CA1115894A - Composition de polyurethane, et articles connexes - Google Patents

Composition de polyurethane, et articles connexes

Info

Publication number: CA1115894A
Authority: CA; Canada
Prior art keywords: ester; hydroxy; diisocyanate; castor oil; glycol
Prior art date: 1976-11-05
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

CA287,732A

Other languages

English (en)

Inventor

Thaddeus F. Kroplinski

Barton C. Case

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.)

NL Industries Inc

Original Assignee

NL Industries Inc

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.)

1976-11-05

Filing date

1977-09-28

Publication date

1982-01-05

1977-09-28 Application filed by NL Industries Inc filed Critical NL Industries Inc

1982-01-05 Application granted granted Critical

1982-01-05 Publication of CA1115894A publication Critical patent/CA1115894A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 37
229920002635 polyurethane Polymers 0.000 title claims abstract description 20
239000004814 polyurethane Substances 0.000 title claims abstract description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 37
150000002148 esters Chemical class 0.000 claims abstract description 33
239000002253 acid Substances 0.000 claims abstract description 24
125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
150000005846 sugar alcohols Polymers 0.000 claims abstract description 14
239000012510 hollow fiber Substances 0.000 claims abstract description 13
239000004593 Epoxy Substances 0.000 claims abstract description 11
125000003700 epoxy group Chemical group 0.000 claims abstract description 7
239000004359 castor oil Substances 0.000 claims description 30
235000019438 castor oil Nutrition 0.000 claims description 30
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 claims description 30
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
-1 alkyl glycol ester Chemical class 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 18
125000005442 diisocyanate group Chemical group 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
239000000835 fiber Substances 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 12
239000000047 product Substances 0.000 claims description 11
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
229920000728 polyester Polymers 0.000 claims description 10
229920001451 polypropylene glycol Polymers 0.000 claims description 9
239000012530 fluid Substances 0.000 claims description 8
XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical group CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 claims description 7
239000003431 cross linking reagent Substances 0.000 claims description 6
229920001281 polyalkylene Polymers 0.000 claims description 6
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
229920005862 polyol Polymers 0.000 claims description 5
230000001588 bifunctional effect Effects 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
150000005690 diesters Chemical class 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
150000005691 triesters Chemical class 0.000 claims description 3
VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
239000004615 ingredient Substances 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 description 2
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims 4
229960003656 ricinoleic acid Drugs 0.000 claims 4
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims 4
229940113165 trimethylolpropane Drugs 0.000 claims 3
125000002947 alkylene group Chemical group 0.000 claims 1
239000010696 ester oil Substances 0.000 claims 1
JZSMZIOJUHECHW-GTJZZHROSA-N 2-hydroxypropyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(C)O JZSMZIOJUHECHW-GTJZZHROSA-N 0.000 abstract description 5
229920001730 Moisture cure polyurethane Polymers 0.000 abstract 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
238000001723 curing Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
229920000642 polymer Polymers 0.000 description 13
238000000034 method Methods 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
238000004382 potting Methods 0.000 description 5
OOPJDNDUQDODHP-DPMBMXLASA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol (Z,12R)-12-hydroxyoctadec-9-enoic acid Chemical compound CCC(CO)(CO)CO.CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O OOPJDNDUQDODHP-DPMBMXLASA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PPPQBUGNGAYVEC-BUWKIYKJSA-N C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(O)C(CC)(CO)CO Chemical compound C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(O)C(CC)(CO)CO PPPQBUGNGAYVEC-BUWKIYKJSA-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
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000000502 dialysis Methods 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
229940114069 12-hydroxystearate Drugs 0.000 description 2
229940114072 12-hydroxystearic acid Drugs 0.000 description 2
JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 description 2
JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical compound CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 description 2
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HRZINFJOMOVTEW-UNTBIKODSA-N C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(O)C(C)(CO)CO Chemical compound C(CCCCCCCC=C/C[C@H](O)CCCCCC)(=O)O.C(O)C(C)(CO)CO HRZINFJOMOVTEW-UNTBIKODSA-N 0.000 description 2
MWULJNYMVKLVBC-DPMBMXLASA-N CC(O)COC(C)CO.CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O Chemical compound CC(O)COC(C)CO.CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O MWULJNYMVKLVBC-DPMBMXLASA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
LWVWRVPXEAYXDT-ZDKIGPTLSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(CO)(CO)CO LWVWRVPXEAYXDT-ZDKIGPTLSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
XMHIUKTWLZUKEX-UHFFFAOYSA-N n-hexacosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
229920006149 polyester-amide block copolymer Polymers 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000001223 reverse osmosis Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000108 ultra-filtration Methods 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
YKPXTMAQTAVHDA-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,3-diol Chemical compound CC1(O)CC(O)=CC=C1 YKPXTMAQTAVHDA-UHFFFAOYSA-N 0.000 description 1
QUYITUXSUUKIRL-ZDKIGPTLSA-N 2-(2-hydroxyethoxy)ethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCOCCO QUYITUXSUUKIRL-ZDKIGPTLSA-N 0.000 description 1
QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical group [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
HDIFHQMREAYYJW-XGXNLDPDSA-N Glyceryl Ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XGXNLDPDSA-N 0.000 description 1
101100168117 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-8 gene Proteins 0.000 description 1
108010011935 Poly 18 antigen Proteins 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
229920006311 Urethane elastomer Polymers 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
238000007872 degassing Methods 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000013007 heat curing Methods 0.000 description 1
TXCQISUTCGVHJZ-UHFFFAOYSA-N hexadecaneperoxoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCCCCCC(=O)OO TXCQISUTCGVHJZ-UHFFFAOYSA-N 0.000 description 1
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 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
229940051250 hexylene glycol Drugs 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000004950 naphthalene Chemical class 0.000 description 1
229940075566 naphthalene Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 description 1
QXWCSODZTTWWNT-UHFFFAOYSA-N propane;propane-1,2,3-triol Chemical compound CCC.OCC(O)CO QXWCSODZTTWWNT-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 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
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
- B01D63/02—Hollow fibre modules
- B01D63/021—Manufacturing thereof
- B01D63/022—Encapsulating hollow fibres
- B01D63/023—Encapsulating materials
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
Polyurethanes Or Polyureas (AREA)
Separation Using Semi-Permeable Membranes (AREA)

CA287,732A 1976-11-05 1977-09-28 Composition de polyurethane, et articles connexes Expired CA1115894A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US73938076A	1976-11-05	1976-11-05
US739,380		1976-11-05

Publications (1)

Publication Number	Publication Date
CA1115894A true CA1115894A (fr)	1982-01-05

Family

ID=24972021

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA287,732A Expired CA1115894A (fr)	1976-11-05	1977-09-28	Composition de polyurethane, et articles connexes

Country Status (10)

Country	Link
JP (1)	JPS5358599A (fr)
AU (1)	AU516475B2 (fr)
BE (1)	BE860451A (fr)
CA (1)	CA1115894A (fr)
DE (1)	DE2749491A1 (fr)
ES (1)	ES463841A1 (fr)
FR (2)	FR2378053A1 (fr)
GB (1)	GB1557895A (fr)
IT (1)	IT1115397B (fr)
NL (1)	NL7712189A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1114714B (it) *	1978-03-25	1986-01-27	Akzo Nv	Massa di incorporazione poliuretanica e relativo procedimento di produzione
US4256617A (en) *	1979-11-01	1981-03-17	Nl Industries, Inc.	Catalyzed non-toxic polyurethane forming compositions and separatory devices employing the same
DE3147025A1 (de) *	1981-11-27	1983-06-01	Akzo Gmbh, 5600 Wuppertal	Einbettmasse auf basis schnellreagierender polyurethan-giessharze
JPS60115616A (ja) *	1983-11-26	1985-06-22	Toyobo Co Ltd	熱可塑性ポリウレタン樹脂の製造法
DE3411361A1 (de) *	1984-03-28	1985-10-10	Akzo Gmbh, 5600 Wuppertal	Einbettmaterial, verfahren zu seiner herstellung und seine verwendung
DE3912531C2 (de) *	1989-04-17	1998-08-27	Basf Ag	Glasklare, heißdampfsterilisierbare, kompakte Polyurethan-Vergußmassen, Verfahren zu ihrer Herstellung und ihre Verwendung, insbesondere für medizinisch technische Artikel
DE3927244A1 (de) *	1989-08-18	1991-02-21	Basf Ag	Transparente, heissdampfsterilisierbare, kompakte polyurethan-vergussmassen, verfahren zu ihrer herstellung und ihre verwendung, insbesondere fuer medizinisch technische artikel
DE4134693A1 (de) *	1991-10-21	1993-04-22	Basf Ag	Transparente, heissdampfsterilisierbare, nicht zytotoxische, im wesentlichen kompakte polyurethan-vergussmassen, verfahren zu ihrer herstellung und ihre verwendung, insbesondere fuer medizinisch-technische artikel
WO2020004212A1 (fr) *	2018-06-26	2020-01-02	Nok株式会社	Procédé de production d'une membrane poreuse à fibres creuses pour humidification

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2772245A (en) *	1952-04-26	1956-11-27	Lockheed Aircraft Corp	Resilient cellular resin products
US3362921A (en) *	1965-03-24	1968-01-09	Baker Castor Oil Co	Novel elastomeric products obtained from prepolymer compositions
US3483150A (en) *	1967-02-15	1969-12-09	Arthur Ehrlich	Polyurethane prepolymers and elastomers
US3962094A (en) *	1973-09-18	1976-06-08	The Dow Chemical Company	Hollow fiber separatory device

1977
- 1977-09-28 CA CA287,732A patent/CA1115894A/fr not_active Expired
- 1977-09-28 IT IT2803377A patent/IT1115397B/it active
- 1977-09-30 AU AU29276/77A patent/AU516475B2/en not_active Expired
- 1977-10-26 FR FR7732334A patent/FR2378053A1/fr active Granted
- 1977-11-02 JP JP13095777A patent/JPS5358599A/ja active Pending
- 1977-11-03 BE BE182328A patent/BE860451A/fr not_active IP Right Cessation
- 1977-11-04 NL NL7712189A patent/NL7712189A/xx not_active Application Discontinuation
- 1977-11-04 ES ES463841A patent/ES463841A1/es not_active Expired
- 1977-11-04 GB GB4607077A patent/GB1557895A/en not_active Expired
- 1977-11-04 DE DE19772749491 patent/DE2749491A1/de not_active Withdrawn
1978
- 1978-03-30 FR FR7809269A patent/FR2377825A1/fr active Granted

Also Published As

Publication number	Publication date
BE860451A (fr)	1978-03-01
FR2378053B1 (fr)	1982-01-08
DE2749491A1 (de)	1978-05-18
IT1115397B (it)	1986-02-03
ES463841A1 (es)	1979-01-01
JPS5358599A (en)	1978-05-26
GB1557895A (en)	1979-12-12
FR2377825A1 (fr)	1978-08-18
AU2927677A (en)	1979-04-05
FR2377825B1 (fr)	1981-07-03
AU516475B2 (en)	1981-06-04
NL7712189A (nl)	1978-05-09
FR2378053A1 (fr)	1978-08-18

Publication	Publication Date	Title
US4170559A (en)	1979-10-09	Hollow fiber separatory device
DE69315073T2 (de)	1998-06-10	Polyurethan/polyharnstoff-elastomere
US5554709A (en)	1996-09-10	Moisture-curing alkoxysilane-terminated polyurethanes
DE3850496T2 (de)	1994-11-10	Polyurethanschaumstoffherstellung.
US3483150A (en)	1969-12-09	Polyurethane prepolymers and elastomers
US3345311A (en)	1967-10-03	Castor oil, diisocyanate and hydroxy aliphatic acid ester prepolymers and elastomeric products prepared therefrom
DE3626223A1 (de)	1988-02-04	Polyurethan-praepolymere auf basis oleochemischer polyole, ihre herstellung und verwendung
CA1115894A (fr)	1982-01-05	Composition de polyurethane, et articles connexes
US4895879A (en)	1990-01-23	Internal mold release compositions
EP0335664A2 (fr)	1989-10-04	Polyétheréthanes fluorés et les dispositifs médicaux à partir de ceux-ci
GB1558496A (en)	1980-01-03	Method for providing polymers with durable proberties
US3846351A (en)	1974-11-05	Secondary aromatic alkyl diamines as foam catalysts and chain extenders
CA2152846C (fr)	2002-08-13	Mousse plastique etanche a l'eau
EP0193791B1 (fr)	1989-07-26	Préparation de corps moulés non cellulaires
US4463155A (en)	1984-07-31	Polyether polyurethane elastomers
US4757096A (en)	1988-07-12	Polyurethane froth foams
DE1056367B (de)	1959-04-30	Verfahren zur Herstellung von gegebenenfalls verschaeumten elastomeren Polyurethanen
DE3138422A1 (de)	1983-04-14	Verfahren zur herstellung von zelligen polyurethan-elastomeren auf basis von 4,4'-diisocyanato-diphenylethan-1,2
DE69806893T2 (de)	2002-12-05	Elektrisch isolierende, vernetzende Polyurethan Zusammensetzung und daraus gefertigte elektrische oder elektronische Bauteile
JP3312393B2 (ja)	2002-08-05	ポリウレタン系エラストマー形成性組成物及びこれを用いた中空繊維結束剤
JPH02215822A (ja)	1990-08-28	シール材及び結束材用ポリウレタンエラストマーの製造方法
DE10259184B3 (de)	2004-09-09	Stabile Polyoldispersionen und daraus hergestellte Polyurethanformkörper und ihre Verwendung
JPS6335673B2 (fr)	1988-07-15
EP0512198A1 (fr)	1992-11-11	Résines de polyuréthane de base à haute performance
JP3650989B2 (ja)	2005-05-25	注型用ポリウレタン樹脂形成性組成物を用いたシール材

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Date	Code	Title	Description
1999-01-05	MKEX	Expiry