WO2013060254A1 - Nouveau mélange photoinitiateur composé d'une hydroxyle cétone aromatique et d'un oxyde de phosphoryle et système composite doté de celui-ci et d'un photoabsorbeur - Google Patents
Nouveau mélange photoinitiateur composé d'une hydroxyle cétone aromatique et d'un oxyde de phosphoryle et système composite doté de celui-ci et d'un photoabsorbeur Download PDFInfo
- Publication number
- WO2013060254A1 WO2013060254A1 PCT/CN2012/083322 CN2012083322W WO2013060254A1 WO 2013060254 A1 WO2013060254 A1 WO 2013060254A1 CN 2012083322 W CN2012083322 W CN 2012083322W WO 2013060254 A1 WO2013060254 A1 WO 2013060254A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- alkyl
- phenyl
- parts
- compound
- Prior art date
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- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 19
- 125000003118 aryl group Chemical group 0.000 title claims description 6
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002131 composite material Substances 0.000 title 1
- -1 aromatic hydroxyl ketones Chemical class 0.000 claims abstract description 20
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000005855 radiation Effects 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 229910052717 sulfur Chemical group 0.000 claims description 20
- 239000011593 sulfur Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 239000006096 absorbing agent Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 4
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000013329 compounding Methods 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 150000000179 1,2-aminoalcohols Chemical class 0.000 claims description 2
- 150000000180 1,2-diols Chemical class 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 0 Cc1cc2n[n](-c3cc(*)cc(*)c3O)nc2cc1* Chemical compound Cc1cc2n[n](-c3cc(*)cc(*)c3O)nc2cc1* 0.000 description 8
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-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
- UZUNCLSDTUBVCN-UHFFFAOYSA-N CC(C)(C)CC(C)(C)c(cc1C(C)(C)c2ccccc2)cc(-[n]2nc(cccc3)c3n2)c1O Chemical compound CC(C)(C)CC(C)(C)c(cc1C(C)(C)c2ccccc2)cc(-[n]2nc(cccc3)c3n2)c1O UZUNCLSDTUBVCN-UHFFFAOYSA-N 0.000 description 1
- MMPCZTQLVSESIT-UHFFFAOYSA-N CC(C)(C)c1cc(CCC(O)=O)cc(-[n]2nc(cc(C(F)(F)F)cc3)c3n2)c1O Chemical compound CC(C)(C)c1cc(CCC(O)=O)cc(-[n]2nc(cc(C(F)(F)F)cc3)c3n2)c1O MMPCZTQLVSESIT-UHFFFAOYSA-N 0.000 description 1
- IMDSXUBIOHXAEG-JIPFFQHWSA-N CC(C)(C)c1cc(CCC(OI)=O)cc(N/N=C(/C=CC=C2)\C2=N)c1O Chemical compound CC(C)(C)c1cc(CCC(OI)=O)cc(N/N=C(/C=CC=C2)\C2=N)c1O IMDSXUBIOHXAEG-JIPFFQHWSA-N 0.000 description 1
- ZCYCLXOQGLQFNH-UHFFFAOYSA-N CC(C)(c1ccccc1)c(cc1C(C)(C)c2ccccc2)cc(-[n]2nc(cc(cc3)Cl)c3n2)c1O Chemical compound CC(C)(c1ccccc1)c(cc1C(C)(C)c2ccccc2)cc(-[n]2nc(cc(cc3)Cl)c3n2)c1O ZCYCLXOQGLQFNH-UHFFFAOYSA-N 0.000 description 1
- OLFNXLXEGXRUOI-UHFFFAOYSA-N CC(C)(c1ccccc1)c(cc1C(C)(C)c2ccccc2)cc(-[n]2nc(cccc3)c3n2)c1O Chemical compound CC(C)(c1ccccc1)c(cc1C(C)(C)c2ccccc2)cc(-[n]2nc(cccc3)c3n2)c1O OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 1
- GDRWFBWRIXQZQC-RBWKUIHFSA-N CC(C)(c1ccccc1)c(cc1C(C)(C)c2ccccc2)cc(N/N=C(/C=C(C=C2)F)\C2=N)c1O Chemical compound CC(C)(c1ccccc1)c(cc1C(C)(C)c2ccccc2)cc(N/N=C(/C=C(C=C2)F)\C2=N)c1O GDRWFBWRIXQZQC-RBWKUIHFSA-N 0.000 description 1
- LASPUFNKSHFTTC-IRUTTXEMSA-N CCC(C)(C)c(cc1C(C)(C)CC)cc(N/N=C(/C=C(C(F)(F)F)C=C2)\C2=N)c1O Chemical compound CCC(C)(C)c(cc1C(C)(C)CC)cc(N/N=C(/C=C(C(F)(F)F)C=C2)\C2=N)c1O LASPUFNKSHFTTC-IRUTTXEMSA-N 0.000 description 1
- RQJOJEFYGQQXTH-UHFFFAOYSA-N CCCCCC(C)(C)c(cc1-[n]2nc(cc(C(F)(F)F)cc3)c3n2)cc(C(C)(C)c2ccccc2)c1O Chemical compound CCCCCC(C)(C)c(cc1-[n]2nc(cc(C(F)(F)F)cc3)c3n2)cc(C(C)(C)c2ccccc2)c1O RQJOJEFYGQQXTH-UHFFFAOYSA-N 0.000 description 1
- OMGOAXJWKSHCGN-UHFFFAOYSA-N CCCCCC(C)(C)c(cc1-[n]2nc(cc(C(F)(F)F)cc3)c3n2)cc(Cc(cc(C(C)(C)CCCCC)cc2-[n]3nc(cc(C(F)(F)F)cc4)c4n3)c2O)c1O Chemical compound CCCCCC(C)(C)c(cc1-[n]2nc(cc(C(F)(F)F)cc3)c3n2)cc(Cc(cc(C(C)(C)CCCCC)cc2-[n]3nc(cc(C(F)(F)F)cc4)c4n3)c2O)c1O OMGOAXJWKSHCGN-UHFFFAOYSA-N 0.000 description 1
- PGVDMRQHIDQFBA-UHFFFAOYSA-N CCCCCC(C)(C)c(cc1-[n]2nc(cc(C(F)(F)F)cc3)c3n2)ccc1O Chemical compound CCCCCC(C)(C)c(cc1-[n]2nc(cc(C(F)(F)F)cc3)c3n2)ccc1O PGVDMRQHIDQFBA-UHFFFAOYSA-N 0.000 description 1
- JNFNZBWBHCDNNE-UHFFFAOYSA-N CCCCCC(C)(C)c(cc1-[n]2nc(cc(cc3)S(CCCC)(=O)=O)c3n2)cc(C(C)(C)c2ccccc2)c1O Chemical compound CCCCCC(C)(C)c(cc1-[n]2nc(cc(cc3)S(CCCC)(=O)=O)c3n2)cc(C(C)(C)c2ccccc2)c1O JNFNZBWBHCDNNE-UHFFFAOYSA-N 0.000 description 1
- QDTBASZKEDRRJK-UHFFFAOYSA-N CCCCCC(C)(C)c(cc1C(C)(C)CCCCC)cc(-[n]2nc(cc(C(F)(F)F)cc3)c3n2)c1O Chemical compound CCCCCC(C)(C)c(cc1C(C)(C)CCCCC)cc(-[n]2nc(cc(C(F)(F)F)cc3)c3n2)c1O QDTBASZKEDRRJK-UHFFFAOYSA-N 0.000 description 1
- SFKWIGVFZKZGGQ-UHFFFAOYSA-N CCCCCCCCS(c1cc2n[n](-c(cc(C(C)(C)CCCCC)cc3C(C)(C)CCCCC)c3O)nc2cc1)(=O)=O Chemical compound CCCCCCCCS(c1cc2n[n](-c(cc(C(C)(C)CCCCC)cc3C(C)(C)CCCCC)c3O)nc2cc1)(=O)=O SFKWIGVFZKZGGQ-UHFFFAOYSA-N 0.000 description 1
- 241000199223 Elaeocarpus kirtonii Species 0.000 description 1
- 235000009414 Elaeocarpus kirtonii Nutrition 0.000 description 1
- NTUUTVWBMAUHPD-MSIZOGDBSA-N N=C(C=CC(C(F)(F)F)=C1)/C1=N\Nc(cc(CCO)cc1)c1O Chemical compound N=C(C=CC(C(F)(F)F)=C1)/C1=N\Nc(cc(CCO)cc1)c1O NTUUTVWBMAUHPD-MSIZOGDBSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 235000013584 Tabebuia pallida Nutrition 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 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
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003811 finger Anatomy 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- DMKSVUSAATWOCU-HROMYWEYSA-N loteprednol etabonate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)OCCl)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O DMKSVUSAATWOCU-HROMYWEYSA-N 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- WFRLANWAASSSFV-FPLPWBNLSA-N palmitoleoyl ethanolamide Chemical compound CCCCCC\C=C/CCCCCCCC(=O)NCCO WFRLANWAASSSFV-FPLPWBNLSA-N 0.000 description 1
- 125000006368 phosphonoyl group Chemical group [*:1]P([*:2])=O 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
- C07F9/3252—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) containing the structure -C(=X)-P(=X)(R)(XR), (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- 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
Definitions
- the invention relates to the technical field of light radiation curing, in particular to a novel photoinitiator system composed of a combination of an aromatic hydroxy ketone and an acylphosphine oxide compound, and a photoinitiator system and a suitable hydroxybenzoic acid having red light absorbing characteristics.
- the triazole-based light absorbing agent is compounded to form an ethylenically unsaturated system which can be cured by irradiation of light (ultraviolet light or visible light or an equivalent source).
- Phosphonoyl compounds are important photoinitiators and have been extensively disclosed in the patent literature, for example EP 1106627 A1, EP0615980A2, WO2006056541A1, WO2011003772A1, CN1823077A, CN1659175A and the like.
- a characteristic disadvantage of the phosphono compounds in practical applications is that the air oxygen barrier effect is remarkable when the polymerization is initiated, so that the cured coating containing the surface is dry. ) The effect is not good.
- phosphono compounds are often used in combination with hydroxyketone photoinitiators to achieve balanced surface and through Curing curing.
- the acylphosphine oxide compound may contain a single or a plurality of acylphosphine oxide [ie, -P(O)-C(O)- units] photoinitiating reactive functional groups, and the general structure ( I ) thereof is:
- X is oxygen or sulfur
- n and m each independently may have a value of 1 or 2.
- R 1 is an unsubstituted straight or branched alkyl group having 1 to 18 carbon atoms (labeled C 1 -C 18 ) or containing 2 to 18 carbon atoms (labeled C 2 ) -C 18 , the same alkenyl group; or a linear or branched alkyl group having 1 to 18 carbon atoms or an alkenyl group having 2 to 18 carbon atoms, which has one or more substituents.
- R 1 is -OR 10 base
- R 1 is -CO 2 H , -CO 2 R 10 , -CONR 10 R 11 , -CO-ethylene-, -CO-phenyl- (wherein the phenyl group may contain one or more C 1 -C 8 alkanes Or a C 1 -C 8 alkoxy group or a C 1 -C 8 alkylthio group or a chlorine atom), or -CO-CR 10 R 11 R 12 ;
- R 1 is phenyl-C 1 -C 4 -alkyl, phenyl, naphthyl, biphenyl, C 5 -C 12 cycloalkyl, or a five or six membered heterocyclic ring containing an oxygen or sulfur or nitrogen atom
- substituents may each contain one or more C 1 -C 8 alkyl or C 1 -C 8 alkoxy or C 1 -C 8 alkylthio or chlorine atom or -NR 10 R 11 substituent;
- R 3 has the same definition as R 1 ;
- acylphosphine oxides conforming to the general structure ( I ) include, but are not limited to, the following structures:
- the aromatic hydroxy ketone compound may contain one or more photoinitiating hydroxy ketone functional groups, characterized in that the hydroxy ketone structure and other substituents exhibit an unusual meta relationship on the aromatic ring, and the general structure thereof ( II ) is:
- p is an integer between 1 and 2000, preferably, p is an integer between 1 and 20; more preferably, p is an integer between 1 and 6; When the value is much larger than 20, it represents a p-repolymerized structure ( II );
- R 6 and R 7 are each independently a phenyl group, a linear or branched C 1 -C 12 alkyl group, and the alkyl group may contain a phenyl or naphthyl or biphenyl substituted by one to five R 10 or OR 10 or halogen, or the alkyl group may be interrupted by one or more non-continuous oxygen or sulfur or nitrogen atoms;
- R 6 and R 7 It is also possible to form a ring structure of 5 to 10 yuan.
- R 8 is hydrogen or a group conforming to the definition of R 10 , preferably R 8 is hydrogen, C 1 -C 6 alkyl, or a silane group having a total number of carbon atoms of C 3 -C 12 , the silane-based carbon chain may be One to four discontinuous oxygen or sulfur or nitrogen atoms are interrupted;
- R 9 is a p-valent linking unit corresponding to the definition of R 1 above; preferably, when p is 1 , R 9 is OH , Cl , SH , NH 2 , OR 10 , SR 10 , NHR 10 , NR 10 R 11 , or a quaternary ammonium salt cation form ( R 10 R 11 R 12 N + ); when p is greater than or equal to 2, R 9 is N , NR 10 , SO 2 , P(O)O 3 , PO 3 , or R 9 (H) p is correspondingly a p-alcohol, a p-mercaptan, a p-phenol, a p-carboxylic acid, a p-acid chloride, a p-amine, a p-ary amide, or a p-membered isocyanate. When p is 2, R 9 can also be a single key;
- An example of a preferred p-acid chloride is an acid chloride structure corresponding to the above p-carboxylic acid example
- R 9 (H) p may be p-member 1,2-diol, p-member 1,2-thiol, p-member 1,2-amino alcohol, or p-member 1,2-N-substituted amine a base alcohol; when R 9 (H) p takes these structures, the p-membered meta-substituted aromatic hydroxy ketone compound having the general structure ( II ) is preferably via a corresponding monomer compound [i.e., p has a value of 1, R 9 is a structure obtained by a classical epoxy ring-opening reaction of OH, SH, NH 2 , or NHR 10 compound ( II )] and a suitable p-epoxy compound. Examples of preferred p-epoxy compounds are:
- Z is hydrogen or CH 2 R 9 ;
- meta-substituted aromatic hydroxy ketone compounds conforming to the general structure ( II ) include, but are not limited to, the following structures:
- the general structure ( III ) of the Hydroxyphenylbenzotriazole UV absorber having red-shifted light absorption characteristics is:
- R 13 and R ' 13 are each independently hydrogen or halogen; and R 14 and R ' 14 are independently of each other, halogen, -CF 3 , -NO 2 , -CN , -COR 20 , -CO 2 R 20 , -CONHR 20 , -CONR 20 R 21 , -POR 20 R 21 , -NR 20 -COR 21 , -OSR 20 , -O 2 SR 20 , or C 1 -C 12 polyfluoro substituted alkyl;
- R 20 and R 21 are each independently hydrogen, a linear or branched C 1 -C 24 alkyl group, a linear or branched C 2 -C 24 alkenyl group, a C 5 -C 24 -containing cycloalkyl group, a C 7 -C 15 -containing phenylalkyl group, or a phenyl group, which may have from 1 to 4 C 1 -C 4 alkyl or alkoxy substituents on the phenyl ring;
- R 20 And the chain of R 21 may be interrupted by not more than 6 discontinuous oxygen or sulfur or nitrogen atoms, or may contain no more than 4 OH, NH 2 , substituted NH 2 , SH , NCO , or ester groups;
- R 15 is the same as R 20 or R 21 ; when R 15 is a C 7 -C 15 -containing phenylalkyl group, or a phenyl group, the phenylalkyl group or the phenyl group may have 1 to 4 benzene rings a C 1 -C 4 alkyl or alkoxy substituent, in which case R 14 can be hydrogen;
- R 16 and R ' 16 are independent of each other and are the same as R 20 or R 21 ;
- r takes a value of 1 or 2
- q takes a value of 0 , 1 or 2 ;
- R 17 is R 20 , -OR 20 , -NR 20 R 21 , -PO(OR 20 ) 2 , -OSi(R 20 ) 3 , or -OCO-R 20 ;
- Q is a divalent linking unit which is a C 1 -C 24 alkyl group or a C 6 -C 24 substituted aryl group; the chain may be no more than 6 non-continuous oxygen or sulfur or nitrogen atoms Intermittent
- Examples of preferred hydroxybenzotriazole-like compounds conforming to the general structure ( III ) include, but are not limited to, the following structures:
- the present invention discloses a novel photoinitiator compounding mixture system characterized by comprising at least one acylphosphine oxide compound represented by the general structure ( I ) and at least one aromatic compound represented by the general structure ( II ) Hydroxyketone compound.
- the weight percentage of the acylphosphine oxide represented by the general formula ( I ) may be from 0.5% to 99.5, based on 100% by weight of the unit parts.
- the change between %, correspondingly, the weight percentage of the aromatic hydroxyketone compound represented by the general structure ( II ) may vary from 99.5% to 0.5%.
- the invention also discloses a mixture curable by radiation (ultraviolet or visible light or equivalent light source), the mixture being characterized by containing at least one polymerizable ethylenically unsaturated compound and a novel definition of claim ( 1 ) Acylphosphine oxide / aromatic hydroxy ketone complex photoinitiator system.
- the acylphosphine oxide/aromatic hydroxyketone compound photoinitiator as defined in claim ( 1 ) may be used in an amount of from 0.01 to 20 parts per 100 parts by weight based on the total weight of such an ethylenically unsaturated compound. 0.5 to 10 servings.
- the invention also discloses a novel mixture system curable by radiation (ultraviolet or visible light or equivalent light source), the system characterized by comprising at least one photoinitiator mixture as defined in claim ( 1 ), at least one A hydroxybenzotriazole-based light absorbing agent compound of the general structure ( III ), and at least one polymerizable ethylenically unsaturated compound.
- the photocured mixture system was prepared in the following percentage by weight (100 parts in total), and the mixture was stirred or dissolved and sprayed on an aluminum plate (about 20 Micron) with high pressure mercury lamp (400 W/cm) ) initiate polymerization for radiation from the source.
- the acylphosphine oxide photoinitiator and meta-substituted hydroxyketone initiator used in the examples are characterized by a structure after each case.
- the curing efficiency was judged by the finger pressing method (that is, the thumb nail pressing film repeatedly wiped the coating without breaking) to confirm the completion of photocuring.
- Embodiment 6 UV disc ink
- Example 7 Light absorber containing UV ink
- the photoinitiator mixture of the above examples all achieved sufficient curing of the system, exhibiting excellent photopolymerization initiating activity.
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Abstract
La présente invention a trait à un nouveau système photoinitiateur constitué d'une combinaison d'hydroxyle cétones aromatiques et d'oxydes de phosphoryle et à un système contenant une insaturation oléfinique qui est durcissable par rayonnement lumineux (rayonnement ultraviolet ou lumière visible ou source lumineuse équivalente) et formulé à partir d'un tel système photoinitiateur et d'un photoabsorbeur approprié doté de la caractéristique d'absorption de la lumière à décalage vers le rouge, tel qu'un hydroxyle benzotriazole.
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CN2011103304344A CN103073658A (zh) | 2011-10-26 | 2011-10-26 | 新型芳香羟基酮和膦酰氧化物的光引发剂混合物及其与光吸收剂的复合体系 |
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Cited By (3)
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GB2508454A (en) * | 2012-07-24 | 2014-06-04 | Lambson Ltd | Photopolymerisation processes and novel compounds therefor |
WO2018059561A1 (fr) * | 2016-09-30 | 2018-04-05 | Allnex Belgium S.A. | Compositions durcissables par rayonnement présentant des propriétés anti-taches |
US10919867B2 (en) | 2015-07-07 | 2021-02-16 | 3M Innovative Properties Company | Substituted benzotriazole phenols |
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EP3019508B1 (fr) * | 2013-07-08 | 2019-01-30 | IGM Group B.V. | Photo-initiateur d'oxyde bisacylphosphine liquide |
CN107400144B (zh) * | 2017-08-03 | 2020-04-14 | 深圳有为技术控股集团有限公司 | 酰基膦(氧)化合物及其制备方法和应用 |
CN109517432A (zh) * | 2018-11-13 | 2019-03-26 | 长沙新宇高分子科技有限公司 | 一种含液态酰基膦氧化物的组合物及其应用 |
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US11359110B2 (en) | 2016-09-30 | 2022-06-14 | Allnex Belgium S.A. | Radiation curable compositions with anti-stain properties |
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