CA1184333A - Solutions d'ethers-oxydes d'oligo-urethanes dans des polyethers polyols, et leur emploi pour l'obtention de mousses de polyurethane - Google Patents

Solutions d'ethers-oxydes d'oligo-urethanes dans des polyethers polyols, et leur emploi pour l'obtention de mousses de polyurethane

Info

Publication number: CA1184333A
Authority: CA; Canada
Prior art keywords: molecular weight; solutions; average molecular; relatively high; diols
Prior art date: 1982-04-14
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

CA000400951A

Other languages

English (en)

Inventor

Klaus Konig

Gernot Becker

Peter Seifert

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.)

Bayer AG

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.)

1982-04-14

Filing date

1982-04-14

Publication date

1985-03-19

1982-04-14 Application filed by Bayer AG filed Critical Bayer AG

1982-04-14 Priority to CA000400951A priority Critical patent/CA1184333A/fr

1985-03-19 Application granted granted Critical

1985-03-19 Publication of CA1184333A publication Critical patent/CA1184333A/fr

Status Expired legal-status Critical Current

Links

229920000570 polyether Polymers 0.000 title claims abstract description 35
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 34
238000004519 manufacturing process Methods 0.000 title claims abstract description 24
229920005862 polyol Polymers 0.000 title claims abstract description 24
150000003077 polyols Chemical class 0.000 title claims abstract description 22
239000011496 polyurethane foam Substances 0.000 title claims abstract description 15
238000000034 method Methods 0.000 title claims abstract description 13
230000008569 process Effects 0.000 title claims abstract description 13
229920005830 Polyurethane Foam Polymers 0.000 title abstract description 13
125000005442 diisocyanate group Chemical group 0.000 claims abstract description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
230000009975 flexible effect Effects 0.000 claims abstract description 17
150000002605 large molecules Chemical class 0.000 claims abstract description 9
239000005056 polyisocyanate Substances 0.000 claims abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
229920001228 polyisocyanate Polymers 0.000 claims abstract description 7
239000000654 additive Substances 0.000 claims abstract description 6
239000004604 Blowing Agent Substances 0.000 claims abstract description 5
239000003054 catalyst Substances 0.000 claims abstract description 5
239000007795 chemical reaction product Substances 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
150000003384 small molecules Chemical class 0.000 claims abstract description 4
239000006260 foam Substances 0.000 claims description 34
150000002009 diols Chemical class 0.000 claims description 18
229920001451 polypropylene glycol Polymers 0.000 claims description 6
235000010290 biphenyl Nutrition 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
125000006267 biphenyl group Chemical group 0.000 claims 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 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 3
230000002411 adverse Effects 0.000 abstract description 2
239000004872 foam stabilizing agent Substances 0.000 abstract 1
-1 stabili.zers Substances 0.000 description 15
229940052303 ethers for general anesthesia Drugs 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
238000005187 foaming Methods 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
239000000306 component Substances 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000007858 starting material Substances 0.000 description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
239000001294 propane Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003466 welding Methods 0.000 description 5
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000000465 moulding Methods 0.000 description 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
238000003475 lamination Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
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 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
239000012190 activator Substances 0.000 description 2
HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
239000002131 composite material Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
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 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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 1
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 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
KIDHWZJUCRJVML-UHFFFAOYSA-N Putrescine Natural products NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
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 1
229930006000 Sucrose Natural products 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
210000003850 cellular structure Anatomy 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
XJRAOMZCVTUHFI-UHFFFAOYSA-N isocyanic acid;methane Chemical class C.N=C=O.N=C=O XJRAOMZCVTUHFI-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 1
229920003987 resole Polymers 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 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
239000004753 textile Substances 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000400951A 1982-04-14 1982-04-14 Solutions d'ethers-oxydes d'oligo-urethanes dans des polyethers polyols, et leur emploi pour l'obtention de mousses de polyurethane Expired CA1184333A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000400951A CA1184333A (fr)	1982-04-14	1982-04-14	Solutions d'ethers-oxydes d'oligo-urethanes dans des polyethers polyols, et leur emploi pour l'obtention de mousses de polyurethane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000400951A CA1184333A (fr)	1982-04-14	1982-04-14	Solutions d'ethers-oxydes d'oligo-urethanes dans des polyethers polyols, et leur emploi pour l'obtention de mousses de polyurethane

Publications (1)

Publication Number	Publication Date
CA1184333A true CA1184333A (fr)	1985-03-19

Family

ID=4122574

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000400951A Expired CA1184333A (fr)	1982-04-14	1982-04-14	Solutions d'ethers-oxydes d'oligo-urethanes dans des polyethers polyols, et leur emploi pour l'obtention de mousses de polyurethane

Country Status (1)

Country	Link
CA (1)	CA1184333A (fr)

1982
- 1982-04-14 CA CA000400951A patent/CA1184333A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-03-20	MKEC	Expiry (correction)
2002-04-14	MKEX	Expiry
2023-09-21	MKEX	Expiry	Effective date: 20020414

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US4554340A (en)	1985-11-19	Homogeneous, storage-stable polyol compositions of high ethylene glycol content and their use for the production of polyurethanes
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