CS257798B2 - Photopolymerizable system - Google Patents

Photopolymerizable system Download PDF

Info

Publication number: CS257798B2
Authority: CS; Czechoslovakia
Prior art keywords: phenyl; photoinitiators; oder; compounds; propyl ketone
Prior art date: 1985-09-28

Application number

CS866523A

Other languages

Czech (cs)

English (en)

Inventor

Manfred Koehler

Joerg Ohngemach

Eike Poetsch

Original Assignee

Merck Patent Gmbh

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.)

1985-09-28

Filing date

1986-09-10

Publication date

1988-06-15

1986-09-10 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1988-06-15 Publication of CS257798B2 publication Critical patent/CS257798B2/cs

Links

125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract 2
239000003999 initiator Substances 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 40
125000004432 carbon atom Chemical group C* 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 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052757 nitrogen Chemical group 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
-1 R3 H Chemical group 0.000 abstract description 43
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 14
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000001723 curing Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000000047 product Substances 0.000 description 9
230000005855 radiation Effects 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
230000032050 esterification Effects 0.000 description 8
238000005886 esterification reaction Methods 0.000 description 8
238000006116 polymerization reaction Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
238000000576 coating method Methods 0.000 description 7
239000007857 degradation product Substances 0.000 description 7
239000004922 lacquer Substances 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
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 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000000976 ink Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
XNLHQURWXIWCDF-UHFFFAOYSA-N 2-[4-[2,4-dihydroxy-2,4-dimethyl-3-oxo-5-[4-(2-prop-2-enoyloxyethoxy)phenyl]pentyl]phenoxy]ethyl prop-2-enoate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCOC(=O)C=C)C=C1 XNLHQURWXIWCDF-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000000463 material Substances 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
238000007639 printing Methods 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
PREGASFGSUVSBQ-UHFFFAOYSA-N (2,4-dimethyl-3-oxo-1,5-diphenyl-4-prop-2-enoyloxypentan-2-yl) prop-2-enoate Chemical compound C1(=CC=CC=C1)CC(C)(OC(C=C)=O)C(=O)C(C)(CC1=CC=CC=C1)OC(C=C)=O PREGASFGSUVSBQ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000977 initiatory effect Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000178 monomer Substances 0.000 description 4
230000009965 odorless effect Effects 0.000 description 4
VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 3
NDJCDNQKIINPMP-UHFFFAOYSA-N 2,4-dihydroxy-2,4-dimethyl-1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=CC=C1 NDJCDNQKIINPMP-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000004925 Acrylic resin Substances 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
150000008366 benzophenones Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000123 paper Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
238000004383 yellowing Methods 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
BUFQATNYFCBSNB-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis(4-hydroxyphenyl)-2,4-dimethylpentan-3-one Chemical compound C=1C=C(O)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(O)C=C1 BUFQATNYFCBSNB-UHFFFAOYSA-N 0.000 description 2
LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 2
FLKIJNISGLPWAC-UHFFFAOYSA-N 2-[4-(2-methylpropanoyl)phenoxy]ethyl acetate Chemical compound CC(C)C(=O)C1=CC=C(OCCOC(C)=O)C=C1 FLKIJNISGLPWAC-UHFFFAOYSA-N 0.000 description 2
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-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
BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical class C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 2
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
244000028419 Styrax benzoin Species 0.000 description 2
235000000126 Styrax benzoin Nutrition 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
235000008411 Sumatra benzointree Nutrition 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
YLQFBBDMNWYTOS-UHFFFAOYSA-N [4-[2,4-dihydroxy-2,4-dimethyl-3-oxo-5-(4-prop-2-enoyloxyphenyl)pentyl]phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=CC=C(C=C1)CC(C)(O)C(=O)C(C)(CC1=CC=C(C=C1)OC(C=C)=O)O YLQFBBDMNWYTOS-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
150000004056 anthraquinones Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical class C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229960002130 benzoin Drugs 0.000 description 2
239000012965 benzophenone Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
239000003822 epoxy resin Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
235000019382 gum benzoic Nutrition 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
239000007788 liquid Substances 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
238000000034 method Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
150000002989 phenols Polymers 0.000 description 2
ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000006552 photochemical reaction Methods 0.000 description 2
239000000049 pigment Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
239000004848 polyfunctional curative Substances 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000002028 premature Effects 0.000 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 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
238000003847 radiation curing Methods 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000010409 thin film Substances 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
WVTSQCDTEHQBLF-UHFFFAOYSA-N 1-[2-(dimethylamino)phenyl]-2-hydroxy-2-phenylethanone Chemical class CN(C)C1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 WVTSQCDTEHQBLF-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
PEVGZCHVOHFKLB-UHFFFAOYSA-N 2-[4-[2,4-dihydroxy-2,4-dimethyl-5-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]-3-oxopentyl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1CC(C)(O)C(=O)C(C)(O)CC1=CC=C(OCCOC(=O)C(C)=C)C=C1 PEVGZCHVOHFKLB-UHFFFAOYSA-N 0.000 description 1
GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
RZCDMINQJLGWEP-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpent-4-en-1-one Chemical compound C=1C=CC=CC=1C(CC=C)(O)C(=O)C1=CC=CC=C1 RZCDMINQJLGWEP-UHFFFAOYSA-N 0.000 description 1
XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
WHFKYDMBUMLWDA-UHFFFAOYSA-N 2-phenoxyethyl acetate Chemical compound CC(=O)OCCOC1=CC=CC=C1 WHFKYDMBUMLWDA-UHFFFAOYSA-N 0.000 description 1
RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
BZISNWGGPWSXTK-UHFFFAOYSA-N 3-hydroxypropyl benzoate Chemical compound OCCCOC(=O)C1=CC=CC=C1 BZISNWGGPWSXTK-UHFFFAOYSA-N 0.000 description 1
UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
LRKOXPROLBZHJQ-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)CC(C)(OC(C=C)=O)C(=O)C(C)(CC1=CC=C(C=C1)C(C)C)OC(C=C)=O Chemical compound C(C)(C)C1=CC=C(C=C1)CC(C)(OC(C=C)=O)C(=O)C(C)(CC1=CC=C(C=C1)C(C)C)OC(C=C)=O LRKOXPROLBZHJQ-UHFFFAOYSA-N 0.000 description 1
BGVSMFYVGFHYPN-UHFFFAOYSA-N C1(=CC=CC=C1)CC(C)(OC(C(=C)C)=O)C(=O)C(C)(CC1=CC=CC=C1)OC(C(=C)C)=O Chemical compound C1(=CC=CC=C1)CC(C)(OC(C(=C)C)=O)C(=O)C(C)(CC1=CC=CC=C1)OC(C(=C)C)=O BGVSMFYVGFHYPN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
229920001730 Moisture cure polyurethane Polymers 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical class OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
238000003848 UV Light-Curing Methods 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 description 1
TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 description 1
BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
SGJPFMDBSWNEDP-UHFFFAOYSA-N [4-[2,4-dihydroxy-2,4-dimethyl-5-[4-(2-methylprop-2-enoyloxy)phenyl]-3-oxopentyl]phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1CC(C)(O)C(=O)C(C)(O)CC1=CC=C(OC(=O)C(C)=C)C=C1 SGJPFMDBSWNEDP-UHFFFAOYSA-N 0.000 description 1
MFYWJYZWALOVHT-UHFFFAOYSA-N [4-[2,4-dimethyl-2,4-bis(2-methylprop-2-enoyloxy)-5-[4-(2-methylprop-2-enoyloxy)phenyl]-3-oxopentyl]phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1CC(C)(OC(=O)C(C)=C)C(=O)C(C)(OC(=O)C(C)=C)CC1=CC=C(OC(=O)C(C)=C)C=C1 MFYWJYZWALOVHT-UHFFFAOYSA-N 0.000 description 1
FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004848 alkoxyethyl group Chemical group 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
CFPRXVGQNOAZPR-UHFFFAOYSA-N benzoyl benzoate;prop-2-enoic acid Chemical compound OC(=O)C=C.C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CFPRXVGQNOAZPR-UHFFFAOYSA-N 0.000 description 1
VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
FOYJYXHISWUSDL-UHFFFAOYSA-N butyl 4-(dimethylamino)benzoate Chemical compound CCCCOC(=O)C1=CC=C(N(C)C)C=C1 FOYJYXHISWUSDL-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000013016 damping Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000010408 film Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
239000003828 free initiator Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000005283 haloketone group Chemical group 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000006224 matting agent Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000006259 organic additive Substances 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical class C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
229960000969 phenyl salicylate Drugs 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000007650 screen-printing Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000725 suspension Substances 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
MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
150000007964 xanthones Chemical class 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Spectroscopy & Molecular Physics (AREA)
Life Sciences & Earth Sciences (AREA)
General Physics & Mathematics (AREA)
Wood Science & Technology (AREA)
Polymerisation Methods In General (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Paints Or Removers (AREA)

CS866523A 1985-09-28 1986-09-10 Photopolymerizable system CS257798B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853534645 DE3534645A1 (de)	1985-09-28	1985-09-28	Copolymerisierbare fotoinitiatoren

Publications (1)

Publication Number	Publication Date
CS257798B2 true CS257798B2 (en)	1988-06-15

Family

ID=6282204

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS866523A CS257798B2 (en)	1985-09-28	1986-09-10	Photopolymerizable system

Country Status (17)

Country	Link
US (1)	US4922004A (fr)
EP (1)	EP0217205B1 (fr)
JP (1)	JP2514804B2 (fr)
AR (1)	AR241265A1 (fr)
AT (1)	ATE70258T1 (fr)
AU (1)	AU595830B2 (fr)
BR (1)	BR8604672A (fr)
CA (1)	CA1275109A (fr)
CS (1)	CS257798B2 (fr)
DD (1)	DD258614A5 (fr)
DE (2)	DE3534645A1 (fr)
DK (1)	DK172255B1 (fr)
ES (1)	ES2004660A6 (fr)
FI (1)	FI89162C (fr)
HU (1)	HU201510B (fr)
PL (1)	PL149572B2 (fr)
ZA (1)	ZA867370B (fr)

Families Citing this family (175)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3738567A1 (de) *	1987-03-12	1988-09-22	Merck Patent Gmbh	Coreaktive fotoinitiatoren
EP0302831B1 (fr) *	1987-08-05	1993-05-12	Ciba-Geigy Ag	Composés
US4950795A (en) *	1987-08-27	1990-08-21	Ciba-Geigy Corporation	Oligomeric benzil ketals and their use as photoinitiators
US5095044A (en) *	1987-08-27	1992-03-10	Ciba-Geigy Corporation	Oligomeric benzil ketals and their use as photoinitiators
US5248805A (en) *	1988-12-31	1993-09-28	Basf Aktiengesellschaft	Radiation-senstive, ethylenically unsaturated, copolymerizable compounds and their preparation
US5118779A (en) *	1989-10-10	1992-06-02	Polymedica Industries, Inc.	Hydrophilic polyurethane elastomers
DE4014489A1 (de) *	1990-05-07	1991-11-14	Merck Patent Gmbh	Copolymerisierbare benzilketal-fotoinitiatoren
RU2091385C1 (ru) *	1991-09-23	1997-09-27	Циба-Гейги АГ	Бисацилфосфиноксиды, состав и способ нанесения покрытий
IL101993A (en) *	1991-10-23	1995-06-29	Hughes Aircraft Co	Method for creating enhanced liquid crystal membranes with diffused polymer with initiating photo that can be copolymerized
ES2037611B1 (es) *	1991-12-04	1994-04-01	Consejo Superior Investigacion	Nuevos modelos, monomeros y polimeros fotosensibles y portadores del grupo-p-nitronaftil-aminocarbonilo. su procedimiento de preparacion.
USRE35060E (en) *	1991-12-11	1995-10-10	Alliedsignal Inc.	Fluorinated photoinitiators and their application in UV curing of fluorinated monomers
US5274179A (en) *	1993-04-06	1993-12-28	Alliedsignal Inc.	Fluorinated photoinitiators and their application in UV curing of fluorinated monomers
ES2059261B1 (es) *	1992-10-08	1995-11-16	Ciba Geigy Ag	Alquil-bisacilfosfinoxidos.
US5506279A (en) *	1993-10-13	1996-04-09	Minnesota Mining And Manufacturing Company	Acrylamido functional disubstituted acetyl aryl ketone photoinitiators
KR970704849A (ko) *	1994-07-29	1997-09-06	워렌 리차드 보비	가교 점탄성 물질로 경화가능한 아크릴 시럽
AU5635796A (en) *	1995-05-10	1996-11-29	Avery Dennison Corporation	Pigmented, uv-cured, acrylic-based, pressure sensitive adhes ives, and method for making same
ATE225052T1 (de) *	1995-07-19	2002-10-15	Ciba Sc Holding Ag	Heterogene photoinitiatoren, photopolymerisierbare zusammensetzungen und deren verwendung
AU4743696A (en) *	1995-12-29	1997-07-28	Minnesota Mining And Manufacturing Company	Use of pendant photoreactive moieties on polymer precursors to prepare hydrophilic pressure sensitive adhesives
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1985
- 1985-09-28 DE DE19853534645 patent/DE3534645A1/de not_active Withdrawn
1986
- 1986-09-09 AU AU62470/86A patent/AU595830B2/en not_active Ceased
- 1986-09-10 CS CS866523A patent/CS257798B2/cs unknown
- 1986-09-13 EP EP86112676A patent/EP0217205B1/fr not_active Expired - Lifetime
- 1986-09-13 AT AT86112676T patent/ATE70258T1/de not_active IP Right Cessation
- 1986-09-13 DE DE8686112676T patent/DE3682858D1/de not_active Expired - Lifetime
- 1986-09-25 ES ES8602162A patent/ES2004660A6/es not_active Expired
- 1986-09-26 BR BR8604672A patent/BR8604672A/pt active Search and Examination
- 1986-09-26 ZA ZA867370A patent/ZA867370B/xx unknown
- 1986-09-26 JP JP61226362A patent/JP2514804B2/ja not_active Expired - Fee Related
- 1986-09-26 DK DK461886A patent/DK172255B1/da not_active IP Right Cessation
- 1986-09-26 DD DD86294723A patent/DD258614A5/de not_active IP Right Cessation
- 1986-09-26 CA CA000519146A patent/CA1275109A/fr not_active Expired - Lifetime
- 1986-09-26 PL PL1986261574A patent/PL149572B2/pl unknown
- 1986-09-26 AR AR86305384A patent/AR241265A1/es active
- 1986-09-26 FI FI863894A patent/FI89162C/fi not_active IP Right Cessation
- 1986-09-26 HU HU864118A patent/HU201510B/hu not_active IP Right Cessation
- 1986-09-29 US US06/912,473 patent/US4922004A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0217205A2 (fr)	1987-04-08
AR241265A1 (es)	1992-04-30
AU6247086A (en)	1987-04-02
BR8604672A (pt)	1987-06-16
JP2514804B2 (ja)	1996-07-10
JPS6281345A (ja)	1987-04-14
HUT43027A (en)	1987-09-28
FI89162C (fi)	1993-08-25
US4922004A (en)	1990-05-01
PL261574A2 (en)	1987-10-19
EP0217205A3 (en)	1988-09-21
AU595830B2 (en)	1990-04-12
DK461886A (da)	1987-03-29
DK461886D0 (da)	1986-09-26
FI863894L (fi)	1987-03-29
ES2004660A6 (es)	1989-02-01
EP0217205B1 (fr)	1991-12-11
ZA867370B (en)	1987-05-27
ATE70258T1 (de)	1991-12-15
DE3682858D1 (de)	1992-01-23
HU201510B (en)	1990-11-28
DE3534645A1 (de)	1987-04-02
DD258614A5 (de)	1988-07-27
DK172255B1 (da)	1998-02-09
FI89162B (fi)	1993-05-14
PL149572B2 (en)	1990-02-28
CA1275109A (fr)	1990-10-09
FI863894A0 (fi)	1986-09-26

Publication	Publication Date	Title
CS257798B2 (en)	1988-06-15	Photopolymerizable system
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US5047556A (en)	1991-09-10	Photoinitiators having a combined structure
US5147901A (en)	1992-09-15	Propionphenone derivatives as photoinitiators for photopolymerization
FI86412C (fi)	1992-08-25	Fotoinitiatorer foer fotopolymerisation av omaettade system.
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US5248805A (en)	1993-09-28	Radiation-senstive, ethylenically unsaturated, copolymerizable compounds and their preparation
US4559371A (en)	1985-12-17	Photocurable colored compositions employing alpha-amino phenone initiator
JPS61194062A (ja)	1986-08-28	チオ置換ケトン化合物を用いる光重合開始剤
US4672079A (en)	1987-06-09	Polymeric or polymerizable aromatic-aliphatic ketones suitable for use as polymerization photoinitiators
CH648016A5 (de)	1985-02-28	Aromatisch-aliphatische ketone und ihre verwendung als photoinitiatoren.
US9353207B2 (en)	2016-05-31	Alkylphenyl derivatives and application thereof as photoinitiator
HU181680B (en)	1983-11-28	Process for photopolymerizing unsaturated compounds
JP2000510868A (ja)	2000-08-22	狭い波長帯の紫外線（ｕｖ）キュアシステムに使用する光活性化合物
JP2007501776A (ja)	2007-02-01	高厚コーティングの製造のための透明な光重合可能なシステム
US9394455B2 (en)	2016-07-19	Copolymerizable photoinitiators
DE2155000A1 (de)	1973-05-10	Thiomethylierte benzophenone
GB1580968A (en)	1980-12-10	Compositions polymerizable by uv irradiation
CA1196649A (fr)	1985-11-12	Dihydro-1,3-dioxepines acylees en 2; preparation et utilisation comme initiateurs en photo