JPS6390529A - Production of urethane foam - Google Patents
Production of urethane foamInfo
- Publication number
- JPS6390529A JPS6390529A JP61237295A JP23729586A JPS6390529A JP S6390529 A JPS6390529 A JP S6390529A JP 61237295 A JP61237295 A JP 61237295A JP 23729586 A JP23729586 A JP 23729586A JP S6390529 A JPS6390529 A JP S6390529A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- catalyst
- urethane foam
- group
- alkyl group
- Prior art date
- 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.)
- Pending
Links
- 239000006260 foam Substances 0.000 title claims abstract description 28
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 229920005862 polyol Polymers 0.000 claims abstract description 18
- 150000003077 polyols Chemical class 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 229920000768 polyamine Polymers 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 150000001409 amidines Chemical class 0.000 claims abstract description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 17
- 239000004800 polyvinyl chloride Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000004604 Blowing Agent Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 238000005187 foaming Methods 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 230000003197 catalytic effect Effects 0.000 abstract description 9
- 239000004088 foaming agent Substances 0.000 abstract 2
- JJWKKSUCSNDHNJ-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethanol Chemical compound CC1=NC=CN1CCO JJWKKSUCSNDHNJ-UHFFFAOYSA-N 0.000 abstract 1
- -1 2-ethylhegysylene Chemical group 0.000 description 15
- 230000000694 effects Effects 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229920005830 Polyurethane Foam Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 239000011496 polyurethane foam Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-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
- 239000005977 Ethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000010097 foam moulding Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- MFYNHXMPPRNECN-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine;phenol Chemical class OC1=CC=CC=C1.C1CCCCN2CCCN=C21 MFYNHXMPPRNECN-UHFFFAOYSA-N 0.000 description 1
- QNWKSLSPYNPZFE-UHFFFAOYSA-N 2-[bis(methylamino)amino]ethanol Chemical compound CNN(NC)CCO QNWKSLSPYNPZFE-UHFFFAOYSA-N 0.000 description 1
- CESZUODSLPRJDU-UHFFFAOYSA-N 2-methyloxirane;oxirane;propane-1,2,3-triol Chemical compound C1CO1.CC1CO1.OCC(O)CO CESZUODSLPRJDU-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 240000002989 Euphorbia neriifolia Species 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- GSCCALZHGUWNJW-UHFFFAOYSA-N N-Cyclohexyl-N-methylcyclohexanamine Chemical compound C1CCCCC1N(C)C1CCCCC1 GSCCALZHGUWNJW-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002323 Silicone foam Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- QFFWRXOLQSLNQX-UHFFFAOYSA-N ethanamine N-methylmethanamine Chemical compound C(C)N.CNC QFFWRXOLQSLNQX-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000013514 silicone foam Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 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 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はウレタン発泡体の製造法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a method for producing urethane foam.
従来ポリウレタン発泡体、特にポリウレタン発泡体成型
品の製造法としてたとえばN、N−ジアルキルアミノア
ルキルアミン類の炭酸塩の如くイソシアネート基(NG
O)と反応する1級アミノ基やヒドロキシル基含有3級
アミン類を触媒として使用して触媒のポリウレタンフォ
ーム中での移動を抑え1表皮のポリ塩化ビニ/L/(以
下PVCと略記)と触媒との接触を避け、 pvcの変
色(通常「ビニルスティン」と呼ばれている)を抑制す
る技術がある。(特開昭59−191741号公報)〔
発明が解決しようとする問題点〕
しかし、 NGOと反応する基を有する3級アミン類は
発泡反応後期に触媒活性が低下する傾向があり、反応完
結がおくれ、脱型時間が延長するなど生産効率上の問題
があった。Conventionally, polyurethane foams, especially polyurethane foam molded products, have been produced using isocyanate groups (NG
A tertiary amine containing a primary amino group or a hydroxyl group that reacts with O) is used as a catalyst to suppress the movement of the catalyst in the polyurethane foam. There are techniques to prevent PVC discoloration (commonly called ``vinyl stain'') by avoiding contact with it. (Japanese Patent Application Laid-Open No. 59-191741)
[Problems to be Solved by the Invention] However, tertiary amines that have a group that reacts with NGOs tend to have reduced catalytic activity in the latter stages of the foaming reaction, which delays the completion of the reaction and prolongs demolding time, reducing production efficiency. I had the above problem.
本発明者らはPVCの変色が極めて少く1発泡反応後期
での触媒活性の低下がなく、シたがって脱型時間(フリ
ー・カップ発泡ではタック・フリー・タイムと直接相関
する。)の短い触媒を鋭意検討した結果1本発明に到達
した。すなわち本発明はポリイソシアネートとポリオー
ルを発泡剤および触媒の存在下に反応させてウレタン発
泡体を製造する方法において触媒の少なくとも一部とし
て一般式
(式中、RIは水素またはメチル基、R2は炭素数1な
いし4のアルキル基、R3とR4はそれぞれ水素。The present inventors have developed a catalyst with extremely little discoloration of PVC, no decrease in catalyst activity in the latter stages of the foaming reaction, and therefore a short demolding time (which is directly correlated with the tack-free time in free cup foaming). As a result of intensive studies, we have arrived at the present invention. That is, the present invention provides a method for producing a urethane foam by reacting a polyisocyanate and a polyol in the presence of a blowing agent and a catalyst. An alkyl group of numbers 1 to 4, R3 and R4 are each hydrogen.
メチ/L/、エチルまたはヒドロモジメチル基である。Methyl/L/, ethyl or hydromodimethyl group.
)で示される1−(2−ヒドロキシアルキル)−2−ア
ルキルイミダゾール類(a) ト一般式(式中、R5+
R6はそれぞれ炭素数1ないし4のアルキル基であり
%R7はエーテル酸素を含有していてもよいアルキレン
基である。)で示されるポリアミン類またはその塩(b
)および/または一般式(式中、R8は水素または炭素
数1ないし8のアルキル基であり、R9は炭素数1ない
し8のアルキル基であ、す、R8とR1は相互に結合し
てメチレジの数が3ないし5のアルキレン基で一つの環
を形成していてもよい。nは2または3である。)で示
されるアミジン類の塩(c)とを使用することを特徴と
するウレタン発泡体の製造法(@1発明)および上記の
製造法での表皮付きウレタン発泡体成型品の製造法(第
2発明)である。) 1-(2-hydroxyalkyl)-2-alkylimidazoles (a) represented by the general formula (wherein, R5+
R6 is an alkyl group having 1 to 4 carbon atoms, and %R7 is an alkylene group which may contain ether oxygen. ) or a salt thereof (b
) and/or general formula (wherein R8 is hydrogen or an alkyl group having 1 to 8 carbon atoms, R9 is an alkyl group having 1 to 8 carbon atoms, R8 and R1 are bonded to each other to form a methylated 3 to 5 alkylene groups may form one ring. n is 2 or 3). A method for manufacturing a foam (@1 invention) and a method for manufacturing a urethane foam molded product with a skin using the above manufacturing method (second invention).
一般式(1)において、R2の炭素数1〜4のアルキル
基としてはメチル、エチル、n−またはイソ−プロピ)
v 、 1− 、イソ−またはtert−ブチルなどの
直鎖または分岐を有するアルキル基があげられ。In general formula (1), the alkyl group having 1 to 4 carbon atoms in R2 is methyl, ethyl, n- or iso-propylene)
Examples include straight-chain or branched alkyl groups such as v, 1-, iso- or tert-butyl.
好ましくは触媒活性の点からメチル基である。R3とR
+はそれぞれ触媒活性の点からは水素であり、液状化(
低温流動性)の点からはR3かR4のいずれかまたはそ
れぞれがメチルまたはエチル基であり、PVCの変色抑
制の点からはNGOと反応性を有するヒドロキシメチル
基が好ましい。From the viewpoint of catalytic activity, a methyl group is preferred. R3 and R
+ is hydrogen from the point of view of catalytic activity, and liquefaction (
From the viewpoint of low temperature fluidity, either or each of R3 and R4 is a methyl or ethyl group, and from the viewpoint of suppressing discoloration of PVC, a hydroxymethyl group that is reactive with NGO is preferred.
一般式(1)で示される具体的な1−(2−ヒドロキシ
アルキル)−2−アルキルイミダゾール類としては例え
ば、1−(2−ヒドロキシメチ)v)−2−メチルイミ
ダゾール
プロピルグー2−メチルイミダゾール
−ヒドロキシエチ/l’ ) − 2−エチルイミダゾ
ール。Specific examples of 1-(2-hydroxyalkyl)-2-alkylimidazoles represented by general formula (1) include 1-(2-hydroxymethy)v)-2-methylimidazolepropyl-2-methylimidazole -hydroxyethyl/l') -2-ethylimidazole.
1−(2−tドo キシx 4−1v ) − 2 −
メチ)v−4−メチルイミダゾ−)v 、 1−(
2−ヒドロキシメチ/L/) −2 −tert 、ブ
チ/v−4−ヒドロキシメチルイミダゾール、1−(2
−ヒドロキシプロピル)−2−プロピ/L’ − 4,
5−ジヒドロギシメチルイミタソール,1−(2−ヒ
ドロキンプロピル)−2−エチル−4−メチ)L/−5
−ヒドロキシアルキル中タソ− tvr.i’〆1ヂ”
) j’ 、−fI+)I( +多$ー二鶴τ゛鞠1。1-(2-t x 4-1v) - 2-
meth)v-4-methylimidazo-)v, 1-(
2-hydroxymethy/L/)-2-tert, buty/v-4-hydroxymethylimidazole, 1-(2
-hydroxypropyl)-2-propy/L'-4,
5-dihydroxymethylimitasole, 1-(2-hydroquinepropyl)-2-ethyl-4-methy) L/-5
-Hydroxyalkyl tasot- tvr. i'〆1ヂ"
) j' , -fI+)I(+multi$-two cranes τ゛ball 1.
ル類にエチレンオキシドまたはプロピレンオキシドの付
加反応により容易に合成でき、それらの多くは低融点の
固状物または粘稠液状物である。They can be easily synthesized by addition reaction of ethylene oxide or propylene oxide to compounds, and most of them are solids or viscous liquids with low melting points.
一般式(2)においてR5とR6である炭素数1ないし
4のアルキル基としてはメチル、エチル、n−またはイ
ソ10ピル、n−、isoまたはtert 、−ブチル
などの直鎖または分岐のアルキル基があげられるが,高
い触媒活性の点からメチル基が好ましい。R7のエーテ
ル酸素を含有していてもよいアルキレン基としては炭素
数の合計が2〜12の直鎖または分岐のアルキレン基ま
たはエーテル酸素含有アルキレン基があげられ、エチレ
ン、n−フ゛ロピレン,テトラメチレン、ヘキサメチレ
ン、2−エチルヘギシレン,デカメチL/ 7などの直
鎖マ?.:ハ分岐のアルキレン基および前記のエチレン
ないしヘキサメチレンがエーテル結合で連結シたアルキ
レン基力あげられる。エチレン、プロピレン、ヘキサメ
チレン基またはこれらがエーテル結合で結合したエーテ
ル酸素含有アルキレン基であり、好ましくは触媒活性の
点からエチレン、n−フ゛ロピレンおよびこの両者がエ
ーテル結合したエーテル酸素含有アルキレン基であり,
塩を形成する酸としては無機および有機の酸のいずれで
もよく,好ましくは炭酸およびギ酸である。In general formula (2), the alkyl group having 1 to 4 carbon atoms which is R5 and R6 is a straight chain or branched alkyl group such as methyl, ethyl, n- or iso-10-pyl, n-, iso or tert, -butyl. However, methyl group is preferred from the viewpoint of high catalytic activity. Examples of the alkylene group R7 which may contain ether oxygen include linear or branched alkylene groups having a total of 2 to 12 carbon atoms or ether oxygen-containing alkylene groups, such as ethylene, n-propylene, tetramethylene, Straight chain polymers such as hexamethylene, 2-ethylhegysylene, decamethylene L/7? .. Examples include a branched alkylene group and an alkylene group in which the above-mentioned ethylene or hexamethylene are linked via an ether bond. Ethylene, propylene, hexamethylene groups, or an ether oxygen-containing alkylene group in which these are bonded with an ether bond, preferably ethylene, n-propylene, or an ether oxygen-containing alkylene group in which both are bonded with an ether bond, from the viewpoint of catalytic activity;
The salt-forming acid may be either inorganic or organic, with carbonic acid and formic acid being preferred.
一般式(2)で示される化合物としてはジアルキルアミ
ノアルキルアミン類(ジメチルアミンエチルアミン、ジ
メチルアミノプロピルアミン、ジエチルレア ミ )
フ゛ ロ ビル
アミン,ジメチルアミノオクチルアミン、シフ“ロピル
アミノフ“ロヒルアミン,ジメチルアミノへギサメチレ
ンアミンなど〕またジアルキルアミノアルコキシアルキ
ルアミン類(ジメチルアミノエトキシ10ピルアミン,
ジエチルアミノエトキシ10ピルアミン、S/メチルア
ミノヘキソキシフ゛ロピルアミンなど)があげられる。Examples of compounds represented by general formula (2) include dialkylaminoalkylamines (dimethylamine ethylamine, dimethylaminopropylamine, diethyl amine)
Dialkylaminoalkoxyalkylamines (dimethylaminoethoxy-10pyramine, dimethylaminoethoxy-10pyramine, etc.)
diethylaminoethoxy-10-pyramine, S/methylaminohexoxypropylamine, etc.).
塩の作成は相当する酸と反応させればよい。Salts can be created by reacting with the corresponding acid.
上記ポリアミン類のうち触媒活性の点より好ましい化合
物はジメナルアミノプロビルアミン,ジメ°チルアミノ
エチルアミンおよびそれらの炭酸塩であり,部分炭酸塩
は低臭灯の液状物である。Among the polyamines mentioned above, preferred compounds from the viewpoint of catalytic activity are dimenalaminopropylamine, dimethylaminoethylamine, and their carbonates, and the partial carbonates are liquid substances for low-odor lamps.
ジメチ)v7ミノフ゛ロピルアミンはジメチルアミンへ
アクリロニトリルを付加し,次いでニトリル基の還元に
より合成される。dimethy)v7 minophyllopylamine is synthesized by addition of acrylonitrile to dimethylamine, followed by reduction of the nitrile group.
本発明における触媒のアミジン類の塩(c)の一般式(
3)においてR8またはR9の炭素数1ないし4のアル
キル基としてはメチル、エア/L’、n−または1so
−プロピル、 n −、1so−またはtert、−ブ
チρ基があげられ、またR8とR9が相互に結合してメ
チレンの数が3ないし5のアルキレン基で一ツノ環を形
成する時はその原料の入手の容易さや原料コストからメ
チレンの数は8または5−h;好ましい。The general formula of the amidine salt (c) of the catalyst in the present invention (
In 3), the alkyl group having 1 to 4 carbon atoms for R8 or R9 is methyl, air/L', n- or 1so
-propyl, n-, 1so- or tert, -butyρ groups, and when R8 and R9 are bonded to each other to form a single horn ring with an alkylene group having 3 to 5 methylenes, the raw material The number of methylenes is preferably 8 or 5-h from the viewpoint of availability and raw material cost.
nは触媒活性の点から3が好ましい。一般式(3)で示
される化合物としては例えば1−メチルイミダシリン、
l、2−ジメチルイミダシリン、1−メチ/L’−1,
4,5,6−チトラハイドロビリミジン、1.2−ジメ
チル−1,4,5,6−チトラハイドロビリミジクロ(
4,8,0)ノネン゛−5かあげられる。好ましくは触
媒活性ヒ低臭気の点から後2者である。これらの化合物
の合成法は特公昭45−41226号公報などに記載さ
れている。これらアミジン類の塩としては特公昭45−
40558号公報および特公昭45−40554号公報
記載の有機酸塩であり1社としてはギ酸、酢酸、2−エ
チルヘキサン酸、オレイン酸。In terms of catalytic activity, n is preferably 3. Examples of the compound represented by the general formula (3) include 1-methylimidacyline,
l, 2-dimethylimidacyline, 1-methy/L'-1,
4,5,6-thitrahydrobyrimidine, 1,2-dimethyl-1,4,5,6-thitrahydrobyrimidine (
4,8,0) Nonen-5 are listed. The latter two are preferred in terms of catalyst activity and low odor. Methods for synthesizing these compounds are described in Japanese Patent Publication No. 45-41226. As the salts of these amidines,
Organic acid salts described in Japanese Patent Publication No. 40558 and Japanese Patent Publication No. 45-40554 include formic acid, acetic acid, 2-ethylhexanoic acid, and oleic acid.
ヌテアリン酸などの脂肪酸類やフェノール、クレゾール
などの石炭酸類である。They are fatty acids such as nutearic acid, phenol, and carbolic acids such as cresol.
本発明にかかる触媒イミダゾ−μ類(a)、ポリアミン
類(b)、アミジン類(C)の塩の使用量はこれら3種
類の全重量に基いて5〜95%、0〜80%、0〜50
%であり、好ましくは5〜80%、5〜75%、5〜4
0%である。The amount of the catalyst imidazo-μ (a), polyamine (b), and amidine (C) used in the present invention is 5 to 95%, 0 to 80%, 0 to 80%, based on the total weight of these three types. ~50
%, preferably 5-80%, 5-75%, 5-4
It is 0%.
本発明にかかる触媒配合物((a) + (b) +(
c) )はそれだけで使用することもできるが、必要に
より他の公知の触媒と併用することができる。他の触媒
としてはたとえばアミン系触媒(N、N、N・−トリメ
チμmN’−2−ヒドロキシエチルエチレンジアミン(
DABCO’ T〕、 1.8.5−トリス(3−ジメ
チルアミノプロピ/L/)へキサヒドロ−8−トリアジ
ン(POLYCAT41 、 POLYCAT DAB
COはエアプロダクツ、)
&ケミカルズ インク、製品、以下同じ)、N。Catalyst formulation according to the invention ((a) + (b) +(
c))) can be used alone, but if necessary, it can be used in combination with other known catalysts. Other catalysts include, for example, amine-based catalysts (N,N,N-trimethylμmN'-2-hydroxyethylethylenediamine (
DABCO'T], 1.8.5-tris(3-dimethylaminopropy/L/)hexahydro-8-triazine (POLYCAT41, POLYCAT DAB
CO stands for Air Products,) & Chemicals Inc., Products, hereinafter the same), N.
N、N−)リス(8−ジメチルアミノプロピ/し)アミ
ン(POLYCAT 9 ) 、 N−メチル−N、N
−ビス(3−ジメチルアミノプロピ/L/)アミン(P
OLYCAT’IT)、N−メチルジシクロヘキシルア
ミンCPOLYクタン、N、N−ジメチルアミノエタノ
ールアミンなど、また揮散性のN−メチルまたはN−エ
チルモルホリン類、N、N、N’、N’−テトラメチル
エチレンジアミン、トリエチルアミン〕および/または
金属触媒〔スタナスオクトエート、ジプチルすす′ジラ
ウレート、フォムレ11ノッUL−22(メルカプタン
すず、米国ライトコ製など〕と併用することもできる。N,N-)lis(8-dimethylaminopropyl/thi)amine (POLYCAT 9), N-methyl-N,N
-bis(3-dimethylaminopropyl/L/)amine (P
OLYCAT'IT), N-methyldicyclohexylamine CPOLYctane, N,N-dimethylaminoethanolamine, etc., as well as volatile N-methyl or N-ethylmorpholines, N,N,N',N'-tetramethylethylenediamine , triethylamine] and/or a metal catalyst [stannas octoate, diptylsot dilaurate, Fomure 11-not UL-22 (mercaptan tin, manufactured by Liteco, USA, etc.).
本発明に係る触媒と上記アミン系触媒との併用比率は重
量基準で通常1:10〜lO:1好ましくは1:4〜4
:lである。また、金属触媒との併用比率は1:5〜1
:O,OOl 好ましくはl:1−1:0.01である
。The combined ratio of the catalyst according to the present invention and the above amine catalyst is usually 1:10 to 1O:1 and preferably 1:4 to 4 on a weight basis.
:l. In addition, the ratio of combined use with metal catalyst is 1:5 to 1.
:O,OOl Preferably l:1-1:0.01.
本発明において使用する有機ポリイソシアネートおよび
ポリオールとしては硬質、半硬質、軟質ポリウレタンフ
ォーム、エラストマー発泡体およびポリウレタン成型品
などの製造に通常用いられているすべてのものがあげら
れる。The organic polyisocyanates and polyols used in the present invention include all those commonly used in the production of rigid, semi-rigid and flexible polyurethane foams, elastomer foams and polyurethane molded articles.
有機ポリイソシアネートとしては芳香族ポリイソシアネ
ート(トリレンジイソシアネート、ジフェニルメタンジ
イソシアネートなど)、脂肪族ポリイソシアネート(ヘ
キサメチレンジイソシアネートなど)、脂環式ポリイソ
シアネート(イソホロンジイソシアネートなど)これら
の変性物(例えばカルボジイミド変性)およびこれらと
活性水素化合物との反応による遊離イソシアネート含有
フ゛レポリマーがあげられる。Examples of organic polyisocyanates include aromatic polyisocyanates (tolylene diisocyanate, diphenylmethane diisocyanate, etc.), aliphatic polyisocyanates (hexamethylene diisocyanate, etc.), alicyclic polyisocyanates (isophorone diisocyanate, etc.), modified products thereof (for example, carbodiimide modification), and Examples include polypolymers containing free isocyanates produced by reaction of these with active hydrogen compounds.
これらの有機ポリイソシアネートのうち好まし°いもの
は芳香族ボリイソンアネートである。Among these organic polyisocyanates, aromatic borysonanate is preferred.
ポリオールとしては高分子ポリオールたとえばアルキレ
ンオキサイド類(エチレンオキサイド。Polyols include polymeric polyols such as alkylene oxides (ethylene oxide, etc.).
プロピレンオキサイド、l、2−およヒ1,4−ブチレ
ンオキサイドなど)の水、多雨アルコ−/I/(エチレ
ングリコール、プロピレングリコールなどのグリコール
;グリセリン、トリメチロールプロパン、トリエタノー
ルアミン、ペンタエリヌリトール、ソルピ)−/L/、
L/よ糖など3個以上のOH基を有するポリオ−/L/
)およびアミン化合物(エチレンジアミン、ジエチレン
トリアミン、トリレンジアミン、キシリレンジアミン、
ピペラジン、N−アミノアルキルヒベラジン、N、N−
ジメチルアミノプロピルアミン、シクロヘキシレンジア
ミンなど)への付加した構造を有するポリエーテルポリ
オ−/v:該ポリエーテルポリオールとエチレン性不飽
和単量体(アクリロニトリ/L/、スチレン。Propylene oxide, 1,2- and 1,4-butylene oxide, etc.) water, heavy rain alcohol/I/ (glycols such as ethylene glycol, propylene glycol; glycerin, trimethylolpropane, triethanolamine, pentaerythrin Thor, Sorpi)-/L/,
L/Polyol-/L/ having three or more OH groups such as sucrose
) and amine compounds (ethylenediamine, diethylenetriamine, tolylenediamine, xylylenediamine,
piperazine, N-aminoalkylhiberazine, N,N-
Polyether polyol/v having a structure added to dimethylaminopropylamine, cyclohexylene diamine, etc.): The polyether polyol and an ethylenically unsaturated monomer (acrylonitrile/L/, styrene, etc.).
メタクリル酸メチ/L/、7’タジエンなど)をラジカ
ル発生剤などの重合触媒の存在下に反応させた重合体ポ
リオール(米国特許第3,888,351号記載);ポ
リカルボン酸(コハク酸、セバシン酸、マレイン酸、ア
ジピン酸、フマル酸、フタル酸、ダイマー酸など)とと
記の多価アルコールとの反応によるポリエヌテルポリオ
ール;ポリエステルポリエーテルポリオールおよびこれ
らの二種以上の混合物があげられる。Polymer polyol (described in U.S. Pat. No. 3,888,351) prepared by reacting methacrylate (methacrylate/L/, 7'tadiene, etc.) in the presence of a polymerization catalyst such as a radical generator; polycarboxylic acid (succinic acid, Polyether polyols obtained by reacting sebacic acid, maleic acid, adipic acid, fumaric acid, phthalic acid, dimer acid, etc.) with polyhydric alcohols; polyester polyether polyols and mixtures of two or more of these. .
これらのポリオールのうちで好ましいものはポリエーテ
ルポリオールおよび重合体ボリオールテある。Preferred among these polyols are polyether polyols and polymer polyols.
本発明においては必要により、架橋剤ないしは鎖伸長剤
を使用することができ、たとえば低分子ポリオール(ト
リエタノールアミン、ジェタノールアミン、エチレング
リコール、ジエチレングリコール、ブタンジオール、ト
リメチロールプ゛ロバン、グリセリン、p−ビス(2−
ヒドロキシエチル)フェニレンエーテルなど)およびポ
リアミン(トリレンジアミン、キシリレンジアミン、ジ
アミノジフェニルメタン、メチレンビス−O−クロルア
ニリンなどンがあげられる。In the present invention, a crosslinking agent or a chain extender may be used if necessary, such as low molecular weight polyols (triethanolamine, jetanolamine, ethylene glycol, diethylene glycol, butanediol, trimethylolpropane, glycerin, -Bis(2-
(hydroxyethyl)phenylene ether, etc.) and polyamines (tolylene diamine, xylylene diamine, diaminodiphenylmethane, methylenebis-O-chloroaniline, etc.).
本発明において使用される発泡剤としてはハロゲン置換
脂肪族炭化水素系発泡剤(フロンガス。The blowing agent used in the present invention is a halogen-substituted aliphatic hydrocarbon blowing agent (fluorocarbon gas).
メチレンクロライドなど)、水などがあげられる。methylene chloride, etc.), water, etc.
また必要により界面活性剤〔シリコン整泡剤など〕2着
色剤、充填剤、雑燃剤、安定剤なども使用することがで
きる。Further, if necessary, surfactants (silicone foam stabilizers, etc.), colorants, fillers, miscellaneous combustible agents, stabilizers, etc. can also be used.
本発明に係る憩媒の使用量はポリオール100重量部に
対して通常0.01ないし5重量部、好ましくは0.1
ないし2重量部である。0.01重量部未満では触媒活
性が低く1反応完了までに時間がかかりすぎる。また5
重量部より大の使用量では得られたウレタンフオームの
物性、特に圧縮強1f(ILD)が低下する。The amount of the diverticulant used in the present invention is usually 0.01 to 5 parts by weight, preferably 0.1 parts by weight, per 100 parts by weight of the polyol.
2 parts by weight. If it is less than 0.01 part by weight, the catalyst activity will be low and it will take too long to complete one reaction. Also 5
If the amount used is larger than part by weight, the physical properties of the resulting urethane foam, especially the compressive strength 1f (ILD), will deteriorate.
ポリウレタン製造法は従来公知の方法と同じでよく、ワ
ンショット法、フ゛レポリマー法のいずれも適用できる
。またエラストマーまたはシーラント製造にも適用でき
、主原料、助剤、当量比、添加量なども従来と同様でよ
い。The polyurethane production method may be the same as a conventionally known method, and either a one-shot method or a full polymer method can be applied. It can also be applied to the production of elastomers or sealants, and the main raw materials, auxiliary agents, equivalent ratios, amounts added, etc. may be the same as conventional ones.
本発明のウレタン発泡体の製造法は特にPVCの表皮を
有するポリウレタンフォーム成型品の製造に有用である
が、これら以外の目的物の製造。The method for producing urethane foam of the present invention is particularly useful for producing polyurethane foam molded products having a PVC skin, but it can also be used for producing other objects.
RIM法による成型、開放モールドによる成型、真空成
型など、コールドキュアーおよびホットキュアー、スラ
ブ法、現地施工、スプレー法、注入。Molding by RIM method, molding by open mold, vacuum molding, etc., cold cure and hot cure, slab method, on-site construction, spray method, injection.
塗布、含浸など種々の方法にも適用できる。It can also be applied to various methods such as coating and impregnation.
PVC表皮付きウレタン発泡成型品を製造する方法とし
ては軟質ポリ塩化ビニルのシートを真空成型によって予
め型の内側にセットしておき、その中にウレタンフオー
ム製造用原液を注入して発泡成型させるか、あるいは、
ポリ塩化ビニルのフ”ラヌチゾルを金型の内面にて加熱
成型するいわゆるスラッシュモールド法によって金型の
内面にポリ塩化ビニルの表皮を形成させておき、然る後
ウレタンフオーム製造用原液を注入して発泡成型する方
法をとることができる。The method for producing a urethane foam molded product with a PVC skin is to first set a soft polyvinyl chloride sheet inside a mold by vacuum forming, then inject the stock solution for urethane foam production into the mold and perform foam molding. or,
A polyvinyl chloride skin is formed on the inner surface of the mold by the so-called slush molding method, in which polyvinyl chloride furanutisol is heated and molded on the inner surface of the mold, and then a stock solution for producing urethane foam is injected. A method of foam molding can be used.
上記のウレタン発泡体の製造に本発明の触媒を使用する
ことにより行うことができる。This can be achieved by using the catalyst of the present invention in the production of the above-mentioned urethane foam.
以下実施例により本発明を説明するが1本発明はこれに
限定されるものではない。The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.
実施例1〜8および比較例1.2
下記の発泡処方を用い、下記の発泡条件下で比較例の触
媒および本発明に係る触媒を用いて発泡し、いずれも良
好なウレタン発泡体が得られた。Examples 1 to 8 and Comparative Example 1.2 Using the following foaming recipe, foaming was carried out using the catalyst of the comparative example and the catalyst of the present invention under the following foaming conditions, and good urethane foams were obtained in both cases. Ta.
発泡処方:一
サンニツクスFA−708(注1) 100.0(重
量部)トリエタノールアミン(工業用)4.0水
2・5触媒
2.0または2.5,
2.3粗MDI(注2) 1O5(N
GOインデックスとして)
注1:三洋化成工業(株)製、グリセリンーフ゛ロピレ
ンオキサイドーエチレンオキサイド付加物、 08価約
34
注2:粗ジフェニルメタンジイソシアネート発泡条件ニ
ー
原料温度 22.0±0,5℃総原料重量
100g
攪拌時間 7秒
使用紙コツフ゛容量 ll
触媒ニー
A:1−(2−ヒドロキシエチ/L/)−2−メチルイ
ミダゾール
Bニジメチルアミノプロビルアミン部分炭酸塩含水物〔
1%pH10,5,水分(カールフィッシャー法)14
.0重量%、全アミン価840〕C: DBUの2−エ
チルヘキサン酸塩C’:DBUのフェノール塩
発泡操作二発泡処方中、粗MDI以外の原料を1eの紙
コツプに精秤し、均一混合物とし、次いで粗MDIを所
定量加え、直ちに7秒間高速攪拌し、紙コツプ内にウレ
タン発泡体がえられた。Foaming recipe: 1 Sunnics FA-708 (Note 1) 100.0 (parts by weight) Triethanolamine (industrial use) 4.0 Water
2.5 catalyst
2.0 or 2.5,
2.3 Crude MDI (Note 2) 1O5(N
(as GO index) Note 1: Manufactured by Sanyo Chemical Industries, Ltd., glycerin-propylene oxide-ethylene oxide adduct, 08 valence approximately 34 Note 2: Crude diphenylmethane diisocyanate foaming conditions raw material temperature 22.0±0.5℃ total Raw material weight
100g Stirring time 7 seconds Paper core volume used 11 Catalyst A: 1-(2-hydroxyethyl/L/)-2-methylimidazole B dimethylaminopropylamine partially hydrated carbonate [
1% pH 10.5, moisture (Karl Fischer method) 14
.. 0% by weight, total amine value 840] C: 2-ethylhexanoate of DBU C': Phenol salt of DBU Foaming operation In the two-foam formulation, raw materials other than crude MDI were accurately weighed into a 1e paper cup, and a homogeneous mixture was prepared. Then, a predetermined amount of crude MDI was added and immediately stirred at high speed for 7 seconds to obtain a urethane foam in the paper cup.
この発泡過程においてクリーム・タイム(CT) 。Cream thyme (CT) in this foaming process.
ライズ・タイム(RT)およびタック・フリー・タイム
(TPT)を測定した。Rise time (RT) and tack free time (TPT) were measured.
結果は次の第−表にまとめられている。The results are summarized in the table below.
第−表
第一表かられかるように触媒Bのポリアミン部分炭酸塩
のみの使用の場合はCTとRTが、触媒(A+B )
CBに20%のイミダゾ−/I/(All配合物知比し
て、はり同等であるのに対して、 TPTは360秒と
長く、触媒(A+B)のTPTは20%イミダゾール(
ト)併用効果によす340秒と短縮され、発泡反応後期
の触媒活性低下が抑制されていることがわかる。As shown in Table 1, when only the polyamine partial carbonate of catalyst B is used, CT and RT are equal to the catalyst (A+B).
The TPT of the catalyst (A+B) was as long as 360 seconds, while the beam was equivalent to that of the CB with 20% imidazole/I/(All).
g) It was shortened to 340 seconds due to the combined effect, and it can be seen that the decrease in catalyst activity in the latter stage of the foaming reaction was suppressed.
さらに触媒(A+B)に第8成分であるアミジン塩であ
るDBUの2−エチルへキサン酸塩(C)を0.5部併
用した場合CTは全く変らず、 RTは5秒短縮するだ
けで発泡反応初期の活性にはほとんど変化がみられない
が、TPTは240秒と大巾に100秒も短縮され1反
応後期で触媒活性が低下していない。Furthermore, when 0.5 part of DBU 2-ethylhexanoate (C), which is an amidine salt, which is the eighth component, is used in combination with the catalyst (A + B), CT does not change at all, RT shortens by only 5 seconds, and foaming occurs. Although there is almost no change in the activity in the early stage of the reaction, the TPT was shortened by a large 100 seconds to 240 seconds, and the catalyst activity did not decrease in the late stage of one reaction.
さらに触媒(A+B)にDBUのフェノール塩(C′)
を0.3部併用した時も同様な結果かえられた。Furthermore, DBU phenol salt (C') is added to the catalyst (A+B).
Similar results were obtained when 0.3 parts of
一方、イミダゾール誘導体(8)を含有する( A+B
+C)とA成分を含有しないCB+C)のTPTを比較
すると240秒と290秒と50秒の大差があり、イミ
ダゾール誘導体(8)成分の含有の有無がTPTに大き
い影響を与えていることがわかる。触媒Bの20形配合
物として1−(2−ヒドロキシン“ロピ)V)−2−メ
チルイミダゾ−pを使用した時も上記と同様な傾向がみ
られた。On the other hand, containing the imidazole derivative (8) (A+B
Comparing the TPT of +C) and CB+C) that does not contain component A, there is a large difference of 240 seconds, 290 seconds, and 50 seconds, indicating that the presence or absence of the imidazole derivative (8) component has a large influence on TPT. . A similar trend was observed when 1-(2-hydroxyne "lopi)V)-2-methylimidazo-p was used as Form 20 formulation of Catalyst B.
実施例4〜6および比較例a (pvc表皮付きウレタ
ン発泡体成型品の製造)
明細吉の浄書(内容に変更なし)
前記の発泡処方で原料温度20 + 0.5°C,20
X20X1.0CIRのモールドを使用し、モールド内
側にr’vcシートを貼付け、モールドの型温40±2
°C1総原料重量12Ofを前記と同様に攪拌し、モー
ルド(こ注入発泡し、室温10分間キュアーし、脱型し
てpvc表皮付きウレタン発泡体成型品を製造した。Examples 4 to 6 and Comparative Example a (Manufacture of urethane foam molded product with PVC skin) Seikichi's print (no change in content) With the above foaming recipe, the raw material temperature was 20 + 0.5°C, 20
Use a mold of
C1 total raw material weight of 12Of was stirred in the same manner as above, poured into a mold, foamed, cured at room temperature for 10 minutes, and demolded to produce a urethane foam molded product with a PVC skin.
PvCシートを除いたモールドフオームの密取は0.2
5〜0.26であった。Contamination of mold form excluding PvC sheet is 0.2
It was 5-0.26.
このテストピースを120’Cのオーブン中で50時間
処理してPVCシートの変色をしらべた。This test piece was treated in an oven at 120'C for 50 hours to examine discoloration of the PVC sheet.
着色評価は次の基準で示す。Coloring evaluation is shown based on the following criteria.
1:わずかに着色、2:橙色に着色、3:赤色に着色、
4:赤茶色に着色、5:黒色に着色第二表
用ウレタン触媒であるトリエチレンヅアミンに比しては
るかに少いことがわかる。1: Slightly colored, 2: Orange colored, 3: Red colored,
4: Colored reddish-brown; 5: Colored black. It can be seen that the amount is much less than triethyleneduamine, which is the urethane catalyst used in Table 2.
本発明のウレタン発泡体の製造法は発泡反応後期の反応
完結がおくれることがなく、したがって脱型時間が短縮
し、生産効率が向上する。The method for producing a urethane foam according to the present invention does not delay the completion of the late stage of the foaming reaction, thus shortening demolding time and improving production efficiency.
さらに本発明のPVC表皮付きウレタン発泡体成型品も
生産効率よく生産でき、かつそのPVCの変色も少い。Furthermore, the PVC skinned urethane foam molded product of the present invention can be produced with high production efficiency, and the PVC discolors less.
通常イソシアネートと反応する基を有する3級アミン類
を触媒としてウレタン発泡体を製造する場合pvcの変
色は抑制できるが反応後期の触媒活性が低下し、成型品
の脱型時間が長くなる。Generally, when urethane foam is produced using a tertiary amine having a group that reacts with isocyanate as a catalyst, discoloration of PVC can be suppressed, but the catalyst activity in the latter stage of the reaction decreases, and the demolding time of the molded product becomes longer.
本発明に係る1−(2−ヒドロキンアルキル)イミダゾ
ール類、ポリアミン類および/またはアミジン類の塩と
の触媒はイソシアネート基と反応する1級アミノ基〔ポ
リアミン類(b)〕およびヒヒドロキシル〔イミダゾー
ル類(a)〕をそれぞれ有する3級アミン類からなるが
アミジン類の塩類により発泡反応後期の低下が少く、特
に1−(2−ヒドロキシアルキtIL/) −2〜アル
キルイミダゾール類の存在に於て顕著である。The catalyst of the present invention with a salt of 1-(2-hydroquinalkyl)imidazole, polyamine and/or amidine is a primary amino group [polyamine (b)] that reacts with an isocyanate group and a hydroxyl [imidazole]. The foaming reaction is composed of tertiary amines each having type (a)], but due to amidine salts, there is little decrease in the latter stage of the foaming reaction, especially in the presence of 1-(2-hydroxyalkyl/)-2~alkylimidazoles. Remarkable.
さらに表皮にPVCを使用したウレタン発泡体成型品に
使用した場合も、PVCンーシー変色も少く実用上極め
て有用である。Furthermore, when used in urethane foam molded products using PVC for the skin, there is little discoloration of PVC, making it extremely useful in practice.
特許出願人 サンマプロ株式会社
手 続 補 正 書
昭和62年2月IC7日
1、事件の表示
昭和61年特許願第237295号
2、発明の名称
ウレタン発泡体の製造法
3、補正をする者
4、代理人
住 所 京都市東山区−橋野本町11番地の15、
補正命令の日付
昭和62年1月7日
6、 補正により増加する発明の数
7、補正の対象
明細書の「発明の詳細な説明」の欄
8、補正の内容
明細書第22頁を別紙のものと置きかえる。Patent Applicant Sanmapro Co., Ltd. Procedures Amendment Document February 1988 IC 7 1, Case Description 1988 Patent Application No. 237295 2, Title of Invention Process for Producing Urethane Foam 3, Person Making Amendment 4, Agent Address: 15-11 Hashino Honmachi, Higashiyama-ku, Kyoto City.
The date of the amendment order is January 7, 1985 6, the number of inventions to be increased by the amendment 7, column 8 of "Detailed explanation of the invention" of the specification subject to the amendment, and page 22 of the specification of the contents of the amendment as attached. Replace it with something.
Claims (1)
媒の存在下に反応させてウレタン発泡体を製造する方法
において触媒の少くとも一部として一般式 ▲数式、化学式、表等があります▼…(1) (式中、R_1は水素またはメチル基、R_2は炭素数
1ないし4のアルキル基、R_3とR_4はそれぞれ水
素、メチル、エチルまたはヒドロキシメチル基である。 )で示される1−(2−ヒドロキシアルキル)−2−ア
ルキルイミダゾール類(a)を使用することを特徴とす
るウレタン発泡体の製造法。 2、触媒として(a)と一般式 ▲数式、化学式、表等があります▼…(2) (式中、R_5、R_6はそれぞれ炭素数1ないし4の
アルキル基であり、R_7はエーテル酸素を含有してい
てもよいアルキレン基である。)で示されるポリアミン
類またはその塩(b)および/または一般式 ▲数式、化学式、表等があります▼…(3) (式中、R_8は水素または炭素数1ないし8のアルキ
ル基であり、R_9は炭素数1ないし8のアルキル基で
あり、R_8とR_9は相互に結合してメチレンの数が
3ないし5のアルキレン基で一つの環を形成していても
よい。nは2または3である。)で示されるアミジン類
の塩(c)ヒを使用する特許請求の範囲第1項記載の製
造法。 3、ポリイソシアネートとポリオールを発泡剤および触
媒の存在下に反応させて表皮を有するウレタン発泡体成
型品を製造する方法において触媒の少くとも一部として
一般式 ▲数式、化学式、表等があります▼…(1) (式中、R_1は水素またはメチル基、R_2は炭素数
1ないし4のアルキル基、R_3とR_4はそれぞれ水
素、メチル、エチル、またはヒドロキシメチル基である
。)で示される1−(2−ヒドロキシアルキル)−2−
アルキルイミダゾール類(a)を使用することを特徴と
する表皮付きウレタン発泡体成型品の製造法。 4、触媒として(a)と一般式 ▲数式、化学式、表等があります▼…(2) (式中、R_5、R_6はそれぞれ炭素数1ないし4の
アルキル基であり、R_7はエーテル酸素を含有してい
てもよいアルキレン基である。)で示されるポリアミン
類またはその塩(b)および/または一般式 ▲数式、化学式、表等があります▼…(3) (式中、R_8は水素または炭素数1ないし8のアルキ
ル基であり、R_8は炭素数1ないし8のアルキル基で
あり、R_8とR_9は相互に結合してメチレンの数が
3ないし5のアルキレン基で一つの環を形成していても
よい。nは2または3である。)で示されるアミジン類
の塩(c)とを使用する特許請求の範囲第3項記載の製
造法。 5、表皮がポリ塩化ビニルである特許請求の範囲第3項
または第4項記載の製造法。[Claims] 1. In a method for producing urethane foam by reacting polyisocyanate and polyol in the presence of a blowing agent and a catalyst, at least a part of the catalyst includes a general formula ▲ mathematical formula, chemical formula, table, etc. ▼...(1) (In the formula, R_1 is hydrogen or a methyl group, R_2 is an alkyl group having 1 to 4 carbon atoms, and R_3 and R_4 are hydrogen, methyl, ethyl or hydroxymethyl group, respectively.) 1- A method for producing a urethane foam, comprising using (2-hydroxyalkyl)-2-alkylimidazoles (a). 2. As a catalyst, there are (a) and general formula ▲ numerical formula, chemical formula, table, etc. ▼... (2) (In the formula, R_5 and R_6 are each an alkyl group having 1 to 4 carbon atoms, and R_7 contains ether oxygen. polyamines or their salts (b) and/or general formula ▲ Numerical formula, chemical formula, table, etc. ▼... (3) (In the formula, R_8 is hydrogen or carbon R_9 is an alkyl group having 1 to 8 carbon atoms, and R_8 and R_9 are bonded to each other to form one ring with an alkylene group having 3 to 5 methylenes. 2. The manufacturing method according to claim 1, which uses a salt of an amidine represented by (c) (n is 2 or 3). 3. In the method of producing a urethane foam molded product having a skin by reacting polyisocyanate and polyol in the presence of a blowing agent and a catalyst, at least a part of the catalyst includes a general formula ▲ mathematical formula, chemical formula, table, etc. ▼ ...(1) (In the formula, R_1 is hydrogen or a methyl group, R_2 is an alkyl group having 1 to 4 carbon atoms, and R_3 and R_4 are each hydrogen, methyl, ethyl, or hydroxymethyl group.) 1- (2-hydroxyalkyl)-2-
A method for producing a urethane foam molded product with a skin, characterized by using an alkylimidazole (a). 4. As a catalyst, there are (a) and general formula ▲ numerical formula, chemical formula, table, etc. ▼... (2) (In the formula, R_5 and R_6 are each an alkyl group having 1 to 4 carbon atoms, and R_7 contains ether oxygen. polyamines or their salts (b) and/or general formula ▲ Numerical formula, chemical formula, table, etc. ▼... (3) (In the formula, R_8 is hydrogen or carbon It is an alkyl group having a number of 1 to 8, R_8 is an alkyl group having 1 to 8 carbon atoms, and R_8 and R_9 are bonded to each other to form one ring with an alkylene group having 3 to 5 methylenes. and n is 2 or 3). 5. The manufacturing method according to claim 3 or 4, wherein the skin is made of polyvinyl chloride.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61237295A JPS6390529A (en) | 1986-10-06 | 1986-10-06 | Production of urethane foam |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61237295A JPS6390529A (en) | 1986-10-06 | 1986-10-06 | Production of urethane foam |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6390529A true JPS6390529A (en) | 1988-04-21 |
Family
ID=17013250
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61237295A Pending JPS6390529A (en) | 1986-10-06 | 1986-10-06 | Production of urethane foam |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6390529A (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01256511A (en) * | 1988-04-05 | 1989-10-13 | Nippon Niyuukazai Kk | Manufacture of polyurethane |
JPH02240125A (en) * | 1989-03-14 | 1990-09-25 | Sanyo Chem Ind Ltd | Polymer polyol composition and production of foam |
JPH02281021A (en) * | 1989-04-21 | 1990-11-16 | Sanyo Chem Ind Ltd | Production of polymerized polyol composition and foam |
JPH0333120A (en) * | 1989-06-30 | 1991-02-13 | Tokyo Seat Kk | Production of molded urethane foam |
JPH0395212A (en) * | 1989-06-06 | 1991-04-19 | Tosoh Corp | Preparation of rigid polyurethane foam |
JPH03122108A (en) * | 1989-10-06 | 1991-05-24 | Tosoh Corp | Catalyst for producing polyurethane foam of spray type and production thereof using the same catalyst |
JPH03128913A (en) * | 1989-07-28 | 1991-05-31 | Tosoh Corp | Production of highly resilient polyurethane foam |
JPH03131618A (en) * | 1989-10-18 | 1991-06-05 | Tosoh Corp | Catalyst for production of phenol-based urethane foam and production using the same catalyst |
JPH03200825A (en) * | 1989-09-11 | 1991-09-02 | Tosoh Corp | Production of highly elastic polyurethane foam |
JPH04202215A (en) * | 1990-11-29 | 1992-07-23 | Tokyo Seat Kk | Production of urethane foam molding |
JPH04214712A (en) * | 1990-09-19 | 1992-08-05 | Tokyo Seat Kk | Production of molded product of urethane foam |
JPH04227619A (en) * | 1990-04-11 | 1992-08-17 | Tosoh Corp | Production of flexible polyurethane foam excellent in gas diffusibility |
JPH04298519A (en) * | 1990-09-19 | 1992-10-22 | Tokyo Seat Kk | Production of molded urethane foam |
JPH08198933A (en) * | 1995-01-26 | 1996-08-06 | Nishikawa Kasei Co Ltd | Production of foamed rigid urethane molding having skin layer and interior automotive trim having the same molding |
JP2002338649A (en) * | 2001-05-22 | 2002-11-27 | Tosoh Corp | Catalyst for producing polyurethane resin and method for producing polyurethane resin |
EP1262500A1 (en) * | 2001-05-22 | 2002-12-04 | Tosoh Corporation | Catalyst for production of a polyurethane resin and method for producing a polyurethane resin |
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US3448065A (en) * | 1965-09-07 | 1969-06-03 | Air Prod & Chem | Polyurethane catalysis employing n-hydroxyalkyl substituted imidazole |
Cited By (19)
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JPH01256511A (en) * | 1988-04-05 | 1989-10-13 | Nippon Niyuukazai Kk | Manufacture of polyurethane |
JPH02240125A (en) * | 1989-03-14 | 1990-09-25 | Sanyo Chem Ind Ltd | Polymer polyol composition and production of foam |
JPH02281021A (en) * | 1989-04-21 | 1990-11-16 | Sanyo Chem Ind Ltd | Production of polymerized polyol composition and foam |
JPH0395212A (en) * | 1989-06-06 | 1991-04-19 | Tosoh Corp | Preparation of rigid polyurethane foam |
JPH0333120A (en) * | 1989-06-30 | 1991-02-13 | Tokyo Seat Kk | Production of molded urethane foam |
JPH03128913A (en) * | 1989-07-28 | 1991-05-31 | Tosoh Corp | Production of highly resilient polyurethane foam |
JPH03200825A (en) * | 1989-09-11 | 1991-09-02 | Tosoh Corp | Production of highly elastic polyurethane foam |
JPH03122108A (en) * | 1989-10-06 | 1991-05-24 | Tosoh Corp | Catalyst for producing polyurethane foam of spray type and production thereof using the same catalyst |
JPH03131618A (en) * | 1989-10-18 | 1991-06-05 | Tosoh Corp | Catalyst for production of phenol-based urethane foam and production using the same catalyst |
JPH04227619A (en) * | 1990-04-11 | 1992-08-17 | Tosoh Corp | Production of flexible polyurethane foam excellent in gas diffusibility |
JPH04214712A (en) * | 1990-09-19 | 1992-08-05 | Tokyo Seat Kk | Production of molded product of urethane foam |
JPH04298519A (en) * | 1990-09-19 | 1992-10-22 | Tokyo Seat Kk | Production of molded urethane foam |
JPH04202215A (en) * | 1990-11-29 | 1992-07-23 | Tokyo Seat Kk | Production of urethane foam molding |
JPH08198933A (en) * | 1995-01-26 | 1996-08-06 | Nishikawa Kasei Co Ltd | Production of foamed rigid urethane molding having skin layer and interior automotive trim having the same molding |
JP2002338649A (en) * | 2001-05-22 | 2002-11-27 | Tosoh Corp | Catalyst for producing polyurethane resin and method for producing polyurethane resin |
EP1262500A1 (en) * | 2001-05-22 | 2002-12-04 | Tosoh Corporation | Catalyst for production of a polyurethane resin and method for producing a polyurethane resin |
US6723819B2 (en) | 2001-05-22 | 2004-04-20 | Tosoh Corporation | Catalyst for production of a polyurethane resin and method for producing a polyurethane resin |
US7064172B2 (en) | 2001-05-22 | 2006-06-20 | Tosoh Corporation | Catalyst for production of a polyurethane resin and method for producing a polyurethane resin |
JP4538985B2 (en) * | 2001-05-22 | 2010-09-08 | 東ソー株式会社 | Catalyst for producing polyurethane resin and method for producing polyurethane resin |
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