WO2010116743A1 - 耐溶剤性に優れるフレキソ印刷用感光性樹脂組成物 - Google Patents
耐溶剤性に優れるフレキソ印刷用感光性樹脂組成物 Download PDFInfo
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- WO2010116743A1 WO2010116743A1 PCT/JP2010/002568 JP2010002568W WO2010116743A1 WO 2010116743 A1 WO2010116743 A1 WO 2010116743A1 JP 2010002568 W JP2010002568 W JP 2010002568W WO 2010116743 A1 WO2010116743 A1 WO 2010116743A1
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- Prior art keywords
- photosensitive resin
- resin composition
- flexographic printing
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- mass
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- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- MZZSDCJQCLYLLL-UHFFFAOYSA-N Secalonsaeure A Natural products COC(=O)C12OC3C(CC1=C(O)CC(C)C2O)C(=CC=C3c4ccc(O)c5C(=O)C6=C(O)CC(C)C(O)C6(Oc45)C(=O)OC)O MZZSDCJQCLYLLL-UHFFFAOYSA-N 0.000 description 1
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- 150000001253 acrylic acids Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
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- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- DWRDTESCPZZBBH-FOCLMDBBSA-N bis(3-phenylpropyl) (e)-but-2-enedioate Chemical compound C=1C=CC=CC=1CCCOC(=O)/C=C/C(=O)OCCCC1=CC=CC=C1 DWRDTESCPZZBBH-FOCLMDBBSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 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
- STDUJGRYOCDXBT-VGFSZAGXSA-N didocosyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCCCCCCCCCCCC STDUJGRYOCDXBT-VGFSZAGXSA-N 0.000 description 1
- HEJZJSIRBLOWPD-WCWDXBQESA-N didodecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-WCWDXBQESA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- XHSDDKAGJYJAQM-ULDVOPSXSA-N dioctadecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCCCCCCCC XHSDDKAGJYJAQM-ULDVOPSXSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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- 239000010419 fine particle Substances 0.000 description 1
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920003046 tetrablock copolymer Polymers 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Images
Classifications
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
Definitions
- the present invention relates to a photosensitive resin composition for flexographic printing and a photosensitive resin plate material for flexographic printing, and more specifically to an ink containing an organic solvent, such as an emulsion ink, a UV curable ink, or an ink using vegetable oil or light naphtha.
- an organic solvent such as an emulsion ink, a UV curable ink, or an ink using vegetable oil or light naphtha.
- a flexible photosensitive resin composition for flexographic printing which is excellent in image reproducibility and printing durability
- a photosensitive resin plate for flexographic printing in which the photosensitive resin composition for flexographic printing is laminated Regarding materials.
- a photosensitive resin composition for flexographic printing generally contains a thermoplastic elastomer, a photopolymerizable unsaturated monomer, a plasticizer, and a photopolymerization initiator.
- a polyester film or the like is used as a support, and the photosensitive resin composition is further formed thereon, and further for the purpose of preventing adhesion with a negative film on the photosensitive resin composition.
- a slip layer, a protective layer, or an ultraviolet shielding layer containing an infrared sensitive material that can be ablated by an infrared laser is provided.
- a flexographic printing plate from such a photosensitive resin plate material for a flexographic printing plate, first, the entire surface is exposed to ultraviolet rays (back exposure), a thin uniform cured layer (floor layer) is provided, and then Image exposure (relief exposure) is performed directly on the surface of the photosensitive resin layer through the negative film or on the ultraviolet shielding layer on which the photomask is formed by an infrared laser, and the unexposed portion is washed away with a developing solvent, or In general, it is produced by post-processing exposure after absorption and removal by an absorption layer after heat melting.
- ink is supplied to the surface of the convex portion of the uneven resin plate with an ink supply roll or the like, and then the resin plate is brought into contact with the substrate. Then, the ink on the surface of the convex portion is transferred to the printing medium.
- general inks for flexographic printing include water-based inks, emulsion inks, organic solvent-based inks such as UV curable inks or inks using vegetable oils or light naphtha.
- Patent Document 3 in order to improve resistance to UV curable printing ink, at least one elastomeric binder, a photopolymerizable unsaturated monomer, a photopolymerization initiator, and, if necessary, a dye or pigment
- a photosensitive resin composition containing a polymerization inhibitor, an antioxidant and a photodegradation inhibitor has been proposed.
- the examples include various binder mixtures of plastic elastomeric block copolymers with other block copolymers, two photopolymerizable monomers, benzyl dimethyl ketal as a photoinitiator, antioxidants.
- a photosensitive resin composition comprising a dye.
- Patent Document 4 discloses an elastomer resin, a hydrogenated terpene resin having a weight average molecular weight of 2000 or less, an unsaturated bond amount of 0.5 mol / 100 g or less, and a refractive index at 20 ° C. of 1.497 or more, a photopolymerizable unsaturated.
- a photosensitive resin composition including a monomer, a photopolymerization initiator, and, if necessary, a dye, a pigment, a polymerization inhibitor, an antioxidant, and a photodegradation inhibitor has been proposed.
- the examples include a photosensitive resin composition comprising a styrene-isoprene-styrene copolymer, a hydrogenated terpene resin, two photopolymerizable monomers, and benzyldimethyl ketal as a photopolymerization initiator. It is shown.
- Patent Document 5 in order to improve resistance to ink containing a solvent or the like, a butyl rubber having an SP value of less than 8.1, a monomer having an ethylenically unsaturated bond, a photopolymerization initiator, a water-dispersible latex, and A photosensitive resin composition containing a dye, a pigment, a polymerization inhibitor, an antioxidant, and a photodegradation inhibitor has been proposed as necessary. Examples include butyl rubber, polyisoprene rubber, carboxylated nitrile rubber, butadiene rubber, water dispersible latex / hydrophilic monomer mixture, three photopolymerizable monomers, and benzyldimethyl as a photoinitiator. A photosensitive resin composition containing a ketal is shown.
- Patent Document 6 includes, for example, a system in which a styrene-isoprene-styrene block polymer, a liquid polybutadiene having a hydroxyl end, a compound having acrylic acid and a phenol structure, and a compound containing at least one of phosphorus, sulfur, nitrogen, and boron are blended Describes a photosensitive resin composition containing an ethylenically unsaturated compound, 1,6-hexanediol dimethacrylate obtained by transesterification at 80 to 90 ° C. for 4 hours, and a photopolymerization initiator.
- Patent Document 7 for example, a polystyrene-polybutadiene-polystyrene block copolymer, a conjugated diene-based ethylenic polymer produced from a hydroxyl group-containing polybutadiene and acrylic acid, hexamethylene dimethacrylate, and a photopolymerization initiator are included.
- a functional resin composition and a flexographic printing plate precursor using the same are described.
- the problem of the present invention is that it has excellent resistance to ink containing organic solvent and emulsion ink, such as UV curable ink or vegetable oil or light naphtha, and printing applications such as image reproducibility and printing durability.
- Another object of the present invention is to provide a photosensitive resin composition for flexographic printing that simultaneously satisfies the excellent suitability of the flexographic printing, and a photosensitive resin plate material for flexographic printing in which the photosensitive resin composition for flexographic printing is laminated.
- the present invention is as follows.
- Component (c): One or more ethylenically unsaturated groups A photosensitive resin composition for flexographic printing, comprising a photopolymerizable unsaturated monomer having a component (d): a photopolymerization initiator, (2)
- Component (a) is 18.0 to 95.0 mass%
- Component (b) is 1.0 to 80.0 mass%
- Component (c) is 1.0 to 30.0 mass%
- Component (D) is contained in the range of 0.1 to 10.0% by mass, the photosensitive resin composition for flexographic printing according to the above (1), (3)
- Component (D) is contained in the range of 0.1 to 10.0% by mass, the photosensitive resin composition for flexographic printing according to the above (1), (3)
- Component (D) is contained in the range
- a photosensitive resin composition for flexographic printing according to claim 2, and (5) The present invention relates to a photosensitive resin plate material for flexographic printing, characterized in that the photosensitive resin composition for flexographic printing according to any one of (1) to (4) above is laminated on the surface of a support.
- FIG. 2 is a cross-sectional view taken along the line AA ′ of FIG.
- the photosensitive resin composition for flexographic printing of the present invention comprises the following (a) to (d) as essential components.
- thermoplastic elastomer as component (a) include styrene-isoprene-styrene copolymer (hereinafter sometimes referred to as SIS), styrene-butadiene-styrene copolymer (hereinafter referred to as SBS).
- SIS styrene-isoprene-styrene copolymer
- SBS styrene-butadiene-styrene copolymer
- SIBS Styrene-isoprene-butadiene-styrene copolymer
- SEBS styrene-ethylene-butylene-styrene copolymer
- SEPS syndiotactic 1,2-polybutadiene
- RB syndiotactic 1,2-polybutadiene
- the SIS and SBS used in the present invention are excellent in rubber elasticity and moldability, and are easily available.
- the number average molecular weight of these triblock copolymers is in the range of 2,000 to 100,000 for non-elastomeric blocks and 250,000 to 1,000,000 for elastomer blocks as measured by GPC using polystyrene as a standard substance. It is desirable to be. The reason is that if the above range is exceeded, the performance of the photosensitive resin composition deteriorates. That is, if the molecular weight of the non-elastomeric block is too small, cold flow properties remain in the composition, and if it is too large, rubber elasticity is impaired. If the molecular weight of the elastomer block is small, it is difficult to obtain rubber elasticity, and if it is too large, the cold flow property is high.
- the number average molecular weight of the tetrablock copolymer is 2,000 to 200,000 for non-elastomeric blocks and the elastomer block for GPC measurement using polystyrene as a standard substance.
- a range of 250,000 to 2,000,000 is desirable. The reason is that if the above range is exceeded, the performance of the photosensitive resin composition deteriorates. That is, if the molecular weight of the non-elastomeric block is too small, cold flow properties remain in the composition, and if it is too large, rubber elasticity is impaired.
- the RB used in the present invention is a low crystallinity elastomer and is reactive and preferably has a 1,2 bond content of 85% or more and a crystallinity in the range of 10 to 50%.
- the degree of crystallinity increases, it becomes harder, and when the degree of crystallinity decreases due to the loss of rubber elasticity, the physical properties decrease.
- the compounding amount of component (a) in the photosensitive resin composition for flexographic printing of the present invention is usually preferably 18.0 to 95.0% by mass, more preferably 50 to 80% by mass. The reason is that when it is less than 18.0% by mass, the physical strength is inferior, and when it exceeds 95.0% by mass, the productivity is inferior and the desired hardness cannot be obtained. Because.
- Component (b) is a liquid polymer having a structure in which one or more methacryloyl groups or acryloyl groups are introduced into liquid polybutadiene molecules containing 80% or more of 1,2-bonds.
- a structure in which the functional group is introduced at the terminal is preferable. Specifically, the following repeating unit (1) by 1,2-bond and repeating unit (2) by 1,4-bond
- the molar ratio of (1) and (2) is M (1) / [M (1) + M (2)] ⁇ 0.8.
- M (1) and M (2) represent the number of moles of (1) and (2), respectively.
- the wavy line in the repeating unit (2) by 1,4-bond indicates that either a trans bond or a cis bond may be used, and the repeating unit (2) by 1,4-bond has a trans isomer, a cis isomer, or a mixture thereof The other end may be present, and at one end, the following formula (3)
- R 1 represents a hydrogen atom or a methyl group
- a single or copolymer having a functional group of formula (3) or a residue of a polymerization initiator at the other end can be illustrated.
- the copolymer include a random copolymer, a block copolymer, and an alternating copolymer. Since component (b) has at least one ethylenically unsaturated group in its molecular structure, thermal polymerization or photopolymerization with a peroxide or a photopolymerization initiator is possible. Further, the compatibility with the essential components (a), (c), and (d) is very good.
- the number average molecular weight is 200 to 100,000, preferably in the range of 1000 to 100,000, and the viscosity at 45 ° C. is preferably 4 Pa ⁇ s or more, more preferably 10 Pa ⁇ s or more. If the molecular weight is too small, rubber elasticity after curing of the photosensitive resin composition is impaired. Moreover, when the viscosity of a liquid polymer becomes small, the cold flow property of the photosensitive resin composition will fall.
- the amount of component (b) is preferably 1.0 to 80.0% by mass, more preferably 5.0 to 50.0% by mass. When it is less than 5.0% by mass, the crosslinking density is low and sufficient solvent resistance cannot be obtained. When it exceeds 50.0% by mass, desired hardness and rubber elasticity cannot be obtained after curing.
- a (meth) acryl-modified liquid polybutadiene containing 80% or more of 1,2-bonds may be a commercially available product, or can be produced by a known method.
- a (meth) acryl group can be introduced by reacting a hydroxyl group of a hydroxyl group-containing polybutadiene with a compound having a (meth) acryl group.
- the compound having a (meth) acrylic group include (meth) acrylic acids such as acrylic acid and methacrylic acid, (meth) acrylic acid esters such as methyl acrylate, methyl methacrylate, ethyl acrylate, and ethyl methacrylate.
- the method for introducing a (meth) acrylic group is a method of dehydrating condensation of (meth) acrylic acid and a hydroxyl group of polybutadiene using p-toluenesulfonic acid as a catalyst, a titanium catalyst, a tin catalyst or the like as a catalyst (
- a method of reacting a hydroxyl group of polybutadiene is known.
- component (c) Specific examples of the component (c) according to the present invention include esters such as methyl (meth) acrylate, dimethyl fumarate, and dimethyl maleate; amides such as (meth) acrylamide; aryl acetate, aryl methyl ether And aryl derivatives such as arylphenyl ether; styrene derivatives such as styrene and ⁇ -methylstyrene; N-substituted maleimide compounds and the like.
- esters such as methyl (meth) acrylate, dimethyl fumarate, and dimethyl maleate
- amides such as (meth) acrylamide
- aryl derivatives such as arylphenyl ether
- styrene derivatives such as styrene and ⁇ -methylstyrene
- N-substituted maleimide compounds and the like Specific examples of the component (c
- esterified products of (meth) acrylic acid of alkyl alcohols such as t-butyl alcohol and lauryl alcohol; ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, 1,3-butylene glycol di ( (Meth) acrylate, tripropylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9- Di (meth) acrylic esters such as nonanediol di (meth) acrylate and polyethylene glycol di (meth) acrylate; trifunctional ethylenically unsaturated compounds such as trimethylolpropane tri (meth) acrylate; pentaerythritol Tetrafunctional ethylenically unsaturated compounds such as tra (meth)
- Component (c) can be used singly or in combination of two or more. Specifically, a mixture of 1,6-hexanediol diacrylate and 1,6-hexanediol dimethacrylate, 1, Preferred examples include a mixture of 6-hexanediol diacrylate and trimethylpropane triacrylate.
- blending a component (c) solvent resistance, image property, and physical strength can be improved.
- the amount of component (c) is preferably in the range of 1.0 to 30.0% by mass, more preferably 5.0 to 10.0% by mass. When the content is less than 1.0% by mass, the crosslink density is lowered and the physical strength is inferior.
- component (d) include benzoin derivatives that are known ⁇ -cleaving compounds, hydrogen abstraction-type benzophenone derivatives, and the like. More specifically, benzoin methyl ether, benzoin Preferred examples include ethyl ether, benzoin isopropyl ether, benzoin dimethyl ketal, benzophenone / dimethylethanolamine mixture, and thioxanthone / dimethylethanolamine mixture. In addition, what is generally known as a photopolymerization initiator can be used.
- initiators include aromatic ketones such as benzophenone; benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, ⁇ -methylol benzoin methyl ether, ⁇ -methoxybenzoin methyl ether, 2,2-diethoxy Benzoin ethers such as phenylacetophenone; substituted and unsubstituted polynuclear quinones; 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-methyl-1- [4- (Methylthio) phenyl] -morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-hydroxy-2-methyl-1-phenyl Propan-1-one, 2,4,6-tri Methylbenzoyldiphenylphosphine oxide, 1- [4- (2-
- the amount of component (d) is preferably in the range of 0.1 to 10.0% by mass, more preferably 1.0 to 3.0% by mass. When it is less than 0.1% by mass, the crosslinking density is lowered and the physical strength is lowered. When it exceeds 10.0% by mass, the image quality is inferior because of the large amount of light absorption in the effective active irradiation region.
- the photosensitive resin composition for flexographic printing of the present invention may optionally include a plasticizer, an ultraviolet absorber, a polymerization inhibitor, Dyes, inorganic fine particles, and the like can be added.
- hydrocarbon oils such as naphthene oil and paraffin oil, low molecular weight polystyrene having a molecular weight of 3,000 or less, petroleum resin, polyisoprene, poly (2,3-dimethyl-1,3-butadiene), poly (1,3 -Pentadiene), poly (2-methyl-1,3-pentadiene), poly (1,3-hexadiene), poly (4,5-diethyl-1,3-octadiene), poly (3-butyl-1,3 -Octadiene), 1,2-polybutadiene, 1,4-polybutadiene.
- the polypentadiene and the like are useful for adjusting the hardness of the printing plate and improving the workability during molding.
- the photosensitive resin plate material of the present invention comprises at least a support and the photosensitive resin composition of the present invention.
- a plastic plate, an aluminum plate, or the like can be used, and a polyethylene terephthalate film, a urethane film, a polyethylene film, a polypropylene film, or the like is preferable.
- a polyethylene terephthalate film is preferably used.
- FIG. 1 is a perspective view of the photosensitive resin plate material of the present invention having this three-layer structure
- FIG. 2 is a cross-sectional view taken along the line AA ′ of FIG. 1 and 2
- (1) is a photosensitive resin plate material of the present invention having a three-layer structure
- (2) is a support
- (3) is a photosensitive resin composition of the present invention
- (4) is A cover film is shown. This cover film is effective for improving plate-making workability, protecting the plate surface and preventing scratches.
- (3) is provided with a slip layer, a protective layer, or an ultraviolet shielding layer containing an infrared sensitive substance that can be ablated with an infrared laser between the photosensitive resin composition of the present invention and (4) a cover film.
- a slip layer a protective layer, or an ultraviolet shielding layer containing an infrared sensitive substance that can be ablated with an infrared laser between the photosensitive resin composition of the present invention and (4) a cover film.
- the thickness of the support is preferably 75 to 200 ⁇ m, more preferably 100 to 200 ⁇ m.
- the thickness of the photosensitive resin composition is preferably 0.5 to 10.0 mm, more preferably 1.0 to 9.0 mm.
- the thickness of the cover film is preferably 75 to 200 ⁇ m, more desirably 100 to 200 ⁇ m.
- the photosensitive resin composition for flexographic printing of the present invention containing at least the essential components (a) to (d) is preferably 90 to 150 ° C., preferably 110 to 140 ° C. for 40 to 90 minutes, preferably Can be produced by a method of kneading for 40 to 60 minutes and then extruding with a hot press.
- the photosensitive resin composition thus prepared was fed through a raw material inlet of an extrusion molding machine whose barrel temperature was maintained at 120 ° C. through a quantitative supply device maintained at 120 ° C.
- the photosensitive composition discharged from the base part is sandwiched between a cover film (PET film pre-coated with a polyamide resin 4 ⁇ m release agent) and a support (PET film pre-coated with a urethane adhesive), and a plate A gap between the two forming rolls was set in advance so as to match the thickness, and the sheet was formed into a sheet by passing through this gap. After cooling, the photosensitive resin plate material was obtained by cutting into a predetermined size.
- the photosensitive resin plate was back exposed for 25 seconds from the support side by JE-AO-SH (manufactured by JEOL Ltd .: exposure unit) equipped with 32 JL-40SPRC (manufactured by JEOL Ltd .: chemical lamp). . After that, the cover film is peeled off, the solid negative film is vacuum-adhered on the photosensitive resin layer, and exposed for 10 minutes from the negative film side with the same chemical lamp, and then JW-AO-SDR (manufactured by JEOL Ltd .: Rotary Type Lunasolve II (manufactured by JEOL Seiki Co., Ltd.) as a developer, and then dried again in an oven heated to 60 ° C. for 30 minutes.
- JEF-A0-S (GL) (JEOL Seiki Co., Ltd.) Surface treatment and post-exposure were simultaneously performed for 10 minutes by a company (surface treatment / post-exposure apparatus).
- a test piece was prepared by cutting the photosensitive resin plate treated under the above plate making conditions into 5.0 cm ⁇ 5.0 cm in length and width, and left in a beaker filled with ethyl acetate having a liquid temperature of 25.7 ° C. Until the elapse of time, the mass increase rate of the test piece was measured every hour, and the small mass increase rate was evaluated as being resistant to the solvent. Table 2 shows the weight increase rate of the test piece.
- Example 4 was a resin plate having the smallest mass increase rate and stable to the solvent as compared with Comparative Examples 1 to 3 and Examples 1 to 3.
- Examples 1 to 4 were used except that BAC-45 (manufactured by Osaka Organic Chemical Co., Ltd., terminal acrylic modified 1,4-polybutadiene) was used as the terminal acrylic-modified liquid polybutadiene in the proportions shown in Table 3. The solvent resistance was similarly evaluated. The results are shown in Table 4.
- BAC-45 manufactured by Osaka Organic Chemical Co., Ltd., terminal acrylic modified 1,4-polybutadiene
- Examples 5 and 6 and Comparative Examples 8 to 10 In the same manner as in Examples 1 to 4, a disk-shaped test piece having a diameter of 11 cm was prepared. The disc-shaped test piece is fixed to a test stand of a JEM abrasion tester, rotated, and the resin surface is worn by sliding a wheel with an outer diameter wound with abrasive paper on the upper surface of the test piece, and 2,000 rotations. The subsequent mass loss rate was measured.
- Example 5 and Example 6 except that BAC-45 (manufactured by Osaka Organic Chemical Co., Ltd., terminal acrylic modified 1,4-polybutadiene) was used as the terminal acrylic modified liquid polybutadiene.
- the wear test was conducted in the same manner as in Nos. 6 and 6. The results are shown in Table 5.
- the example using the terminal acrylic-modified 1,2-polybutadiene has a smaller mass reduction rate and the resistance to resistance than the comparative example using the terminal acrylic-modified 1,4-polybutadiene. It can be said that it is excellent in abrasion.
- the present invention is a flexographic printing that has resistance to ink containing organic solvents and emulsion ink, such as UV curable ink or vegetable oil or light naphtha, and has excellent image reproducibility and printing durability.
- the photosensitive resin composition for flexographic printing obtained by laminating the photosensitive resin composition for flexographic printing and the photosensitive resin composition for flexographic printing can be provided.
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Abstract
Description
本願は、2009年4月10日に出願された日本国特許出願特願2009-096180号に対し優先権を主張し、その内容をここに援用する。
上記の問題を克服すべく、このような感光性樹脂組成物の耐溶剤性に関し、いくつかの方法が提案されている。
すなわち本発明は以下の通りである。
(1)成分(a):熱可塑性エラストマー、成分(b):1,2-結合を80%以上含有する(メタ)アクリル変性液状ポリブタジエン、成分(c):1つ以上のエチレン性不飽和基を持つ光重合性不飽和単量体及び成分(d):光重合開始剤を含むことを特徴とするフレキソ印刷用感光性樹脂組成物、
(2)成分(a)を18.0~95.0質量%、成分(b)を1.0~80.0質量%、成分(c)を1.0~30.0質量%、及び成分(d)を0.1~10.0質量%の範囲で含有することを特徴とする上記(1)に記載のフレキソ印刷用感光性樹脂組成物、
(3)成分(b)が、ポリマー末端が(メタ)アクリル変性されている、1,2-結合を80%以上含有する液状ポリブタジエンであることを特徴とする上記(1)又は(2)に記載のフレキソ印刷用感光性樹脂組成物、
(4)成分(b)が、その数平均分子量が200~100,000であり、45℃での粘度が4Pa・s以上であることを特徴とする上記(1)~(3)のいずれかに記載のフレキソ印刷用感光性樹脂組成物、及び、
(5)上記(1)~(4)のいずれかに記載のフレキソ印刷用感光性樹脂組成物が支持体表面に積層されていることを特徴とするフレキソ印刷用感光性樹脂版材に関する。
2 支持体
3 感光性樹脂組成物
4 カバーフィルム
まず、本発明のフレキソ印刷用感光性樹脂組成物について説明する。
本発明のフレキソ印刷用感光性樹脂組成物は、以下に示す(a)~(d)を必須成分としてなる。
成分(a):1種類以上の熱可塑性エラストマー
成分(b):1,2-結合を80%以上含有する(メタ)アクリル変性液状ポリブタジエン
成分(c)少なくとも1つ以上のエチレン性不飽和基を持つ光重合性単量体
成分(d)光重合開始剤
本発明に係る(a)成分である熱可塑性エラストマーとして、具体的には、スチレン-イソプレン-スチレン共重合体(以下SISという場合がある)、スチレン-ブタジエン-スチレン共重合体(以下SBSという場合がある)又はスチレン-イソプレン-ブタジエン-スチレン共重合体(以下SIBSという場合がある)、スチレン-エチレン-ブチレン-スチレン共重合体(以下SEBSという場合がある)、スチレン-エチレン-プロピレン-スチレン共重合体(以下SEPSという場合がある)、シンジオタクティック1,2-ポリブタジエン(以下RBということがある)等を例示することができる。
本発明において用いられる前記RBは、低結晶性のエラストマーで反応性に冨み、1,2結合量は85%以上で、結晶化度は10~50%の範囲であることが望ましい。結晶化度が高くなると硬くなり、ゴム弾性がなくなり結晶化度が低くなると物理的物性が低下する。
本発明に係る成分(b)は、1,2-結合を80%以上含有する液状ポリブタジエン分子に、1以上のメタアクリロイル基あるいはアクリロイル基を導入した構造を持つ液状ポリマーであり、特に、ポリマー分子末端に前記官能基を導入した構造が好ましい。具体的には、下記、1,2-結合による繰り返し単位(1)及び1,4-結合による繰り返し単位(2)
成分(b)はその分子構造中に少なくとも1つ以上のエチレン性不飽和基を持つため、過酸化物、光重合開始剤による熱重合あるいは光重合が可能である。また、必須成分(a)、(c)、及び(d)との相溶性は非常に良好である。
製造法としては、例えば、水酸基含有ポリブタジエンの水酸基に、(メタ)アクリル基を有する化合物を反応させて(メタ)アクリル基を導入することができる。
(メタ)アクリル基を有する化合物としては、アクリル酸、メタクリル酸等の(メタ)アクリル酸類、アクリル酸メチル、メタクリル酸メチル、アクリル酸エチル、メタクリル酸エチル等の(メタ)アクリル酸エステル類等を例示する事ができる。
また、(メタ)アクリル基を導入する方法は、p-トルエンスルフォン酸等を触媒として、(メタ)アクリル酸類とポリブタジエンの水酸基とを脱水縮合する方法、チタン触媒、スズ触媒等を触媒として、(メタ)アクリル酸エステル類とポリブタジエンの水酸基とでエステル交換にて導入する方法、イソシアネート基を2以上有する化合物と(メタ)アクリル酸2-ヒドロキシエチルエステル等の水酸基含有(メタ)アクリル酸エステル類とポリブタジエンの水酸基とを反応させる方法等が知られている。
本発明に係る成分(c)としては、具体的には、(メタ)アクリル酸メチル、フマル酸ジメチル、マレイン酸ジメチル等のエステル類;(メタ)アクリルアミド等のアミド類;アリールアセテート、アリールメチルエーテル、アリールフェニルエーテル等のアリール誘導体;スチレン、α-メチルスチレン等のスチレン誘導体;N置換マレイミド化合物等をあげることができる。さらに具体的に、t-ブチルアルコール、ラウリルアルコール等のアルキルアルコールの(メタ)アクリル酸のエステル化物類;エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、1,3-ブチレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、1,4-ブタンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,6-ヘキサンジオールジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート等のジ(メタ)アクリル酸エステル類;トリメチロールプロパントリ(メタ)アクリレート等の三官能エチレン性不飽和化合物;ペンタエリスリトールテトラ(メタ)アクリレート等の四官能エチレン性不飽和化合物;ジアセトンアクリルアミド、(メタ)アクリルアミド等のアミド誘導体;スチレン、ビニルトルエン、ジビニルベンゼン等のスチレン誘導体;ジアリルフタレート、トリアリルシアヌレート等のアリルエステル類;フマル酸ジエチルエステル、フマル酸ジブチルエステル、フマル酸ジオクチルエステル、フマル酸ジステアリルエステル、フマル酸ブチルオクチルエステル、フマル酸ジフェニルエステル、フマル酸ジベンジルエステル、マレイン酸ジブチルエステル、マレイン酸ジオクチルエステル、フマル酸ビス(3-フェニルプロピル)エステル、フマル酸ジラウリルエステル、フマル酸ジベヘニルエステル等のフマル酸又はマレイン酸エステル類;N-n-ヘキシルマレイミド、N-シクロヘキシルマレイミド、N-n-オクチルマレイミド、N-2-エチルヘキシルマレイミド、N-n-デシルマレイミド、N-n-ラウリルマレイミド等のN置換マレイミド類等を好ましく例示することができる。
成分(d)として、具体的には、公知のα解裂をする化合物であるベンゾイン誘導体、または水素引抜きタイプのベンゾフェノン誘導体等を例示することができ、さらに具体的には、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインジメチルケタール、ベンゾフェノン・ジメチルエタノールアミン混合物、チオキサントン・ジメチルエタノールアミン混合物等を好ましく例示することができる。他にも一般的に光重合開始剤として知られているものを用いることができる。このような開始剤の一例として、ベンゾフェノンのような芳香族ケトン類;ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、α-メチロールベンゾインメチルエーテル、α-メトキシベンゾインメチルエーテル、2,2-ジエトキシフェニルアセトフェノン等のベンゾインエーテル類;置換及び非置換の多核キノン類;1-ヒドロキシシクロヘキシルフェニルケトン、2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン、2-メチル-1-[4-(メチルチオ)フェニル]-モルフォリノプロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタン-1-オン、2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン、2,4,6-トリメチルベンゾイルジフェニルホスフィンオキシド、1-〔4-(2-ヒドロキシエトキシ)フェニル〕-2-ヒドロキシ-2-メチル-1-プロパン-1-オン、2,4-ジエチルチオキサントン、2-クロロチオキサントン、2,4-ジメチルチオキサントン、3,3-ジメチル-4-メトキシベンゾフェノン、ベンゾフェノン、1-クロロ-4-プロポキシチオキサントン、1-(4-イソプロピルフェニル)-2-ヒドロキシ-2-メチルプロパン-1-オン、1-(4-ドデシルフェニル)-2-ヒドロキシ-2-メチルプロパン-1-オン、4-ベンゾイル-4’-メチルジメチルスルフィド、4-ジメチルアミノ安息香酸、4-ジメチルアミノ安息香酸メチル、4-ジメチルアミノ安息香酸エチル、4-ジメチルアミノ安息香酸ブチル、4-ジメチルアミノ安息香酸-2-エチルヘキシル、4-ジメチルアミノ安息香酸-2-イソアミル、2,2’-ジエトキシアセトフェノン、ベンジルジメチルケタール、ベンジル-β-メトキシエチルアセタール、o-ベンゾイル安息香酸メチル、ビス(4-ジメチルアミノフェニル)ケトン、4,4’-ビスジエチルアミノベンゾフェノン、4,4’-ジクロロベンゾフェノン、ベンジル、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾイン-n-ブチルエーテル、ベンゾインイソブチルエーテル、p-ジメチルアミノアセトフェノン、p-tert-ブチルトリクロロアセトフェノン、p-tert-ブチルジクロロアセトフェノン、2-(o-クロロフェニル)-4,5-ジフェニルイミダゾリル二量体、チオキサントン、2-メチルチオキサントン、2-イソプロピルチオキサントン、ジベンゾスベロン、α,α-ジクロロ-4-フェノキシアセトフェノン、ペンチル-4-ジメチルアミノベンゾエート、9-フェニルアクリジン、1,7-ビス-(9-アクリジニル)へプタン、1,5-ビス-(9-アクリジニル)ペンタン、1,3-ビス-(9-アクリジニル)プロパン等を例示することができる。
本発明のフレキソ印刷用感光性樹脂組成物には、前述の(a)~(d)の必須成分に加えて、任意に可塑剤、紫外線吸収剤、重合防止剤、色素、無機性微粒子などが添加できる。例えば、ナフテン油やパラフィン油のような炭化水素油、分子量3,000以下の低分子ポリスチレン、石油樹脂、ポリイソプレン、ポリ(2,3-ジメチル-1,3-ブタジエン)、ポリ(1,3-ペンタジエン)、ポリ(2-メチル-1,3-ペンタジエン)、ポリ(1,3-ヘキサジエン)、ポリ(4,5-ジエチル-1,3-オクタジエン)、ポリ(3-ブチル-1,3-オクタジエン)、1,2-ポリブタジエン、1,4-ポリブタジエンが挙げられる。前記ポリペンタジエン等は刷版の硬度調整、成形時の加工性を向上させるのに有用である。
次に、本発明のフレキソ印刷用感光性樹脂版材について説明する。
本発明の感光性樹脂版材は、少なくとも支持体と本発明の感光性樹脂組成物からなる。
少なくとも(a)~(d)の必須成分を含有する本発明のフレキソ印刷用感光性樹脂組成物を、90~150℃、好ましくは110~140℃の温度条件下で、40~90分間、好ましくは40~60分間混練した後、加熱プレスで押し出し成形加工する方法によって版材を製造することができる。
〔実施例1~4及び比較例1~3〕
(感光性樹脂版材の製造)
熱可塑性エラストマーSBS [Kraton社製、クレイトンD-KX405CP]65質量部、以下表1の組成からなる可塑剤25質量部、アクリルモノマーとして1,6-ヘキサンジオールジアクリレート5.5質量部、1,6-ヘキサンジオールジメタクリレート0.5質量部、及び光重合開始剤として2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン1.5質量部をニーダーに入れて温度110~140℃で、60分間混練する。このようにして調製した感光性樹脂組成物を、120℃に保たれた定量供給装置を通じて、バレル温度が120℃に保たれた押し出し成形機の原料投入口より投入した。口金部から排出される感光性組成物をカバーフィルム(予めポリアミド系樹脂4μm離型剤を塗工したPETフイルム)と、支持体(予めウレタン系接着剤を塗工したPETフイルム)で挟み、版厚に合うように予め成形用二本ロールの間隙を設定し、この間隙を通過させることにより、シート状に成形した。冷却後、所定のサイズに切断することにより、感光性樹脂版材を得た。
※末端アクリル変性液状1,2-ポリブタジエン:日本曹達社製、NISSO PB EA-3000(粘度12Pa・S(45℃)、数平均分子量4,600(GPC法)、M(1)/〔M(1)+M(2)〕=0.86)
※石油系炭化水素:日本サン石油社製、SUNPURE N-90
※流動パラフィン:(株)MORESCO製、モレスコホワイト(登録商標) P-70
感光性樹脂版を支持体側から、JL-40SPRC(日本電子精機株式会社製:ケミカル灯)を32本設置したJE-AO-SH(日本電子精機株式会社製:露光ユニット)により25秒間裏露光した。その後、カバーフィルムを剥がし、感光性樹脂層上に、ベタネガフィルムを真空密着させ、同じケミカル灯でネガフィルム側から10分間露光した後、JW-AO-SDR(日本電子精機株式会社製:ロータリー型洗浄機)を用いてルナソルブII(日本電子精機株式会社製)を現像液として洗浄し、改めて60℃に加熱したオーブンで30分間乾燥し、JEF-A0-S(GL)(日本電子精機株式会社:表面処理・後露光装置)により,表面処理と後露光を同時に10分間行った。
次に上記製版条件で処理した感光性樹脂版を縦横5.0cm×5.0cmにカットした試験片を作成し、液温25.7℃の酢酸エチルで満たしたビーカー中に静置し、5時間経過まで、1時間毎に試験片の質量増加率を測定し、その質量増加率が小さいものが溶剤に対して耐性があると評価した。表2に試験片の重量増加率を示した。
実施例1~4において、末端アクリル変性液状ポリブタジエンとして、BAC-45(大阪有機化学(株)製、末端アクリル変性1,4-ポリブタジエン)を表3に示す割合で用いる以外、実施例1~4と同様に行い、同様に耐溶剤性を評価した。その結果を表4に示す。
実施例1~4と同様にして、直径11cmの円盤状の試験片を作成した。円盤状試験片をJEM製摩耗試験機の試験台に固定し、回転させ、試験片の上面に、外径に研磨紙を巻いた車輪を摺動させることにより、樹脂表面を摩耗し、2000回転後の質量減少率を測定した。比較例8~10については、実施例5及び6において、末端アクリル変性液状ポリブタジエンとして、BAC-45(大阪有機化学(株)製、末端アクリル変性1,4-ポリブタジエン)を用いる以外、実施例5及び6と同様に磨耗試験を行った。その結果を表5に示す。
Claims (5)
- 成分(a):熱可塑性エラストマー、
成分(b):1,2-結合を80%以上含有する(メタ)アクリル変性液状ポリブタジエン、
成分(c):1つ以上のエチレン性不飽和基を持つ光重合性不飽和単量体及び
成分(d):光重合開始剤
を含むことを特徴とするフレキソ印刷用感光性樹脂組成物。 - 成分(a)を18.0~95.0質量%、成分(b)を1.0~80.0質量%、成分(c)を1.0~30.0質量%、及び成分(d)を0.1~10.0質量%の範囲で含有することを特徴とする請求項1に記載のフレキソ印刷用感光性樹脂組成物。
- 成分(b)が、ポリマー末端が(メタ)アクリル変性されている、1,2-結合を80%以上含有する液状ポリブタジエンであることを特徴とする請求項1又は2に記載のフレキソ印刷用感光性樹脂組成物。
- 成分(b)が、その数平均分子量が200~100,000であり、45℃での粘度が4Pa・s以上であることを特徴とする請求項1~3のいずれかに記載のフレキソ印刷用感光性樹脂組成物。
- 請求項1~4のいずれかに記載のフレキソ印刷用感光性樹脂組成物が支持体表面に積層されていることを特徴とするフレキソ印刷用感光性樹脂版材。
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WO2011045918A1 (ja) * | 2009-10-14 | 2011-04-21 | 日本曹達株式会社 | ポリブタジエンの製造方法 |
CN102540715A (zh) * | 2010-12-30 | 2012-07-04 | 乐凯华光印刷科技有限公司 | 一种容易去粘的柔性感光树脂版 |
JP2015105955A (ja) * | 2013-11-28 | 2015-06-08 | 株式会社クラレ | 感光性樹脂組成物 |
JP2018116110A (ja) * | 2017-01-17 | 2018-07-26 | 旭化成株式会社 | 印刷版用感光性樹脂版の製造方法 |
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