CN1457351A - Resin composition for printing ink and process for producing the same - Google Patents
Resin composition for printing ink and process for producing the same Download PDFInfo
- Publication number
- CN1457351A CN1457351A CN02800317A CN02800317A CN1457351A CN 1457351 A CN1457351 A CN 1457351A CN 02800317 A CN02800317 A CN 02800317A CN 02800317 A CN02800317 A CN 02800317A CN 1457351 A CN1457351 A CN 1457351A
- Authority
- CN
- China
- Prior art keywords
- weight
- printing ink
- resin composition
- solvent
- gram
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000007639 printing Methods 0.000 title claims abstract description 34
- 239000011342 resin composition Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 16
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 239000002798 polar solvent Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims description 44
- 239000011347 resin Substances 0.000 claims description 44
- 238000004519 manufacturing process Methods 0.000 claims description 35
- 150000002148 esters Chemical group 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000001336 alkenes Chemical class 0.000 claims description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000976 ink Substances 0.000 abstract description 32
- 239000000203 mixture Substances 0.000 abstract description 10
- 229920000098 polyolefin Polymers 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 4
- 125000002723 alicyclic group Chemical group 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- -1 polypropylene Polymers 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 22
- 239000004743 Polypropylene Substances 0.000 description 21
- 229920001155 polypropylene Polymers 0.000 description 21
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 17
- 235000019400 benzoyl peroxide Nutrition 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 239000003849 aromatic solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 229920006267 polyester film Polymers 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- PYOLJOJPIPCRDP-UHFFFAOYSA-N 1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1 PYOLJOJPIPCRDP-UHFFFAOYSA-N 0.000 description 1
- LHXNVCCLDTYJGT-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)propan-2-ol Chemical compound CC(O)COCC1CO1 LHXNVCCLDTYJGT-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 1
- ZXJBWUAALADCRI-UHFFFAOYSA-N 2-(octadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCCCOCC1CO1 ZXJBWUAALADCRI-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Natural products CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 210000002469 basement membrane Anatomy 0.000 description 1
- 229940043232 butyl acetate Drugs 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
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical class CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 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
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
- C08F255/023—On to modified polymers, e.g. chlorinated polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
A resin composition for toluene-free printing inks having satisfactory high-temperature stability. The composition is characterized by comprising: a graft copolymer obtained by reacting an acrylic monomer having an ethylenically unsaturated bond with an oxidized chlorinated polyolefin having a weight-average molecular weight of 3,000 to 50,000 in the presence of a polar solvent; and an alicyclic solvent.
Description
Technical field
The present invention relates to resin composition for printing ink and manufacture method thereof.More particularly, the present invention relates to as the lining of various plastic films, plastic sheet or forming synthetic resin thing with and useful and do not contain the resin composition for printing ink and the manufacture method thereof of aromatic solvents such as toluene fully.
Technical background
Make the chlorinatedpolyolefins that the printing-ink raw material is used, be insoluble in the solvent beyond the aromatic series such as toluene.And the consistency of chlorinatedpolyolefins and urethane resin is poor, and is compatible hardly in as the non-existent system of the toluene of chlorinatedpolyolefins fine solvent.In this external printing-ink, consider dry and with the solvability of resin glue, for using chlorinatedpolyolefins and for the printing-ink of polyurethane-modified chlorinatedpolyolefins, preferably using aromatic solvents such as toluene.
But usually mention the operating environment problem in recent years, require to reduce the aromatic solvent that printing-ink often uses.The print of related food film for packaging particularly, people also pay close attention to the residual solvent of printing-ink, and strong request reduces the quantity of aromatic solvents such as toluene.And use the product of toluene owing to there is the high-temperature stability problem, so the task of top priority is the good no toluene type printing resin of a kind of high-temperature stability of exploitation.
So someone proposes a kind of polyurethane-modified thing of chlorinatedpolyolefins, as the printing resin (Japan No. 252606/1989, No. 4148/1992 and No. 61024/1999 patent disclosure communique etc.) of the highly versatile of not selecting base material film.But these materials use amine resins as the chain lengthening agent when polyurethane-modified, owing to lasting with the chlorinated resin reaction colourity are risen.Its result has tonal variation big under the occasion of using in printing ink, must according to circumstances change problems such as proportioning.
The object of the invention is to provide a kind of aromatic solvents such as toluene that do not use fully, solution, high-temperature stability good and and resin for printing ink such as urethane resin, polyamide resin and nitrocellulose between good resin composition for printing ink and the manufacture method thereof of consistency.
Disclosure of an invention
The object of the invention is to provide a kind of aromatic solvents such as toluene that do not use fully, be the solution shape, high-temperature stability good and and resin for printing ink such as urethane resin, polyamide resin and nitrocellulose between good resin composition for printing ink and the manufacture method thereof of consistency.
The inventor etc. find through the further investigation back, use contains by having the resin composition for printing ink that propylene base system monomer that alkene is unsaturated link(age) and weight-average molecular weight 3000～50000 and cl content are the mixed solvent of the oxide treatment chlorinatedpolyolefins reaction of 10～50 weight the % graft copolymer, non-aromatics polar solvent and the ester ring type solvent that obtain, can address the above problem.
The oxide treatment chlorinatedpolyolefins that the present invention uses is a kind ofly can give the composition of polyolefin base material film with tack, is that chlorinatedpolyolefins obtains through oxidation.
The oxide treatment chlorinatedpolyolefins can obtain in the chlorination reaction usually easily.For example, utilize alpha-olefin copolymer to be dissolved in chloride series solvents such as chloroform after, irradiation ultraviolet radiation, the method that perhaps feeds at least a above gas of selecting in the presence of organo-peroxide simultaneously from gaseous chlorine and air, oxygen or ozone obtains.Owing to be formed with hydroxyl, carboxyl or peracid etc. at the oxide treatment chlorinatedpolyolefins, so can carry out various high molecular weight reactives.Therefore, can with have the propylene base system monomer reaction that alkene is unsaturated link(age).
The carrying out of oxidizing reaction can be by means of the 1730cm of infrared spectrophotometer mensuration
-1Near the increase that absorbs is judged.And degree of oxidation can be confirmed by the functional group's index that utilizes the following formula yardstick to measure.In order to improve through the chlorinatedpolyolefins of oxide treatment and the reactivity between the monomer, this functional group's index is preferred 5～30%, and more preferably 10～25%.
(formula)
(1730
-1Optical density(OD)/1460 at place
-1The optical density(OD) at place) * 100=functional group index
The raw material polyolefine of oxide treatment chlorinatedpolyolefins can use crystalline polypropylene, noncrystalline polypropylene, ethylene-propylene copolymer, ethylene-propylene-diene copolymer, ethylene-propylene-alpha-olefin copolymer etc.
The raw material polyolefine of oxide treatment chlorinatedpolyolefins, can use cl content is 10～50 weight %, preferred 15～40 weight %.In a single day cl content is lower than 10 weight %, will make it at esters solvents such as vinyl acetate, butylacetates, ketones solvent such as methyl ethyl ketone, methyl iso-butyl ketone (MIBK), the solvability deterioration outside the aromatic solvents such as alicyclic solvents such as hexanaphthene, methylcyclohexane, ethylcyclohexane in the solvent; When otherwise cl content surpasses 50 weight %, will become bad with the tack of polypropylene-based basement membrane.Wherein the cl content among the present invention is the numerical value of measuring according to JIS-K7229.
And it is 3000～50000 that the chlorinatedpolyolefins of oxide treatment can use weight-average molecular weight.Weight-average molecular weight is lower than at 3000 o'clock, and the cohesive force of resin is weak and bad with the tack change of base material, and surpasses under 50000 the occasion not preferred with the consistency variation of other resins.In addition, the weight-average molecular weight among the present invention is meant, is standard with the polystyrene resin, with the numerical value of gel permeation chromatography (GPC) mensuration.
The chlorinatedpolyolefins of oxide treatment is handled in toluene solution usually, but among the present invention fully without toluene.Chloroformic solution that chlorination obtains in chloroform solvent, the oxide treatment chlorinatedpolyolefins behind the interpolation stablizer (epoxy compounds etc.), is supplied with the extrusion machine solidifying formation that partly has the band bend pipe of desolventizing pumping unit at screw shaft.Solidifying formation can adopt known method to carry out with method, for example can use extruder outlet partly to have the extrusion machine of band bend pipe extrusion machine, band bend pipe of underwater cutting tablets press and the tablets press etc. that can cut off the strip resin carries out.
Can in chlorinated resin, add epoxy compounds as stablizer.Be not particularly limited for epoxy compounds, but preferred and chlorinated resin has consistency.Can enumerate epoxy equivalent (weight) is about 100～500, the compound that has an above epoxy group(ing) in molecule.For example can enumerate the epoxidised epoxidized soybean oil of vegetables oil and the epoxidized linseed that will have natural unsaturated group with peracid such as peracetic acid; Unsaturated fatty acidss such as oleic acid, ready denier oil acid and soy(a)-bean oil fatty acid are through epoxidised fatty acid ester; Epoxidation tetrahydrophthalic acid ester is the epoxidation alicyclic compound of representative; That dihydroxyphenyl propane and polyvalent alcohol and Epicholorohydrin are condensed into, for example dihydroxyphenyl propane glycidyl ether, diglycidyl ether of ethylene glycol, propylene glycol glycidyl ether, glycerol polyglycidyl ether, Sorbitol Powder polyglycidyl ether etc.; Butylglycidyl ether, 2-ethylhexyl glycidyl ether, decyl glycidyl ether, stearyl glycidyl ether, glycidyl allyl ether, phenyl glycidyl ether, secondary butyl phenenyl glycidyl ether, tert-butyl-phenyl glycidyl ether, phenol polyethylene oxide glycidyl ether etc. are the mono-epoxy compounds class of representative.But also can use organometallic compound class, hydrotalcite-based compounds such as metallic soap class, dibutyltin dilaurate, dibutyl maleinate such as the calcium stearate that uses as the stablizer of polyvinyl chloride (PVC) RESINS, lead stearate, these both can use separately also and can and use.Preferably add the stablizer of 1～5 weight % (being converted into the solid composition) with respect to the oxide treatment chlorinatedpolyolefins.
Among the present invention, in the presence of the non-aromatic polar solvent, use polymerization initiator to make to utilize oxide treatment polyolefine that aforesaid method obtains and have the acrylic monomer reaction that alkene is unsaturated link(age), can obtain graft copolymer.
The non-aromatic polar solvent that the present invention uses can be enumerated esters solvent or ketones solvent.Esters solvent can be enumerated vinyl acetic monomer, butylacetate etc.And ketones solvent can be enumerated acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) etc.These solvents can be used singly or in combination.The polar solvent amount preferably makes oxide treatment chlorinatedpolyolefins solid components and concentration be in 40～80 weight % scopes during reaction.In case exceed this scope, the grafting efficiency that has alkene and be the acrylic monomer of unsaturated link(age) will reduce, and solution state is worsened.
Among the present invention, also can use the mixed solvent that in above-mentioned polar solvent, has mixed less than 30 weight % ester ring type solvents to react.Can enumerate hexanaphthene, methylcyclohexane, ethylcyclohexane, dimethyl cyclohexane, pentamethylene, methylcyclopentane, ethyl cyclopentane and to terpane etc. as the ester ring type solvent.Ester ring type solvent in the mixed solvent is if surpass 30 weight %, and the monomeric grafting efficiency of propylene base system that then has alkene and be unsaturated link(age) reduces, and solution state is worsened, but also can make and the consistency variation of other resins such as urethane of usefulness, so bad.
The polymerization initiator of reaction usefulness can suitably be selected from known polymerization starter, but preferred organo-peroxide.For example can enumerate benzoyl peroxide, dialkyl peroxide, ketone peroxide, ester superoxide, diacyl peroxide etc.And temperature of reaction can implement in the following scope of the boiling point of normal temperature～solvent, the reaction times be 1～10 hour be suitable.
That uses among the present invention has a propylene base system monomer that alkene is unsaturated link(age), be meant the propylene base system monomer that in the molecule alkene to be arranged be unsaturated link(age), for example glycidyl acrylate, glycidyl methacrylate, vinylformic acid 2-hydroxy methacrylate, 2-hydroxyethyl methacrylate, acrylic or methacrylic acid etc.These monomers can use separately or multiple and usefulness.
The propylene base system monomer that has alkene among the present invention and be unsaturated link(age) preferably is in 1～50 weight % scope with respect to the polyolefinic ratio of oxide treatment.When being lower than 1 weight %, the consistency of other resins such as urethane and above-mentioned solvent is poor, on the contrary the consistency that surpasses under the occasion of 50 weight % not only with above-mentioned solvent worsen, and can generate insoluble homopolymer, separate out sometimes, use so be not suitable as resin for printing ink.
Resin composition for printing ink of the present invention is the material that further mixes the ester ring type solvent in the graftomer that obtains according to the method described above.As the ester ring type solvent, can use above-mentioned solvent.Resin for printing ink composition of the present invention is preferably allocated the ester ring type solvent that accounts for whole solvent composition 10～90 weight % ratios into.The ester ring type solvent is lower than 10 weight % or is higher than under the occasion of 90 weight %, and solution state is bad and bad.
Resin composition for printing ink of the present invention, the viewpoint of when printing ink is made, handling, preferred 30～70 weight % of resin solid components and concentration.Resin composition for printing ink of the present invention, both can directly make printing ink and use, use after also can in the scope that does not influence effect of the present invention, adding resin such as urethane resin, polyamide resin, polyester polyol resin, cellulose acetate butyrate, soluble cotton and pigment, solvent and other additives.
The best mode that carries out an invention
The invention is characterized in, by using the mixed solvent of non-aromatic polar solvent or this polar solvent and ester ring type solvent, as the solvent of the chlorinatedpolyolefins that makes oxide treatment when to have alkene be the propylene base system monomer reaction of unsaturated link(age), it is good to obtain a kind of consistency with resin for printing ink such as urethane resin, vibrin, nitrocellulose, and the also good resin for printing ink composition this point of high-temperature stability.
For the chlorinatedpolyolefins that improves oxide treatment and the consistency of urethane resin, polyamide resin and nitrocellulose etc., it is believed that in the chlorinatedpolyolefins of oxide treatment, to import to have the propylene base system monomer that alkene is unsaturated link(age), crucial with the polar that improves resin.It is believed that in addition, in the presence of the mixed solvent of non-aromatic polar solvent or this polar solvent and ester ring type solvent, is that the graft copolymer that the monomer-grafted polymerization of propylene base system of unsaturated link(age) obtains is dissolved in the ester ring type solvent with the chlorinatedpolyolefins of oxide treatment with having alkene, also is the reason that the consistency with various resins is improved.
Embodiment
Below further describe the present invention with embodiment, but the present invention is not subjected to the restriction of these embodiment.
(trial-production example 1)
Isotatic polypropylene with 160 ℃ of about 4000mPas of following melt viscosity of 300 grams feeds intake in glass-lined kettle.To wherein adding 5 liters of chloroforms, under 2 kilograms/cm2 pressure, the limit feeds chlorine and oxygen with the uviolizing limit, make it chlorination and reach 20% to functional group's index, when cl content reaches 32 weight % till.Add epoxy compounds (ェ Port サ ィ ザ-W-100EL that 18 gram used as stabilizers are used behind the reaction terminating, Dainippon Ink and Chemicals, Inc's system), infeed screw shaft and partly have the band bend pipe extrusion machine (double-screw extrusion machine of desolventizing pumping unit, KZW40-34MG, テ Network ノ ベ Le Co., Ltd. system), desolventizing and solidifying formation.The weight-average molecular weight of the oxide treatment Chlorinated Polypropylene III that obtains is 11000.
(trial-production example 2)
Isotatic polypropylene with 160 ℃ of about 4200mPas of following melt viscosity of 300 grams feeds intake in glass-lined kettle.To wherein adding 5 liters of chloroforms, under 2 kilograms/cm2 pressure, the limit feeds chlorine and oxygen with the uviolizing limit, and chlorination reaches 23% to functional group's index, when cl content reaches 39 weight % till.Add the epoxy compounds (ェ ピ ォ-Le SB, NOF Corp's system) that 18 gram used as stabilizers are used behind the reaction terminating, similarly implement desolventizing and solidifying formation with trial-production example 1.The weight-average molecular weight of the oxide treatment Chlorinated Polypropylene III that obtains is 18000.
(trial-production example 3)
Isotatic polypropylene with 160 ℃ of about 4200mPas of following melt viscosity of 300 grams feeds intake in glass-lined kettle.To wherein adding 5 liters of chloroforms, under 2 kilograms/cm2 pressure, the limit feeds chlorine and oxygen with the uviolizing limit, and chlorination reaches 18% to functional group's index, when cl content reaches 68 weight % till.Add the epoxy compounds (ェ ピ ォ-Le SB, NOF Corp's system) that 18 gram used as stabilizers are used behind the reaction terminating, similarly implement desolventizing and solidifying formation with trial-production example 1.The weight-average molecular weight of the oxide treatment Chlorinated Polypropylene III that obtains is 10000.
(embodiment 1)
The Chlorinated Polypropylene IIIs of the 380 gram oxide treatment that adding trial-production example 1 obtains in the four-hole boiling flask that has stirrer, thermometer, reflux exchanger and nitrogen ingress pipe and 200 gram ethyl acetate are 70 ℃ of following heating for dissolving.Then add 3.8 gram benzoyl peroxides (BPO made in following brief note), keep in 3 hours, adding after 10 minutes 20 gram 2-hydroxyethyl methacrylic esters (2-HEMA made in following brief note).Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.To wherein adding 200 gram methylcyclohexanes (MCH made in following brief note), make the resin combination of solid components and concentration 50 weight % again.
(embodiment 2)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 400 gram oxide treatment that adding trial-production example 2 obtains, 40 gram MCH and 360 gram ethyl acetate are 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 20 gram 2-HEMA.Remain on then and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.To wherein adding 20 gram MCH, make the resin combination of solid components and concentration 50 weight % again.
(embodiment 3)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 320 gram oxide treatment that adding trial-production example 2 obtains, 20 gram MCH and 150 gram ethyl acetate are 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 80 gram 2-HEMA.Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.To wherein adding 230 gram MCH, make the resin combination of solid components and concentration 50 weight % again.
(embodiment 4)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 380 gram oxide treatment that adding trial-production example 2 obtains, 20 gram MCH and 150 gram ethyl acetate are 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 20 gram glycidyl methacrylate (GMA made in following brief note).Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.To wherein adding 230 gram MCH, make the resin combination of solid components and concentration 50 weight % again.
(embodiment 5)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 400 gram oxide treatment that adding trial-production example 1 obtains, 40 gram ethylcyclohexanes (ECH made in following brief note) and 200 gram ethyl acetate are 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 20 gram 2-HEMA.Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.To wherein adding 180 gram ECH, make the resin combination of solid components and concentration 50 weight % again.
(comparative example 1)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 380 gram oxide treatment that adding trial-production example 1 obtains and 400 gram MCH are 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 20 gram 2-HEMA.Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.The solid components and concentration of the graft copolymer solution that obtains is 50 weight %, makes resin combination with it.
(comparative example 2)
Use the reactor of embodiment 1 usefulness, add the Chlorinated Polypropylene III and the 400 gram ethyl acetate of manufacturing experimently routine-2 380 gram oxide treatment that obtain, 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 20 gram 2-HEMA.Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.The solid components and concentration of the graft copolymer solution that obtains is 50 weight %, makes resin combination with it.
(comparative example 3)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 380 gram oxide treatment that adding trial-production example 3 obtains, 200 gram MCH and 200 gram ethyl acetate are 70 ℃ of following heating for dissolving.Then add 3.8 gram BPO, keep in 3 hours, adding after 10 minutes 20 gram 2-HEMA.Then, remain on and make it to react 3 hours under 70 ℃, obtained graft copolymer solution.The solid components and concentration of the graft copolymer solution that obtains is 50 weight %, makes resin combination with it.
(comparative example 4)
Use the reactor of embodiment 1 usefulness, the Chlorinated Polypropylene IIIs of the 400 gram oxide treatment that adding trial-production example 1 obtains, 200 gram MCH and 200 gram ethyl acetate are 70 ℃ of following heating for dissolving.Having obtained the solid components and concentration is the chlorinated polypropylene solution of the oxide treatment of 50 weight %.Make resin combination with it.
(comparative example 5)
Use the reactor of embodiment 1 usefulness, add Chlorinated Polypropylene III, 47 gram MCH and the 267 gram ethyl acetate of manufacturing experimently routine-2 400 gram oxide treatment that obtain, 60 ℃ of following heating for dissolving.Add 71 grams then by 2,2,4-trimethyl cyclohexane glycol and hexanodioic acid polycondensation obtain, hydroxyl value is the pure and mild 31 gram isophorone diisocyanates of the polyester polyols of 112KOHmg/g, makes it to react 8 hours.Then add 6 gram isophorone diamines, 85 gram MCH and 101 gram Virahols (IPA made in following brief note) under agitation make it to react 2 hours under 40 ℃.The solid components and concentration of the polyurethane-modified oxide treatment chlorinated polypropylene solution that obtains is 50 weight %, makes resin combination with it.
In the raw material that uses in embodiment 1～5 and the comparative example 1～4, the reaction conditions illustration table 1.
Table 1
Solution composition during reaction
※ 1: polar solvent/ester ring type solvent (weight ratio)
| Resin kind weight (g) | Solution composition during reaction ※1(the ratio % of ester ring type solvent) | Propylene base system monomeric species weight (g) (the ratio % in the resin) | The addition of ester ring type solvent (g) in the graft copolymer | The ratio (%) of ester ring type solvent in whole solvents | |
| Embodiment 1 | Trial-production example 1 380 | ??200/0 ??(0) | 2-HEMA???20 ?????????(5.3) | ??200 | ??50.0 |
| Embodiment 2 | Trial-production example 2 400 | ??360/40 ??(10.0) | 2-HEMA???20 ?????????(5.0) | ??20 | ??14.3 |
| Embodiment 3 | Embodiment 2 320 | ??150/20 ??(11.8) | 2-HEMA???80 ?????????(25.0) | ??230 | ??62.5 |
| Embodiment 4 | Trial-production example 2 380 | ??150/20 ??(11.8) | GMA??????20 ?????????(5.3) | ??230 | ??62.5 |
| Embodiment 5 | Trial-production example 1 400 | ??200/40 ??(16.7) | 2-HEMA???20 ?????????(5.3) | ??180 | ??52.4 |
| Comparative example 1 | Trial-production example 1 380 | ??0/400 ??(100) | 2-HEMA???20 ?????????(5.3) | ??0 | ??100 |
| Comparative example 2 | Trial-production example 2 380 | ??400/0 ??(0) | 2-HEMA???20 ?????????(5.3) | ??0 | ??0 |
| Comparative example 3 | Trial-production example 3 380 | ??200/200 ??(50) | 2-HEMA???20 ?????????(5.3) | ??0 | ??50.0 |
| Comparative example 4 | Trial-production example 1 400 | ??200/200 ??(50) | - ?????????(0) | ??0 | ??50.0 |
Below the resin combination that obtains with regard to each embodiment carried out following test.
High-temperature stability
For the resin combination that obtains in embodiment 1～5 and the comparative example 1～5, after one month, observe the variation that its colourity (Gardner's colourity) is accompanyed or follow the time in preservation under 50 ℃ immediately after the manufacturing.The results are shown among the table 2.
Compatibility test
With solid composition weight ratio 1/9, with resin combination and (Sanyo Chemical Industries, Ltd.'s manufacturing of printing ink urethane resin that obtains in embodiment 1～5 and the comparative example 1～5, サ Application プ レ Application IB-422) or vibrin (Sumitomo バ ィ ゥ レ Application Co., Ltd. makes, デ ス モ Off ェ Application 670) mix, making all resins concentration in ethyl acetate is 30 weight % solution.Visual observation obtains the method evaluation of mixed resin solution state.The results are shown among the table 2.Judgement criteria in the table 2: ◎ is limpid (do not have and separate); * be bad (precipitation is arranged).
Table 2
| Colourity 50 ℃ * 1 month | Consistency | ||
| Urethane resin | Vibrin | ||
| Embodiment 1 | No change | ????◎ | ????◎ |
| Embodiment 2 | No change | ????◎ | ????◎ |
| Embodiment 3 | No change | ????◎ | ????◎ |
| Embodiment 4 | No change | ????◎ | ????◎ |
| Embodiment 5 | No change | ????◎ | ????◎ |
| Comparative example 1 | No change | ????× | ????× |
| Comparative example 2 | No change | ????× | ????× |
| Comparative example 3 | No change | ????× | ????× |
| Comparative example 4 | No change | ????× | ????× |
| Comparative example 5 | 5 (initial stage) → 10 | ????◎ | ????◎ |
Adhesive test
The mixed resin solution (30 weight % solution) that uses compatibility test to use mixes following material, makes white printing-ink after mediating with the coating vibrator.
40 parts of mixing solutionss
30 parts of pigment (titanium white)
20 parts of ethyl acetate
15 parts of IPA
The white printing-ink that will obtain with 10# mayer rod (マ ィ ャ-バ-) is coated with and is contained on stretched polypropylene films (OPP), polyester film (PET), the nylon membrane (NY).On application face, stick the fragrant adhesive tape of match fine jade, the state of application face when observing fast with tape stripping.The results are shown among the table 3.In the table 3, ◎ represents fabulous, and zero expression is good, and △ represents poor slightly, and * expression is bad.
Table 3 adhesive test result
| With the mixture of printing ink with urethane resin | Mixture with vibrin | |||||
| ????OPP | ????PET | ????NY | ????OPP | ????PET | ????NY | |
| Embodiment 1 | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ |
| Embodiment 2 | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ |
| Embodiment 3 | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ |
| Embodiment 4 | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ |
| Embodiment 5 | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ |
| Comparative example 1 | ????△ | ????○ | ????○ | ????△ | ????○ | ????○ |
| Comparative example 2 | ????△ | ????○ | ????○ | ????△ | ????○ | ????○ |
| Comparative example 3 | ????× | ????○ | ????○ | ????× | ????○ | ????○ |
| Comparative example 4 | ????◎ | ????× | ????× | ????◎ | ????× | ????× |
| Comparative example 5 | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ | ????◎ |
The possibility of utilizing on the industry
The presentation of results of table 2 and table 3, resin composition for printing ink of the present invention, high-temperature stability is good, and also good with the compatibility of Polyurethane Resins for Inks or mylar. In addition, has good cementability for the various resin moldings that are called OPP, PET, NY, so can be used for industry.
In addition, resin composition for printing ink of the present invention, in manufacturing process because fully without aromatic series series solvents such as toluene, so also good on environment.
Claims (8)
1. resin composition for printing ink, wherein contain by have propylene base system monomer that alkene is unsaturated link(age) and weight-average molecular weight be 3000～50000 and cl content be the graft copolymer that generates of the oxide treatment chlorinatedpolyolefins reaction of 0～50 weight % and the mixed solvent of non-aromatic polar solvent and ester ring type solvent.
2. according to the described resin composition for printing ink of claim 1, it is characterized in that the resin solid components and concentration is 30～70 weight %.
3. according to claim 1 or 2 described resin composition for printing ink, it is characterized in that containing in the described mixed solvent 10～90 weight % ester ring type solvents.
4. according to each described resin composition for printing ink in the claim 1～3, it is characterized in that described to have alkene be that the propylene base system monomer of unsaturated link(age) is 1～50 weight % with respect to said oxide treatment chlorinatedpolyolefins content.
5. the manufacture method of a resin composition for printing ink, it is characterized in that in the presence of the non-aromatic polar solvent, make and have the propylene base system monomer that alkene is unsaturated link(age), with weight-average molecular weight be 3000～50000 and also cl content be the oxide treatment chlorinatedpolyolefins reaction of 10～50 weight %, remix ester ring type solvent in the graft copolymer that obtains.
6. according to the manufacture method of the described resin composition for printing ink of claim 5, it is characterized in that mixing the ratio of ester ring type solvent, be in 10～90 weight % scopes with respect to whole solvents.
7. according to the manufacture method of claim 5 or 6 described resin composition for printing ink, the propylene base system monomer that it is characterized in that having alkene and be unsaturated link(age) is 1～50 weight % with respect to the ratio of oxide treatment chlorinatedpolyolefins.
8. according to the manufacture method of each described resin composition for printing ink in the claim 5～7, it is characterized in that in the presence of the mixed solvent of non-aromatic polar solvent and the following ester ring type solvent of 30 weight %, reacting.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP039974/2001 | 2001-02-16 | ||
| JP2001039974 | 2001-02-16 | ||
| JP2001396542A JP4240882B2 (en) | 2001-02-16 | 2001-12-27 | Resin composition for printing ink and method for producing the same |
| JP396542/2001 | 2001-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1457351A true CN1457351A (en) | 2003-11-19 |
Family
ID=26609529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN02800317A Pending CN1457351A (en) | 2001-02-16 | 2002-02-05 | Resin composition for printing ink and process for producing the same |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4240882B2 (en) |
| KR (1) | KR20020093916A (en) |
| CN (1) | CN1457351A (en) |
| WO (1) | WO2002064690A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250512A (en) * | 2011-01-19 | 2011-11-23 | 一可油墨涂料（深圳）有限公司 | Screen printing ink for polypropylene material |
| CN105263970A (en) * | 2013-03-22 | 2016-01-20 | 日本制纸株式会社 | Chlorinated polyolefin resin |
| CN110461934A (en) * | 2017-03-17 | 2019-11-15 | 日本制纸株式会社 | Chloridized polyolefin based resin composition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL209142B1 (en) | 2003-02-18 | 2011-07-29 | Fujikura Kasei Kk | Acrylic-modified chlorinated polyolefin resin, process for producing the same, and coating composition containing the same for polyolefin material |
| EP3196218B1 (en) | 2014-08-29 | 2020-05-27 | Nippon Paper Industries Co., Ltd. | Block copolymer and resin composition |
| JP6585350B2 (en) * | 2015-01-19 | 2019-10-02 | サカタインクス株式会社 | Printing ink composition for shrink packaging and printed matter for shrink packaging |
| EP3521329B1 (en) | 2016-09-28 | 2024-11-06 | Nippon Paper Industries Co., Ltd. | Modified polyolefin resin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2813143B2 (en) * | 1994-09-27 | 1998-10-22 | 日本製紙株式会社 | Aqueous resin composition |
| JP2848588B2 (en) * | 1996-09-11 | 1999-01-20 | 日本製紙株式会社 | Resin composition |
| JP3328928B2 (en) * | 1998-05-22 | 2002-09-30 | 日本製紙株式会社 | Resin composition for printing ink and method for producing the same |
-
2001
- 2001-12-27 JP JP2001396542A patent/JP4240882B2/en not_active Expired - Fee Related
-
2002
- 2002-02-05 KR KR1020027013831A patent/KR20020093916A/en not_active Application Discontinuation
- 2002-02-05 WO PCT/JP2002/000908 patent/WO2002064690A1/en active Application Filing
- 2002-02-05 CN CN02800317A patent/CN1457351A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250512A (en) * | 2011-01-19 | 2011-11-23 | 一可油墨涂料（深圳）有限公司 | Screen printing ink for polypropylene material |
| CN102250512B (en) * | 2011-01-19 | 2013-07-31 | 深圳市美丽华油墨涂料有限公司 | Screen printing ink for polypropylene material |
| CN105263970A (en) * | 2013-03-22 | 2016-01-20 | 日本制纸株式会社 | Chlorinated polyolefin resin |
| CN105263970B (en) * | 2013-03-22 | 2017-05-31 | 日本制纸株式会社 | chlorinated polyolefin resin |
| CN110461934A (en) * | 2017-03-17 | 2019-11-15 | 日本制纸株式会社 | Chloridized polyolefin based resin composition |
| US11518872B2 (en) | 2017-03-17 | 2022-12-06 | Nippon Paper Industries Co., Ltd. | Chlorinated polyolefin resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002064690A1 (en) | 2002-08-22 |
| KR20020093916A (en) | 2002-12-16 |
| JP4240882B2 (en) | 2009-03-18 |
| JP2002317137A (en) | 2002-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR890002431B1 (en) | Compatibilized of acrylic ester | |
| CN1597772A (en) | Radiation-curable resins based on ketone-aldehyde and/or urea-aldehyde resins and a process for preparing them | |
| CN1457351A (en) | Resin composition for printing ink and process for producing the same | |
| CN104725588A (en) | Method for preparing solvent-free negative/non-ionic water-based polyurethane-acrylate grafted copolymer with IPN structure | |
| JPH09278975A (en) | Water-based resin composition | |
| JP3318925B2 (en) | Binder resin composition and its production method and use | |
| AU2016299363A1 (en) | Coating compositions | |
| WO2020031916A1 (en) | Modified polyolefin resin, aqueous dispersion, and primer | |
| JP2004515563A (en) | Polymers with hydroxyl functionality in the side chain | |
| JPH059298A (en) | Polyolefin copolymer grafted with polycaprolactone and preparation thereof | |
| US6555621B1 (en) | Binder resin composition and process for the production thereof | |
| JPH11323236A (en) | Resin composition for printing ink and its production | |
| JP3045498B2 (en) | Binder resin composition and method for producing the same | |
| JP2001114961A (en) | Binder resin composition and its preparation method | |
| JP3965697B2 (en) | Chlorinated polyolefin binder resin composition with good solvent resistance | |
| JP2000007979A (en) | Coating resin composition for polyolefin and its production | |
| JP3073916B2 (en) | Coating composition for plasticized vinyl chloride resin and molded article of plasticized vinyl chloride resin coated with the composition | |
| JP2599630B2 (en) | Polyolefin-polyester graft copolymer and method for producing the same | |
| JP2002226755A (en) | Printing ink composition | |
| JP3133258B2 (en) | Release treatment agent | |
| JP2001064396A (en) | Coating resin composition for polyolefinic resin | |
| CN1041955A (en) | Block and graft copolymer and its production and application | |
| JP3133256B2 (en) | Modified polyvinyl alcohol-based copolymer, method for producing the same, and coating composition for plasticized vinyl chloride-based resin molded article | |
| JP3277618B2 (en) | Graft copolymer, method for producing the same, and plasticizer containing the copolymer as an active ingredient | |
| JPH09302032A (en) | Modified polyvinyl alcohol copolymer and coating composition for plasticized vinyl chloride resin molding |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |