DE19611849A1 - Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung - Google Patents
Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und VerwendungInfo
- Publication number
- DE19611849A1 DE19611849A1 DE19611849A DE19611849A DE19611849A1 DE 19611849 A1 DE19611849 A1 DE 19611849A1 DE 19611849 A DE19611849 A DE 19611849A DE 19611849 A DE19611849 A DE 19611849A DE 19611849 A1 DE19611849 A1 DE 19611849A1
- Authority
- DE
- Germany
- Prior art keywords
- mixtures
- trimers
- nco
- groups
- isocyanate
- Prior art date
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000013638 trimer Substances 0.000 title claims abstract description 48
- 239000012948 isocyanate Substances 0.000 title claims abstract description 41
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 45
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 21
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052796 boron Inorganic materials 0.000 claims abstract description 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 229910052718 tin Inorganic materials 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 24
- 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 14
- 229920003023 plastic Polymers 0.000 claims description 11
- 239000004033 plastic Substances 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
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- 239000004202 carbamide Substances 0.000 claims description 3
- 150000002222 fluorine compounds Chemical class 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 claims description 3
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 239000000539 dimer Substances 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 37
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 27
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000005442 diisocyanate group Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000004821 distillation Methods 0.000 description 11
- -1 6-isocyanatohexyl Chemical group 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
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- 239000002253 acid Substances 0.000 description 8
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
- 239000003973 paint 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
- 238000006555 catalytic reaction Methods 0.000 description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 6
- 238000003860 storage Methods 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000007789 gas Substances 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
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 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 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 238000004132 cross linking Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000006855 networking Effects 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 239000000654 additive Substances 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 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
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
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- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
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- 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
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-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
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- QDTSVCYLAYAFCJ-UHFFFAOYSA-N 1-(isocyanatomethyl)-1-methylcyclohexane Chemical compound O=C=NCC1(C)CCCCC1 QDTSVCYLAYAFCJ-UHFFFAOYSA-N 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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- DEDZSLCZHWTGOR-UHFFFAOYSA-N n-propylcyclohexane Natural products CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 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
- 230000000135 prohibitive effect Effects 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
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
- 230000008646 thermal stress Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000002966 varnish Substances 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
- 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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19611849A DE19611849A1 (de) | 1996-03-26 | 1996-03-26 | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
| DK97104221T DK0798299T3 (da) | 1996-03-26 | 1997-03-13 | Isocyanattrimerisator og isocyanattrimerisatblandinger, deres fremstilling og anvendelse |
| PT97104221T PT798299E (pt) | 1996-03-26 | 1997-03-13 | Trimerizados de isocianato e misturas de trimerizados de isocianatos sua preparacao e utilizacao |
| AT97104221T ATE248154T1 (de) | 1996-03-26 | 1997-03-13 | Isocyanattrimerisate und isocyanattrimerisatmischungen, deren herstellung und verwendung |
| EP97104221A EP0798299B1 (de) | 1996-03-26 | 1997-03-13 | Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
| DE59710635T DE59710635D1 (de) | 1996-03-26 | 1997-03-13 | Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
| ES97104221T ES2205081T3 (es) | 1996-03-26 | 1997-03-13 | Trimeros de isocianatos y mezclas de trimeros de isocianatos, su preparacion y su uso. |
| CA002200823A CA2200823C (en) | 1996-03-26 | 1997-03-24 | Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use |
| JP08723497A JP3995300B2 (ja) | 1996-03-26 | 1997-03-24 | イミノオキサジアジンジオン基を含むイソシアネート三量体、その製造及び使用 |
| MXPA/A/1997/002231A MXPA97002231A (en) | 1996-03-26 | 1997-03-25 | New traceres of isocyanate and mixes of traceros of isocyanate, its obtaining and emp |
| KR1019970010220A KR100453869B1 (ko) | 1996-03-26 | 1997-03-25 | 이미노옥사디아진디온기를함유하는이소시아네이트삼량체,그의제조방법및용도 |
| US08/822,072 US5914383A (en) | 1996-03-26 | 1997-04-30 | Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19611849A DE19611849A1 (de) | 1996-03-26 | 1996-03-26 | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19611849A1 true DE19611849A1 (de) | 1997-10-02 |
Family
ID=7789419
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611849A Withdrawn DE19611849A1 (de) | 1996-03-26 | 1996-03-26 | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
| DE59710635T Expired - Lifetime DE59710635D1 (de) | 1996-03-26 | 1997-03-13 | Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59710635T Expired - Lifetime DE59710635D1 (de) | 1996-03-26 | 1997-03-13 | Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5914383A (enExample) |
| EP (1) | EP0798299B1 (enExample) |
| JP (1) | JP3995300B2 (enExample) |
| KR (1) | KR100453869B1 (enExample) |
| AT (1) | ATE248154T1 (enExample) |
| CA (1) | CA2200823C (enExample) |
| DE (2) | DE19611849A1 (enExample) |
| DK (1) | DK0798299T3 (enExample) |
| ES (1) | ES2205081T3 (enExample) |
| PT (1) | PT798299E (enExample) |
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| EP0849268A1 (de) * | 1996-12-20 | 1998-06-24 | Bayer Ag | Polycyclische Iminooxadiazindione aus (cyclo)aliphatischen 1,4-Diisocyanaten |
| EP0978511A3 (de) * | 1998-08-07 | 2000-08-30 | Bayer Aktiengesellschaft | N,N'-disubstituierte N-(2-hydroxyalkyl)-Harnstoffe |
| DE10208396A1 (de) * | 2002-02-27 | 2003-09-25 | Ivoclar Vivadent Ag | Dentalmaterialien auf der Basis von substituierten Iminooxadiazindion-Derivaten |
| WO2008003282A1 (de) * | 2006-07-05 | 2008-01-10 | Isl-Chemie Gmbh & Co. Kg | In-mold-coating verfahren zur herstellung von formteilen unter verwendung wässriger 2-komponenten-lackformulierung |
| DE102007031594A1 (de) * | 2007-07-06 | 2009-01-08 | Basf Coatings Ag | Universeller Spotblender für Einkomponenten- und Zweikomponentenklarlacke |
| WO2010083024A2 (en) | 2009-01-14 | 2010-07-22 | Bayer Materialscience Llc | Long-fiber thermoset composite with low orange peel |
| EP2305727A1 (de) | 2009-10-05 | 2011-04-06 | Bayer MaterialScience AG | Neue 2K-PUR-Systeme |
| WO2013006609A2 (en) | 2011-07-06 | 2013-01-10 | Bayer Materialscience Llc | Waterborne polyurethane coating compositions |
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| WO2015158738A1 (en) | 2014-04-18 | 2015-10-22 | Lamberti Spa | Additive for inkjet inks |
| WO2016169895A1 (de) | 2015-04-21 | 2016-10-27 | Covestro Deutschland Ag | Polyisocyanatmischung auf basis von 1,5-diisocyanatopentan |
| WO2017162811A1 (de) | 2016-03-23 | 2017-09-28 | Covestro Deutschland Ag | Härtbare zusammensetzungen auf basis von alkoxysilangruppen-haltigen prepolymeren |
| WO2018186886A1 (en) | 2017-04-07 | 2018-10-11 | Covestro Llc | Processes for in-mold coating of polymer substrates |
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| EP3444288A1 (de) | 2017-08-15 | 2019-02-20 | Covestro Deutschland AG | Verfahren zur herstellung iminooxadiazindiongruppen enthaltender polyisocyanate unter verwendung von katalysatorenmischungen |
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| CN111793182A (zh) * | 2020-07-15 | 2020-10-20 | 万华化学集团股份有限公司 | 一种多异氰酸酯组合物 |
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| FR2777894B1 (fr) * | 1998-04-24 | 2001-06-22 | Rhodia Chimie Sa | Procede de preparation d'isocyanates polyfonctionnels tricondensats de faible viscosite |
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| CN100341860C (zh) | 2000-01-20 | 2007-10-10 | 罗狄亚化学公司 | 制备轻度着色的支化多异氰酸酯的方法及所得到的组合物 |
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| JPS579773A (en) * | 1980-06-23 | 1982-01-19 | Takeda Chem Ind Ltd | Production of polyisocyanate |
| DE3420114A1 (de) * | 1984-05-30 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von uretdiongruppen aufweisenden polyisocyanaten |
| EP0235388B1 (en) * | 1985-12-28 | 1989-11-08 | MITSUI TOATSU CHEMICALS, Inc. | Preparation process of heat-resistant polymers |
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| 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 |
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| DE19603736A1 (de) * | 1996-02-02 | 1997-08-07 | Bayer Ag | Niedrigviskose Polyisocyanatmischung |
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- 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
- 1997-03-13 ES ES97104221T patent/ES2205081T3/es not_active Expired - Lifetime
- 1997-03-13 DE DE59710635T patent/DE59710635D1/de not_active Expired - Lifetime
- 1997-03-13 EP EP97104221A patent/EP0798299B1/de not_active Expired - Lifetime
- 1997-03-24 CA CA002200823A patent/CA2200823C/en not_active Expired - Fee Related
- 1997-03-24 JP JP08723497A patent/JP3995300B2/ja not_active Expired - Lifetime
- 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
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|---|---|---|---|---|
| EP0849268A1 (de) * | 1996-12-20 | 1998-06-24 | Bayer Ag | Polycyclische Iminooxadiazindione aus (cyclo)aliphatischen 1,4-Diisocyanaten |
| US5882544A (en) * | 1996-12-20 | 1999-03-16 | Bayer Aktiengesellschaft | Polycyclic iminooxadiazinediones from (cyclo)aliphatic 1,4-diisocyanates |
| EP0978511A3 (de) * | 1998-08-07 | 2000-08-30 | Bayer Aktiengesellschaft | N,N'-disubstituierte N-(2-hydroxyalkyl)-Harnstoffe |
| DE10208396A1 (de) * | 2002-02-27 | 2003-09-25 | Ivoclar Vivadent Ag | Dentalmaterialien auf der Basis von substituierten Iminooxadiazindion-Derivaten |
| US6818725B2 (en) | 2002-02-27 | 2004-11-16 | Ivoclar Vivadent Ag | Dental materials based on substituted iminooxadiazine dione derivatives |
| DE10208396B4 (de) * | 2002-02-27 | 2006-05-18 | Ivoclar Vivadent Ag | Dentalmaterialien auf der Basis von substituierten Iminooxadiazindion-Derivaten |
| WO2008003282A1 (de) * | 2006-07-05 | 2008-01-10 | Isl-Chemie Gmbh & Co. Kg | In-mold-coating verfahren zur herstellung von formteilen unter verwendung wässriger 2-komponenten-lackformulierung |
| DE102007031594A1 (de) * | 2007-07-06 | 2009-01-08 | Basf Coatings Ag | Universeller Spotblender für Einkomponenten- und Zweikomponentenklarlacke |
| US10023684B2 (en) | 2007-07-06 | 2018-07-17 | Basf Coatings Gmbh | Universal spot blender for one-component and two-component clearcoatings |
| WO2010083024A2 (en) | 2009-01-14 | 2010-07-22 | Bayer Materialscience Llc | Long-fiber thermoset composite with low orange peel |
| EP2305727A1 (de) | 2009-10-05 | 2011-04-06 | Bayer MaterialScience AG | Neue 2K-PUR-Systeme |
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| WO2013006609A2 (en) | 2011-07-06 | 2013-01-10 | Bayer Materialscience Llc | Waterborne polyurethane coating compositions |
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| DE102011115062A1 (de) | 2011-10-07 | 2013-04-11 | Dreve Prodimed Gmbh | Rohling zur abtragenden Herstellung von Ohrpassstücken |
| WO2013050016A1 (de) | 2011-10-07 | 2013-04-11 | Dreve Prodimed Gmbh | Rohling zur abtragenden herstellung von ohrpassstücken |
| WO2015158738A1 (en) | 2014-04-18 | 2015-10-22 | Lamberti Spa | Additive for inkjet inks |
| WO2016169895A1 (de) | 2015-04-21 | 2016-10-27 | Covestro Deutschland Ag | Polyisocyanatmischung auf basis von 1,5-diisocyanatopentan |
| WO2017162811A1 (de) | 2016-03-23 | 2017-09-28 | Covestro Deutschland Ag | Härtbare zusammensetzungen auf basis von alkoxysilangruppen-haltigen prepolymeren |
| CN109843952A (zh) * | 2016-10-14 | 2019-06-04 | 旭化成株式会社 | 多异氰酸酯组合物、封端多异氰酸酯组合物、亲水性多异氰酸酯组合物、涂料组合物和涂膜 |
| CN109843952B (zh) * | 2016-10-14 | 2021-11-12 | 旭化成株式会社 | 多异氰酸酯组合物、封端多异氰酸酯组合物、亲水性多异氰酸酯组合物、涂料组合物和涂膜 |
| WO2018186886A1 (en) | 2017-04-07 | 2018-10-11 | Covestro Llc | Processes for in-mold coating of polymer substrates |
| WO2018194572A1 (en) | 2017-04-19 | 2018-10-25 | Covestro Llc | Relective coatings and in-mold processes for their application to polymer substrates |
| EP3444288A1 (de) | 2017-08-15 | 2019-02-20 | Covestro Deutschland AG | Verfahren zur herstellung iminooxadiazindiongruppen enthaltender polyisocyanate unter verwendung von katalysatorenmischungen |
| WO2019034660A1 (de) | 2017-08-15 | 2019-02-21 | Covestro Deutschland Ag | Verfahren zur herstellung iminooxadiazindiongruppen enthaltender polyisocyanate unter verwendung von katalysatorenmischungen |
| IT202000001963A1 (it) | 2020-01-31 | 2021-07-31 | Lamberti Spa | Metodo per rivestire un substrato mediante polimerizzazione a fascio di elettroni |
| WO2021152031A1 (en) | 2020-01-31 | 2021-08-05 | Lamberti Spa | Method of coating a substrate by electron beam curing |
| CN111793182A (zh) * | 2020-07-15 | 2020-10-20 | 万华化学集团股份有限公司 | 一种多异氰酸酯组合物 |
| CN111793182B (zh) * | 2020-07-15 | 2022-04-22 | 万华化学集团股份有限公司 | 一种多异氰酸酯组合物 |
| WO2025174788A1 (en) | 2024-02-13 | 2025-08-21 | Covestro Llc | Insert molding and in-mold coating over substrates with pressure sensitive elements |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100453869B1 (ko) | 2004-12-30 |
| MX9702231A (es) | 1997-09-30 |
| CA2200823A1 (en) | 1997-09-26 |
| DK0798299T3 (da) | 2003-12-01 |
| DE59710635D1 (de) | 2003-10-02 |
| ES2205081T3 (es) | 2004-05-01 |
| JPH09268212A (ja) | 1997-10-14 |
| JP3995300B2 (ja) | 2007-10-24 |
| PT798299E (pt) | 2004-01-30 |
| CA2200823C (en) | 2005-10-04 |
| ATE248154T1 (de) | 2003-09-15 |
| US5914383A (en) | 1999-06-22 |
| EP0798299A1 (de) | 1997-10-01 |
| KR970065526A (ko) | 1997-10-13 |
| EP0798299B1 (de) | 2003-08-27 |
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