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Patent US4277581 - Polyamino-polyamide crosslinked with crosslinking agent - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA cosmetic composition for the hair comprises at least one water-soluble crosslinked polymer obtained by crosslinking a polyamino-polyamide with a crosslinking agent, said polyamino-polyamide being prepared by the polycondensation of (a) an acidic compound selected from the group consisting of (i) organic...http://www.google.com/patents/US4277581?utm_source=gb-gplus-sharePatent US4277581 - Polyamino-polyamide crosslinked with crosslinking agentAdvanced Patent SearchPublication numberUS4277581 APublication typeGrantApplication numberUS 06/057,684Publication dateJul 7, 1981Filing dateJul 16, 1979Priority dateNov 30, 1973Publication number057684, 06057684, US 4277581 A, US 4277581A, US-A-4277581, US4277581 A, US4277581AInventorsGuy Vanlerberghe, Henri Sebag, Jean-Francois Grollier, Alexandre ZysmanOriginal AssigneeL'orealExport CitationBiBTeX, EndNote, RefManPatent Citations (9), Referenced by (189), Classifications (32) External Links: USPTO, USPTO Assignment, EspacenetPolyamino-polyamide crosslinked with crosslinking agent
A cosmetic composition for the hair comprises at least one water-soluble crosslinked polymer obtained by crosslinking a polyamino-polyamide with a crosslinking agent, said polyamino-polyamide being prepared by the polycondensation of (a) an acidic compound selected from the group consisting of (i) organic dicarboxylic acid, (ii) ethylenically unsaturated aliphatic mono- or di-carboxylic acid, (iii) ester of said acids of (i) and (ii), and (iv) mixtures of (i), (ii) and (iii) on (b) a polyamine selected from the group consisting of bis-primary and mono- and bis-secondary polyalkylene polyamines, said polyamine (b) being replaceable by a member selected from the group consisting of (1) 0-20 mole percent hexamethylene diamine, (2) 0-40 mole percent bis-primary amine and (3) 0-40 mole percent bis-secondary amine, said crosslinking agent being selected from the group consisting of (a') simple bi-functional compounds selected from bis-halohydrins, bis-azetidinium, bis-haloacyl diamine and alkyl bis-halides, (b') oligomers obtained by the reaction of (1') a compound selected from the group consisting of the compounds in (a') above or an epihalohydrin,a bis-epoxide, or a bis-unsaturated derivative with (2') a compound reactive with the compound in (1'), and (c') the quaternized compounds comprising said crosslinked polymer alkylated with an alkylating agent selected from the group consisting of (a) epoxides, (b) ethylenically unsaturated compounds, (c) chloroacetic acid, and (d) alkane sultone selected from the group consisting of propane sultone and butane sultone. The crosslinking agent is employed in amounts of 0.025-0.35 mole per amine group in said polyamino-polyamide. The said crosslinked polymer is soluble in water in amounts of 10 weight percent thereof without essentially any gel formation and a 10 weight percent aqueous solution of the said crosslinked polymer has a viscosity greater than 3 centipoises at 25� C.
The crosslinked polyamino-polyamidde present in the hair conditioning composition of our earlier invention exhibits the following characteristics: (1) it is perfectly soluble in water up to 10 water percent concentration without forming a gel; (2) the viscosity of such a 10% solution in water at 25� C. is greater than 3 centipoises, the viscosity generally measuring between 3-200. More often the viscosity of such a solution is equal to or greater than 20 centipoises and lower than 50 centipoises; and (3) the polyamino-polyamide does not carry any reactive group and in particular it is chemically stable and does not have any alkylating characteristics.
The oligomerization reaction is generally carried out at temperatures between 0� and 95� C. and preferably between 0� and 50� C. in water, or in a solvent such as isopropanol, t-butanol, acetone, benzene, toluene, dimethylformamide or chloroform.
The quaternization reaction which provides the quaternization product described above, under III, is effected between 0� and 90� C. in water or in a solvent such as methanol, ethanol, isopropanol, t-butanol, alkoxy ethanols, acetone, benzene, toluene, dimethylformamide or chloroform.
The polycondensation is carried out in accordance with known procedures, bymixing the initial reactants; heating the resulting mixture to a temperature between 80� and 250� C., and preferably between 100� and 180� C., for 1 to 8 hours. The choice of the exact reaction time and temperature can depend on the choice of the particular reactants selected but the same is easily determined by those skilled in the art. After heating the reaction mixture at total reflux for 1/2 hour to 1 hour, the water or alcohol formed during the course of the polycondensation is removed at first at atmospheric pressure and then at subatmospheric pressure.
The addition reaction of ethylene diamine on the said unsaturated ester is carried out by mixing the reactants at a temperature between 5�-80� C. The polycondensation reaction is effected by heating the reactants for 30-60 minutes at reflux followed by eliminating the methyl alcohol formed, at a temperature of 120�-150� C.,or of the water formed at a temperature of 140�-175� C., initially under atmospheric pressure and finally under sub-atmospheric pressure of 15 mm of mercury.
The polyamino-polyamides (A) thus obtained have a viscosity in a 10% aqueous solution at 25� C. lower than 3 centipoises.
The crosslinking reaction is effected at a temperature between 20� C. and 90�0 C. using initially 20 to 30% aqueous solutions of the polyamino-polyamide to which is added the crosslinking agent by very smallfractions until there is obtained a significant increase in the viscosity, but without, however, forming a gel which no longer is soluble in water. The concentration is then rapidly adjusted to 10% by the addition of waterand the reaction mixture is then cooled.
The amount of crosslinking agent to use, which can vary according to the nature of the polyamino-polyamide and of the crosslinking agent can be easily determined by adding the desired crosslinking agent to an aqueous solution of the polyamino-polyamide until the viscosity of a 10% solution is at 25� C. between 3 centipoises and the gel state while preserving its perfect solubility in water.
The alkylation of the crosslinked polyamino-amides is carried out in an aqueous solution, at a concentration of 10 to 30% and at a temperature between 10� and 95� C.
(2) the viscosity of a 10% solution of polymer in water at 25� C. isgreater than 3 centipoises; and
To 619 g (6 moles) of diethylene triamine, there are added, with agitation and under a nitrogen atmosphere and over a 15 minute period, 876 g (6 moles) of adipic acid. The reaction mixture is then heated to 145�-150� C., the temperature at which condensation of wateris observed. The reaction mixture is maintained at reflux for 45 minutes atwhich time the water is removed by distillation, initially at ambient pressure for 2 hours and then under reduced pressure (15 mm Hg) for 1 hour. The heating temperature increases progressively up to 170� C.
To 236 g of a chloroform solution containing 57.2 g (0.289 mole) of bis(epoxypropyl)piperazine, there are added, over a one hour period, 36.4 g (0.289 mole) of dimethyl sulfate while maintaining the reaction mixture under agitation at 30� C.
To 500 g of an aqueous solution containing 100 g (0.585 amine equivalent) of polyamino-polyamide prepared by condensation of equimolar amounts of adipic acid and diethylene triamine, according to Example A, there are added, at ambient temperature, 22 g (0.057 mole) of quaternized crosslinking agent prepared in Example Ia. The temperature of the reactionmedium is then raised to 90� C.
After 20 minutes, gelling of the solution is observed. There are then rapidly added 698 g of water whereby a clear solution, yellow green in color, having 10% active material is obtained. The viscosity of this solution measured at 25� C. is 0.68 p at 87.93 sec.-1.
To 187.3 g of a chloroform solution containing 54.9 g (0.277 mole) of bis(epoxypropyl)piperazine, there are added, over a 1 hour period, 70 g (0.555 mole) of dimethyl sulfate, while maintaining the reaction medium under agitation at 30� C.
The medium thickened during the course of the addition and solidifies afterseveral hours at ambient temperature. The past is dissolved hot in dimethylformamide. When cold, the solution gives up white crystals having a meltingpoint of 205� C., for which the epoxide index is 4.25 meg/g.
To 476 g of an aqueous solution containing 95.2 g (0.557 amine equivalent) of the polyamino-polyamide prepared in Example A, there are added, at ambient temperature, 20 g (0.0425 mole) of the crosslinking agent preparedin Example IIA. The reaction mixture is maintained with agitation at 90� C. for 1 hour. Then the solution is adjusted to 10% active material by the addition of 656 g of water.
The solution is clear and has a yellow green color. Its viscosity, measuredat 25� C. is 0.27 p at 87.98 sec.-1.
To 380 g of an aqueous solution containing 194 g of bisacrylamide (1 mole) there are added, over a one hour period, and between 10 and 15� C.,223 g of an aqueous solution containing 56.8 g (0.66 mole) of piperazine. The reaction medium is then left to stand for 24 hours at ambient temperature. The solution is cloudy and thickens. It is clarified by heating and is then poured slowly into 5 liters of acetone. The crosslinking agent precipitates. After filtration and drying, a white solid of which the dry extract is 80% is recovered.
To 370 g of an aqueous solution containing 111 g (0.649 amine equivalent) of the polyamino-polyamide prepared according to Example A, there are added, at ambient temperature, 50 g of the crosslinking agent prepared in EXAMPLE IIIA. The temperature of the reaction medium is then raised to 90� C. After 30 minutes the medium gels. The solution is rapidly adjusted to 10% dry extract by the addition thereto of 1050 g of water.
A clear, yellow green solution is obtained. The viscosity of this solution measured at 25� C. is equal to 58 centipoises.
To 541 g of an aqueous solution containing 69.4 g (0.806 mole) of piperazine, there are added, over a 1 hour period, without exceeding 20� C., 92.5 g (1 mole) of epichlorohydrin. The reaction mixture isagain maintained for 1 hour with agitation at 20� C.; then at the same temperature there are added 60 g (0.6 mole) of 40% NaOH over a 1 hourperiod.
To 787.5 g of an aqueous solution containing 157.5 g (0.92 amine milliequivalent) of the polyaminopolyamide prepared in Example A, there are added, at ambient temperature, 268 g of an aqueous solution containing54.9 g of the crosslinking agent prepared in Example IVa. The temperature of the reaction medium is maintained for 4 h 50 min at 90� C. At this point, the reaction medium gels. By rapid addition of 1100 cc of water there is obtained a clear solution having 9.85% active material. Theviscosity of this solution, measured at 25� C. is equal to 73 centipoises.
To 330 g of an aqueous solution containing 67.7 g (0.752 amine equivalent) of the crosslinking agent prepared in Example IVA, there are added, over a1 hour period and without exceeding 30� C., 47.4 g (0.376 mole) of dimethylsulfate. The reaction medium is maintained with agitation for an additional 2 hours at this temperature.
To 327.7 g of an aqueous solution containing 65.5 g (0.383 amine equivalent) of the polyamino-polyamide prepared in Example A, there are added, at ambient temperature, 155 g of an aqueous solution containing 47.25 g of the crosslinking agent prepared in Example Va. After 4 hours ofheating at 85� C., the reaction mixture gels.
By rapid addition of 645 g of water, there is obtained a clear solution having 10% active material. The viscosity of this solution measured at 25� C. is 0.47 poise at 67.18 sec.-1.
To 50 g (0.212 mole) of 1,3-bis piperazine-2-propanol, (prepared by the addition of epichlorohydrin to piperazine - as described in Example 15 of French application No. 74 42279 of Nov. 28, 1972, or in Example 15 of U.S.Pat. No. 3,917,817) dissolved in 100 g of absolute ethyl alcohol, there areadded at a temperature between 0 and 5� C., 43.5 g (0.47 mole) of epichlorohydrin. The reaction mixture is left to stand 24 hours at 0� C. The crosslinking agent is then precipitated from its solutionin a large excess of ether. A white solid having a softening point of about120� C. is isolated.
To 386 g of an aqueous solution containing 77.2 g (0.452 amine equivalent) of the polyamino-polyamide prepared in Example A, there are added, at ambient temperature, 15.4 g (0.036 mole) of the crosslinking agent prepared in Example VIa. After 2 hr. 30 min. of heating at 90� C., the reaction medium gels. By rapid addition of 525 g of water, there is obtained a clear solution having 10% active material. The viscosity of this solution measured at 25� C. is 0.7 poise at 67.18 sec.-1.
To 100 g of an aqueous solution containing 200 g (1.170 amine equivalents) of the polyamino-polyamide prepared in Example A, there are added, at ambient temperature, 24 g (0.1 mole) of bis-(chloracetyl)piperazine. The temperature of the reaction medium is then raised to 90� C. After 30 minutes of heating the reaction medium gels. Then 1216 g of water are rapidly added and heating is continued at 80� C. for 1 hour. A clear solution is obtained having 10% active material. The viscosity of this solution measured at 25� C. is 0.29 poise at 88.41 sec.-1.
To 113.3 g of an aqueous solution containing 56.7 g (0.33 amine equivalent)of the polyamino-polyamide prepared in Example A, there are added, at ambient temperature, 60 g of an isopropanol solution containing 10 g (0.017 mole) of bis-(1,1-bromo undecanoyl) piperazine, prepared in ExampleVIIIa. The reaction medium is heated 2 hr. 30 min. at solvent reflux. The isopropanol is then distilled, while adding water until the attainment of a 10% aqueous solution of the resin (active material). The solution is slightly opalescent and its viscosity, measured at 25� C. is 0.052 poise at 87.93 sec.-1.
To 1149 g of an aqueous solution containing 172 g (12 moles) of piperazine there are added, over a 1 hour period, 246.7 g (2.66 moles) of epichlorohydrin while maintaining the reaction mixture with agitation at 20� C.
After an additional hour of agitation at 20� C., there are added, atthe same temperature and in the space of 1 hour, 133 g (1.33 mole) of 40% NaOH. A precipitation in the course of neutralization is observed. There are then added 638 g of water and the mixture is heated a few minutes at 50� C. to obtain a clear solution.
To 2000 g of an aqueous solution containing 400 g (2.34 amine equivalents) of the polyamino-polyamide prepared according to Example A, there are added 584 g of an aqueous solution containing 99.8 g of the crosslinking agent prepared in Example IXA. The reaction medium is then maintained withagitation at 90� C. for 5 hours. There are then added 2,414 g of water to obtain a clear solution having 10% active material. The viscosityof this solution measured at 25� C. is 0.22 poise.
To 1,221 g of an aqueous solution containing 172 g (2 moles) of piperazine there are added, over a 1 hour period and at 20� C., 277.5 g (3 moles) of epichlorohydrin while maintaining the reaction mixture under agitation and at 20� C. After an additional hour of agitation thereare added, at a temperature of 20� C., 100 g (1 mole) of a 40% aqueous solution of NaOH.
The reaction medium is maintained with agitation at 90� C. and after4 hours of heating, the solution gels.
A clear solution is obtained. The viscosity of this solution measured at 25� C. is 0.64 poise at 88.4 sec.-1.
______________________________________Compound of Example IIb                 0.6 g   active                         materialQuaternary polyvinyl-pyrrolidone copolymer havinga molecular weight of about100,000 and sold under thename "Gafquat 734"    0.5 gQuaternized cellulose soldunder the name"JR 400"              0.3 gEthyl alcohol, sufficient for                 15�Perfume               0.1 gWater, sufficient for 100 ccpH, adjusted to 8______________________________________
______________________________________Compound of Example IVb                 0.3 g   active                         materialQuaternary polyvinylpyrrolidonecopolymer having a molecularweight of about 100,000 andsold under the name"Gafquat 734"         0.5 gQuaternary cellulose, soldunder the name "JR 400"                 0.3 gEthyl alcohol, sufficient for                 15�Perfume               0.1 gWater, sufficient for 100 ccpH, adjusted to 8______________________________________
______________________________________Compound of Example Vb 0.6 g  active                         materialEthanol, sufficient for                  10�Dyes                   0.1 gPerfume                0.1 gWater, sufficient for  100 gThe pH of this solution is adjusted to 7.______________________________________
______________________________________Compound of Example IIIb                  0.4 g   active                          materialEthanol, sufficient for                  10�Dyes                   0.1 gPerfume                0.1 gWater, sufficient for  100 ccThe pH of this solution is adjusted to 8.______________________________________
______________________________________Compound of Example VIIIb                  0.5 g   active                          materialEthanol, sufficient for                  20�Dyes                   0.2 gPerfume                0.1 gWater, sufficient for  100 ccThe pH of this solution is adjusted to 6.______________________________________
______________________________________Compound of Example IIb                  0.8 g   active                          materialEthanol, sufficient for                  40�Dyes                   0.05 gPerfume                0.1 gWater, sufficient for  100 ccThe pH of this solution is adjusted to 7.______________________________________
______________________________________Reducing agent liquidThioglycolic acid       3 gThiolactic acid         2 gAmmonia, 22� Be  4 gTriethanolamine         3.5 gCompound of Example VIb 1.4 gPerfume                 0.2 gDyes                    0.05 gWater, sufficient for   100 gFixing Agent LiquidPotassium bromate       9.5 gCetylpyridinium chloride                   1 gTartaric acid, sufficient for                   pH = 6.5Perfume                 0.1 gDyes                    0.05 gWater, sufficient for   100 g______________________________________
______________________________________Reducing Agent LiquidThioglycolic acid       3.5 gThiolactic acid         2 gAmmonia, 22� Be  3.5 gTriethanolamine         4 gCompound of Example VIIIb                   2 gPerfume                 0.2 gDyes                    0.01 gWater, sufficient for   100 gFixing Agent LiquidPotassium bromate       8 gCetylpyridinium chloride                   0.8 gTartaric acid, sufficient for                   pH = 6.5Perfume                 0.2 gDyes                    0.05 gWater, sufficient for   100 g______________________________________
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cationic polymerUS20110182842 *Dec 23, 2010Jul 28, 2011Carine AiresCosmetic composition comprising at least one organosilicon compound, at least two anionic surfactants and at least one amphoteric surfactantCN1926228BJan 27, 2005May 26, 2010巴斯福股份公司Polymer for treating surfacesEP0763073A1 *Mar 28, 1995Mar 19, 1997Henkel CorporationWet strength resin composition and methods of making the same* Cited by examinerClassifications U.S. Classification525/420, 525/436, 525/419, 525/423, 525/426, 525/435, 523/105, 528/310, 528/342, 525/418, 528/332International ClassificationA61Q5/06, C08G69/48, A61Q5/00, A61Q5/02, A61K8/88, A61Q5/12, A61Q5/04Cooperative ClassificationA61Q5/04, A61Q5/12, C08G69/48, A61Q5/00, A61Q5/02, A61K8/88, A61Q5/06European ClassificationA61Q5/04, A61K8/88, A61Q5/00, A61Q5/02, C08G69/48, A61Q5/12, A61Q5/06RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS 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text:
The World is Against Me! – TheCagedBirdSings
“The world is against me”, he said with a sigh.
“Somebody stops every scheme I try
The world has me down and is keeping me there.
I don’t get a chance. Oh! The world is unfair!
When a fellow is poor, then he can’t get a show;
“What of Abe Lincoln?” I asked.
“Would you say, that he was much richer than you are today?
He hadn’t the chance of making his mark,
And his outlook was exceedingly dark;
Yet he clung to his purpose with courage most grim… And got to the top…
Was the world against him?”
“What of Ben Franklin?” I’ve often heard it said,
That many a times he went hungry to bed.
He started with nothing but courage to climb…
Yet he got to the top… Was the world against him?
“I could name a dozen, yes, hundreds, I guess,
Of poor boys, who’ve patiently climbed to success;
Who’ve fought themselves rich, if fortune they’d known;
Yet they rose in the world you are so quick to condemn,
And, I’m asking you now, was the world against them?”
courage, excuses, motivation, motivational poem, poem, world vs me
38 thoughts on “The World is Against Me!”
Thanks for the nice quote! A person himself be against him, not the world!
Absolutely. Thanks a lot ☺
Awesome lines of struggle and winning and rising and going down too. Beautiful, Himanshi.
Keep reading and sharing your thoughts and feedback.
Welcome Himanshi have a great day.
What a wonderful reminder of the men who struggled against all adversity and came out with flying colours
Thanks a lot. Hope this helps!
Lovely moral of the post!! It’s only a person individually against himself.. since his way of thoughts and perception makes him feel that the whole world is against him!!
Yes. The only obstacles are the thoughts!
The lines of Edgar Albert Guest remind me of Longfellow’s, “Not enjoyment, and not sorrow,
Find us farther than to-day”. Thanks for the trip, Himanshi….🤗
Thanks to you for sharing such beautiful lines!☺
Most men who are at the top started their life in poverty.
Ty for sharing 🍀
I feel like this is Donald Trump right now. (Whom i am not for nor against.)
Kindly further explain yourself.
Well, to be honest it was the first thing that popped in my head. When i first read the post, the vibe that i received was that of someone whom is fighting a battle of the pressures of the world. It seemed that they also complain about there situation a lot. It was just interesting to me. 🙂
Oh I get you. Donald Trump fighting with the world. The world is against him! Hilarious, though 😀😀
Sometimes i am a terrible conservative and think that instead of world war three….we should call it trump’s war…but then i roll over and go back to sleep.
Love it. It’s not what the world can do for you, but what you can do for yourself.
It was very interesting and a was a good read. The world is not against anyone. We all have a share of the world to conquer. I always imagine that individually we came into this world because we each have a piece to call ours, write our name on it, duly signed, sealed and delivered, call it “mine”, it belongs to someone! But yet it takes courage, hard work, persevere, energy, and at the end of the hard work, one will grab what belongs to them! Not easy, not difficult, with time, it all come easy! Thank you for posting!
Thanks for sharing your motivational thoughts. I suggest you write a post on it. Beautiful lines!!
Thank your for asking me to write about it. It will surely come up in a post I have already started to write, but it will be posted in a few months from now since the writing will come up with something that is about to happen. Have a happy week!
Okay. Do not forget to share the link with me as soon as you post it. Share the link on any of my post via your comment. Remember you are promising me a post!!☺☺
yup I will not forget to do that. I seek this post and will post the link here, I will keep a not on the page that I am writing to remind me,. Thanks for asking me to share the link.
A kind act from your side!☺
Beautiful posts😊
Mold the world to your liking if they are against you

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