylenedioxyphenol, 3,4-methylenedioxyaniline, 2,6-dimethyl-3-aminophenol, 3-amino-6-methoxy-2-methylaminophenol, 2-hydroxy-4-aminophenoxyethanol, 2-methyl-5-(2-hydroxyethylamino)-phenol and 2,6-dihydroxy-3,4-dimethyl pyridine.
Particularly preferred secondary intermediates are 1-naphthol, resorcinol, 1,3-bis-(2,4-diaminophenoxy)-propane, 2-hydroxy-4-aminophenoxyethanol, 4-chlororesorcinol, 2,4-diaminophenoxyethanol, 2-methyl resorcinol, 2-methyl-5-(2-hydroxyethylamino)-phenol, 3-amino-2-methylamino-6-methoxypyridine.
These other primary and secondary intermediates are normally used in free form. Where they contain amino groups, however, it may be preferable to use them in salt form, particularly in the form of the hydrochlorides and sulfates.
The hair colorants according to the invention contain both the primary intermediates and the secondary intermediates in a quantity of preferably 0.005 to 20% by weight and more preferably 0.1 to 5% by weight, based on the oxidation colorant as a whole. The primary intermediates and secondary intermediates are generally used in a substantially equimolar ratio to one another. Although it has proved to be of advantage to use the primary and secondary intermediates in an equimolar ratio, there is no disadvantage in using individual oxidation dye precursors in a certain excess so that primary intermediates and secondary intermediates may be present in a molar ratio of 1:0.5 to 1:3 and, more particularly, 1:1 to 1:2.
Substantive dyes are normally nitrophenylendiamines, nitroaminophenols, aza dyes, anthraquinones or indophenols. Preferred substantive dyes are the compounds known under the International names or trade names of HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 and also 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitrotoluidine, picramic acid, 2-amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-1-hydroxy-4-nitrobenzene. The colorants according to the invention of this embodiment preferably contain the substantive dyes in a quantity of 0.01 to 20% by weight, based on the colorant as a whole.
The colorants according to the invention may also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, camomile blossom, sandalwood, black tea, black alder bark, sage, logwood, madder root, catechu, sedre and alkanet.
Other dye components which may be present in the colorants according to the invention are indols and indolines and physiologically compatible salts thereof. Preferred examples are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 6-hydroxyindole, 6-aminoindole and 4-aminoindole. Also preferred are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
The oxidation dye precursors or the substantive dyes optionally present do not have to be single compounds. On the contrary, other components may be present in small quantities in the hair colorants according to the invention due to the processes used to produce the individual dyes providing these other components do not adversely affect the coloring result or have to be ruled out for other reasons, for example toxicological reasons.
So far as the dyes suitable for use in the hair colorants and tinting formulations according to the invention are concerned, reference is also expressly made to the work by Ch. Zviak, The Science of Hair Care, Chapter 7 (pages 248-250; substantive dyes) and Chapter 8, pages 264-267; oxidation dye precursors), published as Volume 7 of the Series "Dermatology" (Ed.: Ch. Culnan and H. Maibach), Marcel Dekker Inc., New York/Basle, 1986, and to the "Europaische Inventar der Kosmetik-Rohstoffe" published by the Europaische Gemeinschaft and available in disk form from the Bundesverband Deutscher Industrie- und Handelsunternehmen fur Arzneimittel, Reformwaren und Korperpflegemittel d.V., Mannheim.
To produce the colorants according to the invention, the oxidation dye precursors are incorporated in a suitable water-containing carrier. For coloring hair, such carriers are, for example, creams, emulsions, gels or even surfactant-containing foaming solutions, for example shampoos, foam aerosols or other formulations suitable for application to the hair.
The colorants according to the invention may also contain any of the known active substances, additives and auxiliaries typical of such formulations. In many cases, the colorants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many cases, however, it has been found to be of advantage to select the surfactants from anionic, zwitterionic or nonionic surfactants.
Suitable anionic surfactants for the hair colorants according to the invention are any anionic surface-active substances suitable for use on the human body. Such substances are characterized by a water-solubilizing anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group containing around 10 to 22 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide and hydroxyl groups may also be present in the molecule. The following are examples of suitable anionic surfactants--in the form of the sodium, potassium and ammonium salts and the mono-, di- and trialkanol-ammonium salts containing 2 or 3 carbon atoms in the alkanol group:
linear fatty acids containing 10 to 22 carbon atoms (soaps),
ether carboxylic acids corresponding to the formula R--O--(CH2 --CH2 O)x --CH2 --COOH, in which R is a linear alkyl group containing 10 to 22 carbon atoms and x=0 or 1 to 16,
acyl sarcosides containing 10 to 18 carbon atoms in the acyl group,
acyl taurides containing 10 to 18 carbon atoms in the acyl group,
acyl isethionates containing 10 to 18 carbon atoms in the acyl group,
sulfosuccinic acid mono- and dialkyl esters containing 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl esters containing 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups,
linear alkane sulfonates containing 12 to 18 carbon atoms,
linear α-olefin sulfonates containing 12 to 18 carbon atoms,
α-sulfofatty acid methyl esters of fatty acids containing 12 to 18 carbon atoms,
alkyl sulfates and alkyl polyglycol ether sulfates corresponding to the formula R--O(CH2 --CH2 O)x --SO3 H, in which R is a preferably linear alkyl group containing 10 to 18 carbon atoms and x=0 or 1 to 12,
mixtures of surface-active hydroxysulfonates according to DE-A-37 25 030,
sulfated hydroxyalkyl polyethylene and/or hydroxyalkylene propylene glycol ethers according to DE-A-37 23 354,
sulfonates of unsaturated fatty acids containing 12 to 24 carbon atoms and 1 to 6 double bonds according to DE-A-39 26 344,
esters of tartaric acid and citric acid with alcohols in the form of addition products of around 2 to 15 molecules of ethylene oxide and/or propylene oxide with fatty alcohols containing 8 to 22 carbon atoms.
Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids containing 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule and, in particular, salts of saturated and, more particularly, unsaturated C8-22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
In the context of the invention, zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one --COO.sup.(-) or --SO3.sup.(-) group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. A preferred zwitterionic surfactant is the fatty acid amide derivative known by the CTFA name of Cocamidopropyl Betaine.
Ampholytic surfactants are surface-active compounds which, in addition to a C8-18 alkyl or acyl group, contain at least one free amino group and at least one --COOH or --SO3 H group in the molecule and which are capable of forming inner salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl aminobutyric acids, N-alkyl iminodipropionic acids, N-hydroxyethyl-N-alkyl amidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkyl aminopropionic acids and alkyl aminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkyl aminopropionate, cocoacyl aminoethyl aminopropionate and C12-18 acyl sarcosine.
Nonionic surfactants contain, for example, a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups as the hydrophilic group. Examples of such compounds are
products of the addition of 2 to 30 moles of ethylene oxide and/or 0 to 5 moles of propylene oxide onto linear fatty alcohols containing 8 to 22 carbon atoms, onto fatty acids containing 12 to 22 carbon atoms and onto alkylphenols containing 8 to 15 carbon atoms in the alkyl group,
C12-22 fatty acid monoesters and diesters of products of the addition of 1 to 30 moles of ethylene oxide onto glycerol,
C8-22 alkyl mono- and oligoglycosides and ethoxylated analogs thereof,
products of the addition of 5 to 60 moles of ethylene oxide onto castor oil and hydrogenated castor oil,
products of the addition of ethylene oxide onto sorbitan fatty acid esters,
products of the addition of ethylene oxide onto fatty acid alkanolamides.
Examples of cationic surfactants suitable for use in the hair treatment formulations according to the invention are, in particular, quaternary ammonium compounds. Preferred quaternary ammonium compounds are ammonium halides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethyl ammonium chlorides and trialkyl methyl ammonium chlorides, for example cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride. Other cationic surfactants suitable for use in accordance with the invention are the quaternized protein hydrolyzates.
Also suitable for use in accordance with the invention are cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethyl silyl amodimethicone), Dow Coming 929 Emulsion (containing a hydroxylamino-modified silicone which is also known as Amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil�-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethyl siloxanes, Quaternium-80).
Alkyl amidoamines, particularly fatty acid amidoamines, such as the stearyl amidopropyl dimethyl amine obtainable as Tego Amid�S 18, are distinguished not only by their favorable conditioning effect, but also and in particular by their ready biodegradability.
Quaternary ester compounds, so-called "esterquats", such as the methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the trade name of Stepantex�, are also readily biodegradable.
One example of a quaternary sugar derivative suitable for use as a cationic surfactant is the commercially available product Glucquat�100 (CTFA name: Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride).
The compounds containing alkyl groups used as surfactants may be single compounds. In general, however, these compounds are produced from native vegetable or animal raw materials so that mixtures with different alkyl chain lengths dependent upon the particular raw material are obtained.
The surfactants representing addition products of ethylene and/or propylene oxide with fatty alcohols or derivatives of these addition products may be both products with a "normal" homolog distribution and products with a narrow homolog distribution. Products with a "normal" homolog distribution are mixtures of homologs which are obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts. By contrast, narrow homolog distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be of advantage.
Other active substances, auxiliaries and additives are, for example,
nonionic polymers such as, for example, vinyl pyrrolidone/vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone/vinyl acetate copolymers and polysiloxanes,
cationic polymers, such as quaternized cellulose ethers, polysiloxanes containing quaternary groups, dimethyl diallyl ammonium chloride polymers, acrylamide/dimethyl diallyl ammonium chloride copolymers, dimethyl aminoethyl methacrylate/vinyl pyrrolidone copolymers quaternized with diethyl sulfate, vinyl pyrrolidone/imidazolinium methochloride copolymers and quaternized polyvinyl alcohol,
zwitterionic and amphoteric polymers such as, for example, acrylamidopropyl/trimethyl ammonium chloride/acrylate copolymers and octyl acrylamide/methyl methacrylate/tert.butyl aminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers,
anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate/crotonic acid copolymers, vinyl pyrrolidone/ vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinyl ether/maleic anhydride copolymers and acrylic acid/ethyl acrylate/N-tert.butyl acrylamide terpolymers,
thickeners, such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, carob bean flour, linseed gums, dextrans, cellulose derivatives, for example methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives, such as amylose, amylopectin and dextrins, clays such as, for example, bentonite or fully synthetic hydrocolloids such as, for example, polyvinyl alcohol,
structurants, such as glucose and maleic acid,
hair-conditioning compounds, such as phospholipids, for example soya lecithin, egg lecithin and kephalins, and also silicone oils,
protein hydrolyzates, more particularly elastin, collagen, keratin, milk protein, soya protein and wheat protein hydrolyzates, condensation products thereof with fatty acids and quaternized protein hydrolyzates,
perfume oils, dimethyl isosorbide and cyclodextrins,
solubilizers, such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
antidandruff agents, such as Piroctone Olamine and Zinc Omadine,
other substances for adjusting the pH value,
active substances, such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and salts thereof, plant extracts and vitamins,
UV absorbers,
consistency providers, such as sugar esters, polyol esters or polyol alkyl ethers,
fats and waxes, such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
fatty acid alkanolamides,
complexing agents, such as EDTA, NTA and phosphonic acids,
swelling and penetration agents, such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
opacifiers, such as latex,
pearlescers, such as ethylene glycol mono- and distearate,
propellents, such as propane/butane mixtures, N2 O, dimethyl ether, CO2 and air and
To produce the colorants according to the invention, the constituents of the water-containing carrier are used in the usual quantities for this purpose. For example, emulsifiers are used in concentrations of 0.5 to 30% by weight while thickeners are used in concentrations of 0.1 to 25% by weight, based on the colorant as a whole.
In principle, the color can be oxidatively developed with atmospheric oxygen. However, a chemical oxidizing agent is preferably used, particularly when human hair is to be not only colored, but also lightened. Particularly suitable oxidizing agents are persulfates, chlorites and, in particular, hydrogen peroxide or addition products thereof with urea, melamine or sodium borate. Oxidation may also be carried out with enzymes. In this case, the enzymes may be used to transfer atmospheric oxygen to the primary intermediate or to enhance the effect of an oxidizing agent present in small quantities. One example of an enzymatic process is the procedure whereby the effect of small quantities (for example 1% and less, based on the formulation as a whole) of hydrogen peroxide is enhanced by peroxidases.
The preparation of the oxidizing agent is preferably mixed with the preparation of the oxidation dye precursors immediately before coloring of the hair. The ready-to-use hair coloring preparation formed should preferably have a pH value in the range from 6 to 10. In a particularly preferred embodiment, the hair colorant is used in a mildly alkaline medium. The application temperatures may be in the range from 15 to 40� C. After a contact time of about 5 to 30 minutes, the hair colorant is removed from the hair to be colored by rinsing. There is no need for the hair to be washed with a shampoo where a carrier of high surfactant content, for example a coloring shampoo, has been used.
The following Examples are intended to illustrate the invention.
1st Stage: N,N'-bis-(4-nitrophenyl)-1,4-diazacycloheptane
A mixture of 22 g of 1,4-diazacycloheptane, 28.2 g of p-fluoronitrobenzene and 300 ml of ethanol was heated for 6 hours to 150� C. in an autoclave. After cooling, the solid precipitated was filtered off under suction. The product accumulated in the form of yellow crystals with a melting point of >310� C.
2nd Stage: N,N'-bis-(4-aminophenyl)-1,4-diazacycloheptane-4 HCI
14.8 g of the product from stage 1 were suspended in 300 ml of a 1:1 mixture of ethanol and water. The resulting suspension was then hydrogenated under a hydrogen pressure of 20 atm and at a temperature of 50� C. using a conventional catalyst (palladium on carbon) until no more hydrogen was taken up. After cooling, the catalyst was filtered off and the solution was acidified with dilute hydrochloric acid and concentrated by evaporation to dryness. The product accumulated in the form of light violet crystals with a melting point of 196� C. (decomp.).
1st Stage: N,N'-bis-(4-nitro-2-methylphenyl)-1,4-diazacycloheptane
A mixture of 7.9 g of 1,4-diazacycloheptane, 24.1 g of 2-fluoro-5-nitrotoluene and 300 ml of ethanol was heated for 6 hours to 150� C. in an autoclave. After cooling, the solid precipitated was filtered off under suction. The product accumulated in the form of yellow crystals with a melting point of 154� C.
2nd Stage: N,N'-bis-(4-amino-2-methylphenyl)-1,4-diazacycloheptane-4 HCI
3.5 g of the product from stage 1 was suspended in 400 ml of ethanol. The resulting suspension was then hydrogenated under a hydrogen pressure of 5 atm and at a temperature of 50� C. using a conventional catalyst (palladium on carbon) until no more hydrogen was taken up. After cooling, the catalyst was filtered off, the solution was acidified with dilute hydrochloric acid and concentrated by evaporation to dryness. The product accumulated in the form of colorless crystals melting at around 220� C. (decomp.).
1st Stage: N,N'-bis-(4-nitro-3-methylphenyl)-1,4-diazacycloheptane
A mixture of 16.6 g of 1,4-diazacycloheptane, 52 g of 5-fluoro-2-nitrotoluene and 300 ml of ethanol was heated for 6 hours to 150� C. in an autoclave. After cooling, the solid precipitated was filtered off under suction. The product accumulated in the form of yellow crystals with a melting point of 214� C.
2nd Stage: N,N'-bis-(4-amino-3-methylphenyl)-1,4-diazacycloheptane-4 HCI
3.5 g of the product from stage 1 were suspended in 400 ml of ethanol. The resulting suspension was then hydrogenated under a hydrogen pressure of 5 atm and at a temperature of 50� C. using a conventional catalyst (palladium on carbon) until no more hydrogen was taken up. After cooling, the catalyst was filtered off and the solution was acidified with dilute hydrochloric acid and concentrated by evaporation to dryness. The product accumulated in the form of beige-colored crystals with a melting point of 182� C. (decomp.).
2. Coloring
A cream base with the following composition was first prepared [all quantities are in g, unless otherwise indicated]:
______________________________________tallow fatty alcohol 17.0Lorol � techn.1 4.0Texapon � N 282 40.0Dehyton � K3 25.0Eumulgin � B 24 1.5distilled water 12.5______________________________________ 1 C12-18 fatty alcohol (HENKEL) 2 Sodium lauryl ether sulfate (ca. 28% active substance; CTFA name: Sodium Laureth Sulfate) (HENKEL) 3 Fatty acid amide derivative with a betaine structure corresponding to the following formula: R--CONH(CH2)3 N+ (CH3).sub. CH2 COO- (ca. 30% active substance; CTFA name Cocoamidopropyl Betaine) (HENKEL) 4 Cetyl stearyl alcohol containing ca. 20 moles EO (CTFA name: Ceteareth20) (HENKEL)
The following hair coloring cream emulsion was then prepared on the basis of this cream:
______________________________________cream base 50.0primary intermediate 7.5 mmoles*secondary intermediate 7.5 mmoles*Na2 SO3 (inhibitor) 1.0(NH4)2 SO4 1.0conc. ammonia solution to pH 10water to 100______________________________________ *unless otherwise indicated
The ingredients were mixed in the order listed. After addition of the oxidation dye precursors and the inhibitor, the emulsion was first adjusted to pH 10 with concentrated ammonia solution and was then made up with water to 100 g.
The color was oxidatively developed with 3% hydrogen peroxide solution as the oxidizing solution. To this end, 50 g of hydrogen peroxide solution (3%) were added to and mixed with 100 g of the emulsion.
The coloring cream was applied to approximately 5 cm long tresses of standardized, 90% grey but not specially pretreated human hair and left thereon for 30 minutes at 32� C. On completion of the coloring process, the hair was rinsed, washed with a normal shampoo and dried. The following primary and secondary intermediates were used for coloring:
Primary intermediates
N,N'-bis-(4-aminophenyl)-1,4-diazacycloheptane (P1)
N,N'-bis-(4-aminophenyl)-piperidine (P2)--Comparison Example--
N,N'-bis-(4-amino-2-methylphenyl)-1,4-diazacycloheptane (P3)
N,N'-bis-(4-amino-3-methylphenyl)-1,4-diazacycloheptane (P4)
2,4,5,6-tetraaminopyrimidine (P5)
4-amino-3-methylphenol (P6)
2-aminomethyl-4-aminophenol (P7)
p-aminophenol (P8)
1-(2-hydroxyethyl)-2,5-diaminobenzene (P9)
4-hydroxy-2,5,6-triaminopyrimidine (P10)
N,N-bis-(2-hydroxyethyl)-p-phenylenediamine (P11)
p-toluylenediamine (P12)
2-(2,5-diaminophenoxy)-ethanol (P13).
Secondary intermediates
1-naphthol (S1)
rescorcinol (S2)
2-methyl-5-aminophenol (S3)
1,3-bis-(2,4-diaminophenoxy)-propane (S4)
2-chloro-6-methyl-3-aminophenol (S5)
3-amino-6-methoxy-2-methylaminophenol (S6)
2-hydroxy-4-aminophenoxyethanol (S7)
2-amino-3-hydroxypyridine (S8)
4-chlororesorcinol (S9)
2,4-diaminophenoxyethanol (S10)
2,6-dimethyl-3-aminophenol (S11)
2,4-dichloro-3-aminophenol (S12)
3,4-methylenedioxyphenol (S13)
2-methyl resorcinol (S14)
m-aminophenol (S15)
2-methyl-5-(2-hydroxyethylamino)-phenol (S16)
2,6-dihydroxy-3,4-dimethyl pyridine (S17)
3-amino-2-methylamino-6-methoxypyridine (S18)
1-methoxy-2-amino-4-(2-hydroxyethylamino)-benzene (S19)
2,6-bis-(2-hydroxyethylamino)-toluene (S20)
1,7-dihydroxynaphthalene (S21)
2,7-dihydroxynaphthalene (S22)
The following colors were obtained:
______________________________________Primary Secondaryintermediate intermediate Hair color Intensity______________________________________P1 S1 Azure blue Very intensiveP2 S1 Grey-magenta Very weakP1 S2 Dark brown IntensiveP2 S2 Dark blond WeakP1 S3 Dark violet IntensiveP2 S3 Red-brown Very weakP1 S4 Black-blue Very intensiveP2 S4 Dark violet Very weakP1 S5 Dark violet Very intensiveP2 S5 Violet Very weakP1 S7 Dark violet IntensiveP1 S8 Dark violet IntensiveP1 S9 Grey-brown IntensiveP1 S10 Black-blue IntensiveP1 S11 Deep violet IntensiveP1 S12 Black-blue IntensiveP1 S13 Grey-brown IntensiveP1 S14 Dark brown IntensiveP1 S15 Black-blue IntensiveP1 S16 Dark violet IntensiveP1 S17 Grey-blue IntensiveP1 S18 Dark green IntensiveP1 S19 Black-blue IntensiveP3 S1 Flat red IntensiveP3 S5 Grey-red IntensiveP4 S4 Dark blue IntensiveP4 S5 Black-blue IntensiveP4 S6 Dark turquoise IntensiveP1 + P5a S4 + S14a Dark blue IntensiveP1 + P6a S8 Red-brown IntensiveP1 + P7a S3 Photobrown IntensiveP1 + P8a S3 Photobrown IntensiveP1 + P9a S3 Dark violet IntensiveP1 + P10a S20 Black-blue IntensiveP1 + P11a S2 + S15a Blue-grey IntensiveP1 + P8a S4 + S9a Navy blue IntensiveP1 + P10a S11 + S21a Dark violet IntensiveP1 + P12a S18 + S22a Nordic blue IntensiveP1 + P6a + P13a S3b Dark ruby Intensive______________________________________ a 0.375 mmole b 0.113 mmole
|Cited Patent
|Filing date
|Publication date
|Jul 29, 1987
|May 24, 1988
|Henkel Kommanditgesellschaft Auf Aktien
|New tetra-aminopyrimidine derivatives and their use in hair-dyeing preparations
|Jul 29, 1988
|Sep 12, 1989
|Henkel Kommanditgesellschaft Auf Aktien
|Surface-active hydroxysulfonates
|Jul 13, 1988
|Jun 5, 1990
|Henkel Kommanditgesellschaft Auf Aktien
|Sulfated hydroxy mixed ethers, a process for their production, and their use
|Jul 31, 1990
|Mar 15, 1994
|Henkel Kommanditgesellschaft Auf Aktien
|Process for the preparation of light-colored oleic acid sulfonates
|Jun 23, 1992
|Sep 6, 1994
|Oxidation dye composition containing at least one double base in combination with at least one single base and dyeing process making use of it
|Sep 29, 1993
|Jul 9, 1996
|Wella Aktiengesellschaft
|Composition for the oxidative dyeing of hair containing 4,5-diaminopyrazole derivatives as well as new 4,5-diaminopyrazole derivatives and process for their synthesis
|Jul 15, 1987
|Jan 26, 1989
|Henkel Kgaa
|Sulfatierte hydroxy-mischether, verfahren zu ihrer herstellung und ihre verwendung
|Jul 29, 1987
|Feb 9, 1989
|Henkel Kgaa
|Oberflaechenaktive hydroxysulfonate
|Aug 9, 1989
|Feb 28, 1991
|Henkel Kgaa
|Verfahren zur herstellung von hellfarbigen oelsaeuresulfonaten
|Aug 2, 1979
|Mar 17, 1982
|Henkel Kommanditgesellschaft auf Aktien
|Bis-aminopyridines, their preparation and use as oxidative hair dye components, and hair dyestuffs containing them
|Aug 10, 1987
|Feb 24, 1988
|Henkel Kommanditgesellschaft auf Aktien
|Tetraaminopyrimidine derivatives and their use as hair dyeing agents
|Aug 30, 1989
|Mar 28, 1990
|Oxidation dyeing composition containing at least one double and at least one single dyeing base, and dyeing process making use of such a composition
|Jan 3, 1995
|Nov 6, 1996
|Siemens Electric Limited
|Canister purge system having improved purge valve
|Title not available
|Mar 5, 1991
|Sep 19, 1991
|Henkel Kommanditgesellschaft Auf Aktien
|Paraphenylenediamine derivatives and their use in oxidative dyes
|Sep 29, 1993
|Apr 28, 1994
|Wella Aktiengesellschaft
|Oxidation hair dye containing 4,5-diaminopyrazole derivatives and novel 4,5-diaminopyrazole derivatives and process for their production
|Jul 2, 1997
|Jan 15, 1998
|Hans Schwarzkopf Gmbh & Co. Kg
|New piperazine derivatives and oxydation dyes
|CAPLUS Abstract of JP 1 61449, Terumo Corp., Mar. 1989.
|CAPLUS Abstract of JP 1-61449, Terumo Corp., Mar. 1989.
|Dermatology, 8 pp. 263 287.
|Dermatology, 8 pp. 263-287.
|Europaeische Inventar der Kosmetic Rohstoffe, Dittmar et al.
|Europaeische Inventar der Kosmetic-Rohstoffe, Dittmar et al.
|The Science of Hair Care, vol. 7, Chapter 7 pp. 248 250.
|The Science of Hair Care, vol. 7, Chapter 7 pp. 248-250.
|Citing Patent
|Filing date
|Publication date
|Jun 23, 1999
|Mar 25, 2003
|Henkel Kommanditgesellschaft Auf Aktien
|Sep 9, 2003
|Aug 2, 2005
|L'oreal S.A.
|Bis-para-phenylenediamine derivatives comprising a pyrrolidyl group and use of these derivatives for dyeing keratin fibres
|Mar 27, 2003
|Sep 20, 2005
|L'oreal S.A.
|Pyrrolidinyl-substituted para-phenylenediamine derivatives substituted with a cationic radical, and use of these derivatives for dyeing keratin fibers
|Jul 7, 2003
|Nov 7, 2006
|Para-phenylenediamine derivatives containing a pyrrolidyl group, and use of these derivatives for coloring keratin fibers
|Mar 13, 2001
|Feb 20, 2007
|L'oreal S.A.
|Dyeing compositions for keratinous fibers containing paraphenylenediamine derivatives with pyrrolidinyl group
|Mar 24, 2004
|Mar 6, 2007
|L'oreal Sa
|Composition for dyeing keratin fibres, comprising a cationic para-phenylenediamine derivative substituted with a diazacyclohexane or diazacycloheptane ring
|Aug 7, 2002
|Jul 10, 2007
|L'oreal, S.A.
|Composition for dyeing keratin fibers comprising at least one para-phenylenediamine substituted with a diazacycloheptane radical
|Jul 31, 2007
|Jul 13, 2010
|Kao Corporation
|Hair dye composition
|Mar 13, 2001
|May 22, 2003
|Laurent Vidal
|Dyeing compositions for keratinous fibres containing paraphenylenediamine derivatives with pyrrolidinyl group
|Mar 5, 2001
|Aug 28, 2003
|Gerard Lang
|Oxidation dyeing composition for keratinous fibres with a particular paraphenylene-diamine derivative and a particular direct dyeing agent
|Mar 5, 2001
|Sep 11, 2003
|Gerard Lang
|Oxidation dyeing composition for keratinous fibres and dyeing method using same
|Nov 12, 2001
|Apr 22, 2004
|Eric Terranova
|Oxidation dyeing composition based on 1-(4-aminophenyl) pyrrolidines substituted in positions 3 and 4, and dyeing method using same
|Jul 7, 2003
|Apr 22, 2004
|Stephane Sabelle
|Para-phenylenediamine derivatives containing a pyrrolidyl group, and use of these derivatives for coloring keratin fibers
|Nov 13, 2001
|May 6, 2004
|Stephane Sabelle
|Dyeing composition based on 1-(4-aminophenyl)pyrrolidines substituted at least in positions 2 and 3
|Nov 13, 2001
|May 13, 2004
|Stephane Sabelle
|Oxidation dyeing composition based on 1-(4-aminophenyl) pyrrolidines substituted in position 2
|Apr 2, 2002
|May 20, 2004
|Laurent Vidal
|Dyeing composition for dyeing kerationou fibres comprising a cationic azo-dye
|Sep 9, 2003
|Jul 1, 2004
|Stephane Sabelle
|Bis-para-phenylenediamine derivatives comprising a pyrrolidyl group and use of these derivatives for dyeing keratin fibres
|Mar 4, 2004
|Oct 7, 2004
|Georg Knuebel
|Bridged p-phenylenediamines
|Mar 24, 2004
|Dec 2, 2004
|Alain Genet
|Composition for dyeing keratin fibres, comprising a cationic para-phenylenediamine derivative substituted with a diazacyclohexane or diazacycloheptane ring
|Aug 7, 2002
|May 19, 2005
|Stephane Sabelle
|Composition for dyeing keratinous fibers containing a paraphenylenediamine substituted by a diazacycloheptane radical
|Sep 24, 2004
|Jun 9, 2005
|Laurent Vidal
|Triazacyclononane derivatives substituted on at least one of the nitrogen atoms with a substituted or unsubstituted 4'-aminophenyl group, for dyeing keratin fibres
|Jul 31, 2007
|Jan 7, 2010
|Kao Corporation
|Hair dye composition
|Mar 16, 2004
|Sep 29, 2004
|Composition for dyeing of keratinic fibers comprising a cationic derivative of p-phenylenediamine substituted by a diazacyclohexane or a diazacyloheptane
|Sep 23, 2004
|Mar 30, 2005
|Triazacyclononane derivatives substituted on at least one of the nitrogene atoms by a 4-aminophenyle group for dyeing keratinic fibres
|U.S. Classification
|8/409, 540/611, 540/612, 8/416, 540/609, 8/407, 540/575, 8/423
|International Classification
|Cooperative Classification
|European Classification
|Aug 25, 1999
Owner name: HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN (HENKEL KG
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ROSE, DAVID;HOEFFKES, HORST;MEINIGKE, BERND;REEL/FRAME:010326/0913
Effective date: 19990726
|Jun 14, 2004
|Fee payment
Year of fee payment: 4
|Jul 7, 2008
|Maintenance fee reminder mailed
|Dec 26, 2008
|Lapse for failure to pay maintenance fees
|Feb 17, 2009
|Expired due to failure to pay maintenance fee
Effective date: 20081226


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Last update: Monday 27 June 2016 [763 news items]
Digitimes Research: More software developers join Android camp
Mar 20, 16:03
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China handset makers hope to reduce reliance on Android
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MWC 2013: Nokia launches four new mobile phones
Newswatch - Feb 26, 14:47
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Feb 26, 11:58
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Feb 21, 10:50
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Feb 20, 19:03
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Jan 17, 20:39
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- Perforce Powers Development of Legacy Quest for iOS and Android
30-Jun-2016 markets closed
|TSE electronic
|OTC electronic
- After Brexit vote, yuan falls to weakest point against dollar since 2010 (Jun 27) - Wall Street Journal
- US extends ZTE reprieve for alleged Iran sanctions violations (Jun 27) - Reuters
- Many companies plan to impose Brexit hiring freeze (Jun 27) - BBC News
- Taiwan's largest airline cancels flights as staff set to strike (Jun 23) - Reuters
- Brexit: UK votes to leave EU in historic referendum (Jun 24) - BBC News
- Why you should care about the Brexit vote (Jun 21) - CNNMoney
- Tesla makes offer to acquire SolarCity (Jun 21) - Company release
- Ericsson faces US corruption probe: Swedish newspaper (Jun 16) - Reuters
- Digitimes Research: 4 million 9.7-inch iPad Pros to ship in 1H16
- Digitimes Research: Global all-in-one PC shipments to drop 3.9% on year in 2015
- Mentor Graphics Veloce VirtuaLAB adds protocols for networking designs
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- Digitimes Research: iPad Pro shipments to be less than 3 million units in 4Q15
Industry integration, 5G and IoT applications: Q&A with Qualcomm president Derek Aberle
Qualcomm president Derek Aberle spared his time with Digitimes for an exclusive interview...
The gaming notebook competition: Q&A with Jone Chang from Gigabyte notebook department
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Taiwan-based companies have a long and successful history of involvement in the supply chain for mobile devices, which for the purposes of this article consist...
- Taiwan motherboard industry overview - May 2012
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- Notebook market overview - Jun 2011
The notebook industry in 2010 experienced several major events that significantly changed the industry's ecosystem for the year and the industry is also believed...
- LCD TV overview - Jun 2011
Growth of the global LCD TV market was not as strong as expected in 2010 as the market continued to feel the aftershocks of the economic recession that had hit...
- Wireless broadband developments in Southeast Asia markets
As of 2013, the 10 ASEAN nations had a total of over 700 million mobile subscriptions, with the CAGR from 2003-2013 reaching 24%. This Digitimes Research Special Report analyzes the various mobile broadband markets in ASEAN and looks at the respective trends in 4G LTE development for those markets.
- 2015 global tablet demand forecast
This Digitimes Research Special Report provides a 2015 forecast for the global tablet market and analyzes the strategies of key market players such as Google, Apple, Intel, and Microsoft.
- 2015 China smartphone panel trend forecast
This Digitimes Research Special Report analyzes the strategies of key China-based major panel makers BOE, Tianma and IVO for attacking the different market segments through technology and pricing, and their relationship to local vendors Huawei, Lenovo, ZTE, Xiaomi and Coolpad.


text:
*Ending months of speculation, Cissy Houston has officially announced she is penning a book about her late superstar daughter, Whitney Houston.
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The Houston family matriarch signed a deal with HarperCollins, which promises the "unabridged and unbelievable story" of the talented and troubled singer, whose once-soaring career stumbled while she grappled with drug addiction and a rocky marriage to Bobby Brown.
"When I lost my daughter Nippy (Whitney Houston's nickname), the world lost one of the most beautiful voices and an extraordinarily beautiful and charitable woman," Cissy Houston said Monday in a statement via The Associated Press.
"In sharing our story in this book, I hope to give her fans something to treasure, the way we all treasured Whitney. We are still receiving thousands of letters each day from her fans, and I hope reading this book will provide a deeper understanding into my daughter's true story," continued Houston.
The book will be published in February 2013; financial terms weren't disclosed.
In April, reports emerged that she had been pitching the book idea to publishers, promising a true tale of Houston's life.
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|By Business Wire
Article Rating:
|November 20, 2012 09:42 AM EST
Datadog, an innovator in the IT monitoring space, today announced a $6.2M A-round of funding, co-led by Index Ventures and RTP Ventures, an affiliate of ru-Net Holdings, with participation from existing investors IA Ventures, Amplify Partners, Contour Ventures and NYCSeed. With the new funding, Datadog intends to expand its development, sales and marketing operations to serve its rapidly growing enterprise customer base.
Unlike traditional monitoring products, Datadog focuses on presenting an integrated view of the tools and services used by IT teams across development and operations, and delivering the right insights to the relevant team members. In addition to its out-of-the-box capabilities, Datadog is built to aggregate data from other applications, cloud providers and specialized management tools, covering the full lifecycle from code change to deployment to monitoring alert with a consistent data model and experience from end-to-end.
"IT teams are deluged with data from an ever larger number of tools, creating as many data silos that prevent them from understanding and resolving issues," said Olivier Pomel, CEO of Datadog. "We founded Datadog to make it easy and affordable for enterprises to tame this complexity, embrace faster release cycles, and marry legacy and next-generation architectures while avoiding split brains between Development and Operations."
"Datadog gives us visibility into our performance metrics, alerts and incidents, no matter the origin. As a result Dev and Ops teams have an easier time being on the same page, and at the end of the day, we see fewer issues and solve them faster," said Sabry Tozin, SVP Engineering at IGN, a Datadog enterprise customer.
"Our success is based on the simple premise that we built a tool practitioners want to use. It takes 5 minutes to set up, servers, clouds and apps appear automatically, and the product is as friendly as the best consumer sites," added Alexis Le-Quoc, CTO, Datadog.
"Olivier, Alexis and the Datadog team have identified a significant opportunity within increasingly complex IT environments and built an elegant and easy to deploy product for Devops. We're excited to welcome them to the Index family," said Shardul Shah, Index Ventures.
"We see Datadog setting the standard for infrastructure monitoring in the cloud age: they aggregate tens of billions of records a day from dozens of sources for their largest customers, yet present it in a simple interactive package," said Murat Bicer, Managing Director at RTP Ventures. "We are thrilled to be partnering with them."
About Index Ventures
Index Ventures is a leading global venture capital firm active in technology and biotechnology investing since 1996. From our offices in Geneva, London and San Francisco we love to discover and support the most entrepreneurial teams wherever they are looking to build market defining global businesses. For more information on our investments, from seed through to growth stage, please visit http://www.indexventures.com
About RTP Ventures
Ru-net Technology Partners (RTP), an affiliate of ru-Net Holdings, is an early stage venture capital firm. Investing globally out of offices in New York, Boston and Moscow, we support entrepreneurs building innovative technologies with a focus on cloud computing, software as a service, and enterprise infrastructure. For more information, please visit our website at http://www.rtp.vc.
About Datadog
Datadog is a service for IT, operations and development teams who write and run applications at scale, and want to turn the massive amounts of data produced by their apps, tools and services into actionable insight. Datadog is a privately-held, venture-funded company based in New York City. To tame the complexity of your systems, maximize velocity, availability and performance, and avoid split-brains between dev and ops, try it at http://datadoghq.com You'll be up and running in 5 minutes.
"There's a growing demand from users for things to be faster. When you think about all the transactions or interactions users will have with your product and everything that is between those transactions and interactions - what drives us at Catchpoint Systems is the idea to measure that and to analyze it," explained Leo Vasiliou, Director of Web Performance Engineering at Catchpoint Systems, in this SYS-CON.tv interview at 18th Cloud Expo, held June 7-9, 2016, at the Javits Center in New York Ci...
Jul. 1, 2016 12:32 PM EDT
Apixio Inc. has raised $19.3 million in Series D venture capital funding led by SSM Partners with participation from First Analysis, Bain Capital Ventures and Apixio's largest angel investor. Apixio will dedicate the proceeds toward advancing and scaling products powered by its cognitive computing platform, further enabling insights for optimal patient care. The Series D funding comes as Apixio experiences strong momentum and increasing demand for its HCC Profiler solution, which mines unstruc...
Jul. 1, 2016 12:30 PM EDT Reads: 651
SYS-CON Events has announced today that Roger Strukhoff has been named conference chair of Cloud Expo and @ThingsExpo 2016 Silicon Valley. The 19th Cloud Expo and 6th @ThingsExpo will take place on November 1-3, 2016, at the Santa Clara Convention Center in Santa Clara, CA. "The Internet of Things brings trillions of dollars of opportunity to developers and enterprise IT, no matter how you measure it," stated Roger Strukhoff. "More importantly, it leverages the power of devices and the Interne...
Jul. 1, 2016 12:00 PM EDT Reads: 623
In addition to all the benefits, IoT is also bringing new kind of customer experience challenges - cars that unlock themselves, thermostats turning houses into saunas and baby video monitors broadcasting over the internet. This list can only increase because while IoT services should be intuitive and simple to use, the delivery ecosystem is a myriad of potential problems as IoT explodes complexity. So finding a performance issue is like finding the proverbial needle in the haystack.
Jul. 1, 2016 10:45 AM EDT Reads: 540
Machine Learning helps make complex systems more efficient. By applying advanced Machine Learning techniques such as Cognitive Fingerprinting, wind project operators can utilize these tools to learn from collected data, detect regular patterns, and optimize their own operations. In his session at 18th Cloud Expo, Stuart Gillen, Director of Business Development at SparkCognition, discussed how research has demonstrated the value of Machine Learning in delivering next generation analytics to imp...
Jul. 1, 2016 10:30 AM EDT Reads: 1,062
Whether your IoT service is connecting cars, homes, appliances, wearable, cameras or other devices, one question hangs in the balance – how do you actually make money from this service? The ability to turn your IoT service into profit requires the ability to create a monetization strategy that is flexible, scalable and working for you in real-time. It must be a transparent, smoothly implemented strategy that all stakeholders – from customers to the board – will be able to understand and comprehe...
Jul. 1, 2016 10:00 AM EDT Reads: 482
Extracting business value from Internet of Things (IoT) data doesn't happen overnight. There are several requirements that must be satisfied, including IoT device enablement, data analysis, real-time detection of complex events and automated orchestration of actions. Unfortunately, too many companies fall short in achieving their business goals by implementing incomplete solutions or not focusing on tangible use cases. In his general session at @ThingsExpo, Dave McCarthy, Director of Products...
Jul. 1, 2016 09:49 AM EDT Reads: 220
The cloud market growth today is largely in public clouds. While there is a lot of spend in IT departments in virtualization, these aren't yet translating into a true "cloud" experience within the enterprise. What is stopping the growth of the "private cloud" market? In his general session at 18th Cloud Expo, Nara Rajagopalan, CEO of Accelerite, explored the challenges in deploying, managing, and getting adoption for a private cloud within an enterprise. What are the key differences between wh...
Jul. 1, 2016 09:30 AM EDT Reads: 1,167
Ask someone to architect an Internet of Things (IoT) solution and you are guaranteed to see a reference to the cloud. This would lead you to believe that IoT requires the cloud to exist. However, there are many IoT use cases where the cloud is not feasible or desirable. In his session at @ThingsExpo, Dave McCarthy, Director of Products at Bsquare Corporation, will discuss the strategies that exist to extend intelligence directly to IoT devices and sensors, freeing them from the constraints of ...
Jul. 1, 2016 09:12 AM EDT Reads: 221
The IoT is changing the way enterprises conduct business. In his session at @ThingsExpo, Eric Hoffman, Vice President at EastBanc Technologies, discussed how businesses can gain an edge over competitors by empowering consumers to take control through IoT. He cited examples such as a Washington, D.C.-based sports club that leveraged IoT and the cloud to develop a comprehensive booking system. He also highlighted how IoT can revitalize and restore outdated business models, making them profitable ...
Jul. 1, 2016 09:00 AM EDT Reads: 662
IoT offers a value of almost $4 trillion to the manufacturing industry through platforms that can improve margins, optimize operations & drive high performance work teams. By using IoT technologies as a foundation, manufacturing customers are integrating worker safety with manufacturing systems, driving deep collaboration and utilizing analytics to exponentially increased per-unit margins. However, as Benoit Lheureux, the VP for Research at Gartner points out, "IoT project implementers often ...
Jul. 1, 2016 08:45 AM EDT Reads: 777
When people aren't talking about VMs and containers, they're talking about serverless architecture. Serverless is about no maintenance. It means you are not worried about low-level infrastructural and operational details. An event-driven serverless platform is a great use case for IoT. In his session at @ThingsExpo, Animesh Singh, an STSM and Lead for IBM Cloud Platform and Infrastructure, will detail how to build a distributed serverless, polyglot, microservices framework using open source tec...
Jul. 1, 2016 08:30 AM EDT Reads: 774
The idea of comparing data in motion (at the sensor level) to data at rest (in a Big Data server warehouse) with predictive analytics in the cloud is very appealing to the industrial IoT sector. The problem Big Data vendors have, however, is access to that data in motion at the sensor location. In his session at @ThingsExpo, Scott Allen, CMO of FreeWave, discussed how as IoT is increasingly adopted by industrial markets, there is going to be an increased demand for sensor data from the outermos...
Jul. 1, 2016 08:00 AM EDT Reads: 543
CenturyLink has announced that application server solutions from GENBAND are now available as part of CenturyLink's Networx contracts. The General Services Administration (GSA)'s Networx program includes the largest telecommunications contract vehicles ever awarded by the federal government. CenturyLink recently secured an extension through spring 2020 of its offerings available to federal government agencies via GSA's Networx Universal and Enterprise contracts. GENBAND's EXPERiUS™ Application...
Jul. 1, 2016 08:00 AM EDT Reads: 571
A strange thing is happening along the way to the Internet of Things, namely far too many devices to work with and manage. It has become clear that we'll need much higher efficiency user experiences that can allow us to more easily and scalably work with the thousands of devices that will soon be in each of our lives. Enter the conversational interface revolution, combining bots we can literally talk with, gesture to, and even direct with our thoughts, with embedded artificial intelligence, wh...
Jul. 1, 2016 07:15 AM EDT Reads: 1,312
"delaPlex is a software development company. We do team-based outsourcing development," explained Mark Rivers, COO and Co-founder of delaPlex Software, in this SYS-CON.tv interview at 18th Cloud Expo, held June 7-9, 2016, at the Javits Center in New York City, NY.
Jul. 1, 2016 07:15 AM EDT Reads: 717
"We work in the area of Big Data analytics and Big Data analytics is a very crowded space - you have Hadoop, ETL, warehousing, visualization and there's a lot of effort trying to get these tools to talk to each other," explained Mukund Deshpande, head of the Analytics practice at Accelerite, in this SYS-CON.tv interview at 18th Cloud Expo, held June 7-9, 2016, at the Javits Center in New York City, NY.
Jul. 1, 2016 12:30 AM EDT Reads: 761
Cloud Expo, Inc. has announced today that Andi Mann returns to 'DevOps at Cloud Expo 2016' as Conference Chair The @DevOpsSummit at Cloud Expo will take place on November 1-3, 2016, at the Santa Clara Convention Center in Santa Clara, CA. "DevOps is set to be one of the most profound disruptions to hit IT in decades," said Andi Mann. "It is a natural extension of cloud computing, and I have seen both firsthand and in independent research the fantastic results DevOps delivers. So I am excited t...
Jul. 1, 2016 12:00 AM EDT Reads: 623
The cloud promises new levels of agility and cost-savings for Big Data, data warehousing and analytics. But it's challenging to understand all the options – from IaaS and PaaS to newer services like HaaS (Hadoop as a Service) and BDaaS (Big Data as a Service). In her session at @BigDataExpo at @ThingsExpo, Hannah Smalltree, a director at Cazena, provided an educational overview of emerging "as-a-service" options for Big Data in the cloud. This is critical background for IT and data profession...
Jun. 30, 2016 04:00 PM EDT Reads: 572
Connected devices and the industrial internet are growing exponentially every year with Cisco expecting 50 billion devices to be in operation by 2020. In this period of growth, location-based insights are becoming invaluable to many businesses as they adopt new connected technologies. Knowing when and where these devices connect from is critical for a number of scenarios in supply chain management, disaster management, emergency response, M2M, location marketing and more. In his session at @Th...
Jun. 30, 2016 01:30 PM EDT Reads: 1,394


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Scott Carroll is a minor league baseball player who spent 2012 in the White Sox and Reds' farm systems. Baseball Reference doesn't have any stats for Carroll this season, so I'll just assume he is a professional pitchman for various products right now. Pitchman. Get it? (Fastball!) Carroll uploaded the video over a year ago and it already has nearly 4,000 views – three-quarters of which are likely ad agencies looking for the next big thing. (Home run!) Darren Rovell tweeted the video this week, so expect to see more big things from Carroll soon!
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Eagle Lake Lodge
Eagle Lake Lodge
Join now to see rating
Location: Ontario
Species Hunted: Canada Moose, Partridge, Ducks
State(s) Hunted: ON
Submitted by: Clarence Rainer
Review Submitted: Aug 30, 2010
Hunt Date: Sep 1, 2010
Species Hunted: Dove
Days Hunted: 1
Hunt Type: Guided
Primary Terrain: Praire
Method: Shotgun
Hunt Review
dove Hunt ... Join now to read dove hunt reviews for Eagle Lake Lodge in Ontario
Contact: David Stanley
Location: Ocate, New Mexico
Species Hunted: Elk, Mule Deer, Black Bear, Turkey, Mountain Lion
State(s) Hunted: NM
New Mexico Hunting Information
New Mexico is one of the top destinations for trophy Elk and Antelope hunting. Draw odds can be tough depending on the unit but landowner tags are also available for those who don't draw. Mule Deer are plentiful but generally of average size. Only a couple of units and reservations consistently produce big muleys.
Manitoba Hunting Information
Manitoba is known as a top destination for avid waterfowl hunters. Huge flocks of ducks and geese can be found from the Arctic coast of Hudson Bay to the prairie potholes on the southern border of this Canadian province. There is no legal requirement for non-resident waterfowl hunters to use a guide, but many are available and a high percentage of non-Canadian hunters utilize them. In addition black bear, Canada moose and whitetails are hunted throughout the province.
Colorado Hunting Information
Colorado is one of the best western states for trophy mule deer hunting and has the largest population of elk in the west.


text:
Blood pressure drugs can lower Alzheimer's risk by up to 50 per cent
Taking newer blood pressure drugs cuts the risk of Alzheimer's by up to 50 per cent, British scientists say.
Patients on these new drugs are also less likely to develop vascular dementia – a condition caused by problems in blood supply to the brain – than those on older medication.
The first study of its kind opens the door for a treatment that might delay, slow or even prevent dementia.
New hope: Researchers say taking new drugs could cut the risk of Alzheimer's
A researcher studies brain specimens afflicted with Alzheimer's disease - there is no current cure
People with high blood pressure are more at risk of developing Alzheimer's and similar diseases, but some are protected by the drugs they take, the study shows.
Bristol University researchers investigated medication which targets a biochemical pathway called the renin angiotensin system, thought to affect the onset of Alzheimer's.
The effect on the brain: This computer graphic compares an Alzheimer's brain (left) with a healthy brain. It is shrunken due to the degeneration and death of nerve cells
These drugs – known as ARBs and ACE inhibitors – have become increasingly prescribed in the past ten years. They include ramipril, captopril, losartan, candesartan and valsartan.
Scientists analysed data from 40,000 patients aged over 60 who were being treated for hypertension, or high blood pressure.
The degenerative condition is the most common form of dementia and affects more than 300,000 people in the UK.
It is estimated that it affects on in 14 people over the age of 65. It can be inherited in some cases.
Author Terry Pratchett is a high profile person with the disease.
The condition is caused by parts of the brain wasting away, particularly in the cerebral cortex.
As the grey matter wastes away, clumps of protein, known as 'plaques' and 'tangles', start to form in the brain. The plaques and tangles start to destroy even more brain cells.
Early symptoms include minor memory problems and saying the right words.
Later symptoms include severe confusion and dramatic changes of personality. A sufferer can also experience delusions.
There is no cure though there are some treatment that can slow the disease's progression.
The disease can shorten life-expectancy as sufferers can lose interest in eating and maintaining personal hygiene, leading to other illnesses.
One quarter had a type of dementia. The biggest benefit was for patients taking ARBs, with a 53 per cent drop in risk, compared with patients on ACE inhibitors, who had a 24 per cent lower risk of Alzheimer's or similar condition.
This was compared with those taking blood pressure drugs such as beta blockers, calcium channel blockers and diuretics – which have been around longer.
Alzheimer's patients were half as likely to be given ARBs, according to findings published online in the Journal of Alzheimer's Disease.
Study co-author Dr Patrick Kehoe, a pharmacologist at the Alzheimer's Research UK network in Bristol, said it was not possible to determine the minimum period of time needed to benefit from the drugs.
He explained that they block the effects of a hormone called angiotensin II, which results in the destruction of amyloid plaques in the brain that are the hallmark of Alzheimer's.
The next step is clinical trials to see if the drugs prevent mild cognitive impairment from progressing to full-blown dementia, or delay progression in patients with newly diagnosed Alzheimer's.
Blood pressure guidelines recommend patients under 55 have ARBs and ACE inhibitors, while older drugs are meant to be more effective in older patients.
Professor Peter Sever, an expert on hypertension at Imperial College London, said the study had 'very robust findings'.
More than 820,000 people in the UK have dementia.
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What does ATR stand for?
ATR stands for All Type Racer VW (Volkswagen) Club (French automobile club)
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123 Creations AP01H Be in Aspen. . . petit-point doorknob hanger
About this item
About this item
Important Made in USA Origin Disclaimer: For certain items sold by Walmart on Walmart.com, the displayed country of origin information may not be accurate or consistent with manufacturer information. For updated, accurate country of origin data, it is recommended that you rely on product packaging or manufacturer information.
Looking for the latest styles.
Looking for the latest styles- 123 Creations was created to provide American artisan handcrafted home decor accents gifts and accessories to those looking for something different yet tasteful- When you re in search of that feel good item or an inspiring gift we want to be your source- The items in this collection are handcrafted by specialty artisans and each piece is unique- Home Decor is becoming more popular every day- We all want to decorate our homes in a style befitting our taste and we re proud to offer outstanding designs that you ll never find in a big box store! The products are of the highest quality we combine an American made product line that is exceptional in value with unparalleled quality- 100 Percent Wool Hand Embroidered Petit Point Needlepoint Will add a touch of whimsy to any room Great gift for a friend who likes skiing- Be in Aspen petit-point doorknob hanger- Dimensions: 5'' x 8''- Manufactured to the Highest Quality Available- Design is stylish and innovative- Satisfaction Ensured- Great Gift Idea- SKU: CREATE792
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The Romeo's Taxi Toon Revolve attraction, December 6, 2007, 9:61 p.m.
The Romeo's Taxi Toon Revolve queue is like a journey across a real-life Toontown. The attraction taxis are supposed to look like Baldie the Cab, and as you drive you can revolve them by yanking the steering wheel.
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- PHOTOS: This Charming Texan Was Just Named America's Top Bartender
- LGBT New Yorkers Celebrate Pride and Resilience At The Center's Annual Garden Party
- PHOTOS: Instagram Users Respond To Orlando Tragedy In Beautiful And Creative Ways
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- PHOTOS: These Vintage Gay Pride Photos Are Absolutely Everything
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PHOTOS: Pop Duo Karmin Rock Great America Pride Night
May 28, 2014
Hundreds of folks kicked off this year's Pride season at Great America's 15th annual "Pride Night" just outside of San Jose. It was one fun-filled evening of music, dancing, and, of course, amusement park rides.
Ross Matthews served as the official master of ceremonies. Pop duo Karmin rocked the main stage, along with British pop star Neon Hitch and drag queen pop group DWV.
Check out photos from the night. And don't forget to check out GayCities' Official Pride Guides plus other Gay Days events to help get the most out of this year's celebrations in your city.
Photo credits: Marques Daniels


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Get excited about the new season with NYDJ's Skinny Fitted Ankle in Shifting Stripes Print. The black vertical stripes are optically slimming and is a stylish way to incorporate stripes into your wardrobe. Features five-pocket styling, zip-fly, button closure in our signature, look-a-size-smaller slimming fit and the perfect inseam that looks great whether paired with heels, wedges or flats.
(based on 2 reviews)
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By K
from Southern California
Best Uses
Comments about NYDJ CLARISSA SKINNY ANKLE IN SHIFTING STRIPES PRINT FINE LINE TWILL:
I ordered these with the other styles in mind from another retailer. I usually wear a 12 in NYDJ... I'm hoping the 16's fit. These are cute, however, very tight and very little stretch.
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Do not size down!
By BP
from Chicago, IL
I was disappointed as the these pants are very cute. However they are not made like the other NYDJ pants I've owned or even ordered with these. There is 3% stretch material apparently but it feels like none. I'm not even sure if these would fit IF I ordered a size up. I also ordered the Aileen trouser and fit beautifully just like my other NYDJ pants.
Bottom Line No, I would not recommend this to a friend
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