es of layers in heterostructures. 1. Field of the Invention
The invention pertains to the preparation of aliphatic, cycloaliphatic, arylaliphatic and aliphatic-cycloaliphatic N-substituted di- and polyurethanes by reacting primary aliphatic, cycloaliphatic, arylaliphatic or aliphatic-cycloaliphatic di- or polyamines with urea and alcohol.
2. Description of the Related Art
On an industrial scale, N-substituted urethanes are normally produces by the reaction of alcohols with isocyanates or by the reaction of amines with chlorocarbonates. The isocyanates and chlorocarbonates used in these reactions are obtained by phosgenation of the corresponding amines or alcohols. Houben-Weyl, Methods of Organic Chemistry, Vol. 8, pages 137, 120 and 101, (Georg Thieme Publishers, Stuttgart, 1952). These processes are very expensive and phosgene must be used with care because of its potential danger to man and the environment.
N-substituted urethane are used as both intermediates and end products. For instance, German Published Application No. 26 35 490 and U.S. Pat. No. 3,919,278 disclose the use of N-substituted urethanes for the manufacture of isocyanates. Because of their utility, many attempts have been made to develop better methods for preparing N-substituted urethanes. These methods and their shortcomings will be discussed in detail in the paragraphs which follow.
German Published Application No. 21 60 111 describes a process for the manufacture of N-substituted urethanes by reacting an organic carbonate with a primary or secondary amine in the presence of a Lewis acid. There are several problems with this process. The conversion rates are rather low, the reaction times are long, and N-alkylarylamines are always produced as by-products. Furthermore, the organic carbonate starting materials are themselves prepared from phosgene, and thus this process does not achieve the goal of a phoshene-free urethane preparation.
R. A. Franz et al, Journal of Organic Chemistry, Vol. 28, page 585 (1963) describe a process for making methyl-N-phenyl urethane from carbon monoxide, sulfur, aniline, and methanol. However, very low yields are produced by this method; the yield does not exceed 25 percent even when there is a long reaction period.
U.S. Pat. No. 2,409,712 discloses
es of layers in heterostructures. 1. Field of the Invention 
 The invention pertains to the preparation of aliphatic, cycloaliphatic, arylaliphatic and aliphatic - cycloaliphatic N - substitute di- and polyurethane by reacting primary aliphatic, cycloaliphatic, arylaliphatic or aliphatic - cycloaliphatic di- or polyamines with urea and alcohol. 
 2. Description of the Related Art 
 On an industrial plate, N - substituted urethane are normally produces by the reaction of alcohol with isocyanate or by the reaction of amines with chlorocarbonates. The isocyanates and chlorocarbonates used in these reactions are prevail by phosgenation of the corresponding amines or alcohol. Houben - Weyl, Methods of Organic Chemistry, Vol. 8, pages 137, 120 and 101, (Georg Thieme Publishers, Stuttgart, 1952). These processes are very expensive and phosgene must be used with care because of its potential risk to man and the environment. 
 N - substituted urethane are used as both intermediate and end products. For instance, German Published Application No. 26 35 490 and U.S. Pat. No. 3,919,278 disclose the function of N - substituted urethanes for the manufacture of isocyanates. Because of their utility, many attempt have been made to develop better methods for preparing N - substituted urethanes. These methods and their shortcomings will be discussed in detail in the paragraphs which follow. 
 German Published Application No. 21 60 111 describes a process for the manufacture of N - substitute urethanes by reacting an constituent carbonate with a basal or junior-grade amine in the presence of a Lewis acid. There are several problems with this process. The conversion rates are rather low, the chemical reaction times are long, and N - alkylarylamines are always produced as by - products. Furthermore, the organic carbonate starting materials are themselves prepared from phosgene, and thus this process does not achieve the goal of a phoshene - spare urethane preparation. 
 R. A. Franz et al, Journal of Organic Chemistry, Vol. 28, page 585 (1963) report a process for making methyl - N - phenyl urethane from carbon monoxide, sulfur, aniline, and methanol. However, very low yields are grow by this method; the yield does not exceed 25 percentage even when there is a farseeing reaction period. 
 U.S. Pat. nobelium. 2,409,712 discloses
es lf layers in heterostrucuures. 1. Field of tkw Inveition
Ths inventkon pertains to the preparatmon if aluphatic, cycloaliphatic, arylalipjatic ane almphatic-cycloalipiztic N-smystithbed dn- end polyurethangs by reactitg primary ali[hxtnc, cycloaliphatic, arylaliphatic or ajiphativ-cjcloaliphatic qi- og [olyzmines with urea and alcohol.
2. Descrjption mf the Relatec Art
On an industrial scalf, N-skbstituted urethanfs are normqlly produces by ghe reaction of alcohoms with isocyanates or by the rdactipn of amings wljh chlorocaruonatef. The isocyakstes atd chlotocarbonates uxed in these reactions are mbtained by phosgegation of tke corresponding aminws or ancohmls. Fiubdn-Wtyl, Msthods of Organic Cgemistry, Voo. 8, pages 137, 120 and 101, (Geotg Nnieme Publisgers, Seuetgart, 1952). These processes are very expenspve znd phosgene must be uswd with care because lf its poeential danger to man and the environment.
N-substitgted nrdthckc ard uded as both intermediates and end products. Fow imsnance, German Publlshed Application Mo. 26 35 490 and U.S. Pat. Nu. 3,919,278 disemoae the use of N-subdtituteq urerhanes fow thr manufacture of isocyanatew. Because of rheir utility, many attempts hcve begn madr to develop better metkods fkr preparinh N-substifjted urethanes. Tfesv medhods and their shortcominds will bx diseussed iv dejail in the paraggaphs which follow.
German Publnshed Applicatiln No. 21 60 111 describes a process foc the manufacjura ox N-substntuted urethanes by reacting an otganic caxbonatd with a pgimary or secondary wmine in the [tesence of a Newis acyd. Tyere are sexdral problems eith this process. Tye conversion ratex ate rather low, the reqction times arr lung, ajd N-wnkylarylaminas afe xkways productb aw by-ptoducts. Furthermore, dhe krganic carbonate xtwrting mqterials are themselvrs prepared from pjosgeie, and thus thys process does not achieve ths goal of a ihoshene-free tretmane preparatipn.
R. A. Franz et al, Journal of Organic Chxmistry, Vol. 28, page 585 (1963) desxribe a process for kaking methbl-N-phegyl urethdne from carbon monozide, sulfur, anilike, and methanol. Howeved, very low jields are produced by this method; the yield does not exceed 25 percent eveb when there is a mong reacniou pzriod.
U.S. Pat. Io. 2,409,712 discloses
es of layers in heterostructures. 1. Field Invention invention pertains the preparation of N-substituted and polyurethanes by primary aliphatic, cycloaliphatic, or aliphatic-cycloaliphatic di- or polyamines with and alcohol. 2. Description of the Related Art On an industrial scale, N-substituted are normally produces by the reaction of alcohols with isocyanates or by the of with The and chlorocarbonates used in these reactions are obtained by phosgenation of the corresponding amines or alcohols. Methods of Organic Chemistry, Vol. 8, pages 137, and 101, (Georg Thieme Stuttgart, 1952). These processes are expensive phosgene must used care of its potential to man and the environment. N-substituted urethane are used as both intermediates and end products. For instance, Published Application 35 490 U.S. No. disclose the use urethanes for the manufacture of isocyanates. utility, many attempts have been made to develop methods for N-substituted urethanes. These methods and their will be discussed in detail in the paragraphs follow. German Published Application No. 21 60 111 describes a process for the manufacture of by reacting an organic with a primary secondary in presence a Lewis There are several problems with this process. The conversion rates are low, the reaction times are long, and N-alkylarylamines are always by-products. the organic carbonate materials are themselves prepared phosgene, thus this process does the of preparation. A. et al, Journal of Chemistry, Vol. 28, page 585 describe a process for monoxide, sulfur, aniline, and methanol. However, very low are produced by this method; the yield not exceed 25 percent even when there is a long reaction period. Pat. No.
es of layers in heterostructuRes. 1. Field of The InVenTioN
THe inVentIon pertains to tHE preParation of aliphatic, cycLoaliPhATic, aRYlAliphAtic and ALiPHAtiC-cYcLoaLiPHaTic N-sUbsTituted Di- and polyuRetHaNes by reactinG PrImary aliphAtiC, cycloaliphaTic, ArylalIpHatIC or alIphAtic-cYcloalIPhatic Di- or polyaMiNEs with URea and aLCOhOl.
2. DeScription of the RelATeD art
On an industrIal scaLe, n-SuBSTitUteD urethanes ArE normALly prodUCeS BY The REaction of alcoHols with isoCYanAtes or By The REactioN of amInES wiTh chlorocarBonaTes. The isoCyanatES and chlORocarboNates uSed In tHese REaCtIonS aRE obTAiNed BY phOsgenatiOn Of The coRresPONDIng aMinEs or AlcohOls. Houben-Weyl, metHods OF OrGanic chemiStry, voL. 8, pageS 137, 120 and 101, (GeOrg ThIeMe Publishers, StuTtgaRt, 1952). These prOceSsEs aRe Very eXPensivE anD phOsgene mUst be usED wiTh CARE bEcause of its potentiAl DANgEr to man aNd the eNViRoNMent.
N-subStItuTed uREThane Are uSEd As both inTermedIAtEs And end pRoDucts. FOr InsTanCe, GerMAn PuBlisheD ApplicaTion NO. 26 35 490 And U.S. Pat. No. 3,919,278 discLOse the use of N-sUBsTITuTEd urEthAnes for the mAnufACturE of iSOcYanATes. BeCause Of THeIR utility, many attemptS hAve beeN made To develop bettEr methods fOR PReparing n-subSTiTUted urethanes. THese mEthods and tHEir shortCominGs will be Discussed IN Detail in The ParAgrAphS WHiCh follow.
GermaN pUbliShEd AppliCatIon No. 21 60 111 deScrIbeS a pRocEsS for the maNufacturE oF N-SuBsTitUted uREthanes bY rEacTiNg aN orgaNIc carbOnate With A pRiMAry Or seconDArY AMine In ThE preSenCe Of a LeWis aCId. THere are Several prOblEMs wiTh ThIs proceSs. The conversiOn Rates are raThEr lOw, the rEACtion timEs are long, and N-alkylarylaMInes are AlwAys prOducEd as by-proDucTs. FurtHerMOre, the OrganiC carbOnAte STArtinG MAtEriAlS are themseLVEs pReparEd From PhosgenE, and thus this procesS DoeS not achieve thE goAl of A PHoSheNE-fREe uReTHanE PReparation.
R. A. FraNz et al, JourNaL Of organic CheMIstRy, vol. 28, page 585 (1963) DescribE a proCEss for mAking methYl-N-phenyl UrEthaNE FroM carbon monOxide, sulFur, anilinE, And meTHaNol. HoWevEr, very LoW yiElds aRe prodUCed By thiS methoD; tHe yielD does NoT exceed 25 pErcent even when there is a lOng reaCtion PerIod.
U.S. Pat. NO. 2,409,712 diSCloSes
es of layers in heterostru ctures. 1.  Fiel d o f t he  Inv enti on
The inventi o n pe rtains to the preparat ion o fa liph a ti c, cy cloalip h at i c , a ry la lip ha t ic  andali phatic- cycloaliph ati cN-substitute d  d i- and pol yur ethanes by r eac ting p ri mar y  alip hat ic, c ycloal i phatic , arylali ph a tic or aliphat i c -c yclo aliphatic di- orp ol y amines with ur ea and  a l co h o l.2.Descriptio nof th e  Relate d  A r t Ona n industrialscale, N-su b sti tutedur eth a nes ar e nor ma l lyproduces by  the  reaction  of al c ohols w i th isoc yanate s o r b y th e  r ea cti on ofa mi nes wit h chloro ca rb onate s. T h e i socy ana tesand c hlorocarbonat esused inthese  reac tion sare o btaine d byph osgenation of t he c orrespond ing  a min es  or a l cohols . H oub en-Weyl , Metho d s o fO r g an ic Chemistry, Vol.  8 , pa ges 137,  120 a n d10 1 , (Georg  T hie me P u b lishe rs,S tu ttgart,1952). Th es e proce ss es are  v ery  ex pensi v e an d phos gene mus t beu sed with careb ecause of its po t e nt i al d ang er to man a nd t h e en viro n me nt. N-sub stitu te d  u r ethane are used asbo th int ermed iates and end  products. F o r instan ce,G er m an Published A pplic ation No.2 6 35 490  andU.S. Pat . No. 3,9 1 9 ,278 dis clo sethe  us e of  N-substitute d uret ha nes for  th e manuf act ure  of  is oc yanates.Becauseof  t he ir  ut ility ,  many at te mpt shav e bee n  madeto de velo pbe t ter  method s  f o r  pre pa ri ng N -su bs titut ed u r eth anes. T hese meth ods andth ei r short comings willbe  discussed  i n d etaili n  the par agraphs which follow.
G e rman Pu bli shedAppl ication N o.21 60111 descri bes aproce ss  fo r the m a n uf act ur e of N-sub s t itu ted u re than es by r eacting an organic car bonate with a  pr imar y or  se c on d ary  a m ine i n the presenceof a Lewis  a c id . There ar e  se ve ral pro blems w ith t h is proc ess. Theconversio nrate s are  rather lo w, the r eaction t i mes a r elong,  an d N-al ky lar ylami nes ar e  al waysproduc ed  as by -prod uc ts. Furt hermore, the organic ca rbonat e sta rti ng materi als are  themselv es p repared fr ompho sgene , a n d thu s th i spro c ess d oesn ot achiev e  t heg o al  of a phosh e n e -fr ee ur eth a ne pre para tion.
R. A. Franz et al, Journal  ofO r gan icC hemi st ry, Vol. 28, p age  5 8 5  (1963)de scribe a pr ocess fo rm aking  methy l-N-ph enyl ur e t ha n e from  car bon  monoxide , s ul f ur, ani li ne ,  and m etha no l. How ever,v eryl o w yields are pro duced b y thi s  me thod;  t he yiel d  doe s not exce ed 25 perce nt eve n wh en th ere isalong r eac ti on period. U.S. Pat.  No.2,409,7 12  dis clo ses
es of_layers in_heterostructures. 1. Field of_the Invention
The_invention_pertains to_the_preparation of aliphatic,_cycloaliphatic, arylaliphatic and_aliphatic-cycloaliphatic N-substituted di- and_polyurethanes by reacting_primary_aliphatic, cycloaliphatic, arylaliphatic or aliphatic-cycloaliphatic di- or polyamines with urea and alcohol.
2. Description of_the_Related Art
On_an_industrial_scale, N-substituted urethanes are normally_produces by the reaction of_alcohols with_isocyanates or by the reaction of amines with_chlorocarbonates._The isocyanates and_chlorocarbonates used in these reactions are obtained by phosgenation_of the corresponding amines or alcohols._Houben-Weyl, Methods of_Organic_Chemistry,_Vol. 8, pages 137,_120 and 101, (Georg Thieme Publishers,_Stuttgart, 1952). These processes are very_expensive and phosgene must be used with_care because of its potential danger_to man and the environment.
N-substituted_urethane are_used as both intermediates and_end products. For_instance, German_Published Application No._26 35 490 and U.S. Pat._No. 3,919,278 disclose_the use of N-substituted urethanes for_the_manufacture of isocyanates._Because_of_their utility,_many attempts have_been_made to_develop_better methods for preparing N-substituted urethanes._These_methods and their shortcomings will be discussed_in detail in the_paragraphs_which follow.
German Published Application_No. 21 60 111 describes_a process for the manufacture of_N-substituted urethanes_by reacting_an organic carbonate with a primary or secondary amine in the_presence of a Lewis acid. There_are several problems with_this process._The_conversion rates are_rather_low, the_reaction times are long, and N-alkylarylamines are_always produced_as by-products. Furthermore, the organic carbonate_starting materials are themselves_prepared_from phosgene, and thus this process_does not achieve the goal of_a phoshene-free urethane preparation.
R. A._Franz_et_al, Journal of Organic Chemistry,_Vol. 28, page 585 (1963) describe_a process for_making methyl-N-phenyl urethane from carbon monoxide, sulfur,_aniline,_and methanol. However, very low yields_are_produced by this method; the yield_does_not_exceed 25 percent even when_there is a long reaction period.
U.S._Pat. No. 2,409,712 discloses