CN101121762A - Alkali-soluble polymer and its preparation method - Google Patents
Alkali-soluble polymer and its preparation method Download PDFInfo
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- CN101121762A CN101121762A CNA2006101681049A CN200610168104A CN101121762A CN 101121762 A CN101121762 A CN 101121762A CN A2006101681049 A CNA2006101681049 A CN A2006101681049A CN 200610168104 A CN200610168104 A CN 200610168104A CN 101121762 A CN101121762 A CN 101121762A
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- vinyl
- alkali
- soluble polymer
- polymerization
- polymer according
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- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 239000000126 substance Substances 0.000 claims abstract description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 60
- 229920002554 vinyl polymer Polymers 0.000 claims description 58
- 238000006116 polymerization reaction Methods 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000010526 radical polymerization reaction Methods 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 229960004217 benzyl alcohol Drugs 0.000 claims description 2
- 238000012661 block copolymerization Methods 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000012673 precipitation polymerization Methods 0.000 claims description 2
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 239000003513 alkali Substances 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 8
- 239000005977 Ethylene Substances 0.000 abstract description 4
- 238000005299 abrasion Methods 0.000 abstract description 3
- 150000003254 radicals Chemical class 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 3
- 230000000379 polymerizing effect Effects 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000035945 sensitivity Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000011521 glass Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- -1 O-naphthoquinones disazo compound Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229920003987 resole Polymers 0.000 description 12
- 239000003999 initiator Substances 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 230000003750 conditioning effect Effects 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N vinyl ethyl ether Natural products CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical class CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000001733 1,4-Heptonolactone Substances 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- NOGAOMOVCCMSHA-UHFFFAOYSA-N 1-ethenyl-3-ethoxy-2-methylbenzene Chemical compound CCOC1=CC=CC(C=C)=C1C NOGAOMOVCCMSHA-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- ZQNOJCUGMIJPKB-UHFFFAOYSA-N 2-chloroacetic acid;ethene Chemical compound C=C.OC(=O)CCl ZQNOJCUGMIJPKB-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- MENFYLMQVDPRMG-UHFFFAOYSA-N 2-methoxyoxirane Chemical compound COC1CO1 MENFYLMQVDPRMG-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- OUIITAOCYATDMY-UHFFFAOYSA-N 4-amino-2-phenylphenol Chemical compound NC1=CC=C(O)C(C=2C=CC=CC=2)=C1 OUIITAOCYATDMY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 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
- 150000001656 butanoic acid esters Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LWHHJLHIEMBQCB-UHFFFAOYSA-N ethene;2-phenylacetic acid Chemical compound C=C.OC(=O)CC1=CC=CC=C1 LWHHJLHIEMBQCB-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical class CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 description 1
- VYHUMZYFJVMWRC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methylprop-2-enamide Chemical compound OCCN(C)C(=O)C=C VYHUMZYFJVMWRC-UHFFFAOYSA-N 0.000 description 1
- JTIYHGKVWGMRLH-UHFFFAOYSA-N n-(2-oxopropyl)prop-2-enamide Chemical compound CC(=O)CNC(=O)C=C JTIYHGKVWGMRLH-UHFFFAOYSA-N 0.000 description 1
- OFHYREWCAQPIQI-UHFFFAOYSA-N n-hexyl-n-methylprop-2-enamide Chemical compound CCCCCCN(C)C(=O)C=C OFHYREWCAQPIQI-UHFFFAOYSA-N 0.000 description 1
- IZXGMKHVTNJFAA-UHFFFAOYSA-N n-methyl-n-phenylprop-2-enamide Chemical compound C=CC(=O)N(C)C1=CC=CC=C1 IZXGMKHVTNJFAA-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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- Photosensitive Polymer And Photoresist Processing (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention discloses a alkali soluble polymer and its preparing method, the polymer is prepared from ethylene monomer through free radical polymerizing method or other polymerizing method, wherein the structural formula of the ethylene monomer with two functions of -COOH and -CONH-R as follows: HOOC-C=C-CONH-R, R means the Phenolic group, hydroxy or carboxy function. The alkali soluble polymer can comprises one or more other ethylene monomer selectively. A thermal sensitive lithographic printing plate prepared by the alkali soluble polymer has excellent chemical resistance performance, abrasion resistance, high sensitivity, low film wear and wide development degree.
Description
Technical field
The present invention relates to a kind of alkali-soluble polymer and preparation method thereof, concrete, the present invention relates to a kind of alkali-soluble polymer that is applied to prepare light-sensitive composition and imaging element and positive heat-sensitive planographic plate, this alkali-soluble polymer contains vinyl monomer and obtains by radical polymerization and other polymerization process.
Background technology
Alkali-soluble polymer has been widely used in light-sensitive composition and imaging element and fields such as printed circuit board (PCB) (PCB) and lithographic plate.Representative way is that alkali-soluble polymer and light absorber and other components dissolved are obtained light-sensitive composition in suitable solvent, and light-sensitive composition is coated with on the substrate, and drying and/or slaking then makes it form thin film.When using suitable source of radiation or particle beam to shine, be irradiated to the film of scope and have different attributes with the film that is not irradiated to scope.Compare with the film that is not irradiated to scope, the solubleness of film in alkaline solution that is irradiated to scope changes.This method is a kind of method of making lithographic plate of using at most at present.The sensitive layer of traditional PS lithographic plate mainly comprises O-naphthoquinones disazo compound and alkali soluble resin, and the solubleness of alkali soluble resin in alkaline solution is subjected to the inhibition of O-naphthoquinones disazo compound.Under ultraviolet light radiation, O-naphthoquinones disazo compound resolves into the indenes carboxylic acid with photochemistry, causes resistance dissolubility forfeiture recited above, thereby causes the solvability of sensitive layer in alkali lye obviously to improve.
When preparation traditional PS lithographic plate, using maximum alkali soluble resins at present is resol.Because the resol chemical resistance is relatively poor, low chemical resistance has seriously influenced the compatibility of the chemical that press plate and some printing process must use, and then the functions of use of reduction press plate.In the videograph process of positive lithographic plate, improving film-remaining ratio is an important challenge.Cause the low major cause of film-remaining ratio still because the serious dissolving of unexposed portion in developing solution.In order to improve film-remaining ratio, people must utilize exposure carefully and do not have exposed portion to the recently intensity and the development time of balance developing solution.
Obviously, have only the exploitation a kind of chemical resistance preferably alkali soluble resin prepare lithographic plate, just can make lithographic plate have better chemical resistance and higher film-remaining ratio.
Summary of the invention
The object of the present invention is to provide a kind of alkali-soluble polymer that is applied to prepare light-sensitive composition and imaging element and printing heat-sensitive lithographic printing planography, this alkali-soluble polymer is obtained by radical polymerization and other polymerization process by vinyl monomer.Prepared positive heat-sensitive planographic plate has good chemical resistance, advantages of good abrasion and highly sensitive, low film loss rate and wide development degree.
The concrete technical scheme that the present invention adopts is as follows:
A kind of alkali-soluble polymer is characterized in that: described polymkeric substance contains vinyl monomer and obtains by radical polymerization and other polymerization process, wherein contain-COOH is expressed as follows with the structural formula of the vinyl monomer of-two kinds of functional groups of CONH-R:
HOOC-C＝C-CONH-R
R represents to have phenolic group, the functional group of hydroxyl or carboxyl.
The molecular-weight average that vinyl polymerization body of the present invention has is 1000-100,000, be particularly suitable for being 5000-50, and 000, molecular weight dispersity is 1.1-10.
The quality of vinyl monomer in the vinyl polymerization body that contains two kinds of functional groups of the present invention is 10%-100% than content, is preferably 20%-70%, is particularly suitable for being 25%-50%.Can contain unreacted monomer in the vinyl polymerization body, the quality of these monomers in the vinyl polymerization body, is preferably in below 1% below 5% than content.
Polymer of the present invention also comprises other one or more vinyl monomers, mainly comprises following a few class:
(methyl) esters of acrylic acid comprises: (methyl) methyl acrylate, Jia Jibingxisuanyizhi, 2-chloroethyl (methyl) acrylate, hydroxyethyl (methyl) acrylate, (methyl) acrylate glyceryl ester, (methyl) phenyl acrylate, (methyl) vinylformic acid benzene methyl;
Vinyl cyanide comprises: methacrylonitrile, vinyl cyanide;
(methyl) acrylic amide comprises: N, N-dimethyl (methyl) acrylamide, N-hydroxyethyl (methyl) acrylamide, N-(right-hydroxybenzene) (methyl) acrylamide, N-hexyl (methyl) acrylamide, N-phenyl (methyl) acrylamide;
Styrenic comprises: vinylbenzene, vinyl toluene, dimethyl styrene, 1-chloro-4-methyl-benzene, ethoxyl methyl vinylbenzene, hydroxy styrenes, chloro-styrene;
Vinyl esters comprises: vinyl acetate, hylene butyric acid ester, vinyl acetate, ethene chloracetate, vinyl methoxyacetic acid ester, ethene phenylacetate, vinyl benzoic acid ester;
Vinyl ethers comprises: ethylene methacrylic ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, octyl group Vinyl Ether, methoxy-ethylene ether, vinyl ethyl ether ether, hydroxyethyl Vinyl Ether;
Unsaturated acid imide comprises: maleimide, N-acryl acrylamide, N-acetylmethyl acrylamide;
Unsaturated acids comprises: vinylformic acid, methacrylic acid, maleic anhydride, methylene-succinic acid;
Above monomer is preferred: vinylformic acid, methacrylic acid, methacrylonitrile, vinyl cyanide, methyl methacrylate, methyl acrylate or N,N-DMAA.
Alkali-soluble polymer of the present invention is to make by the homopolymerization of vinyl monomer with the copolymerization of other vinyl monomer, and method comprises known radical polymerization, anionoid polymerization, cationoid polymerisation, graft copolymerization, block copolymerization, random copolymerization, letex polymerization, suspension polymerization, precipitation polymerization or mass polymerization.
In Raolical polymerizable, available radical initiator comprises: superoxide such as dibenzoyl peroxide; Azo-compound such as Diisopropyl azodicarboxylate; Oxidation-reduction system such as dibenzoyl peroxide/N, accelerine and photolysis compound such as benzophenone.
In anionic polymerisation, available anionic initiator comprises: basic metal alkylate such as sodium alkyl, lithium alkylide; Metal amine compound such as potassium amide; Contain the anionic compound of alcoxyl such as sodium methylate and Lewis base.
In cationic polymerization, available cationic initiator comprises: protonic acid such as phosphoric acid, sulfuric acid; Lewis acid such as aluminum chloride, zinc chloride; Carbonium ion salt such as trityl carbonium ion; Halogen such as iodine and cation light initiator.
The required solvent of described polyreaction is selected acetone, butanone, pimelinketone, toluene, dimethylbenzene, methyl alcohol, ethanol, propyl alcohol, propyl alcohol, isopropylcarbinol, tetrahydrofuran (THF), ethylene glycol monomethyl ether, propylene glycol monomethyl ether, N, dinethylformamide, N,N-dimethylacetamide, ethyl acetate, dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone or phenylcarbinol.Above solvent can use separately also and can two or more mixing use.
The temperature of described polyreaction is 80～250 ℃, preferred 20～120 ℃, and preferred especially 50～100 ℃.
After polyreaction of the present invention finished, products therefrom can reclaim by the method for filtering-depositing.Water and alcohol are precipitation agents preferably.Reclaim the polymkeric substance that obtains and under 0～200 ℃, carry out drying, preferred 50～120 ℃, preferred especially 50～100 ℃.
The positive heat-sensitive planographic plate that is made by alkali-soluble polymer of the present invention has good chemical resistance, advantages of good abrasion and highly sensitive, low film loss rate and wide development degree.
Embodiment
Embodiment 1: vinyl monomer (HOOC-C=C-CONH-R, R=phenol) synthetic
Take by weighing 49 gram MALEIC ANHYDRIDE respectively and be dissolved in 125 milliliters of acetone, 86 gram p-aminophenol are dissolved in 400 milliliters of acetone, the maleic acid anhydride solution is poured in the glass reactor, and reactor placed on the ice bath, then the p-aminophenyl phenol solution is dropwise joined in the glass reactor, until adding.After treating reinforced finishing, the gained mixed solution is placed under the room temperature again and stirred 24 hours, filter then, vacuum-drying promptly gets the vinyl monomer finished product.
Embodiment 2: vinyl polymerization body A's is synthetic
60 milliliters of ethanol, 140 milliliters of propylene glycol monomethyl ethers are added in 500 milliliters of round bottom glass reaction bottles, agitator, thermometer, nitrogen inlet and reflux exchanger are housed on the glass reaction bottle.Take by weighing vinyl monomer prepared in the synthetic illustration 1 of 4 grams, 16 gram vinylbenzene, 3 gram vinyl cyanide then respectively and add in the reaction flasks, under the normal temperature after the stirring and dissolving.Again 1 gram Diisopropyl azodicarboxylate initiator is added reaction flask, stirred 12 hours down at 80 ℃ then.After the cooling mixed solution is poured in the water, through precipitation, filter after, with products therefrom vinyl polymerization body A with methanol wash twice, and in 40 ℃ temperature condition dry 2 days down.
Embodiment 3: vinyl polymerization body B's is synthetic
174 milliliters of ethanol, 116 milliliters of propylene glycol monomethyl ethers are added in 500 milliliters of round bottom glass reaction bottles, agitator, thermometer, nitrogen inlet and reflux exchanger are housed on the glass reaction bottle.The vinyl monomer, 30 gram vinylbenzene, 4 gram methacrylic acids and the 34 gram methyl methacrylates that take by weighing preparation in the synthetic illustration 1 of 55 grams then respectively add in the reaction flask, under the normal temperature after the stirring and dissolving, again 0.8 gram Diisopropyl azodicarboxylate initiator is added reaction flask, stirred 12 hours down at 80 ℃ then.After the cooling mixed solution is poured in the water, through precipitation, filter after, with products therefrom vinyl polymerization body B with methanol wash twice, and in 40 ℃ temperature condition dry 2 days down.
Embodiment 4: vinyl polymerization body C's is synthetic
125 milliliters of ethanol, 190 milliliters of propylene glycol monomethyl ethers are added in 500 milliliters of round bottom glass reaction bottles, agitator, thermometer, nitrogen inlet and reflux exchanger are housed on the glass reaction bottle.The vinyl monomer, 22 gram vinylbenzene, 3.6 gram N-(2-hydroxyethyl) Methacrylamides and the 34 gram methyl methacrylates that take by weighing preparation in the synthetic illustration 1 of 6.4 grams then respectively add in the reaction flask, under the normal temperature after the stirring and dissolving, again 0.35 gram Diisopropyl azodicarboxylate initiator is added reaction flask, stirred 12 hours down at 80 ℃ then.After the cooling mixed solution is poured in the water, through precipitation, filter after, with products therefrom vinyl polymerization body C with methanol wash twice, and in 40 ℃ temperature condition dry 2 days down.
Embodiment 5: vinyl polymerization body D's is synthetic
57 milliliters of ethanol, 38 milliliters of propylene glycol monomethyl ethers are added in 500 milliliters of round bottom glass reaction bottles, agitator, thermometer, nitrogen inlet and reflux exchanger are housed on the glass reaction bottle.The vinyl monomer, 11.5 gram vinylbenzene and the 12.7 gram methyl methacrylates that take by weighing preparation in the synthetic illustration 1 of 15 grams then respectively add in the reaction flask, under the normal temperature after the stirring and dissolving, again 0.16 gram Diisopropyl azodicarboxylate initiator is added reaction flask, stirred 12 hours down at 80 ℃ then.After the cooling mixed solution is poured in the water, through precipitation, filter after, with products therefrom vinyl polymerization body D with methanol wash twice, and in 40 ℃ temperature condition dry 2 days down.
Embodiment 6: vinyl polymerization body E's is synthetic
57 milliliters of ethanol, 38 milliliters of propylene glycol monomethyl ethers are added in 500 milliliters of round bottom glass reaction bottles, agitator, thermometer, nitrogen inlet and reflux exchanger are housed on the glass reaction bottle.The vinyl monomer, 8.3 gram vinylbenzene and the 12 gram Jia Jibingxisuanyizhis that take by weighing preparation in the synthetic illustration 1 of 15 grams then respectively add in the reaction flask, under the normal temperature after the stirring and dissolving, again 0.13 gram Diisopropyl azodicarboxylate initiator is added reaction flask, stirred 12 hours down at 80 ℃ then.After the cooling mixed solution is poured in the water, through precipitation, filter after, with products therefrom vinyl polymerization body E with methanol wash twice, and in 40 ℃ temperature condition dry 2 days down.
Embodiment 7: vinyl polymerization body F's is synthetic
57 milliliters of ethanol, 38 milliliters of propylene glycol monomethyl ethers are added in 500 milliliters of round bottom glass reaction bottles, agitator, thermometer, nitrogen inlet and reflux exchanger are housed on the glass reaction bottle.The vinyl monomer, 8.3 gram vinylbenzene and the 15 gram Jia Jibingxisuanyizhis that take by weighing preparation in the synthetic illustration 1 of 15 grams then respectively add in the reaction flask, under the normal temperature after the stirring and dissolving, again 0.13 gram Diisopropyl azodicarboxylate initiator is added reaction flask, stirred 12 hours down at 80 ℃ then.After the cooling mixed solution is poured in the water, through precipitation, filter after, with products therefrom vinyl polymerization body F with methanol wash twice, and in 40 ℃ temperature condition dry 2 days down.
Embodiment 8: solubleness conditioning agent A's is synthetic
1) in 600 milliliters of glass beakers, 50 gram resol is dissolved under stirring in the 325 gram acetone, then gained solution is cooled to 10 ℃, add 30 gram p-methyl benzene sulfonic chlorides again, the dissolving back slowly adds 14.77 gram triethylamines, in 10 ℃ of following stirring reactions 1 hour, add 1.36 gram acetate again, got intermediate product in 1 hour in 10 ℃ of following stirring reactions;
2) 3 kg of ice and 3 kg water are placed 7.5 liters glass beaker, in stirring down 5 gram acetate are joined in ice-water mixture, then prepared intermediate product is equally divided into 4 parts by 25% weight ratio, 1 part that gets wherein slowly adds in the ice-water mixture under stirring, obtains 1 part of solubleness conditioning agent A through precipitation, filtration and drying.Above step triplicate obtains 4 parts of totally 78 gram solubleness conditioning agent A respectively.
Embodiment 9: solubleness conditioning agent B's is synthetic
1) in 600 milliliters of glass beakers, 50 gram resol is dissolved under stirring in the 325 gram acetone, then gained solution is cooled to 10 ℃, add 15 gram p-methyl benzene sulfonic chlorides again, the dissolving back slowly adds 7.34 gram triethylamines, in 10 ℃ of following stirring reactions 1 hour, add 1.36 gram acetate again, got intermediate product in 1 hour in 10 ℃ of following stirring reactions;
2) 3 kg of ice and 3 kg water are placed 7.5 liters glass beaker, in stirring down 5 gram acetate are joined in ice-water mixture, then prepared intermediate product is equally divided into 4 parts by 25% weight ratio, 1 part that gets wherein slowly adds in the ice-water mixture under stirring, obtains 1 part of solubleness conditioning agent A through precipitation, filtration and drying.Above step triplicate obtains 4 parts of totally 78 gram solubleness conditioning agent A respectively.
Embodiment 10: chemical resistance simultaneous test 1
The light-sensitive composition rotary coating that to make by following weight proportion on the anodised aluminium substrate surface, in 110 ℃ baking oven dry 5 minutes, obtain book film dry weight and be 1.6 grams/square metre.
Polymer 9.8 grams
Infrared dyes ADS830A 0.1 gram
Victoria's pure blue B OH 0.1 gram
Methylethylketone 10 grams
Propylene glycol monomethyl ether 80 grams
The test of chemical resistance is carried out in following three kinds of mixing solutionss: mixing solutions one: concentration of volume percent is 80% DAA (diketone alcohol) aqueous solution; Mixing solutions two: concentration of volume percent is 80% the ethylene glycol monobutyl ether aqueous solution; Mixing solutions three: concentration of volume percent is 80% isopropanol water solution.Coating is by the corrosive time sees Table 1 fully:
Table 1: chemical resistance comparative test result
| The contained polymer of composition | 80% diketone spirituous solution | 80% ethylene glycol monobutyl ether solution | 80% aqueous isopropanol |
| Resol PF6564LB | 20 seconds | 15 seconds | 15 seconds |
| Resol 0744LB01 | 25 seconds | 20 seconds | 15 seconds |
| Resol 6866LB02 | 25 seconds | 20 seconds | 30 seconds |
| Vinyl polymerization body A | 74 minutes | 190 minutes | ＞60 minutes |
| Vinyl polymerization body B | 105 seconds | 60 seconds | 100 seconds |
| Vinyl polymerization body C | 225 seconds | 85 seconds | 900 seconds |
| Vinyl polymerization body D | 90 seconds | 120 seconds | 960 seconds |
| Vinyl polymerization body E | 370 seconds | 65 seconds | 530 seconds |
| Vinyl polymerization body F | 185 seconds | 45 seconds | 765 seconds |
The result shows: the composition that contains vinyl polymerization body of the present invention contains the composition of common alkali soluble polymeric body resol, has significant advantage on chemical resistance.
Embodiment 11: chemical resistance simultaneous test 2
The light-sensitive composition rotary coating that to make by following weight proportion on the anodised aluminium substrate surface, in 110 ℃ baking oven dry 5 minutes, obtain book film dry weight and be 1.6 grams/square metre.
Polymer 6.3 grams
Solubleness conditioning agent A 3.5 grams
Infrared dyes ADS830A 0.1 gram
Victoria's pure blue B OH 0.1 gram
Methylethylketone 10 grams
Propylene glycol monomethyl ether 80 grams
The test of chemical resistance is carried out in following three kinds of mixing solutionss: mixing solutions one: concentration of volume percent is 80% DAA (diketone alcohol) aqueous solution; Mixing solutions two: concentration of volume percent is 80% the ethylene glycol monobutyl ether aqueous solution; Mixing solutions three: concentration of volume percent is 80% isopropanol water solution.Coating is by the corrosive time sees Table 2 fully:
Table 2: chemical resistance comparative test result
| The contained polymer of composition | 80% diketone spirituous solution | 80% ethylene glycol monobutyl ether solution | 80% aqueous isopropanol |
| Resol PF6564LB | 30 seconds | 35 seconds | 15 seconds |
| Resol 0744LB01 | 40 seconds | 30 seconds | 20 seconds |
| Resol 6866LB02 | 55 seconds | 20 seconds | 20 seconds |
| Special vinyl polymerization body A | 225 seconds | 110 seconds | ＞65 minutes |
| Special vinyl polymerization body B | 110 seconds | 35 seconds | 225 seconds |
| Special vinyl polymerization body C | 255 seconds | 55 seconds | ＞＞10 minutes |
| Special vinyl polymerization body D | 235 seconds | 75 seconds | ＞＞10 minutes |
| Special vinyl polymerization body E | 135 seconds | 50 seconds | ＞＞10 minutes |
| Special vinyl polymerization body F | 95 seconds | 60 seconds | ＞＞10 minutes |
The result shows: the composition that contains vinyl polymerization body of the present invention contains the composition of common alkali soluble polymeric body resol, has significant advantage on chemical resistance.
Claims (10)
1. alkali-soluble polymer is characterized in that: described polymkeric substance contains vinyl monomer and obtains by radical polymerization and other polymerization process, wherein contain-COOH is expressed as follows with the structural formula of the vinyl monomer of-two kinds of functional groups of CONH-R:
HOOC-C＝C-CONH-R
R represents to have phenolic group, the functional group of hydroxyl or carboxyl.
2. alkali-soluble polymer according to claim 1 is characterized in that: the quality of the vinyl monomer of described two kinds of functional groups in the vinyl polymerization body is 10%-100% than content.
3. alkali-soluble polymer according to claim 1 and 2 is characterized in that: the quality of the vinyl monomer of described two kinds of functional groups in the vinyl polymerization body is 20%-70% than content.
4. alkali-soluble polymer according to claim 1 is characterized in that: the molecular-weight average that described vinyl polymerization body has is 1000-100,000.
5. according to claim 1 or 4 described alkali-soluble polymers, it is characterized in that: the molecular-weight average that described vinyl polymerization body has is 5000-50,000.
6. alkali-soluble polymer according to claim 5 is characterized in that: the dispersity of the molecular weight that described vinyl polymerization body has is 1.1-10.
7. alkali-soluble polymer according to claim 1 is characterized in that: can also comprise other one or more vinyl monomers in this polymkeric substance, mainly comprise following a few class:
(methyl) esters of acrylic acid, vinyl cyanide, (methyl) acrylic amide, styrenic, vinyl esters, vinyl ethers, unsaturated acid imide, unsaturated acids.
8. alkali-soluble polymer according to claim 1, it is characterized in that: the required solvent of described polyreaction is selected acetone, butanone, pimelinketone, toluene, dimethylbenzene, methyl alcohol, ethanol, propyl alcohol, propyl alcohol, isopropylcarbinol, tetrahydrofuran (THF), ethylene glycol monomethyl ether, propylene glycol monomethyl ether, N, dinethylformamide, N,N-dimethylacetamide, ethyl acetate, dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone or phenylcarbinol.Above solvent can use separately also and can two or more mixing use.
9. the preparation method of alkali-soluble polymer according to claim 1, it is characterized in that: vinyl monomer is after finishing polyreaction under 0～250 ℃ the temperature condition, products therefrom is deposited in water or the alcohol, and the polymkeric substance that will reclaim gained after filtering again is in 10～200 ℃ of dry down products that get.
10. the preparation method of alkali-soluble polymer according to claim 8 is characterized in that: described vinyl polymerization reaction comprises radical polymerization, anionoid polymerization, cationoid polymerisation, graft copolymerization, block copolymerization, random copolymerization, letex polymerization, suspension polymerization, precipitation polymerization or mass polymerization.
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| CN102741750A (en) * | 2009-12-28 | 2012-10-17 | 株式会社微处理 | Photosensitive resin composition, photosensitive dry film and pattern forming method |
| US8647806B2 (en) | 2009-12-28 | 2014-02-11 | Micro Process Inc | Photosensitive resin composition, photosensitive dry film and method for forming pattern |
| CN104341551A (en) * | 2013-08-09 | 2015-02-11 | 三菱丽阳株式会社 | Method of manufacturing polymer for lithography, method of manufacturing resist composition, and method of manufacturing substrate having pattern |
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| CN101762972B (en) * | 2008-12-24 | 2012-12-26 | 成都新图新材料股份有限公司 | Infrared positive thermal-sensitive imaging composition |
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| EP3587113B1 (en) * | 2018-06-21 | 2023-01-04 | Agfa Offset Bv | A lithographic printing plate precursor |
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| EP0930540B1 (en) * | 1996-10-02 | 2004-06-16 | Sanyo Chemical Industries, Ltd. | Photosensitive composition and use thereof |
| EP0860742B1 (en) * | 1997-02-25 | 2001-04-04 | E.I. Du Pont De Nemours And Company | Flexible, flame-retardant, photoimageable composition for coating printing circuits |
| US6672210B2 (en) * | 2000-07-13 | 2004-01-06 | Fuji Photo Film Co., Ltd. | Lithographic printing plate precursor with a graft polymerized hydrophilic layer |
| WO2002014382A1 (en) * | 2000-08-16 | 2002-02-21 | Brewer Science, Inc. | Photosensitive resin compositions for color filter applications |
| CN1235089C (en) * | 2000-11-23 | 2006-01-04 | 富士胶片株式会社 | Photosensitive lithographic printing plate |
| CN1259189C (en) * | 2003-12-12 | 2006-06-14 | 北京豹驰方正技术发展有限公司 | Application type positive property thermal sensitive computer direct board and process for making same |
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| CN102741750A (en) * | 2009-12-28 | 2012-10-17 | 株式会社微处理 | Photosensitive resin composition, photosensitive dry film and pattern forming method |
| US8647806B2 (en) | 2009-12-28 | 2014-02-11 | Micro Process Inc | Photosensitive resin composition, photosensitive dry film and method for forming pattern |
| US8647807B2 (en) | 2009-12-28 | 2014-02-11 | Micro Process Inc. | Photosensitive resin composition, photosensitive dry film and method for forming pattern |
| CN102741750B (en) * | 2009-12-28 | 2017-03-01 | 株式会社微处理 | Photosensitive resin composition, photosensitive dry film and pattern forming method |
| CN104341551A (en) * | 2013-08-09 | 2015-02-11 | 三菱丽阳株式会社 | Method of manufacturing polymer for lithography, method of manufacturing resist composition, and method of manufacturing substrate having pattern |
| CN104341551B (en) * | 2013-08-09 | 2017-06-09 | 三菱丽阳株式会社 | The manufacture method of the manufacture method of lithographic printing polymer, the manufacture method of anti-corrosion agent composition and the figuratum substrate of formation |
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