CA1103084A - Photopolymerizable composition containing an o- nitroaromatic compound as photoinhibitor - Google Patents

Photopolymerizable composition containing an o- nitroaromatic compound as photoinhibitor

Info

Publication number: CA1103084A
Authority: CA; Canada
Prior art keywords: carbons; alkyl; radiation; component; exposure
Prior art date: 1976-03-17
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.): Expired

Application number

CA273,994A

Other languages

English (en)

French (fr)

Inventor

Jose F. Pazos

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1976-03-17

Filing date

1977-03-15

Publication date

1981-06-16

1977-03-15 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1981-06-16 Application granted granted Critical

1981-06-16 Publication of CA1103084A publication Critical patent/CA1103084A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 70
239000000203 mixture Substances 0.000 title claims description 69
230000005855 radiation Effects 0.000 claims abstract description 115
239000000758 substrate Substances 0.000 claims abstract description 29
239000008199 coating composition Substances 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims description 57
238000000576 coating method Methods 0.000 claims description 56
239000011248 coating agent Substances 0.000 claims description 52
238000000034 method Methods 0.000 claims description 48
-1 R5 is H Chemical group 0.000 claims description 32
239000003112 inhibitor Substances 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 20
238000006116 polymerization reaction Methods 0.000 claims description 20
239000007787 solid Substances 0.000 claims description 18
229920000642 polymer Polymers 0.000 claims description 17
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 13
239000011230 binding agent Substances 0.000 claims description 9
239000000539 dimer Substances 0.000 claims description 9
229940096522 trimethylolpropane triacrylate Drugs 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000000743 hydrocarbylene group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
229920000058 polyacrylate Chemical class 0.000 claims description 7
238000010521 absorption reaction Methods 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
230000008033 biological extinction Effects 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
229920005862 polyol Polymers 0.000 claims description 6
150000003077 polyols Chemical class 0.000 claims description 6
238000010526 radical polymerization reaction Methods 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
YWSPWKXREVSQCA-UHFFFAOYSA-N 4,5-dimethoxy-2-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=C([N+]([O-])=O)C=C1OC YWSPWKXREVSQCA-UHFFFAOYSA-N 0.000 claims description 5
239000004721 Polyphenylene oxide Chemical class 0.000 claims description 5
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 5
239000000049 pigment Substances 0.000 claims description 5
229920000570 polyether Chemical class 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000005395 methacrylic acid group Chemical class 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
238000012644 addition polymerization Methods 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
150000001555 benzenes Chemical class 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000002843 carboxylic acid group Chemical class 0.000 claims description 3
235000017168 chlorine Nutrition 0.000 claims description 3
125000001309 chloro group Chemical class Cl* 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
SCOAVUHOIJMIBW-UHFFFAOYSA-N phenanthrene-1,2-dione Chemical class C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1 SCOAVUHOIJMIBW-UHFFFAOYSA-N 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
125000005000 thioaryl group Chemical group 0.000 claims description 3
229920001567 vinyl ester resin Polymers 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
230000008569 process Effects 0.000 description 30
239000010408 film Substances 0.000 description 27
239000000178 monomer Substances 0.000 description 22
239000000243 solution Substances 0.000 description 22
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 17
239000005020 polyethylene terephthalate Substances 0.000 description 16
229920000139 polyethylene terephthalate Polymers 0.000 description 14
239000002253 acid Substances 0.000 description 11
239000004615 ingredient Substances 0.000 description 11
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
229910052782 aluminium Inorganic materials 0.000 description 7
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
229920001577 copolymer Polymers 0.000 description 7
NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 7
239000000976 ink Substances 0.000 description 7
125000000018 nitroso group Chemical group N(=O)* 0.000 description 7
229910052724 xenon Inorganic materials 0.000 description 7
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 7
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
239000003999 initiator Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
RMZQSAMHIQBMLW-UHFFFAOYSA-N 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O RMZQSAMHIQBMLW-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
239000000123 paper Substances 0.000 description 5
229940070721 polyacrylate Drugs 0.000 description 5
239000007921 spray Substances 0.000 description 5
235000012431 wafers Nutrition 0.000 description 5
MNKXKHNBVFVMKW-UHFFFAOYSA-N 2,5-bis[[4-(diethylamino)-2-methylphenyl]methylidene]cyclopentan-1-one Chemical compound CC1=CC(N(CC)CC)=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C(N(CC)CC)C=C1C MNKXKHNBVFVMKW-UHFFFAOYSA-N 0.000 description 4
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 4
229940054266 2-mercaptobenzothiazole Drugs 0.000 description 4
YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000006229 carbon black Substances 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000975 dye Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
230000000977 initiatory effect Effects 0.000 description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
ZYURHZPYMFLWSH-UHFFFAOYSA-N octacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC ZYURHZPYMFLWSH-UHFFFAOYSA-N 0.000 description 4
239000011550 stock solution Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
238000012719 thermal polymerization Methods 0.000 description 4
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
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 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
229940093475 2-ethoxyethanol Drugs 0.000 description 3
FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
206010073306 Exposure to radiation Diseases 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
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238000003384 imaging method Methods 0.000 description 3
150000002460 imidazoles Chemical class 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229920003145 methacrylic acid copolymer Polymers 0.000 description 3
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229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000012546 transfer Methods 0.000 description 3
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
OVOUKWFJRHALDD-UHFFFAOYSA-N 2-[2-(2-acetyloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(=O)OCCOCCOCCOC(C)=O OVOUKWFJRHALDD-UHFFFAOYSA-N 0.000 description 2
WPMUZECMAFLDQO-UHFFFAOYSA-N 2-[2-(2-hexanoyloxyethoxy)ethoxy]ethyl hexanoate Chemical compound CCCCCC(=O)OCCOCCOCCOC(=O)CCCCC WPMUZECMAFLDQO-UHFFFAOYSA-N 0.000 description 2
YJIHPMSQOPZABY-UHFFFAOYSA-N 2-nitrosobenzaldehyde Chemical compound O=CC1=CC=CC=C1N=O YJIHPMSQOPZABY-UHFFFAOYSA-N 0.000 description 2
XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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239000004904 UV filter Substances 0.000 description 2
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 2
150000008365 aromatic ketones Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
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239000003975 dentin desensitizing agent Substances 0.000 description 2
238000000586 desensitisation Methods 0.000 description 2
GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
QHMGJGNTMQDRQA-UHFFFAOYSA-N dotriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC QHMGJGNTMQDRQA-UHFFFAOYSA-N 0.000 description 2
238000010410 dusting Methods 0.000 description 2
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125000004494 ethyl ester group Chemical group 0.000 description 2
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238000010030 laminating Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
229940063557 methacrylate Drugs 0.000 description 2
239000003595 mist Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
150000002832 nitroso derivatives Chemical class 0.000 description 2
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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150000002894 organic compounds Chemical class 0.000 description 2
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PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
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238000002360 preparation method Methods 0.000 description 2
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235000017557 sodium bicarbonate Nutrition 0.000 description 2
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HCQVOLWYESYAAX-UHFFFAOYSA-N (2-benzoyl-5-octoxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 HCQVOLWYESYAAX-UHFFFAOYSA-N 0.000 description 1
DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 description 1
BWRBVBFLFQKBPT-UHFFFAOYSA-N (2-nitrophenyl)methanol Chemical compound OCC1=CC=CC=C1[N+]([O-])=O BWRBVBFLFQKBPT-UHFFFAOYSA-N 0.000 description 1
POGBODDHCBXBHZ-UHFFFAOYSA-N (3-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 POGBODDHCBXBHZ-UHFFFAOYSA-N 0.000 description 1
LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
CPHATJDZOWRKKE-UHFFFAOYSA-N (4-benzoyl-3-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC(OC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 CPHATJDZOWRKKE-UHFFFAOYSA-N 0.000 description 1
RYWGNBFHIFRNEP-UHFFFAOYSA-N (4-benzoylphenyl) 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 RYWGNBFHIFRNEP-UHFFFAOYSA-N 0.000 description 1
LTYBJDPMCPTGEE-UHFFFAOYSA-N (4-benzoylphenyl) prop-2-enoate Chemical compound C1=CC(OC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 LTYBJDPMCPTGEE-UHFFFAOYSA-N 0.000 description 1
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125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
238000007687 exposure technique Methods 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
230000004907 flux Effects 0.000 description 1
239000011888 foil Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000003475 lamination Methods 0.000 description 1
238000001459 lithography Methods 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
229940086559 methyl benzoin Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000004377 microelectronic Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
MDKQJOKKKZNQDG-UHFFFAOYSA-N n,n'-dimethylhexane-1,6-diamine Chemical compound CNCCCCCCNC MDKQJOKKKZNQDG-UHFFFAOYSA-N 0.000 description 1
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 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
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
125000004957 naphthylene group Chemical group 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
150000004841 phenylimidazoles Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920005596 polymer binder Polymers 0.000 description 1
239000002491 polymer binding agent Substances 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
229920001290 polyvinyl ester Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001902 propagating effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
- 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)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Spectroscopy & Molecular Physics (AREA)
General Physics & Mathematics (AREA)
Photosensitive Polymer And Photoresist Processing (AREA)
Polymerisation Methods In General (AREA)
Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA273,994A 1976-03-17 1977-03-15 Photopolymerizable composition containing an o- nitroaromatic compound as photoinhibitor Expired CA1103084A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US66753676A	1976-03-17	1976-03-17
US667,536		1976-03-17
US75869977A	1977-01-17	1977-01-17
US758,699		1977-01-17

Publications (1)

Publication Number	Publication Date
CA1103084A true CA1103084A (en)	1981-06-16

Family

ID=27099703

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA273,994A Expired CA1103084A (en)	1976-03-17	1977-03-15	Photopolymerizable composition containing an o- nitroaromatic compound as photoinhibitor

Country Status (6)

Country	Link
JP (1)	JPS589936B2 (nl)
CA (1)	CA1103084A (nl)
DE (1)	DE2710417C3 (nl)
FR (1)	FR2344869A1 (nl)
GB (1)	GB1547548A (nl)
NL (1)	NL183583C (nl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE852517A (fr) *	1976-03-17	1977-09-16	Du Pont	Composition photopolymerisable contenant un compose o-nitroaromatique comme photoinhibiteur et procedes de formation d'images a partir de cette composition
BE881232R (fr) *	1978-06-08	1980-07-18	Du Pont	Composition photopolymerisable contenant un compose o-nitro-aromatique comme photoinhibiteur et procedes de formation d'images a partir de cette composition
US4276152A (en) *	1979-09-24	1981-06-30	Mobil Oil Corporation	Reforming of sulfur-containing charge stock
US4268667A (en)	1980-04-21	1981-05-19	E. I. Du Pont De Nemours And Company	Derivatives of aryl ketones based on 9,10-dihydro-9,10-ethanoanthracene and p-dialkyl-aminoaryl aldehydes as visible sensitizers for photopolymerizable compositions
US4477556A (en) *	1982-08-18	1984-10-16	E. I. Du Pont De Nemours And Company	Acidic o-nitroaromatics as photoinhibitors of polymerization in positive working films
DE10326324B4 (de) *	2003-06-11	2007-02-08	Kodak Polychrome Graphics Gmbh	Lithographiedruckplatten-Vorläufer mit 1,4-Dihydropyridin-Sensibilisator enthaltender Beschichtung, Verfahren zum Bebildern und Bebilderte Lithographiedruckplatte

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3895952A (en) *	1973-02-09	1975-07-22	American Can Co	Phototropic compounds as acid catalyst for epoxy materials

1977
- 1977-03-10 DE DE19772710417 patent/DE2710417C3/de not_active Expired
- 1977-03-15 CA CA273,994A patent/CA1103084A/en not_active Expired
- 1977-03-16 GB GB1111077A patent/GB1547548A/en not_active Expired
- 1977-03-16 FR FR7707823A patent/FR2344869A1/fr active Granted
- 1977-03-17 NL NL7702887A patent/NL183583C/nl not_active IP Right Cessation
- 1977-03-17 JP JP52028752A patent/JPS589936B2/ja not_active Expired

Also Published As

Publication number	Publication date
GB1547548A (en)	1979-06-20
FR2344869A1 (fr)	1977-10-14
DE2710417C3 (de)	1980-08-14
NL183583C (nl)	1988-12-01
DE2710417B2 (de)	1979-12-06
JPS589936B2 (ja)	1983-02-23
NL183583B (nl)	1988-07-01
JPS52111985A (en)	1977-09-20
FR2344869B1 (nl)	1981-04-10
DE2710417A1 (de)	1977-09-29
NL7702887A (nl)	1977-09-20

Legal Events

Date	Code	Title	Description
1998-06-16	MKEX	Expiry

Publication	Publication Date	Title
US4269933A (en)	1981-05-26	Methods of developing photopolymerizable compositions containing an 0-nitroaromatic compound as photoinhibitor
US3885964A (en)	1975-05-27	Photoimaging process using nitroso dimer
US4255513A (en)	1981-03-10	Photopolymerizable recording materials
CA1336045C (en)	1995-06-27	Photopolymerizable mixture and recording material produced therefrom
US3661588A (en)	1972-05-09	Photopolymerizable compositions containing aminophenyl ketones and adjuvants
US4168982A (en)	1979-09-25	Photopolymerizable compositions containing nitroso dimers to selectively inhibit thermal polymerization
US4845011A (en)	1989-07-04	Visible light photoinitiation compositions
KR100535238B1 (ko)	2005-12-08	감광성 수지조성물, 이것을 사용한 감광성 엘레멘트,레지스트 패턴의 제조법 및 프린트 배선판의 제조법
US5645974A (en)	1997-07-08	Process for the production of printing plates
US4987055A (en)	1991-01-22	Photopolymerizable composition comprising (meth)acrylates with photooxidizable groups, and a recording material produced therefrom
KR101514900B1 (ko)	2015-04-23	감광성 수지 조성물, 및 이를 이용한 감광성 엘리먼트, 레지스트 패턴의 형성 방법 및 프린트 배선판의 제조 방법
JP5136423B2 (ja)	2013-02-06	感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
US4198242A (en)	1980-04-15	Photopolymerizable composition containing an o-nitroaromatic compound as photoinhibitor
CA1103084A (en)	1981-06-16	Photopolymerizable composition containing an o- nitroaromatic compound as photoinhibitor
US3901705A (en)	1975-08-26	Method of using variable depth photopolymerization imaging systems
US4029505A (en)	1977-06-14	Method of producing positive polymer images
US4985341A (en)	1991-01-15	Photopolymerizable mixture, and a recording material produced therefrom
US4050942A (en)	1977-09-27	Nitroso-dimer-containing compositions and photoimaging process
JP2706858B2 (ja)	1998-01-28	光重合性組成物
JP2801047B2 (ja)	1998-09-21	光重合性組成物
JP7425982B2 (ja)	2024-02-01	感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
JPH036202A (ja)	1991-01-11	光重合性組成物
JPS6076735A (ja)	1985-05-01	光硬化樹脂組成物
GB2068006A (en)	1981-08-05	Photopolymerizable Composition Containing an O- Nitroaromatic Compound as Photoinhibitor
JP7327485B2 (ja)	2023-08-16	感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法