JP2008231149A - 触感塗料用組成物 - Google Patents
触感塗料用組成物 Download PDFInfo
- Publication number
- JP2008231149A JP2008231149A JP2007068528A JP2007068528A JP2008231149A JP 2008231149 A JP2008231149 A JP 2008231149A JP 2007068528 A JP2007068528 A JP 2007068528A JP 2007068528 A JP2007068528 A JP 2007068528A JP 2008231149 A JP2008231149 A JP 2008231149A
- Authority
- JP
- Japan
- Prior art keywords
- component
- composition
- polyols
- touch
- carbonate
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 239000011248 coating agent Substances 0.000 title abstract description 10
- 238000000576 coating method Methods 0.000 title abstract description 8
- 150000003077 polyols Chemical class 0.000 claims abstract description 28
- 229920005862 polyol Polymers 0.000 claims abstract description 26
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 13
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 9
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 239000003973 paint Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000010894 electron beam technology Methods 0.000 abstract description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 25
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- -1 fatty acid ester Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 230000035807 sensation Effects 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 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 5
- 239000000178 monomer Substances 0.000 description 5
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 210000003811 finger Anatomy 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 230000003655 tactile properties Effects 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- SLYBYYOFYNYTAY-UHFFFAOYSA-N (2-chloro-3-phenylphenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC(C=2C=CC=CC=2)=C1Cl SLYBYYOFYNYTAY-UHFFFAOYSA-N 0.000 description 1
- ZGSHFDSKHTZINF-UHFFFAOYSA-N (2-methyl-6-phenylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1OC(O)=O ZGSHFDSKHTZINF-UHFFFAOYSA-N 0.000 description 1
- BIQGQLXQLYTHRA-UHFFFAOYSA-N (2-phenylnaphthalen-1-yl) hydrogen carbonate Chemical compound C1=CC2=CC=CC=C2C(OC(=O)O)=C1C1=CC=CC=C1 BIQGQLXQLYTHRA-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-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
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- RWNJPRZBKSXYBL-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate;oxepan-2-one Chemical compound OCCOC(=O)C=C.O=C1CCCCCO1 RWNJPRZBKSXYBL-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-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
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- LJCTUEPREAVQFG-UHFFFAOYSA-N [4-methyl-3-(2-methylphenyl)phenyl] hydrogen carbonate Chemical compound CC1=CC=CC=C1C1=CC(OC(O)=O)=CC=C1C LJCTUEPREAVQFG-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UXXXZMDJQLPQPH-UHFFFAOYSA-N bis(2-methylpropyl) carbonate Chemical compound CC(C)COC(=O)OCC(C)C UXXXZMDJQLPQPH-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- HSNQKJVQUFYBBY-UHFFFAOYSA-N dipentyl carbonate Chemical compound CCCCCOC(=O)OCCCCC HSNQKJVQUFYBBY-UHFFFAOYSA-N 0.000 description 1
- JMPVESVJOFYWTB-UHFFFAOYSA-N dipropan-2-yl carbonate Chemical compound CC(C)OC(=O)OC(C)C JMPVESVJOFYWTB-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 210000004932 little finger Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000015541 sensory perception of touch Effects 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
【解決手段】一般式(1):CH2=CR1−COO−X1−O−(CO−X2−O)m−H(式中、R1は水素原子またはメチル基、X1は炭素数1〜4のアルキレン基、X2は分岐構造を有していてもよい炭素数3〜6のアルキレン基、mは1〜8の整数を表す。)で表される(メタ)アクリレート(a)を含有する(メタ)アクリレート類(A)、ポリオール類(B)およびイソシアヌレート構造を有するポリイソシアネート類(C)を反応させて得られるウレタンアクリレートを含有する触感塗料用組成物を用いる。
【選択図】なし
Description
攪拌機、温度計および冷却器を備えた1リットルの四つ口フラスコにポリ(3−メチルペンタンアジペート)ジオール(商品名:クラレポリオールP−2010、(株)クラレ製、数平均分子量2000)を1000g、イソホロンジイソシアネート74gを仕込み、攪拌しながら徐々に加熱を行った。反応による発熱状態に注意しながら、1.5時間をかけて80℃まで昇温し、80〜85℃で1時間保温後、オクチル酸第一スズ0.21g(200ppm)を添加し更に2時間保温した。IRで残存イソシアナート基が消失したことを確認した後に冷却し、淡黄色粘稠液体1074gを得た。これを樹脂B1とした。
製造例1と同様の反応装置にポリプロピレングリコール(商品名:アデカポリエーテルP−2000、(株)ADEKA製、数平均分子量2000)を1000g、イソホロンジイソシアネートを74g仕込み、製造例1と同様に反応を行い、淡黄色粘稠液体1074gを得た。これを樹脂B2とした。
製造例1と同様の反応装置にポリカーボネートジオール(商品名:クラレポリオールC−2090、(株)クラレ製、数平均分子量2000、)を1000g、イソホロンジイソシアネートを74g仕込み、製造例1と同様に反応を行い、淡黄色粘稠液体1074gを得た。これを樹脂B3とした。
製造例1と同様の反応装置に1,3,5−トリス(イソシアナートヘキシル)−1,3,5−トリアジン−2,4,6−(1H,3H,5H)トリオン(商品名:コロネートHX、日本ポリウレタン工業(株)製、イソシアナート基含有量21%)を150g、ε−カプロラクトン−β−ヒドロキシエチルアクリレート付加物(ヒドロキシエチルアクリレートのカプロラクトン4mol付加体、商品名:プラクセルFA−4、ダイセル化学工業(株)製)を259g、2−ヒドロキシエチルアクリレートを29g、樹脂B1を162g、4−メトキシフェノールを0.60g(1000ppm)を仕込み、攪拌しながら徐々に加熱を行った。反応による発熱状態に注意しながら、1.5時間をかけて75℃まで昇温し、75〜80℃で1時間保温後、オクチル酸第一スズ0.12g(200ppm)を添加し更に1時間保温した。IRで残存イソシアナート基が消失したことを確認した後に冷却し、淡黄色粘稠液体600gを得た。これを樹脂1とした。
製造例3における樹脂B1を樹脂B2に変更した以外は同様の反応を行い、淡黄色粘稠液体600gを得た。これを樹脂2とした。
製造例3における樹脂B1を樹脂B3に変更した以外は同様の反応を行い、淡黄色粘稠液体600gを得た。これを樹脂3とした。
製造例1と同様の装置にコロネートHXを230g、2−ヒドロキシエチルアクリレートを124g、樹脂B1を246g仕込み、製造例1と同様に反応を行い、淡黄色粘稠液体600gを得た。これを樹脂4とした。
製造例1と同様の装置にコロネートHXを380g、2−ヒドロキシエチルアクリレートを220g仕込み、製造例1と同様に反応を行い、淡黄色粘稠液体600gを得た。これを樹脂5とした。
製造例1で得られた樹脂1を50重量部、溶剤としてメチルエチルケトンを50重量部および光重合開始剤(商品名イルガキュアー184、チバ・スペシャルティ・ケミカルズ(株)製)を2.5重量部混合し、触感塗料組成物を調製し、以下の試験に供した。
樹脂1を樹脂2〜5に変えた他は実施例1と同様の組成物を混合し、触感塗料組成物を調製し、以下の試験に供した。
1.触感性試験
得られた試料をポリカーボネート板上にアプリケーターで乾燥膜厚20μm塗布し、80℃で2分乾燥させた。これに高圧水銀灯を照射して硬化させ(120W/cm×10cm(高さ)×1灯×10m/分×3パス)、これを硬化塗膜とした。触感性の判断は、硬化塗膜表面を指で触り、指の引っ掛り方でしっとり感を判定した。結果を表1に示す。
○・・・・・・指がかなり引っ掛るしっとりした触感。
△・・・・・・指が少し引っ掛るしっとりした触感。
×・・・・・・指が全く引っ掛らず、つるっとしており、しっとりした触感がない。
触感性試験と同じ硬化塗膜表面を爪先で強く擦り、その表面の傷付き性を目視判定した。結果を表1に示す。
○・・・・・・傷が全く残らない。
△・・・・・・傷がわずかに残る。
×・・・・・・傷がはっきり残る。
Claims (6)
- 一般式(1):CH2=CR1−COO−X1−O−(CO−X2−O)m−H(式中、R1は水素原子またはメチル基、X1は炭素数1〜4のアルキレン基、X2は分岐構造を有していてもよい炭素数3〜6のアルキレン基、mは1〜8の整数を表す。)で表される(メタ)アクリレート(a)を含有する(メタ)アクリレート類(A)、ポリオール類(B)およびイソシアヌレート構造を有するポリイソシアネート類(C)を反応させて得られるウレタンアクリレートを含有する触感塗料用組成物。
- ポリオール類(B)が、ポリエステルポリオール類、ポリエーテルポリオール類およびポリカーボネートポリオール類からなる群より選ばれる少なくとも1種のポリオール(b−1)とポリイソシアネート(b−2)を反応させて得られるポリオール(b)である請求項1記載の触感塗料用組成物。
- 一般式(1):CH2=CR1−COO−X1−O−(CO−X2−O)m−H(式中、R1は水素原子またはメチル基、X1は炭素数1〜4のアルキレン基、X2は分岐構造を有していてもよい炭素数3〜6のアルキレン基、mは1〜8の整数を表す。)で表される(メタ)アクリレート(a)を含有する(メタ)アクリレート類(A)、ポリオール類(B)およびイソシアヌレート構造を有するポリイソシアネート類(C)の使用量が、(A):(B):(C)が、2〜2.95:0.025〜0.5:1(モル比)である請求項1〜3のいずれかに記載の触感塗料用組成物。
- さらに反応性希釈剤(D)を含有する請求項1〜4のいずれかに記載の触感塗料用組成物。
- さらに光重合開始剤(E)を含有する請求項1〜5のいずれかに記載の触感塗料用組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007068528A JP5056092B2 (ja) | 2007-03-16 | 2007-03-16 | 触感塗料用組成物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007068528A JP5056092B2 (ja) | 2007-03-16 | 2007-03-16 | 触感塗料用組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008231149A true JP2008231149A (ja) | 2008-10-02 |
JP5056092B2 JP5056092B2 (ja) | 2012-10-24 |
Family
ID=39904351
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007068528A Expired - Fee Related JP5056092B2 (ja) | 2007-03-16 | 2007-03-16 | 触感塗料用組成物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5056092B2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104830218A (zh) * | 2014-06-25 | 2015-08-12 | Ppg涂料(天津)有限公司 | 具有优良弹性与改进的抗划伤性的柔软触感涂料组合物 |
CN105694698A (zh) * | 2014-12-12 | 2016-06-22 | 现代自动车株式会社 | 用于一涂一烘涂层的具有平滑结构的涂覆组合物 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02274713A (ja) * | 1989-04-18 | 1990-11-08 | Arakawa Chem Ind Co Ltd | 光硬化性樹脂 |
JPH0570534A (ja) * | 1991-09-10 | 1993-03-23 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化型樹脂調製物ならびに樹脂組成物 |
JP2003192751A (ja) * | 2001-12-27 | 2003-07-09 | Chugoku Marine Paints Ltd | 汚染除去性に優れた光硬化性(メタ)アクリレート系樹脂組成物、その被膜および被覆基材 |
JP2005336250A (ja) * | 2004-05-25 | 2005-12-08 | Dainippon Ink & Chem Inc | 木質材被覆用樹脂組成物 |
JP2008189774A (ja) * | 2007-02-02 | 2008-08-21 | Arakawa Chem Ind Co Ltd | 触感塗料組成物 |
JP2008222985A (ja) * | 2007-03-16 | 2008-09-25 | Nippon Shokubai Co Ltd | 活性エネルギー線硬化型樹脂組成物 |
-
2007
- 2007-03-16 JP JP2007068528A patent/JP5056092B2/ja not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02274713A (ja) * | 1989-04-18 | 1990-11-08 | Arakawa Chem Ind Co Ltd | 光硬化性樹脂 |
JPH0570534A (ja) * | 1991-09-10 | 1993-03-23 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化型樹脂調製物ならびに樹脂組成物 |
JP2003192751A (ja) * | 2001-12-27 | 2003-07-09 | Chugoku Marine Paints Ltd | 汚染除去性に優れた光硬化性(メタ)アクリレート系樹脂組成物、その被膜および被覆基材 |
JP2005336250A (ja) * | 2004-05-25 | 2005-12-08 | Dainippon Ink & Chem Inc | 木質材被覆用樹脂組成物 |
JP2008189774A (ja) * | 2007-02-02 | 2008-08-21 | Arakawa Chem Ind Co Ltd | 触感塗料組成物 |
JP2008222985A (ja) * | 2007-03-16 | 2008-09-25 | Nippon Shokubai Co Ltd | 活性エネルギー線硬化型樹脂組成物 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104830218A (zh) * | 2014-06-25 | 2015-08-12 | Ppg涂料(天津)有限公司 | 具有优良弹性与改进的抗划伤性的柔软触感涂料组合物 |
CN104830218B (zh) * | 2014-06-25 | 2017-05-24 | Ppg涂料(天津)有限公司 | 具有优良弹性与改进的抗划伤性的柔软触感涂料组合物 |
CN105694698A (zh) * | 2014-12-12 | 2016-06-22 | 现代自动车株式会社 | 用于一涂一烘涂层的具有平滑结构的涂覆组合物 |
JP2016113610A (ja) * | 2014-12-12 | 2016-06-23 | 現代自動車株式会社Hyundai Motor Company | 1回塗装用ソフトフィール塗料組成物 |
KR20160072346A (ko) * | 2014-12-12 | 2016-06-23 | 현대자동차주식회사 | 1회 도장용 질감도료 조성물 |
KR101704138B1 (ko) | 2014-12-12 | 2017-02-08 | 현대자동차주식회사 | 1회 도장용 질감도료 조성물 |
US9920158B2 (en) | 2014-12-12 | 2018-03-20 | Hyundai Motor Company | Coating composition having smooth texture for one-coat-one bake coating |
CN105694698B (zh) * | 2014-12-12 | 2018-12-18 | 现代自动车株式会社 | 用于一涂一烘涂层的具有平滑结构的涂覆组合物 |
Also Published As
Publication number | Publication date |
---|---|
JP5056092B2 (ja) | 2012-10-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6593290B2 (ja) | ポリカーボネートジオールの製造方法及びポリカーボネートジオール並びにそれを用いたポリウレタン | |
JP6178844B2 (ja) | ウレタン(メタ)アクリレート及び活性エネルギー線硬化型樹脂組成物 | |
JP7494887B2 (ja) | ポリカーボネートジオールおよびそれを用いた水系ポリウレタン分散体 | |
JP5568225B2 (ja) | 塗料 | |
JP7111155B2 (ja) | 光硬化性樹脂組成物及びそれを用いた粘接着剤 | |
JP5564949B2 (ja) | 硬化型組成物 | |
JP2019019304A (ja) | ポリカーボネートポリオール及びポリウレタン | |
KR20150090061A (ko) | 활성 에너지선 경화성 수지 조성물, 코팅제 조성물 및 적층체 | |
JP2008075048A (ja) | 塗料用組成物 | |
JP2011042770A (ja) | 活性エネルギー線硬化型オリゴマー、活性エネルギー線硬化型樹脂組成物、硬化被膜、およびプラスチックフィルム。 | |
JP2019035073A (ja) | ポリカーボネートポリオール及びその製造方法 | |
KR20170115566A (ko) | 도료용 우레탄 수지 조성물 및 그 조성물을 사용한 촉감 도료 | |
TW202108652A (zh) | (甲基)丙烯酸酯官能化寡聚物及製備與使用此寡聚物之方法 | |
JP5165900B2 (ja) | 水性ウレタン樹脂組成物 | |
JP2005255979A (ja) | 活性エネルギー線硬化型樹脂組成物の硬化物 | |
JP5056092B2 (ja) | 触感塗料用組成物 | |
JP2017165948A (ja) | ポリウレタン(メタ)アクリレート、組成物、硬化物 | |
JP2017048301A (ja) | ウレタン(メタ)アクリレート、活性エネルギー線硬化性組成物、及びその硬化物 | |
JP6425986B2 (ja) | ウレタン(メタ)アクリレート、並びに活性エネルギー線硬化型ウレタン(メタ)アクリレート組成物及びその硬化物 | |
JP2017171891A (ja) | ポリウレタン(メタ)アクリレート、組成物、硬化物 | |
JP2017132991A (ja) | ポリウレタン(メタ)アクリレート、組成物、硬化物 | |
JP2004196965A (ja) | ウレタン(メタ)アクリレート系化合物及びそれを用いた活性エネルギー線硬化型樹脂組成物 | |
JP5237610B2 (ja) | ウレタン樹脂組成物 | |
JP2008189774A (ja) | 触感塗料組成物 | |
JP2000204233A (ja) | (メタ)アクリル酸エステル、これを用いた樹脂組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100107 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20120425 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120427 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120615 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120703 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120716 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150810 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5056092 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |