CN113444017A - 一种二苯硫醚酮肟酯化合物、制备方法、组合物及用途 - Google Patents
一种二苯硫醚酮肟酯化合物、制备方法、组合物及用途 Download PDFInfo
- Publication number
- CN113444017A CN113444017A CN202010222098.0A CN202010222098A CN113444017A CN 113444017 A CN113444017 A CN 113444017A CN 202010222098 A CN202010222098 A CN 202010222098A CN 113444017 A CN113444017 A CN 113444017A
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- China
- Prior art keywords
- compound
- group
- phenyl
- alkyl
- aryl
- Prior art date
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- -1 Diphenyl sulfide ether ketone oxime ester compound Chemical class 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002202 Polyethylene glycol Chemical group 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920001223 polyethylene glycol Chemical group 0.000 claims description 2
- 125000003892 C18 acyl group Chemical group 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 abstract description 6
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 238000009472 formulation Methods 0.000 abstract description 2
- 229940124543 ultraviolet light absorber Drugs 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 7
- BBAVLSGPJLTUPP-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C(C=C2)=CC=C2OC)=O)C=C1)=O)=NOC(C)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C(C=C2)=CC=C2OC)=O)C=C1)=O)=NOC(C)=O BBAVLSGPJLTUPP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JPLAAIVTHVREOT-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=C(C2(C=CC(C=CC#N)=CC2)N(C)C)C=CC=C1)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=C(C2(C=CC(C=CC#N)=CC2)N(C)C)C=CC=C1)=O)=NOC(C1=CC=CC=C1)=O JPLAAIVTHVREOT-UHFFFAOYSA-N 0.000 description 5
- ZGJKTVMETAVPBH-UHFFFAOYSA-N CCCCCCCCC(C=C1)=CC=C1SC1=CC=C(C=C(C(OC)=O)C(OC)=O)C=C1 Chemical compound CCCCCCCCC(C=C1)=CC=C1SC1=CC=C(C=C(C(OC)=O)C(OC)=O)C=C1 ZGJKTVMETAVPBH-UHFFFAOYSA-N 0.000 description 5
- PUSQTJHHLJJDAR-UHFFFAOYSA-N COC(C(C(OC)=O)=CC(C=C1)=CC=C1SC1=CC=CC=C1)=O Chemical compound COC(C(C(OC)=O)=CC(C=C1)=CC=C1SC1=CC=CC=C1)=O PUSQTJHHLJJDAR-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- OMOFPPRFFFPSQP-UHFFFAOYSA-N 1-phenyl-3-(4-phenylsulfanylphenyl)prop-2-en-1-one Chemical compound C1(=CC=CC=C1)SC1=CC=C(C=C1)C=CC(=O)C1=CC=CC=C1 OMOFPPRFFFPSQP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VDNBWBPUFMZCEW-UHFFFAOYSA-N 4-phenylsulfanylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1SC1=CC=CC=C1 VDNBWBPUFMZCEW-UHFFFAOYSA-N 0.000 description 4
- DXQZWVVPMBAKSL-UHFFFAOYSA-N CCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NO Chemical compound CCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NO DXQZWVVPMBAKSL-UHFFFAOYSA-N 0.000 description 4
- BUBRVKDNSHPZOR-UHFFFAOYSA-N CCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NOC(C)=O Chemical compound CCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NOC(C)=O BUBRVKDNSHPZOR-UHFFFAOYSA-N 0.000 description 4
- CXPLJDRBCXDEST-UHFFFAOYSA-N CCCC(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O Chemical compound CCCC(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O CXPLJDRBCXDEST-UHFFFAOYSA-N 0.000 description 4
- FUDGRCHUTQZGMO-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC(C=C1)=CC=C1C(C(C=C1)=CC=C1N(C)C)=C(C#N)C#N)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC(C=C1)=CC=C1C(C(C=C1)=CC=C1N(C)C)=C(C#N)C#N)=O)=NOC(C1=CC=CC=C1)=O FUDGRCHUTQZGMO-UHFFFAOYSA-N 0.000 description 4
- YEIFJRJUEPKXBH-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC(C=C1)=CC=C1C(C1=CC=CC=C1)=C(C(OCC)=O)C#N)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC(C=C1)=CC=C1C(C1=CC=CC=C1)=C(C(OCC)=O)C#N)=O)=NOC(C1=CC=CC=C1)=O YEIFJRJUEPKXBH-UHFFFAOYSA-N 0.000 description 4
- YQFPGGFILLACHW-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=C(C(OC)=O)C(OC)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=C(C(OC)=O)C(OC)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O YQFPGGFILLACHW-UHFFFAOYSA-N 0.000 description 4
- RZGFZBRSYXGSBK-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=C(C(OCC)=O)C#N)C=C1)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=C(C(OCC)=O)C#N)C=C1)=O)=NOC(C1=CC=CC=C1)=O RZGFZBRSYXGSBK-UHFFFAOYSA-N 0.000 description 4
- IFDFAPBINRCVCE-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=C(C=NOC(C2=CC=CC=C2)=O)C#N)C=C1)=O)=NOC(C)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=C(C=NOC(C2=CC=CC=C2)=O)C#N)C=C1)=O)=NOC(C)=O IFDFAPBINRCVCE-UHFFFAOYSA-N 0.000 description 4
- DZOVFYQJWNPLSQ-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C(C=C2)=CC=C2N(C)C)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C(C=C2)=CC=C2N(C)C)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O DZOVFYQJWNPLSQ-UHFFFAOYSA-N 0.000 description 4
- IWMXERFNJDLQST-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NOC(C)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NOC(C)=O IWMXERFNJDLQST-UHFFFAOYSA-N 0.000 description 4
- QAPUPVMBLXXYQJ-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O QAPUPVMBLXXYQJ-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WCLLKPBGAXAVQE-UHFFFAOYSA-N CC(ON=C(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)C1=CC=CC=C1)=O Chemical compound CC(ON=C(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=CC=CC=C2)=O)C=C1)=O)C1=CC=CC=C1)=O WCLLKPBGAXAVQE-UHFFFAOYSA-N 0.000 description 3
- LUNGLRMSGGQPDH-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C(C=CC=C2)=C2Cl)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C(C=CC=C2)=C2Cl)=O)C=C1)=O)=NOC(C1=CC=CC=C1)=O LUNGLRMSGGQPDH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical group CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 description 2
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 2
- QQBDOJUNCZSRGA-UHFFFAOYSA-N phenyl-(4-phenylsulfanylphenyl)methanone Chemical group C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 QQBDOJUNCZSRGA-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- XUDYHODVSUXRPW-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1SC1=CC=CC=C1 XUDYHODVSUXRPW-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- YXWWHNCQZBVZPV-UHFFFAOYSA-N 2'-methylacetophenone Chemical compound CC(=O)C1=CC=CC=C1C YXWWHNCQZBVZPV-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- PYKKCPQFYNZYOB-UHFFFAOYSA-N 2-(4-phenylsulfanylphenyl)acetonitrile Chemical compound C1=CC(CC#N)=CC=C1SC1=CC=CC=C1 PYKKCPQFYNZYOB-UHFFFAOYSA-N 0.000 description 1
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical group ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- ZMMOYIXZGHJMNI-UHFFFAOYSA-N 3-oxopropanenitrile Chemical compound O=CCC#N ZMMOYIXZGHJMNI-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- SHUQJJLPHJTLPI-UHFFFAOYSA-N CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=C(C)C=CC=C2)=O)C=C1)=O)=NOC(C)=O Chemical compound CCCCCCC(C(C(C=C1)=CC=C1SC1=CC=C(C=CC(C2=C(C)C=CC=C2)=O)C=C1)=O)=NOC(C)=O SHUQJJLPHJTLPI-UHFFFAOYSA-N 0.000 description 1
- FKGGSUMWBCPFCE-UHFFFAOYSA-N CN(C)C(C=C1)=CC=C1C(C(C=C1)=CC=C1SC1=CC=CC=C1)=O Chemical compound CN(C)C(C=C1)=CC=C1C(C(C=C1)=CC=C1SC1=CC=CC=C1)=O FKGGSUMWBCPFCE-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical group N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/68—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with at least one of the esterifying carboxyl groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- 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
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- G—PHYSICS
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Abstract
本发明公开了一种二苯硫醚酮肟酯化合物、制备方法、组合物及用途,二苯硫醚酮肟酯光引发剂具有高敏感度、可吸收长波长的光线的特点。一方面,吸收长波长光线可增加深层固化,另一方面,也可避免配方中其他较短波长紫外光吸收剂与本发明光引发剂竞争入射光线。本发明化合物具有长波长波段的引发能力,可以单独使用或与其他的光引发剂搭配使用。
Description
技术领域
本发明涉及一种二苯硫醚酮肟酯化合物、制备方法、组合物及用途。本发明的二苯硫醚酮肟酯化合物,其用于光固化、光学或电子产业。
背景技术
光引发剂是光固化产业,例如涂料、油墨、粘合剂、光刻胶等领域中重要的化学品。光固化材料单体,必需添加光引发剂才能够在一定波长的光源照射下,激发光固化材料中的不饱和基团发生聚合反应,并引起光固化材料的固化。良好的光引发剂是光固化技术成功的关键所在。传统光引发剂包括安息香类、苯乙酮类、二苯甲酮类、硫杂蒽酮类、酰基氧化膦类、芳香重氮盐类、二茂铁类、三氮嗪类、六芳基二咪唑类及肟酯类等。其中肟酯类出现对于光引发产业产生了大幅的进步,例如二苯硫醚酮肟酯OXE-01,特别受重视。
通常固化配方中常添加蓝、紫外光吸收剂,例如Tinuvin 400或TiO2,以保护固化后的树脂受光照射而降解,其吸收紫外光波长达到400nm或更长。蓝、紫外光吸收剂也添加于透镜以保护眼睛。这些蓝光-紫外光吸收剂会和光引发剂竞争入射光,造成引发能力下降。OXE-01二苯硫醚酮肟酯类光引发剂虽然吸收较长波长光线,但仍受影响。
因此,增长现有二苯硫醚酮肟酯类光引发剂吸收的波长,一直是产业努力目标。
发明内容
目的:为解决现有技术的不足,本发明提供一种二苯硫醚酮肟酯化合物、制备方法、组合物及用途。本发明二苯硫醚酮肟酯光引发剂在长波长的吸收范围,具有深层固化能力。另一方面,本发明二苯硫醚酮肟酯光引发剂因具有较长波长的吸收范围,可避免配方中其他紫外线或蓝光吸收剂,竞争入射的激发光。
因此,本发明化合物在长波长波段的引发能力较强,可以单独使用或与其他光引发剂搭配使用。
技术方案:为解决上述技术问题,本发明采用的技术方案为:
第一方面,提供一种式(I)化合物或其盐,
其中,
R1~R2各自独立地自氢、含取代或未经取代的C1~C18烷基,较佳地,C1~C8烷基,更佳地,C1~C6烷基、取代或未经取代的C1~C18烯基,较佳地,C1~C8烯基,更佳地,C1~C6烯基、C1~C18烷氧基,较佳地,C1~C8烷氧基,更佳地,C1~C6烷氧基、较佳地,取代或未经取代的C1~C18芳基,更佳地,C1-C6芳基;
R6~R9各自独立地选自氢、聚乙二醇基、含取代或未经取代的C1~C18烷基,较佳地,C1~C8烷基,更佳地,C1~C6烷基、取代或未经取代的C1~C18烯基,较佳地,C1~C8烯基,更佳地,C1~C6烯基、C1~C18烷氧基,较佳地C1~C8烷氧基,更佳地,C1~C6烷氧、取代或未经取代的C1~C18芳基,较佳地,C1~C12烯基,更佳地,C1~C6芳基;
R10选自氢、羟基、氧基、硫基、卤素、氨基、硝基、亚硝基、氰基、羧基、含1~18个碳的烷基、烯基、芳基、杂环基、羰基、酰基、酯基、烷基胺基、烷氧基、烷硫基、芳基烷基、杂环基烷基、芳基烯基、杂环基烯基,较佳地,含C1~C8的烷基、烯基、芳基、杂环基、羰基、酰基、酯基、烷基胺基、烷氧基、烷硫基、芳基烷基、杂环基烷基、芳基烯基、杂环基烯基,更佳地,含1-6个碳的烷基、烯基、芳基、杂环基、羰基、酰基、酯基、烷基胺基、烷氧基、烷硫基、芳基烷基、杂环基烷基、芳基烯基、杂环基烯基。
m=0~2,较佳地,m=0~1。
较佳地,R3、R4之一是
较佳地,R3、R4之一是
较佳地,R3~R4相异或相同,选自C1~C6烷基、COOR6、CONR7R8、COR9、CN。更佳地,R3~R4二者相同,选自COOR6、CONR7R8、COR9、CN,特佳地,R3~R4二者相同,选自COOR6,特佳地,R3~R4二者相异,选自COOR6、CN,,特佳地,R3~R4二者相异,选自COOR6、CN、
较佳地,R10选自氢、羟基、氧基、硫基、卤素、氨基、硝基、亚硝基、氰基、羧基、含1~6个碳的烷基、烯基、羰基、酯基、烷基胺基、烷氧基、芳基。
最佳地,本发明化合物,包括以下:
第二方面,提供所述的式(I)化合物的制备方法,包括:
其中,R1~R5如上所定义。
其中,R2~R5如上所定义;
A是肟化试剂,包括盐酸羟胺或亚硝酸酯类,较佳地,包括亚硝酸异丙酯。
第三方面,本发明提供一种组合物,包括至少一种式(I)中化合物或其盐、各种单体或预聚物。式(I)化合物或其盐、组合物可用于光引发、光吸收、光敏或感光剂。本发明组合物,可包括供氢体、光敏剂、或各种稳定剂。
具体实施方式
下面结合实施例对本发明作进一步描述。以下实施例只是用于更加清楚地说明本发明的性能,而不能仅局限于下面的实施例。
在一些实施例中,本发明式(I)化合物的制备方法,主要特征包括以下反应式,例如实施例1~11:
式(I)化合物的制备方法,例如实施例12~19:
式(I)化合物的制备方法,例如实施例20~21:
式(I)化合物的制备方法,例如实施例22:
其中,R1~R5如上所定义,R11定义为C1~C18烷基、烯基、烷氧基、芳基、烷基酰基、芳基酰基等,较佳地,R11为C1~C10烷基、烷基酰基、或芳基酰基。
实施例1
1-苯基-3-(4-(苯硫基)苯基)丙-2-烯-1-酮(1)
1.1g KOH、50mL甲醇、和1.5g苯乙酮混合,加入2.2g的4-(苯硫基)苯甲醛(熔点53℃),加热至回流,反应4h,减压回收溶剂,经硅胶柱层析,得到化合物(1)。MS[M]+316.1。1H-NMR 8.0新生成峰代表反应完成(O=C-CH=CH-Ph)。
实施例2
1-(4-((4-(3-氧代-3-苯基丙-1-烯-1-基)苯基)硫代)苯基)丁-1-酮(2)
1000ml的反应瓶中加入90g无水三氯化铝、171g二苯硫醚、580g二氯乙烷,保持10℃,慢慢滴加66g丁酰氯和45g二氯乙烷。加毕,保持10℃反应30分钟,取样分析。加至水中,10℃左右搅拌30分钟,再用水洗涤三次至PH=6,水洗温度10℃,蒸馏,得到化合物(2)。MS[M]+386.1。1H-NMR 3.0(triplet)新生成峰代表反应完成(O=CCH2 CH2CH3)
实施例3
2-(羟基亚氨基)-1-(4-((4-(3-氧代-3-苯基丙-1-烯-1-基)苯基)硫基)苯基)丁-1-酮(3)
500ml的反应瓶中加入27g化合物(2),160g四氢呋喃搅拌,8g浓盐酸。常温下滴加8g亚硝酸异丙酯,1小时加完,常温反应0.2小时,取样分析。调PH值到中性,搅拌25分钟。固体再用水洗2次,水洗好的固体用乙醇精制,60℃烘干,得化合物(3)。实例2中化合物(2)1H-NMR,化学位移3.0峰消失,及13C-NMR,154.0新生成峰(C=N)代表反应完成。
实施例4
2-(乙酰氧基亚氨基)-1-(4-((4-(3-氧代-3-苯基丙-1-烯-1-基)苯基)硫基)苯基)丁-1-酮(4)
250mL烧瓶中加入2.3g化合物(3),50g二氯乙烷,搅拌溶解后,冷却至0~5℃,加入1g三乙胺,保持温度0~5℃,滴加乙酰氯的四氢呋喃溶液(由0.8g乙酰氯和3g四氢呋喃组成),10分钟加完,保持0~5℃反应3小时。加水,搅拌水解10分钟,过滤,滤饼水洗3次。得到化合物(4)。MS[M]+457.1。
实施例5
2-(乙酰氧基亚氨基)-1-(4-((4-(3-氧代-3-苯基丙-1-烯-1-基)苯基)硫基)苯基)辛烷-1-酮(5)
根据实施例1-4方法,但以正辛酰氯代替正丁酰氯,得到化合物(5)。Ms[M]+513.2。
实施例6
3-(4-((4-(2-(乙酰氧基亚氨基)-2-苯基乙酰基)苯基)硫基)苯基)-1-苯基丙-2-烯-1-酮(6)
根据实施例1-4方法,但以苯乙酰氯代替正丁酰氯,得到化合物(6)。MS[M]+505.1。
实施例7
2-((苯甲酰氧基)亚氨基)-1-(4-((4-(3-氧代-3-苯基丙-1-烯-1-基)苯基)硫基)苯基)辛烷-1-酮(7)
根据实施例5方法,但以苯甲酰氯代替乙酰氯,得到化合物(7)。MS[M]+575.2。
实施例8
2-(苯甲酰氧基亚氨基)-1-(4-((4-(3-(4-(二甲氨基)苯基)-3-氧代丙-1-烯-1-基)苯基)硫代基)苯基)辛烷-1-酮(8)
根据实施例7方法,但以4-二甲基胺基-苯乙酮代替苯乙酮,得到化合物(8)。MS[M]+618.3。
实施例9
2-(乙酰氧基亚氨基)-1-(4-((4-(3-(4-(甲氧基)苯基)-3-氧代丙-1-烯-1-基)苯基)硫代基)苯基)辛烷-1-酮(9)
根据实施例6方法,但以4-甲氧基-苯乙酮代替苯乙酮,得到化合物(9)。MS[M]+543.2。
实施例10
2-(乙酰氧基亚氨基)-1-(4-((4-(3-(2-(甲基)苯基)-3-氧代丙-1-烯-1-基)苯基)硫代基)苯基)辛烷-1-酮(9)
根据实施例5方法,但以2-甲基-苯乙酮代替苯乙酮,得到化合物(9)。MS[M]+527.2。
实施例11
2-(苯甲酰氧基亚氨基)-1-(4-((4-(3-(2-(氯)苯基)-3-氧代丙-1-烯-1-基)苯基)硫代基)苯基)辛烷-1-酮(11)
根据实施例7方法,但以2-氯-苯乙酮代替苯乙酮,得到化合物(10)。MS[M]+609.2。
实施例12
2-(4-(苯硫基)亚苄基)丙二酸二甲酯(12)
将21.5g的4-(苯硫基)苯甲醛及及14.5g丙二酸二甲酯溶解于二氯乙烷搅拌之。加入1mL哌啶和0.6mL醋酸,并加热回流脱水反应2小时。反应完成后除去溶剂,酸洗、干燥后得到化合物(12)。1H-NMR,8.3新生成峰代表反应完成(=CH-Ph)。
实施例13
2-(4-((4-辛酰基苯基)硫代)亚苄基)丙二酸二甲酯(13)
根据实施例2方法,但以化合物(12)代替化合物(1),正辛酰氯代替正丁酰氯。得到得到化合物(13)。MS[M]+454.2。
实施例14
2-(4-((4-(2-(羟基亚氨基)辛酰基)苯基)硫代)亚苄基)丙二酸二甲酯(14)
根据实施例3方法,但以化合物(13)代替化合物(2)。得到得到化合物(14)。13C-NMR化学位移154.0新生成峰(C=N)代表反应完成。
实施例15
2-(4-((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)亚苄基)丙二酸二甲酯(15)
根据实施例7方法,但以化合物(14)代替化合物(3)。得到得到化合物(15)。MS[M]+587.2。
实施例16
3-(4-((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)苯基)-2-氰基丙烯酸乙酯(16)
根据实施例15方法,但以2-氰基乙酸乙酯代替丙二酸二甲酯,得到化合物(16)。MS[M]+568.2。
实施例17
2-((苯甲酰氧基亚氨基)甲基)-3-(4-((4-(2-(乙酰氧基亚氨基)辛酰基)苯基)硫基)苯基)丙烯腈的混合物(17)
根据实施例15方法,但以3-氧代丙烷腈代替丙二酸二甲酯,经硅胶柱层析,得到化合物(17)混合物。
实施例18
2-(1-(4-((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)苯基)亚乙基)丙二酸二甲酯(18)
根据实施例15方法,但以1-(4-(苯硫基)苯基)乙-1-酮(熔点60℃)代替4-(苯硫基)苯甲醛,经硅胶柱层析,得到化合物(18)混合物。
实施例19
3-(4-((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)苯基)-2-氰基-3-苯基丙烯酸乙酯(19)
根据实施例16方法,但以苯基-(4-苯硫基-苯基)甲酮(熔点71℃)代替4-(苯硫基)苯甲醛,经硅胶柱层析,得到化合物(19)。MS[M]+644.2。
实施例20
3-(4-(((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)苯基)-2-氰基-3-(4-(二甲基氨基)苯基)丙烯酸乙酯(20)
根据实施例19方法,但以(4-(二甲氨基)苯基)(4-(苯硫基)苯基)甲酮代替苯基-(4-苯硫基-苯基)甲酮,经硅胶柱层析,得到化合物(20)。MS[M]+687.3。
实施例21
2-((4-((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)苯基)(4-(二甲基氨基)苯基)亚甲基)丙二腈(21)
根据实施例20方法,但以丙二腈代替2-氰基乙酸乙酯,经硅胶柱层析,得到化合物(21)。MS[M]+640.3。
实施例22
2-(4-(((4-(2-(苯甲酰氧基亚氨基)辛酰基)苯基)硫代)苯基)-3-(4-(二甲基氨基)苯基)丙烯腈(22)
根据实施例15方法,但以4-(二甲基氨基)苯甲醛,和2-(4-(苯硫基)苯基)乙腈进行反应,经硅胶柱层析,得到化合物(22)。
实施例23
预聚合组合物,包括0.05%的光引发剂(对照组OXE-01化合物或实例化合物),0.5mL甲基丙烯酸甲酯。样品中加入或不加入抗蓝光剂Eusorb 1990。并通过用氮气吹扫除脱氧气。用420-450nm光线进行聚合。聚合完成后,蒸发剩余的单体,称重剩余固体重。剩余重量越多表示光引发剂的聚合能力愈强。表1测试结果,+号表示光引发剂的引发能力,+号愈多表示光引发剂的引发能力愈强。结果显示,实例化合物在420nm以上,单独使用或与OXE-01搭配,引发能力较OXE-01强。
表1测试结果
以上已以较佳实施例公开了本发明,然其并非用以限制本发明,凡采用等同替换或者等效变换方式所获得的技术方案,均落在本发明的保护范围之内。
Claims (10)
1.一种式(I)化合物或其盐,
其中,
R1、R2各自独立地自氢、含C1~C18的经取代或未经取代的烷基、烯基、烷氧基、芳基;
R6、R7、R8、R9各自独立地选自氢、聚乙二醇基、C1~C18烷基、C1~C18烯基、C1~C18芳基;
R10选自氢、羟基、氧基、硫基、卤素、氨基、硝基、亚硝基、氰基、羧基、含C1~C18的烷基、C1~C18的烯基、C1~C18的芳基、C1~C18的杂环基、C1~C18的羰基、C1~C18的酰基、C1~C18的酯基、C1~C18的烷基胺基、C1~C18的烷氧基、C1~C18的烷硫基、C1~C18的芳基烷基、C1~C18的杂环基烷基、C1~C18的芳基烯基、C1~C18的杂环基烯基;
m=0~2。
2.根据权利要求1所述的化合物,其特征在于,R1、R2各自独立地选自氢、经取代或未经取代C1~C8的烷基、R10取代的苯基。
6.根据权利要求5所述的化合物,其特征在于,R10选自氢、羟基、氧基、硫基、卤素、氨基、硝基、亚硝基、氰基、羧基、含C1~C6的烷基、C1~C6的烯基、C1~C6的羰基、C1~C6的酯基、C1~C6的烷基胺基、C1~C6的烷氧基、C1~C6的芳基。
10.一种组合物,其包括至少一种权利要求1-7任一项所述的式(I)化合物或其盐。
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CN115353462A (zh) * | 2022-08-23 | 2022-11-18 | 上海朗亿功能材料有限公司 | 一种氰基烯酸酯的制备方法 |
WO2024005030A1 (ja) * | 2022-07-01 | 2024-01-04 | 山本化成株式会社 | ジフェニルエテン系化合物、光吸収剤、樹脂組成物及びその用途 |
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CN102439089A (zh) * | 2010-06-28 | 2012-05-02 | 株式会社艾迪科 | 固化性树脂组合物 |
JP2017008219A (ja) * | 2015-06-23 | 2017-01-12 | 株式会社Adeka | 組成物 |
CN109666088A (zh) * | 2017-10-16 | 2019-04-23 | 北京英力科技发展有限公司 | 一种双酮肟酯化合物及其制造方法与应用 |
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CN102439089A (zh) * | 2010-06-28 | 2012-05-02 | 株式会社艾迪科 | 固化性树脂组合物 |
JP2017008219A (ja) * | 2015-06-23 | 2017-01-12 | 株式会社Adeka | 組成物 |
CN109666088A (zh) * | 2017-10-16 | 2019-04-23 | 北京英力科技发展有限公司 | 一种双酮肟酯化合物及其制造方法与应用 |
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WO2024005030A1 (ja) * | 2022-07-01 | 2024-01-04 | 山本化成株式会社 | ジフェニルエテン系化合物、光吸収剤、樹脂組成物及びその用途 |
CN115353462A (zh) * | 2022-08-23 | 2022-11-18 | 上海朗亿功能材料有限公司 | 一种氰基烯酸酯的制备方法 |
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