JP5473221B2 - 放射線硬化性粉体塗料組成物 - Google Patents
放射線硬化性粉体塗料組成物 Download PDFInfo
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- JP5473221B2 JP5473221B2 JP2007535047A JP2007535047A JP5473221B2 JP 5473221 B2 JP5473221 B2 JP 5473221B2 JP 2007535047 A JP2007535047 A JP 2007535047A JP 2007535047 A JP2007535047 A JP 2007535047A JP 5473221 B2 JP5473221 B2 JP 5473221B2
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- Prior art keywords
- ethylenically unsaturated
- group
- parts
- unsaturated group
- powder composition
- Prior art date
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- 230000005855 radiation Effects 0.000 title claims description 29
- 239000008199 coating composition Substances 0.000 title description 6
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- 229920000728 polyester Polymers 0.000 claims description 47
- -1 2-ethylhexyl Chemical group 0.000 claims description 46
- 229920005989 resin Polymers 0.000 claims description 44
- 239000011347 resin Substances 0.000 claims description 44
- 238000000576 coating method Methods 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 36
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- 239000011248 coating agent Substances 0.000 claims description 30
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 18
- 239000011574 phosphorus Substances 0.000 claims description 18
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- 125000002947 alkylene group Chemical group 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 5
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 claims description 3
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 3
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 claims description 3
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 claims description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 claims description 2
- IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 claims description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- DPXFJZGPVUNVOT-UHFFFAOYSA-N 3-[1,3-bis[3-(dimethylamino)propyl]triazinan-5-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCC1CN(CCCN(C)C)NN(CCCN(C)C)C1 DPXFJZGPVUNVOT-UHFFFAOYSA-N 0.000 claims description 2
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 claims description 2
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 claims description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 claims description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 2
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- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 2
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 claims description 2
- ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 claims description 2
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- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
- BXYVQNNEFZOBOZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNCCCN(C)C BXYVQNNEFZOBOZ-UHFFFAOYSA-N 0.000 claims description 2
- FQBQBRBAJDVVOH-UHFFFAOYSA-N n-ethyl-3-methylbutan-2-amine Chemical compound CCNC(C)C(C)C FQBQBRBAJDVVOH-UHFFFAOYSA-N 0.000 claims description 2
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 claims description 2
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 claims description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 claims description 2
- 229940100684 pentylamine Drugs 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical group CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
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- 238000003847 radiation curing Methods 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 description 19
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- 229910052751 metal Inorganic materials 0.000 description 13
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
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- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
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- ABTNKPAZMOYEAS-UHFFFAOYSA-N oxo-bis(prop-2-enoxy)phosphanium Chemical compound C=CCO[P+](=O)OCC=C ABTNKPAZMOYEAS-UHFFFAOYSA-N 0.000 description 1
- 238000007591 painting process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 239000001384 succinic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- IPDTVSJBYMMTEA-UHFFFAOYSA-N tert-butylphosphanium;acetate Chemical compound CC([O-])=O.CC(C)(C)[PH3+] IPDTVSJBYMMTEA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/061—Polyesters; Polycarbonates
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
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- 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
- C08G2150/20—Compositions for powder coatings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Description
特に、本発明は、それの結合剤が少なくとも1種のエチレン性不飽和樹脂から構成されているところの、紫外線照射によって又は加速電子ビームによって硬化可能である粉体組成物に関し、該組成物は、独特の性質の組合せ特に良好な流れ特性および機械的性質および中でも金属基体への顕著な接着性を経時においても持続して示すペイントおよびワニス塗膜の製造にそれ自体導く。
WO 03/008508(UCB S.A.)は、エチレン性不飽和樹脂と含燐化合物を含み金属基体上への良好な接着を付与する放射線硬化性粉体組成物を開示している。
しかしながら、該組成物の経時においては、幾つかの重要な性質たとえば良好な接着性および柔軟性が失われることがあるということが注目された。
(a)70〜99.4重量部の少なくとも1種のエチレン性不飽和樹脂、
(b)0.5〜20重量部の少なくとも1種の含燐化合物、および
(c)0.1〜10重量部の少なくとも1種のアミン
を含む放射線硬化性粉体組成物を提供する。
(a1)エチレン性不飽和基含有ポリエステル樹脂(特に、非晶質または半結晶質のポリエステル樹脂)
(a2)エチレン性不飽和基を有するアクリル共重合体
(a3)エチレン性不飽和基含有ポリフェノキシ樹脂
(a4)エチレン性不飽和基含有非芳香族エポキシ樹脂
(a5)エチレン性不飽和基含有ポリウレタン
(a6)エチレン性不飽和基含有ポリエステルアミド
から選ばれ、それらは単独で又は混合物として使用される。
酸成分は50〜100モル%のテレフタル酸、イソフタル酸、1,4−シクロヘキサンジカルボン酸または炭素原子数2〜12の直鎖脂肪族二酸と、0〜50モル%の別の飽和および/または不飽和多酸成分(それはフマル酸、マレイン酸、イタコン酸、フタル酸、イソフタル酸、テレフタル酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、1,12−ドデカンジオン酸、トリメリット酸、ピロメリット酸およびそれらの酸無水物から単独で又は混合物として選ばれる)を含有する;
グリコール成分は、酸成分が少なくとも50モル%のテレフタル酸またはイソフタル酸を含有する場合には20〜100モル%のネオペンチルグリコールと、または、酸成分が少なくとも50モル%の1,4−シクロヘキサンジカルボン酸または炭素原子数2〜12の直鎖脂肪族二酸を含有する場合には20〜100モル%の、1,4−シクロヘキサンジオール、1,4−シクロヘキサンジメタノール、水素化ビスフェノールA、2,2,4,4−テトラメチル−1,3−シクロブタンジオール、4,8−ビス(ヒドロキシメチル)−トリシクロ−[5,2,1,02,6]−デカンから選ばれた脂環式ジオールと、または、酸成分が少なくとも50モル%の1,4−シクロヘキサンジカルボン酸、テレフタル酸または炭素原子数2〜12の直鎖脂肪族二酸を含有する場合には20〜100モル%の、エチレングリコール、1,3−プロパンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,7−ヘプタンジオール、1,8−オクタンジオール、1,9−ノナンジオール、1,10−デカンジオール、1,11−ウンデカンジオール、1,12−ドデカンジオールから選ばれた炭素原子数2〜12の飽和直鎖脂肪族ジオールと、0〜80モル%の別のジオールを含有する。
ゲルパーミエーションクロマトグラフィー(GPC)によって測定して1100〜16000の、より好ましくは1300〜8500の数平均分子量(Mn)
ポリエステル1g当り二重結合0.17〜4.00ミリ当量特に0.35〜2.50ミリ当量の不飽和度。
ASTM D4287に従って測定して、ポリエステルが半結晶質である場合には200℃において50000mPa.s未満のそして最も好ましくは175℃において10000mPa.s未満のブルックフィールドコーン/プレート溶融粘度
ASTM D3418に従って示差走査熱量法(DSC)によって測定したときに、ポリエステルが非晶質である場合には35〜80℃のガラス転移温度(Tg)、又はポリエステルが半結晶質である場合には60〜150℃の溶融温度、及び50℃未満のガラス転移温度。
GPCによって測定して、1000〜20000の、より好ましくは、2000〜8000の、数平均分子量(Mn)
アクリル共重合体1g当り二重結合0.35〜3.50ミリ当量の、より好ましくは0.5〜2.5ミリ当量の、不飽和度
ASTM D4287に従って200℃で測定して50,000mPa.s未満のブルックフィールドコーン/プレート溶融粘度
ASTM D3418に従ってDSCによって測定したとき45〜100℃のガラス転移温度(Tg)。
ゲルパーミエーションクロマトグラフィー(GPC)によって測定して500〜5000好ましくは650〜3500の数平均分子量(Mn)
ASTM D3418に従って示差走査熱量法(DSC)によって測定して30〜80℃のガラス転移温度(Tg)
ASTM D4287に従って200℃で測定して25,000mPa.s未満の溶融状態におけるブルックフィールドコーン/プレート粘度。
ゲルパーミエーションクロマトグラフィー(GPC)によって測定して450〜5000の、より好ましくは1000〜3500の、数平均分子量(Mn)
脂肪族不飽和樹脂1g当り二重結合0.4〜4.5ミリ当量の、より好ましくは0.5〜2.5ミリ当量の不飽和度
ASTM D3418に従って示差走査熱量法(DSC)によって測定して30〜80℃のガラス転移温度(Tg)
ASTM D4287に従って200℃で測定して溶融状態で20000mPa.s未満のブルックフィールドコーン/プレート粘度。
(メタ)アクリロイル基含有ポリウレタンの製造に好ましく使用されるポリオールは、C2〜C15脂肪族または脂環式ジオール、ポリエステルポリオールまたはポリエーテルポリオールの中から選ばれる。
800〜15000の、より好ましくは、1300〜8500の、数平均分子量(Mn)
40〜100℃のガラス転移温度(Tg)
ポリエステル1g当り二重結合0.15〜2.00ミリ当量の範囲の、より好ましくは0.35〜1.50ミリ当量の範囲の、不飽和度
200℃で測定して100000mPa.s未満のブルックフィールドコーン/プレート粘度。
800〜16000の、より好ましくは、1300〜8500の、数平均分子量(Mn)
ポリエステルが非晶質であるときに40〜70℃のガラス転移温度(Tg)
ポリエステル1g当り二重結合0.15〜2.00ミリ当量の範囲の、より好ましくは0.35〜1.50ミリ当量の範囲の、不飽和度
200℃で測定して50000mPa.s未満のブルックフィールドコーン/プレート粘度。
各R2は独立に、アルキル、アリールおよびアルケニルから選ばれ、各々は場合によっては1〜3個のエーテルブリッジ、1〜3個の−CO−ブリッジ、および/または1〜3個の−COO−ブリッジを含有していてもよく、そして各々は場合によっては1〜10個のハロゲン、ヒドロキシルおよび/またはアミノ誘導体によって置換されていてもよい;
各R3は独立に、水素またはR4であり、R4はR2についての定義通りである;そしてnは0〜3である。
用語「アラルキレン」は、ここで使用されるとき、アルキレン部分とアリーレン部分の組合せを含む2価基を表わす。
各R5は独立に、水素、または炭素原子数1〜8のアルキル基である;
各R6は独立に、水素、炭素原子数1〜8のアルキル基、および炭素原子数1〜8のハロアルキル基から成る群から選ばれる;
各Aは独立に、炭素原子数1〜9のアルキレン基であり、場合によっては1〜3個のエーテルブリッジを含有していてもよい;そして
mは1〜3である。
各R´は独立に、水素、アルキル、アルケニル、アリール、複素環またはそれらの組合せを表わし、各々は場合によっては1個またはそれ以上のヒドロキシルおよび/またはアミノ誘導体によって置換されていてもよく、そして場合によっては1〜3個のエーテルブリッジ、1〜3個のアミノブリッジ、1〜3個の−CO−ブリッジ、および/または1〜3個の−COO−ブリッジを含有していてもよく;2個のR´部分は環を形成するために互いに結合していてもよい。
各R1は独立に、水素、アルキル、アルケニル、アリール、複素環またはそれらの組合せから選ばれ、各々は場合によっては1個またはそれ以上のヒドロキシルによって置換されていてもよく、そして場合によっては1〜3個のエーテルブリッジ、1〜3個の−CO−ブリッジ、および/または1〜3個の−COO−ブリッジを含有していてもよく;2個のR1部分は環を形成するために互いに結合していてもよい;
各Rは独立に、アルキレン、アルケニレン、アリーレンまたはアラルキレン鎖を表わし、それは1〜3個のエーテルブリッジ、1〜3個の−CO−ブリッジおよび/または1〜3個の−COO−ブリッジを含有していてもよく、そしてそれは場合によっては1個またはそれ以上のヒドロキシルによって置換されていてもよい;
但し、式(I)のアミンはNH3でないことを条件とする。
星印(*)は式(V)の基がポリマー鎖に結合する位置を示している。
本発明によるアミン(c)においては、R1は好ましくはC1〜6アルキルであり;Rは好ましくはC1〜12アルキレンである。アミン(c)が式(V)の基を1つ以上含有するポリマーである場合、ポリマーは好ましくはポリ(メタ)アクリレートである。
使用できる適切な光開始剤は芳香族カルボニル化合物、たとえば、ベンゾフェノンおよびそのアルキル化またはハロゲン化誘導体、アントラキノンおよびその誘導体、チオキサントンおよびその誘導体、ベンゾインエーテル、芳香族または非芳香族アルファジオン、ベンジルジアルキルアセタール、アセトフェノン誘導体およびホスフィンオキシドである。
本発明による放射線硬化性粉体組成物は多様な殆どの基体、たとえば、紙、厚紙、木材、繊維ボード、編織物、プラスチックたとえばポリカーボネート、ポリ(メタ)アクリレート、ポリオレフィン、ポリスチレン、ポリ塩化ビニル、ポリエステル、ポリウレタン、ポリアミド、共重合体たとえばアクリロニトリル−ブタジエン−スチレン(ASB)または酢酪酸セルロースなど、に適用できるが、特に、銅、アルミニウム、鋼などのような様々な特性の金属基体の上に、広範な金属前処理なしでも、適用するように設計されている。
369.7部のネオペンチルグリコールと10.2部のトリメチロールプロパンの混合物を2.1部のn−ブチル錫トリオクトエート触媒と一緒に通常の4口丸底フラスコの中に入れる。
AN= 10mgKOH/g
OHN= 51mgKOH/g
を特徴とする。
200℃の状態にある第一工程のプレポリマーに、96.5部のイソフタル酸を加える。そうして、混合物を徐々に225℃に加熱する。225℃で2時間の後に、そして反応混合物が透明であるときに、0.8部のトリブチルホスファイトを加え、そして徐々に50mmHgの真空を適用する。
AN= 30mgKOH/g
OHN= 2mgKOH/g
Brfld200℃=5400mPa.s
カルボニル官能化ポリエステルを150℃に冷却し、そして0.9部のジ−t−ブチルヒドロキノンを4.6部のエチルトリフェニルホスホニウムブロミドと一緒に加える。次いで、酸素下で攪拌しながら、77.3部のグリシジルメタクリレートをゆっくり加える(30分)。添加後1時間したら、次の特性のメタクリロイル不飽和ポリエステルが得られる:
AN= 5mgKOH/g
OHN= 39mgKOH/g
不飽和= 1.5ミリ当量/g
Brfld200℃= 3800mPa.s
Tgquenched(DSC、20°/分)= 56℃
Mn(GPC)= 4000
AN= 52mgKOH/g
OHN= 2mgKOH/g
AN= 2mgKOH/g
OHN= 48mgKOH/g
不飽和= 0.8ミリ当量/g
Brfld200℃= 150mPa.s
Tmquenched(DSC、20°/分)= 65℃
Mn(GPC)= 2530
AN= 7mgKOH/g
不飽和= 1.24ミリ当量/g
Brfld200℃= 700mPa.s
Tgquenched(DSC、20°/分)= 49℃
Mn(GPC)= 1650
Tg= 76℃
E.E.W.(エポキシ当量重量)= 530g/当量
Mn= 2685
Mw= 5650
反応器に、2.25部のノルソクリル(Norsocryl)200を加え、そして15分後に、2.25部のtert−ブチルホスホニウムアセテートを加える。次いで、65.01部のアクリル酸を30分間かけて加える。
AN= 4.5mgKOH/g
Brookfield150℃= 35000mPa.s
残留溶剤= 0.2重量%
Tg= 70℃
U.E.W.= 1.49ミリ当量/g
Mn= 3145
Mw= 9600
169.50部の2−(ジエチルアミノ)エチルメタクリレート
320.69部のイソボルニルアクリレート
の混合物である。この供給は180分間かかる。
ガラス転移温度(DSC(quenched)): 42℃
Mn(GPC): 1110
Brfld175℃: 2470mPa.s
静電気スプレーガンの助けで吹き付けることによって塗膜を製造するのに使用できる一連の黒色粉体は、実施例1および/または2のポリエステルを、場合によっては、本発明に従い実施例3の(メタ)アクリロイル基含有エポキシ樹脂または実施例4のアクリル共重合体、実施例5で製造されるエチレン性不飽和燐化合物および様々なアミノ化合物との組合せで含む結合剤から製造され、そして比較のためにはアミノ化合物無しでエチレン性不飽和燐化合物だけを含有する組成物またはエチレン性不飽和燐化合物もアミノ化合物も含有しない組成物から製造され、これら粉体の処方物は下記の通りである:
ミクロリン(Microlin)ブラック(チバ) 20部
α−ヒドロキシケトン(イルガキュア2959(チバ)) 8部
ビスアシルホスフィンオキシド(イルガキュア819(チバ)) 32部
流動度調節剤(レジフローPV5(ウォーリーケミー)) 10部
本発明に従う結合剤組成物をもって及び比較のために与えられた結合剤システムをもって実施例7に記載されている通りに処方された粉体を、電圧60kVでの静電気スプレーガンによって、燐酸亜鉛処理鋼(zinc phosphated steel)パネルの上に80〜90μmの塗膜厚さで適用する。
第1欄:処方物の実施例の番号
第2欄:完成結合剤の中の、エチレン性不飽和樹脂の製造実施例の番号と完成結合剤中のそれの重量%
第3欄:完成結合剤の中の、実施例5の含燐化合物の重量%
第4欄:完成結合剤の中の、アミノ化合物の特性とそれの重量%
第5欄:燐酸亜鉛処理鋼の上でのASTM D2795に従うダイレクトインパクト(DI)およびリバースインパクト(RI)に対する耐衝撃値(kg.cm)
第6欄:ASTM D3359に従うテープ試験による燐酸亜鉛処理鋼の上でのクロスカット接着についての格付け値、それによれば、
5B:カットの縁端が完全に平滑である;格子のます目のどれもが脱離しない。
4B:交差箇所において塗膜の小さなフレークが脱離する;面積の5%未満がそうなる。
3B:カットの縁端および交差箇所に沿って塗膜の小さなフレークが脱離する;そうなる面積が格子の5〜15%である。
2B:縁端に沿って及びます目の部分の上で塗膜が剥落している;そうなる面積が格子の15〜35%である。
1B:塗膜がカットの縁端に沿って大きな帯状に剥落しており、そしてます目全体が脱離する;そうなる面積が格子の35〜65%である。
0B:剥落および脱離が等級1よりも悪い。
樹脂については:4週間の経時
粉体については:5週間の経時
硬化塗膜については:1時間の経時と、その後に4週間、8週間、12週間および16週間の経時
tMeHMDA:N,N,N’,N’−テトラメチル−1,6−ヘキサンジアミン
Ex.6=実施例6で製造された通りのアミノ化合物
第1欄:経時を週数(weeks)で表わす
第2欄:結合剤の経時における塗膜のクロスカット接着の値を表わす
第3欄:粉体の経時における塗膜のクロスカット接着の値を表わす
第4欄:塗膜の経時における塗膜のクロスカット接着の値を表わす
Claims (14)
- (a)+(b)+(c)の100重量部当たり、
(a)70〜99.4重量部の少なくとも1種のエチレン性不飽和樹脂、
(b)0.5〜20重量部の少なくとも1種の含燐化合物、および
(c)0.1〜10重量部の、化合物(b)とは異なる少なくとも1種のアミン
を含む放射線硬化性粉体組成物であって、
前記(b)の含燐化合物が、式
(式中、
各R 5 は独立に、水素、または炭素原子数1〜8のアルキル基である;
各R 6 は独立に、水素、炭素原子数1〜8のアルキル基、および炭素原子数1〜8のハロアルキル基から成る群から選ばれる;
各Aは独立に、炭素原子数1〜9のアルキレン基であり、場合によっては1〜3個のエーテルブリッジを含有していてもよい;そして
mは1〜3である。)
に相当し、
前記(c)のアミンが、式(I)、(II)、(III)もしくは(IV)のアミンであるか、又は式(V)の基を1個もしくはそれ以上含有するポリマーであるか、又はそれらの混合物である:
(式中、各R1は独立に、水素、アルキル、アルケニル、アリール、複素環またはそれらの組合せから選ばれ、各々は場合によっては1個またはそれ以上のヒドロキシルによって置換されていてもよく、そして場合によっては1〜3個のエーテルブリッジ、1〜3個の−CO−ブリッジ、および1〜3個の−COO−ブリッジから選ばれる少なくとも一員を含有していてもよく;2個のR1部分は環を形成するために互いに結合していてもよい;
各Rは独立に、アルキレン、アルケニレン、アリーレンまたはアラルキレン鎖を表わし、それは1〜3個のエーテルブリッジ、1〜3個の−CO−ブリッジおよび1〜3個の−COO−ブリッジから選ばれる少なくとも一員を含有していてもよく、そしてそれは場合によっては1個またはそれ以上のヒドロキシルによって置換されていてもよい。)、放射線硬化性粉体組成物。 - アミン(c)が、プロピルアミン、ブチルアミン、sec−ブチルアミン、tert−ブチルアミン、ペンチルアミン、ヘキシルアミン、2−エチルヘキシルアミン、シクロヘキシルアミン、オクチルアミン、アニリン、エチレンジアミン、1,2−ジアミノプロパン、1,3−ジアミノプロパン、2,2−ジメチル−1,3−プロパンジアミン、1,4−ブタンジアミン、1,5−ペンタンジアミン、1,6−ヘキサンジアミン、1,2−シクロヘキサンジアミン、1,3−シクロヘキサンジアミン、1,4−シクロヘキサンジアミン、3−(メチルアミノ)プロピルアミン、3−(ジメチルアミノ)プロピルアミン、3−(エチルアミノ)プロピルアミン、イソホロンジアミン、4,4’−ジアミノジシクロヘキシルメタン、3,3’−ジメチル−4,4’−ジアミノジシクロヘキシルメタン、4,4’−ジアミノジフェニルメタン、3,3’−ジメチル−4,4’−ジアミノジフェニルメタン、3−(ジエチルアミノ)プロピルアミン、3−メトキシプロピルアミン、N−エチル−1,2−ジメチルプロピルアミン、イミノビスプロピルアミン、3,3’−イミノビス(N,N’−ジメチルプロピルアミン)、ジエチルアミン、ジプロピルアミン、ジブチルアミン、ジヘキシルアミン、ジ−(2−エチルヘキシル)アミン、トリエチルアミン、トリ−n−ブチルアミン、トリブチルアミン、トリヘキシルアミン、トリ−(2−エチルヘキシル)アミン、トリデシルアミン、3−アミノ−1−プロパノール、アミノエトキシエタノール、アミノエタノール、N,N−ビス(3−アミノプロピル)メチルアミン、2−(ジエチルアミノ)エチルアミン、ジエチレントリアミン、2−メトキシエチルアミン、メチレンジアニリン、4,7,10−トリオキサトリデカン−1,13−ジアミン、N−(2−アミノエチル)−1,2−エタンジアミン、ジ(2−メトキシエチル)アミン、N,N’−ビス(3−アミノプロピル)エチレンジアミン、N−(2−アミノエチル)−1,3−プロピレンジアミン、N,N−ジエチルエタノールアミン、N,N−ジメチルアミノジグリコール、N,N−ジメチルブチルアミン、N,N−ジメチルシクロヘキシルアミン、N,N−ジメチルエタノールアミン、ジメチルエチルアミン、ジトリデシルアミン、N−エチルシクロヘキシルアミン、N−メチルシクロヘキシルアミン、メチルジエタノールアミン、N−モノメチルエタノールアミン、N,N,N’,N”,N”−ペンタメチルジエチレントリアミン、N,N,N’,N’−テトラメチル−1,6−ヘキサンジアミン、N,N,N’,N’−テトラエチル−1,6−ヘキサンジアミン、1,8−ジアザビシクロ−5,4,0−ウンデカ−7−エン、1,4−ジアザビシクロ−2,2,2−オクタン、1,3,5−トリス(ジメチルアミノプロピル)−ヘキサヒドロトリアジン、1,4−ジメチルピペラジン、N,N’−ジメチルピペラジン、2,2’−ジモルホリノジエチルエーテル、モルホリン、N−メチルモルホリン、N−エチルモルホリン、シス−2,6−ジメチルモルホリン、ピペラジン、N−メチルピペラジン、N−エチルピペラジン、N−メチルピペリジン、N−エチルピペリジン、ヒドロキシエチルピペリジン、イミダゾール、場合によってヒドロキシメチル、メトキシメチルおよびブトキシメチルから選ばれる少なくとも一員によって置換されていてもよい2,4,6−トリアミノ−1,3,5−トリアジン、または2−(tert−ブチルアミノ)エチルメタクリレートおよび2−(ジエチルアミノ)エチルメタクリレートから選ばれる少なくとも一員を組み込んであるアミン含有アクリル共重合体、またはそれらの混合物から選ばれる、請求項1に記載の放射線硬化性粉体組成物。
- アミンがN,N,N’,N’−テトラメチル−1,6−ヘキサンジアミンである、請求項2に記載の放射線硬化性粉体組成物。
- R5が水素またはメチルであり、R6が水素であり、Aがエチレン基であり、そしてmが1、2または3である、請求項1に記載の放射線硬化性粉体組成物。
- エチレン性不飽和樹脂(a)が、
(a1)エチレン性不飽和基含有ポリエステル、
(a2)エチレン性不飽和基含有アクリル共重合体、
(a3)エチレン性不飽和基含有ポリフェノキシ樹脂、
(a4)エチレン性不飽和基含有非芳香族エポキシ樹脂、
(a5)エチレン性不飽和基含有ポリウレタン、
(a6)エチレン性不飽和基含有ポリエステルアミド、
またはそれらのいずれかの混合物
から選ばれる、請求項1〜4のいずれか一項に記載の放射線硬化性粉体組成物。 - エチレン性不飽和基含有ポリエステル(a1)はジイソシアネートとヒドロキシアルキル(メタ)アクリレートおよびヒドロキシル基含有ポリエステルとの反応から又はエチレン性不飽和基およびエポキシ官能基を有する化合物とカルボキシル基を含有するポリエステルとの反応から得ることができる、請求項5に記載の放射線硬化性粉体組成物。
- エチレン性不飽和ポリエステル(a1)が、
1100〜16000の範囲の数平均分子量
ポリエステル1g当り二重結合0.17〜4.00ミリ当量の不飽和度
を特徴とする、請求項5または6に記載の放射線硬化性粉体組成物。 - エチレン性不飽和基含有アクリル共重合体(a2)が、
アクリルまたはメタクリル基を有する少なくとも1種のモノマー40〜95モル%、別のエチレン性不飽和モノマー0〜60モル%、およびエポキシ、カルボキシル、ヒドロキシルまたはイソシアネート基から選ばれた官能基を有するエチレン性不飽和モノマー5〜60モル%から得られたアクリル共重合体と、
エチレン性不飽和基を有しかつカルボキシル、エポキシ、イソシアネートまたはヒドロキシル基と反応可能な官能基を有する化合物と
の反応から得られ、
前記アクリル共重合体(a2)が、
1000〜20000の範囲の数平均分子量、
アクリル共重合体1g当り二重結合0.35〜3.50ミリ当量の不飽和度、
50,000mPa.s未満の溶融粘度(200℃におけるコーン/プレート)、および
45〜100℃の範囲のガラス転移温度
を特徴とする、
請求項5〜7のいずれか一項に記載の放射線硬化性粉体組成物。 - エチレン性不飽和基含有ポリフェノキシ樹脂(a3)が(メタ)アクリル酸とグリシジル基含有ポリフェノキシ樹脂との反応生成物であり、前記ポリフェノキシ樹脂(a3)が
500〜5000の範囲の数平均分子量、
30〜80℃の範囲のガラス転移温度、
ポリフェノキシ樹脂1g当り二重結合0.2〜6.0ミリ当量の範囲の不飽和度、および
25000mPa.s未満の溶融粘度(200℃におけるコーン/プレート)
を特徴とする、請求項5〜8のいずれか一項に記載の放射線硬化性粉体組成物。 - 少なくとも1種のエチレン性不飽和基含有ポリエステル(a1)を含むか、又は少なくとも1種のエチレン性不飽和基含有ポリエステル(a1)と少なくとも1種のエチレン性不飽和基含有ポリフェノキシ樹脂(a3)及び少なくとも1種のエチレン性不飽和基含有アクリル共重合体(a2)のいずれか一方もしくは両方との混合物を含む、請求項5〜9のいずれか一項に記載の放射線硬化性粉体組成物。
- (a)+(b)+(c)+(d)の100重量部当たり、エチレン性不飽和モノマーまたはオリゴマー(d)を0〜20重量部、光開始剤を0〜15重量部、UV光吸収剤、光安定剤、流動度調節剤、脱泡剤およびコーティング特性改質物質から選ばれた添加剤を0〜10重量部、そして、顔料および充填剤から選ばれる少なくとも一員を0〜40重量部、含む、請求項1〜10のいずれか一項に記載の放射線硬化性粉体組成物。
- 請求項1〜11のいずれか一項に記載の放射線硬化性粉体組成物を含む粉体ワニスまたは粉体ペイント。
- 請求項1〜11のいずれか一項に記載の放射線硬化性粉体組成物または請求項12に記載の粉体ワニスまたは粉体ペイントを物品の上に付着させた後に、そうして得られた塗膜を溶融し、そして溶融状態の塗膜を放射線硬化する、物品被覆方法。
- 請求項13に記載の方法によって部分的に又は完全に被覆された物品。
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CA (1) | CA2580386C (ja) |
ES (1) | ES2393198T3 (ja) |
TW (1) | TWI391441B (ja) |
WO (1) | WO2006037493A1 (ja) |
Families Citing this family (10)
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US8376013B2 (en) | 2008-03-11 | 2013-02-19 | Duke University | Plasmonic assisted systems and methods for interior energy-activation from an exterior source |
WO2011069984A1 (de) * | 2009-12-09 | 2011-06-16 | Basf Se | Teilaromatische, teilkristalline copolyamide |
US9493715B2 (en) * | 2012-05-10 | 2016-11-15 | General Electric Company | Compounds and methods for inhibiting corrosion in hydrocarbon processing units |
CN103555129A (zh) * | 2013-09-25 | 2014-02-05 | 天长市天泰光电科技有限公司 | 一种led灯的抗紫外抗热老化散热涂料及其制备方法 |
CN107428970B (zh) | 2015-03-26 | 2021-09-10 | 日铁化学材料株式会社 | 纤维增强塑料成型用材料、其制造方法和成型物 |
KR101655931B1 (ko) * | 2015-09-24 | 2016-09-08 | 주식회사 투에이취켐 | 하이브리드 분체 도료 |
CA3041660A1 (en) * | 2016-10-28 | 2018-05-03 | Dsm Ip Assets B.V. | Thermosetting compositions and forming three-dimensional objects therefrom |
CN110072900A (zh) | 2016-12-12 | 2019-07-30 | Ppg工业俄亥俄公司 | 丙烯酸类聚酯树脂和含有其的水性涂料组合物 |
CA3107320A1 (en) * | 2018-07-25 | 2020-01-30 | Ppg Industries Ohio, Inc. | A product coated with an aqueous or powder coating composition comprising an acrylic polyester resin |
CN108976951A (zh) * | 2018-08-02 | 2018-12-11 | 安徽信达家居有限公司 | 一种适用于户外橡木家具的耐老化性涂料 |
Family Cites Families (15)
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US4000349A (en) * | 1974-01-08 | 1976-12-28 | Ford Motor Company | Plural coated abrasion and corrosion resistant article |
JPS51129482A (en) * | 1975-03-28 | 1976-11-11 | Hitachi Chem Co Ltd | Fiber-reinforced polyester resin composition for use in molding |
NL8403706A (nl) * | 1984-12-06 | 1986-07-01 | Dsm Resins Bv | Fotopolymeriseerbare samenstelling en een fotoinitiatorsysteem. |
BE1010713A3 (fr) * | 1996-10-25 | 1998-12-01 | Ucb Sa | Compositions en poudre a base de polyesters semi-cristallins et de copolymeres acryliques; contenant des groupes (meth)acrylyle. |
BE1010712A3 (fr) * | 1996-10-25 | 1998-12-01 | Ucb Sa | Compositions en poudre a base de polyesters semi-cristallins et de polyesters amorphes, contenant des groupes methacrylyle terminaux. |
US5922473A (en) * | 1996-12-26 | 1999-07-13 | Morton International, Inc. | Dual thermal and ultraviolet curable powder coatings |
EP0949286B1 (en) * | 1996-12-27 | 2005-03-02 | Nippon Soda Co., Ltd. | Curatives for epoxy resin, curing accelerator, and epoxy resin composition |
US6376584B1 (en) * | 1999-02-25 | 2002-04-23 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
US7268171B2 (en) * | 2000-04-27 | 2007-09-11 | Dainippon Ink And Chemicals, Inc. | Water-based coating composition curable with actinic energy ray, coated metallic material with cured film of the composition, production process, and method of bonding coated metallic material |
DE10027295A1 (de) * | 2000-06-02 | 2001-12-06 | Basf Coatings Ag | Effektpigmente enthaltende Pulverlacke und Pulverlackdispersionen (Pulverslurries) |
US6710137B2 (en) * | 2001-02-06 | 2004-03-23 | Dainippon Ink And Chemicals, Inc. | Resin composition for powder coating, powder coating, and article coated therewith |
DE10126651A1 (de) * | 2001-06-01 | 2002-12-12 | Basf Coatings Ag | Pulverlacksuspensionen (Pulverslurries) und Pulverlacke, Verfahren zu ihrer Herstellung und ihre Verwendung |
TW587090B (en) * | 2001-07-19 | 2004-05-11 | Ucb Sa | Radiation curable powder coating compositions |
TWI237052B (en) * | 2001-07-26 | 2005-08-01 | Surface Specialties Sa | Radiation curable powder coating compositions |
US6777027B2 (en) * | 2002-10-08 | 2004-08-17 | Rohm And Haas Company | Coating powders for smooth, low gloss finishes, and powder coatings formed therefrom |
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2004
- 2004-10-06 EP EP04023751A patent/EP1645583A1/en not_active Withdrawn
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2005
- 2005-09-23 EP EP05788976A patent/EP1799741B1/en active Active
- 2005-09-23 JP JP2007535047A patent/JP5473221B2/ja active Active
- 2005-09-23 CN CN2005800343068A patent/CN101035827B/zh active Active
- 2005-09-23 ES ES05788976T patent/ES2393198T3/es active Active
- 2005-09-23 CA CA2580386A patent/CA2580386C/en not_active Expired - Fee Related
- 2005-09-23 WO PCT/EP2005/010344 patent/WO2006037493A1/en active Application Filing
- 2005-09-23 KR KR1020077010381A patent/KR20070074614A/ko not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
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CN101035827B (zh) | 2011-06-15 |
WO2006037493A1 (en) | 2006-04-13 |
EP1799741B1 (en) | 2012-08-15 |
CN101035827A (zh) | 2007-09-12 |
US7695773B2 (en) | 2010-04-13 |
CA2580386C (en) | 2013-08-27 |
CA2580386A1 (en) | 2006-04-13 |
US20080206480A1 (en) | 2008-08-28 |
JP2008516020A (ja) | 2008-05-15 |
TWI391441B (zh) | 2013-04-01 |
EP1645583A1 (en) | 2006-04-12 |
ES2393198T3 (es) | 2012-12-19 |
EP1799741A1 (en) | 2007-06-27 |
KR20070074614A (ko) | 2007-07-12 |
TW200626664A (en) | 2006-08-01 |
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