CN101906095A - 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 - Google Patents
噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 Download PDFInfo
- Publication number
- CN101906095A CN101906095A CN 201010218422 CN201010218422A CN101906095A CN 101906095 A CN101906095 A CN 101906095A CN 201010218422 CN201010218422 CN 201010218422 CN 201010218422 A CN201010218422 A CN 201010218422A CN 101906095 A CN101906095 A CN 101906095A
- Authority
- CN
- China
- Prior art keywords
- thioxanthone
- acid
- carboxylicesters
- compound
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 20
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 18
- -1 isocyanide ester Chemical class 0.000 claims description 15
- 239000000976 ink Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 238000007639 printing Methods 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 claims description 4
- JWWZLQALVWCRLX-UHFFFAOYSA-N 3-(2-carboxyphenyl)thiophene-2-carboxylic acid Chemical compound C(=O)(O)C=1SC=CC=1C1=C(C(=O)O)C=CC=C1 JWWZLQALVWCRLX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 210000003298 dental enamel Anatomy 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000002966 varnish Substances 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 claims description 2
- HSWKIPCBJSMQFA-UHFFFAOYSA-N 1-butoxybutane;tin Chemical compound [Sn].CCCCOCCCC HSWKIPCBJSMQFA-UHFFFAOYSA-N 0.000 claims description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- 239000012972 dimethylethanolamine Substances 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007650 screen-printing Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 238000013508 migration Methods 0.000 abstract description 10
- 230000005012 migration Effects 0.000 abstract description 10
- 235000013305 food Nutrition 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 238000012856 packing Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 238000010792 warming Methods 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 229960003511 macrogol Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ANHLDZMOXDYFMQ-UHFFFAOYSA-N 2-hydroxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC=C3SC2=C1 ANHLDZMOXDYFMQ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IKVYHNPVKUNCJM-UHFFFAOYSA-N 4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2 IKVYHNPVKUNCJM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009933 burial Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000009512 pharmaceutical packaging Methods 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000001671 psychotherapy Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyethers (AREA)
Abstract
Description
引发剂 | 气相挥发到活性炭吸附(mg/m2) |
ITX | 6.1 |
Ia | <0.05 |
光引发剂 | 与纸的接触迁移(mg/m2) |
ITX | 1.58 |
化合物Ia | 0.04 |
Claims (10)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010218422 CN101906095B (zh) | 2010-07-06 | 2010-07-06 | 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 |
EP10782170.4A EP2592074A1 (en) | 2010-07-06 | 2010-07-16 | Thioxanthone-4-carboxylates, their preparation methods, photoinitiator compositions and uses thereof |
KR1020107025188A KR20130043254A (ko) | 2010-07-06 | 2010-07-16 | 치오산톤-4-카르복시산 에스테르 및 그 제조방법과 광개시제 혼합물 및 그 응용 |
JP2013516955A JP2013530994A (ja) | 2010-07-06 | 2010-07-16 | チオキサントン−4−カルボン酸エステル及び製造方法並びに光開始剤組成物及び応用 |
PCT/CN2010/075209 WO2012003644A1 (zh) | 2010-07-06 | 2010-07-16 | 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010218422 CN101906095B (zh) | 2010-07-06 | 2010-07-06 | 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101906095A true CN101906095A (zh) | 2010-12-08 |
CN101906095B CN101906095B (zh) | 2013-08-14 |
Family
ID=43261705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201010218422 Active CN101906095B (zh) | 2010-07-06 | 2010-07-06 | 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2592074A1 (zh) |
JP (1) | JP2013530994A (zh) |
KR (1) | KR20130043254A (zh) |
CN (1) | CN101906095B (zh) |
WO (1) | WO2012003644A1 (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012003644A1 (zh) * | 2010-07-06 | 2012-01-12 | 天津久日化学工业有限公司 | 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 |
CN104892798A (zh) * | 2015-06-23 | 2015-09-09 | 天津久日化学股份有限公司 | 一种新的噻吨酮类光引发剂及在uv-led光固化的应用 |
CN104910131A (zh) * | 2015-06-23 | 2015-09-16 | 天津久日化学股份有限公司 | 一种新的噻吨酮羧酸酯光引发剂及其制备方法 |
CN106349213A (zh) * | 2016-08-29 | 2017-01-25 | 天津久日新材料股份有限公司 | 一种自供氢型光引发剂及其制备方法 |
CN106366755A (zh) * | 2016-08-31 | 2017-02-01 | 天津久日新材料股份有限公司 | 用于食品、药品以及化妆品包装的光固化油墨组合物 |
CN107207887A (zh) * | 2015-01-27 | 2017-09-26 | 惠普发展公司,有限责任合伙企业 | 聚合物光活性剂 |
CN109928951A (zh) * | 2017-12-19 | 2019-06-25 | 山东久日化学科技有限公司 | 2-异丙基硫杂蒽酮的制备方法 |
CN110845376A (zh) * | 2019-11-25 | 2020-02-28 | 山东益丰生化环保股份有限公司 | 一种季戊四醇巯基羧酸酯的制备方法 |
CN112457434A (zh) * | 2020-09-25 | 2021-03-09 | 苏州润邦半导体材料科技有限公司 | 纳米晶体复合材料及其制备方法与用途 |
Families Citing this family (7)
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---|---|---|---|---|
KR101684502B1 (ko) | 2013-11-22 | 2016-12-08 | 현대자동차 주식회사 | 배기 가스 정화 장치 및 배기 가스 정화 방법 |
US10414927B2 (en) | 2015-01-27 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric photo active agents |
US10619007B2 (en) | 2015-01-27 | 2020-04-14 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergists |
US10414862B2 (en) | 2015-07-09 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergist |
CN111699204B (zh) | 2018-02-16 | 2023-07-21 | 株式会社Adeka | 自由基聚合引发剂、含有其的组合物、其固化物、其制造方法和化合物 |
CN114752004B (zh) * | 2022-05-11 | 2023-07-04 | 杭州师范大学 | 一种生物基uv固化引发剂的制备方法及其产品和应用 |
EP4385982A1 (en) | 2022-12-16 | 2024-06-19 | Henkel AG & Co. KGaA | Method of preparing a monomeric photoinitiator |
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WO2012003644A1 (zh) * | 2010-07-06 | 2012-01-12 | 天津久日化学工业有限公司 | 噻吨酮-4-羧酸酯及制备方法和光引发剂组合物与应用 |
CN107207887B (zh) * | 2015-01-27 | 2021-03-12 | 惠普发展公司,有限责任合伙企业 | 聚合物光活性剂 |
CN107207887A (zh) * | 2015-01-27 | 2017-09-26 | 惠普发展公司,有限责任合伙企业 | 聚合物光活性剂 |
CN104910131B (zh) * | 2015-06-23 | 2018-01-02 | 天津久日新材料股份有限公司 | 一种噻吨酮羧酸酯光引发剂及其制备方法 |
CN104892798A (zh) * | 2015-06-23 | 2015-09-09 | 天津久日化学股份有限公司 | 一种新的噻吨酮类光引发剂及在uv-led光固化的应用 |
CN104910131A (zh) * | 2015-06-23 | 2015-09-16 | 天津久日化学股份有限公司 | 一种新的噻吨酮羧酸酯光引发剂及其制备方法 |
CN106349213A (zh) * | 2016-08-29 | 2017-01-25 | 天津久日新材料股份有限公司 | 一种自供氢型光引发剂及其制备方法 |
CN106366755A (zh) * | 2016-08-31 | 2017-02-01 | 天津久日新材料股份有限公司 | 用于食品、药品以及化妆品包装的光固化油墨组合物 |
CN109928951A (zh) * | 2017-12-19 | 2019-06-25 | 山东久日化学科技有限公司 | 2-异丙基硫杂蒽酮的制备方法 |
CN109928951B (zh) * | 2017-12-19 | 2022-03-08 | 山东久日化学科技有限公司 | 2-异丙基硫杂蒽酮的制备方法 |
CN110845376A (zh) * | 2019-11-25 | 2020-02-28 | 山东益丰生化环保股份有限公司 | 一种季戊四醇巯基羧酸酯的制备方法 |
CN110845376B (zh) * | 2019-11-25 | 2022-01-04 | 益丰新材料股份有限公司 | 一种季戊四醇巯基羧酸酯的制备方法 |
CN112457434A (zh) * | 2020-09-25 | 2021-03-09 | 苏州润邦半导体材料科技有限公司 | 纳米晶体复合材料及其制备方法与用途 |
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KR20130043254A (ko) | 2013-04-30 |
CN101906095B (zh) | 2013-08-14 |
JP2013530994A (ja) | 2013-08-01 |
EP2592074A1 (en) | 2013-05-15 |
WO2012003644A1 (zh) | 2012-01-12 |
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