CN111856876A - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- CN111856876A CN111856876A CN201910337783.5A CN201910337783A CN111856876A CN 111856876 A CN111856876 A CN 111856876A CN 201910337783 A CN201910337783 A CN 201910337783A CN 111856876 A CN111856876 A CN 111856876A
- Authority
- CN
- China
- Prior art keywords
- polyvinyl alcohol
- compound
- acrylamide
- resin composition
- photosensitive resin
- 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
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- 239000011342 resin composition Substances 0.000 title claims abstract description 32
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 75
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 33
- 229920005989 resin Polymers 0.000 claims abstract description 33
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 44
- -1 acrylamide compound Chemical class 0.000 claims description 26
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 239000007864 aqueous solution Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 238000010526 radical polymerization reaction Methods 0.000 claims description 8
- 238000006136 alcoholysis reaction Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000003957 anion exchange resin Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000005342 ion exchange Methods 0.000 claims description 6
- 150000003926 acrylamides Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000011265 semifinished product Substances 0.000 claims description 5
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003211 polymerization photoinitiator Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007639 printing Methods 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 238000007650 screen-printing Methods 0.000 description 11
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 3
- 230000002572 peristaltic effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- ZYMCJDAUBJFVSM-UHFFFAOYSA-N 6-methylheptyl 4-(dimethylamino)benzoate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 ZYMCJDAUBJFVSM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 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 2
- 239000003292 glue Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- CPQUDUZKHJNUHS-UHFFFAOYSA-N 1-[2-(cyclopenten-1-yloxy)ethoxy]cyclopentene Chemical compound C=1CCCC=1OCCOC1=CCCC1 CPQUDUZKHJNUHS-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- SBVKVAIECGDBTC-UHFFFAOYSA-N 4-hydroxy-2-methylidenebutanamide Chemical compound NC(=O)C(=C)CCO SBVKVAIECGDBTC-UHFFFAOYSA-N 0.000 description 1
- AECUZIRJHGATLE-UHFFFAOYSA-N CO.CO.CO.CCC Chemical compound CO.CO.CO.CCC AECUZIRJHGATLE-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- TZWFNVVLIGAFTB-UHFFFAOYSA-N N-[(2-hydroxy-5-methylsulfanylphenyl)methyl]prop-2-enamide Chemical compound C(C=C)(=O)NCC1=C(C=CC(=C1)SC)O TZWFNVVLIGAFTB-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 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
- 239000003112 inhibitor Substances 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- POVITWJTUUJBNK-UHFFFAOYSA-N n-(4-hydroxyphenyl)prop-2-enamide Chemical compound OC1=CC=C(NC(=O)C=C)C=C1 POVITWJTUUJBNK-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention discloses a photosensitive resin composition, which comprises the following components: the weight ratio of the acrylamide modified polyvinyl alcohol resin liquid to the compound with an ethylenic unsaturated group to the photocrosslinking agent is that: compound having an ethylenically unsaturated group: photocrosslinkers are 1: 0.15-1.2: 0.01-0.5. the photosensitive resin composition provided by the invention has the advantages of high exposure speed, simple operation, long storage time, good resolution and bridging property and high printing resistance, and can be used in the thick film plate making field and meet the plate making requirement of common film thickness.
Description
Technical Field
The invention relates to the field of photosensitive resin compositions, in particular to a platemaking photosensitive resin composition for screen printing.
Background
In a short few decades, the quality of plate-making photosensitive resin compositions for screen printing has been greatly improved with the market demand and the development of industry. The earliest dichromate photosensitive system is prepared by ammonium dichromate/potassium + polyvinyl alcohol into glue solution, non-image-text photocuring part is crosslinked into a film after exposure, the non-image-text photocuring part is dissolved in water, and a silk screen printing plate with images and texts is formed after water washing and developing, and the photocuring crosslinked ink layer has low strength, poor printing resistance and great pollution; the diazo photosensitive system of the seventies is prepared by diazo salt, polyvinyl alcohol and polyvinyl acetate emulsion, the screen plate prepared by the photosensitive system has certain tolerance, but has certain bottleneck on resolution and high sensitivity, in order to further improve the tolerance and the resolution, the diazo photosensitive resin composition is added with photo-initiated free radical polymer and optical bridging agent to form binary curing, and as the diazo photosensitive resin composition can form a matrix pre-sensitization effect on a silk screen, the resolution, the bridging and the printing resistance of the manufactured screen plate and the screen plate regeneration are all obviously improved; however, the diazo photosensitive resin composition needs to be added with a photocrosslinking agent such as diazo resin before use, and the prepared colloid has a viscosity change easily caused by more than one week of storage time, and particularly, the phenomenon of gelation can occur within several days in summer; meanwhile, the scrapping of the manufactured screen printing plate is easily caused by artificial glue mixing and water pollution, the light sensitivity is insufficient, the exposure time is too long when the thick film screen printing plate is manufactured, and the exposure working efficiency is low. In order to improve sensitivity and storage stability, a one-pack type photosensitive resin composition containing Styrylpyridinyl (SBQ) has been gradually marketed and developed in the field of thick film plate-making, but the number of styrylpyridinyl groups that can be added to the system is limited, and the bridge density after exposure cannot be sufficiently increased, and therefore it is difficult to obtain a screen plate having good water resistance.
The traditional photosensitive resin composition is exposed and cured by a high-pressure mercury lamp or a metal halogen lamp, but the energy conversion efficiency and the service life of the traditional photosensitive resin composition are limited, the traditional photosensitive resin composition is gradually replaced by an LED and is increasingly popularized, meanwhile, a screen printing plate manufactured by film exposure is adopted, the micronization of the screen printing plate is limited due to the limitation of the precision of the film, the screen printing plate manufacturing technology of laser scanning exposure by a direct plate making machine through CAD data is rapidly developed, the requirements of micronization and high precision of the electronic industry can be met, and further higher requirements are provided for the performance of the plate-making photosensitive resin composition for screen printing.
Disclosure of Invention
The purpose of the invention is as follows: in order to overcome the above-mentioned drawbacks of the prior art, there is provided a one-pack type photosensitive resin composition having high sensitivity and high performance, which can be applied to conventional exposure equipment and direct plate-making machines.
The technical scheme is as follows: a photosensitive resin composition comprising the following components: the weight ratio of the acrylamide modified polyvinyl alcohol resin liquid to the compound with an ethylenic unsaturated group to the photocrosslinking agent is that: compound having an ethylenically unsaturated group: photocrosslinkers are 1: 0.15-1.2: 0.01 to 0.5.
In a preferred embodiment of the present invention, the weight ratio of the acrylamide-modified polyvinyl alcohol resin solution, the compound having an ethylenically unsaturated group, and the photocrosslinking agent is: compound having an ethylenically unsaturated group: photocrosslinkers are 1: 0.5-1.0: 0.03 to 0.1.
In a preferred embodiment of the present invention, the method for preparing the acrylamide-modified polyvinyl alcohol resin solution comprises the steps of:
(1) dissolving the measured polyvinyl alcohol compound in pure water to prepare polyvinyl alcohol compound aqueous solution with 20% of solid content, and completely dissolving the measured acrylamide compound in the pure water to prepare acrylamide compound aqueous solution;
(2) adding metered phosphoric acid with the content of 85% into a polyvinyl alcohol compound aqueous solution, heating to 40-80 ℃ under stirring, keeping the temperature constant, dropwise adding an acrylamide compound aqueous solution at a constant speed for 2-6h, and continuously stirring to react for 4-20h after dropwise adding is finished to obtain a semi-finished product reaction solution;
(3) and stirring the semi-finished reaction solution and anion exchange resin at room temperature for ion exchange, and filtering by adopting a 150-mesh silk screen until the pH of the reaction solution is 5-6 to obtain the acrylamide modified polyvinyl alcohol resin solution.
In a preferred embodiment of the present invention, the polyvinyl alcohol compound in the synthesis of the acrylamide modified polyvinyl alcohol resin solution is one or more polyvinyl alcohol free mixtures of polyvinyl alcohol and modified polyvinyl alcohol containing anions or cations, wherein the alcoholysis degree is 70-99 mol%, and the polymerization degree is 500-3000.
In a preferred embodiment of the present invention, the acrylamide compound used in the synthesis of the acrylamide-modified polyvinyl alcohol resin solution is an acrylamide compound having a hydroxyl functional group.
In a preferred embodiment of the present invention, the molar ratio of the polyvinyl alcohol compound to the acrylamide compound in the synthesis of the acrylamide-modified polyvinyl alcohol resin solution is 2-12: 1, and the amount of phosphoric acid is 1-5% of the total amount of the polyvinyl alcohol compound and the acrylamide compound.
In a preferred embodiment of the present invention, the molar ratio of the polyvinyl alcohol compound to the acrylamide compound in the synthesis of the acrylamide-modified polyvinyl alcohol resin solution is 4-8: 1, and the amount of phosphoric acid is 2-4% of the total amount of the polyvinyl alcohol compound and the acrylamide compound.
In a preferred embodiment of the present invention, the compound having an ethylenically unsaturated group is a compound having at least one ethylenically unsaturated group, the ethylenically unsaturated group compound includes a radically polymerizable monomer or oligomer, and the radically polymerizable monomer includes a monofunctional monomer or a polyfunctional monomer.
As a preferred mode of the present invention, the photocrosslinker includes a water-soluble photocrosslinker comprising one or more of a diazo resin, a dichromate, or a diazide compound, and/or a radical polymerization photoinitiator.
The invention realizes the following beneficial effects:
the photosensitive resin composition provided by the invention is of a single-liquid type, has the advantages of high exposure speed, simple and convenient operation, long storage time, good resolution ratio and bridging property and high printing resistance, and can be used in the field of thick film plate making and also meet the plate making requirement of common film thickness.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments.
A photosensitive resin composition comprising the following components: the weight ratio of the acrylamide modified polyvinyl alcohol resin liquid to the compound with an ethylenic unsaturated group to the photocrosslinking agent is that: compound having an ethylenically unsaturated group: photocrosslinkers are 1: 0.15-1.2: 0.01 to 0.5, preferably 1: 0.5-1.0: 0.03 to 0.1.
The preparation method of the acrylamide modified polyvinyl alcohol resin liquid comprises the following steps:
(1) dissolving the measured polyvinyl alcohol compound in pure water to prepare polyvinyl alcohol compound aqueous solution with 20% of solid content, and completely dissolving the measured acrylamide compound in the pure water to prepare acrylamide compound aqueous solution;
(2) adding metered phosphoric acid with the content of 85% into a polyvinyl alcohol compound aqueous solution, heating to 40-80 ℃ under stirring, keeping the temperature constant, dropwise adding an acrylamide compound aqueous solution at a constant speed for 2-6h, and continuously stirring to react for 4-20h after dropwise adding is finished to obtain a semi-finished product reaction solution;
(3) and stirring the semi-finished reaction solution and anion exchange resin at room temperature for ion exchange, and filtering by adopting a 150-mesh silk screen until the pH of the reaction solution is 5-6 to obtain the acrylamide modified polyvinyl alcohol resin solution.
The polyvinyl alcohol compound is polyvinyl alcohol or partially alcoholyzed polyvinyl alcohol, or the polyvinyl alcohol and the partially alcoholyzed polyvinyl alcohol can be mixed for use, or the polyvinyl alcohol modified by anions or cations and partially alcoholyzed polyvinyl alcohol can be used, wherein the alcoholysis degree is 70-99 mol%, the polymerization degree is 500-3000, the low polymerization degree can slow down the photocuring speed to cause insufficient sensitivity, and the high polymerization degree can cause the high viscosity of the system to be incapable of use.
The acrylamide compound is an acrylamide compound containing a hydroxyl functional group.
Specific examples are as follows: one or more of N-methylol acrylamide, N-hydroxyethyl acrylamide, N-p-hydroxyphenyl acrylamide, N- (2-hydroxy-5-methylthiobenzyl) acrylamide and the like.
The molar ratio of polyvinyl alcohol compounds (calculated by monomers) to acrylamide compounds in the synthesis of acrylamide modified polyvinyl alcohol resin liquid is 2-12: 1, preferably 4-8: 1; the amount of the phosphoric acid is 1-5%, preferably 2-4% of the total amount of the polyvinyl alcohol compound and the acrylamide compound.
Compound having an ethylenically unsaturated group:
the compound with the ethylenic unsaturated group is a compound containing at least more than one ethylenic unsaturated group and comprises a free radical polymerization monomer or oligomer, and the free radical polymerization monomer comprises a monofunctional monomer or a multifunctional monomer.
Monofunctional monomers include 2-ethylhexyl (meth) acrylate, 2-isodecyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2 (2-ethoxyethoxy) ethyl- (meth) acrylate, 2-phenoxyethyl methacrylate, ethyl 2- (2-methoxyethoxy) methacrylate, hydrogen furfuryl (meth) acrylate, ethylene glycol dicyclopentenyl ether methacrylate, 3-chloro-2-hydroxy propyl methacrylate, triallyl isocyanurate.
The polyfunctional monomer includes one or more of trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, tripropylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, ethoxylated bisphenol a di (meth) acrylate, and propane trimethanol tri (meth) acrylate.
The oligomers include: one or more of polyester (meth) acrylate oligomer, bisphenol a epoxy resin (meth) acrylate oligomer, caprolactone-acrylate copolymer, novolac epoxy resin (meth) acrylate oligomer, cresol novolac epoxy resin (meth) acrylate oligomer, and urethane (meth) acrylate copolymer.
Photocrosslinkers
The photocrosslinking agent comprises a water-soluble photocrosslinking agent and/or a radical polymerization photoinitiator, and the water-soluble photocrosslinking agent comprises one or more of diazo resin, dichromate or diazido compound.
The water-soluble diazo resin is a water-soluble compound formed by condensing water-soluble salt of 4-diazo diphenylamine and/or water-soluble salt of 4-diazo-3-methoxyl with paraformaldehyde in a sulfuric acid and/or phosphoric acid medium.
The radical polymerization photoinitiator is not limited to a specific one, and at least one of the known photoinitiators may be used in combination.
Specific examples are as follows: isopropyl thioxanthone, isooctyl p-dimethylaminobenzoate, 2-hydroxy-methylphenylpropane-1-one, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, methyl benzoylformate, benzoin dimethyl ether, benzophenone, 4-phenylbenzophenone, 4-chlorobenzophenone, methyl benzoylbenzoate, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2, 4-dimethylthioxanthone, and the like.
Other additives
The photosensitive resin composition for screen printing of the present invention may further contain additives such as a colorant, an antifoaming agent, a leveling agent, a preservative, a plasticizer, an ultraviolet absorber, a polymerization inhibitor, a solvent, and organic or inorganic fine powder, as required.
The technical solution of the present invention will be further specifically described below by way of specific examples.
Example 1 acrylamide-modified polyvinyl alcohol resin solution:
Completely dissolving 40g of polyvinyl alcohol (with the polymerization degree of 1700 and the alcoholysis degree of 87-89 mol%) in 160g of pure water to prepare a polyvinyl alcohol aqueous solution with the solid content of 20%, and completely dissolving 14g N-hydroxymethyl acrylamide in 50g of pure water to prepare an N-hydroxymethyl acrylamide aqueous solution; adding 1g of phosphoric acid with the content of 85% into the polyvinyl alcohol aqueous solution, heating to 60 ℃ under stirring, keeping the temperature constant, dropwise adding the N-hydroxymethyl acrylamide aqueous solution into the reactant at a constant speed by using a peristaltic pump for 6 hours, and continuously stirring and reacting for 20 hours after dropwise adding to obtain a semi-finished product reaction solution; (3) and stirring the semi-finished reaction solution and anion exchange resin at room temperature for ion exchange, and filtering by adopting a 150-mesh screen after the pH of the reaction solution is 5-6 to obtain the acrylamide modified polyvinyl alcohol resin solution.
Example 2 acrylamide-modified polyvinyl alcohol resin solution:
completely dissolving 40g of polyvinyl alcohol (degree of polymerization 2000, degree of alcoholysis 87-89 mol%) in 160g of pure water to prepare a polyvinyl alcohol aqueous solution with 20% of solid content, and completely dissolving 10.5g N-hydroxymethyl acrylamide in 50g of pure water to prepare an N-hydroxymethyl acrylamide aqueous solution; adding 1g of phosphoric acid with the content of 85% into the polyvinyl alcohol aqueous solution, heating to 60 ℃ under stirring, keeping the temperature constant, dropwise adding the N-hydroxymethyl acrylamide aqueous solution into the reactant at a constant speed by using a peristaltic pump for 2 hours, and continuously stirring to react for 10 hours after the dropwise addition is finished to obtain a semi-finished product reaction solution; (3) and stirring the semi-finished reaction solution and anion exchange resin at room temperature for ion exchange, and filtering by adopting a 150-mesh screen after the pH of the reaction solution is 5-6 to obtain the acrylamide modified polyvinyl alcohol resin solution.
Example 3 acrylamide-modified polyvinyl alcohol resin solution:
completely dissolving 40g of polyvinyl alcohol (with the polymerization degree of 1700 and the alcoholysis degree of 87-89 mol%) in 160g of pure water to prepare a polyvinyl alcohol aqueous solution with the solid content of 20%, and completely dissolving 16g of N-hydroxyethyl acrylamide in 50g of pure water to prepare an N-hydroxyethyl acrylamide aqueous solution; adding 1g of phosphoric acid with the content of 85% into the polyvinyl alcohol aqueous solution, heating to 60 ℃ under stirring, keeping the temperature constant, dropwise adding the hydroxyethyl acrylamide aqueous solution into the reactant at a constant speed by using a peristaltic pump for 6 hours, and continuously stirring and reacting for 20 hours after dropwise adding to obtain a semi-finished reaction solution; (3) and stirring the semi-finished reaction solution and anion exchange resin at room temperature for ion exchange, and filtering by adopting a 150-mesh screen after the pH of the reaction solution is 5-6 to obtain the acrylamide modified polyvinyl alcohol resin solution.
The photosensitive resin compositions (examples 4 to 11, comparative example 1 and comparative example 2) were obtained by mixing and dispersing the components in the proportions shown in Table-1 with a stirrer
The evaluation method comprises the following steps:
1. plate-making test (Metal halogen lamp exposure)
The photosensitive resin compositions of examples 4 to 11, comparative examples 1 and 2 were filtered through a 250-mesh polyester screen, and then repeatedly coated and dried on an aluminum screen frame plate having a 250-mesh yellow polyester screen by using a stainless steel spatula to prepare a photosensitive film having a surface film thickness of 10 μm. And then, tightly adhering the Autotype exposure computer film test piece to the layer surface of the photosensitive film, exposing for 2min at a distance of 1m by using a 3KW metal halogen lamp, and developing with water after exposure. The screen image was observed, and the results are shown in table 1.
Circa indicates that the image is extremely good; o indicates good image; Δ represents a usable range; the gamma representation is not usable.
2. Plate-making test (digital direct plate-making)
The photosensitive resin compositions of examples 4 to 11, comparative examples 1 and 2 were filtered through a 250-mesh polyester screen, and then repeatedly coated and dried on an aluminum screen frame plate having a 250-mesh yellow polyester screen by using a stainless steel spatula to prepare a photosensitive film having a surface film thickness of 10 μm. The plate was made by direct laser using a Mitsubishi CTS-1200 direct digital plate-making machine (semiconductor laser 12W, wavelength: 405 nm). The screen image was observed, and the results are shown in table 1.
3. Water resistance and solvent resistance friction performance test:
the screens prepared in examples 4-11 by exposure to a metal halogen lamp and digital direct plate making (after exposure, development, and complete drying) were tested for water and solvent rub resistance.
Water-resistant friction medium: pure water
Solvent resistant tribomedia: toluene: cyclohexanone: butanone: ethyl acetate 7:1:1:1 (mass ratio)
The two solvents were applied to a rubbing tester under 500g force, and rubbed on the screen 200 times with a dust-free cloth, and the changes in the screen were observed and the test results are shown in table 1.
Circlein indicates no fading due to friction and no obvious change of the screen printing plate; o indicates slight fading by rubbing and slight whitening of the screen; delta represents rubbing color loss, and the layout is whitish; the gamma ray expresses the friction fading, and the printing surface leaks the silk screen.
TABLE 1
Polyvinyl alcohol resin solution: polyvinyl alcohol (polymer 1700, alcoholysis degree 87-89 mol%) water solution with solid content of 15%
Chemical compound of ethylenic unsaturated group (A)
A-1: pentaerythritol triacrylate
A-2: ethoxylated bisphenol A diacrylate
A-3: tri (propane) Tri (meth) acrylate
Photocrosslinkers (B)
B-1: isopropyl thioxanthone: iso-octyl p-dimethylaminobenzoate 2:1 (weight ratio)
B-2: 2-hydroxy-methylphenylpropane-1-one: 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide ═ 1:1 (weight ratio)
B-3: paraformaldehyde and diphenylamine-4-diazonium salt condensate
Pigment: shanghai color raw 8301 blue color paste
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and are intended to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the scope of the present invention. All changes and modifications that come within the spirit of the invention are desired to be protected.
Claims (9)
1. A photosensitive resin composition, characterized in that the composition comprises the following components: the weight ratio of the acrylamide modified polyvinyl alcohol resin liquid to the compound with an ethylenic unsaturated group to the photocrosslinking agent is that: compound having an ethylenically unsaturated group: photocrosslinkers are 1: 0.15-1.2: 0.01 to 0.5.
2. The photosensitive resin composition according to claim 1, wherein the weight ratio of the acrylamide-modified polyvinyl alcohol resin solution, the compound having an ethylenically unsaturated group, and the photocrosslinking agent is: compound having an ethylenically unsaturated group: photocrosslinkers are 1: 0.5-1.0: 0.03 to 0.1.
3. The photosensitive resin composition according to claim 1, wherein the preparation method of the acrylamide modified polyvinyl alcohol resin solution comprises the following steps:
(1) dissolving the measured polyvinyl alcohol compound in pure water to prepare polyvinyl alcohol compound aqueous solution with 20% of solid content, and completely dissolving the measured acrylamide compound in the pure water to prepare acrylamide compound aqueous solution;
(2) Adding metered phosphoric acid with the content of 85% into a polyvinyl alcohol compound aqueous solution, heating to 40-80 ℃ under stirring, keeping constant temperature, dropwise adding an acrylamide compound aqueous solution at a constant speed for 2-6h, and continuously stirring to react for 4-20h after dropwise adding is finished to obtain a semi-finished product reaction solution;
(3) and stirring the semi-finished reaction solution and anion exchange resin at room temperature for ion exchange, and filtering by adopting a 150-mesh silk screen until the pH of the reaction solution is 5-6 to obtain the acrylamide modified polyvinyl alcohol resin solution.
4. The photosensitive resin composition according to claim 3, wherein: the polyvinyl alcohol compound in the synthesis of the acrylamide modified polyvinyl alcohol resin solution is one or more than one polyvinyl alcohol free mixture of polyvinyl alcohol and modified polyvinyl alcohol containing anions or cations, the alcoholysis degree of the polyvinyl alcohol free mixture is 70-99 mol%, and the polymerization degree is 500-3000.
5. The photosensitive resin composition according to claim 3, wherein: the acrylamide compound in the synthesis of the acrylamide modified polyvinyl alcohol resin solution is an acrylamide compound containing a hydroxyl functional group.
6. The photosensitive resin composition according to claim 3, wherein: the molar ratio of polyvinyl alcohol compounds to acrylamide compounds in the synthesis of the acrylamide modified polyvinyl alcohol resin solution is 2-12: 1, and the amount of phosphoric acid is 1-5% of the total amount of the polyvinyl alcohol compounds and the acrylamide compounds.
7. The photosensitive resin composition according to claim 6, wherein: the molar ratio of polyvinyl alcohol compounds to acrylamide compounds in the synthesis of the acrylamide modified polyvinyl alcohol resin solution is 4-8: 1, and the amount of phosphoric acid is 2-4% of the total amount of the polyvinyl alcohol compounds and the acrylamide compounds.
8. The photosensitive resin composition according to claim 1, wherein: the compound with the ethylenic unsaturated group is a compound with at least more than one ethylenic unsaturated group, the ethylenic unsaturated group compound comprises free radical polymerization monomers or oligomers, and the free radical polymerization monomers comprise monofunctional monomers or multifunctional monomers.
9. The photosensitive resin composition according to claim 1, wherein: the photocrosslinking agent comprises a water-soluble photocrosslinking agent and/or a radical polymerization photoinitiator, and the water-soluble photocrosslinking agent comprises one or more of diazo resin, dichromate or diazido compound.
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| CN113246462A (en) * | 2021-04-01 | 2021-08-13 | 厦门大学 | Method for constructing multilayer pattern in porous film through two-photon polymerization |
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