CH626899A5 - Process for the preparation of foams containing urethane and isocyanurate groups - Google Patents

Process for the preparation of foams containing urethane and isocyanurate groups Download PDF

Info

Publication number: CH626899A5
Authority: CH; Switzerland
Prior art keywords: acid; groups; glycol; compounds; weight
Prior art date: 1976-02-27

Application number

CH233877A

Other languages

German (de)

English (en)

Inventor

Rolf Dr Wiedermann

Wolfgang Schmitz

Franz-Josef Bilstein

Original Assignee

Bayer Ag

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.)

1976-02-27

Filing date

1977-02-24

Publication date

1981-12-15

1977-02-24 Application filed by Bayer Ag filed Critical Bayer Ag

1981-12-15 Publication of CH626899A5 publication Critical patent/CH626899A5/de

Links

238000000034 method Methods 0.000 title description 29
239000006260 foam Substances 0.000 title description 20
230000008569 process Effects 0.000 title description 20
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 title description 8
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title description 7
238000002360 preparation method Methods 0.000 title description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 46
239000002253 acid Substances 0.000 description 31
239000003054 catalyst Substances 0.000 description 24
229920001228 polyisocyanate Polymers 0.000 description 22
239000005056 polyisocyanate Substances 0.000 description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
239000000203 mixture Substances 0.000 description 17
-1 alkali metal salt Chemical class 0.000 description 16
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 16
239000012948 isocyanate Substances 0.000 description 16
150000001875 compounds Chemical class 0.000 description 15
150000002513 isocyanates Chemical class 0.000 description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
229920000728 polyester Polymers 0.000 description 13
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 10
229920000570 polyether Polymers 0.000 description 10
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
235000014113 dietary fatty acids Nutrition 0.000 description 9
229930195729 fatty acid Natural products 0.000 description 9
239000000194 fatty acid Substances 0.000 description 9
150000004665 fatty acids Chemical class 0.000 description 9
150000007513 acids Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
150000001735 carboxylic acids Chemical class 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
238000005829 trimerization reaction Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
238000005187 foaming Methods 0.000 description 6
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
229920006295 polythiol Polymers 0.000 description 5
235000011056 potassium acetate Nutrition 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
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 4
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
239000004604 Blowing Agent Substances 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
239000005642 Oleic acid Substances 0.000 description 4
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000003513 alkali Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000004872 foam stabilizing agent Substances 0.000 description 4
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000004033 plastic Substances 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
239000004721 Polyphenylene oxide Substances 0.000 description 3
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
239000001361 adipic acid Substances 0.000 description 3
235000011037 adipic acid Nutrition 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002894 organic compounds Chemical class 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920005903 polyol mixture Polymers 0.000 description 3
229920006324 polyoxymethylene Polymers 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
229940029284 trichlorofluoromethane Drugs 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
230000009471 action Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000022 bacteriostatic agent Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
230000008859 change Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000010276 construction Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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239000000975 dye Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000003063 flame retardant Substances 0.000 description 2
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
230000001408 fungistatic effect Effects 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
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FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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150000002924 oxiranes Chemical class 0.000 description 2
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239000004417 polycarbonate Substances 0.000 description 2
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230000009257 reactivity Effects 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
150000003606 tin compounds Chemical class 0.000 description 2
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
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 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229960001147 triclofos Drugs 0.000 description 2
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
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229950006389 thiodiglycol Drugs 0.000 description 1
SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/089—Reaction retarding agents

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)
Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

CH233877A 1976-02-27 1977-02-24 Process for the preparation of foams containing urethane and isocyanurate groups CH626899A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762607999 DE2607999C2 (de)	1976-02-27	1976-02-27	Urethan- und Isocyanuratgruppen aufweisende Schaumstoffe und ein Verfahren zu ihrer Herstellung

Publications (1)

Publication Number	Publication Date
CH626899A5 true CH626899A5 (en)	1981-12-15

Family

ID=5971026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH233877A CH626899A5 (en)	1976-02-27	1977-02-24	Process for the preparation of foams containing urethane and isocyanurate groups

Country Status (7)

Country	Link
AT (1)	AT370428B (it)
BE (1)	BE851831A (it)
CH (1)	CH626899A5 (it)
DE (1)	DE2607999C2 (it)
FR (1)	FR2342309A1 (it)
GB (1)	GB1534236A (it)
IT (1)	IT1105702B (it)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1189249A (en) *	1981-07-09	1985-06-18	Bernhard Liessem	Foam manufacture
DE3227489A1 (de) *	1982-07-23	1984-01-26	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung als isocyanatkomponente zur herstellung von polyurethanen
GB2193504A (en) *	1986-07-24	1988-02-10	Basf Corp	Utilization of lactones and lactams in the preparation of polyurethane-polyurea microcellular foams
US4757095A (en) *	1986-07-24	1988-07-12	Basf Corporation	Utilization of lactones and lactams in the preparation of polyurethane-polyurea products
GB8822916D0 (en) *	1988-09-29	1988-11-02	Bp Chem Int Ltd	Process of preparing polyurea/polyurethane/urea foams
BR9003472A (pt) *	1989-07-19	1991-08-27	Dow Chemical Co	Espuma de poliuretana-poliisocianurato rigida e processo para preparar uma espuma de poliuretana-poliisocianurato rigida
DE4028211A1 (de) *	1990-09-06	1992-03-12	Basf Ag	Verfahren zur herstellung von urethangruppen oder urethan- und isocyanuratgruppen enthaltenden hartschaumstoffen
US5527876A (en) *	1992-01-31	1996-06-18	Henkel Kommanditgesellschaft Auf Aktien	Process for the production of plastics containing amide groups
DE4315874A1 (de) *	1993-05-12	1994-11-17	Basf Ag	Verfahren zur Herstellung von Polyurethan-Schaumstoffen
ES2149580T3 (es)	1996-11-04	2000-11-01	Huntsman Ici Chem Llc	Espumas rigidas de poliuretano.
EP0935625B1 (en)	1996-11-04	2001-06-27	Huntsman International Llc	Rigid polyurethane foams
HUE037988T2 (hu) *	2004-08-04	2018-09-28	Foam Supplies Inc	A reaktivitás idõbeli fennmaradása és a katalizátor lebomlása a poliuretán habban

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB802868A (en) *	1954-08-02	1958-10-15	Lockheed Aircraft Corp	Flexible resilient cellular resin products
DE1112285B (de) *	1959-01-17	1961-08-03	Bayer Ag	Verfahren zur Herstellung von Urethangruppen aufweisenden Schaumstoffen
GB893746A (en) *	1959-01-21	1962-04-11	Ici Ltd	Improvements in cellular polyurethanes
US3314834A (en) *	1962-12-14	1967-04-18	United Aircraft Corp	Method of pot life extension for polyurethane propellants
GB1083394A (en) *	1964-09-16	1967-09-13	Upjohn Co	Polyurethane foams
CH502399A (de) *	1967-03-24	1971-01-31	Mobay Chemical Corp	Verfahren zur Herstellung eines Isocyanuratgruppen aufweisenden Schaumstoffes, Mittel zur Durchführung des Verfahrens und so erhaltener Schaumstoff
FR1590004A (it) *	1968-10-25	1970-04-06
US3621020A (en) *	1969-12-17	1971-11-16	Du Pont	Process for trimerizing polyisocyanates
US3663465A (en) *	1970-01-29	1972-05-16	Du Pont	Preparation of open-cell polyurethane foams in the presence of 2-substituted 1,1,3,3-tetraalkyl guandines and an acid
GB1425929A (en) *	1972-12-06	1976-02-25	Dunlop Ltd	Polyurethane foams
DE2312678A1 (de) *	1973-03-14	1974-09-19	Bayer Ag	Verfahren zur herstellung von hydrophilen, elastischen polyurethanschaumstoffen

1976
- 1976-02-27 DE DE19762607999 patent/DE2607999C2/de not_active Expired
1977
- 1977-02-23 GB GB757477A patent/GB1534236A/en not_active Expired
- 1977-02-24 CH CH233877A patent/CH626899A5/de not_active IP Right Cessation
- 1977-02-25 IT IT4821877A patent/IT1105702B/it active
- 1977-02-25 BE BE175261A patent/BE851831A/xx not_active IP Right Cessation
- 1977-02-25 FR FR7705657A patent/FR2342309A1/fr active Granted
- 1977-02-25 AT AT129277A patent/AT370428B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB1534236A (en)	1978-11-29
DE2607999A1 (de)	1977-09-01
BE851831A (fr)	1977-08-25
FR2342309B1 (it)	1983-12-02
FR2342309A1 (fr)	1977-09-23
AT370428B (de)	1983-03-25
DE2607999C2 (de)	1983-02-03
IT1105702B (it)	1985-11-04
ATA129277A (de)	1982-08-15

Legal Events

Date	Code	Title	Description
1996-10-15	PL	Patent ceased

Publication	Publication Date	Title
EP0000389B1 (de)	1980-08-06	Verfahren zur Herstellung von Polyurethankunststoffen
DE2637170A1 (de)	1978-02-23	Verfahren zur herstellung von isocyanuratgruppen und urethangruppen aufweisenden kunststoffen
EP0007502B1 (de)	1981-12-30	Verfahren zur Herstellung von Formschaumstoffen
DE2513817C3 (de)	1986-11-13	Verfahren zur Herstellung von Schaumstoff-Formkörpern kompakter Randzone und zelligem Kern
DE3630225C2 (it)	1989-02-16
CH626899A5 (en)	1981-12-15	Process for the preparation of foams containing urethane and isocyanurate groups
DE2450540C2 (de)	1982-10-14	Hydroxylgruppenhaltige Kompositionen und ihre Verwendung zur Herstellung von flammwidrigen Kunststoffen
EP0025549B1 (de)	1983-03-09	Verfahren zur Herstellung von elastischen, flammkaschierbaren und hochfrequenzverschweissbaren Polyurethanschaumstoffen und die hierbei erhaltenen Produkte
DE2441843A1 (de)	1975-11-27	Verfahren zur herstellung von polyisocyanaten
DE2647482A1 (de)	1978-04-27	Verfahren zur herstellung von kalthaertenden, urethangruppen aufweisenden schaumstoffen
EP0243777A2 (de)	1987-11-04	Verfahren zur Herstellung von Polyharnstoffschaum-Formteilen
DE69522958T2 (de)	2002-03-28	Verfahren und zusammensetzungen zur herstellung von hartschaumstoffen mittels nicht-chlorfluorkohlenwasserstoff-treibmitteln
DE2340995A1 (de)	1975-02-27	Verfahren zur herstellung von polyurethanschaumstoffen
EP0077964B1 (de)	1986-07-02	Verfahren zur Herstellung von flammfesten, kaltzähen Polyurethanschaumstoffen und deren Verwendung als Innenauskleidung von Lagertanks
EP0000761B1 (de)	1981-11-25	Verfahren zur Herstellung von Urethangruppen aufweisenden Schaumstoffen
DE3430285A1 (de)	1986-02-27	Verwendung von 1-phosphonoethan- und/oder -propan-2-carbonsaeure-tri-c(pfeil abwaerts)1(pfeil abwaerts)-c(pfeil abwaerts)4(pfeil abwaerts)-alkylestern bei der herstellung von kunststoffen auf isocyanatbasis
EP0461072B1 (de)	1998-07-29	Verfahren zur Herstellung von Polyurethanstoffen unter Verwendung von spezifischen Stabilisatorsystemen
EP0199938A1 (de)	1986-11-05	Polyolkomposition und ihre Verwendung zur Herstellung von harten Polyurethan-Schaumstoffen
DE2459491A1 (de)	1976-06-24	Gegenueber isocyanaten reaktive phosphorhaltige flammschutzmittel
DE2343980A1 (de)	1975-04-17	Verfahren zur herstellung von kohlenstoffen, vorzugsweise kohlenstoff-schaumstoffen
DE2309861A1 (de)	1974-08-29	Verfahren zur herstellung von schaumstoff-formkoerpern
DE3323872A1 (de)	1985-01-03	Verfahren zur herstellung von elastischen, offenzelligen polyurethan-weichschaumstoffen mit raumgewichten von hoechstens 24 kg/m hoch 3
CH624340A5 (en)	1981-07-31	Process for the continuous extrusion of continuous profiles having a skin of thermoplastic and a foam core
DE2404310A1 (de)	1975-08-07	Verfahren zur herstellung von schaumstoffen
EP0171019B1 (de)	1989-08-16	Verfahren zur Herstellung von gegebenenfalls zellförmigen Polyurethanen