JP4106134B2 - イミノオキサジアジンジオン基を有するポリイソシアネートおよびその製造方法 - Google Patents

イミノオキサジアジンジオン基を有するポリイソシアネートおよびその製造方法 Download PDF

Info

Publication number: JP4106134B2
Authority: JP; Japan
Prior art keywords: catalyst; hdi; formula; viscosity; fluoride
Prior art date: 1997-08-06
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 - Lifetime

Application number

JP23111598A

Other languages

English (en)

Japanese (ja)

Other versions

JPH11152320A5 (2

JPH11152320A (ja

Inventor

フランク・リヒテル

カール−ゲルト・デイーリス

ハラルト・メルテス

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.)

1997-08-06

Filing date

1998-08-04

Publication date

2008-06-25

1998-08-04 Application filed by Bayer AG filed Critical Bayer AG

1999-06-08 Publication of JPH11152320A publication Critical patent/JPH11152320A/ja

2005-10-27 Publication of JPH11152320A5 publication Critical patent/JPH11152320A5/ja

2008-06-25 Application granted granted Critical

2008-06-25 Publication of JP4106134B2 publication Critical patent/JP4106134B2/ja

2018-08-04 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000005056 polyisocyanate Substances 0.000 title claims abstract description 42
229920001228 polyisocyanate Polymers 0.000 title claims abstract description 39
238000004519 manufacturing process Methods 0.000 title claims abstract description 16
PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 title claims description 30
239000003054 catalyst Substances 0.000 claims abstract description 59
238000000034 method Methods 0.000 claims abstract description 44
230000008569 process Effects 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
239000000178 monomer Substances 0.000 claims description 24
238000006384 oligomerization reaction Methods 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000001931 aliphatic group Chemical group 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 10
125000002723 alicyclic group Chemical group 0.000 claims description 6
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
239000012948 isocyanate Substances 0.000 abstract description 24
150000002513 isocyanates Chemical class 0.000 abstract description 22
150000001768 cations Chemical class 0.000 abstract description 5
229910052717 sulfur Inorganic materials 0.000 abstract description 3
125000005842 heteroatom Chemical group 0.000 abstract 2
125000004122 cyclic group Chemical group 0.000 abstract 1
239000000047 product Substances 0.000 description 46
239000005057 Hexamethylene diisocyanate Substances 0.000 description 40
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 24
239000000243 solution Substances 0.000 description 24
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 22
238000005829 trimerization reaction Methods 0.000 description 21
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 20
238000006555 catalytic reaction Methods 0.000 description 15
229920005989 resin Polymers 0.000 description 15
239000011347 resin Substances 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
150000001718 carbodiimides Chemical class 0.000 description 12
125000005442 diisocyanate group Chemical group 0.000 description 12
-1 tetraalkylammonium cation Chemical class 0.000 description 12
238000004821 distillation Methods 0.000 description 11
PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 10
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000010409 thin film Substances 0.000 description 10
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
239000006227 byproduct Substances 0.000 description 8
JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
229910002092 carbon dioxide Inorganic materials 0.000 description 7
HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 7
125000001453 quaternary ammonium group Chemical group 0.000 description 7
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 7
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
230000008901 benefit Effects 0.000 description 6
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
239000007789 gas Substances 0.000 description 5
229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
229910000073 phosphorus hydride Inorganic materials 0.000 description 5
238000002798 spectrophotometry method Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
238000000576 coating method Methods 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
238000003860 storage Methods 0.000 description 4
239000012855 volatile organic compound Substances 0.000 description 4
XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 3
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
FTECITCJOALIAZ-UHFFFAOYSA-N N(=C=O)CCCCCCN=C1C(C(N=NO1)=O)=O Chemical compound N(=C=O)CCCCCCN=C1C(C(N=NO1)=O)=O FTECITCJOALIAZ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000013065 commercial product Substances 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000003973 paint Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 2
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
239000000539 dimer Substances 0.000 description 2
238000006471 dimerization reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002222 fluorine compounds Chemical class 0.000 description 2
DVERFJXHCKPMNM-UHFFFAOYSA-N fluorophosphane Chemical compound PF DVERFJXHCKPMNM-UHFFFAOYSA-N 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000007863 gel particle Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000011527 polyurethane coating Substances 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
235000003270 potassium fluoride Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
YEKUWOWHPVKTCQ-UHFFFAOYSA-M tetraethylazanium;fluoride;hydrate Chemical compound O.[F-].CC[N+](CC)(CC)CC YEKUWOWHPVKTCQ-UHFFFAOYSA-M 0.000 description 2
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical class CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical class N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
HYMIXNCPVUJKPL-UHFFFAOYSA-N 3,5-dimethyl-6-methylimino-1,3,5-oxadiazinane-2,4-dione Chemical compound CN=C1OC(=O)N(C)C(=O)N1C HYMIXNCPVUJKPL-UHFFFAOYSA-N 0.000 description 1
FJGQGEBYYMLXFO-UHFFFAOYSA-N 3-methyl-6-methylimino-5-phenyl-1,3,5-oxadiazinane-2,4-dione Chemical compound CN=C1OC(=O)N(C)C(=O)N1C1=CC=CC=C1 FJGQGEBYYMLXFO-UHFFFAOYSA-N 0.000 description 1
VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
241001550224 Apha Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000010408 film Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
238000007172 homogeneous catalysis Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000005457 optimization Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
229920005749 polyurethane resin Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing 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
- C08G18/16—Catalysts
- 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polyurethanes Or Polyureas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP23111598A 1997-08-06 1998-08-04 イミノオキサジアジンジオン基を有するポリイソシアネートおよびその製造方法 Expired - Lifetime JP4106134B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19734048.2		1997-08-06
DE19734048A DE19734048A1 (de)	1997-08-06	1997-08-06	Verfahren zur Herstellung von Polyisocyanaten, damit hergestellte Polyisocyanate und deren Verwendung

Publications (3)

Publication Number	Publication Date
JPH11152320A JPH11152320A (ja)	1999-06-08
JPH11152320A5 JPH11152320A5 (2)	2005-10-27
JP4106134B2 true JP4106134B2 (ja)	2008-06-25

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JP23111598A Expired - Lifetime JP4106134B2 (ja)	1997-08-06	1998-08-04	イミノオキサジアジンジオン基を有するポリイソシアネートおよびその製造方法

Country Status (7)

Country	Link
EP (1)	EP0896009B1 (2)
JP (1)	JP4106134B2 (2)
KR (1)	KR100511245B1 (2)
AT (1)	ATE268788T1 (2)
CA (1)	CA2244486C (2)
DE (2)	DE19734048A1 (2)
ES (1)	ES2222536T3 (2)

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1997
- 1997-08-06 DE DE19734048A patent/DE19734048A1/de not_active Withdrawn
1998
- 1998-07-24 ES ES98113848T patent/ES2222536T3/es not_active Expired - Lifetime
- 1998-07-24 AT AT98113848T patent/ATE268788T1/de not_active IP Right Cessation
- 1998-07-24 EP EP98113848A patent/EP0896009B1/de not_active Expired - Lifetime
- 1998-07-24 DE DE59811531T patent/DE59811531D1/de not_active Expired - Lifetime
- 1998-08-03 CA CA002244486A patent/CA2244486C/en not_active Expired - Fee Related
- 1998-08-04 JP JP23111598A patent/JP4106134B2/ja not_active Expired - Lifetime
- 1998-08-05 KR KR1019980031861A patent/KR100511245B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2244486A1 (en)	1999-02-06
CA2244486C (en)	2007-10-23
DE19734048A1 (de)	1999-02-11
ES2222536T3 (es)	2005-02-01
EP0896009A1 (de)	1999-02-10
DE59811531D1 (de)	2004-07-15
ATE268788T1 (de)	2004-06-15
KR100511245B1 (ko)	2006-02-28
KR19990023374A (ko)	1999-03-25
EP0896009B1 (de)	2004-06-09
JPH11152320A (ja)	1999-06-08

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