NO764338L - - Google Patents

Info

Publication number: NO764338L
Authority: NO; Norway
Prior art keywords: group; hydrogen; formula; mol; phenyl
Prior art date: 1975-12-23

Application number

NO764338A

Other languages

English (en)

Norwegian (no)

Inventor

A P Gates

S C Hinch

C V Withers

Original Assignee

Vickers Ltd

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.)

1975-12-23

Filing date

1976-12-22

Publication date

1977-06-24

1976-12-22 Application filed by Vickers Ltd filed Critical Vickers Ltd

1977-06-24 Publication of NO764338L publication Critical patent/NO764338L/no

Links

-1 cyano- Chemical class 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
229920000642 polymer Polymers 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
239000000463 material Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000004185 ester group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000000178 monomer Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical group CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
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 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 description 60
230000015572 biosynthetic process Effects 0.000 description 58
239000011347 resin Substances 0.000 description 35
229920005989 resin Polymers 0.000 description 35
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
239000002253 acid Substances 0.000 description 32
238000000034 method Methods 0.000 description 26
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
238000004519 manufacturing process Methods 0.000 description 18
239000003513 alkali Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 16
238000002360 preparation method Methods 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
229910052782 aluminium Inorganic materials 0.000 description 11
239000000047 product Substances 0.000 description 11
BLPUXJIIRIWMSQ-QPJJXVBHSA-N 2-[(e)-3-phenylprop-2-enylidene]propanedioic acid Chemical compound OC(=O)C(C(O)=O)=C\C=C\C1=CC=CC=C1 BLPUXJIIRIWMSQ-QPJJXVBHSA-N 0.000 description 10
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000002924 oxiranes Chemical class 0.000 description 7
230000005855 radiation Effects 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
239000004115 Sodium Silicate Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229940117916 cinnamic aldehyde Drugs 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
239000000975 dye Substances 0.000 description 4
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
235000019795 sodium metasilicate Nutrition 0.000 description 4
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
229910052911 sodium silicate Inorganic materials 0.000 description 4
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
239000012467 final product Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
230000035945 sensitivity Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
JKTVNBZTQKQRSH-DUXPYHPUSA-N (e)-3-(3-nitrophenyl)prop-2-enal Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\C=O)=C1 JKTVNBZTQKQRSH-DUXPYHPUSA-N 0.000 description 2
ZCJLOOJRNPHKAV-ONEGZZNKSA-N (e)-3-(furan-2-yl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CO1 ZCJLOOJRNPHKAV-ONEGZZNKSA-N 0.000 description 2
UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-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
WPRWWXUEGMTZQP-UHFFFAOYSA-N 2-[3-(2-nitrophenyl)prop-2-enylidene]propanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC=CC1=CC=CC=C1[N+]([O-])=O WPRWWXUEGMTZQP-UHFFFAOYSA-N 0.000 description 2
QNHZVWIRNFIAND-UHFFFAOYSA-N 2-[3-(3-nitrophenyl)prop-2-enylidene]propanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC=CC1=CC=CC([N+]([O-])=O)=C1 QNHZVWIRNFIAND-UHFFFAOYSA-N 0.000 description 2
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
238000005299 abrasion Methods 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 2
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910052724 xenon Inorganic materials 0.000 description 2
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 1
GTQLBYROWRZDHS-DUXPYHPUSA-N (e)-3-(3-chlorophenyl)prop-2-enal Chemical compound ClC1=CC=CC(\C=C\C=O)=C1 GTQLBYROWRZDHS-DUXPYHPUSA-N 0.000 description 1
HONRSHHPFBMLBT-OWOJBTEDSA-N (e)-3-(4-chlorophenyl)prop-2-enal Chemical compound ClC1=CC=C(\C=C\C=O)C=C1 HONRSHHPFBMLBT-OWOJBTEDSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
CVMYEWFFFUKQEF-UHFFFAOYSA-N 1-chloro-2-(2-chloroethenoxy)ethene Chemical compound ClC=COC=CCl CVMYEWFFFUKQEF-UHFFFAOYSA-N 0.000 description 1
KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
DBKFZYNQPCAQSG-UHFFFAOYSA-N 2-(2-phenylethenyl)-1,3-dioxane-4,6-dione Chemical compound O1C(=O)CC(=O)OC1C=CC1=CC=CC=C1 DBKFZYNQPCAQSG-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
STXVKZXWIGREFT-UHFFFAOYSA-N 2-cyano-5-(4-methylphenyl)penta-2,4-dienoic acid Chemical compound CC1=CC=C(C=CC=C(C#N)C(O)=O)C=C1 STXVKZXWIGREFT-UHFFFAOYSA-N 0.000 description 1
UBDXZYYYWGIRGN-UHFFFAOYSA-N 2-cyano-5-phenylpenta-2,4-dienoic acid Chemical compound OC(=O)C(C#N)=CC=CC1=CC=CC=C1 UBDXZYYYWGIRGN-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
239000001431 2-methylbenzaldehyde Substances 0.000 description 1
VMSMELHEXDVEDE-HWKANZROSA-N 2-nitrocinnamaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1\C=C\C=O VMSMELHEXDVEDE-HWKANZROSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
VRWKAXRIXMCDDY-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-phenylprop-2-enoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)=CC1=CC=C(Cl)C=C1 VRWKAXRIXMCDDY-UHFFFAOYSA-N 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
DFVYOEWFOJYXQS-UHFFFAOYSA-N CC[K].OC(=O)CC(O)=O Chemical compound CC[K].OC(=O)CC(O)=O DFVYOEWFOJYXQS-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical class CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
206010034972 Photosensitivity reaction Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
238000005882 aldol condensation reaction Methods 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
229930008407 benzylideneacetone Natural products 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
229940114081 cinnamate Drugs 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
238000007654 immersion Methods 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
230000036211 photosensitivity Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000003260 vortexing Methods 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Spectroscopy & Molecular Physics (AREA)
General Physics & Mathematics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Macromonomer-Based Addition Polymer (AREA)
Polymerisation Methods In General (AREA)

NO764338A 1975-12-23 1976-12-22 NO764338L (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB52522/75A GB1572441A (en)	1975-12-23	1975-12-23	Photopolymerisable polymers with free carboxyl groups and printing plates therefrom

Publications (1)

Publication Number	Publication Date
NO764338L true NO764338L (cs)	1977-06-24

Family

ID=10464243

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO764338A NO764338L (cs)	1975-12-23	1976-12-22

Country Status (27)

Country	Link
US (1)	US4263394A (cs)
JP (1)	JPS5286488A (cs)
AT (1)	AT348552B (cs)
AU (1)	AU510145B2 (cs)
BE (1)	BE849803A (cs)
BR (1)	BR7608579A (cs)
CA (1)	CA1107444A (cs)
CH (1)	CH629314A5 (cs)
CS (1)	CS212783B2 (cs)
DE (1)	DE2658272A1 (cs)
DK (1)	DK579976A (cs)
ES (1)	ES454521A1 (cs)
FI (1)	FI64863C (cs)
FR (1)	FR2336707A1 (cs)
GB (1)	GB1572441A (cs)
IE (1)	IE44405B1 (cs)
IT (1)	IT1065419B (cs)
KE (1)	KE3336A (cs)
LU (1)	LU76465A1 (cs)
MW (1)	MW5276A1 (cs)
NL (1)	NL7614259A (cs)
NO (1)	NO764338L (cs)
NZ (1)	NZ182955A (cs)
PL (1)	PL103094B1 (cs)
SE (1)	SE424642B (cs)
ZA (1)	ZA767635B (cs)
ZM (1)	ZM15276A1 (cs)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4343888A (en)	1980-05-01	1982-08-10	E. I. Du Pont De Nemours And Company	Use of radiation crosslinkable polyesters and polyesterethers in printing plates
US4284710A (en)	1980-05-01	1981-08-18	E. I. Du Pont De Nemours And Company	Radiation crosslinkable polyesters and polyesterethers
US4592816A (en) *	1984-09-26	1986-06-03	Rohm And Haas Company	Electrophoretic deposition process
DE3528929A1 (de) *	1985-08-13	1987-02-26	Hoechst Ag	Strahlungsempfindliches gemisch, dieses enthaltendes strahlungsempfindliches aufzeichnungsmaterial und verfahren zur herstellung von reliefbildern
WO1996034316A1 (en) *	1995-04-27	1996-10-31	Minnesota Mining And Manufacturing Company	Negative-acting no-process printing plates
US5925497A (en)	1995-04-27	1999-07-20	Minnesota Mining And Manufacturing Company	Negative-acting no-process printing plates
US6159658A (en) *	1996-03-19	2000-12-12	Toray Industries, Inc.	Photosensitive resin composition with polymer having an ionic group and having a polymerizable group in the side chain and printing plate materials
AU2001248201B2 (en) *	2000-04-13	2006-12-14	Hsc Research And Development Limited Partnership	Compounds for modulating cell proliferation
CA2407755A1 (en) *	2002-10-11	2004-04-11	The Hospital For Sick Children	Inhibition of vegf secretion
WO2005012234A1 (en) *	2003-07-30	2005-02-10	The Hospital For Sick Children	Compounds for modulating cell proliferation
WO2005092904A1 (en) *	2004-03-26	2005-10-06	Hsc Research And Development Limited Partnership	Novel compounds for modulating cell proliferation
US8778568B2 (en) *	2010-12-14	2014-07-15	General Electric Company	Optical data storage media and methods for using the same
CN113031394B (zh) *	2019-12-09	2025-07-22	北京鼎材科技有限公司	一种感光树脂组合物及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3799915A (en) *	1971-08-20	1974-03-26	Western Litho Plate & Supply	Photopolymers
US3993684A (en) *	1971-08-20	1976-11-23	Western Litho Plate & Supply Co.	Monomeric compounds
US4065430A (en) *	1973-02-13	1977-12-27	Fuji Photo Film Co., Ltd.	Functional group containing polymer and method of preparing the same

1975
- 1975-12-23 GB GB52522/75A patent/GB1572441A/en not_active Expired
1976
- 1976-12-20 SE SE7614315A patent/SE424642B/xx not_active IP Right Cessation
- 1976-12-21 CA CA268,315A patent/CA1107444A/en not_active Expired
- 1976-12-21 BR BR7608579A patent/BR7608579A/pt unknown
- 1976-12-21 PL PL1976194590A patent/PL103094B1/pl unknown
- 1976-12-22 MW MW52/76A patent/MW5276A1/xx unknown
- 1976-12-22 FR FR7638665A patent/FR2336707A1/fr active Granted
- 1976-12-22 AU AU20818/76A patent/AU510145B2/en not_active Expired
- 1976-12-22 DE DE19762658272 patent/DE2658272A1/de not_active Withdrawn
- 1976-12-22 DK DK579976A patent/DK579976A/da not_active Application Discontinuation
- 1976-12-22 FI FI763683A patent/FI64863C/fi not_active IP Right Cessation
- 1976-12-22 NO NO764338A patent/NO764338L/no unknown
- 1976-12-22 NZ NZ182955A patent/NZ182955A/xx unknown
- 1976-12-22 NL NL7614259A patent/NL7614259A/xx not_active Application Discontinuation
- 1976-12-22 IE IE2806/76A patent/IE44405B1/en unknown
- 1976-12-22 CH CH1619976A patent/CH629314A5/de not_active IP Right Cessation
- 1976-12-23 LU LU76465A patent/LU76465A1/xx unknown
- 1976-12-23 AT AT964076A patent/AT348552B/de not_active IP Right Cessation
- 1976-12-23 ZA ZA767635A patent/ZA767635B/xx unknown
- 1976-12-23 CS CS768572A patent/CS212783B2/cs unknown
- 1976-12-23 IT IT30822/76A patent/IT1065419B/it active
- 1976-12-23 ES ES454521A patent/ES454521A1/es not_active Expired
- 1976-12-23 JP JP15433576A patent/JPS5286488A/ja active Pending
- 1976-12-23 BE BE173590A patent/BE849803A/xx not_active IP Right Cessation
- 1976-12-29 ZM ZM152/76A patent/ZM15276A1/xx unknown
1979
- 1979-06-18 US US06/049,272 patent/US4263394A/en not_active Expired - Lifetime
1983
- 1983-10-05 KE KE3336A patent/KE3336A/xx unknown

Also Published As

Publication number	Publication date
ZA767635B (en)	1977-11-30
SE7614315L (sv)	1977-06-24
NL7614259A (nl)	1977-06-27
CH629314A5 (de)	1982-04-15
SE424642B (sv)	1982-08-02
MW5276A1 (en)	1978-02-08
AU510145B2 (en)	1980-06-12
NZ182955A (en)	1979-04-26
IT1065419B (it)	1985-02-25
CA1107444A (en)	1981-08-18
AT348552B (de)	1979-02-26
FI763683A7 (cs)	1977-06-24
IE44405B1 (en)	1981-11-18
KE3336A (en)	1983-11-04
DE2658272A1 (de)	1977-07-14
GB1572441A (en)	1980-07-30
CS212783B2 (en)	1982-03-26
AU2081876A (en)	1978-06-29
PL103094B1 (pl)	1979-05-31
FR2336707A1 (fr)	1977-07-22
ES454521A1 (es)	1977-12-01
US4263394A (en)	1981-04-21
BE849803A (fr)	1977-06-23
FR2336707B1 (cs)	1983-04-29
LU76465A1 (cs)	1977-06-15
BR7608579A (pt)	1977-12-27
FI64863C (fi)	1984-01-10
FI64863B (fi)	1983-09-30
ZM15276A1 (en)	1978-03-21
JPS5286488A (en)	1977-07-18
ATA964076A (de)	1978-07-15
IE44405L (en)	1977-06-23
DK579976A (da)	1977-06-24

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US3849137A (en)	1974-11-19	Lithographic printing plates and photoresists comprising a photosensitive polymer
US4736055A (en)	1988-04-05	Oxime sulfonates containing reactive groups
CA1168792A (en)	1984-06-05	Mixture which is polymerizable by radiation, and radiation-sensitive copying material prepared therewith
US4496447A (en)	1985-01-29	Aromatic-aliphatic ketones useful as photoinitiators
CA1267656A (en)	1990-04-10	Photoinitiators for photopolymerization of unsaturated systems
US5200299A (en)	1993-04-06	Quinoline and acridine compounds effective as photoinitiators and containing polymerizable (meth)acryloyl substituents
US4263394A (en)	1981-04-21	Aqueous alkaline soluble photopolymerizable material
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US2824084A (en)	1958-02-18	Light-sensitive, unsaturated polymeric maleic and acrylic derivatives
US2816091A (en)	1957-12-10	Polymeric chalcones and their use as light-sensitive polymers
US5834157A (en)	1998-11-10	2-acylamino-9-arylacridines, process for their preparation and photosensitive mixtures containing them
US4117039A (en)	1978-09-26	Light sensitive materials
JP3302759B2 (ja)	2002-07-15	光重合開始剤
US4254244A (en)	1981-03-03	Light-sensitive materials
FI62911C (fi)	1983-03-10	Ljuskaensliga material
US4569901A (en)	1986-02-11	Poly(N-benzyl acrylamide) polymer containing negative photoresist compositions
US5358999A (en)	1994-10-25	Process for preparation of photosensitive compositions of stilbazolium quaternary
JPS5869208A (ja)	1983-04-25	光不溶化性ポリビニルアルコ−ル誘導体の製造方法
US5286603A (en)	1994-02-15	Radiation sensitive plates