HU191081B - Process for production of compositions consisting of izocyanurate-groups by means of cathalitic cyclotrimerization consisting of izocyanate aminosililgorups - Google Patents
Process for production of compositions consisting of izocyanurate-groups by means of cathalitic cyclotrimerization consisting of izocyanate aminosililgorups Download PDFInfo
- Publication number
- HU191081B HU191081B HU31582A HU31582A HU191081B HU 191081 B HU191081 B HU 191081B HU 31582 A HU31582 A HU 31582A HU 31582 A HU31582 A HU 31582A HU 191081 B HU191081 B HU 191081B
- Authority
- HU
- Hungary
- Prior art keywords
- isocyanate
- catalyst
- groups
- cyclotrimerization
- isocyanurate
- Prior art date
Links
- 238000006006 cyclotrimerization reaction Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000012948 isocyanate Substances 0.000 claims abstract description 105
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 86
- -1 aminosilyl Chemical group 0.000 claims abstract description 30
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims abstract description 25
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 25
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 25
- 230000003197 catalytic effect Effects 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000006555 catalytic reaction Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 88
- 238000006243 chemical reaction Methods 0.000 abstract description 56
- 125000001931 aliphatic group Chemical group 0.000 abstract description 12
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 239000003973 paint Substances 0.000 abstract description 3
- 230000006698 induction Effects 0.000 abstract description 2
- 239000002966 varnish Substances 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 48
- 239000005056 polyisocyanate Substances 0.000 description 26
- 229920001228 polyisocyanate Polymers 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 23
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 20
- 239000007983 Tris buffer Substances 0.000 description 15
- 229920000582 polyisocyanurate Polymers 0.000 description 15
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 9
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 9
- 239000011495 polyisocyanurate Substances 0.000 description 7
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- ZSMNRKGGHXLZEC-UHFFFAOYSA-N n,n-bis(trimethylsilyl)methanamine Chemical compound C[Si](C)(C)N(C)[Si](C)(C)C ZSMNRKGGHXLZEC-UHFFFAOYSA-N 0.000 description 5
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910014299 N-Si Inorganic materials 0.000 description 4
- KSFBTBXTZDJOHO-UHFFFAOYSA-N diaminosilicon Chemical compound N[Si]N KSFBTBXTZDJOHO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SWPKJPABFYFDNT-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-dimethylsilyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](C)(C)N(CCCC)CCCC SWPKJPABFYFDNT-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- UAHFGVALXLABJK-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazin-4-amine Chemical class NC1=NNNCC1 UAHFGVALXLABJK-UHFFFAOYSA-N 0.000 description 1
- XSJFAAMNRIJDGN-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclobutane Chemical compound O=C=NCC1CCC1CN=C=O XSJFAAMNRIJDGN-UHFFFAOYSA-N 0.000 description 1
- ODKSRULWLOLNJQ-UHFFFAOYSA-N 1,2-diisocyanatocyclohexane Chemical compound O=C=NC1CCCCC1N=C=O ODKSRULWLOLNJQ-UHFFFAOYSA-N 0.000 description 1
- YEACGXMAEGBJSM-UHFFFAOYSA-N 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(C=2C=CC=CC=2)C(=O)N(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1 YEACGXMAEGBJSM-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- XBHIDEXFAORHCC-UHFFFAOYSA-N 1-butyl-1,3-dimethyl-3-trimethylsilylurea Chemical compound CCCCN(C)C(=O)N(C)[Si](C)(C)C XBHIDEXFAORHCC-UHFFFAOYSA-N 0.000 description 1
- RYYACEQMZMUAGS-UHFFFAOYSA-N 1-ethyl-3,3-dimethyl-1-trimethylsilylurea Chemical compound CCN([Si](C)(C)C)C(=O)N(C)C RYYACEQMZMUAGS-UHFFFAOYSA-N 0.000 description 1
- DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- JNGBRJRDAFRXBY-UHFFFAOYSA-N C[Si](C1=C(N(CCCC)CCCC)C=CC=C1)(C)C Chemical compound C[Si](C1=C(N(CCCC)CCCC)C=CC=C1)(C)C JNGBRJRDAFRXBY-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 101100477602 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SIR3 gene Proteins 0.000 description 1
- 229910007991 Si-N Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910006294 Si—N Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical class N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 1
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical class N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 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
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- OGWVYCFORNDBRE-UHFFFAOYSA-N n,n-bis(trimethylsilyl)ethanamine Chemical compound CCN([Si](C)(C)C)[Si](C)(C)C OGWVYCFORNDBRE-UHFFFAOYSA-N 0.000 description 1
- XIFOKLGEKUNZTI-UHFFFAOYSA-N n-[diethylamino(dimethyl)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](C)(C)N(CC)CC XIFOKLGEKUNZTI-UHFFFAOYSA-N 0.000 description 1
- IOTFVZVUTVVOER-UHFFFAOYSA-N n-[dimethyl(phenyl)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](C)(C)C1=CC=CC=C1 IOTFVZVUTVVOER-UHFFFAOYSA-N 0.000 description 1
- QULMGWCCKILBTO-UHFFFAOYSA-N n-[dimethylamino(dimethyl)silyl]-n-methylmethanamine Chemical compound CN(C)[Si](C)(C)N(C)C QULMGWCCKILBTO-UHFFFAOYSA-N 0.000 description 1
- WJBNXEUDLVCWBD-UHFFFAOYSA-N n-trimethylsilylbutan-1-amine Chemical compound CCCCN[Si](C)(C)C WJBNXEUDLVCWBD-UHFFFAOYSA-N 0.000 description 1
- HFZCSLHSASWKBB-UHFFFAOYSA-N n-trimethylsilylcyclohexanamine Chemical compound C[Si](C)(C)NC1CCCCC1 HFZCSLHSASWKBB-UHFFFAOYSA-N 0.000 description 1
- DUZKCWBZZYODQJ-UHFFFAOYSA-N n-trimethylsilylmethanamine Chemical compound CN[Si](C)(C)C DUZKCWBZZYODQJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001706 oxygenating effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—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
- 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
- C07D251/34—Cyanuric or isocyanuric esters
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8102192A FR2499085A1 (fr) | 1981-02-03 | 1981-02-03 | Procede d'obtention de composes a groupement isocyanurique par cyclotrimerisation catalytique d'isocyanate a l'aide de silazane-isocyanurates obtenus par la mise en oeuvre du procede |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU191081B true HU191081B (en) | 1987-01-28 |
Family
ID=9254852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU31582A HU191081B (en) | 1981-02-03 | 1982-02-02 | Process for production of compositions consisting of izocyanurate-groups by means of cathalitic cyclotrimerization consisting of izocyanate aminosililgorups |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS57150677A (enrdf_load_stackoverflow) |
| FR (1) | FR2499085A1 (enrdf_load_stackoverflow) |
| HU (1) | HU191081B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2818976B1 (fr) * | 2000-12-29 | 2005-04-15 | Rhodia Chimie Sa | Procede de (cyclo) condensation au moyen d'un sel de silazane d'erbium |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH422781A (de) * | 1962-12-13 | 1966-10-31 | Monsanto Co | Verfahren zur Herstellung von Silicium enthaltenden heterocyclischen Triisocyanaten |
| US3337510A (en) * | 1964-05-28 | 1967-08-22 | Gen Electric | Organosilicon compositions and methods for preparing the same |
-
1981
- 1981-02-03 FR FR8102192A patent/FR2499085A1/fr active Granted
-
1982
- 1982-02-02 HU HU31582A patent/HU191081B/hu not_active IP Right Cessation
- 1982-02-02 JP JP57014432A patent/JPS57150677A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2499085A1 (fr) | 1982-08-06 |
| JPS57150677A (en) | 1982-09-17 |
| FR2499085B1 (enrdf_load_stackoverflow) | 1983-03-11 |
| JPH0128747B2 (enrdf_load_stackoverflow) | 1989-06-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR890000379B1 (ko) | 이소시아네이트의 촉매적 시클로트리머화 반응에 의한 이소시아누레이트기 함유 화합물의 제법 | |
| JP2832473B2 (ja) | イソシアヌレート基含有ポリイソシアネートの製造方法 | |
| US4929724A (en) | 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 | |
| US5208334A (en) | Process for the production of polyisocyanates containing allophanate and isocyanurate groups | |
| EP0496208B1 (en) | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions | |
| US5914383A (en) | Isocyanate trimers containing iminooxadiazine dione groups, their preparation and use | |
| EP0524501B1 (en) | A process for the production of polyisocyanates containing allophanate and isocyanurate groups | |
| EP0524500B1 (en) | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and two-component coating compositions | |
| US5235018A (en) | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions | |
| US5444146A (en) | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions | |
| US4697014A (en) | Catalytic partial cyclotrimerization of polyisocyanates and product thereof | |
| JPS6322214B2 (enrdf_load_stackoverflow) | ||
| JPH01160960A (ja) | 脂肪族ウレトジオンの製法 | |
| US20030135007A1 (en) | Catalysts for preparing polyisocyanates containing isocyanurate groups, and their use | |
| CA2181640C (en) | Process for the production of polyisocyanates containing isocyanurate groups from aliphatic and aromatic isocyanate compounds | |
| KR100803890B1 (ko) | 알콕시실란 관능기를 갖는 뷰렛 및 이소시아네이트의 합성,그를 함유하는 제형물 및 그의 용도 | |
| KR100589891B1 (ko) | 저점도 3중축합 다관능성 이소시아네이트의 제조 방법 | |
| HU191081B (en) | Process for production of compositions consisting of izocyanurate-groups by means of cathalitic cyclotrimerization consisting of izocyanate aminosililgorups | |
| JPS62153277A (ja) | イソシアヌレ−ト基を含むポリイソシアネ−トの製造方法およびポリイソシアネ−ト重付加生成物製造への使用 | |
| US3320184A (en) | Silicon-containing polyisocyanates | |
| US3621020A (en) | Process for trimerizing polyisocyanates | |
| US6946538B2 (en) | Catalyst for isocyanate condensation, composition containing same, method for use, and resulting compositions | |
| JP2003267981A (ja) | 触媒及びイソシアヌレート基含有ポリイソシアネートの製法及びその使用 | |
| JP2960367B2 (ja) | ポリイソシアナト−イソシアヌレート及びその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |