WO2010098240A1 - ロジン変性フェノール樹脂、その製造方法および印刷インキ - Google Patents
ロジン変性フェノール樹脂、その製造方法および印刷インキ Download PDFInfo
- Publication number
- WO2010098240A1 WO2010098240A1 PCT/JP2010/052367 JP2010052367W WO2010098240A1 WO 2010098240 A1 WO2010098240 A1 WO 2010098240A1 JP 2010052367 W JP2010052367 W JP 2010052367W WO 2010098240 A1 WO2010098240 A1 WO 2010098240A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rosin
- acid
- parts
- component
- weight
- Prior art date
Links
- 238000007639 printing Methods 0.000 title claims abstract description 30
- 150000002989 phenols Chemical class 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 33
- 239000005011 phenolic resin Substances 0.000 title abstract description 23
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 6
- 229920005862 polyol Polymers 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 79
- 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 61
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 59
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 59
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 abstract description 8
- 239000003595 mist Substances 0.000 abstract description 8
- 230000001804 emulsifying effect Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- HPQKNJHVWUWAOR-QEQIUYPFSA-N (1r,4ar,5s,8ar)-5-(4-carboxy-3-methylbutyl)-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2h-naphthalene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@@H](CCC(C)CC(O)=O)C(=C)CC1 HPQKNJHVWUWAOR-QEQIUYPFSA-N 0.000 abstract 1
- HPQKNJHVWUWAOR-UHFFFAOYSA-N Oliveric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C(CCC(C)CC(O)=O)C(=C)CC2 HPQKNJHVWUWAOR-UHFFFAOYSA-N 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000003292 diminished effect Effects 0.000 abstract 1
- 239000002932 luster Substances 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 31
- 238000003756 stirring Methods 0.000 description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000000944 linseed oil Substances 0.000 description 17
- 235000021388 linseed oil Nutrition 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- 241001528275 Eucalyptus deglupta Species 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000002966 varnish Substances 0.000 description 12
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- -1 ditrimethylolethane Chemical compound 0.000 description 6
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 6
- 239000000347 magnesium hydroxide Substances 0.000 description 6
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 description 6
- 239000008158 vegetable oil Substances 0.000 description 6
- 229920003987 resole Polymers 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 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 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 229940105990 diglycerin Drugs 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 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
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 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
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 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
- 229930003836 cresol Natural products 0.000 description 1
- VAROLYSFQDGFMV-UHFFFAOYSA-K di(octanoyloxy)alumanyl octanoate Chemical compound [Al+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VAROLYSFQDGFMV-UHFFFAOYSA-K 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000011134 resol-type phenolic resin Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- 235000013904 zinc acetate Nutrition 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
- C09D11/103—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds of aldehydes, e.g. phenol-formaldehyde resins
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/34—Chemically modified polycondensates by natural resins or resin acids, e.g. rosin
-
- 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
- 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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C09D161/14—Modified phenol-aldehyde condensates
Definitions
- the present invention relates to a rosin-modified phenolic resin, a production method thereof, and a printing ink.
- Patent Document 1 As means for solving such a problem, it has been proposed to use a petroleum resin composition for printing ink, but it has been difficult to satisfy a wide variety of ink performances by using a petroleum resin alone (see Patent Document 1). . It has also been proposed to use a rosin-modified phenol resin having a weight average molecular weight of 3 to 250,000 using a C10-20 alkylphenol and an acid catalyst as a resin for printing ink. It was difficult and lacked versatility (see Patent Document 2). The present applicant also reduced the amount of mist and improved gloss by reducing low molecular weight components contained in the rosin-modified phenolic resin. However, further improvement has been demanded (see Patent Document 3).
- the present invention provides a rosin-modified phenolic resin capable of reducing the amount of mist of printing ink without deteriorating the gloss of printed matter while maintaining various ink performances (drying properties, emulsifying properties, etc.), its production method and the above-mentioned
- An object is to provide a printing ink containing a rosin-modified phenolic resin.
- the present inventors paid attention to the resin acid component contained in rosins that are components of rosin-modified phenolic resins, and as a result, studied the specific amount of dihydroagatinic acid contained in rosins. As a result, the present inventors have found that the above problems can be solved, and have completed the present invention.
- the present invention is obtained by reacting rosins (a) containing 0.4 to 10% of dihydroagatinic acid, a condensate (b) of phenols and formaldehyde, and a polyol (c).
- a rosin-modified phenolic resin characterized by reacting rosins (a) containing 0.4 to 10% dihydroagatic acid, a condensate (b) of phenols and formaldehyde, and a polyol (c)
- a process for producing a rosin-modified phenolic resin relates to a printing ink comprising the rosin-modified phenolic resin.
- the printing ink resin according to the present invention is used as an offset printing ink resin for offset sheet-fed ink (sheet-fed ink), offset rotary ink (off-wheel ink), newspaper ink, etc. It is also suitably used as a resin for letterpress printing ink and gravure printing ink.
- the rosin-modified phenolic resin of the present invention includes rosins (hereinafter referred to as component (a)) containing 0.4 to 10% of dihydroagatinic acid, and condensates of phenols and formaldehyde (hereinafter referred to as component (b)). ) And polyols (hereinafter referred to as component (c)) as essential components.
- component (a) rosins
- component (b) condensates of phenols and formaldehyde
- component (c) polyols
- the component (a) used in the present invention is not particularly limited as long as it is a rosin containing 0.4 to 10% of dihydroagatic acid, and a known one can be used. If the content of dihydroagatinic acid exceeds 10%, the rosin-modified phenolic resin may have a high molecular weight and insoluble matter may be generated. If it is less than 0.4%, misting tends to occur.
- the amount of dihydroagatinic acid is preferably 3 to 10%, more preferably 3 to 9%.
- content of dihydroagatinic acid can be calculated
- Dihydroagatic acid is a dicarboxylic acid form, and is usually contained in many Indonesian gum rosins and Vietnamese gum rosins. Therefore, when using these gum rosins, they can be used as they are. However, since most Chinese gum rosins do not contain dihydroagatin acid, when using gum rosin with a low dihydroagatin acid content, for example, the method described in JP-A-51-131899 is used. It is necessary to adjust the amount of dihydroagatinic acid by adding dihydroagatinic acid isolated in this manner.
- component (a) for example, natural rosin such as gum rosin, tall oil rosin, wood rosin; polymerized rosin derived from the natural rosin; stabilized rosin obtained by disproportionating or hydrogenating natural rosin or polymerized rosin
- a dihydroagatin acid added to an unsaturated acid-modified rosin obtained by adding an unsaturated carboxylic acid to a natural rosin or a polymerized rosin may be used within the above range, a polymerized rosin, a stabilized rosin,
- As raw materials for various rosin derivatives such as unsaturated acid-modified rosin, rosin containing dihydroagatinic acid within the above-mentioned range may be used.
- the unsaturated acid-modified rosins include, for example, maleic acid-modified rosin, maleic anhydride-modified rosin, fumaric acid-modified rosin, acrylic acid-modified rosin, methacrylic acid-modified rosin, and acid-modified polymerization rosin corresponding thereto. can give.
- the unsaturated acid-modified rosins are modified with usually 1 to 30 parts by weight of an unsaturated carboxylic acid per 100 parts by weight of the raw material rosin.
- These components (a) can be used alone or in combination. When used in combination, the total amount of dihydroagatinic acid in all components (a) may be within the range of use specified in the present invention.
- Component (b) includes phenols (P) and formaldehyde (F) such as sodium hydroxide, potassium hydroxide, calcium hydroxide and the like within a range where the F / P (molar ratio) is usually about 1 to 3.
- F / P (molar ratio) of a condensate (resol type phenolic resin) subjected to addition / condensation reaction in the presence of an alkali catalyst or phenols (P) and formaldehyde (F) is usually about 0.5 to 2.
- a condensate (novolak type phenol resin) subjected to addition / condensation reaction in the presence of an acid catalyst such as succinic acid, sulfuric acid, hydrochloric acid, paratoluenesulfonic acid, and the like, and various known ones are used without particular limitation. be able to.
- the condensate may be neutralized and washed with water as component (b).
- phenols include carboxylic acid, cresol, amylphenol, bisphenol A, butylphenol, octylphenol, nonylphenol, and dodecylphenol.
- formaldehyde, formalin, paraformaldehyde or the like may be used.
- the component (b) it is preferable to use a resol type phenol resin from the viewpoint of increasing the molecular weight of the rosin-modified phenol resin.
- Component (c) is not particularly limited as long as it is a compound having at least two hydroxyl groups in one molecule, and known components can be used. Specific examples include dipentaerythritol, pentaerythritol, diglycerin, glycerin, ditrimethylolpropane, trimethylolpropane, ditrimethylolethane, triethylene glycol, diethylene glycol, ethylene glycol, neopentyl glycol and the like. Among the components (c), since the softening point, molecular weight, etc.
- the longest carbon chain of the molecule such as glycerin, trimethylolpurpan, trimethylolethane, etc.
- the amount of component (a), component (b), and component (c) used in the rosin-modified phenolic resin of the present invention is not particularly limited and may be appropriately determined depending on the application, but is usually component (a).
- the amount of component (a) used is about 41 to 88% by weight, preferably about 46 to 74% by weight, based on the total amount of component (b) and component (c) used of 100% by weight.
- the amount of use of b) (solid content) is about 9 to 50% by weight, preferably about 22 to 46% by weight, and the amount of component (c) used is about 3 to 9% by weight, preferably 4 to 8% by weight. %.
- reaction conditions such as catalyst and reaction temperature are not particularly limited.
- component (a), component (b) and component (c) are charged into a reactor in predetermined amounts, and if necessary, in the presence of various known acidic or basic catalysts, in a temperature range of about 100 to 300 ° C. For about 1 to 24 hours.
- the catalyst examples include mineral acids such as hydrochloric acid and sulfuric acid, sulfonic acids such as methanesulfonic acid, paratoluenesulfonic acid and dodecylbenzenesulfonic acid, metal oxides such as zinc oxide, magnesium oxide and calcium oxide, magnesium hydroxide, water Examples thereof include metal hydroxides such as calcium oxide and acetates such as calcium acetate, magnesium acetate and zinc acetate.
- a method of reacting by adding component (c) to the obtained reaction product reacting component (a) and component (c) After that, it can also be produced by a method in which the component (b) is added to the reaction product obtained to cause the reaction.
- the rosin-modified phenolic resin of the present invention obtained by the above method is characterized by having a high molecular weight and a high softening point.
- the weight average molecular weight (polystyrene conversion value by gel permeation chromatography) of the rosin-modified phenolic resin of the present invention is in the range of about 3,000 to 400,000.
- the weight average molecular weight is preferably 50,000 or more, more preferably 80,000 or more, and further preferably 100,000 or more. When the weight average molecular weight is smaller than 3,000, the amount of ink mist tends to increase.
- the weight average molecular weight is preferably 400,000 or less, and more preferably 300,000 or less.
- the weight average molecular weight is preferably 50,000 to 400,000, more preferably 50,000 to 300,000, further preferably 80,000 to 300,000, and more preferably 100,000.
- the softening point is preferably about 140 to 200 ° C. By setting the softening point to 140 ° C. or higher, the drying property of the printed matter can be appropriately maintained, and by setting the softening point to 200 ° C. or lower, the affinity with the ink varnish can be increased and sufficient solubility can be maintained.
- the rosin-modified phenolic resin thus obtained can be mixed with vegetable oils and, if necessary, petroleum-based solvent for ink and mixed to produce a varnish for printing ink.
- the vegetable oil conventionally known vegetable oils can be used without particular limitation. Specifically, for example, linseed oil, tung oil, safflower oil, dehydrated castor oil, soybean oil and other vegetable oils, linseed oil fatty acid methyl, soybean oil fatty acid methyl, linseed oil fatty acid ethyl, soybean oil fatty acid ethyl, linseed oil Examples thereof include monoesters of the above vegetable oils such as fatty acid propyl, soybean oil fatty acid propyl, linseed oil fatty acid butyl, soybean oil fatty acid butyl and the like. These may be used alone or in combination of two or more. In these, the vegetable oil which has an unsaturated bond in a molecule
- the ink petroleum solvent a conventionally known ink petroleum solvent can be used without any particular limitation.
- No. 0 solvent, No. 4, Solvent No. 5, No. 5, Solvent No. 6, Solvent No. 7, AF Solvent No. 4, AF Solvent No. 5, which are petroleum solvents manufactured by Nippon Oil Corporation examples include AF solvent 6 and AF solvent 7. These may be used alone or in combination of two or more.
- the varnish for printing ink can be produced by mixing and stirring the above-mentioned components. In mixing and stirring, these components are heated to about 100 to 240 ° C., preferably about 100 to 200 ° C. Is dissolved and mixed, and if necessary, obtained using additives.
- the additive include an antioxidant and the like in addition to a gelling agent for imparting elasticity.
- gelling agent examples include various known materials such as aluminum octylate, aluminum stearate, aluminum triisopropoxide, aluminum tributoxide, aluminum dipropoxide monoacetyl acetate, aluminum dibutoxide monoacetyl acetate, and aluminum triacetyl acetate. Can be used without any particular limitation.
- the printing ink of the present invention contains pigments (yellow, red, indigo, black), the varnish for printing ink, and uses various known additives as necessary, such as a roll mill, a ball mill, an attritor, and a sand mill. It can be obtained by kneading and preparing so as to obtain an appropriate ink constant using a known ink production apparatus.
- the additive include a surfactant for improving ink fluidity and an ink surface film, and wax.
- part means parts by weight.
- the content of dihydroagatinic acid was determined using gas chromatography (manufactured by Shimadzu Corporation, GC-14A).
- Example 1 (Production example A of rosin-modified phenolic resin)
- a reaction vessel equipped with a stirrer, a reflux condenser with a water separator and a thermometer was charged with 1,000 parts of Indonesian gum rosin (containing 8% of dihydroagatinic acid as component (a)), and this was placed in a nitrogen atmosphere.
- the mixture was heated to 180 ° C. with stirring and melted.
- 93 parts of pentaerythritol and 3 parts of magnesium hydroxide were added, the temperature was raised to 280 ° C. with stirring, and the reaction was continued until the acid value was 25 mgKOH / g or less.
- the 33% by weight linseed oil viscosity is measured at 25 ° C. using a cone and plate viscometer manufactured by Nippon Rheology Co., Ltd., with a mixture of resin and linseed oil heated in a 1 to 2 weight ratio. (Hereinafter the same).
- the acid value and softening point were measured according to JIS K5601 (hereinafter the same).
- the weight average molecular weight is based on polystyrene measured using a gel permeation chromatography (manufactured by Tosoh Corporation, HLC-8120GPC) and a TSK-GEL column made by Tosoh Corporation (hereinafter referred to as THF solvent) The same).
- Example 2 (Production Example B of rosin-modified phenol resin)
- 500 parts of Indonesian gum rosin (containing 8% dihydroagatic acid) and 500 parts of Chinese gum rosin (containing 0% dihydroagatinic acid) component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- pentaerythritol and 3 parts of magnesium hydroxide were added, the temperature was raised to 280 ° C. with stirring, and the reaction was continued until the acid value was 25 mgKOH / g or less.
- Example 3 (Production Example C of rosin-modified phenolic resin)
- 70 parts of Indonesian gum rosin (containing 7.1% dihydroagatin acid) and 930 parts of Chinese gum rosin (containing 0% dihydroagatinic acid) were charged ( The rosin mixture as component (a) contains 0.5% of dihydroagatic acid.)
- the rosin mixture as component (a) contains 0.5% of dihydroagatic acid.
- 93 parts of pentaerythritol and 3 parts of magnesium hydroxide were added, the temperature was raised to 280 ° C. with stirring, and the reaction was continued until the acid value was 25 mgKOH / g or less.
- Example 4 (Production Example D of rosin-modified phenolic resin)
- 970 parts of Chinese gum rosin (containing 0% dihydroagatic acid) and 30 parts of dihydroagatinic acid were charged (into the rosin mixture component (a), dihydroaga Containing 3% of tinic acid), this was heated to 180 ° C. with stirring in a nitrogen atmosphere and melted.
- 93 parts of pentaerythritol and 3 parts of magnesium hydroxide were added, the temperature was raised to 280 ° C. with stirring, and the reaction was continued until the acid value was 25 mgKOH / g or less.
- Example 5 (Production Example E of rosin-modified phenolic resin)
- 969 parts of Indonesian gum rosin containing 7.1% of dihydroagatinic acid
- 31 parts of dihydroagatinic acid into the rosin mixture as component (a)
- 10% of dihydroagatinic acid was contained.
- the mixture was heated to 180 ° C. with stirring in a nitrogen atmosphere and melted.
- 93 parts of pentaerythritol and 3 parts of magnesium hydroxide were added, the temperature was raised to 280 ° C. with stirring, and the reaction was continued until the acid value was 25 mgKOH / g or less.
- Example 6 (Production Example F of rosin-modified phenolic resin)
- 500 parts of Indonesian gum rosin (containing 8% dihydroagatic acid) and 500 parts of Chinese gum rosin (containing 0% dihydroagatinic acid) component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- 84 parts of glycerin and 8 parts of zinc oxide were added, the temperature was raised to 270 ° C. with stirring, and the reaction was continued until the acid value became 25 mgKOH / g or less.
- Example 7 (Production example G of rosin-modified phenolic resin)
- 500 parts of Indonesian gum rosin (containing 8% dihydroagatic acid) and 500 parts of Chinese gum rosin (containing 0% dihydroagatinic acid) component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- 84 parts of glycerin and 7 parts of zinc oxide were added, the temperature was raised to 270 ° C. with stirring, and the reaction was continued until the acid value became 25 mgKOH / g or less.
- Example 8 (Production example H of rosin-modified phenolic resin)
- 500 parts of Indonesian gum rosin (containing 8% dihydroagatic acid) and 500 parts of Chinese gum rosin (containing 0% dihydroagatinic acid) component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- pentaerythritol was added, the temperature was raised to 250 ° C. with stirring, and the temperature was kept for 1 hour.
- Example 9 (Production example I of rosin-modified phenolic resin)
- 500 parts of Indonesian gum rosin (containing 8% dihydroagatic acid) and 500 parts of Chinese gum rosin (containing 0% dihydroagatinic acid) component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- component ( The rosin mixture which is a) contains 4% of dihydroagatinic acid)
- pentaerythritol was added, the temperature was raised to 250 ° C. with stirring, and the temperature was kept for 1 hour.
- Example 1 is the same as Example 1 except that Indonesian gum rosin is changed to Chinese gum rosin that does not contain dihydroagatinic acid (containing 0% of dihydroagatinic acid in component (a)).
- a rosin-modified phenolic resin was prepared.
- the viscosity of the obtained rosin-modified phenol resin was 6 Pa ⁇ s, and did not reach the target viscosity.
- the acid value was 19.5 mgKOH / g, the softening point was 168 ° C., and the weight average molecular weight was 48,000.
- Example 3 Comparative Example 2 In Example 3, the rosin mixture was changed to 40 parts of Indonesian gum rosin (containing 8% dihydroagatic acid) and 960 parts of Chinese gum rosin (containing 0% dihydroagatinic acid).
- a rosin-modified phenolic resin was prepared in the same manner as in Example 1 except that the rosin mixture as component (a) contained 0.3% of dihydroagatinic acid.
- the acid value of the obtained rosin-modified phenol resin was 20.0 mgKOH / g, the softening point was 175 ° C., and the weight average molecular weight was 79,000.
- Example 3 In Example 1, the amount of Indonesian gum rosin (containing 8% dihydroagatinic acid) was changed to 960 parts, and 40 parts of dihydroagatinic acid was further added (rosin mixture as component (a)) A rosin-modified phenolic resin was prepared in the same manner as in Example 1 except that 12% of dihydroagatinic acid was contained therein. Insoluble matter was generated in the obtained rosin-modified phenol resin.
- Comparative Example 4 In Comparative Example 1, a rosin-modified phenolic resin was prepared in the same manner as in Example 1 except that 20 parts of maleic anhydride was further added (component (a) contained 0% dihydroagatinic acid). .
- the acid value of the obtained rosin-modified phenol resin was 22.1 mgKOH / g, the softening point was 177 ° C., and the weight average molecular weight was 104,000.
- Table 1 shows the resin physical properties obtained in the examples and comparative examples.
- printing ink was prepared by kneading with a three roll mill at the following blending ratio. 18 parts by weight of phthalocyanine blue (indigo pigment) 62 to 70 parts by weight of the gel varnish 12 to 20 parts by weight of Nisseki AF Solvent 7 12 to 20 parts by weight Based on the above formulation, the tack value of the incometer is 6.5 ⁇ 0.5 at 400 ° C. The flow value (diameter value) of the spread meter at 25 ° C. was appropriately adjusted to be 38.0 ⁇ 1.0.
- Emsification rate 3.9 ml of ink was developed on a dynamic emulsification tester (manufactured by Nippon Rheology Equipment Co., Ltd.), and pure water was supplied at a roll temperature of 30 ° C. and 200 rpm at a rate of 5 ml / min. It measured with the infrared moisture meter.
- the printing inks (Examples 1 to 9) using the rosin-modified phenolic resin of the present invention have the designated range by setting the content of dihydroagatinic acid within the range of use designated in the present invention. It turns out that it has the outstanding misting resistance, without impairing gloss compared with external printing ink (Comparative Examples 1 and 2).
- the printing ink (Comparative Example 4) using a rosin-modified phenolic resin obtained by reacting a dibasic acid without using dihydroagatinic acid and having a high molecular weight has excellent misting resistance but poor gloss. It was.
- the printing ink has excellent misting resistance as compared with the printing ink (Example 6) below the range, and above the range. Compared with (Example 9), the handling property at the time of manufacturing the gel varnish is better.
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Abstract
Description
(アルキルフェノール-ホルムアルデヒド縮合物の製造)
攪拌機、分水器付き還流冷却管および温度計を備えた反応容器に、オクチルフェノール1,000部、92%パラホルムアルデヒド317部、キシレン564部および水500部を仕込み、攪拌下に50℃まで昇温した。次いで、同反応容器に45%水酸化ナトリウム溶液89部を仕込み、冷却しながら反応系を90℃まで徐々に昇温した後、2時間保温し、更に硫酸を滴下してpHを6付近に調整した。その後、ホルムアルデヒドなどを含んだ水層部を除去し、再度水洗した後に内容物を冷却して、レゾール型オクチルフェノールの70重量%キシレン溶液を得た。
(アルキルフェノール-ホルムアルデヒド縮合物の製造)
攪拌機、分水器付き還流冷却管および温度計を備えた反応容器に、オクチルフェノール800部、ブチルフェノール200部、92%パラホルムアルデヒド340部、キシレン573部および水500部を仕込み、攪拌下に50℃まで昇温した。次いで、同反応容器に45%水酸化ナトリウム溶液89部を仕込み、冷却しながら反応系を90℃まで徐々に昇温した後、2時間保温し、更に硫酸を滴下してpHを6付近に調整した。その後、ホルムアルデヒドなどを含んだ水層部を除去し、再度水洗した後に内容物を冷却して、レゾール型オクチル/ブチルフェノールの70重量%キシレン溶液を得た。
(ロジン変性フェノール樹脂の製造例A)
攪拌機、分水器付き還流冷却管および温度計を備えた反応容器に、インドネシア産ガムロジン(成分(a)としてジヒドロアガチン酸を8%含有する。)1,000部を仕込み、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール93部および水酸化マグネシウム3部を添加し、攪拌下に280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は22.6mgKOH/g、軟化点は176℃、重量平均分子量は107,000であった。なお、33重量%アマニ油粘度とは、樹脂とアマニ油を1対2重量比で加熱混合したものを、日本レオロジー(株)製のコーン・アンド・プレート型粘度計を用いて25℃で測定した粘度をいう(以下、同様)。また、酸価と軟化点はJIS K5601に準じて測定したものである(以下、同様)。また、重量平均分子量はゲルパーメーションクロマトグラフィー(東ソー(株)製、HLC-8120GPC)および東ソー(株)製TSK-GELカラムを用い、THF溶媒下で測定したポリスチレン換算によるものをいう(以下、同様)。
(ロジン変性フェノール樹脂の製造例B)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)500部および中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)500部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を4%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール93部および水酸化マグネシウム3部を添加し、攪拌下に280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は20.2mgKOH/g、軟化点は176℃、重量平均分子量は95,000であった。
(ロジン変性フェノール樹脂の製造例C)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を7.1%含有する。)70部および中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)930部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を0.5%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール93部および水酸化マグネシウム3部を添加し、攪拌下に280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は19.8mgKOH/g、軟化点は175℃、重量平均分子量は87,000であった。
(ロジン変性フェノール樹脂の製造例D)
実施例1と同様の反応容器に、中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)970部およびジヒドロアガチン酸30部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を3%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール93部および水酸化マグネシウム3部を添加し、攪拌下に280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は20.8mgKOH/g、軟化点は177℃、重量平均分子量は101,000であった。
(ロジン変性フェノール樹脂の製造例E)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を7.1%含有する。)969部およびジヒドロアガチン酸31部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を10%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール93部および水酸化マグネシウム3部を添加し、攪拌下に280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は23.3mgKOH/g、軟化点は178℃、重量平均分子量は139,000であった。
(ロジン変性フェノール樹脂の製造例F)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)500部および中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)500部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を4%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、グリセリン84部および酸化亜鉛8部を添加し、攪拌下に270℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例2のレゾール型オクチル/ブチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は21.8mgKOH/g、軟化点は181℃、重量平均分子量は47,000であった。
(ロジン変性フェノール樹脂の製造例G)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)500部および中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)500部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を4%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、グリセリン84部および酸化亜鉛7部を添加し、攪拌下に270℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例2のレゾール型オクチル/ブチルフェノールの70重量%キシレン溶液714部(固形分500部)を230~260℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は21.5mgKOH/g、軟化点は181℃、重量平均分子量は51,000であった。
(ロジン変性フェノール樹脂の製造例H)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)500部および中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)500部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を4%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール103部を添加し、攪拌下に250℃まで昇温し、1時間保温した。保温後、トリフェニルホスファイト2部を仕込み、280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を240~270℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は19.4mgKOH/g、軟化点は178℃、重量平均分子量は299,000であった。
(ロジン変性フェノール樹脂の製造例I)
実施例1と同様の反応容器に、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)500部および中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)500部を仕込み(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を4%含有する。)、これを窒素雰囲気下に攪拌しながら180℃まで昇温して溶融した。次いで、ペンタエリスリトール103部を添加し、攪拌下に250℃まで昇温し、1時間保温した。保温後、トリフェニルホスファイト3部を仕込み、280℃まで昇温し、酸価が25mgKOH/g以下となるまで反応した。更に230℃まで冷却した後、製造例1のレゾール型オクチルフェノールの70重量%キシレン溶液714部(固形分500部)を240~270℃の温度範囲内で9時間かけて系内へ滴下した。滴下終了後、33重量%アマニ油粘度が10Pa・sとなるよう調整し、0.02MPaで10分間減圧して内容物を取り出した。こうして得られたロジン変性フェノール樹脂の酸価は17.1mgKOH/g、軟化点は178℃、重量平均分子量は305,000であった。
実施例1において、インドネシア産ガムロジンを、ジヒドロアガチン酸を含有しない中国産ガムロジン(成分(a)中にジヒドロアガチン酸を0%含有する。)に変更したこと以外は実施例1と同様にしてロジン変性フェノール樹脂を調製した。得られたロジン変性フェノール樹脂の粘度は6Pa・sであり、目標の粘度に達しなかった。酸価は19.5mgKOH/g、軟化点は168℃、重量平均分子量は48,000であった。
実施例3において、ロジン混合物を、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)を40部、中国産ガムロジン(ジヒドロアガチン酸を0%含有する。)を960部に変更したこと(成分(a)である前記ロジン混合物中にジヒドロアガチン酸を0.3%含有する。)以外は実施例1と同様にしてロジン変性フェノール樹脂を調製した。得られたロジン変性フェノール樹脂の酸価は20.0mgKOH/g、軟化点は175℃、重量平均分子量は79,000であった。
実施例1において、インドネシア産ガムロジン(ジヒドロアガチン酸を8%含有する。)の使用量を960部に変更し、更にジヒドロアガチン酸を40部添加したこと(成分(a)であるロジン混合物中にジヒドロアガチン酸を12%含有する。)以外は実施例1と同様にしてロジン変性フェノール樹脂を調製した。得られたロジン変性フェノール樹脂中に不溶物が発生していた。
比較例1において、さらに、無水マレイン酸を20部添加したこと(成分(a)中にジヒドロアガチン酸を0%含有する。)以外は実施例1と同様にしてロジン変性フェノール樹脂を調製した。得られたロジン変性フェノール樹脂の酸価は22.1mgKOH/g、軟化点は177℃、重量平均分子量は104,000であった。
各実施例および比較例で得られた樹脂を45.0部、アマニ油10.0部、及びAFソルベント7号(新日本石油(株)製、非芳香族石油系溶剤)44.3部を200℃で30分間混合溶解した。次に、これを80℃まで冷却した後、アルミニウムジプロポキシドモノアセチルアセテート(商品名ケロープEP-2、ホープ製薬(株)製)0.7部を加え、200℃まで加熱して1時間ゲル化反応させ、ゲルワニスを得た。なお、実施例9の樹脂を用いたゲルワニスは弾性が強く、反応容器からの取り出しが困難であった。
前記実施例および比較例のゲルワニスを用い、次の配合割合で3本ロールミルにより練肉して印刷インキを調製した。
フタロシアニンブルー(藍顔料)18重量部
前記ゲルワニス 62~70重量部
日石AFソルベント7号 12~20重量部
上記配合に基づいて30℃、400rpmにおけるインコメーターのタック値が6.5±0.5、25℃におけるスプレッドメーターのフロー値(直径値)が38.0±1.0となるよう適宜調製した。
前記ゲルワニスを用いて調製した印刷インキの性能を下記試験により評価した。結果を表2に示す。
(光沢)
インキ0.4mlをRIテスター(石川島産業機械(株)製)にてアート紙に展色した後、23℃、50%R.H.にて24時間調湿し、60゜-60゜の反射率を光沢計により測定した。
(ミスチング)
インキ2.6mlをインコメーター(東洋精機(株)製)上に展開し、ロール温度30℃、400rpmで1分間、更に1800rpmで2分間回転させ、ロール直下に置いた白色紙上へのインキの飛散度を観察して1~5段階で評価を行なった。ミスチングは数値が大きいほどミスト量が少なく、良好であることを示す。
(乾燥性)
インキ0.4mlをRIテスター(石川島産業機械(株)製)にてアート紙に展色した後、160℃の雰囲気中に2秒、4秒、6秒間それぞれ暴露し、指触によりべたつきのない状態を乾燥として判断した。1~5段階で評価を行い、数値が小さいほど乾燥性が良好であることを示す。
(乳化率)
インキ3.9mlを動的乳化試験機(日本レオロジー機器(株)製)上に展開し、ロール温度30℃、200rpmにて純水を5ml/分の速度で供給、このインキ中の水分量を赤外水分計により測定した。
Claims (7)
- ジヒドロアガチン酸を0.4~10%含有するロジン類(a)、フェノール類とホルムアルデヒドの縮合物(b)、およびポリオール(c)を反応させて得られることを特徴とするロジン変性フェノール樹脂。
- 重量平均分子量が50,000~300,000である請求項1に記載のロジン変性フェノール樹脂。
- 成分(a)、成分(b)および成分(c)の使用量の合計100重量%を基準として、成分(a)の使用量が41~88重量%、成分(b)の使用量が9~50重量%、成分(c)の使用量が3~9重量%である請求項1または2記載のロジン変性フェノール樹脂。
- ジヒドロアガチン酸を0.4~10%含有するロジン類(a)、フェノール類とホルムアルデヒドの縮合物(b)、およびポリオール(c)を反応させることを特徴とするロジン変性フェノール樹脂の製造方法。
- 重量平均分子量が50,000~300,000である請求項4に記載のロジン変性フェノール樹脂の製造方法。
- 成分(a)、成分(b)および成分(c)の合計100重量%を基準として、成分(a)の使用量が41~88重量%、成分(b)の使用量が9~50重量%、成分(c)の使用量が3~9重量%である請求項4または5記載のロジン変性フェノール樹脂の製造方法。
- 請求項1~3のいずれかに記載のロジン変性フェノール樹脂を含有することを特徴とする印刷インキ。
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EP10746121.2A EP2402378A4 (en) | 2009-02-27 | 2010-02-17 | COLOPHONIUM-MODIFIED PHENOL RESIN, METHOD OF MANUFACTURING THEREOF AND PRINTING INTE |
CN2010800087594A CN102325815B (zh) | 2009-02-27 | 2010-02-17 | 松香改性酚醛树脂及其制造方法和印刷油墨 |
US13/203,825 US20120010358A1 (en) | 2009-02-27 | 2010-02-17 | Rosin-modified phenol resin, manufacturing method thereof, and printing ink |
AU2010218932A AU2010218932A1 (en) | 2009-02-27 | 2010-02-17 | Rosin-modified phenol resin, manufacturing method thereof, and printing ink |
JP2011501561A JP5582419B2 (ja) | 2009-02-27 | 2010-02-17 | ロジン変性フェノール樹脂、その製造方法および印刷インキ |
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WO2013172295A1 (ja) * | 2012-05-18 | 2013-11-21 | 荒川化学工業株式会社 | ハンダ付フラックス用ベース樹脂、ハンダ付フラックスおよびソルダペースト |
JP6338132B1 (ja) * | 2017-09-29 | 2018-06-06 | 東洋インキScホールディングス株式会社 | 平版印刷インキ用樹脂および平版印刷インキ |
JP7438620B2 (ja) | 2018-11-22 | 2024-02-27 | 東邦化学工業株式会社 | ロジンエマルションサイズ剤 |
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CN105386366A (zh) * | 2014-08-21 | 2016-03-09 | 荒川化学工业株式会社 | 松香系乳液施胶剂和纸 |
JP6525397B2 (ja) * | 2015-09-28 | 2019-06-05 | 荒川化学工業株式会社 | ロジン系エマルジョンサイズ剤及び該サイズ剤を用いて得られる紙 |
CN105385229A (zh) * | 2015-11-30 | 2016-03-09 | 苏州市博来特油墨有限公司 | 一种快干亮光环保胶印油墨 |
JP7292891B2 (ja) * | 2019-02-07 | 2023-06-19 | サカタインクス株式会社 | 活性エネルギー線硬化型インキ組成物、及びそれを用いた印刷物の製造方法 |
CN111171438A (zh) * | 2020-02-17 | 2020-05-19 | 褚乃博 | 回收材料制成的复合材料、形成方法及其应用 |
US11591488B2 (en) * | 2020-09-25 | 2023-02-28 | Toyo Ink Sc Holdings Co., Ltd. | Rosin-modified phenol resin, lithographic printing ink, and printed product |
CN116622263A (zh) * | 2023-05-22 | 2023-08-22 | 中国印钞造币集团有限公司 | 一种低voc高稳定性环保型雕刻凹印油墨及其制备方法 |
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WO2013172295A1 (ja) * | 2012-05-18 | 2013-11-21 | 荒川化学工業株式会社 | ハンダ付フラックス用ベース樹脂、ハンダ付フラックスおよびソルダペースト |
JP5545421B2 (ja) * | 2012-05-18 | 2014-07-09 | 荒川化学工業株式会社 | ハンダ付フラックス用ベース樹脂、ハンダ付フラックスおよびソルダペースト |
KR20150016218A (ko) * | 2012-05-18 | 2015-02-11 | 아라까와 가가꾸 고교 가부시끼가이샤 | 납땜 플럭스용 베이스 수지, 납땜 플럭스 및 납땜 페이스트 |
JPWO2013172295A1 (ja) * | 2012-05-18 | 2016-01-12 | 荒川化学工業株式会社 | ハンダ付フラックス用ベース樹脂、ハンダ付フラックスおよびソルダペースト |
KR101991355B1 (ko) | 2012-05-18 | 2019-06-20 | 아라까와 가가꾸 고교 가부시끼가이샤 | 납땜 플럭스용 베이스 수지, 납땜 플럭스 및 납땜 페이스트 |
JP6338132B1 (ja) * | 2017-09-29 | 2018-06-06 | 東洋インキScホールディングス株式会社 | 平版印刷インキ用樹脂および平版印刷インキ |
JP2019065106A (ja) * | 2017-09-29 | 2019-04-25 | 東洋インキScホールディングス株式会社 | 平版印刷インキ用樹脂および平版印刷インキ |
JP7438620B2 (ja) | 2018-11-22 | 2024-02-27 | 東邦化学工業株式会社 | ロジンエマルションサイズ剤 |
Also Published As
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EP2402378A1 (en) | 2012-01-04 |
JPWO2010098240A1 (ja) | 2012-08-30 |
JP5582419B2 (ja) | 2014-09-03 |
MY156766A (en) | 2016-03-31 |
CN102325815A (zh) | 2012-01-18 |
AU2010218932A1 (en) | 2011-07-28 |
EP2402378A4 (en) | 2013-12-18 |
US20120010358A1 (en) | 2012-01-12 |
CN102325815B (zh) | 2013-07-03 |
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