JP3778578B2 - 粉末被覆剤の為の結合剤 - Google Patents
粉末被覆剤の為の結合剤 Download PDFInfo
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- JP3778578B2 JP3778578B2 JP21048293A JP21048293A JP3778578B2 JP 3778578 B2 JP3778578 B2 JP 3778578B2 JP 21048293 A JP21048293 A JP 21048293A JP 21048293 A JP21048293 A JP 21048293A JP 3778578 B2 JP3778578 B2 JP 3778578B2
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- 238000000576 coating method Methods 0.000 title claims abstract description 27
- 239000000843 powder Substances 0.000 title claims abstract description 23
- 239000011230 binding agent Substances 0.000 title claims abstract description 18
- 239000011248 coating agent Substances 0.000 title claims description 18
- 239000004814 polyurethane Substances 0.000 claims abstract description 27
- 229920002635 polyurethane Polymers 0.000 claims abstract description 27
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 229920006305 unsaturated polyester Polymers 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 10
- -1 1,3-propanediol diol Chemical class 0.000 claims description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 2
- 229920000728 polyester Polymers 0.000 abstract description 12
- 230000000903 blocking effect Effects 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 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 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 238000009503 electrostatic coating Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 150000002513 isocyanates Chemical class 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
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-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
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000006120 scratch resistant coating Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-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
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical class O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- IANYIYFOTQCDBY-UHFFFAOYSA-N 2,2-dimethylbutane prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCC(C)(C)C IANYIYFOTQCDBY-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HVOBSBRYQIYZNY-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethanol Chemical compound NCCNCCNCCO HVOBSBRYQIYZNY-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- YQRCNDBBOJYCQV-UHFFFAOYSA-N 3-(1,4-dimethylcyclohexyl)propan-1-amine Chemical compound NCCCC1(CCC(CC1)C)C YQRCNDBBOJYCQV-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
- FNVOFDGAASRDQY-UHFFFAOYSA-N 3-amino-2,2-dimethylpropan-1-ol Chemical compound NCC(C)(C)CO FNVOFDGAASRDQY-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
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- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
-
- 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
- C08G2150/20—Compositions for powder coatings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4228514A DE4228514A1 (de) | 1992-08-27 | 1992-08-27 | Bindemittel für Pulverlacke |
| DE4228514:3 | 1992-08-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06184467A JPH06184467A (ja) | 1994-07-05 |
| JP3778578B2 true JP3778578B2 (ja) | 2006-05-24 |
Family
ID=6466569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21048293A Expired - Lifetime JP3778578B2 (ja) | 1992-08-27 | 1993-08-25 | 粉末被覆剤の為の結合剤 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5620751A (https=) |
| EP (1) | EP0585742B1 (https=) |
| JP (1) | JP3778578B2 (https=) |
| KR (1) | KR100297307B1 (https=) |
| AT (1) | ATE146512T1 (https=) |
| BR (1) | BR9303493A (https=) |
| CA (1) | CA2103520C (https=) |
| DE (2) | DE4228514A1 (https=) |
| DK (1) | DK0585742T3 (https=) |
| ES (1) | ES2097407T3 (https=) |
| GR (1) | GR3022134T3 (https=) |
| MX (1) | MX9305172A (https=) |
| MY (1) | MY110209A (https=) |
| TW (1) | TW245737B (https=) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1007373A3 (nl) * | 1993-07-30 | 1995-05-30 | Dsm Nv | Stralingsuithardbare bindmiddelsamenstelling voor poederverfformuleringen. |
| DE4432645A1 (de) * | 1994-09-14 | 1996-03-21 | Hoechst Ag | Bindemittel für Pulverlacke |
| DE4432644A1 (de) | 1994-09-14 | 1996-03-21 | Hoechst Ag | Ungesättigte Polyesterurethanacrylate als Bindemittel für Pulverlacke |
| SE504783C2 (sv) | 1995-08-10 | 1997-04-21 | Triline Ab | Förfarande och anläggning för pulverlackering |
| DE19600146A1 (de) * | 1996-01-04 | 1997-07-10 | Basf Ag | Verwendung von reaktiven, präpolymeren organischen Verbindungen |
| US5747552A (en) * | 1996-04-10 | 1998-05-05 | Hehr International Inc. | Radiant energy curable acrylic urethane prepolymer resin compositions and method |
| US20010002274A1 (en) * | 1996-06-14 | 2001-05-31 | Peter Lessmeister | Metal strip coating process |
| 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 |
| US6426116B1 (en) | 1997-10-15 | 2002-07-30 | University Of South Florida | Supercritical fluid aided coating of particulate material |
| AU1519099A (en) * | 1997-11-04 | 1999-05-24 | Composite Technology Group, Llc | Nonstyrenated polyester and vinylester resins |
| US5925402A (en) * | 1998-07-15 | 1999-07-20 | Morton International, Inc. | Method of forming a hidden identification using powder coating |
| DE19835206A1 (de) | 1998-08-04 | 2000-02-17 | Basf Coatings Ag | Wäßrige Pulverklarlack-Dispersion |
| DE19903725A1 (de) | 1999-01-30 | 2000-08-10 | Basf Coatings Ag | Bindemittelgemische und ihre Verwendung in mit aktinischer Strahlung und/oder thermisch härtbaren Beschichtungsstoffen |
| DE19908013A1 (de) | 1999-02-25 | 2000-08-31 | Basf Coatings Ag | Mit aktinischer Strahlung und gegebenenfalls themisch härtbare Pulverslurrys, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19908018A1 (de) | 1999-02-25 | 2000-08-31 | Basf Coatings Ag | Thermisch und mit aktinischer Strahlung härtbare Pulverslurry, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19939843A1 (de) * | 1999-08-23 | 2001-03-01 | Bayer Ag | Neue Bindemittel für Pulverlacke enthaltend (Meth)Acryloylgruppen aufweisende Oligo- und Polyurethane |
| DE10002805A1 (de) | 2000-01-24 | 2001-07-26 | Basf Coatings Ag | Strahlenhärtbare Pulverlacke |
| EP1275496B1 (en) | 2000-04-03 | 2011-09-21 | Mitsubishi Chemical Corporation | Layered product, bonding method, and composition curable with actinic energy ray |
| DE10032136A1 (de) * | 2000-07-01 | 2002-01-17 | Basf Coatings Ag | Thermisch und mit aktinischer Strahlung härtbares Mehrkomponentensystem, Verfahren zu seiner Herstellung und seine Verwendung |
| DE10058617A1 (de) * | 2000-11-25 | 2002-05-29 | Degussa | UV-Härtbare Pulverlackzusammensetzungen |
| DE10063159A1 (de) * | 2000-12-18 | 2002-07-04 | Basf Coatings Ag | Mit aktinischer Strahlung aktivierbare Blends aus kristallinen und amorphen Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10156322A1 (de) * | 2001-11-19 | 2003-06-05 | Bayer Ag | Feste strahlenhärtende Bindemittel |
| DE10163827A1 (de) * | 2001-12-22 | 2003-07-03 | Degussa | Strahlen härtbare Pulverlackzusammensetzungen und deren Verwendung |
| DE10163826A1 (de) * | 2001-12-22 | 2003-07-03 | Degussa | Strahlen härtbare Pulverlackzusammensetzungen und deren Verwendung |
| EP1336629A3 (de) * | 2002-02-16 | 2003-10-15 | Degussa AG | Verfahren zur Herstellung von Urethan(meth)acrylaten |
| EP1443059A1 (en) | 2003-02-02 | 2004-08-04 | Solutia Italy S.r.l. | Resins for powder coating compositions |
| MXPA05011847A (es) | 2003-05-06 | 2006-01-26 | Ciba Sc Holding Ag | Revestimientos fotocurados y estabilizados. |
| DE10356041A1 (de) * | 2003-12-01 | 2005-06-23 | Bayer Materialscience Ag | Feste,strahlenhärtende Bindemittel mit Reaktivverdünnern |
| EP1711862B1 (en) | 2004-02-02 | 2014-09-10 | Basf Se | Functionalized photoinitiators |
| WO2008090640A1 (ja) | 2007-01-23 | 2008-07-31 | Fujifilm Corporation | オキシム化合物、感光性組成物、カラーフィルタ及びその製造方法、並びに液晶表示素子 |
| JP5535064B2 (ja) | 2007-05-11 | 2014-07-02 | ビーエーエスエフ ソシエタス・ヨーロピア | オキシムエステル光重合開始剤 |
| US8911921B2 (en) | 2007-05-11 | 2014-12-16 | Ciba Corporation | Oxime ester photoinitiators |
| US20080306221A1 (en) * | 2007-06-08 | 2008-12-11 | Ppg Industries Ohio, Inc. | (meth)acrylate functional polyurethane and method of making |
| RU2489450C9 (ru) | 2007-10-17 | 2014-01-27 | Басф Се | Фотолатентные катализаторы на основе металлорганических соединений |
| EP2307472A1 (de) * | 2008-07-23 | 2011-04-13 | Basf Se | Verwendung von 2-isopropyl-2-alkyl-1,3-propandiolen zur herstellung von polymeren |
| JP5650196B2 (ja) | 2009-03-24 | 2015-01-07 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 新規なオリゴ官能性の光開始剤 |
| JP5714008B2 (ja) | 2009-07-30 | 2015-05-07 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 高分子光開始剤 |
| BR112012005909A2 (pt) | 2009-09-15 | 2020-08-25 | Basf Se | compostos do catalisador de quelato de ti, formulação de catalisador de quelato de ti, uso do composto de catalisador de quelato de ti, ou da formulação de catalisador de quelato de ti, composição polimerizável, processo para a polimerização de compostos, uso da composição polimerizável, substrato revestido, e, composição polimerizada ou reticulada |
| US10207261B2 (en) | 2009-09-15 | 2019-02-19 | Basf Se | Photo-latent titanium catalysts |
| IT1397259B1 (it) * | 2009-12-04 | 2013-01-04 | Max Canti | Decorazione e smaltatura di protezione su biscotto ceramico o vetro in risparmio di energia; nobilitazione di altre superfici grezze di materiali diversi quali conglomerati legnosi o lapidei con contemporanea dotazione di finiture opache o lucide , o goffrate. processo , macchina , elementi ottenuti. |
| CN103153952B (zh) | 2010-10-05 | 2016-07-13 | 巴斯夫欧洲公司 | 苯并咔唑化合物的肟酯衍生物及其在可光聚合组合物中作为光敏引发剂的用途 |
| US9051397B2 (en) | 2010-10-05 | 2015-06-09 | Basf Se | Oxime ester |
| RU2610090C9 (ru) | 2011-04-05 | 2018-04-26 | Басф Се | Фотолатентные катализаторы на основе титан-оксо-хелатов |
| EP2788325B1 (en) | 2011-12-07 | 2016-08-10 | Basf Se | Oxime ester photoinitiators |
| KR102013541B1 (ko) | 2012-05-09 | 2019-08-22 | 바스프 에스이 | 옥심 에스테르 광개시제 |
| WO2014060450A1 (en) | 2012-10-19 | 2014-04-24 | Basf Se | Hybrid photoinitiators |
| EP2935393A4 (en) | 2012-12-18 | 2016-06-01 | Basf Se | SEMICONDUCTOR MATERIALS BASED ON NAPHTHALENDIIMIDE VINYLENE OLIGOTHIOPHENO VINYLENE POLYMERS |
| CN110845530A (zh) | 2012-12-19 | 2020-02-28 | Igm集团公司 | 双酰基次膦酸的衍生物、其制备及其作为光敏引发剂的用途 |
| US8721396B1 (en) * | 2013-03-12 | 2014-05-13 | BTD Wood Powder Coating, Inc. | Method for preparing and buffing a powder coated wood substrate |
| AU2014288876B2 (en) | 2013-07-08 | 2018-11-22 | IGM Group B.V | Liquid bisacylphosphine oxide photoinitiator |
| JP6469669B2 (ja) | 2013-07-08 | 2019-02-13 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | オキシムエステル光開始剤 |
| US10113075B2 (en) | 2014-09-04 | 2018-10-30 | Igm Malta Limited | Polycyclic photoinitiators |
| JP6633814B2 (ja) | 2016-09-02 | 2020-01-22 | アイジーエム グループ ビー．ヴィ． | 光開始剤としての多環式グリオキシレート |
| CN111630081B (zh) | 2018-01-26 | 2023-10-31 | 湛新荷兰有限公司 | 粉末涂料组合物 |
| WO2022236519A1 (en) | 2021-05-10 | 2022-11-17 | Allnex Resins (Shanghai) Co., Ltd. | Powder coating compostion blend |
| AU2022307230A1 (en) | 2021-07-05 | 2023-11-16 | Allnex Netherlands B.V. | Powder coating precursor catalyst |
| BR112023023394A2 (pt) | 2021-07-05 | 2024-01-23 | Allnex Netherlands Bv | Composição de revestimento em pó, componente doador reticulável a e/ou componente aceptor reticulável b, método para revestimento em pó de um substrato, e, artigos revestidos com um pó |
| CA3268107A1 (en) | 2022-11-07 | 2024-05-16 | Allnex Netherlands B.V. | TWO-COMPONENT POWDER COATING COMPOSITION INCLUDING A SEPARATE CATALYTIC SYSTEM |
| CN120677213A (zh) * | 2023-03-30 | 2025-09-19 | 大日本涂料株式会社 | 粉体涂料组合物、涂膜及涂装体 |
| DE102024113735A1 (de) | 2024-05-16 | 2025-11-20 | Schaeffler Technologies AG & Co. KG | Wälzlagerelement, Windkraftanlage und Verfahren zum Beschichten eines Wälzlagerelementes |
| WO2026057274A1 (en) | 2024-09-13 | 2026-03-19 | Basf Se | Oxime ester photoinitiators |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3448172A (en) * | 1966-12-08 | 1969-06-03 | Wyandotte Chemicals Corp | Flexibilized polyester resin compositions containing polyurethanes modified with vinyl monomers and process therefor |
| US3719522A (en) * | 1970-12-21 | 1973-03-06 | Ford Motor Co | Vinyl resin and acrylic rubber-urethane-acrylate paint and painting process |
| JPS5419895B2 (https=) * | 1973-07-27 | 1979-07-18 | ||
| JPS5929308B2 (ja) * | 1975-05-22 | 1984-07-19 | 日本ペイント （株） | 光硬化性被覆組成物の硬化方法 |
| JPS5281394A (en) * | 1975-12-29 | 1977-07-07 | Showa Highpolymer Co Ltd | Curable resin compositions |
| JPS5667322A (en) * | 1979-11-05 | 1981-06-06 | Showa Highpolymer Co Ltd | Curable resin composition |
| JPH0745556B2 (ja) * | 1987-06-08 | 1995-05-17 | 昭和高分子株式会社 | 硬化性樹脂組成物 |
| DE3924679A1 (de) * | 1989-07-26 | 1991-01-31 | Bayer Ag | Verwendung von (meth)acryloylgruppen aufweisenden polyurethanen als bindemittel fuer pulverlacke |
-
1992
- 1992-08-27 DE DE4228514A patent/DE4228514A1/de not_active Withdrawn
-
1993
- 1993-07-20 TW TW82105771A patent/TW245737B/zh not_active IP Right Cessation
- 1993-08-06 CA CA 2103520 patent/CA2103520C/en not_active Expired - Fee Related
- 1993-08-19 AT AT93113257T patent/ATE146512T1/de not_active IP Right Cessation
- 1993-08-19 EP EP19930113257 patent/EP0585742B1/de not_active Expired - Lifetime
- 1993-08-19 ES ES93113257T patent/ES2097407T3/es not_active Expired - Lifetime
- 1993-08-19 DE DE59304798T patent/DE59304798D1/de not_active Expired - Lifetime
- 1993-08-19 DK DK93113257T patent/DK0585742T3/da active
- 1993-08-23 KR KR1019930016326A patent/KR100297307B1/ko not_active Expired - Lifetime
- 1993-08-25 JP JP21048293A patent/JP3778578B2/ja not_active Expired - Lifetime
- 1993-08-25 MY MYPI93001715A patent/MY110209A/en unknown
- 1993-08-26 MX MX9305172A patent/MX9305172A/es not_active IP Right Cessation
- 1993-08-26 BR BR9303493A patent/BR9303493A/pt not_active IP Right Cessation
-
1996
- 1996-03-14 US US08/615,433 patent/US5620751A/en not_active Expired - Lifetime
- 1996-12-20 GR GR960403572T patent/GR3022134T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5620751A (en) | 1997-04-15 |
| KR100297307B1 (ko) | 2001-11-22 |
| DE4228514A1 (de) | 1994-03-03 |
| CA2103520A1 (en) | 1994-02-28 |
| JPH06184467A (ja) | 1994-07-05 |
| EP0585742A1 (de) | 1994-03-09 |
| ATE146512T1 (de) | 1997-01-15 |
| BR9303493A (pt) | 1994-03-15 |
| KR940004020A (ko) | 1994-03-14 |
| DE59304798D1 (de) | 1997-01-30 |
| ES2097407T3 (es) | 1997-04-01 |
| CA2103520C (en) | 2003-04-01 |
| MX9305172A (es) | 1994-05-31 |
| MY110209A (en) | 1998-02-28 |
| GR3022134T3 (en) | 1997-03-31 |
| DK0585742T3 (da) | 1997-01-13 |
| TW245737B (https=) | 1995-04-21 |
| EP0585742B1 (de) | 1996-12-18 |
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