JPH1087782A - モノマートリイソシアネートから作成される低粘度ポリイソシアネート - Google Patents
モノマートリイソシアネートから作成される低粘度ポリイソシアネートInfo
- Publication number
- JPH1087782A JPH1087782A JP9236466A JP23646697A JPH1087782A JP H1087782 A JPH1087782 A JP H1087782A JP 9236466 A JP9236466 A JP 9236466A JP 23646697 A JP23646697 A JP 23646697A JP H1087782 A JPH1087782 A JP H1087782A
- Authority
- JP
- Japan
- Prior art keywords
- polyisocyanate
- polyisocyanates
- weight
- group
- diisocyanate
- 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.)
- Pending
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 80
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 80
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims abstract description 17
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000008199 coating composition Substances 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 abstract description 11
- 150000002513 isocyanates Chemical class 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 abstract description 11
- 239000007858 starting material Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000005442 diisocyanate group Chemical group 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000178 monomer Substances 0.000 description 9
- 238000005829 trimerization reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000012089 stop solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007863 gel particle Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- -1 aliphatic hydrocarbon radical Chemical class 0.000 description 4
- 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 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical class Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LODDFDHPSIYCTK-UHFFFAOYSA-N (2,4,6-trimethylphenyl)methanol Chemical compound CC1=CC(C)=C(CO)C(C)=C1 LODDFDHPSIYCTK-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- AFVMPODRAIDZQC-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)cyclopentane Chemical compound O=C=NCC1CCCC1N=C=O AFVMPODRAIDZQC-UHFFFAOYSA-N 0.000 description 1
- VLNDSAWYJSNKOU-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylcyclohexyl)methyl]-2-methylcyclohexane Chemical compound C1CC(N=C=O)C(C)CC1CC1CC(C)C(N=C=O)CC1 VLNDSAWYJSNKOU-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- MRPZLXMWCIWOGP-UHFFFAOYSA-N 2,3-dimethyl-n-phenylaniline Chemical group CC1=CC=CC(NC=2C=CC=CC=2)=C1C MRPZLXMWCIWOGP-UHFFFAOYSA-N 0.000 description 1
- PQSMEVPHTJECDZ-UHFFFAOYSA-N 2,3-dimethylheptan-2-ol Chemical compound CCCCC(C)C(C)(C)O PQSMEVPHTJECDZ-UHFFFAOYSA-N 0.000 description 1
- HSRLPPVMHQEAQO-UHFFFAOYSA-N 2,6,8-trimethylnonan-1-ol Chemical compound CC(C)CC(C)CCCC(C)CO HSRLPPVMHQEAQO-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- DLTWBMHADAJAAZ-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCCC1O DLTWBMHADAJAAZ-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical compound NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 description 1
- NZEBWPHHIQAVOH-UHFFFAOYSA-N 4-cyclohexylbutan-1-ol Chemical compound OCCCCC1CCCCC1 NZEBWPHHIQAVOH-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BHCFVCRRNLIOGM-UHFFFAOYSA-J C(CO)(=O)[O-].[Mo+4].C(CO)(=O)[O-].C(CO)(=O)[O-].C(CO)(=O)[O-] Chemical compound C(CO)(=O)[O-].[Mo+4].C(CO)(=O)[O-].C(CO)(=O)[O-].C(CO)(=O)[O-] BHCFVCRRNLIOGM-UHFFFAOYSA-J 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000805 Polyaspartic acid Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical class [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 1
- QQBWQAURZPGDOG-UHFFFAOYSA-N ethyl hexanoate;zinc Chemical class [Zn].CCCCCC(=O)OCC QQBWQAURZPGDOG-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- NGTGENGUUCHSLQ-UHFFFAOYSA-N n-heptan-2-ylidenehydroxylamine Chemical compound CCCCCC(C)=NO NGTGENGUUCHSLQ-UHFFFAOYSA-N 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 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 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000011592 zinc chloride Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C08G18/06—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
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
-
- 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
- C08G2150/00—Compositions for coatings
- C08G2150/90—Compositions for anticorrosive coatings
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)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/697,229 | 1996-08-21 | ||
| US08/697,229 US5714564A (en) | 1996-08-21 | 1996-08-21 | Low viscosity polyisocyanates prepared from monomeric triisocyanates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1087782A true JPH1087782A (ja) | 1998-04-07 |
| JPH1087782A5 JPH1087782A5 (enExample) | 2005-06-02 |
Family
ID=24800337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9236466A Pending JPH1087782A (ja) | 1996-08-21 | 1997-08-19 | モノマートリイソシアネートから作成される低粘度ポリイソシアネート |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5714564A (enExample) |
| EP (1) | EP0825216B1 (enExample) |
| JP (1) | JPH1087782A (enExample) |
| CA (1) | CA2211274C (enExample) |
| DE (1) | DE69727741T2 (enExample) |
| MX (1) | MX9706250A (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005154777A (ja) * | 2003-11-26 | 2005-06-16 | Bayer Material Science Llc | ブロック化ポリイソシアネート |
| WO2015133493A1 (ja) * | 2014-03-04 | 2015-09-11 | 三井化学株式会社 | ポリイソシアヌレート組成物およびその製造方法 |
| JP2015180722A (ja) * | 2014-03-04 | 2015-10-15 | 三井化学株式会社 | ポリイソシアヌレート組成物およびその製造方法 |
| WO2018070531A1 (ja) | 2016-10-14 | 2018-04-19 | 旭化成株式会社 | ポリイソシアネート混合物、塗料組成物及び塗膜 |
| JP2018062634A (ja) * | 2016-10-14 | 2018-04-19 | 旭化成株式会社 | ポリイソシアネート組成物、ブロックポリイソシアネート組成物、親水性ポリイソシアネート組成物、塗料組成物、及び塗膜 |
| US11021562B2 (en) | 2016-10-14 | 2021-06-01 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| JP2022107706A (ja) * | 2018-04-11 | 2022-07-22 | 旭化成株式会社 | 塗料組成物及び塗膜 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5869566A (en) * | 1997-09-24 | 1999-02-09 | Ppg Industries, Inc. | Rapid drying, isocyanate cured coating composition with improved adhesion |
| DE19828935A1 (de) * | 1998-06-29 | 1999-12-30 | Basf Ag | Hochviskose Polyisocyanate enthaltende Zusammensetzungen |
| US20070149750A1 (en) * | 2003-11-26 | 2007-06-28 | Bayer Materialscience Llc | Solid powder coating crosslinker |
| US20050113548A1 (en) * | 2003-11-26 | 2005-05-26 | Roesler Richard R. | Solid powder coating crosslinker |
| WO2018163953A1 (ja) * | 2017-03-07 | 2018-09-13 | 旭化成株式会社 | ポリアスパラティック塗料組成物、塗膜、及び塗装物品 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1112243A (en) * | 1978-09-08 | 1981-11-10 | Manfred Bock | Process for the preparation of polyisocyanates containing isocyanurate groups and the use thereof |
| JPS56127341A (en) * | 1980-03-11 | 1981-10-06 | Asahi Chem Ind Co Ltd | New aliphatic triisocyanate, its preparation and nonyellowing polyurethane resin hardener composed thereof |
| DE3100263A1 (de) * | 1981-01-08 | 1982-08-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung bei der herstellung von polyurethanen |
| US4412073A (en) * | 1981-02-03 | 1983-10-25 | Rhone-Poulenc Specialites Chimiques | Isocyanurate preparation by catalytic, aminosilyl initiated cyclotrimerization of isocyanates |
| GB2203159B (en) * | 1987-04-03 | 1990-12-12 | Asahi Chemical Ind | An isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition |
| US5124427A (en) * | 1991-01-22 | 1992-06-23 | Miles Inc. | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions |
| US5235018A (en) * | 1991-07-22 | 1993-08-10 | Miles Inc. | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions |
| US5208334A (en) * | 1991-07-22 | 1993-05-04 | Miles Inc. | Process for the production of polyisocyanates containing allophanate and isocyanurate groups |
| CA2072167C (en) * | 1991-07-22 | 2001-12-18 | Terry A. Potter | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions |
| EP0566037A2 (en) * | 1992-04-14 | 1993-10-20 | Takeda Chemical Industries, Ltd. | Polyisocyanates, their production and use |
| US5380792A (en) * | 1993-04-19 | 1995-01-10 | Miles Inc. | Two-component aqueous polyurethane dispersions having improved pot life and coatings prepared therefrom |
-
1996
- 1996-08-21 US US08/697,229 patent/US5714564A/en not_active Expired - Fee Related
-
1997
- 1997-07-23 CA CA002211274A patent/CA2211274C/en not_active Expired - Fee Related
- 1997-08-08 DE DE1997627741 patent/DE69727741T2/de not_active Expired - Lifetime
- 1997-08-08 EP EP97113723A patent/EP0825216B1/en not_active Expired - Lifetime
- 1997-08-15 MX MX9706250A patent/MX9706250A/es not_active IP Right Cessation
- 1997-08-19 JP JP9236466A patent/JPH1087782A/ja active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005154777A (ja) * | 2003-11-26 | 2005-06-16 | Bayer Material Science Llc | ブロック化ポリイソシアネート |
| WO2015133493A1 (ja) * | 2014-03-04 | 2015-09-11 | 三井化学株式会社 | ポリイソシアヌレート組成物およびその製造方法 |
| JP2015180722A (ja) * | 2014-03-04 | 2015-10-15 | 三井化学株式会社 | ポリイソシアヌレート組成物およびその製造方法 |
| CN114195971A (zh) * | 2016-10-14 | 2022-03-18 | 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 |
| JP2018062634A (ja) * | 2016-10-14 | 2018-04-19 | 旭化成株式会社 | ポリイソシアネート組成物、ブロックポリイソシアネート組成物、親水性ポリイソシアネート組成物、塗料組成物、及び塗膜 |
| EP3674341A1 (en) | 2016-10-14 | 2020-07-01 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate mixture, coating composition, and coating film |
| US11021562B2 (en) | 2016-10-14 | 2021-06-01 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| US11248084B2 (en) | 2016-10-14 | 2022-02-15 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate mixture, coating composition, and coating film |
| WO2018070531A1 (ja) | 2016-10-14 | 2018-04-19 | 旭化成株式会社 | ポリイソシアネート混合物、塗料組成物及び塗膜 |
| EP4122967A1 (en) | 2016-10-14 | 2023-01-25 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| EP4122966A1 (en) | 2016-10-14 | 2023-01-25 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| EP4122968A1 (en) | 2016-10-14 | 2023-01-25 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| EP4134384A1 (en) | 2016-10-14 | 2023-02-15 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| EP4137523A1 (en) | 2016-10-14 | 2023-02-22 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| CN114195971B (zh) * | 2016-10-14 | 2023-08-25 | 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 |
| JP2022107706A (ja) * | 2018-04-11 | 2022-07-22 | 旭化成株式会社 | 塗料組成物及び塗膜 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2211274C (en) | 2007-02-20 |
| MX9706250A (es) | 1998-02-28 |
| US5714564A (en) | 1998-02-03 |
| EP0825216B1 (en) | 2004-02-25 |
| EP0825216A3 (en) | 1998-05-20 |
| CA2211274A1 (en) | 1998-02-21 |
| DE69727741D1 (de) | 2004-04-01 |
| EP0825216A2 (en) | 1998-02-25 |
| DE69727741T2 (de) | 2005-01-13 |
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