CA2200823C - Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use - Google Patents

Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use Download PDF

Info

Publication number: CA2200823C
Authority: CA; Canada
Prior art keywords: isocyanate; trimers; groups; mole percent; polyisocyanate mixture
Prior art date: 1996-03-26
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

CA002200823A

Other languages

English (en)

French (fr)

Other versions

CA2200823A1 (en

Inventor

Frank Richter

Josef Pedain

Harald Mertes

Carl-Gerd Dieres

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.)

1996-03-26

Filing date

1997-03-24

Publication date

2005-10-04

1997-03-24 Application filed by Bayer AG filed Critical Bayer AG

1997-09-26 Publication of CA2200823A1 publication Critical patent/CA2200823A1/en

2005-10-04 Application granted granted Critical

2005-10-04 Publication of CA2200823C publication Critical patent/CA2200823C/en

2017-03-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000013638 trimer Substances 0.000 title claims abstract description 59
239000012948 isocyanate Substances 0.000 title claims abstract description 49
150000002513 isocyanates Chemical class 0.000 title claims abstract description 46
PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 title claims abstract description 19
238000002360 preparation method Methods 0.000 title claims abstract description 18
239000000203 mixture Substances 0.000 claims abstract description 71
239000005056 polyisocyanate Substances 0.000 claims abstract description 58
229920001228 polyisocyanate Polymers 0.000 claims abstract description 56
238000000034 method Methods 0.000 claims abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 17
-1 cycloaliphatic Chemical group 0.000 claims abstract description 16
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 15
230000008569 process Effects 0.000 claims abstract description 14
150000002466 imines Chemical class 0.000 claims abstract description 8
125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 7
239000002981 blocking agent Substances 0.000 claims abstract description 4
239000003054 catalyst Substances 0.000 claims description 28
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 25
238000005829 trimerization reaction Methods 0.000 claims description 19
PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 11
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 9
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 8
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
229920003023 plastic Polymers 0.000 abstract description 12
239000004033 plastic Substances 0.000 abstract description 12
239000008199 coating composition Substances 0.000 abstract description 7
239000000463 material Substances 0.000 abstract description 7
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239000004480 active ingredient Substances 0.000 abstract description 3
239000000853 adhesive Substances 0.000 abstract description 3
230000001070 adhesive effect Effects 0.000 abstract description 3
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239000000047 product Substances 0.000 description 37
239000005057 Hexamethylene diisocyanate Substances 0.000 description 27
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 24
125000005442 diisocyanate group Chemical group 0.000 description 17
239000000178 monomer Substances 0.000 description 13
238000004821 distillation Methods 0.000 description 12
239000000243 solution Substances 0.000 description 11
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KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
230000008901 benefit Effects 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
238000006555 catalytic reaction Methods 0.000 description 7
238000004132 cross linking Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 6
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239000004814 polyurethane Substances 0.000 description 6
229920002635 polyurethane Polymers 0.000 description 6
239000010409 thin film Substances 0.000 description 6
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 5
150000001718 carbodiimides Chemical class 0.000 description 5
239000007789 gas Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000002222 fluorine compounds Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000006384 oligomerization reaction Methods 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
239000002994 raw material Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
241000894007 species Species 0.000 description 3
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 2
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
PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 2
JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XPSNCMZQNFDTHC-UHFFFAOYSA-N N(=C=O)CCCCCCC=1C(N(N(OC1)CCCCCCN=C=O)CCCCCCN=C=O)=N Chemical compound N(=C=O)CCCCCCC=1C(N(N(OC1)CCCCCCN=C=O)CCCCCCN=C=O)=N XPSNCMZQNFDTHC-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000000274 adsorptive effect Effects 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000003426 co-catalyst Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000539 dimer Substances 0.000 description 2
238000006471 dimerization reaction Methods 0.000 description 2
238000010494 dissociation reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000010408 film Substances 0.000 description 2
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000123 paper Substances 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
239000011527 polyurethane coating Substances 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 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
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical class O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
UOLKUOBCZVAOEZ-UHFFFAOYSA-N 1,3-dimethyl-1-(methylcarbamoyl)urea Chemical compound CNC(=O)N(C)C(=O)NC UOLKUOBCZVAOEZ-UHFFFAOYSA-N 0.000 description 1
IQOIAHPAAZJVOX-UHFFFAOYSA-N 1-isocyanato-3-methoxypropane Chemical compound COCCCN=C=O IQOIAHPAAZJVOX-UHFFFAOYSA-N 0.000 description 1
DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical class CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical class CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000551547 Dione <red algae> Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
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239000007983 Tris buffer Substances 0.000 description 1
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235000019270 ammonium chloride Nutrition 0.000 description 1
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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
239000011230 binding agent Substances 0.000 description 1
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150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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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
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KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
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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
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238000007172 homogeneous catalysis Methods 0.000 description 1
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
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VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
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229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000002194 synthesizing effect Effects 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
239000004753 textile Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/32—Cyanuric acid; Isocyanuric acid
- 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
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7875—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (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)
Image Analysis (AREA)
Adhesives Or Adhesive Processes (AREA)

CA002200823A 1996-03-26 1997-03-24 Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use Expired - Fee Related CA2200823C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19611849.2		1996-03-26
DE19611849A DE19611849A1 (de)	1996-03-26	1996-03-26	Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung

Publications (2)

Publication Number	Publication Date
CA2200823A1 CA2200823A1 (en)	1997-09-26
CA2200823C true CA2200823C (en)	2005-10-04

Family

ID=7789419

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002200823A Expired - Fee Related CA2200823C (en)	1996-03-26	1997-03-24	Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use

Country Status (10)

Country	Link
US (1)	US5914383A (2)
EP (1)	EP0798299B1 (2)
JP (1)	JP3995300B2 (2)
KR (1)	KR100453869B1 (2)
AT (1)	ATE248154T1 (2)
CA (1)	CA2200823C (2)
DE (2)	DE19611849A1 (2)
DK (1)	DK0798299T3 (2)
ES (1)	ES2205081T3 (2)
PT (1)	PT798299E (2)

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- 1996-03-26 DE DE19611849A patent/DE19611849A1/de not_active Withdrawn
1997
- 1997-03-13 DE DE59710635T patent/DE59710635D1/de not_active Expired - Lifetime
- 1997-03-13 ES ES97104221T patent/ES2205081T3/es not_active Expired - Lifetime
- 1997-03-13 EP EP97104221A patent/EP0798299B1/de not_active Expired - Lifetime
- 1997-03-13 DK DK97104221T patent/DK0798299T3/da active
- 1997-03-13 AT AT97104221T patent/ATE248154T1/de active
- 1997-03-13 PT PT97104221T patent/PT798299E/pt unknown
- 1997-03-24 JP JP08723497A patent/JP3995300B2/ja not_active Expired - Lifetime
- 1997-03-24 CA CA002200823A patent/CA2200823C/en not_active Expired - Fee Related
- 1997-03-25 KR KR1019970010220A patent/KR100453869B1/ko not_active Expired - Lifetime
- 1997-04-30 US US08/822,072 patent/US5914383A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
KR970065526A (ko)	1997-10-13
JPH09268212A (ja)	1997-10-14
US5914383A (en)	1999-06-22
EP0798299B1 (de)	2003-08-27
DK0798299T3 (da)	2003-12-01
DE19611849A1 (de)	1997-10-02
JP3995300B2 (ja)	2007-10-24
DE59710635D1 (de)	2003-10-02
ES2205081T3 (es)	2004-05-01
MX9702231A (es)	1997-09-30
CA2200823A1 (en)	1997-09-26
ATE248154T1 (de)	2003-09-15
PT798299E (pt)	2004-01-30
EP0798299A1 (de)	1997-10-01
KR100453869B1 (ko)	2004-12-30

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2017-05-06	MKLA	Lapsed	Effective date: 20170324

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