CA1180486A - Polymeres possedant des radicaux thioxanthones comme chaines laterales - Google Patents

Polymeres possedant des radicaux thioxanthones comme chaines laterales

Info

Publication number: CA1180486A
Authority: CA; Canada
Prior art keywords: alkyl; hydrogen; atoms; formula; polymer
Prior art date: 1980-02-05
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

CA000431121A

Other languages

English (en)

Inventor

Vratislav Kvita

Hans Zweifel

Louis Felder

Martin Roth

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments 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.)

1980-02-05

Filing date

1983-06-22

Publication date

1985-01-02

1981-02-04 Priority claimed from CA000370083A external-priority patent/CA1163271A/fr

1983-06-22 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1983-06-22 Priority to CA000431121A priority Critical patent/CA1180486A/fr

1985-01-02 Application granted granted Critical

1985-01-02 Publication of CA1180486A publication Critical patent/CA1180486A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 104
150000001875 compounds Chemical class 0.000 claims abstract description 62
229910052739 hydrogen Inorganic materials 0.000 claims description 78
239000001257 hydrogen Substances 0.000 claims description 62
125000004432 carbon atom Chemical group C* 0.000 claims description 61
-1 -CONH2 Chemical group 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 52
150000002431 hydrogen Chemical group 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 15
239000000460 chlorine Chemical group 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052727 yttrium Inorganic materials 0.000 claims description 5
229910006069 SO3H Inorganic materials 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004956 cyclohexylene group Chemical group 0.000 claims description 2
125000004979 cyclopentylene group Chemical group 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
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 2
229910052729 chemical element Inorganic materials 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 24
231100000489 sensitizer Toxicity 0.000 abstract description 14
239000003999 initiator Substances 0.000 abstract description 13
238000004132 cross linking Methods 0.000 abstract description 10
150000001412 amines Chemical class 0.000 abstract description 9
235000013350 formula milk Nutrition 0.000 description 72
239000000243 solution Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000725 suspension Substances 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
229910052717 sulfur Inorganic materials 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
229960001701 chloroform Drugs 0.000 description 13
239000000047 product Substances 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000000576 coating method Methods 0.000 description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
150000003254 radicals Chemical class 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229920001577 copolymer Polymers 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 8
229960004132 diethyl ether Drugs 0.000 description 8
239000000178 monomer Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
229920000098 polyolefin Polymers 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
239000011248 coating agent Substances 0.000 description 6
238000006482 condensation reaction Methods 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
229940044600 maleic anhydride Drugs 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
229940073584 methylene chloride Drugs 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 6
229960005419 nitrogen Drugs 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
238000007259 addition reaction Methods 0.000 description 5
235000017168 chlorine Nutrition 0.000 description 5
229940060038 chlorine Drugs 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
125000005907 alkyl ester group Chemical group 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
229940093470 ethylene Drugs 0.000 description 4
229940093476 ethylene glycol Drugs 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000007639 printing Methods 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002125 Sokalan® Polymers 0.000 description 3
238000003848 UV Light-Curing Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000005396 acrylic acid ester group Chemical group 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008365 aromatic ketones Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000004584 polyacrylic acid Substances 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
238000010992 reflux Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 2
VUSUSPDOEWNKCH-UHFFFAOYSA-N 2-(4-methylphenyl)sulfanylterephthalic acid Chemical compound C1=CC(C)=CC=C1SC1=CC(C(O)=O)=CC=C1C(O)=O VUSUSPDOEWNKCH-UHFFFAOYSA-N 0.000 description 2
JYVLAKRCCBSMTQ-UHFFFAOYSA-N 2-phenyl-6-sulfanylcarbonylbenzoic acid Chemical compound OC(=O)C1=C(C(O)=S)C=CC=C1C1=CC=CC=C1 JYVLAKRCCBSMTQ-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
TUPRJRKRLLIIML-UHFFFAOYSA-N 3-phenyl-2-(phenylcarbamoyl)benzenecarbothioic s-acid Chemical compound C=1C=CC=CC=1N=C(O)C=1C(C(=S)O)=CC=CC=1C1=CC=CC=C1 TUPRJRKRLLIIML-UHFFFAOYSA-N 0.000 description 2
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
229920000178 Acrylic resin Polymers 0.000 description 2
239000004925 Acrylic resin Substances 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
229940048053 acrylate Drugs 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
239000012965 benzophenone Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
239000000306 component Substances 0.000 description 2
150000003950 cyclic amides Chemical class 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
150000003997 cyclic ketones Chemical class 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000000976 ink Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
150000002924 oxiranes Chemical group 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
230000005855 radiation Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
238000000016 photochemical curing Methods 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
239000006223 plastic coating Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
235000019394 potassium persulphate Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004224 protection Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
238000012549 training Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000431121A 1980-02-05 1983-06-22 Polymeres possedant des radicaux thioxanthones comme chaines laterales Expired CA1180486A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000431121A CA1180486A (fr)	1980-02-05	1983-06-22	Polymeres possedant des radicaux thioxanthones comme chaines laterales

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH917/80-3		1980-02-05
CH91780		1980-02-05
CA000370083A CA1163271A (fr)	1980-02-05	1981-02-04	Acides, esters, thioesters et amides thioxanthone- carboxyliques, possedant des groups fonctionnels reactifs
CA000431121A CA1180486A (fr)	1980-02-05	1983-06-22	Polymeres possedant des radicaux thioxanthones comme chaines laterales

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000370083A Division CA1163271A (fr)	1980-02-05	1981-02-04	Acides, esters, thioesters et amides thioxanthone- carboxyliques, possedant des groups fonctionnels reactifs

Publications (1)

Publication Number	Publication Date
CA1180486A true CA1180486A (fr)	1985-01-02

Family

ID=27166961

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000431121A Expired CA1180486A (fr)	1980-02-05	1983-06-22	Polymeres possedant des radicaux thioxanthones comme chaines laterales

Country Status (1)

Country	Link
CA (1)	CA1180486A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2199273A1 (fr)	2008-12-18	2010-06-23	AGFA Graphics NV	Photo-initiateurs polymérisables et compositions durcissables à rayonnement
WO2010133381A1 (fr)	2009-05-18	2010-11-25	Agfa Graphics Nv	Photoinitiateurs polymères polymérisables et compositions durcissables par un rayonnement
WO2019212865A1 (fr)	2018-04-30	2019-11-07	Basf Se	Polymères à masse molaire élevée issus d'un processus continu

1983
- 1983-06-22 CA CA000431121A patent/CA1180486A/fr not_active Expired

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2199273A1 (fr)	2008-12-18	2010-06-23	AGFA Graphics NV	Photo-initiateurs polymérisables et compositions durcissables à rayonnement
US8492452B2 (en)	2008-12-18	2013-07-23	Agfa Graphics Nv	Polymerizable photoinitiators and radiation curable compositions
WO2010133381A1 (fr)	2009-05-18	2010-11-25	Agfa Graphics Nv	Photoinitiateurs polymères polymérisables et compositions durcissables par un rayonnement
US8883873B2 (en)	2009-05-18	2014-11-11	Agfa Graphics Nv	Polymerizable polymeric photoinitiators and radiation curable compositions
WO2019212865A1 (fr)	2018-04-30	2019-11-07	Basf Se	Polymères à masse molaire élevée issus d'un processus continu

Legal Events

Date	Code	Title	Description
2002-01-02	MKEX	Expiry

Publication	Publication Date	Title
CA1163271A (fr)	1984-03-06	Acides, esters, thioesters et amides thioxanthone- carboxyliques, possedant des groups fonctionnels reactifs
US4506083A (en)	1985-03-19	Thioxanthonecarboxylic acid esters, thioesters and amides
US4378411A (en)	1983-03-29	Radiation-curable polymers
US4304705A (en)	1981-12-08	Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers
KR930007303B1 (ko)	1993-08-05	불포화계의 광중합용 광 개시제
CA1127792A (fr)	1982-07-13	Polymeres pouvant former a la lumiere des liens par reticulation croisee avec des groupements lateraux, tricycliques du type imidyles
GB2095248A (en)	1982-09-29	Thioxanthones for use as photopolymerization initiator or sensitiser
HK1004553A1 (en)	1998-11-27	Titanocenes, their use and n-substituted fluoroanilines
HK1004553B (en)	1998-11-27	Titanocenes, their use and n-substituted fluoroanilines
US4367324A (en)	1983-01-04	Photocrosslinkable polymers with thioxanthone and imidyl groupings in side chains
CA1166635A (fr)	1984-05-01	Acides thioxanthonecarboxyliques et derives de ces acides
CA1183639A (fr)	1985-03-05	Polyesters renfermant un groupe heterocyclique, reticulables par apport d'energie, et dispersables dans l'eau
JPS6356221B2 (fr)	1988-11-07
CA1180486A (fr)	1985-01-02	Polymeres possedant des radicaux thioxanthones comme chaines laterales
EP0075538B1 (fr)	1986-12-30	Composition polymérisable contenant des groupes carboxyliques
US4363917A (en)	1982-12-14	3,5-Disubstituted phthalic acid imides, phthalic acids and phthalic acid anhydrides
US4158618A (en)	1979-06-19	Actinic-radiation curable polymers prepared from a reactive polymer, halogenated cyclic anhydride and glycidyl ester
JP2573963B2 (ja)	1997-01-22	重合体である光増感剤
JPS60142990A (ja)	1985-07-29	新規なアクリル酸エステルおよびメタアクリル酸エステル
Nishikubo et al.	1993	Photochemical addition reaction of a polymer‐bearing pendant vinyl ether with various thiol compounds
US4463142A (en)	1984-07-31	Photocrosslinkable polymers with side groups derived from indenone and the preparation and use of these polymers
Gibson et al.	1979	Chemical modification of polymers. XI. Photoreactive polymers from poly (vinylbenzyl chloride)
JPH02273656A (ja)	1990-11-08	置換不飽和二反応性二環式イミド及びその用途
JPH08123028A (ja)	1996-05-17	フォトソルダーレジスト
JPS61197541A (ja)	1986-09-01	新規なアクリレ−ト化合物およびその製造法