JP6436996B2 - 放射線硬化性で水分散性のポリウレタン(メタ)アクリレート - Google Patents
放射線硬化性で水分散性のポリウレタン(メタ)アクリレート Download PDFInfo
- Publication number
- JP6436996B2 JP6436996B2 JP2016537242A JP2016537242A JP6436996B2 JP 6436996 B2 JP6436996 B2 JP 6436996B2 JP 2016537242 A JP2016537242 A JP 2016537242A JP 2016537242 A JP2016537242 A JP 2016537242A JP 6436996 B2 JP6436996 B2 JP 6436996B2
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- Japan
- Prior art keywords
- diol
- acrylate
- meth
- group
- urethane
- 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.)
- Expired - Fee Related
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 71
- 230000005855 radiation Effects 0.000 title claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 16
- 239000004814 polyurethane Substances 0.000 title description 19
- 229920002635 polyurethane Polymers 0.000 title description 19
- 239000000049 pigment Substances 0.000 claims description 126
- 238000007639 printing Methods 0.000 claims description 100
- -1 fleece Substances 0.000 claims description 82
- 239000005056 polyisocyanate Substances 0.000 claims description 70
- 229920001228 polyisocyanate Polymers 0.000 claims description 70
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 46
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 125000005442 diisocyanate group Chemical group 0.000 claims description 31
- 239000006185 dispersion Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 26
- 150000002009 diols Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 24
- 239000008199 coating composition Substances 0.000 claims description 23
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 22
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 18
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 18
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 15
- 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 15
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 239000011248 coating agent Substances 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 10
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 10
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 229960004063 propylene glycol Drugs 0.000 claims description 9
- 235000013772 propylene glycol Nutrition 0.000 claims description 9
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 8
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 7
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 7
- 239000004698 Polyethylene Substances 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 claims description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 6
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 6
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000000123 paper Substances 0.000 claims description 6
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 6
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002023 wood Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 239000004358 Butane-1, 3-diol Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000004568 cement Substances 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 4
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 4
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 claims description 3
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 claims description 3
- DBTGFWMBFZBBEF-UHFFFAOYSA-N 2,4-dimethylpentane-2,4-diol Chemical compound CC(C)(O)CC(C)(C)O DBTGFWMBFZBBEF-UHFFFAOYSA-N 0.000 claims description 3
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 claims description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 3
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 3
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 claims description 3
- GCXZDAKFJKCPGK-UHFFFAOYSA-N heptane-1,2-diol Chemical compound CCCCCC(O)CO GCXZDAKFJKCPGK-UHFFFAOYSA-N 0.000 claims description 3
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 claims description 3
- KUQWZSZYIQGTHT-UHFFFAOYSA-N hexa-1,5-diene-3,4-diol Chemical compound C=CC(O)C(O)C=C KUQWZSZYIQGTHT-UHFFFAOYSA-N 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 claims description 3
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 claims description 3
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims description 3
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 3
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 3
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 claims description 3
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 claims description 3
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 claims description 3
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 claims description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 2
- GWQHGNJGONBJPS-UHFFFAOYSA-N [2-[[3-but-3-enoyloxy-2,2-bis(but-3-enoyloxymethyl)propoxy]methyl]-2-(but-3-enoyloxymethyl)-3-hydroxypropyl] but-3-enoate Chemical compound C=CCC(=O)OCC(COC(=O)CC=C)(CO)COCC(COC(=O)CC=C)(COC(=O)CC=C)COC(=O)CC=C GWQHGNJGONBJPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004566 building material Substances 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- CEKJAYFBQARQNG-UHFFFAOYSA-N cadmium zinc Chemical compound [Zn].[Cd] CEKJAYFBQARQNG-UHFFFAOYSA-N 0.000 description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 17
- 239000012948 isocyanate Substances 0.000 description 16
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 15
- 150000002513 isocyanates Chemical class 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 11
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 9
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
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- 229910052797 bismuth Inorganic materials 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
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- 239000000654 additive Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 6
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- 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
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- C08G18/3206—Polyhydroxy compounds aliphatic
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
(a)少なくとも1種の(環式)脂肪族ジイソシアネート及び/又はポリイソシアネート、
(b1)700g/モル未満のモル質量を有する少なくとも1種の(環式)脂肪族ジオール、
(b2)700〜2000の重量平均分子量Mwを有し、かつ好ましくは20mgKOH/g以下のDIN53240に則った酸価を有する、少なくとも1種のポリエステルジオール、
(c)少なくとも1個のイソシアネート反応性基とフリーラジカル重合可能な少なくとも1個の不飽和基を有する少なくとも1種の化合物(c)、
(d)少なくとも1個のイソシアネート反応性基と少なくとも1個の酸基を有する少なくとも1種の化合物、
(e)成分(d)の酸基の少なくとも部分的な中和のための少なくとも1種のアルカリ金属塩基、
(f)任意に、ちょうど1個のヒドロキシル官能基を有する少なくとも1種のモノアルコール、又は少なくとも1種のモノ−C1〜C4−アルキルアミン及びジ−C1〜C4−アルキルアミン、
(g)少なくとも1種の単官能性ポリアルキレンオキシドポリエーテルアルコール
から形成された、放射線硬化性、水分散性のウレタン(メタ)アクリレート(A)によって解決された。
1)イソシアヌレート基を有し、かつ芳香族、脂肪族及び/又は環式脂肪族ジイソシアネートから誘導されたポリイソシアネート。ここで特に好ましいのは、相応の脂肪族及び/又は環式脂肪族イソシアナト−イソシアヌレート並びにとりわけヘキサメチレンジイソシアネート及びイソホロンジイソシアネートを基礎とするものである。これらの考慮されるイソシアヌレートは、とりわけトリス−イソシアナトアルキルイソシアヌレート及び/若しくはトリス−イソシアナトシクロアルキルイソシアヌレート(これらはジイソシアネートの環状三量体である)であるか、又は1個超のイソシアヌレート環を含有するそれらの高級同族体との混合物である。これらのイソシアナトイソシアヌレートは、一般に10〜30重量%、とりわけ15〜25重量%のNCO含有率、及び2.6〜8の平均NCO官能価を有する。
2)芳香族、脂肪族及び/又は環式脂肪族に結合された、好ましくは脂肪族及び/又は環式脂肪族に結合されたイソシアネート基を有するウレトジオンジイソシアネート、とりわけヘキサメチレンジイソシアネート又はイソホロンジイソシアネートから誘導されたもの。ウレトジオンジイソシアネートは、ジイソシアネートの環状二量化生成物である。これらのウレトジオンジイソシアネートは、単独成分として又は他のポリイソシアネート、とりわけ1)で規定されたポリイソシアネートとの混合物において用いられることができる。
3)ビウレット基を有し、かつ芳香族、環式脂肪族又は脂肪族に結合された、好ましくは環式脂肪族又は脂肪族に結合されたイソシアネート基を有するポリイソシアネート、殊にトリス(6−イソシアナトヘキシル)ビウレット又はその高級同族体とのその混合物である。ビウレット基を有するこれらのポリイソシアネートは、一般に18〜22重量%のNCO含有率及び2.8〜4.5の平均NCO官能価を有する。
4)ウレタン基及び/又はアロファネート基を有し、かつ芳香族、脂肪族又は環式脂肪族に結合された、好ましくは脂肪族又は環式脂肪族に結合されたイソシアネート基を有するポリイソシアネートは、例えば、過剰量のヘキサメチレンジイソシアネート又はイソホロンジイソシアネートを、一価若しくは多価アルコール、例えばメタノール、エタノール、イソプロパノール、n−プロパノール、n−ブタノール、イソブタノール、s−ブタノール、t−ブタノール、n−ヘキサノール、n−ヘプタノール、n−オクタノール、n−デカノール、n−ドデカノール(ラウリルアルコール)、2−エチルヘキサノール、n−ペンタノール、ステアリルアルコール、セチルアルコール、ラウリルアルコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、プロパン−1,3−ジオールモノメチルエーテル、シクロペンタノール、シクロヘキサノール、シクロオクタノール、シクロドデカノール、トリメチロールプロパン、ネオペンチルグリコール、ペンタエリトリトール、ブタン−1,4−ジオール、ヘキサン−1,6−ジオール、プロパン−1,3−ジオール、2−エチルプロパン−1,3−ジオール、2−メチルプロパン−1,3−ジオール、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ペンタエチレングリコール、グリセロール、1,2−ジヒドロキシプロパン、2,2−ジメチルエタン−1,2−ジオール、ブタン−1,2−ジオール、ブタン−1,4−ジオール、3−メチルペンタン−1,5−ジオール、2−エチルヘキサン−1,3−ジオール、2,4−ジエチルオクタン−1,3−ジオール、ヒドロキシピバル酸ネオペンチルグリコールエステル、ジメチルロールプロパン、ジペンタエリトリトール、2,2−ビス(4−ヒドロキシシクロヘキシル)プロパン、シクロヘキサン−1,1−ジメタノール、シクロヘキサン−1,2−ジメタノール、シクロヘキサン−1,3−ジメタノール及びシクロヘキサン−1,4−ジメタノール、シクロヘキサン−1,2−ジオール、シクロヘキサン−1,3−ジオール若しくはシクロヘキサン−1,4−ジオール、又はそれらの混合物と反応させることによって得られることができる。ウレタン基及び/又はアロファネート基を有するこれらのポリイソシアネートは、一般に12〜20重量%のNCO含有率及び2.5〜4.5の平均NCO官能価を有する。
5)オキサジアジントリオン基を有し、好ましくはヘキサメチレンジイソシアネート又はイソホロンジイソシアネートから誘導されたポリイソシアネート。オキサジアジントリオン基を有するこの種のポリイソシアネートは、ジイソシアネートと二酸化炭素から得られることができる。
6)イミノオキサジアジンジオン基を有し、好ましくはヘキサメチレンジイソシアネート又はイソホロンジイソシアネートから誘導されたポリイソシアネート。イミノオキサジアジン基を有するこの種のポリイソシアネートは、特定の触媒を用いてジイソシアネートから製造されることができる。
7)ウレトンイミン変性ポリイソシアネート。
8)カルボジイミド変性ポリイソシアネート。
9)例えばDE−A−110013186又はDE−A−110013187から公知の種類の超分岐ポリイソシアネート。
10)ジイソシアネート及び/又はポリイソシアネートとアルコールとからのポリウレタン−ポリイソシアネートプレポリマー。
11)ポリウレア−ポリイソシアネートプレポリマー。
R5は、二価のアルキレン基であって、炭素原子2〜12個を有し、かつ任意にC1〜C4−アルキル基によって置換されていてよく及び/又は1個以上の酸素原子によって中断されていてよい、好ましくは炭素原子2〜10個、より好ましくは炭素原子2〜8個、最も好ましくは炭素原子3〜6個を有する二価のアルキレン基であり、
R6は、二価のアルキレン基又はシクロアルキレン基であって、炭素原子2〜20個を有し、かつ任意にC1〜C4−アルキル基によって置換されていてよく及び/又は1個以上の酸素原子によって中断されていてよい、好ましくは炭素原子4〜15個、より好ましくは炭素原子6〜13個を有する二価のアルキレン基又はシクロアルキレン基であり、
R7は、水素又はメチル、好ましくは水素であり、かつ
Xは、2〜6、好ましくは2〜4の統計的平均を有する正の数である]
を満たすポリイソシアネートである。
− モノマー型或いはポリマー型の相応の無水物、
− モノアルキルエステル若しくはジアルキルエステル、好ましくはモノ−C1〜C4−アルキルエステル若しくはジ−C1〜C4−アルキルエステル、より好ましくはモノメチルエステル若しくはジメチルエステル又は相応のモノエチルエステル若しくはジエチルエステル、
− 或いはモノビニルエステル及びジビニルエステル、並びに
− 混合エステル、好ましくは異なるC1〜C4−アルキル成分との混合エステル、より好ましくは混合メチルエチルエステル
を意味すると解される。
RG−R3−DG
[式中、
RGは、少なくとも1個のイソシアネート反応性基であり、
DGは、少なくとも1個の分散性基であり、かつ
R3は、炭素原子1〜20個を有する、脂肪族、環式脂肪族又は芳香族の基である]
を有する化合物である。
R18−O−H
のモノヒドロキシ化合物又は一般式
R16R17N−H
の第二級モノアミン
[式中、
R16、R17及びR18は、互いに無関係にC1〜C18−アルキル、C2〜C18−アルキルであって、任意に1個以上の酸素原子及び/若しくは硫黄原子及び/若しくは1個以上の置換された若しくは非置換のイミノ基によって中断された前述のアルキル、C6〜C12−アリール、C5〜C12−シクロアルキル又は酸素原子、窒素原子及び/若しくは硫黄原子を有する5〜6員の複素環であるか、又はR16及びR17は一緒になって、任意に1個以上の酸素原子及び/若しくは硫黄原子及び/若しくは1個以上の置換された若しくは非置換のイミノ基によって中断された不飽和、飽和又は芳香族の環を形成し、ここで、言及された基はそれぞれ、官能基のアリール、アルキル、アリールオキシ、アルキルオキシ、ハロゲン、ヘテロ原子及び/又は複素環によって置換されていてよい]である。
R18−O−[−Xi−]s−H
[式中、
R18は、上で定義されたとおりであり、
sは、2〜90、好ましくは5〜45、より好ましくは7〜40、最も好ましくは10〜30の整数であり、かつ
i=1〜sにおけるすべてのXiは、独立して、−CH2−CH2−O−、−CH2−CH(CH3)−O−、−CH(CH3)−CH2−O−、−CH2−C(CH3)2−O−、−C(CH3)2−CH2−O−、−CH2−CHVin−O−、−CHVin−CH2−O−、−CH2−CHPh−O−及び−CHPh−CH2−O−から成る群から、好ましくは−CH2−CH2−O−、−CH2−CH(CH3)−O−及び−CH(CH3)−CH2−O−から成る群から選択されてよく、より好ましくは−CH2−CH2−O−であり、
ここで、Phはフェニルであり、かつVinはビニルである]
の化合物である。
(a)(a1)及び(a2)の総計で100モル%のイソシアネート官能基、
(b)(b1)及び(b2)の総計で((a)におけるイソシアネート官能基に対して)5〜35モル%、好ましくは15〜35モル%のヒドロキシル官能基、
(c)((a)におけるイソシアネート官能基に対して)20〜80モル%、好ましくは30〜70モル%のヒドロキシル官能基、
(d)((a)におけるイソシアネート官能基に対して)20〜60モル%、好ましくは25〜50モル%のヒドロキシル官能基、
(e)((d)における酸官能基に対して)60〜100モル%、好ましくは80〜100モル%の塩基、
(f)((a)におけるイソシアネート官能基に対して)0〜30モル%、好ましくは5〜30モル%、より好ましくは10〜25モル%の、イソシアネートと反応するヒドロキシル官能基又はアミノ官能基、
(g)((a)におけるイソシアネート官能基に対して)0.5〜10モル%、好ましくは1〜5モル%のヒドロキシル官能基であって、
ただし、成分(b)、(c)、(d)及び(g)におけるイソシアネート反応性基の総計は、((a)におけるイソシアネート官能基に対して)イソシアネート反応性基70〜100モル%、好ましくは75〜100モル%、より好ましくは80〜100モル%である。成分(b)、(c)、(d)及び(g)の反応は、好ましくは、成分(f)の添加によって60〜100%、より好ましくは70〜100%、最も好ましくは75〜100%のイソシアネート基の変換率で停止されることができる。
R1及びR2は、互いに無関係に水素又はC1〜C18−アルキル、好ましくはC1〜C4−アルキルであって、任意にアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されたアルキルであり、
k、l、m、qは、互いに無関係に、1〜10、好ましくは1〜5、より好ましくは1〜3の整数であり、かつ
i=1〜k、1〜l、1〜m及び1〜qにおけるすべてのXiは、独立して、−CH2−CH2−O−、−CH2−CH(CH3)−O−、−CH(CH3)−CH2−O−、−CH2−C(CH3)2−O−、−C(CH3)2−CH2−O−、−CH2−CHVin−O−、−CHVin−CH2−O−、−CH2−CHPh−O−及び−CHPh−CH2−O−から成る群から、好ましくは−CH2−CH2−O−、−CH2−CH(CH3)−O−及び−CH(CH3)−CH2−O−から成る群から選択されてよく、より好ましくは−CH2−CH2−O−であり、
ここで、Phはフェニルであり、かつVinはビニルである]
の化合物のアクリレートである。
− モノアゾ顔料:C.I.ピグメントブラウン25;C.I.ピグメントオレンジ5、13、36及び67;C.I.ピグメントレッド1、2、3、5、8、9、12、17、22、23、31、48:1、48:2、48:3、48:4、49、49:1、52:1、52:2、53、53:1、53:3、57:1、63、112、146、170、184、210、245及び251;C.I.ピグメントイエロー1、3、73、74、65、97、151及び183;
− ジスアゾ顔料:C.I.ピグメントオレンジ16、34及び44;C.I.ピグメントレッド144、166、214及び242;C.I.ピグメントイエロー12、13、14、16、17、81、83、106、113、126、127、155、174、176及び188;
− アンタントロン顔料:C.I.ピグメントレッド168(C.I.バットオレンジ3);
− アントラキノン顔料:C.I.ピグメントイエロー147及び177;C.I.ピグメントバイオレット31;
− アントラキノン顔料:C.I.ピグメントイエロー147及び177;C.I.ピグメントバイオレット31;
− アントラピリミジン顔料:C.I.ピグメントイエロー108(C.I.バットイエロー20);
− キナクリドン顔料:C.I.ピグメントレッド122、202及び206;C.I.ピグメントバイオレット19;
− キノフタロン顔料:C.I.ピグメントイエロー138;
− ジオキサジン顔料:C.I.ピグメントバイオレット23及び37;
− フラバントロン顔料:C.I.ピグメントイエロー24(C.I.バットイエロー1);
− インダントロン顔料:C.I.ピグメントブルー60(C.I.バットブルー4)及び64(C.I.バットブルー6);
− イソインドリン顔料:C.I.ピグメントオレンジ69;C.I.ピグメントレッド260;C.I.ピグメントイエロー139及び185;
− イソインドリノン顔料:C.I.ピグメントオレンジ61;C.I.ピグメントレッド257及び260;C.I.ピグメントイエロー109、110、173及び185;
− イソビオラントロン顔料:C.I.ピグメントバイオレット31(C.I.バットバイオレット1);
− 金属錯体顔料:C.I.ピグメントイエロー117、150及び153;C.I.ピグメントグリーン8;
− ペリノン顔料:C.I.ピグメントオレンジ43(C.I.バットオレンジ7);C.I.ピグメントレッド194(C.I.バットレッド15);
− ペリレン顔料:C.I.ピグメントブラック31及び32;C.I.ピグメントレッド123、149、178、179(C.I.バットレッド23)、190(C.I.バットレッド29)及び224;C.I.ピグメントバイオレット29;
− フタロシアニン顔料:C.I.ピグメントブルー15、15:1、15:2、15:3、15:4、15:6及び16;C.I.ピグメントグリーン7及び36;
− ピラントロン顔料:C.I.ピグメントオレンジ51;C.I.ピグメントレッド216(C.I.バットオレンジ4);
− チオインジゴ顔料:C.I.ピグメントレッド88及び181(C.I.バットレッド1);C.I.ピグメントバイオレット38(C.I.バットバイオレット3);
− トリアリールカルボニウム顔料:C.I.ピグメントブルー1、61及び62;C.I.ピグメントグリーン1;C.I.ピグメントレッド81、81:1及び169;C.I.ピグメントバイオレット1、2、3及び27;C.I.ピグメントブラック1(アニリンブラック);C.I.ピグメントイエロー101(アルダジンイエロー);C.I.ピグメントブラウン22;
無機顔料:
− 白色顔料:二酸化チタン(C.I.ピグメントホワイト6)、亜鉛白、顔料グレードの酸化亜鉛、硫酸バリウム、硫化亜鉛;鉛白;炭酸カルシウム;
− 黒色顔料:酸化鉄黒(C.I.ピグメントブラック11)、鉄−マンガンブラック、スピネルブラック(C.I.ピグメントブラック27);カーボンブラック(C.I.ピグメントブラック7);
− 有色顔料:酸化クロム、酸化クロム水和物グリーン、クロムグリーン(C.I.ピグメントグリーン48);コバルトグリーン(C.I.ピグメントグリーン50);ウルトラマリングリーン;コバルトブルー(C.I.ピグメントブルー28及び36);ウルトラマリンブルー;紺青(C.I.ピグメントブルー27);マンガンブルー;ウルトラマリンバイオレット;コバルトバイオレット及びマンガンバイオレット;酸化鉄赤(C.I.ピグメントレッド101);スルホセレン化カドミウム(C.I.ピグメントレッド108);モリブデンレッド(C.I.ピグメントレッド104);ウルトラマリンレッド;
酸化鉄ブラウン、混合ブラウン、スピネル相及びコランダム相(C.I.ピグメントブラウン24、29及び31)、クロムオレンジ;
酸化鉄イエロー(C.I.ピグメントイエロー42);ニッケルチタンイエロー(C.I.ピグメントイエロー53;C.I.ピグメントイエロー157及び164);クロムチタンイエロー、硫化カドミウム及び硫化カドミウム亜鉛(C.I.ピグメントイエロー37及び35);クロムイエロー(C.I.ピグメントイエロー34)、亜鉛黄、クロム酸アルカリ土類金属、ネープルスイエロー;バナジン酸ビスマス(C.I.ピグメントイエロー184);
− 干渉顔料:被覆された金属小片に基づく金属効果顔料;金属酸化物で被覆された雲母小片に基づく真珠光沢顔料、液晶顔料。
撹拌槽中で、ジメチロールプロピオン酸69部、ネオペンチルグリコール19部、Lupraphen(登録商標)VP9327(BASF SE;アジピン酸、イソフタル酸及びシクロヘキサンジメタノールを基礎とし、140mgKOH/gの平均OH価を有するポリエステルジオール)144部、2−ヒドロキシエチルアクリレート29部、Pluriol(登録商標)A1020E(BASF SE;メタノール出発の、50mgKOH/gの平均OH価を有するポリエチレングリコール)62部及びKerobit(登録商標)TBK(BASF SE;2,6−ジ−t−ブチルクレゾール)1部を、アセトン350部に溶解して均質化し、それに続けてLaromer(登録商標)LR9000(BASF SE;2−ヒドロキシエチルアクリレート及びヘキサメチレンジイソシアネートを基礎とし、約290g/モルのイソシアネート当量を有する不飽和ポリイソシアネート)463部とヘキサメチレンジイソシアネート35部とを20分以内で並行して計量添加した。この反応混合物を65℃に加熱し、そしてNCO 0.9重量%の残留イソシアネート含有率に下がるまで反応を続けた。得られたプレポリマーをアセトン300部で希釈した後、残留イソシアネート含分をジエタノールアミン25部との反応によって変換させた。反応混合物を10%水酸化ナトリウム水溶液203部で中和し、そして水1200部の添加により分散させた後、アセトンを留去して、固形分39重量%、pH7.5、粘度300mPa・s及び12000g/モルの重量平均分子量を有する分散液を得た。
撹拌槽中で、ジメチロールプロピオン酸41部、ネオペンチルグリコール11部、Lupraphen(登録商標)VP9327(BASF SE;アジピン酸、イソフタル酸及びシクロヘキサンジメタノールを基礎とし、140mgKOH/gの平均OH価を有するポリエステルジオール)86部、2−ヒドロキシエチルアクリレート17部、Pluriol(登録商標)A1020E(BASF SE;メタノール出発の、50mgKOH/gの平均OH価を有するポリエチレングリコール)37部及びKerobit(登録商標)TBK(BASF SE;2,6−ジ−t−ブチルクレゾール)0.5部を、アセトン210部に溶解して均質化し、それに続けてLaromer(登録商標)LR9000(BASF SE;2−ヒドロキシエチルアクリレート及びヘキサメチレンジイソシアネートを基礎とし、約290g/モルのイソシアネート当量を有する不飽和ポリイソシアネート)278部とヘキサメチレンジイソシアネート21部とを20分以内で並行して計量添加した。この反応混合物を65℃に加熱し、そしてNCO 0.9重量%の残留イソシアネート含有率に下がるまで反応を続けた。得られたプレポリマーをアセトン200部で希釈した後、残留イソシアネート含分をジエタノールアミン14部との反応によって変換させた。反応混合物を水中トリエチルアミン32部で中和し、そして水810部の添加により分散させた後、アセトンを留去して、固形分39重量%、pH7.4、粘度1100mPa・s及び23000g/モルの重量平均分子量を有する分散液を得た。
撹拌槽中で、ジメチロールプロピオン酸44部、ネオペンチルグリコール12部、Lupraphen(登録商標)VP9327(BASF SE;アジピン酸、イソフタル酸及びシクロヘキサンジメタノールを基礎とし、140mgKOH/gの平均OH価を有するポリエステルジオール)92部、2−ヒドロキシエチルアクリレート23部及びKerobit(登録商標)TBK(BASF SE;2,6−ジ−t−ブチルクレゾール)0.5部を、アセトン210部に溶解して均質化し、それに続けてLaromer(登録商標)LR9000(BASF SE;2−ヒドロキシエチルアクリレート及びヘキサメチレンジイソシアネートを基礎とし、約290g/モルのイソシアネート当量を有する不飽和ポリイソシアネート)296部とヘキサメチレンジイソシアネート22部とを20分以内で並行して計量添加した。この反応混合物を65℃に加熱し、そしてNCO 0.9重量%の残留イソシアネート含有率に下がるまで反応を続けた。得られたプレポリマーをアセトン200部で希釈した後、残留イソシアネート含分をジエタノールアミン17部との反応によって変換させた。反応混合物をトリエチルアミン33部で中和し、そして水810部の添加により分散させた後、アセトンを留去して、固形分39重量%、pH7.6、粘度3300mPa・s及び38000g/モルの重量平均分子量を有する分散液を得た。
Claims (15)
- 放射線硬化性で水分散性のウレタン(メタ)アクリレート(A)であって、実質的に
(a)少なくとも1種の(環式)脂肪族ジイソシアネート及び/又はポリイソシアネート、
(b1)700g/モル未満のモル質量を有する少なくとも1種の(環式)脂肪族ジオール、
(b2)700〜2000の重量平均分子量Mwを有する、少なくとも1種のポリエステルジオール、
(c)少なくとも1個のイソシアネート反応性基とフリーラジカル重合可能な少なくとも1個の不飽和基を有する少なくとも1種の化合物(c)、
(d)少なくとも1個のイソシアネート反応性基と少なくとも1個の酸基を有する少なくとも1種の化合物、
(e)成分(d)の酸基の少なくとも部分的な中和のための少なくとも1種のアルカリ金属塩基、
(f)任意に、ちょうど1個のヒドロキシル官能基を有する少なくとも1種のモノアルコール、少なくとも1種のモノ−若しくはジ−C1〜C4−アルキルアミン、又は少なくとも1種のモノ−若しくはジ−アルカノールアミン、
(g)少なくとも1種の単官能性ポリアルキレンオキシドポリエーテルアルコール
から形成された、前記ウレタン(メタ)アクリレート(A)。 - 成分(a)が、環式脂肪族又は脂肪族のモノマージイソシアネート(a1)と、環式脂肪族又は脂肪族のモノマージイソシアネートを基礎とするポリイソシアネート(a2)との混合物である、請求項1記載のウレタン(メタ)アクリレート。
- 成分(a1)が、ヘキサンメチレンジイソシアネート、1,3−ビス(イソシアナトメチル)シクロヘキサン、イソホロンジイソシアネート及び4,4’−又は2,4’−ジ(イソシアナトシクロヘキシル)メタンから成る群から選択される、請求項2記載のウレタン(メタ)アクリレート。
- ポリイソシアネート(a2)が、イソシアヌレート基を有するポリイソシアネート、ウレトジオンジイソシアネート、ビウレット基を有するポリイソシアネート、ウレタン基を有するポリイソシアネート、又はアロファネート基を有するポリイソシアネートである、請求項2又は3記載のウレタン(メタ)アクリレート。
- ポリイソシアネート(a2)が、式
R5は、二価のアルキレン基であって、炭素原子2〜12個を有し、かつ任意にC1〜C4−アルキル基によって置換されていてよく及び/又は1個以上の酸素原子によって中断されていてよい、前記二価のアルキレン基であり、
R6は、二価のアルキレン基又はシクロアルキレン基であって、炭素原子2〜20個を有し、かつ任意にC1〜C4−アルキル基によって置換されていてよく及び/又は1個以上の酸素原子によって中断されていてよい、前記二価のアルキレン基又はシクロアルキレン基であり、
R7は、水素又はメチルであり、かつ
Xは、2〜6の統計的平均を有する正の数である]
の化合物である、請求項2から4までのいずれか1項記載のウレタン(メタ)アクリレート。 - 成分(b1)が、エチレングリコール、プロパン−1,2−ジオール、プロパン−1,3−ジオール、ブタン−1,2−ジオール、ブタン−1,3−ジオール、ブタン−1,4−ジオール、ブタン−2,3−ジオール、ペンタン−1,2−ジオール、ペンタン−1,3−ジオール、ペンタン−1,4−ジオール、ペンタン−1,5−ジオール、ペンタン−2,3−ジオール、ペンタン−2,4−ジオール、ヘキサン−1,2−ジオール、ヘキサン−1,3−ジオール、ヘキサン−1,4−ジオール、ヘキサン−1,5−ジオール、ヘキサン−1,6−ジオール、ヘキサン−2,5−ジオール、ヘプタン−1,2−ジオール、ヘプタン−1,7−ジオール、オクタン−1,8−ジオール、オクタン−1,2−ジオール、ノナン−1,9−ジオール、デカン−1,2−ジオール、デカン−1,10−ジオール、ドデカン−1,2−ジオール、ドデカン−1,12−ジオール、1,5−ヘキサジエン−3,4−ジオール、ネオペンチルグリコール、2−ブチル−2−エチルプロパン−1,3−ジオール、2−メチルペンタン−2,4−ジオール、2,4−ジメチルペンタン−2,4−ジオール、2−エチルヘキサン−1,3−ジオール、2,5−ジメチルヘキサン−2,5−ジオール、2,2,4−トリメチルペンタン−1,3−ジオール、ピナコール、ジエチレングリコール、トリエチレングリコール、ジプロピレングリコール、及びトリプロピレングリコールから成る群から選択されることを特徴とする、請求項1から5までのいずれか1項記載のウレタン(メタ)アクリレート。
- 成分(b2)が、700〜2000の重量平均分子量Mwを有し、かつ20mg KOH/g以下のDIN53240に則った酸価を有する、請求項1から6までのいずれか1項記載のウレタン(メタ)アクリレート。
- 成分(c)が、2−ヒドロキシエチルアクリレート、2−ヒドロキシエチルメタクリレート、2−又は3−ヒドロキシプロピルアクリレート、ブタン−1,4−ジオールモノアクリレート、グリセロールの1,2−又は1,3−ジアクリレート、トリメチロールプロパンジアクリレート、ペンタエリトリチルトリアクリレート、ジトリメチロールプロパントリアクリレート及びジペンタエリトリチルペンタアクリレートから成る群から選択される、請求項1から7までのいずれか1項記載のウレタン(メタ)アクリレート。
- 成分(d)が、ジメチロールプロピオン酸である、請求項1から8までのいずれか1項記載のウレタン(メタ)アクリレート。
- 成分(f)が、モノ−C1〜C4−アルキルアミン、ジ−C1〜C4−アルキルアミン、モノアルカノールアミン又はジアルカノールアミンである、請求項1から9までのいずれか1項記載のウレタン(メタ)アクリレート。
- 成分(f)が、ジエチルアミン、ジ−n−ブチルアミン、エタノールアミン、プロパノールアミン、N,N−ジプロパノールアミン及びN,N−ジエタノールアミンから成る群から選択される、請求項1から10までのいずれか1項記載のウレタン(メタ)アクリレート。
- 水性コーティング組成物であって、
− 請求項1から11までのいずれか1項記載の少なくとも1種のウレタン(メタ)アクリレート、
− 任意に、前記ウレタン(メタ)アクリレート(A)の水性分散液中に溶解又は分散し得る少なくとも1種の低分子量の(メタ)アクリレート(B)、
− 任意に少なくとも1種の顔料、及び
− 任意に少なくとも1種の光開始剤
を含有する、前記水性コーティング組成物。 - 木材、紙、テキスタイル、皮革、フリース、プラスチック表面、ガラス、セラミック、鉱物性建材、セメントブロック、繊維セメント板、金属及び被覆された金属をコーティングするための、請求項12記載のコーティング組成物の使用。
- 印刷インキとしての、請求項12記載のコーティング組成物の使用。
- 請求項14記載の印刷インキを用いて、ポリカーボネート、ポリエチレン、ポリプロピレン、ポリアミド、ポリエチレンテレフタレート(PET)及び紙を印刷する方法。
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PCT/EP2014/067880 WO2015028397A1 (en) | 2013-08-26 | 2014-08-22 | Radiation-curable water-dispersible polyurethane (meth)acrylates |
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US (1) | US10131814B2 (ja) |
EP (1) | EP3039048B1 (ja) |
JP (1) | JP6436996B2 (ja) |
KR (1) | KR20160051814A (ja) |
CN (1) | CN105683235B (ja) |
CA (1) | CA2922235A1 (ja) |
ES (1) | ES2707369T3 (ja) |
RU (1) | RU2673466C2 (ja) |
TR (1) | TR201819125T4 (ja) |
WO (1) | WO2015028397A1 (ja) |
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EP3294817B1 (en) | 2015-10-28 | 2019-11-27 | Hewlett-Packard Development Company, L.P. | Radiation curable polyurethane-based binder dispersion |
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JP6537637B2 (ja) * | 2016-02-05 | 2019-07-03 | 富士フイルム株式会社 | 水分散物及びその製造方法、並びに画像形成方法 |
EP3491080A4 (en) * | 2016-07-27 | 2020-04-08 | Sun Chemical Corporation | ENERGY CURABLE, ELECTRICALLY INSULATING, WATER-BASED FLUIDS |
WO2018087399A1 (de) * | 2016-11-14 | 2018-05-17 | Covestro Deutschland Ag | Beschichtungszusammensetzungen mit dualer härtung |
US11180604B2 (en) | 2016-12-20 | 2021-11-23 | Prc-Desoto International, Inc. | Polyurethane prepolymers incorporating nonlinear short chain diols and/or soft diisocyanates compositions, and uses thereof |
KR101854429B1 (ko) * | 2016-12-29 | 2018-05-03 | 한화케미칼 주식회사 | 지방족 이소시아네이트의 제조 방법 |
EP3507318B1 (en) | 2017-01-31 | 2022-11-09 | Hewlett-Packard Development Company, L.P. | Reactive polyurethane dispersions |
WO2018143913A1 (en) | 2017-01-31 | 2018-08-09 | Hewlett-Packard Development Company, L.P. | Reactive polyurethane dispersions |
WO2018143922A1 (en) * | 2017-01-31 | 2018-08-09 | Hewlett-Packard Development Company, L.P. | Reactive polyurethane dispersions |
WO2018143919A1 (en) | 2017-01-31 | 2018-08-09 | Hewlett-Packard Development Company, L.P. | Reactive polyurethane dispersions |
CN110475830B (zh) | 2017-04-03 | 2022-03-25 | 富士胶片株式会社 | 油墨组合物及其制造方法、以及图像形成方法 |
CN110475829B (zh) | 2017-04-03 | 2022-09-20 | 富士胶片株式会社 | 油墨组合物及其制造方法、以及图像形成方法 |
JP6787493B2 (ja) * | 2017-07-21 | 2020-11-18 | Dic株式会社 | 組成物及び印刷インキ |
WO2019078827A1 (en) * | 2017-10-17 | 2019-04-25 | Hewlett-Packard Development Company, L.P. | UV-CURABLE INK JET INKS |
CN107629189A (zh) * | 2017-10-27 | 2018-01-26 | 天津久日新材料股份有限公司 | 一种低粘度聚氨酯丙烯酸酯的制备和应用 |
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CN113825874B (zh) * | 2019-04-23 | 2024-04-16 | 巴斯夫涂料有限公司 | 使用辐射固化油墨在非织造纺织品基材上印刷的方法 |
CN111253547A (zh) * | 2020-01-21 | 2020-06-09 | 武汉工程大学 | 一种磺酸盐型紫外光固化水性聚氨酯及其制备方法 |
KR102123279B1 (ko) * | 2020-03-02 | 2020-06-16 | 표상현 | 부분(메트)아크릴레이트화 폴리올의 분리 방법 및 이를 이용하여 제조된 (메트)아크릴레이트로 관능화된 우레탄-계 물질 |
WO2022008671A1 (en) | 2020-07-10 | 2022-01-13 | Basf Se | Resin-impregnated fibrous material in the form of a sheet or a web |
WO2023001558A1 (en) * | 2021-07-23 | 2023-01-26 | Basf Se | Water-based binder composition and its application in water-based printing ink |
JP7452598B2 (ja) | 2021-10-14 | 2024-03-19 | 荒川化学工業株式会社 | 水系エマルジョン組成物、硬化物及び積層体 |
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WO2023174985A1 (en) * | 2022-03-18 | 2023-09-21 | Basf Se | Re-dispersible or re-soluble aqueous ethylenically unsaturated aqueous polyurethane compositions with improved water-resistance |
CN117511387B (zh) * | 2023-11-22 | 2024-04-30 | 江苏众立生包装科技有限公司 | 含有聚(氨酯-丙烯酸酯)的印刷光油的制备方法 |
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-
2014
- 2014-08-22 WO PCT/EP2014/067880 patent/WO2015028397A1/en active Application Filing
- 2014-08-22 RU RU2016111153A patent/RU2673466C2/ru not_active IP Right Cessation
- 2014-08-22 JP JP2016537242A patent/JP6436996B2/ja not_active Expired - Fee Related
- 2014-08-22 TR TR2018/19125T patent/TR201819125T4/tr unknown
- 2014-08-22 CN CN201480058679.8A patent/CN105683235B/zh active Active
- 2014-08-22 EP EP14755074.3A patent/EP3039048B1/en active Active
- 2014-08-22 ES ES14755074T patent/ES2707369T3/es active Active
- 2014-08-22 CA CA2922235A patent/CA2922235A1/en not_active Abandoned
- 2014-08-22 US US14/914,426 patent/US10131814B2/en active Active
- 2014-08-22 KR KR1020167008020A patent/KR20160051814A/ko not_active Application Discontinuation
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CA2922235A1 (en) | 2015-03-05 |
US10131814B2 (en) | 2018-11-20 |
JP2016529366A (ja) | 2016-09-23 |
KR20160051814A (ko) | 2016-05-11 |
RU2016111153A3 (ja) | 2018-05-29 |
US20160200938A1 (en) | 2016-07-14 |
RU2673466C2 (ru) | 2018-11-27 |
RU2016111153A (ru) | 2017-10-04 |
EP3039048B1 (en) | 2018-10-24 |
CN105683235A (zh) | 2016-06-15 |
ES2707369T3 (es) | 2019-04-03 |
WO2015028397A1 (en) | 2015-03-05 |
CN105683235B (zh) | 2019-08-23 |
EP3039048A1 (en) | 2016-07-06 |
TR201819125T4 (tr) | 2019-01-21 |
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