CN115304954A - 一种凹版印刷油墨树脂及其制备方法 - Google Patents
一种凹版印刷油墨树脂及其制备方法 Download PDFInfo
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- CN115304954A CN115304954A CN202210853035.4A CN202210853035A CN115304954A CN 115304954 A CN115304954 A CN 115304954A CN 202210853035 A CN202210853035 A CN 202210853035A CN 115304954 A CN115304954 A CN 115304954A
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- Prior art keywords
- ink resin
- printing ink
- methacrylate
- acrylate
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 65
- 229920005989 resin Polymers 0.000 title claims abstract description 65
- 238000007646 gravure printing Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000007639 printing Methods 0.000 claims abstract description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
- 229920000570 polyether Polymers 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 238000002156 mixing Methods 0.000 claims description 27
- 238000003756 stirring Methods 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003999 initiator Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 15
- -1 2- (2-isocyanatoethoxy) ethyl Chemical group 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 9
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000007599 discharging Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 5
- 229940011051 isopropyl acetate Drugs 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 4
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 240000000972 Agathis dammara Species 0.000 claims description 3
- 229920002871 Dammar gum Polymers 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 3
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 3
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 claims description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 3
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 3
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 claims description 2
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 claims description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 claims description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 2
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 claims description 2
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 239000000049 pigment Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 238000009736 wetting Methods 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000011127 biaxially oriented polypropylene Substances 0.000 abstract 1
- 229920006378 biaxially oriented polypropylene Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- YENLEHMSMBFUTB-UHFFFAOYSA-N 2-octan-2-ylphenol Chemical compound CCCCCCC(C)C1=CC=CC=C1O YENLEHMSMBFUTB-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IIQWTZQWBGDRQG-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C(C)=C IIQWTZQWBGDRQG-UHFFFAOYSA-N 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
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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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
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Abstract
本发明提供了一种凹版印刷油墨树脂及其制备方法。本发明通过在油墨树脂主链上引入羧基、聚醚等结构，改善了油墨树脂对颜料的润湿分散作用，提高了油墨的展色性和存储稳定性。该油墨树脂广泛适用于BOPP、PE、PVC、CPP等多种基材印刷，具有附着牢度强、抗粘连性好、高光泽等特点。
Description
技术领域
本发明涉及油墨技术领域，特别是一种凹版印刷油墨树脂及其制备方法。
技术背景
近年来，随着人民生活水平的提高，带动了印刷包装工业的增长，塑料凹版印刷油墨逐渐从苯溶性油墨过渡到醇酯溶性油墨，促进了凹版油墨技术及市场的不断发展，引起了科技人员对油墨树脂的广泛研究。专利CN101831049A公开了一种改性聚氨酯油墨的制备方法。专利CN102775576A公开了一种高速印刷机用聚氨酯里印复合油墨用的连接料及其制备方法。专利CN100547041C公开了一种用于凹版印刷的醇水性复合油墨。专利CN100467551C公开了一种无苯醇溶环保塑料印刷油墨及其制备方法。专利CN101899127B公开了一种采用聚氨酯改性丙稀酸树脂及其制备方法。
虽然凹版油墨树脂蓬勃发展，种类越来越繁多，但是多数树脂自身对颜料分散作用较差，需要在油墨制备过程中加入助剂来提高对颜料的分散性。
发明内容
本发明的目的在于提供一种凹版印刷油墨树脂及其制备方法，该凹版油墨树脂对颜料具有良好润湿分散作用。
为了实现上述目的，本发明提供了如下的技术方案 ：
一种凹版印刷油墨树脂，按重量百分比计，该油墨树脂由如下组分制备而成：
引发剂 0.1～0.8wt%
溶剂 40～60wt%
硬单体 5～20wt%
软单体 5～20wt%
功能单体 1～5wt%
异氰酸酯单体 1～5wt%
端羟基聚醚 1～10wt%
催化剂 0.05～0.2wt%
增粘树脂 1～10wt%；
该油墨树脂的制备方法如下：
（1）将30wt％的引发剂和80wt％的溶剂加入反应釜，搅拌均匀后，升温至60～85℃；
（2）待温度稳定后，将硬单体、软单体、功能单体、异氰酸酯单体混合均匀，在2～4小时内均匀滴入反应釜，同时滴加70wt%的引发剂和10wt％的溶剂；
（3）滴加完毕后，保持温度60～85℃，继续搅拌反应2～4小时；
（4）将催化剂和10wt％的溶剂混合，制得催化剂溶液，将催化剂溶液和端羟基聚醚加入上述反应釜中，保持温度60～85℃，继续搅拌反应2～4小时后，加入增粘树脂混合均匀，降至室温后出料，制得该油墨树脂。
需要说明的是，在上述制备步骤中，引发剂按照重量被分为了30wt％、70wt％的两份，步骤（1）中“30wt％的引发剂”即引发剂总重量30％的引发剂，步骤（2）中“70wt%的引发剂” 即引发剂总重量70％的引发剂；溶剂按照重量被分为了80wt％、10wt％、10wt％三份，步骤（1）中“80wt％的溶剂”即溶剂总重量80％的溶剂，步骤（2）和（4）中“10wt％的溶剂” 即溶剂总重量的10％。
进一步的，所述引发剂选自偶氮二异丁腈、偶氮二异庚腈、过氧化二苯甲酰、过氧化苯甲酸特丁酯、过氧化二碳酸二异丙酯、过氧化-2-乙基己酸特戊酯、过氧化-2-乙基己酸叔丁酯、叔丁基过氧化异丁酸酯、特丁基过氧化辛酸酯中任一种或多种。
进一步的，所述溶剂选自乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸丁酯、乙酸仲丁酯中任一种或多种。
进一步的，所述硬单体选自甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸异丙酯、甲基丙烯酸丁酯、甲基丙烯酸异丁酯、甲基丙烯酸环己酯、甲基丙烯酸异冰片酯、苯乙烯、α-甲基苯乙烯、丙烯腈和乙酸乙烯酯中任一种或多种。
进一步的，所述软单体选自丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正辛酯、丙烯酸异辛酯中任一种或多种。
进一步的，所述功能单体选自丙烯酰胺、丙烯酸、丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、马来酸、富马酸、松香酸中任一种或多种。
进一步的，所述异氰酸酯单体选自异氰酸酯丙烯酸乙酯、甲基丙烯酸异氰酸基乙酯、2-(2-异氰酸乙氧基)乙基甲基丙烯酸酯中任一种或多种。
进一步的，所述端羟基聚醚选自脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪酸聚氧乙烯酯、脂肪醇聚氧乙烯醚聚氧丙烯醚、烷基酚聚氧乙烯醚聚氧丙烯醚、脂肪酸聚氧乙烯聚氧丙烯酯中任一种或多种。
进一步的，所述催化剂选自辛酸亚锡、二月桂酸二丁基锡、二丁基氧化锡、四丁基锡、辛酸铅、辛酸钴、辛酸铁、环烷酸锌、钛酸乙酯、钛酸四丁酯中任一种或多种。
进一步的，所述增粘树脂选自古马隆树脂、达玛树脂、C5石油树脂、C9石油树脂、C5/C9共聚石油树脂中任一种或多种。
与现有技术相比，本发明具有以下有益效果：
本发明通过在油墨树脂主链上引入羧基、聚醚等结构，改善了油墨树脂对颜料的润湿分散作用，提高了油墨的展色性和存储稳定性。
具体实施方式
下面通过具体实施例对本发明做进一步的详述，但不应理解为是对本发明保护范围的限制。凡基于上述技术思想，利用本领域普通技术知识和惯用的技术手段所做的修改、替换、变更，均属于本发明的范围。
实施例1
凹版印刷油墨树脂的制备：
（1）将0.01公斤偶氮二异丁腈、0.02公斤偶氮二异庚腈和32公斤乙酸乙酯加入反应釜，搅拌均匀后，升温至60℃；
（2）待温度稳定后，将10公斤甲基丙烯酸甲酯、10公斤甲基丙烯酸丁酯、20公斤丙烯酸正丁酯、5公斤丙烯酸、1公斤异氰酸酯丙烯酸乙酯混合均匀，在3小时内均匀滴入反应釜，同时滴加由0.02公斤偶氮二异丁腈、0.05公斤特丁基过氧化辛酸酯和4公斤乙酸乙酯混合组成的引发剂溶液；
（3）滴加完毕后，保持温度85℃，继续搅拌反应3小时；
（4）将0.05公斤辛酸亚锡和4公斤乙酸乙酯混合，制得催化剂溶液；将催化剂溶液和4公斤异辛醇聚氧乙烯醚、6公斤硬脂酸聚氧乙烯酯加入上述反应釜中，保持温度60℃，继续搅拌反应4小时后，加入1.85公斤古马隆树脂和2公斤C9石油树脂混合均匀，降至室温后出料，制得凹版印刷油墨树脂。
实施例2
凹版印刷油墨树脂的制备：
（1）将0.24公斤的偶氮二异庚腈、20公斤乙酸正丙酯和28公斤乙酸仲丁酯加入反应釜，搅拌均匀后，升温至72.5℃；
（2）待温度稳定后，将12.5公斤甲基丙烯酸乙酯、2公斤丙烯酸异丁酯、3公斤丙烯酸异辛酯、1公斤甲基丙烯酸缩水甘油酯和5公斤甲基丙烯酸异氰酸基乙酯混合均匀，在2小时内均匀滴入反应釜，同时滴加由0.56公斤偶氮二异庚腈和6公斤乙酸正丙酯混合组成的引发剂溶液；
（3）滴加完毕后，保持温度60℃，继续搅拌反应4小时；
（4）将0.2公斤二月桂酸二丁基锡和6公斤乙酸正丙酯混合，制得催化剂溶液；将催化剂溶液和5.5公斤壬基酚聚氧乙烯醚加入上述反应釜中，保持温度85℃，继续搅拌反应2小时后，加入10公斤达玛树脂混合均匀，降至室温后出料，制得凹版印刷油墨树脂。
实施例3
凹版印刷油墨树脂的制备：
（1）将0.135公斤过氧化二苯甲酰和44公斤乙酸丁酯加入反应釜，搅拌均匀后，升温至85℃；
（2）待温度稳定后，将18公斤甲基丙烯酸异冰片酯、12.5公斤丙烯酸叔丁酯、3公斤富马酸、1公斤异氰酸酯丙烯酸乙酯和2公斤2-(2-异氰酸乙氧基)乙基甲基丙烯酸酯混合均匀，在4小时内均匀滴入反应釜，同时滴加由0.315公斤过氧化二苯甲酰和5.5公斤乙酸丁酯混合组成的引发剂溶液；
（3）滴加完毕后，保持温度72.5℃，继续搅拌反应2小时；
（4）将0.2公斤二丁基氧化锡和5.5公斤乙酸丁酯混合，制得催化剂溶液；将催化剂溶液和1公斤仲辛基酚聚氧乙烯醚加入上述反应釜中，保持温度72.5℃，继续搅拌反应3小时后，加入6.85公斤C5石油树脂混合均匀，降至室温后出料，制得凹版印刷油墨树脂。
实施例4
凹版印刷油墨树脂的制备：
（1）将0.21公斤过氧化二碳酸二异丙酯和40公斤乙酸异丙酯加入反应釜，搅拌均匀后，升温至70℃；
（2）待温度稳定后，将8.175公斤甲基丙烯酸环己酯、5公斤丙烯酸乙酯、15公斤丙烯酸异辛酯、5公斤马来酸和5公斤异氰酸酯丙烯酸乙酯混合均匀，在3.5小时内均匀滴入反应釜，同时滴加由0.49公斤过氧化二碳酸二异丙酯和5公斤乙酸异丙酯混合组成的引发剂溶液；
（3）滴加完毕后，保持温度80℃，继续搅拌反应2.5小时；
（4）将0.125公斤钛酸乙酯和5公斤乙酸异丙酯混合，制得催化剂溶液；将催化剂溶液和10公斤仲辛基酚聚氧乙烯醚聚氧丙烯醚加入上述反应釜中，保持温度75℃，继续搅拌反应3.5小时后，加入1公斤C9石油树脂混合均匀，降至室温后出料，制得凹版印刷油墨树脂。
实施例5
凹版印刷油墨树脂的制备：
（1）将0.15公斤叔丁基过氧化异丁酸酯和46.4公斤乙酸正丙酯加入反应釜，搅拌均匀后，升温至65℃；
（2）待温度稳定后，将5公斤甲基丙烯酸异丁酯、15公斤丙烯酸正辛酯、4公斤丙烯酰胺、4公斤甲基丙烯酸异氰酸基乙酯混合均匀，在2.5小时内均匀滴入反应釜，同时滴加由0.35公斤叔丁基过氧化异丁酸酯和5.8公斤乙酸正丙酯混合组成的引发剂溶液；
（3）滴加完毕后，保持温度65℃，继续搅拌反应3.5小时；
（4）将0.1公斤钛酸四丁酯、2.8公斤乙酸正丙酯和3公斤乙酸丁酯混合，制得催化剂溶液；将催化剂溶液和7.9公斤月桂酸聚氧乙烯聚氧丙烯酯加入上述反应釜中，保持温度80℃，继续搅拌反应2.5小时后，加入5.5公斤C5/C9共聚石油树脂混合均匀，降至室温后出料，制得凹版印刷油墨树脂。
实施例6
凹版塑料油墨的制备：
将25公斤实施例4的凹版印刷油墨树脂、12.5公斤乙酸乙酯、12.5公斤钛白粉加入配料器，用高速分散机搅拌30分钟，使其混合均匀；将混合均匀的物料取出，送入砂磨机进行砂磨，待细度低于 10μm后取出，过滤；经检验合格后，包装，制得凹版塑料油墨。
对制备的凹版塑料油墨进行性能检测，主要技术指标如表1所示：
表1
以上检测结果依据 QB/T2024-2012 标准测试。
对比例1
油墨树脂、油墨的制备：
（1）将0.15公斤过氧化二苯甲酰和45公斤乙酸正丙酯加入反应釜，搅拌均匀后，升温至65℃；
（2）待温度稳定后，将21公斤甲基丙烯酸异丙酯、24公斤丙烯酸正丁酯、5公斤马来酸混合均匀，在3小时内均匀滴入反应釜，同时滴加由0.35公斤过氧化二苯甲酰和4.5公斤乙酸正丙酯混合组成的引发剂溶液；
（3）滴加完毕后，保持温度80℃，继续搅拌反应4小时，降至室温后出料，制得油墨树脂；
将25公斤上述油墨树脂、12.5公斤乙酸乙酯、12.5公斤钛白粉加入配料器，用高速分散机搅拌30分钟，使其混合均匀；将混合均匀的物料取出，送入砂磨机进行砂磨，待细度低于 10μm后取出，过滤,制得凹版塑料油墨。
对制备的凹版塑料油墨进行性能检测，主要技术指标如表2所示：
表2
以上检测结果依据 QB/T2024-2012 标准测试。
最后应说明的是：以上各实施例仅用以说明本发明的技术方案，而非对其限制；尽管参照前述各实施例对本发明进行了详细的说明，但本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分或者全部技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本发明各实施例技术方案的范围。
Claims (10)
1.一种凹版印刷油墨树脂，其特征在于，按重量百分比计，该油墨树脂由如下组分制备而成：
引发剂 0.1～0.8wt%
溶剂 40～60wt%
硬单体 5～20wt%
软单体 5～20wt%
功能单体 1～5wt%
异氰酸酯单体 1～5wt%
端羟基聚醚 1～10wt%
催化剂 0.05～0.2wt%
增粘树脂 1～10wt%；
该油墨树脂的制备方法如下：
（1）将30wt％的引发剂和80wt％的溶剂加入反应釜，搅拌均匀后，升温至60～85℃；
（2）待温度稳定后，将硬单体、软单体、功能单体、异氰酸酯单体混合均匀，在2～4小时内均匀滴入反应釜，同时滴加70wt%的引发剂和10wt％的溶剂；
（3）滴加完毕后，保持温度60～85℃，继续搅拌反应2～4小时；
（4）将催化剂和10wt％的溶剂混合，制得催化剂溶液，将催化剂溶液和端羟基聚醚加入上述反应釜中，保持温度60～85℃，继续搅拌反应2～4小时后，加入增粘树脂混合均匀，降至室温后出料，制得该油墨树脂。
2.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述引发剂选自偶氮二异丁腈、偶氮二异庚腈、过氧化二苯甲酰、过氧化苯甲酸特丁酯、过氧化二碳酸二异丙酯、过氧化-2-乙基己酸特戊酯、过氧化-2-乙基己酸叔丁酯、叔丁基过氧化异丁酸酯、特丁基过氧化辛酸酯中任一种或多种。
3.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述溶剂选自乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸丁酯、乙酸仲丁酯中任一种或多种。
4.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述硬单体选自甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸异丙酯、甲基丙烯酸丁酯、甲基丙烯酸异丁酯、甲基丙烯酸环己酯、甲基丙烯酸异冰片酯、苯乙烯、α-甲基苯乙烯、丙烯腈和乙酸乙烯酯中任一种或多种。
5.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述软单体选自丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正辛酯、丙烯酸异辛酯中任一种或多种。
6.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述功能单体选自丙烯酰胺、丙烯酸、丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、马来酸、富马酸、松香酸中任一种或多种。
7.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述异氰酸酯单体选自异氰酸酯丙烯酸乙酯、甲基丙烯酸异氰酸基乙酯、2-(2-异氰酸乙氧基)乙基甲基丙烯酸酯中任一种或多种。
8.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述端羟基聚醚选自脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪酸聚氧乙烯酯、脂肪醇聚氧乙烯醚聚氧丙烯醚、烷基酚聚氧乙烯醚聚氧丙烯醚、脂肪酸聚氧乙烯聚氧丙烯酯中任一种或多种。
9.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述催化剂选自辛酸亚锡、二月桂酸二丁基锡、二丁基氧化锡、四丁基锡、辛酸铅、辛酸钴、辛酸铁、环烷酸锌、钛酸乙酯、钛酸四丁酯中任一种或多种。
10.根据权利要求1所述的凹版印刷油墨树脂，其特征在于，所述增粘树脂选自古马隆树脂、达玛树脂、C5石油树脂、C9石油树脂、C5/C9共聚石油树脂中任一种或多种。
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| CN103772639A (zh) * | 2012-10-21 | 2014-05-07 | 成都市新津托展油墨有限公司 | 一种聚氨酯丙烯酸酯油墨树脂及其制备方法 |
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| CN103772639A (zh) * | 2012-10-21 | 2014-05-07 | 成都市新津托展油墨有限公司 | 一种聚氨酯丙烯酸酯油墨树脂及其制备方法 |
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