AU718619B2 - Non-volatile phenylglyoxalic esters - Google Patents
Non-volatile phenylglyoxalic esters Download PDFInfo
- Publication number
- AU718619B2 AU718619B2 AU60963/98A AU6096398A AU718619B2 AU 718619 B2 AU718619 B2 AU 718619B2 AU 60963/98 A AU60963/98 A AU 60963/98A AU 6096398 A AU6096398 A AU 6096398A AU 718619 B2 AU718619 B2 AU 718619B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- alkyl
- alkoxy
- substituted
- hydrogen
- Prior art date
- 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.)
- Ceased
Links
- 150000002148 esters Chemical class 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims description 110
- -1 anthracyl Chemical group 0.000 claims description 100
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 238000000576 coating method Methods 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 239000011248 coating agent Substances 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 238000007639 printing Methods 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 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 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000002131 composite material Substances 0.000 claims description 9
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000003365 glass fiber Substances 0.000 claims description 8
- 239000000976 ink Substances 0.000 claims description 8
- 238000007650 screen-printing Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 230000033458 reproduction Effects 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 238000005538 encapsulation Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([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
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims 1
- 206010065042 Immune reconstitution inflammatory syndrome Diseases 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 17
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- 238000001723 curing Methods 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 9
- 229910052753 mercury Inorganic materials 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
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- 239000002023 wood Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 229940024874 benzophenone Drugs 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 4
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- 229920000515 polycarbonate Polymers 0.000 description 1
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
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- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Holo Graphy (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cosmetics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH19597 | 1997-01-30 | ||
| CH195/97 | 1997-01-30 | ||
| PCT/EP1998/000351 WO1998033761A1 (en) | 1997-01-30 | 1998-01-23 | Non-volatile phenylglyoxalic esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6096398A AU6096398A (en) | 1998-08-25 |
| AU718619B2 true AU718619B2 (en) | 2000-04-20 |
Family
ID=4181427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU60963/98A Ceased AU718619B2 (en) | 1997-01-30 | 1998-01-23 | Non-volatile phenylglyoxalic esters |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6048660A (enExample) |
| EP (1) | EP0956280B1 (enExample) |
| JP (1) | JP4171073B2 (enExample) |
| KR (1) | KR100548976B1 (enExample) |
| CN (1) | CN1157359C (enExample) |
| AU (1) | AU718619B2 (enExample) |
| BR (1) | BR9806940B1 (enExample) |
| CA (1) | CA2275667A1 (enExample) |
| DE (1) | DE69809029T2 (enExample) |
| DK (1) | DK0956280T3 (enExample) |
| ES (1) | ES2184233T3 (enExample) |
| TW (1) | TW460450B (enExample) |
| WO (1) | WO1998033761A1 (enExample) |
| ZA (1) | ZA98724B (enExample) |
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| CN1304353A (zh) * | 1999-03-09 | 2001-07-18 | 李·艾辛格 | 组织或图案表面在一种样品上的应用 |
| DE19913353A1 (de) * | 1999-03-24 | 2000-09-28 | Basf Ag | Verwendung von Phenylglyoxalsäureestern als Photoinitiatoren |
| TW557298B (en) * | 2000-08-14 | 2003-10-11 | Ciba Sc Holding Ag | A compound, a photopolymerizible composition, a process for producing coatings and a method for causing a photoinitiator to accumulate at the surface of coatings |
| TWI244495B (en) * | 2000-08-14 | 2005-12-01 | Ciba Sc Holding Ag | Process for producing coatings siloxane photoinitiators |
| US6470128B1 (en) | 2001-03-30 | 2002-10-22 | Alcatel | UV-curable coating composition for optical fiber for a fast cure and with improved adhesion to glass |
| KR100898877B1 (ko) * | 2002-02-04 | 2009-05-25 | 시바 홀딩 인크 | 고도로 플루오르화된 단량체 내의 플루오르화 광개시제 |
| AU2003208347A1 (en) * | 2002-02-04 | 2003-09-02 | Ciba Specialty Chemicals Holding Inc. | Surface-active photoinitiators |
| DE60322345D1 (en) * | 2002-02-04 | 2008-09-04 | Ciba Holding Inc | Oberflächenaktive siloxanphotoinitiatoren |
| CA2483004A1 (en) * | 2002-04-26 | 2003-11-06 | Ciba Specialty Chemicals Holding Inc. | Incorporable photoinitiator |
| DE10241299A1 (de) | 2002-09-04 | 2004-03-25 | Basf Ag | Strahlungshärtbare Polyurethane mit verkappten Aminogrupppen |
| US7285363B2 (en) * | 2002-11-08 | 2007-10-23 | The University Of Connecticut | Photoactivators, methods of use, and the articles derived therefrom |
| JP4116890B2 (ja) * | 2003-01-31 | 2008-07-09 | 富士フイルム株式会社 | インクジェット記録用インクおよび画像形成方法 |
| JP2004231863A (ja) * | 2003-01-31 | 2004-08-19 | Fuji Photo Film Co Ltd | インクジェット記録用インクおよび画像形成方法 |
| DE10316890A1 (de) * | 2003-04-12 | 2004-11-04 | Basf Coatings Ag | Mit aktinischer Strahlung aktivierbare Initiatoren enthaltende Mischungen sowie Zwei- und Mehrkomponentensysteme, Verfahren zu ihrer Herstellung und ihre Verwendung |
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| US7309550B2 (en) * | 2004-09-20 | 2007-12-18 | Chemence, Inc. | Photosensitive composition with low yellowing under UV-light and sunlight exposure |
| WO2006067061A2 (en) * | 2004-12-22 | 2006-06-29 | Ciba Specialty Chemicals Holding Inc. | Process for the production of strongly adherent coatings |
| DE102004063102A1 (de) | 2004-12-22 | 2006-07-13 | Basf Ag | Strahlungshärtbare Verbindungen |
| US8048937B2 (en) | 2005-02-24 | 2011-11-01 | Basf Aktiengesellschaft | Radiation-curable aqueous polyurethane dispersions |
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| ITVA20050032A1 (it) * | 2005-05-13 | 2006-11-14 | Lamberti Spa | Esteri fenilgliossilici generanti residui a bassa migrabilita' e odore |
| ITVA20050049A1 (it) * | 2005-08-05 | 2007-02-06 | Lamberti Spa | Sistemi fotopolimerizzabili contenenti coiniziatori a bassa estraibilita' e volatilita' |
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| US5795581A (en) * | 1995-03-31 | 1998-08-18 | Sandia Corporation | Controlled release of molecular components of dendrimer/bioactive complexes |
-
1998
- 1998-01-23 AU AU60963/98A patent/AU718619B2/en not_active Ceased
- 1998-01-23 ES ES98905335T patent/ES2184233T3/es not_active Expired - Lifetime
- 1998-01-23 EP EP98905335A patent/EP0956280B1/en not_active Expired - Lifetime
- 1998-01-23 WO PCT/EP1998/000351 patent/WO1998033761A1/en not_active Ceased
- 1998-01-23 KR KR1019997006856A patent/KR100548976B1/ko not_active Expired - Fee Related
- 1998-01-23 DK DK98905335T patent/DK0956280T3/da active
- 1998-01-23 JP JP53250998A patent/JP4171073B2/ja not_active Expired - Lifetime
- 1998-01-23 CN CNB98801985XA patent/CN1157359C/zh not_active Expired - Lifetime
- 1998-01-23 CA CA002275667A patent/CA2275667A1/en not_active Abandoned
- 1998-01-23 TW TW087100902A patent/TW460450B/zh active
- 1998-01-23 DE DE69809029T patent/DE69809029T2/de not_active Expired - Lifetime
- 1998-01-23 BR BRPI9806940-3A patent/BR9806940B1/pt not_active IP Right Cessation
- 1998-01-28 US US09/014,555 patent/US6048660A/en not_active Expired - Lifetime
- 1998-01-29 ZA ZA98724A patent/ZA98724B/xx unknown
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| Publication number | Publication date |
|---|---|
| EP0956280A1 (en) | 1999-11-17 |
| KR20000070608A (ko) | 2000-11-25 |
| BR9806940A (pt) | 2000-03-28 |
| US6048660A (en) | 2000-04-11 |
| JP2001511137A (ja) | 2001-08-07 |
| ZA98724B (en) | 1998-07-30 |
| DE69809029D1 (de) | 2002-12-05 |
| DK0956280T3 (da) | 2003-02-24 |
| TW460450B (en) | 2001-10-21 |
| CN1244190A (zh) | 2000-02-09 |
| AU6096398A (en) | 1998-08-25 |
| WO1998033761A1 (en) | 1998-08-06 |
| ES2184233T3 (es) | 2003-04-01 |
| CN1157359C (zh) | 2004-07-14 |
| EP0956280B1 (en) | 2002-10-30 |
| CA2275667A1 (en) | 1998-08-06 |
| DE69809029T2 (de) | 2003-06-05 |
| BR9806940B1 (pt) | 2010-12-14 |
| KR100548976B1 (ko) | 2006-02-03 |
| JP4171073B2 (ja) | 2008-10-22 |
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