CA2244486C - Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation - Google Patents

Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation Download PDF

Info

Publication number: CA2244486C
Authority: CA; Canada
Prior art keywords: formula; catalyst; hdi; carbon atoms; nco
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 - Fee Related

Application number

CA002244486A

Other languages

English (en)

French (fr)

Other versions

CA2244486A1 (en

Inventor

Frank Richter

Carl-Gerd Dieris

Harald Mertes

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

1998-08-03

Publication date

2007-10-23

1998-08-03 Application filed by Bayer AG filed Critical Bayer AG

1999-02-06 Publication of CA2244486A1 publication Critical patent/CA2244486A1/en

2007-10-23 Application granted granted Critical

2007-10-23 Publication of CA2244486C publication Critical patent/CA2244486C/en

2018-08-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 60
230000008569 process Effects 0.000 title claims abstract description 55
239000005056 polyisocyanate Substances 0.000 title claims abstract description 45
229920001228 polyisocyanate Polymers 0.000 title claims abstract description 43
238000002360 preparation method Methods 0.000 title claims abstract description 18
PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 title claims description 35
239000003054 catalyst Substances 0.000 claims abstract description 61
238000006384 oligomerization reaction Methods 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
150000001768 cations Chemical class 0.000 claims abstract description 6
230000003606 oligomerizing effect Effects 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 9
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
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 group C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims 2
239000012948 isocyanate Substances 0.000 abstract description 24
150000002513 isocyanates Chemical class 0.000 abstract description 21
239000000047 product Substances 0.000 description 47
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 36
239000000243 solution Substances 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 24
238000005829 trimerization reaction Methods 0.000 description 23
239000013638 trimer Chemical group 0.000 description 21
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 18
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 17
239000000178 monomer Substances 0.000 description 16
229920005989 resin Polymers 0.000 description 16
239000011347 resin Substances 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 15
125000005442 diisocyanate group Chemical group 0.000 description 15
238000005755 formation reaction Methods 0.000 description 15
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
238000006555 catalytic reaction Methods 0.000 description 14
238000004821 distillation Methods 0.000 description 14
150000001718 carbodiimides Chemical class 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000010409 thin film Substances 0.000 description 11
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
229910002092 carbon dioxide Inorganic materials 0.000 description 10
238000003756 stirring Methods 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
-1 alkyl phosphines Chemical class 0.000 description 8
JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 7
230000008901 benefit Effects 0.000 description 7
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical class O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 7
125000001453 quaternary ammonium group Chemical group 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
150000002222 fluorine compounds Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000003860 storage Methods 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 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
238000004519 manufacturing process Methods 0.000 description 5
229910000073 phosphorus hydride Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 4
PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-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
239000003795 chemical substances by application Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000003973 paint Substances 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
239000012855 volatile organic compound Substances 0.000 description 4
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 3
241000551547 Dione <red algae> Species 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000013065 commercial product Substances 0.000 description 3
239000000306 component Substances 0.000 description 3
239000000539 dimer Substances 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 3
YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
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 2
101150041968 CDC13 gene Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000013543 active substance Substances 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
239000002981 blocking agent Substances 0.000 description 2
PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class 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
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
150000001805 chlorine compounds Chemical class 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
238000006471 dimerization reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000007863 gel particle Substances 0.000 description 2
238000007172 homogeneous catalysis Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 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
XMAXUBOLEVIRGX-UHFFFAOYSA-N phosphanium;fluoride Chemical class [F-].[PH4+] XMAXUBOLEVIRGX-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
238000010517 secondary reaction Methods 0.000 description 2
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
150000003673 urethanes Chemical class 0.000 description 2
229910009112 xH2O Inorganic materials 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
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound 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
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
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
239000007983 Tris buffer Substances 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
230000000274 adsorptive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 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
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
RQVPEOYSZICMEA-UHFFFAOYSA-M benzyl(trimethyl)azanium;fluoride;hydrate Chemical compound O.[F-].C[N+](C)(C)CC1=CC=CC=C1 RQVPEOYSZICMEA-UHFFFAOYSA-M 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development 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
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000010408 film Substances 0.000 description 1
238000001914 filtration Methods 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
239000007792 gaseous phase Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229960004592 isopropanol Drugs 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
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 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
SGWCNDDOFLBOQV-UHFFFAOYSA-N oxidanium;fluoride Chemical compound O.F SGWCNDDOFLBOQV-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000012071 phase Substances 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
159000000001 potassium salts Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux 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
230000002226 simultaneous effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
YEKUWOWHPVKTCQ-UHFFFAOYSA-M tetraethylazanium;fluoride;hydrate Chemical compound O.[F-].CC[N+](CC)(CC)CC YEKUWOWHPVKTCQ-UHFFFAOYSA-M 0.000 description 1
HQFTZNVQVRRDLN-UHFFFAOYSA-M tetramethylazanium;fluoride;tetrahydrate Chemical compound O.O.O.O.[F-].C[N+](C)(C)C HQFTZNVQVRRDLN-UHFFFAOYSA-M 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 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)

CA002244486A 1997-08-06 1998-08-03 Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation Expired - Fee Related CA2244486C (en)

Applications Claiming Priority (2)

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

Publications (2)

Publication Number	Publication Date
CA2244486A1 CA2244486A1 (en)	1999-02-06
CA2244486C true CA2244486C (en)	2007-10-23

Family

ID=7838165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002244486A Expired - Fee Related CA2244486C (en)	1997-08-06	1998-08-03	Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation

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)

Families Citing this family (93)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2187097T3 (es) *	1998-06-02	2003-05-16	Bayer Ag	Procedimiento para la preparacion de poliisocianatos que contienen grupos iminooxadiazindiona.
DE19853569A1 (de)	1998-11-20	2000-05-25	Bayer Ag	Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE10123419A1 (de)	2001-05-14	2002-11-21	Bayer Ag	Verfahren zur Herstellung von aliphatischen Polyisocyanaten mit Uretdion-Isocyanurat- sowie Iminooxadiazindionstruktur
DE10160305A1 (de) *	2001-12-07	2003-06-18	Degussa	Katalysatoren und Verfahren zur Herstellung von Isocyanuratgruppen enthaltenden Polyisocyanaten und deren Verwendung
DE10208396B4 (de)	2002-02-27	2006-05-18	Ivoclar Vivadent Ag	Dentalmaterialien auf der Basis von substituierten Iminooxadiazindion-Derivaten
DE10208395B4 (de) *	2002-02-27	2004-03-25	Ivoclar Vivadent Ag	(Meth)acrylatsubstituierte Iminooxadiazindion-Derivate
DE10322620A1 (de)	2003-05-20	2004-12-16	Bayer Materialscience Ag	Festkörperreiche Bindemittelkombinationen für kratzfeste Decklacke
DE10336184A1 (de) *	2003-08-07	2005-02-24	Bayer Materialscience Ag	Neue Katalysatoren für die selektive Isocyanatdimerisierung
DE10339912B4 (de)	2003-08-29	2016-07-21	Ivoclar Vivadent Ag	Dentale Beschichtungsmaterialien, deren Verwendung sowie Verfahren zur Beschichtung einer Substratoberfläche
DE102004048871A1 (de) *	2004-10-07	2006-04-13	Bayer Materialscience Ag	Verfahren zur Herstellung von Iminooxadiazindiongruppen aufweisenden Polyisocyanaten
DE102004056849A1 (de)	2004-11-25	2006-06-08	Bayer Materialscience Ag	Neue Polyisocyanatgemische, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Härterkomponente in Polyurethanlacken
WO2006063745A1 (de) *	2004-12-13	2006-06-22	Basf Aktiengesellschaft	Verfahren zur herstellung von vergilbungsarmen (cyclo)aliphatischen polyisocyanaten
KR100950884B1 (ko) *	2005-10-21	2010-04-06	아사히 가세이 케미칼즈 가부시키가이샤	고가교성, 저점도 폴리이소시아네이트 조성물 및 이를포함하는 코팅 조성물
WO2008116897A1 (de)	2007-03-27	2008-10-02	Basf Se	Verfahren zur herstellung von farblosen isocyanuraten von diisocyanaten
WO2009068492A2 (de)	2007-11-28	2009-06-04	Basf Se	Flüssige stabilisatormischung
US8119245B2 (en)	2008-02-05	2012-02-21	Bayer Materialscience Llc	Dual-cure coating compositions based on polyaspartates polyisocyanates and acrylate-containing compounds
US20090226644A1 (en)	2008-03-05	2009-09-10	Wylie Amy S	Gel coat compositions from acrylate-modified aspartates
US8969614B2 (en)	2008-10-22	2015-03-03	Basf Se	Method for producing colourless polyisocyanates
DE102008052765A1 (de)	2008-10-22	2010-04-29	Bayer Materialscience Ag	Feuchtigkeitshärtende Polyisocyanatmischungen
DE102009005712A1 (de)	2009-01-22	2010-07-29	Bayer Materialscience Ag	Polyurethanvergussmassen
DE102009007194A1 (de)	2009-02-03	2010-08-05	Bayer Materialscience Ag	Flexible Beschichtungen
DE102009007228A1 (de)	2009-02-03	2010-08-05	Bayer Materialscience Ag	Beschichtungen
DE102010031682A1 (de)	2010-07-20	2012-01-26	Bayer Materialscience Ag	Bindemittelkombinationen für konstruktive Trinkwasserrohrbeschichtungen
DE102010038845A1 (de)	2010-08-03	2012-02-09	Bayer Materialscience Aktiengesellschaft	Verfahren zur Herstellung von Polyisocyanaten und deren Verwendung
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JP6082404B2 (ja) *	2011-11-29	2017-02-15	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒＩｎｔｅｌｌｅｃｔｕａｌＰｒｏｐｅｒｔｙＧｍｂＨ	ポリイソシアネートの製造方法およびその使用
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US20160046756A1 (en)	2013-03-22	2016-02-18	Covestro Deutschland Ag	Process for preparing polyisocyanates and catalyst kit therefor
JP6329017B2 (ja) *	2013-06-28	2018-05-23	旭化成株式会社	ポリイソシアネート組成物
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EP2883895B1 (de)	2013-12-10	2017-09-13	Covestro Deutschland AG	Iminooxadiazindion-Polyisocyanate
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WO2016146574A1 (de)	2015-03-16	2016-09-22	Covestro Deutschland Ag	Polyisocyanatzusammensetzung auf basis von 1,5-pentamethylendiisocyanat
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CN107531875B (zh)	2015-04-21	2020-09-22	科思创德国股份有限公司	用于生产具有功能化表面的聚异氰脲酸酯塑料的方法
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EP3286240A1 (en) *	2015-04-21	2018-02-28	Covestro Deutschland AG	Solids based on polyisocvanurate polymers produced under adiabatic conditions
TW201704220A (zh)	2015-04-21	2017-02-01	科思創德意志股份有限公司	聚異氰尿酸酯聚合物及製造聚異氰尿酸酯聚合物之方法
US10167358B2 (en)	2015-08-17	2019-01-01	Covestro Deutschland Ag	Process for modifying isocyanates with use of cyclic ammonium salts as catalyst
ES2870027T3 (es)	2015-09-09	2021-10-26	Covestro Intellectual Property Gmbh & Co Kg	Recubrimientos acuosos de PU 2C resistentes a arañazos
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US9815739B2 (en)	2015-10-30	2017-11-14	Covestro Llc	Polyisocyanurate based cement for wellbore fluid loss prevention
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ES2823248T3 (es)	2016-10-18	2021-05-06	Covestro Intellectual Property Gmbh & Co Kg	Revestimientos duros con alta estabilidad química y mecánica
JP7216644B2 (ja)	2016-11-14	2023-02-01	コベストロ、ドイチュラント、アクチエンゲゼルシャフト	前駆体から物体を製造する方法、および付加製造法におけるラジカル架橋性樹脂の使用
WO2018095869A1 (de)	2016-11-22	2018-05-31	Basf Se	Verfahren zur herstellung von trimeren isocyanaten
CN110312747B (zh)	2017-02-22	2022-07-15	科思创德国股份有限公司	使用螺环铵盐作为催化剂至少改性五亚甲基二异氰酸酯的方法
EP3381962A1 (de)	2017-03-29	2018-10-03	Covestro Deutschland AG	Erzeugung von polyisocyanuratschichten durch getrennte auftragung von isocyanatkomponenten und katalysatoren
EP3421516A1 (de)	2017-06-28	2019-01-02	Covestro Deutschland AG	Gefärbte kunststoffe basierend auf vernetzten polyisocyanaten
EP3444288A1 (de)	2017-08-15	2019-02-20	Covestro Deutschland AG	Verfahren zur herstellung iminooxadiazindiongruppen enthaltender polyisocyanate unter verwendung von katalysatorenmischungen
WO2019061019A1 (en)	2017-09-26	2019-04-04	Covestro Deutschland Ag	TWO-COMPONENT SYSTEM FOR ELASTIC COATINGS
EP3743449B1 (de)	2017-11-14	2024-04-17	Covestro Deutschland AG	Halbzeuge basierend auf dualem vernetzungsmechanismus
JP2021507041A (ja)	2017-12-21	2021-02-22	コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏＤｅｕｔｓｃｈｌａｎｄＡｇ	ポリイソシアネートに基づく耐霜性接着剤
US11124672B2 (en)	2017-12-21	2021-09-21	Covestro Deutschland Ag	Frost-resistant water paints based on polyisocyanates
WO2019157625A1 (en)	2018-02-13	2019-08-22	Covestro Deutschland Ag	Aromatic polyisocyanates with a high solids content
JP7305366B2 (ja) *	2018-02-15	2023-07-10	旭化成株式会社	ポリイソシアネート組成物、塗料組成物、塗膜の製造方法及び塗膜
EP3794050A1 (de)	2018-05-17	2021-03-24	Covestro Intellectual Property GmbH & Co. KG	Verfahren zur herstellung von verbundwerkstoffen aus polyethylenfasern mit ultrahohem molekulargewicht und vernetzten polyisocyanaten
CN112204065B (zh)	2018-05-17	2023-03-28	科思创知识产权两合公司	制备多异氰酸酯聚合物和聚异氰脲酸酯塑料的方法
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WO2020079160A1 (de)	2018-10-19	2020-04-23	Covestro Deutschland Ag	Wasserfrei härtende klebstoffe auf polyisocyanatbasis
WO2020152107A1 (de)	2019-01-22	2020-07-30	Covestro Intellectual Property Gmbh & Co. Kg	Kompositwerkstoffe basierend auf urethan- und isocyanuratpolymeren mit dualer härtung
WO2020174009A1 (de)	2019-02-27	2020-09-03	Covestro Intellectual Property Gmbh & Co. Kg	Polyisocyanuratwerkstoffe als elektrovergussmassen
US10544158B1 (en)	2019-03-14	2020-01-28	Covestro Llc	Process for producing polycyclic polyether polyols
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US20220363809A1 (en) *	2019-07-08	2022-11-17	Covestro Intellectual Property Gmbh & Co. Kg	Polymerizable compositions for preparing polyisocyanurate-based plastics having extended worklife
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WO2022002787A1 (de)	2020-07-02	2022-01-06	Covestro Deutschland Ag	Beschichtungen aus polyisocyanuratbeschichtungen (rim) und deren anwendung in spritzgiessprozessen
KR102819495B1 (ko) *	2020-09-25	2025-06-11	완후아 케미컬 그룹 코., 엘티디	색도가 안정적인 이소시아누레이트-함유 폴리이소시아네이트 조성물 및 이의 제조방법
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WO2022184522A1 (de)	2021-03-02	2022-09-09	Basf Se	Wasseremulgierbare polyisocyanate mit verbesserten eigenschaften
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US20250019483A1 (en)	2021-11-16	2025-01-16	Basf Se	Preparation of polyisocyanates containing iminooxadiazinedione groups and their use
EP4198094A1 (de)	2021-12-20	2023-06-21	Covestro Deutschland AG	Mehrschichtaufbau auf metallischen untergründen basierend auf polyaspartatbeschichtungen
CN118613517A (zh)	2022-01-18	2024-09-06	巴斯夫欧洲公司	含有亚氨基噁二嗪二酮基团的多异氰酸酯的制备及其用途
EP4303246A1 (de)	2022-07-04	2024-01-10	Covestro Deutschland AG	Polyisocyanatgemisch
WO2024165361A1 (en)	2023-02-09	2024-08-15	Basf Se	Preparation of polyisocyanates containing iminooxadiazinedione groups and their use
EP4414400A1 (de)	2023-02-09	2024-08-14	Covestro Deutschland AG	Polyisocyanate mit verbesserten eigenschaften
EP4545579A1 (de)	2023-10-24	2025-04-30	Covestro Deutschland AG	Verfahren zur herstellung eines polyisocyanats auf basis von 1,5-pentamethylendiisocyanat

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3814167A1 (de) *	1988-04-27	1989-11-09	Bayer Ag	Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung
DE3827596A1 (de) *	1988-08-13	1990-02-15	Bayer Ag	Neue katalysatoren, ein verfahren zu ihrer hertstellung und ihre verwendung zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten
DE3902078A1 (de) *	1989-01-25	1990-07-26	Bayer Ag	Verfahren zur herstellung von modifizierten, isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung
JP3195787B2 (ja) *	1990-03-12	2001-08-06	旭電化工業株式会社	イソシアネート三量化またはウレタン化触媒
DE19611849A1 (de) *	1996-03-26	1997-10-02	Bayer Ag	Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung

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 DE DE59811531T patent/DE59811531D1/de not_active Expired - Lifetime
- 1998-07-24 EP EP98113848A patent/EP0896009B1/de not_active Expired - Lifetime
- 1998-07-24 AT AT98113848T patent/ATE268788T1/de not_active IP Right Cessation
- 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
DE19734048A1 (de)	1999-02-11
ES2222536T3 (es)	2005-02-01
KR19990023374A (ko)	1999-03-25
JPH11152320A (ja)	1999-06-08
ATE268788T1 (de)	2004-06-15
JP4106134B2 (ja)	2008-06-25
KR100511245B1 (ko)	2006-02-28
DE59811531D1 (de)	2004-07-15
CA2244486A1 (en)	1999-02-06
EP0896009A1 (de)	1999-02-10
EP0896009B1 (de)	2004-06-09

Legal Events

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2003-06-27	EEER	Examination request
2016-09-14	MKLA	Lapsed	Effective date: 20160803

Publication	Publication Date	Title
JP4106134B2 (ja)	2008-06-25	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
JPH11152320A5 (2)	2005-10-27
CA2200823C (en)	2005-10-04	Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use
CA1257593A (en)	1989-07-18	Process for the production of oligomeric polyisocyanates and their use in the production of polyurethane plastics
US4929724A (en)	1990-05-29	Process for the production of uretdione group-containing compounds, the compounds obtained according to this process and the use thereof in the production of polyurethane plastics material
US5013838A (en)	1991-05-07	Polyisocyanates containing isocyanurate groups and a process for their production
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CA2059338A1 (en)	1992-07-23	Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions
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MXPA98006311A (en)	1999-06-01	Polyisocianates containing iminooxadiazina diona groups and a procedure for preparing them
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