CA1065177A - Sensibilisants de type coumarine substituee en 3, pour polymeres photopolymerisables - Google Patents

Sensibilisants de type coumarine substituee en 3, pour polymeres photopolymerisables

Info

Publication number: CA1065177A
Authority: CA; Canada
Prior art keywords: carbon atoms; sensitizer; group; composition; alkyl
Prior art date: 1976-02-02
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

CA249,179A

Other languages

English (en)

Inventor

Donald P. Specht

Samir Y. Farid

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.)

Eastman Kodak Co

Original Assignee

Eastman Kodak 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.)

1976-02-02

Filing date

1976-03-30

Publication date

1979-10-30

1976-03-30 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1979-10-30 Application granted granted Critical

1979-10-30 Publication of CA1065177A publication Critical patent/CA1065177A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 56
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims abstract description 40
235000001671 coumarin Nutrition 0.000 title claims abstract description 26
229960000956 coumarin Drugs 0.000 title claims description 20
125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 title 1
239000000463 material Substances 0.000 claims abstract description 47
150000001540 azides Chemical class 0.000 claims abstract description 14
-1 coumarin compound Chemical class 0.000 claims description 80
125000004432 carbon atom Chemical group C* 0.000 claims description 67
239000000203 mixture Substances 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
HYORIVUCOQKMOC-UHFFFAOYSA-N 3-benzoyl-7-methoxychromen-2-one Chemical group O=C1OC2=CC(OC)=CC=C2C=C1C(=O)C1=CC=CC=C1 HYORIVUCOQKMOC-UHFFFAOYSA-N 0.000 claims description 8
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
SANIRTQDABNCHF-UHFFFAOYSA-N 7-(diethylamino)-3-[7-(diethylamino)-2-oxochromene-3-carbonyl]chromen-2-one Chemical group C1=C(N(CC)CC)C=C2OC(=O)C(C(=O)C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=CC2=C1 SANIRTQDABNCHF-UHFFFAOYSA-N 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
229920002678 cellulose Polymers 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
ITJVTQLTIZXPEQ-UHFFFAOYSA-N 3-benzoyl-5,7-dimethoxychromen-2-one Chemical group O=C1OC2=CC(OC)=CC(OC)=C2C=C1C(=O)C1=CC=CC=C1 ITJVTQLTIZXPEQ-UHFFFAOYSA-N 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
JPPGTVYDWHSNLJ-UHFFFAOYSA-N 2-benzoylbenzo[f]chromen-3-one Chemical group C=1C(C2=CC=CC=C2C=C2)=C2OC(=O)C=1C(=O)C1=CC=CC=C1 JPPGTVYDWHSNLJ-UHFFFAOYSA-N 0.000 claims description 3
FEIQOMCWGDNMHM-UHFFFAOYSA-N 5-phenylpenta-2,4-dienoic acid Chemical class OC(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-N 0.000 claims description 3
IBAIMVHLKHXHMS-UHFFFAOYSA-N 6-phenylhexa-1,5-dien-3-one Chemical compound C=CC(=O)CC=CC1=CC=CC=C1 IBAIMVHLKHXHMS-UHFFFAOYSA-N 0.000 claims description 3
239000004793 Polystyrene Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000002837 carbocyclic group Chemical group 0.000 claims description 3
239000001913 cellulose Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
229920013821 hydroxy alkyl cellulose Polymers 0.000 claims description 3
229920002223 polystyrene Polymers 0.000 claims description 3
230000001235 sensitizing effect Effects 0.000 claims description 3
229920006305 unsaturated polyester Polymers 0.000 claims description 3
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
TWCSYAMFXMQIAP-UHFFFAOYSA-N 3-(5,7-diethoxy-2-oxochromene-3-carbonyl)-5,7-diethoxychromen-2-one Chemical group C1=C(OCC)C=C2OC(=O)C(C(=O)C3=CC4=C(OCC)C=C(C=C4OC3=O)OCC)=CC2=C1OCC TWCSYAMFXMQIAP-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
DWDONSBFIIUPQS-UHFFFAOYSA-N 3-benzoyl-7-(dimethylamino)chromen-2-one Chemical group O=C1OC2=CC(N(C)C)=CC=C2C=C1C(=O)C1=CC=CC=C1 DWDONSBFIIUPQS-UHFFFAOYSA-N 0.000 claims 2
DOPJDUKVDLSBPL-UHFFFAOYSA-N 3-(1-benzofuran-2-carbonyl)-7-(diethylamino)chromen-2-one Chemical group C1=CC=C2OC(C(=O)C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=CC2=C1 DOPJDUKVDLSBPL-UHFFFAOYSA-N 0.000 claims 1
POTFCSBOXWLDJQ-UHFFFAOYSA-N 3-(2-oxo-5,7-dipropoxychromene-3-carbonyl)-5,7-dipropoxychromen-2-one Chemical group C1=C(OCCC)C=C2OC(=O)C(C(=O)C3=CC4=C(OCCC)C=C(C=C4OC3=O)OCCC)=CC2=C1OCCC POTFCSBOXWLDJQ-UHFFFAOYSA-N 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
229930016911 cinnamic acid Natural products 0.000 claims 1
235000013985 cinnamic acid Nutrition 0.000 claims 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
239000000178 monomer Substances 0.000 abstract description 16
150000004775 coumarins Chemical class 0.000 abstract description 7
206010073306 Exposure to radiation Diseases 0.000 abstract description 2
238000000576 coating method Methods 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
239000011248 coating agent Substances 0.000 description 26
238000002360 preparation method Methods 0.000 description 16
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
235000019441 ethanol Nutrition 0.000 description 14
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 10
229910052753 mercury Inorganic materials 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229910052782 aluminium Inorganic materials 0.000 description 8
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
238000001816 cooling Methods 0.000 description 7
230000005855 radiation Effects 0.000 description 7
229920002554 vinyl polymer Polymers 0.000 description 7
239000007789 gas Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
HJRFKKRMCGZIOA-UHFFFAOYSA-N 3-acetyl-7-methoxy-1-benzopyran-2-one Chemical compound C1=C(C(C)=O)C(=O)OC2=CC(OC)=CC=C21 HJRFKKRMCGZIOA-UHFFFAOYSA-N 0.000 description 5
QXAMGWKESXGGNV-UHFFFAOYSA-N 7-(diethylamino)-1-benzopyran-2-one Chemical compound C1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 QXAMGWKESXGGNV-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229910052724 xenon Inorganic materials 0.000 description 3
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
FQRQWPNYJOFDLO-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxybenzaldehyde Chemical compound COC1=CC(O)=C(C=O)C(OC)=C1 FQRQWPNYJOFDLO-UHFFFAOYSA-N 0.000 description 2
QWZHDKGQKYEBKK-UHFFFAOYSA-N 3-aminochromen-2-one Chemical compound C1=CC=C2OC(=O)C(N)=CC2=C1 QWZHDKGQKYEBKK-UHFFFAOYSA-N 0.000 description 2
RNJOKCPFLQMDEC-UHFFFAOYSA-N 4(R),8-dimethyl-trans-2-nonenoyl-CoA Chemical compound COC(=O)CC(=O)CC(=O)OC RNJOKCPFLQMDEC-UHFFFAOYSA-N 0.000 description 2
NXJCRELRQHZBQA-UHFFFAOYSA-N 5,7-dimethoxy-1-benzopyran-2-one Chemical compound C1=CC(=O)OC2=CC(OC)=CC(OC)=C21 NXJCRELRQHZBQA-UHFFFAOYSA-N 0.000 description 2
VVWFQAZJYRJAJT-UHFFFAOYSA-N 5,7-dimethoxy-3-(7-methoxy-2-oxochromene-3-carbonyl)chromen-2-one Chemical compound C1=C(OC)C=C2OC(=O)C(C(=O)C3=CC4=CC=C(C=C4OC3=O)OC)=CC2=C1OC VVWFQAZJYRJAJT-UHFFFAOYSA-N 0.000 description 2
GZEYLLPOQRZUDF-UHFFFAOYSA-N 7-(dimethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(N(C)C)=CC=C21 GZEYLLPOQRZUDF-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
241001082241 Lythrum hyssopifolia Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229920006037 cross link polymer Polymers 0.000 description 2
GGRQLKPIJPFWEZ-UHFFFAOYSA-N cycloprop-2-en-1-one Chemical compound O=C1C=C1 GGRQLKPIJPFWEZ-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000003384 imaging method Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
NGZOTIQHWZXUDI-UHFFFAOYSA-N methyl 3-[7-(diethylamino)-2-oxochromen-3-yl]-3-oxopropanoate Chemical compound C1=C(C(=O)CC(=O)OC)C(=O)OC2=CC(N(CC)CC)=CC=C21 NGZOTIQHWZXUDI-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000139 polyethylene terephthalate Polymers 0.000 description 2
239000005020 polyethylene terephthalate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000011160 research Methods 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000003107 substituted aryl group Chemical group 0.000 description 2
JMMVHMOAIMOMOF-UHFFFAOYSA-N (4-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=C(OC(=O)C=C)C=C1 JMMVHMOAIMOMOF-UHFFFAOYSA-N 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
QWIIPRYMQRDLQI-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-phenylcycloprop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(C1=O)=C1C1=CC=CC=C1 QWIIPRYMQRDLQI-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
UAMPJVJAALGMNG-UHFFFAOYSA-N 2-acetylbenzo[f]chromen-3-one Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)C)=C3C=CC2=C1 UAMPJVJAALGMNG-UHFFFAOYSA-N 0.000 description 1
DDOSYAJVNWEFNC-UHFFFAOYSA-N 2-azidoethenylbenzene Chemical compound [N-]=[N+]=NC=CC1=CC=CC=C1 DDOSYAJVNWEFNC-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
LXCJXYYYOPFEDH-UHFFFAOYSA-N 3-(2-oxochromene-3-carbonyl)chromen-2-one Chemical compound C1=CC=C2OC(=O)C(C(C=3C(OC4=CC=CC=C4C=3)=O)=O)=CC2=C1 LXCJXYYYOPFEDH-UHFFFAOYSA-N 0.000 description 1
UZHUWERFNUBSKH-UHFFFAOYSA-N 3-(4-nitrobenzoyl)chromen-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC2=CC=CC=C2OC1=O UZHUWERFNUBSKH-UHFFFAOYSA-N 0.000 description 1
HFJQJYLCHQZGJD-UHFFFAOYSA-N 3-(5,5-dimethoxy-2-oxo-3h-chromene-3-carbonyl)-7-methoxychromen-2-one Chemical compound O=C1OC2=CC(OC)=CC=C2C=C1C(=O)C(C(O1)=O)C=C2C1=CC=CC2(OC)OC HFJQJYLCHQZGJD-UHFFFAOYSA-N 0.000 description 1
XTFHNDSRQORPMK-UHFFFAOYSA-N 3-(5,7-dimethoxy-2-oxochromene-3-carbonyl)-5,7-dimethoxychromen-2-one Chemical compound C1=C(OC)C=C2OC(=O)C(C(=O)C3=CC4=C(OC)C=C(C=C4OC3=O)OC)=CC2=C1OC XTFHNDSRQORPMK-UHFFFAOYSA-N 0.000 description 1
WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
NJMDIBINSUKPEB-UHFFFAOYSA-N 3-[3-(4-ethoxyphenyl)prop-2-enoyl]-7-methoxychromen-2-one Chemical compound C1=CC(OCC)=CC=C1C=CC(=O)C1=CC2=CC=C(OC)C=C2OC1=O NJMDIBINSUKPEB-UHFFFAOYSA-N 0.000 description 1
HRYGAHKVVJRXNT-UHFFFAOYSA-N 3-[5,7-bis(2-chloroethoxy)-2-oxochromene-3-carbonyl]-5,7-bis(2-chloroethoxy)chromen-2-one Chemical compound C1=C(OCCCl)C=C2OC(=O)C(C(=O)C3=CC4=C(OCCCl)C=C(C=C4OC3=O)OCCCl)=CC2=C1OCCCl HRYGAHKVVJRXNT-UHFFFAOYSA-N 0.000 description 1
NZASAYJPZFDDHB-UHFFFAOYSA-N 3-[7-(diethylamino)-2-oxochromene-3-carbonyl]-5,7-dimethoxychromen-2-one Chemical compound C1=C(OC)C=C2OC(=O)C(C(=O)C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=CC2=C1OC NZASAYJPZFDDHB-UHFFFAOYSA-N 0.000 description 1
LPBMPRKJYKSRLL-UHFFFAOYSA-N 3-benzoylchromen-2-one Chemical compound C=1C2=CC=CC=C2OC(=O)C=1C(=O)C1=CC=CC=C1 LPBMPRKJYKSRLL-UHFFFAOYSA-N 0.000 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 1
HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 1
CGPLHNZMBJLLKS-UHFFFAOYSA-N 5,7-dibutoxychromen-2-one Chemical compound C1=CC(=O)OC2=CC(OCCCC)=CC(OCCCC)=C21 CGPLHNZMBJLLKS-UHFFFAOYSA-N 0.000 description 1
125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
VKVCJIMMVPXDQD-UHFFFAOYSA-N 6-methoxycoumarin Chemical compound O1C(=O)C=CC2=CC(OC)=CC=C21 VKVCJIMMVPXDQD-UHFFFAOYSA-N 0.000 description 1
XYFXTIBDEAZMAH-UHFFFAOYSA-N 6-methoxycoumarin Natural products O1C(=O)C=CC2=C1C=CC=C2OC XYFXTIBDEAZMAH-UHFFFAOYSA-N 0.000 description 1
GDRWYGWOZQAYRI-UHFFFAOYSA-N 7-(diethylamino)-3-(thiophene-3-carbonyl)chromen-2-one Chemical compound O=C1OC2=CC(N(CC)CC)=CC=C2C=C1C(=O)C=1C=CSC=1 GDRWYGWOZQAYRI-UHFFFAOYSA-N 0.000 description 1
RHROYFNIWOPJAZ-UHFFFAOYSA-N 7-(dimethylamino)-3-(4-iodobenzoyl)chromen-2-one Chemical compound O=C1OC2=CC(N(C)C)=CC=C2C=C1C(=O)C1=CC=C(I)C=C1 RHROYFNIWOPJAZ-UHFFFAOYSA-N 0.000 description 1
QZXAEJGHNXJTSE-UHFFFAOYSA-N 7-(ethylamino)-4,6-dimethylchromen-2-one Chemical compound O1C(=O)C=C(C)C2=C1C=C(NCC)C(C)=C2 QZXAEJGHNXJTSE-UHFFFAOYSA-N 0.000 description 1
FWFVXBZXJKTVGL-UHFFFAOYSA-N 7-methoxy-2-oxo-1-benzopyran-3-carboxylic acid ethyl ester Chemical compound C1=C(OC)C=C2OC(=O)C(C(=O)OCC)=CC2=C1 FWFVXBZXJKTVGL-UHFFFAOYSA-N 0.000 description 1
YAIJOSLAACTSGD-UHFFFAOYSA-N 7-methoxy-3-(4-methoxybenzoyl)chromen-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC2=CC=C(OC)C=C2OC1=O YAIJOSLAACTSGD-UHFFFAOYSA-N 0.000 description 1
KCURVNYQRJVWPY-UHFFFAOYSA-N 7-methoxy-3-(7-methoxy-2-oxochromene-3-carbonyl)chromen-2-one Chemical compound C1=C(OC)C=C2OC(=O)C(C(=O)C3=CC4=CC=C(C=C4OC3=O)OC)=CC2=C1 KCURVNYQRJVWPY-UHFFFAOYSA-N 0.000 description 1
ODRDTKMYQDXVGG-UHFFFAOYSA-N 8-methoxycoumarin Natural products C1=CC(=O)OC2=C1C=CC=C2OC ODRDTKMYQDXVGG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
229920008347 Cellulose acetate propionate Polymers 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910000599 Cr alloy Inorganic materials 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000490229 Eucephalus Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
BIKUSPFVCCVYNF-UHFFFAOYSA-N O1C(=CC2=C1C=CC=C2)C(=O)C=2C(OC1=CC(=CC=C1C2)OC)=O.C(C2=CN=CC=C2)(=O)C=2C(OC1=CC(=CC=C1C2)OC)=O.C(C)N(C2=CC=C1C=C(C(OC1=C2)=O)C(=O)C=2C(OC1=CC=C(C=C1C2)OC)=O)CC Chemical compound O1C(=CC2=C1C=CC=C2)C(=O)C=2C(OC1=CC(=CC=C1C2)OC)=O.C(C2=CN=CC=C2)(=O)C=2C(OC1=CC(=CC=C1C2)OC)=O.C(C)N(C2=CC=C1C=C(C(OC1=C2)=O)C(=O)C=2C(OC1=CC=C(C=C1C2)OC)=O)CC BIKUSPFVCCVYNF-UHFFFAOYSA-N 0.000 description 1
OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 1
206010034960 Photophobia Diseases 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
PDWCVHGVTVOSIE-UHFFFAOYSA-N [nitro(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([N+](=O)[O-])C1=CC=CC=C1 PDWCVHGVTVOSIE-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
238000012644 addition polymerization Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920006217 cellulose acetate butyrate Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
OKTUKULVIWUXDU-UHFFFAOYSA-N chromen-2-one 3-(5,7-dimethoxy-2-oxochromene-3-carbonyl)-5,7-dimethoxychromen-2-one Chemical compound C(=O)(C=1C(OC2=CC(=CC(=C2C1)OC)OC)=O)C=1C(OC2=CC(=CC(=C2C1)OC)OC)=O.O1C(=O)C=CC2=CC=CC=C12 OKTUKULVIWUXDU-UHFFFAOYSA-N 0.000 description 1
DYHCYUYLRFEFHI-UHFFFAOYSA-N chromen-2-one;7-(diethylamino)-4-methylchromen-2-one Chemical compound C1=CC=C2OC(=O)C=CC2=C1.CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 DYHCYUYLRFEFHI-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000000788 chromium alloy Substances 0.000 description 1
229940114081 cinnamate Drugs 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000002508 contact lithography Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
125000001142 dicarboxylic acid group Chemical group 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
239000011888 foil Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LIIALPBMIOVAHH-UHFFFAOYSA-N herniarin Chemical compound C1=CC(=O)OC2=CC(OC)=CC=C21 LIIALPBMIOVAHH-UHFFFAOYSA-N 0.000 description 1
JHGVLAHJJNKSAW-UHFFFAOYSA-N herniarin Natural products C1CC(=O)OC2=CC(OC)=CC=C21 JHGVLAHJJNKSAW-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
229910003475 inorganic filler Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
208000013469 light sensitivity Diseases 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical class OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
125000001400 nonyl 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])C([H])([H])[H] 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
230000003287 optical effect Effects 0.000 description 1
239000012766 organic filler Substances 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
208000017983 photosensitivity disease Diseases 0.000 description 1
231100000434 photosensitization Toxicity 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001603 poly (alkyl acrylates) Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920006267 polyester film Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
FWYIBGHGBOVPNL-UHFFFAOYSA-N scopoletin Natural products COC=1C=C2C=CC(OC2=C(C1)O)=O FWYIBGHGBOVPNL-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
101150008563 spir gene Proteins 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
- 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
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/695—Compositions containing azides as the photosensitive substances
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/60—Processes for obtaining vesicular images
- 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
- G03F7/008—Azides
- G03F7/0085—Azides characterised by the non-macromolecular additives
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029

Landscapes

Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Organic Chemistry (AREA)
General Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Polymerisation Methods In General (AREA)

CA249,179A 1976-02-02 1976-03-30 Sensibilisants de type coumarine substituee en 3, pour polymeres photopolymerisables Expired CA1065177A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US65448576A	1976-02-02	1976-02-02

Publications (1)

Publication Number	Publication Date
CA1065177A true CA1065177A (fr)	1979-10-30

Family

ID=24625047

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA249,179A Expired CA1065177A (fr)	1976-02-02	1976-03-30	Sensibilisants de type coumarine substituee en 3, pour polymeres photopolymerisables

Country Status (3)

Country	Link
BE (1)	BE851024A (fr)
CA (1)	CA1065177A (fr)
SE (1)	SE419679B (fr)

1976
- 1976-03-30 CA CA249,179A patent/CA1065177A/fr not_active Expired
1977
- 1977-02-02 SE SE7701110A patent/SE419679B/xx unknown
- 1977-02-02 BE BE174609A patent/BE851024A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
SE419679B (sv)	1981-08-17
BE851024A (fr)	1977-08-02
SE7701110L (sv)	1977-08-03

Publication	Publication Date	Title
US4147552A (en)	1979-04-03	Light-sensitive compositions with 3-substituted coumarin compounds as spectral sensitizers
GB1578662A (en)	1980-11-05	Photosensitive compositions
US4119466A (en)	1978-10-10	Sensitizers for photocrosslinkable polymers
CA1314892C (fr)	1993-03-23	Colorants polymethine et absorbants u.-v. contenant un groupe triarylborylisocyano, et substances pour l'imagerie
CA1131395A (fr)	1982-09-07	Derives d'arylcetones et de p-dialkyl- aminoarylaldehydes servant comme sensibilisation de substances photopolymerisables dans le spectre du visible
US5534633A (en)	1996-07-09	Aminoketone sensitizers for photopolymer compositions
US4410621A (en)	1983-10-18	Photosensitive resin containing a combination of diphenyl-imiazolyl dimer and a heterocyclic mercaptan
US5480994A (en)	1996-01-02	Aminoketone sensitizers for aqueous soluble photopolymer compositions
US4459349A (en)	1984-07-10	Photosensitive resin composition
CA1335595C (fr)	1995-05-16	Composes photosensibles
JPH02216154A (ja)	1990-08-29	感光性組成物、光安定性ホログラムを作成する一段法および基体上にホトレジストを形成する方法
US4966830A (en)	1990-10-30	Photopolymerizable composition
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AU606231B2 (en)	1991-01-31	Photopolymerizable composition
JPS6353992B2 (fr)	1988-10-26
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