CA1047531A - .beta.-AMINO CARBONYLES EMPLOYES COMME CATALYSEURS DE LA SYNTHESE DE L'URETHANNE - Google Patents

.beta.-AMINO CARBONYLES EMPLOYES COMME CATALYSEURS DE LA SYNTHESE DE L'URETHANNE

Info

Publication number: CA1047531A
Authority: CA; Canada
Prior art keywords: foam; beta; catalysts; polyol; amine
Prior art date: 1972-11-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA283,348A

Other languages

English (en)

Inventor

David C. Priest

Michael R. Sandner

David J. Trecker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1972-11-27

Filing date

1977-07-22

Publication date

1979-01-30

1972-11-27 Priority claimed from US00309906A external-priority patent/US3821131A/en

1977-07-22 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1979-01-30 Application granted granted Critical

1979-01-30 Publication of CA1047531A publication Critical patent/CA1047531A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title abstract description 137
239000004814 polyurethane Substances 0.000 title abstract description 22
229920002635 polyurethane Polymers 0.000 title abstract description 21
238000002360 preparation method Methods 0.000 title abstract description 12
-1 2, 3-Diethylamino-N,N-dimethylpropionamide Chemical compound 0.000 claims description 60
150000001875 compounds Chemical class 0.000 claims description 37
HFEJDORPCWHHEE-UHFFFAOYSA-N 3-(dimethylamino)-n,n-dimethylbutanamide Chemical compound CN(C)C(C)CC(=O)N(C)C HFEJDORPCWHHEE-UHFFFAOYSA-N 0.000 claims description 3
MJQIFLISYRTKBK-UHFFFAOYSA-N 3-(diethylamino)-n,n-dimethylpropanamide Chemical compound CCN(CC)CCC(=O)N(C)C MJQIFLISYRTKBK-UHFFFAOYSA-N 0.000 claims 1
239000006260 foam Substances 0.000 abstract description 222
239000000203 mixture Substances 0.000 abstract description 124
150000001412 amines Chemical class 0.000 abstract description 89
238000009472 formulation Methods 0.000 abstract description 80
238000006243 chemical reaction Methods 0.000 abstract description 48
229910052757 nitrogen Inorganic materials 0.000 abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
229920000642 polymer Polymers 0.000 abstract description 19
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 abstract description 17
230000001413 cellular effect Effects 0.000 abstract description 17
238000004519 manufacturing process Methods 0.000 abstract description 16
230000015572 biosynthetic process Effects 0.000 abstract description 15
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 14
239000012948 isocyanate Substances 0.000 abstract description 9
230000008901 benefit Effects 0.000 abstract description 8
150000002513 isocyanates Chemical class 0.000 abstract description 6
125000000623 heterocyclic group Chemical group 0.000 abstract description 5
125000003368 amide group Chemical group 0.000 abstract description 4
230000009286 beneficial effect Effects 0.000 abstract description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract description 2
238000006555 catalytic reaction Methods 0.000 abstract description 2
125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
229920005862 polyol Polymers 0.000 description 113
150000003077 polyols Chemical class 0.000 description 110
239000000376 reactant Substances 0.000 description 57
239000000306 component Substances 0.000 description 43
239000000047 product Substances 0.000 description 38
239000005056 polyisocyanate Substances 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 description 29
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 28
238000000034 method Methods 0.000 description 27
229920001228 polyisocyanate Polymers 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
125000000217 alkyl group Chemical group 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
229920000570 polyether Polymers 0.000 description 23
239000004721 Polyphenylene oxide Substances 0.000 description 22
239000004094 surface-active agent Substances 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
125000002947 alkylene group Chemical group 0.000 description 17
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 17
229910052739 hydrogen Inorganic materials 0.000 description 16
239000001257 hydrogen Substances 0.000 description 16
229910052799 carbon Inorganic materials 0.000 description 15
230000003197 catalytic effect Effects 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
229920001400 block copolymer Polymers 0.000 description 12
230000009257 reactivity Effects 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000011496 polyurethane foam Substances 0.000 description 11
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
239000004604 Blowing Agent Substances 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
229920005830 Polyurethane Foam Polymers 0.000 description 10
239000003999 initiator Substances 0.000 description 10
239000000463 material Substances 0.000 description 10
230000000704 physical effect Effects 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 9
125000006353 oxyethylene group Chemical group 0.000 description 9
229910052760 oxygen Inorganic materials 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000000243 solution Substances 0.000 description 9
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000003063 flame retardant Substances 0.000 description 8
239000000178 monomer Substances 0.000 description 8
125000005702 oxyalkylene group Chemical group 0.000 description 8
229920001296 polysiloxane Polymers 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
239000007858 starting material Substances 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 6
238000005187 foaming Methods 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
238000002156 mixing Methods 0.000 description 6
229960005141 piperazine Drugs 0.000 description 6
150000003512 tertiary amines Chemical class 0.000 description 6
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000003426 co-catalyst Substances 0.000 description 5
238000007906 compression Methods 0.000 description 5
230000006835 compression Effects 0.000 description 5
239000006071 cream Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 5
125000001183 hydrocarbyl group Chemical group 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
230000006872 improvement Effects 0.000 description 5
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
229910052753 mercury Inorganic materials 0.000 description 5
229950000688 phenothiazine Drugs 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 5
150000004072 triols Chemical class 0.000 description 5
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000002015 acyclic group Chemical group 0.000 description 4
230000032683 aging Effects 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
229940000425 combination drug Drugs 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000013518 molded foam Substances 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
239000003921 oil Substances 0.000 description 4
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
239000010452 phosphate Substances 0.000 description 4
230000000379 polymerizing effect Effects 0.000 description 4
230000008569 process Effects 0.000 description 4
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 3
GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
239000012190 activator Substances 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
238000007259 addition reaction Methods 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
238000007664 blowing Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000011111 cardboard Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003431 cross linking reagent Substances 0.000 description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
238000007373 indentation Methods 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
125000005474 octanoate group Chemical group 0.000 description 3
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
238000012545 processing Methods 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
238000010998 test method Methods 0.000 description 3
125000005628 tolylene group Chemical group 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 2
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZCJKJJQMCWSWGZ-UHFFFAOYSA-N 3-(dimethylamino)-n,n-dimethylpropanamide Chemical compound CN(C)CCC(=O)N(C)C ZCJKJJQMCWSWGZ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
241001024304 Mino Species 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
230000009471 action Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
210000003850 cellular structure Anatomy 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
239000012975 dibutyltin dilaurate Substances 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
229940051250 hexylene glycol Drugs 0.000 description 2
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239000008103 glucose Substances 0.000 description 1
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239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
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239000012263 liquid product Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
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150000004706 metal oxides Chemical class 0.000 description 1
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OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
GMDIJHSRZKCTEB-UHFFFAOYSA-N methyl 3-butyl-3-(dimethylamino)heptanoate Chemical compound CCCCC(CCCC)(CC(=O)OC)N(C)C GMDIJHSRZKCTEB-UHFFFAOYSA-N 0.000 description 1
YMSLLIGKMYXCPK-UHFFFAOYSA-N methyl 3-morpholin-4-ylpropanoate Chemical compound COC(=O)CCN1CCOCC1 YMSLLIGKMYXCPK-UHFFFAOYSA-N 0.000 description 1
HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
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FDBROYKIDFATPC-UHFFFAOYSA-N n,n-di(butan-2-yl)-3-(diethylamino)propanamide Chemical compound CCC(C)N(C(C)CC)C(=O)CCN(CC)CC FDBROYKIDFATPC-UHFFFAOYSA-N 0.000 description 1
OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ZOTWHNWBICCBPC-UHFFFAOYSA-N n-ethyl-n-methylprop-2-enamide Chemical compound CCN(C)C(=O)C=C ZOTWHNWBICCBPC-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
102200043753 rs104893640 Human genes 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000003442 suberic acids Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
239000012970 tertiary amine catalyst Substances 0.000 description 1
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical class C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid group Chemical group C(\C(\C)=C\C)(=O)O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000009966 trimming Methods 0.000 description 1
HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
238000004018 waxing Methods 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA283,348A 1972-11-27 1977-07-22 .beta.-AMINO CARBONYLES EMPLOYES COMME CATALYSEURS DE LA SYNTHESE DE L'URETHANNE Expired CA1047531A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US00309906A US3821131A (en)	1972-11-27	1972-11-27	Beta-amino carbonyl catalysts for polyurethane preparation
CA184,992A CA1018975A (en)	1972-11-27	1973-11-05	Beta amino carbonyl catalysts for polyurethane preparation

Publications (1)

Publication Number	Publication Date
CA1047531A true CA1047531A (fr)	1979-01-30

Family

ID=25667400

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA283,348A Expired CA1047531A (fr)	1972-11-27	1977-07-22	.beta.-AMINO CARBONYLES EMPLOYES COMME CATALYSEURS DE LA SYNTHESE DE L'URETHANNE

Country Status (1)

Country	Link
CA (1)	CA1047531A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11267925B2 (en)	2017-06-30	2022-03-08	Dow Global Technologies Llc	Water-based polyurethane dispersions and their preparation
CN115612321A (zh) *	2022-09-27	2023-01-17	常州君合科技股份有限公司	一种环保型水性锌铝防腐涂液及其制备方法

1977
- 1977-07-22 CA CA283,348A patent/CA1047531A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11267925B2 (en)	2017-06-30	2022-03-08	Dow Global Technologies Llc	Water-based polyurethane dispersions and their preparation
CN115612321A (zh) *	2022-09-27	2023-01-17	常州君合科技股份有限公司	一种环保型水性锌铝防腐涂液及其制备方法
CN115612321B (zh) *	2022-09-27	2024-01-19	常州君合科技股份有限公司	一种环保型水性锌铝防腐涂液及其制备方法

Publication	Publication Date	Title
US4012445A (en)	1977-03-15	Beta-amino carbonyl catalysts for polyurethane preparation
US4220727A (en)	1980-09-02	Method of molding polyurethanes having mold release properties
US3933695A (en)	1976-01-20	Hydroxyalkenylsiloxane rigid poly urethane foam stabilizers
EP0708126B1 (fr)	2002-08-07	Procédé de préparation de mousses de polyuréthane à faible condensation et polyoxyalkylène-polyols spéciaux adaptés à ce procédé
US20070072951A1 (en)	2007-03-29	Silanol-functionalized compounds for the preparation of polyurethane foams
CA1040788A (fr)	1978-10-17	Catalyseurs de b-amino-nitrile pour la preparation de polyurethane
DE102014218635A1 (de)	2016-03-17	Herstellung von viskoelastischen Polyurethansystemen unter Einsatz von Blockpolymeren mit verknüpften Siloxanblöcken als Zellöffner
US4524102A (en)	1985-06-18	Microcellular polyurethane foams having integral skin
US3821131A (en)	1974-06-28	Beta-amino carbonyl catalysts for polyurethane preparation
CA1214900A (fr)	1986-12-02	Poly-n,n-hydroxyalcoylamides d'acides carboxyliques polybasiques et preparation
US5130344A (en)	1992-07-14	Use of polysiloxane polyoxyalkylene block copolymers for the preparation of rigid polyurethane foams
JPS62502970A (ja)	1987-11-26	ポリ（アルキレンカ−ボネ−ト）ポリオ−ルから製造された軟質ポリウレタンフォ−ム
US4478957A (en)	1984-10-23	Process for the production of highly resilient, cold-curing polyurethane foams
DE60020035T2 (de)	2005-11-17	Silicontenside zur Herstellung von weichen Polyurethanschaumstoffen
US3384599A (en)	1968-05-21	Siloxane-polyol compositions and process therefor
US3272762A (en)	1966-09-13	Preparation of cellular polyurethanes in the presence of a siloxane-oxyalkylene copolymer
CA1203350A (fr)	1986-04-15	Melange catalytique a groupe amino pour la stabilisation de mousse de polyurethane
US4727094A (en)	1988-02-23	Method for producing polyurethanes
US4011223A (en)	1977-03-08	Bis-(1,4-beta-amino carbonyl-ethyl)-piperazines
US5985948A (en)	1999-11-16	Use of silicone polyether copolymers in the production of high-resilience polyurethane foams
US3388101A (en)	1968-06-11	Silicon-containing polyurethanes
US4659772A (en)	1987-04-21	Novel polymer/polyols and uses thereof
US4088615A (en)	1978-05-09	Method of improving the diecuttability of polyester urethane foam and the improved diecuttable polyester urethane foams themselves
US3278465A (en)	1966-10-11	Manufacture of cellular polyurethane materials in the presence of a polysiloxane stabilizer
DE3844049A1 (de)	1990-07-05	Verfahren zur herstellung von flammwidrigen, elastischen polyurethan-weichschaumstoffen und niedrigviskose melamin-polyether-polyoldispersionen hierfuer