WO2022201840A1 - ポリエステル樹脂及びそれを含む活性エネルギー線硬化型インキ組成物、並びにそれらの製造方法 - Google Patents
ポリエステル樹脂及びそれを含む活性エネルギー線硬化型インキ組成物、並びにそれらの製造方法 Download PDFInfo
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- WO2022201840A1 WO2022201840A1 PCT/JP2022/003048 JP2022003048W WO2022201840A1 WO 2022201840 A1 WO2022201840 A1 WO 2022201840A1 JP 2022003048 W JP2022003048 W JP 2022003048W WO 2022201840 A1 WO2022201840 A1 WO 2022201840A1
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- polyester resin
- meth
- acid
- acrylate
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- 230000001133 acceleration Effects 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- FCTPXMGHGVCNMD-UHFFFAOYSA-N cyclohexene-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)=C1 FCTPXMGHGVCNMD-UHFFFAOYSA-N 0.000 description 1
- KAAQPMPUQHKLLE-UHFFFAOYSA-N cyclohexene-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)=CC1 KAAQPMPUQHKLLE-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 description 1
- 229940118781 dehydroabietic acid Drugs 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 235000013410 fast food Nutrition 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010794 food waste Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- KRISBJIGEQYHDD-UHFFFAOYSA-N nonane-2,2-diol Chemical compound CCCCCCCC(C)(O)O KRISBJIGEQYHDD-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
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940010310 propylene glycol dioleate Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000012046 side dish Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- 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
- C09D11/104—Polyesters
-
- 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
Definitions
- the present invention relates to polyester resins, active energy ray-curable ink compositions containing the same, and methods for producing them.
- IG mark is a system in which the ratio of components derived from biomass among the components that make up the ink composition is used as an indicator, and the level of environmental friendliness of the ink composition is ranked in three stages according to the degree. .
- this system can be said to be characterized by promoting the substitution of raw materials derived from fossil resources with raw materials derived from biomass for the purpose of reducing environmental impact.
- Patent Document 2 discloses an ink composition of a type in which a component having an ethylenically unsaturated bond is cured by a radical polymerization system, and further, by adding an epoxidized vegetable oil to the ink composition, low-intensity ultraviolet rays It has been shown that the curability for Considering that epoxy compounds generally do not exhibit radical polymerizability, the above results can be said to be surprising.
- the present invention has been made in view of the above circumstances, and provides a resin for ink compositions that can be used for the preparation of active energy ray-curable ink compositions and that can increase the ratio of biomass-derived components. intended to provide
- oxidized vegetable oil such as waste cooking oil after being used for food processing such as fried foods.
- vegetable oil is a mixture of ester compounds of fatty acids and glycerin, including unsaturated fatty acids such as oleic acid and linoleic acid.
- oxygen is added to some of the unsaturated bonds of the fatty acid to generate a hydroperoxide group (--OOH) in the molecule.
- the hydroperoxide group is a highly polar substituent, so oxidized vegetable oil such as waste cooking oil has higher polarity than virgin vegetable oil.
- an active energy ray-curable ink composition contains a compound having an ethylenically unsaturated bond as a main component in order to provide curability.
- a compound having an ethylenically unsaturated bond a compound having high polarity such as a (meth)acrylic acid ester compound is generally selected. Therefore, in this type of ink composition, the composition as a whole has high polarity, and from the viewpoint of compatibility, oxidized vegetable oils, that is, oils and fats with high polarity as described above, also have high polarity.
- the active energy ray-curable ink composition which is the composition of
- triglycerides such as vegetable oils are also raw materials for polyester resins used as resins for ink compositions. Therefore, if an epoxy group is introduced into oxidized vegetable oil such as waste edible oil as shown in Patent Document 2 and a polyester resin is prepared using this as a raw material, an active energy ray-curable ink composition can be obtained. It is also possible to obtain a component for preparing an ink composition that is highly polar, that is, has good compatibility with an active energy ray-curable ink composition, and contains abundant biomass-derived components.
- waste cooking oil can be used as the oxidized vegetable oil for this polyester resin, and the ink composition using such a polyester resin is more environmentally friendly in terms of effective utilization of waste. It will be a product that can reduce the
- the ink composition containing the polyester resin derived from oxidized vegetable oil has high compatibility due to being composed of highly polar components, and has high fluidity. In addition, it improves the glossiness of the printed matter, and improves the printing workability and the added value of the printed matter.
- the present invention has been completed based on the above findings, and provides the following.
- the present invention is a condensation polymer of a fatty acid containing an epoxy group, an acid component containing a polybasic acid, and a polyhydric alcohol, and the peroxide value when the fatty acid is converted to triglyceride is 1 meq/ A polyester resin characterized by having a weight of 1 kg or more.
- the present invention is the polyester resin according to item (1), which further contains a resin acid as the acid component.
- the present invention is an active energy ray-curable ink composition characterized by containing the polyester resin described in (1) or (2).
- the present invention is a method for producing a polyester resin by heating a mixture containing an epoxidized fat, a polybasic acid and a polyhydric alcohol to cause an ester exchange reaction and a polycondensation reaction, wherein the epoxidation
- the present invention also provides the method for producing a polyester resin according to item (4), wherein the epoxidized fat has an acid value of 0.1 mgKOH/g or more and 100 mgKOH/g or less.
- the present invention also provides the method for producing a polyester resin according to item (4) or (5), wherein the epoxidized fat has a peroxide value of 1 meq/kg or more and 1000 meq/kg or less. .
- the polyester resin according to any one of (4) to (6), wherein the epoxidized oil has an oxirane oxygen concentration of 0.5% or more and 50% or less. is a manufacturing method.
- the present invention is also the method for producing a polyester resin according to any one of items (4) to (7), wherein the mixture further contains a resin acid.
- the present invention also provides the method for producing a polyester resin according to any one of items (4) to (8), wherein the epoxidized fat is an epoxy-modified waste edible oil.
- the present invention provides an active energy ray-curable ink characterized by using the polyester resin produced by the method according to any one of (4) to (9) above as one of its constituent components. It is also a method of manufacturing the composition.
- a resin for ink compositions that can be used for the preparation of active energy ray-curable ink compositions and that can increase the ratio of biomass-derived components.
- the polyester resin is a resin made by condensation polymerization of polybasic acids and polyhydric alcohols
- the polyester resin in the present invention includes, in addition to polybasic acids and polyhydric alcohols, oils and fats as described above. (Fatty acid contained in) is combined and polycondensed.
- Such resins are also called alkyd resins, and therefore the polyester resin in the present invention is synonymous with the alkyd resin.
- the method for producing a polyester resin of the present invention is a method for producing a polyester resin by heating a mixture containing an epoxidized fat, a polybasic acid and a polyhydric alcohol to cause an ester exchange reaction and a polycondensation reaction,
- the epoxidized fat has a peroxide value of 1 meq/kg or more.
- Epoxidized fats and oils are esters of fatty acids and alcohols that have at least one epoxy group.
- fat and oil refers to an ester of fatty acid and glycerin, that is, triglyceride. call.
- alcohol include alcohols having 1 to 14 carbon atoms such as glycerin, methanol, ethanol, propanol, isopropanol, and 2-ethylhexanol, but are not particularly limited.
- a polyhydric alcohol such as glycerin
- at least one fatty acid having at least one epoxy group may be condensed (that is, form an ester bond) in the polyhydric alcohol, and at least one epoxy group may be formed.
- a plurality of fatty acids may be condensed.
- each fatty acid may be selected independently of each other.
- examples of such fats and oils include triglycerides such as vegetable oils and animal oils, and esters (that is, fatty acid esters) of fatty acids derived from vegetable oils, animal oils, and the like with monohydric or dihydric alcohols.
- the production method of the present invention is characterized in that an epoxidized oil having a peroxide value of 1 meq/kg or more is particularly used.
- oils and fats that have been oxidized to contain peroxide groups are highly polar, and when polyester resins are prepared using such oils and fats as raw materials, the resulting polyester resins also contain peroxide groups and are polar. It becomes high, and exhibits high compatibility with an active energy ray-curable ink composition, which also has a high polarity. Therefore, an active energy ray-curable ink composition to which this polyester resin is applied provides high fluidity and improved gloss in printed matter.
- the epoxidized fats and oils are derived from renewable raw materials such as animal oils and vegetable oils, and contribute to increasing the biomass count in the ink composition.
- Epoxidized fats and oils having a peroxide value of 1 meq/kg or more are obtained by epoxidizing fats and oils having a peroxide value of 1 meq/kg or more, that is, triglycerides or fatty acid esters obtained by modifying triglycerides.
- the peroxide value is also called POV (Peroxide Value), and is an index representing the degree of oxidation of fats and oils.
- the peroxide value can be determined by titrating the liberated iodine (I 2 ) with a 0.01N sodium thiosulfate solution by allowing potassium iodide to act on the fat or oil to be measured.
- the hydroperoxide groups contained in fats and oils are replaced with iodine molecules (I 2 ), and titration with sodium thiosulfate is performed using the property that iodine molecules react with starch to turn blue-purple, and the amount until the color disappears is measured. Then, the number of equivalents of sodium thiosulfate consumed by titration can be obtained. Based on the titration result, the milligram equivalent (meq) of the peroxide contained in 1 kg of oil is calculated as the peroxide value (unit: meq/kg).
- Epoxidized fats can be prepared in a variety of ways. For example, when the fat is a triglyceride, the epoxidized fat can be obtained by oxidizing a vegetable oil or animal oil having an unsaturated bond in the fatty acid moiety with an appropriate oxidizing agent or peroxide.
- the epoxidized fat is obtained by reacting a fatty acid having an unsaturated bond with an alcohol (regardless of whether it is a monool or a polyol) to carry out an esterification, transesterification or transesterification reaction.
- Fatty acid esters are obtained by this process, and these fatty acid esters are oxidized with a suitable oxidizing agent or peroxide.
- Epoxidized oils and fats include epoxidized soybean oil (ESO), epoxidized corn oil, epoxidized sunflower oil, epoxidized linseed oil, epoxidized canola oil, epoxidized rapeseed oil, epoxidized safflower oil, epoxidized tall oil, epoxidized Tung oil, epoxidized fish oil, epoxidized beef tallow oil, epoxidized castor oil, epoxidized methyl stearate, epoxidized butyl stearate, epoxidized 2-ethylhexyl stearate, epoxidized stearyl stearate, 3,4-epoxycyclohexylmethyl- Examples include 3,4-epoxycyclohexanecarboxylate epoxidized soybean oil, epoxidized propylene glycol dioleate, epoxidized palm oil, and epoxidized
- waste cooking oil that has been exposed to high temperatures during cooking such as fried food
- waste cooking oil that has been exposed to high temperatures during cooking such as fried food
- oils and fats that have aged and oxidized by standing and oils and fats that have been oxidized by being exposed to direct sunlight also have peroxide groups
- oils and fats that have been oxidized by intentional oxidation can also be epoxidized and used.
- fats and oils to be subjected to epoxidation in addition to edible oils such as salad oil, corn oil, olive oil, soybean oil, corn oil, sunflower oil, canola oil, rapeseed oil, safflower oil, fish oil and beef oil, linseed oil, tung oil, Tall oil, castor oil and the like can be mentioned.
- Fatty acid esters obtained by transesterification of these fats and oils can also be used as fats and oils to be subjected to epoxidation.
- the epoxidized fat in the present invention may be derived from waste cooking oil used for cooking.
- waste edible oil examples include edible oil used after cooking side dishes at each restaurant, fast food, restaurant, convenience store, supermarket, etc., and edible oil used for cooking at home.
- Edible oils that are discarded after being heat-treated at high temperatures such as for cooking fried chicken, potatoes, tempura, etc.
- Employing such an epoxidized fat derived from waste cooking oil can lead to effective utilization of food waste, and can greatly reduce the environmental impact of the ink composition of the present invention.
- the waste cooking oil is not limited to that used for cooking as described above, and may be, for example, cooking oil that has been left under direct sunlight for a long time and has been highly oxidized. Waste cooking oil can also be purchased from a recycling company that collects waste cooking oil from restaurants and the like and recycles it.
- the upper limit of the peroxide value of the epoxidized oil is preferably about 1000 meq/kg, more preferably about 800 meq/kg, and even more preferably about 700 meq/kg.
- the lower limit of the peroxide value of the epoxidized oil is 1 meq/kg as described above, but the lower limit is preferably about 10 meq/kg, more preferably about 30 meq/kg.
- the acidic substituent that gives the acid value also has a high polarity, and a polyester resin derived from fats and oils rich in this has a good phase for an active energy ray-curable ink composition. Soluble. Therefore, the epoxidized fat used in the present invention preferably has a certain amount of acid value.
- the acid value of the epoxidized oil is preferably 0.1 mgKOH/g or more and 100 mgKOH/g or less, more preferably 0.5 mgKOH/g or more and 50 mgKOH/g or less, and 0.5 mgKOH/g. 25 mgKOH/g or less is more preferable.
- the oxirane oxygen concentration which represents the content of epoxy groups contained in the epoxidized fat, is preferably 0.5% or more and 50% or less.
- the oxirane oxygen concentration is more preferably 0.5% or more and 25% or less, and more preferably 1% or more and 10% or less.
- a polybasic acid is a compound having multiple carboxyl groups, and is a component for condensation polymerization with a polyhydric alcohol, which will be described later, to increase the molecular weight.
- the compound having a plurality of carboxy groups those that have been used in the synthesis of polyester resins can be used without limitation, and may be provided with two or three or more carboxy groups, or acid anhydrides thereof.
- Such compounds include phthalic anhydride, isophthalic acid, terephthalic acid, adipic acid, trimellitic acid, 1,2-cyclohexanedicarboxylic acid, 1,2-cyclohexenedicarboxylic acid, 1,3-cyclohexenedicarboxylic acid, 1, 4-cyclohexenedicarboxylic acid, hexahydrophthalic anhydride, 5-sodiosulfoisophthalic acid, fumaric acid, benzoic acid, tert-butylbenzoic acid, tetrahydrophthalic anhydride, maleic anhydride, succinic acid, succinic anhydride, fumaric acid, Sebacic acid, azelaic acid, tetrabromophthalic anhydride, methylhimic anhydride, tetrachlorophthalic anhydride, hexahydrophthalic anhydride, pyromellitic anhydride, trimellitic anhydride, methyl
- Polyhydric alcohols form esters with acid components including fatty acids and polybasic acids generated from the epoxidized fats and oils to increase the molecular weight of these components.
- acid components including fatty acids and polybasic acids generated from the epoxidized fats and oils to increase the molecular weight of these components.
- polyhydric alcohol those that have hitherto been used in the synthesis of polyester resins can be used without limitation, and examples thereof include compounds having two or more hydroxyl groups.
- Such compounds include ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, diethylene glycol, triethylene glycol, polyethylene glycol, dipropylene glycol, 1,3-butanediol.
- neopentyl glycol spiro glycol, dioxane glycol, adamantanediol, 3-methyl-1,5-pentanediol, methyloctanediol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, 2-methylpropanediol 1 , 3,3-methylpentanediol 1,5, hexamethylene glycol, octylene glycol, 9-nonanediol, 2,4-diethyl-1,5-pentanediol, ethylene oxide modified compounds of bifunctional phenols such as bisphenol A , propylene oxide modified compounds of bifunctional phenols such as bisphenol A, ethylene oxide of bisphenol A, propylene oxide copolymerized modified compounds, copolymerized polyether polyols of ethylene oxide and propylene oxide, polycarbonate diols, adamantane
- polyester resin By heating the mixture containing the epoxidized fats and oils, polybasic acid and polyhydric alcohol, transesterification and polycondensation reactions occur to synthesize a polyester resin. At this time, it is preferable that resin acid (rosin) is further included as part of the mixture.
- resin acid Rosin
- the molecule of the prepared polyester resin contains a structure derived from the resin acid, The polyester resin has an improved affinity for pigments, and the proportion of biomass-derived components is increased.
- Resin acids are abietic acid contained in rosins, its isomers, and their derivatives. Rosins are non-volatile components of pine resin collected from plants of the pine family, and are mainly composed of abietic acid and isomers thereof. Examples of abietic acid and its isomers include abietic acid, neoabietic acid, parastric acid, pimaric acid, isopimaric acid, dehydroabietic acid, etc., all of which have a carboxy group, and the above polyhydric alcohols and epoxy It is possible to form an ester with an alcohol produced by transesterification of the oil.
- abietic acid which is a trans-diene compound
- abietic acid which is a trans-diene compound
- a cis-diene compound upon heating.
- the cis-diene compound thus obtained is subjected to a Diels-Alder reaction with a dienophile compound having a plurality of carboxyl groups such as maleic acid and 1,2-cyclohexenedicarboxylic acid to add a plurality of carboxyl groups to the abietic acid skeleton.
- a dienophile compound having a plurality of carboxyl groups such as maleic acid and 1,2-cyclohexenedicarboxylic acid to add a plurality of carboxyl groups to the abietic acid skeleton.
- a polymerized rosin is synthesized by polymerizing a plurality of molecules of abietic acid or its isomers, and such a compound also has a plurality of carboxyl groups.
- the above-mentioned derivatives of abietic acid and its isomers refer to such compounds.
- rosins are mainly composed of resin acids, rosins themselves can be used instead of the above resin acids for synthesis. In the present invention, such rosins are also included in resin acids.
- a plurality of types of rosins are known due to differences in production methods, subsequent chemical treatments, etc., and any of the rosins may be used in the present invention. Examples of such rosins include gum rosin, wood rosin, tall rosin, disproportionated rosin, hydrogenated rosin, polymerized rosin and the like. Further, rosins may be modified by the Diels-Alder reaction as described above. From the viewpoint of storage stability, it is preferable to use rosins that chemically have no or few conjugated double bonds. Examples of such rosins include disproportionated rosin and hydrogenated rosin. Although rosins having conjugated double bonds are slightly inferior in terms of storage stability of synthesized resins, they can be used without problems.
- various fatty acids may be used to synthesize the polyester resin, if necessary.
- fatty acids include caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecyl acid, palmitic acid, margaric acid, stearic acid, oleic acid, linoleic acid, arachidic acid, and behenic acid. can.
- the ratio (%) of the total mass of the fatty acid contained in the epoxidized fat and the fatty acid added as necessary as described above to the mass of the entire polyester resin is called the oil length. From the viewpoint of increasing the biomass component ratio in the obtained polyester resin, it is preferable to use epoxidized fats and oils and fatty acids so that the oil length is about 5 to 85, and epoxidized fats and oils so that the oil length is about 10 to 50. Preference is given to using fatty acids.
- a monobasic acid other than the fatty acid may be added as an acid component.
- Such monobasic acids include benzoic acid, acetic acid, propionic acid, butyric acid and the like.
- a polyester resin is prepared by mixing and heating the above ingredients.
- a reaction vessel charged with these raw materials is fed with an inert gas such as nitrogen gas, and if necessary, a small amount of a solvent such as xylene is added and heated to azeotrope with condensed water.
- a method of polycondensation while removing water can be mentioned.
- the reaction temperature can be about 170 to 250° C., and the reaction time can be about 5 to 25 hours, but is not particularly limited. Completion of the reaction can be determined by monitoring the acid value of the reaction mixture over the course of the reaction time. That is, the reaction may be terminated when the decrease in acid value of the reaction mixture due to polycondensation stops.
- the polycondensation reaction can be carried out in a shorter time by distilling the water produced by the polycondensation out of the system or by using a reaction catalyst.
- the reaction catalyst include triphenylphosphine, tetrabutylzirconate, monobutyltin oxide (monobutyltin oxide), zirconium naphtate, tetrabutyl titanate, and the like.
- the weight-average molecular weight of the polyester resin obtained by condensation polymerization reaction is preferably about 1,000 to 100,000.
- the weight-average molecular weight of polyester resin is determined by the balance between the acid component and the polyhydric alcohol, so the initial synthesis is carried out on a small scale, and after determining the reaction conditions and the types of raw materials, etc., the large-scale synthesis is started. It is desirable to migrate.
- the polyester resin obtained by the polycondensation reaction preferably has an acid value of 1 to 50 mgKOH/g.
- the acid value is preferably 1-25 mg KOH, more preferably 1-10 mg KOH.
- the acid value of the rosin-modified polyester resin at the end of the reaction is determined by the balance between the amounts of the acid component and the polyhydric alcohol. should be carried out on a small scale, and the reaction conditions and the types of raw materials should be determined before proceeding to large-scale synthesis.
- the polyester resin of the present invention is prepared by the production method described above and constitutes one aspect of the present invention.
- the polyester resin of the present invention is a condensation polymer of a fatty acid containing an epoxy group, an acid component containing a polybasic acid, and a polyhydric alcohol, and has a peroxide value of 1 meq/ when the fatty acid is converted to triglyceride. kg or more.
- the description of the portions that overlap with the description of the method for producing a polyester resin already described will be omitted as appropriate.
- the polyester resin of the present invention has high polarity because it is prepared by using an epoxidized oil having a peroxide value of 1 meq/kg or more as one of raw materials, and an active energy ray-curable ink composition composed of similarly highly polar materials. Shows good compatibility with materials. For this reason, the polyester resin of the present invention is preferably used in the preparation of an active energy ray-curable ink composition, and the active energy ray-curable ink composition to which this is applied has high fluidity and glossiness of printed matter. and improve printing workability and the added value of printed matter. Since the polyester resin of the present invention contains a large amount of biomass-derived raw materials, it is possible to increase the content of biomass-derived components in the ink composition containing the polyester resin.
- the polyester resin of the present invention is a condensation polymer of a fatty acid containing an epoxy group, an acid component containing a polybasic acid, and a polyhydric alcohol.
- the fatty acid containing an epoxy group is derived from the epoxidized fat and oil described in the production method of the present invention.
- the mixture containing the epoxidized fat and oil is heated to transesterify the epoxidized fat and oil.
- the peroxide value of the fatty acid converted to triglyceride is 1 meq/kg or more” means that the peroxide value of the epoxidized oil and fat before becoming a fatty acid containing epoxy by transesterification is 1 meq/kg. It means something.
- the polyester resin of the present invention preferably further contains a resin acid as the acid component. Since this has already been described, the description is omitted here.
- An active energy ray-curable ink composition comprising the polyester resin of the present invention is also one aspect of the present invention.
- the polyester resin of the present invention has a high biomass-derived component ratio as a raw material, and an ink composition containing this can increase the biomass-derived component ratio. Therefore, this ink composition has a reduced environmental load and is a product suitable for receiving various environment-related certifications such as IG mark certification.
- the polyester resin of the present invention can also be prepared using epoxidized fats and oils derived from waste cooking oil used for frying, etc. In this case, Furthermore, it is possible to reduce the environmental impact of the ink composition.
- the polyester resin of the present invention has excellent compatibility with the monomers and oligomers contained in the active energy ray-curable ink composition, and thus the active energy ray-curable ink composition to which it is applied. has high fluidity and improves the glossiness of printed matter printed using it.
- active energy ray-curable ink compositions are described below.
- the active energy ray-curable ink composition mainly contains a compound having an ethylenically unsaturated bond and a coloring component as an optional component.
- a coloring component it is used for forming characters and images, and when the ink composition of the present invention does not contain a coloring component, it is used for coating purposes.
- the ink composition of the present invention contains the polyester resin of the present invention in addition to these components.
- Preferred examples of active energy rays used for curing include ultraviolet rays and electron beams. When ultraviolet light is used as the active energy ray, the wavelength may be appropriately determined according to the absorption wavelength of the photopolymerization initiator used, and may be 400 nm or less.
- ultraviolet irradiation devices that generate such ultraviolet rays include metal halide lamps, high-pressure mercury lamps, excimer lamps containing a rare gas, and ultraviolet light emitting diodes (LEDs).
- an irradiation device for irradiating the electron beam is not particularly limited. Examples of such irradiation devices include those of the Cockroft-Waltsin type, the Van de Graaff type, or the resonant transformer type.
- the energy of the electron beam is preferably 50-1000 eV, more preferably 100-300 eV. Regardless of which type of active energy ray is used, the irradiation dose is appropriately adjusted while observing the degree of curing of the ink composition.
- a photopolymerization initiator described later is added to the ink composition, and the photopolymerization initiator undergoes intramolecular cleavage upon irradiation with ultraviolet rays to generate radicals, thereby forming the ink composition.
- the photopolymerization initiator undergoes intramolecular cleavage upon irradiation with ultraviolet rays to generate radicals, thereby forming the ink composition.
- a compound with an ethylenically unsaturated bond is a component that is polymerized by radicals generated in the ink composition to increase the molecular weight, and is a component called a monomer or oligomer.
- various polymers having ethylenically unsaturated bonds are commercially available as polymers having a higher molecular weight than oligomers.
- Such polymers can also be crosslinked by the above-mentioned monomers or oligomers, or by the polymers themselves to have a high molecular weight. Therefore, such a polymer may be used as a compound having an ethylenically unsaturated bond together with the above monomers and oligomers.
- the monomer has an ethylenically unsaturated bond and is a component that is polymerized to have a high molecular weight as described above. It is also used as a solvent when dissolving to form a varnish, and is also used for the purpose of adjusting the viscosity of the ink composition.
- monomers include monofunctional monomers having one ethylenically unsaturated bond in the molecule and bifunctional or higher monomers having two or more ethylenically unsaturated bonds in the molecule.
- Bifunctional or higher functional monomers can crosslink molecules when the ink composition is cured, so they contribute to increasing the curing speed and forming a strong film.
- a monofunctional monomer does not have the cross-linking ability as described above, but contributes to reducing curing shrinkage due to cross-linking. These monomers can be used in combination as necessary.
- Monofunctional monomers include alkyl acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, dodecyl (meth) acrylate, (meth) acrylic acid, ethylene oxide adduct (meth)acrylate, propylene oxide adduct (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, tricyclodecane monomethylol (meth)acrylate, 2-hydroxyethyl (meth)acrylate Acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, hydroxypentyl (meth)acrylate, 2-hydroxy-3 - phenoxypropyl
- Bifunctional or higher monomers include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, pentyl glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, hydroxy pivalyl hydroxypivalate di(meth)acrylate, hydroxypivalyl hydroxypivalate dicaprolactonate di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,2-hexanediol di(meth)acrylate , 1,5-hexanediol di(meth)acrylate
- Bifunctional monomer glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane tricaprolactonate tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolhexane tri(meth)acrylate , trimethyloloctane tri(meth)acrylate, pentaerythritol tri(meth)acrylate; ) acrylates, diglycerin tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, ditrimethylolpropane tetracaprolactonate tetra(meth)acrylate, ditrimethylolethane tetra(meth)acrylate, ditrimethylolbutane tetra(meth)acrylate Acrylates, ditrimethylolhexane tetra(meth)acrylate, ditrimethyloloctane t
- TMPTA trimethylolpropane triacrylate
- DITMPTA ditrimethylolpropane tetraacrylate
- DPHA dipentaerythritol hexaacrylate
- GPTA glycerin propoxy triacrylate
- HDDA hexanediol diacrylate
- bifunctional or higher functional monomers can be used alone or in combination of two or more.
- epoxidized vegetable oil acrylate obtained by acrylic modification of epoxidized vegetable oil.
- This is a compound obtained by ring-opening addition polymerization of (meth)acrylic acid to the epoxy group of epoxidized vegetable oil obtained by epoxidizing the double bond of unsaturated vegetable oil with an oxidizing agent such as peracetic acid or perbenzoic acid.
- Unsaturated vegetable oils are triglycerides in which at least one fatty acid has at least one carbon-carbon unsaturated bond.
- Oligomers are components that polymerize to high molecular weight as described above, but since they are originally components with relatively high molecular weights, they are also used for the purpose of imparting appropriate viscosity and elasticity to the ink composition. Oligomers include epoxy-modified (meth)acrylates and rosin-modified epoxies, which are exemplified by esters of hydroxyl groups and (meth)acrylic acid generated after the epoxy groups contained in epoxy compounds such as epoxy resins are ring-opened with acids or bases.
- examples include polyether-modified (meth) acrylates, urethane-modified (meth) acrylates exemplified by esters of terminal hydroxyl groups and (meth) acrylic acid in condensates of polyisocyanate compounds and polyol compounds. .
- Such oligomers are commercially available and include, for example, the Ebecryl series from Daicel Cytec, CN, SR series from Sartomer, Aronix M-6000 series, 7000 series, 8000 series from Toagosei Co., Ltd. It is available under trade names such as Aronix M-1100, Aronix M-1200, Aronix M-1600, and NK Oligo manufactured by Shin-Nakamura Chemical Co., Ltd. These oligomers can be used alone or in combination of two or more.
- a polymer with an ethylenically unsaturated bond is a component that increases in molecular weight together with the above-mentioned monomers and oligomers, and since it has a large molecular weight before being irradiated with an active energy ray, it improves the viscoelasticity of the ink composition. It is a useful ingredient for Such polymers are used, for example, in a state of being dissolved or dispersed in a low-viscosity liquid monomer.
- Examples of polymers having ethylenically unsaturated bonds include polydiallyl phthalate, acrylic resins having unreacted unsaturated groups, and acrylic-modified phenolic resins. Among these, polydiallyl phthalate can be preferably used because of its particularly excellent compatibility with the above monomers and oligomers.
- the content of the compound having an ethylenically unsaturated bond in the ink composition is preferably 30-70% by mass, more preferably 40-60% by mass. When the content of the compound having an ethylenically unsaturated bond is within the above range, both good curability and good printability can be achieved. Moreover, the content of the polymer having an ethylenically unsaturated bond is preferably 0 to 50% by mass, more preferably 0 to 30% by mass, and even more preferably 0 to 20% by mass. When the content of the polymer is within the above range, it is possible to impart appropriate viscoelasticity to the ink composition, suppress the occurrence of misting and the like, and ensure good curability of the ink composition, which is preferable. .
- a photopolymerization initiator is a component that generates radicals upon irradiation with ultraviolet rays, and the radicals generated polymerize the compound having the ethylenically unsaturated bond to cure the ink composition.
- the photopolymerization initiator is not particularly limited as long as it generates radicals when irradiated with ultraviolet rays.
- the photopolymerization initiator is an essential component when ultraviolet light is used as the active energy ray for curing the ink composition, and an essential component when an electron beam is used as the active energy ray. It is an optional component.
- Photopolymerization initiators include benzophenone, diethylthioxanthone, 2-methyl-1-(4-methylthio)phenyl-2-morpholinopropan-1-one, 4-benzoyl-4'-methyldiphenylsulfide, 1-chloro- 4-propoxythioxanthone, isopropylthioxanthone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, bis-2,6-dimethoxybenzoyl-2,4,4-trimethylpentylphos Fin oxide, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2,2-dimethyl-2-hydroxyacetophenone, 2,2-dimethoxy -2-phenylacetophenone, 2,4,6-trimethylbenzyl-diphenylphosphine oxide, 2-benzyl-2-dimethylamino-1-(morpholinophenyl
- photopolymerization initiators are commercially available, for example, IGM Resins B.V. V. available from Lamberti under the trade names such as Omnirad 907, Omnirad 369, Omnirad 184, Omnirad 379, Omnirad 819, Omnirad TPO and the like from Lamberti under the trade names such as DETX. These photopolymerization initiators can be used alone or in combination of two or more.
- the content of the photopolymerization initiator in the ink composition is preferably 1 to 20% by mass, more preferably 2 to 15% by mass, and even more preferably 2 to 13% by mass.
- the content of the photopolymerization initiator in the ink composition is within the above range, it is possible to achieve both sufficient curability of the ink composition and good internal curability and cost, which is preferable.
- the ink composition of the present invention contains the epoxidized oil described later, the curability when irradiated with ultraviolet rays is improved, so it is possible to reduce the content of the photopolymerization initiator compared to conventional products. is. Therefore, it is preferable to appropriately reduce the amount of the photopolymerization initiator used while considering the actual printing conditions.
- a coloring component can be added to the ink composition of the present invention as necessary.
- the coloring component is a component added to impart coloring power, hiding power, etc. to the ink composition, and includes coloring pigments, white pigments, metal powders, and the like. Examples of such coloring components include organic and/or inorganic pigments conventionally used in ink compositions without particular limitation.
- the ink composition of the present invention does not contain a coloring component, it is preferably used for coating applications.
- Coloring components include disazo yellow (Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 1), yellow pigments such as Hansa Yellow, magenta pigments such as Brilliant Carmine 6B, Lake Red C, and Watching Red.
- yellow pigments such as Hansa Yellow
- magenta pigments such as Brilliant Carmine 6B, Lake Red C
- Watching Red examples include pigments, cyan pigments such as phthalocyanine blue, phthalocyanine green, and alkali blue, black pigments such as carbon black, white pigments such as titanium oxide, and metal powders such as aluminum paste and bronze powder.
- the content of the coloring component is exemplified by about 1 to 30% by mass with respect to the entire ink composition, but is not particularly limited.
- a coloring component of another color it is possible to use a coloring component of another color as a complementary color, or to add an ink composition of another color.
- the ink composition of the present invention contains the polyester resin of the present invention.
- this polyester resin When this polyester resin is added to the ink composition, it may be added to the ink composition as it is if it exhibits a liquid state, or if it is not, a low molecular weight resin such as ditrimethylolpropane triacrylate or ditrimethylolpropane tetraacrylate may be used.
- a varnish may be obtained by dissolving it in a viscous monomer.
- the amount of the polyester resin of the present invention added to the ink composition is preferably about 5 to 40% by mass, more preferably about 5 to 30% by mass, and even more preferably about 10 to 30% by mass. .
- ink composition of the present invention can be added to the ink composition of the present invention as necessary.
- examples of such components include extender pigments, resin components, polymerization inhibitors, dispersants, salts such as phosphates, waxes such as polyethylene waxes, olefin waxes and Fischer-Tropsch waxes, and alcohols.
- the extender pigment is a component for imparting properties such as appropriate printability and viscoelasticity to the ink composition, and various types commonly used in the preparation of the ink composition can be used.
- extender pigments include clay, kaolinite (kaolin), barium sulfate, magnesium sulfate, calcium carbonate, silicon oxide (silica), bentonite, talc, mica, and titanium oxide.
- the amount of such an extender pigment to be added is exemplified as about 0 to 33% by mass with respect to the entire ink composition, but is not particularly limited.
- the resin component is a component that contributes to imparting properties such as appropriate printability and viscoelasticity to the ink composition.
- a resin component include various resins that have been conventionally used for printing ink compositions, and those having compatibility with the above-mentioned monomers and oligomers are preferable.
- acrylic resins, acrylic resins, alkyd resins, rosin-modified phenolic resins, rosin-modified maleic acid resins, rosin-modified alkyd resins, rosin-modified petroleum resins, rosin ester resins, petroleum-modified phenolic resins, vegetable oil-modified alkyd resins, petroleum resins, etc. can be mentioned.
- the resin component When the resin component is added to the ink composition, its content in the ink composition is preferably 1 to 30% by mass, more preferably 1 to 20% by mass, and even more preferably 1 to 10% by mass. When the content of the resin component is within the above range, it is possible to impart appropriate viscoelasticity to the ink composition, suppress the occurrence of misting, etc., and ensure good curability of the ink composition. preferable.
- the polymerization inhibitor include phenolic compounds such as butylhydroxytoluene, tocopherol acetate, nitrosamines, benzotriazole, hindered amines, etc. Among them, butylhydroxytoluene is more preferable.
- phenolic compounds such as butylhydroxytoluene, tocopherol acetate, nitrosamines, benzotriazole, hindered amines, etc.
- butylhydroxytoluene is more preferable.
- the dispersant is used to disperse the coloring components and extender pigments contained in the ink composition in a favorable state.
- Various types of such dispersants are commercially available, and examples thereof include the DISPERBYK (trade name) series manufactured by BYK-Chemie Japan.
- the ink composition of the present invention can be produced using the above components.
- a method after mixing each of the above components, kneading with a bead mill, three-roll mill, etc. to disperse the pigment (that is, the coloring component and the extender pigment), and if necessary, the additive (polymerization inhibitor) agents, alcohols, waxes, etc.), and further adding the above-mentioned monomer component or oil component to adjust the viscosity.
- the viscosity of the ink composition for example, in the case of offset printing, a value of 10 to 70 Pa ⁇ s at 25° C. measured by a Laret viscometer can be exemplified, but is not particularly limited.
- the method for producing the active energy ray-curable ink composition of the present invention is also one aspect of the present invention.
- This production method is characterized by using the polyester resin produced by the above-described method for producing a polyester resin as one of the constituent components of the ink composition. Since these matters have already been described, descriptions thereof will be omitted here.
- Potatoes sliced to a thickness of 1 mm were added to 500 mL of commercially available edible oil and cooked at 180°C. By repeating this operation 5 to 100 times, samples of waste cooking oil with different peroxide values (POV) were prepared.
- two types of waste edible oil, OL1 and OL2 were obtained by changing the type of edible oil and the number of times of cooking.
- Salad oil manufactured by Nisshin OilliO Co., Ltd. was used for OL1
- soybean refined oil manufactured by the same company was used for OL2.
- waste cooking oil manufactured by Nisshin OilliO Co., Ltd., refined soybean oil used for cooking in the staff cafeteria of the Tokyo factory of Sakata Inx Co., Ltd.
- OL3 was collected and designated as OL3.
- OL4 is a waste cooking oil obtained from a waste oil recycling company (Yoshikawa Oil Co., Ltd.).
- OL5 is salad oil manufactured by Nisshin OilliO Co., Ltd.
- OL6 is soybean white squeezed oil manufactured by the same company. Table 1 shows the specifications of OL1 to OL6.
- Epoxidized OL1 to OL6 by a known method to obtain epoxidized oils and fats EPOL1 to EPOL6, respectively.
- the oil prepared using OL1 as the oil corresponds to epoxidized oil EPOL1, and similarly, those prepared using any of the oils OL2 to OL6 correspond to epoxidized oils EPOL2 to EPOL6, respectively.
- a commercially available epoxidized soybean oil was designated as EPOL7. Table 2 shows the specifications of EPOL1 to EPOL7.
- a polyester resin was prepared using any one of EPOL1 to EPOL7 as an epoxidized fat.
- EPOL 1 to 7 epoxidized oil
- disproportionated rosin manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., trade name "Dehydroabietin Acid", acid value 136 mg KOH / g) 375 parts by mass
- 1.5 parts by mass of triphenylphosphine, 25 parts by mass of 1,2-cyclohexenedicarboxylic acid, and 25 parts by mass of glycerin are added, and under a nitrogen atmosphere, at 200 ° C.
- Polyester resins R1 to R7 were prepared by reacting for 5 hours to carry out transesterification and polycondensation (dehydration condensation) reactions.
- the one prepared using EPOL1 as the epoxidized oil corresponds to the polyester resin R1
- the one prepared using any one of the epoxidized oils EPOL2 to EPOL7 corresponds to the polyester resins R2 to R7, respectively. handle.
- Table 3 shows the acid value and weight average molecular weight of the obtained polyester resins R1 to R7.
- a varnish was prepared using the polyester resin obtained above. 60 parts by mass of ditrimethylolpropane tetraacrylate and 0.15 parts by mass of butylhydroxytoluene (BHT) are added to 40 parts by mass of any of the polyester resins R1 to R7, and heated and stirred at 100 ° C. for 1 hour to obtain V1. A varnish of ⁇ V7 was prepared. Varnish V1 is prepared by using R1 as the polyester resin, and varnishes V2 to V7 are prepared by using any one of polyester resins R2 to R7.
- BHT butylhydroxytoluene
- ink compositions of Examples 1 to 5 and Comparative Examples 1 to 4 were prepared.
- each component shown in Tables 4 and 5 was mixed and then kneaded in a three-roll mill.
- each compounding amount is parts by mass
- "carbon black” is #60 manufactured by Mitsubishi Chemical Corporation
- "calcium carbonate” is Shiraishi Calcium Co., Ltd.
- the ink compositions of Examples 1 to 4 and Comparative Examples 1 to 3 are of the type that use ultraviolet rays as active energy rays and contain photopolymerization initiators (TPO and EAB).
- the ink composition is of a type that uses an electron beam as an active energy beam and does not contain a photopolymerization initiator.
- the ink compositions of Examples 1 to 4 according to the present invention are the inks of Comparative Examples 1 to 3 that do not contain a polyester resin derived from an epoxidized oil having a peroxide value of 1 meq/kg or more. Fluidity was higher than that of the composition, and the gloss of the cured film was also good. In addition, this tendency is the same even when an electron beam is used as the active energy beam. Compared to the ink composition of Comparative Example 4, which did not contain the ink composition, the fluidity was high, and the gloss of the cured film was also good. From these facts, the usefulness of the ink composition containing the polyester resin of the present invention can be understood.
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Abstract
Description
まずは、本発明のポリエステル樹脂の製造方法の一実施態様について説明する。本発明のポリエステル樹脂の製造方法は、エポキシ化油脂、多塩基酸及び多価アルコールを含む混合物を加熱することでエステル交換反応及び縮重合反応を生じさせてポリエステル樹脂を製造する方法であって、上記エポキシ化油脂の過酸化物価が1meq/kg以上であることを特徴とする。
次に、本発明のポリエステル樹脂の一実施形態について説明する。本発明のポリエステル樹脂は、上記製造方法により調製されるものであり、本発明の一つである。本発明のポリエステル樹脂は、エポキシ基を含む脂肪酸、及び多塩基酸を含む酸成分と、多価アルコールと、の縮重合体であり、上記脂肪酸をトリグリセリドに換算したときの過酸化物価が1meq/kg以上であることを特徴とする。なお、以下の説明を行うにあたり、既に説明したポリエステル樹脂の製造方法の説明と重複する部分についてはその説明を適宜省略する。
上記本発明のポリエステル樹脂を含むことを特徴とする活性エネルギー線硬化型インキ組成物も本発明の一つである。既に説明したように、本発明のポリエステル樹脂は、原材料としてバイオマス由来の成分比率が高く、これを含むインキ組成物のバイオマス由来の成分比率を高めることができる。そのため、このインキ組成物は、環境負荷が低減されており、IGマーク認証等、各種の環境関連の認証を受けるのに適した製品となる。また、これも既に説明したように、本発明のポリエステル樹脂は、揚げ物等に用いられた廃食用油等を由来とするエポキシ化油脂を用いて調製することも可能であり、この場合には、さらにインキ組成物の環境負荷を低減させることが可能である。
上記本発明の活性エネルギー線硬化型インキ組成物の製造方法もまた、本発明の一つである。この製造方法は、上記ポリエステル樹脂の製造方法で製造されたポリエステル樹脂をインキ組成物の構成成分の一つとして用いることを特徴とする。これらの事項については、既に述べた通りなので、ここでの説明を省略する。
各実施例及び比較例のインキ組成物のそれぞれについて、スプレッドメーターにてフロー値を測定し、フロー傾斜(スロープ)値として流動性を調べた。なお、フロー傾斜値とは、スプレッドメーターで100秒後の広がり直径をmm単位で計った数値から、10秒後の広がり直径をmm単位で計った数値を差し引いた数値であり、この値が大きいほど流動性が良好となる。算出されたフロー傾斜値の値を表4及び5の「流動性」欄に示した。
実施例1~4及び比較例1~3のインキ組成物のそれぞれについて、インキ組成物0.1ccを、RI展色機(2分割ロール、株式会社明製作所製)を用いて塗工紙(日本製紙株式会社製、オーロラコート)に展色した後に、メタルハライドランプを用い120W/cmの出力で展色物に40mJ/cm2の紫外線を照射して硬化させ、硬化直後の濃度をSpectroeye濃度計(Gretagmacbeth社製)により測定し、その濃度が1.50になるように調整した。次いで、村上式デジタル光沢計(村上色彩研究所製)を用いて展色面の60°反射光沢値を求めた。その結果を表4及び5の「光沢」欄に示した。また、実施例5及び比較例4のインキ組成物については、紫外線照射に代えて電子線照射装置(加速電圧90kV、照射光量30kGy)により電子線を照射することで硬化させたことを除いて実施例1~8及び比較例1~5のインキ組成物と同様の手順で光沢を評価し、その結果を表4及び5の「光沢」欄に示した。
Claims (10)
- エポキシ基を含む脂肪酸、及び多塩基酸を含む酸成分と、多価アルコールと、の縮重合体であり、前記脂肪酸をトリグリセリドに換算したときの過酸化物価が1meq/kg以上であることを特徴とするポリエステル樹脂。
- 前記酸成分としてさらに樹脂酸を含む請求項1記載のポリエステル樹脂。
- 請求項1又は2記載のポリエステル樹脂を含むことを特徴とする活性エネルギー線硬化型インキ組成物。
- エポキシ化油脂、多塩基酸及び多価アルコールを含む混合物を加熱することでエステル交換反応及び縮重合反応を生じさせてポリエステル樹脂を製造する方法であって、
前記エポキシ化油脂の過酸化物価が1meq/kg以上であることを特徴とするポリエステル樹脂の製造方法。 - 前記エポキシ化油脂の酸価が0.1mgKOH/g以上100mgKOH/g以下であることを特徴とする請求項4記載のポリエステル樹脂の製造方法。
- 前記エポキシ化油脂の過酸化物価が1meq/kg以上1000meq/kg以下であることを特徴とする請求項4又は5記載のポリエステル樹脂の製造方法。
- 前記エポキシ化油脂のオキシラン酸素濃度が0.5%以上50%以下であることを特徴とする請求項4~6のいずれか1項記載のポリエステル樹脂の製造方法。
- 前記混合物が、さらに樹脂酸を含むことを特徴とする請求項4~7のいずれか1項記載のポリエステル樹脂の製造方法。
- 前記エポキシ化油脂が、廃食用油のエポキシ変性体である請求項4~8のいずれか1項記載のポリエステル樹脂の製造方法。
- 請求項4~9のいずれか1項記載の方法で製造されたポリエステル樹脂を構成成分の一つとして用いることを特徴とする活性エネルギー線硬化型インキ組成物の製造方法。
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59105065A (ja) * | 1982-11-25 | 1984-06-18 | ベ−・ア−・エス・エフ・フアルベン・ウント・フア−ゼルン・アクチエンゲゼルシヤフト | 印刷インキ、その製法及び脱墨可能な紙印刷物を得る方法 |
JP2009024058A (ja) * | 2007-07-18 | 2009-02-05 | Biobase Kk | ポリ乳酸樹脂組成物およびポリ乳酸樹脂用添加剤 |
JP2014173070A (ja) * | 2013-03-12 | 2014-09-22 | Sakata Corp | 活性エネルギー線硬化型オフセット印刷インキ組成物 |
US20150087732A1 (en) * | 2013-09-20 | 2015-03-26 | The United States Of America, As Represented By The Secretary Of Agriculture | Elastomer Derived From Epoxidized Vegetable Oil |
JP2018065912A (ja) * | 2016-10-18 | 2018-04-26 | サカタインクス株式会社 | ロジン変性アルキッド樹脂及びその製造方法、並びにそれを用いたオフセット印刷用インキ組成物及びそれを用いた印刷物の製造方法 |
JP2018115223A (ja) * | 2017-01-16 | 2018-07-26 | サカタインクス株式会社 | 活性エネルギー線硬化型オフセット印刷用インキ組成物、及びそれを用いた印刷物の製造方法 |
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JP4961691B2 (ja) * | 2005-07-25 | 2012-06-27 | 株式会社明電舎 | 絶縁性高分子材料硬化物 |
US20150111141A1 (en) * | 2013-10-22 | 2015-04-23 | Xerox Corporation | Bio-Based Toner Resin with Increased Fusing Performance |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59105065A (ja) * | 1982-11-25 | 1984-06-18 | ベ−・ア−・エス・エフ・フアルベン・ウント・フア−ゼルン・アクチエンゲゼルシヤフト | 印刷インキ、その製法及び脱墨可能な紙印刷物を得る方法 |
JP2009024058A (ja) * | 2007-07-18 | 2009-02-05 | Biobase Kk | ポリ乳酸樹脂組成物およびポリ乳酸樹脂用添加剤 |
JP2014173070A (ja) * | 2013-03-12 | 2014-09-22 | Sakata Corp | 活性エネルギー線硬化型オフセット印刷インキ組成物 |
US20150087732A1 (en) * | 2013-09-20 | 2015-03-26 | The United States Of America, As Represented By The Secretary Of Agriculture | Elastomer Derived From Epoxidized Vegetable Oil |
JP2018065912A (ja) * | 2016-10-18 | 2018-04-26 | サカタインクス株式会社 | ロジン変性アルキッド樹脂及びその製造方法、並びにそれを用いたオフセット印刷用インキ組成物及びそれを用いた印刷物の製造方法 |
JP2018115223A (ja) * | 2017-01-16 | 2018-07-26 | サカタインクス株式会社 | 活性エネルギー線硬化型オフセット印刷用インキ組成物、及びそれを用いた印刷物の製造方法 |
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