TW201602127A - 多功能醯基膦氧化物光起始劑 - Google Patents
多功能醯基膦氧化物光起始劑 Download PDFInfo
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- TW201602127A TW201602127A TW104117208A TW104117208A TW201602127A TW 201602127 A TW201602127 A TW 201602127A TW 104117208 A TW104117208 A TW 104117208A TW 104117208 A TW104117208 A TW 104117208A TW 201602127 A TW201602127 A TW 201602127A
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- photoinitiator
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- phenyl
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- 239000000203 mixture Substances 0.000 claims abstract description 68
- -1 2,6-dichlorophenyl Chemical group 0.000 claims description 294
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 20
- 229920005862 polyol Polymers 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
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- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000879 imine group Chemical group 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
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- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 7
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
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- 230000002028 premature Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
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- JFVZTPIWVQKFFW-UHFFFAOYSA-N propanoate;tris(2-hydroxyethyl)azanium Chemical compound CCC([O-])=O.OCC[NH+](CCO)CCO JFVZTPIWVQKFFW-UHFFFAOYSA-N 0.000 description 1
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- 239000011241 protective layer Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000001020 pyronin dye Substances 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 150000004060 quinone imines Chemical class 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
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- 239000002594 sorbent Substances 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- HOECDVCUNDIEFU-UHFFFAOYSA-N trityl dihydrogen phosphite Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OP(O)O)C1=CC=CC=C1 HOECDVCUNDIEFU-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000001018 xanthene dye Substances 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
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
- C07F9/3229—Esters of aromatic acids (P-C aromatic linkage)
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
-
- 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)]
- C07F9/36—Amides thereof
-
- 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
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- 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
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- 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
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
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- 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
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- 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
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
本發明是有關一系列的新穎的多功能單及雙醯基膦氧化物,其是有用於作為光起始劑,並且,本發明是有關一種光硬化性組成物,其包含上述光起始劑。
Description
本發明是有關一種新穎的多功能單及雙醯基膦氧化物,其是有用於作為光起始劑,並且,本發明是有關一種光硬化性組成物,其包含上述光起始劑。
放射線硬化性組成物已用於許多產業中,該產業包括塗料但並不限於此,該塗料是用於例如下述各種基材:混凝土、金屬、陶瓷、玻璃、塑膠、複合材料及紡織品。該組成物之硬化是藉由光起始劑來完成,該光起始劑會吸收紫外線(UV)能量並進行反應而產生自由基,該自由基在該組成物中會依序與雙鍵進行反應(例如丙烯酸基)來形成新的自由基(亦即起始步驟)。
然而,當放射線硬化性組成物用於食品包裝、玩具及牙科等之用途中時,光起始劑的量及相關分解產物是嚴重的問題,該相關分解產物能夠從硬化後之塗料擴散至周圍的介質(遷移
(migration))。低分子量化合物,通常不會完全併入聚合物網中,且有會被萃取出或從硬化後之組成物擴散出之傾向。因此,持續努力設計一種光起始劑,其從該硬化後之組成物遷移出或被萃取出之傾向較低。
克服此等問題之一種方案,是使用含有
乙烯性不飽和部分之光起始劑,例如:WO 2006/056541、WO 2004/103580及AU 200/3205731中記載一種醯基膦氧化物之衍生物,其具有(甲基)丙烯酸功能性。該乙烯性不飽和基能夠使光起始劑在硬化程序中併入聚合物結構中。
一種替代方案是使用一種光起始劑,其
分子大小經增加,而提高妨礙進入硬化後之產物中之可能性,結果使產物之遷移性及/或萃取性之等級降低。此解決手段已揭示於US 6,296,986、US 7,354,957、US 7,166,647、EP 1616921及EP 1674499。亦能夠像US 2012/0046376所揭示這樣,在相同化合物中將分子大小較大的優點與乙烯性不飽和的優點結合。
然而,本發明所屬技術領域中具有通常
知識者均了解,兩種光起始劑均有會喪失反應性之傾向。因此,為了達到需要的硬化速度,經常需要相當大量的反應性物質,而亦會因此使黏度增加至
放射線硬化性組成物之許多用途中不期望的等級,該放射線硬化性組成物之用途為像例如噴墨列印這樣的用途。然而,濃度大於10~12%的非丙烯酸功能性材料,會開始產生塑化劑之作用、或僅將硬化後之薄膜之交聯密度降低至會使機械特性受損之點。
而且,乙烯性不飽和基存在,會限制此等光起始劑之熱安定性及儲存安定性。
並且,某些光起始劑與光硬化性系統之溶解度及適合性會受到限制,此等光起始劑是例如:具有高分子量或含有不飽和基。
其是意指其中會持續需要其他光起始劑,該其他光起始劑不會遷移且與放射線硬化系統之反應性及適合性受到改善。
單及雙醯基膦氧化物,已廣泛用於放射線硬化性組成物中作為光起始劑。該等醯基膦氧化物,反應性高且不會黃變,並且在350~420nm之間具有較小的吸收帶,而適合用於發光二極體(LED)燈。具有此等所有特徵之醯基膦氧化物,是一種適合廣範圍的用途之獨特類別的光起始劑。然而,該等醯基膦氧化物顯示相同的上述應用限制。
目前,我們已發現一系列的新穎的多功能單及雙醯基膦氧化物光起始劑,該等光起始劑不含光硬化性乙烯性不飽和基,且具有高溶解度、高
反應性及高安定性,且遷移及/或被萃取出之傾向非常低。
此等多功能單及雙醯基膦氧化物,能夠
作為下述化合物之反應產物獲得:本案中定義為核心之含有三個以上的反應性基之多功能化合物、與含有單及雙醯基膦氧化物基之化合物。
令人驚訝地,此等多功能單及雙醯基膦
氧化物,顯示每個磷單元之反應性較該單功能醯基膦氧化物光起始劑之反應性更優異。然而,WO 2012/0046376、US 7,354,957及US 7,166,647中所記載之先前技術的光起始劑,具有較低的反應性而在光硬化性組成物中必須投予較大量。
同時,比較低分子量的核心,會使該光
起始劑在光硬化性組成物中溶解性更高,尤其是在光硬化性塗佈組成物中溶解性更高。
本發明之基本目標是一種式I之光起始劑:
其中,
各個A相互獨立地表示O、S、NR3;G為多功能化合物亦即核心G-(A-H)m+n之殘基,其中,各個A-H表示醇基、胺基或硫醇基;m及n均為整數且m+n在3~10之間;m在3~8之間;R1、R2相互獨立地為C1~C18烷基、C6~C12芳基及C5~C12環烷基、或者是含有氧原子及/或氮原子及/或硫原子之五員雜環自由基或六員雜環自由基,且該C1~C18烷基、C6~C12芳基及C5~C12環烷基分別是未經或經以一個或兩個以上的氧原子及/或硫原子以及/或經取代或未經取代之亞胺基所隔開,上述自由基分別可經芳基、烷基、芳氧基、烷氧基、雜原子及/或雜環自由基所取代;R2亦可為R1-(C=O)-;Y為O或S;R3為氫或C1~C4烷基;惟,該式I之光起始劑不含光硬化性乙烯性不飽和基。
本發明之另一目標是一種光硬化性組成物,其包含:a)0.05至20重量%(wt%)、較佳是0.2至10重量%的至少一種的式I之光起始劑;及
b)30至99.9重量%、較佳是50至98.9重量的至少一種乙烯性不飽和化合物。
本發明之一目標是一種光硬化程序,其是對上述光硬化性組成物進行光硬化,該光硬化程序包含下述步驟:I)提供上述光硬化性組成物;及II)以光源來對該光硬化性組成物進行光硬化。
本發明之式I之光起始劑較佳為:式I中,m+n在3~8之間,更佳為m+n在3~6之間。
本發明之式I之光起始劑較佳為:式I中,m在3~6之間,更佳為m在3~5之間。
當n不是0時,該式I之化合物具有游離醇基及/或胺基及/或硫醇基。
本發明之一實施形態中,式I中,A僅為氧。此時,G-(A-H)m+n為多羥基化合物,其是選自多元醇之單體、寡聚物、聚合物及該等之混合物。
適合的多元醇之單體及寡聚物之例子為:甘油、二甘油、三甘油、三乙醇胺、三羥甲基丙烷、二(三羥甲基丙烷)、季戊四醇、二季戊四醇;山梨糖醇、甘露糖醇、木糖醇等糖醇類;該等之混合物。
多元醇之聚合物之例子為:烷氧化化合物(alkoxylated compound)、脂肪族或芳香族
的多羥基聚醚、多羥基聚酯、多羥基聚醯胺、多羥基聚醯亞胺、多羥基聚碳酸酯;苯乙烯-烯丙醇共聚物。
為了實現本發明,以該烷氧化化合物特
佳。這樣的烷氧化化合物之例子,為使上述多元醇之單體及寡聚物烷氧化而成之化合物,該烷氧化為例如:乙氧化(ethoxylated)及/或丙氧化(propoxylated)及/或丁氧化(butoxylated)。其他適合的例子,為使下述之直鏈或分枝的多胺(polyamine)烷氧化而成之化合物、及多烷氧化二胺,該多烷氧化二胺為例如:乙氧化乙二胺及乙氧化1,3-丙二胺。在本發明之烷氧化化合物中,對環氧烷具有反應性之各個基,能夠產生0~15個烷氧基單元,較佳是產生1~6個烷氧基單元。
一較佳實施形態中,G-(A-H)m+n是選自多元醇之單體及寡聚物。
另一較佳實施形態中,G-(A-H)m+n是選自經乙氧化及/或丙氧化而成之多元醇之單體及寡聚物。
根據本發明之另一實施形態,式I中,A僅為硫。此時,G-(A-H)m+n為多硫醇化合物,其能夠藉由例如巰基有機酸與多元醇之酯化反應來獲得,該多硫醇化合物為例如:三羥甲基丙烷
參(巰基乙酸酯)、季戊四醇肆(巰基乙酸酯)、三羥甲基丙烷參(β-巰基丙酸酯)、季戊四醇肆(β-巰基丙酸酯)、二季戊四醇多(β-巰基丙酸酯)等。該多硫醇化合物之用語亦包括:含末端硫醇基的聚醚;含末端硫醇基的聚硫醚;藉由多環氧基化合物與硫化氫之反應來獲得之硫醇化合物;及藉由多硫醇化合物與環氧化合物之反應來獲得之含末端硫醇基的硫醇化合物。
根據本發明之再一實施形態,式I中,
A僅為氮,因此,G-(A-H)m+n為直鏈或分枝的多胺。
該多胺可選自例如:聚伸乙亞胺、聚乙
烯胺、經多胺所取代之聚烷二醇、經多胺所取代之聚(甲基)丙烯酸酯、經多胺所取代之聚酯、聚胺基酸、胺基封端二甲基聚矽氧烷(amodimethicone);聚伸乙基胺等聚伸烷基胺;以及該等之混合物。具體例為:二伸乙三胺、三伸乙四胺、四伸乙五胺、亞精胺(spermidine)、精胺(spermine)、4-胺甲基-1,8-辛二胺、N-(2-胺基乙基)-1,3-丙二胺、及N,N’-雙(3-胺基丙基)乙二胺。
式I中,A能夠為氧及/或氮及/或硫之
混合。此時,G-(A-H)m+n亦能夠為一種化合物,其含有不同的功能基,該功能基為例如胺基及
羥基。該等化合物之例子為二乙醇胺及參(羥甲基)胺基甲烷。
G-(A-H)m+n之數目平均分子量,
較佳為不大於1500,且更佳為不大於800,最佳為不大於500。
G-(A-H)m+n較佳是選自下述:甘
油、乙氧化甘油及/或丙氧化甘油、二甘油、乙氧化二甘油及/或丙氧化二甘油、三羥甲基丙烷、乙氧化三羥甲基丙烷及/或丙氧化三羥甲基丙烷、二(三羥甲基丙烷)、乙氧化二(三羥甲基丙烷)及/或丙氧化二(三羥甲基丙烷)、季戊四醇、乙氧化季戊四醇及/或丙氧化季戊四醇、二季戊四醇、乙氧化二季戊四醇及/或丙氧化二季戊四醇、山梨糖醇、乙氧化山梨糖醇及/或丙氧化山梨糖醇。
另一較佳的G-(A-H)m+n為三乙醇
胺、乙氧化三乙醇胺及/或丙氧化三乙醇胺、4-胺甲基-1,8-辛二胺、N-(2-胺基乙基)-1,3-丙二胺、參(羥甲基)胺基甲烷、二乙醇胺、乙氧化二乙醇胺及/或丙氧化二乙醇胺、1-硫甘油、N,N’-雙(3-胺基丙基)乙二胺。
為了實現本發明,較適合的該殘基G是不含光硬化性乙烯性不飽和基。
本發明之式I中:
C1~C18烷基可未經取代或經芳基、烷基、芳氧基、烷氧基、雜原子及/或雜環自由基所取代,該C1~C18烷基為例如:甲基、乙基、丙基、異丙基、正丁基、二級丁基、三級丁基、戊基、己基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、癸基、十二烷基、十四烷基、十七烷基、十八烷基、1,1-二甲基丙基、1,1-二甲基丁基、1,1,3,3-四甲基丁基、苯甲基、1-苯基乙基、2-苯基乙基、α,α-二甲基苯甲基、二苯甲基(benzhydryl)、對甲苯基甲基、1-(對丁基苯基)乙基、對氯苯甲基、2,4-二氯苯甲基、對甲氧基苯甲基、間乙氧基苯甲基、2-羥基乙基、2-羥基丙基、3-羥基丙基、4-羥基丁基、6-羥基己基、2-甲氧基乙基、2-甲氧基丙基、3-甲氧基丙基、4-甲氧基丁基、6-甲氧基己基、2-乙氧基乙基、2-乙氧基丙基、3-乙氧基丙基、4-乙氧基丁基、或6-乙氧基己基、2-甲氧羰基乙基、2-乙氧羰基乙基、2-丁氧羰基丙基、1,2-二(甲氧羰基)乙基、2-丁氧基乙基、二乙氧基甲基、二乙氧基乙基、1,3-二氧雜環戊烷-2-基(1,3-dioxolan-2-yl)、1,3-二噁烷-2-基(1,3-dioxan-2-yl)、2-甲基-1,3-二氧雜環戊烷-2-基、4-甲基-1,3-二氧雜環戊烷-2-基、2-異丙氧基乙基、2-丁氧基丙基、2-辛氧基乙基、氯甲基、2-氯乙基、三氯甲基、三氟甲基、1,1-二甲基-2-
氯乙基、2-甲氧基異丙基、丁硫基甲基、2-十二烷硫基乙基、2-苯硫基乙基、2,2,2-三氟乙基、2-胺基乙基、2-胺基丙基、3-胺基丙基、4-胺基丁基、6-胺基己基、2-甲胺基乙基、2-甲胺基丙基、3-甲胺基丙基、4-甲胺基丁基、6-甲胺基己基、2-二甲胺基乙基、2-二甲胺基丙基、3-二甲胺基丙基、4-二甲胺基丁基、6-二甲胺基己基、2-羥基-2,2-二甲基乙基、2-苯氧基乙基、2-苯氧基丙基、3-苯氧基丙基、4-苯氧基丁基、6-苯氧基己基;
C6~C12芳基是未經取代或經芳基、烷基、芳氧基、烷氧基、雜原子及/或雜環自由基所取代,該C6~C12芳基為例如:苯基、甲苯基、二甲苯基、4-聯苯基、2-氯苯基或3-氯苯基或4-氯苯基、2,6-二氯苯基或2,4-二氯苯基、2,4,6-三氯苯基、2-氟苯基或3-氟苯基或4-氟苯基、2,6-二氟苯基或2,4-二氟苯基、2,4,6-三氟苯基、2-甲基苯基或3-甲基苯基或4-甲基苯基、2,6-二甲基苯基或2,4-二甲基苯基、2,4,6-三甲基苯基、2-乙基苯基或3-乙基苯基或4-乙基苯基、2,6-二乙基苯基或2,4-二乙基苯基、2-異丙基苯基或3-異丙基苯基或4-異丙基苯基、2-三級丁基苯基或3-三級丁基苯基或4-三級丁基苯基、十二烷基苯基、2-甲氧基苯基或3-甲氧基苯基或4-甲氧基苯基、2,6-二甲氧基苯基或2,4-二甲氧基苯基、2-乙氧基苯基或3-乙氧
基苯基或4-乙氧基苯基、2,6-二乙氧基苯基或2,4-二乙氧基苯基、己氧基苯基、α-萘基、β-萘基、甲基萘基、異丙基萘基、氯萘基、乙氧基萘基、2,6-二甲基苯基、2,4,6-三甲基苯基、2,6-二甲氧基苯基、2,6-二氯苯基、4-溴苯基、2-硝基苯基或4-硝基苯基、2,4-二硝基苯基或2,6-二硝基苯基、4-二甲胺基苯基、4-乙醯基苯基、甲氧基乙基苯基、及乙氧基甲基苯基;
C5~C12環烷基是未經取代或經芳基、烷基、芳氧基、烷氧基、雜原子及/或雜環自由基所取代,該C5~C12環烷基為例如:環戊基、環己基、環辛基、環十二烷基、甲基環戊基、2,5-二甲基環戊基、甲基環己基、2,6-二甲基環己基、2,6-二乙基環己基、丁基環己基、甲氧基環己基、2,6-二甲氧基環己基、2,6-二乙氧基環己基、丁硫基環己基、氯環己基、2,6-二氯環己基、2,5-二氯環戊基、及降冰片基或降冰片烯基等飽和或不飽和雙環系統、金剛烷基等三環系統;含有氧原子及/或氮原子及/或硫原子之五員雜環自由基或六員雜環自由基為例如:呋喃基、噻吩基(thiophenyl)、吡咯基、吡啶基、吲哚基、苯并噁唑基、二氧雜環戊烷基、二噁烷基、苯并咪唑基、苯并噻唑基(benzothiazolyl)、二甲基吡啶基、甲基喹啉基、二甲基吡咯基、甲氧基呋喃基、二甲氧基吡啶
基、二氟吡啶基、甲硫基苯基、異丙硫基苯基、及三級丁硫基苯基。
R1較佳為苯基、甲苯基、二甲苯基、
2-氯苯基或3-氯苯基或4-氯苯基、2,6-二氯苯基或2,4-二氯苯基、2,4,6-三氯苯基、2-甲基苯基或3-甲基苯基或4-甲基苯基、2,6-二甲基苯基或2,4-二甲基苯基、2,4,6-三甲基苯基、2-乙基苯基或3-乙基苯基或4-乙基苯基、2,6-二乙基苯基或2,4-二乙基苯基、2-異丙基苯基或3-異丙基苯基或4-異丙基苯基、2-三級丁基苯基或3-三級丁基苯基或4-三級丁基苯基、2-甲氧基苯基或3-甲氧基苯基或4-甲氧基苯基、2,6-二甲氧基苯基或2,4-二甲氧基苯基、2,6-二乙氧基苯基或2,4-二乙氧基苯基、α-萘基、β-萘基、甲基萘基、4-溴苯基、2-硝基苯基或4-硝基苯基、2,4-二硝基苯基或2,6-二硝基苯基、4-二甲胺基苯基、4-乙醯基苯基、環戊基、環己基、2,5-二甲基環戊基、2,6-二甲基環己基、2,6-二乙基環己基、2,6-二甲氧基環己基、2,6-二乙氧基環己基、2,6-二氯環己基、2,5-二氯環戊基、金剛烷基、乙基、丙基、異丙基、正丁基、二級丁基、三級丁基、戊基、己基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、癸基、十二烷基、2-呋喃基或3-呋喃基、2-噻吩基或3-噻吩基、2-吡咯基或3-吡咯基、及二甲基吡咯基。
R1更佳為苯基、2,6-二氯苯基、
2,4,6-三氯苯基、2,6-二甲基苯基、2,4,6-三甲基苯基、2,6-二乙基苯基、2,6-二甲氧基苯基、2,6-二乙氧基苯基、α-萘基、2,6-二硝基苯基、2,6-二甲基環己基、2,6-二乙基環己基、2,6-二甲氧基環己基、2,6-二乙氧基環己基、或2,6-二氯環己基、三級丁基、戊基、己基、庚基、辛基、及2-乙基己基。
R1最佳為苯基、2,6-二氯苯基、
2,4,6-三氯苯基、2,6-二甲基苯基、2,4,6-三甲基苯基、2,6-二甲氧基苯基、及三級丁基。
R2較佳為R1-(C=O)-、甲基、乙
基、丙基、異丙基、正丁基、二級丁基、三級丁基、戊基、己基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、癸基、十二烷基、苯甲基、對氯苯甲基、2,4-二氯苯甲基、對甲氧基苯甲基、苯基、甲苯基、二甲苯基、4-聯苯基、2-氯苯基或3-氯苯基或4-氯苯基、2,4-二氯苯基或2,6-二氯苯基、2,4,6-三氯苯基、2-甲基苯基或3-甲基苯基或4-甲基苯基、2,4-二甲基苯基或2,6-二甲基苯基、2,4,6-三甲基苯基、2-乙基苯基或3-乙基苯基或4-乙基苯基、2,4-二乙基苯基或2,6-二乙基苯基、2-異丙基苯基或3-異丙基苯基或4-異丙基苯基、2-三級丁基苯基或3-三級丁基苯基或4-三級丁
基苯基、2-甲氧基苯基或3-甲氧基苯基或4-甲氧基苯基、2,4-二甲氧基苯基或2,6-二甲氧基苯基、2-乙氧基苯基或3-乙氧基苯基或4-乙氧基苯基、α-萘基、甲基萘基、氯萘基、乙氧基萘基、2-硝基苯基或4-硝基苯基、2,4-二硝基苯基或2,6-二硝基苯基、4-二甲胺基苯基、或4-乙醯基苯基。
R2更佳為R1-(C=O)-、甲基、乙
基、丙基、異丙基、正丁基、二級丁基、三級丁基、戊基、己基、2-乙基己基、苯基、二甲苯基、4-聯苯基、2-氯苯基或3-氯苯基或4-氯苯基、2,4-二氯苯基、2-甲基苯基或3-甲基苯基或4-甲基苯基、2,4-二甲基苯基、2-乙基苯基或3-乙基苯基或4-乙基苯基、2-甲氧基苯基或3-甲氧基苯基或4-甲氧基苯基、2,4-二甲氧基苯基、2-乙氧基苯基或3-乙氧基苯基或4-乙氧基苯基、α-萘基、甲基萘基、氯萘基、乙氧基萘基、及2-硝基苯基或4-硝基苯基。
R2最佳為R1-(C=O)-、甲基、乙
基、丙基、異丙基、正丁基、二級丁基、三級丁基、苯基、4-聯苯基、2-氯苯基或3-氯苯基或4-氯苯基、2-甲基苯基或3-甲基苯基或4-甲基苯基、2-甲氧基苯基或3-甲氧基苯基或4-甲氧基苯基、及2-乙氧基苯基或3-乙氧基苯基或4-乙氧基苯基。
再次重申,為了實現本發明,較適合的R1及R2是不含光硬化性乙烯性不飽和基。
Y較佳為O。
R3較佳為氫或C1~C4烷基,該C1~C4烷基為例如:甲基、乙基、丙基、異丙基、正丁基、二級丁基、及三級丁基。
特佳的態樣中,R1為2,4,6-三甲基苯基,R2為苯基。
代表性的式I之多功能單及雙醯基膦氧化物,是如表1中所記載但並不限於此。當為聚合性多功能核心時,上述多功能醯基膦氧化物光起始劑具有一分子量分布之事實,對本發明所屬技術領域中具有通常知識者而言為顯而易知之事項。表1所示之該等結構中,a、b、c、d、e及f為整數,且獨立地在0~15之範圍內。
式I之化合物,能夠依照本發明所屬技術領域中具有通常知識者熟知之慣用方法來製備,例如能夠依照下述程序來製備。
詳細而言,式III之次膦醯氯能夠藉由下述方式來合成:使對應的烷基酯與PCl5(如Methoden der Organischen Chemie(有機化學方法),Vol.12/1,p.241中所記載)進行反應。然後,該式III之次膦醯氯能夠在三乙胺存在下
與G-(A-H)m+n進行反應而獲得上述式I之產物。
由此,該式III之化合物能夠與G-(A
-H)m+n進行反應,而獲得式I之酯(次膦醯氯與醇類進行反應)、硫酯(次膦醯氯與硫醇類進行反應)或醯胺(次膦醯氯與胺類進行反應)。
獲得式III之化合物之再一方法已記載
於DE 10206117中所記載,該文獻中記載該對應的次膦酸(IV)會在吡啶存在下被亞硫醯氯轉化為次膦醯氯(III)。
獲得式I之化合物之另一方法已記載於Methoden der Organischen Chemie,Vol.12/1,p.500,該文獻中記載式II之烷基酯會在鈉存在下藉由與G-(A-H)m+n進行酯交換反應而轉換為式I之化合物。
根據本發明,式I之光起始劑能夠用於製備光硬化性組成物,該光硬化性組成物包含乙烯性不飽和化合物b)。
該不飽和化合物b)能夠含有一個或兩個
以上的烯烴雙鍵。該不飽和化合物b)能夠為低分子量(亦即單體)或高分子量(亦即寡聚物)。
適合的具有一個雙鍵之低分子量單體之
例子為:丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-乙基己酯或丙烯酸2-羥基乙酯、丙烯酸異冰片酯、及甲基丙烯酸甲酯、甲基丙烯酸乙酯等丙烯酸或甲基丙烯酸之烷酯或羥基烷酯。亦令人感興趣之例子還有經矽或氟所改質之樹脂例如聚矽氧丙烯酸酯類。該等單體之更多例子為:丙烯腈、丙烯醯胺、甲基丙烯醯胺、N-取代(甲基)丙烯醯胺、苯乙烯、烷基苯乙烯、及鹵苯乙烯;乙烯乙烯酯等乙烯酯;異丁基乙烯基醚等乙烯基醚;N-乙烯基吡咯啶酮、氯乙烯或偏二氯乙烯。
具有超過一個雙鍵之單體之例子為:乙
二醇二丙烯酸酯、丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、六亞甲基二醇二丙烯酸酯、雙酚A二丙烯酸酯、4,4’-雙(2-丙烯醯氧基乙氧基)二苯基丙烷、三羥甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯或季戊四醇四丙烯酸酯、丙烯酸乙烯酯、二乙烯基苯、琥珀酸二乙烯酯、酞酸二烯丙酯、磷酸三烯丙酯、異氰脲酸三烯丙酯、或異氰脲酸參(2-丙烯醯基乙酯)。
高分子量(亦即寡聚)多不飽和化合物之
例子為:丙烯酸化環氧樹脂、丙烯酸化聚酯或含乙烯基醚聚酯或含環氧基聚酯、丙烯酸化聚胺酯(acrylated polyurethane)、或丙烯酸化聚醚。不飽和寡聚物之更多例子為不飽和聚酯樹脂,該不飽和聚酯樹脂通常是由馬來酸、酞酸及一種或兩種以上的二元醇所製備,且該不飽和聚酯樹脂之分子量為大約500~3000。這樣的不飽和寡聚物亦能夠被稱為預聚物。
為了實現本發明,特別適合的化合物之
例子為:乙烯性不飽和羧酸與多元醇或多環氧化物之酯、鏈上或側基上含有乙烯性不飽和基之聚合物、側鏈上具有(甲基)丙烯酸基之聚合物及共聚物、以及一種或兩種以上的這樣的聚合物之混合物,該鏈上或側基上含有乙烯性不飽和基之聚合物為:不飽和的聚酯、聚醯胺及聚胺酯以及該等之共聚物;醇酸樹脂;聚丁二烯及丁二烯共聚物。
不飽和羧酸或不飽和羧酸酐有助於製備
上述酯,該不飽和羧酸或不飽和羧酸酐之具體例為:丙烯酸、甲基丙烯酸、馬來酸酐、巴豆酸、伊康酸、肉桂酸;以及次亞麻油酸(linolenic acid)及油酸等不飽和脂肪酸。較佳為丙烯酸及甲基丙烯酸。
能夠被酯化之多元醇為芳香族、脂肪族
及環脂族的多元醇,較佳為脂肪族及環脂族的多元醇。
芳香族多元醇為例如:氫醌、4,4’-二
羥基二苯基、2,2’-二(4-羥基苯基)丙烷;以及酚醛清漆類及甲階酚醛清漆類(resol)。
脂肪族及環脂族的多元醇之例子包括含
有較佳為2~12個碳原子數之烷二醇,該烷二醇為例如:乙二醇、1,2-丙二醇或1,3-丙二醇、1,2-丁二醇或1,3-丁二醇或1,4-丁二醇、戊二醇、己二醇、辛二醇、十二烷二醇、二乙二醇、三乙二醇、分子量較佳為200~1500之聚乙二醇、1,3-環戊二醇、1,2-環己二醇或1,3-環己二醇或1,4-環己二醇、1,4-二(羥甲基)環己烷、甘油、參(β-羥基乙基)胺、三羥甲基乙烷、三羥甲基丙烷、季戊四醇、二季戊四醇、及山梨糖醇。
能夠被酯化之多環氧化物包括由上述多
元醇所得之多環氧化物,該多元醇尤其是芳香族多元醇及表氯醇。聚合物鏈或側基上含有羥基之聚合物及寡聚物,亦適合作為多元醇,該聚合物及寡聚物為例如:聚乙烯醇及其共聚物、或是聚(甲基)丙烯酸羥烷酯或其共聚物。更適合的多元醇為具有末端羥基之寡酯(oligoester)。
更適合的乙烯性不飽和化合物b)為不飽
和聚醯胺,該不飽和聚醯胺是由不飽和羧酸及芳香族、脂肪族及環脂族多胺所獲得,該多胺較佳是具有2~6個胺基,更佳是具有2~4個胺基。這樣的多胺可舉例如:乙二胺、1,2-丙二胺或1,3-丙二胺、1,2-丁二胺或1,3-丁二胺或1,4-丁二胺、1,5-戊二胺、1,6-己二胺、辛二胺、十二烷二胺、1,4-二胺基環己胺、異佛酮二胺、苯二胺、雙伸苯基二胺、二(β-胺基乙基)醚、二伸乙三胺、三伸乙四胺、及二(β-胺基乙氧基)乙烷、及二(β-胺基丙氧基)乙烷。其他適合的多胺為聚合物及共聚物以及寡聚醯胺,該聚合物及共聚物可在側鏈進而含有胺基,該寡聚醯胺含有末端胺基。
這樣的不飽和聚醯胺之具體例為:亞甲
基雙(丙烯醯胺)、1,6-六亞甲基(雙丙烯醯胺)、二伸乙三胺參(甲基丙烯醯胺)、雙(甲基丙烯醯胺基丙氧基)乙烷、及N-[(β-羥基乙氧基)乙基]丙烯醯胺。
為了實現本發明,亦較適合的不飽和聚
胺酯為例如:從飽和或不飽和的二異氰酸酯及不飽和或飽和的二醇衍生出之不飽和聚胺酯。聚丁二烯及聚異戊二烯以及該等之共聚物亦是有用的。適合的共聚單體包括例如:乙烯、丙烯、丁烯及己烯、
(甲基)丙烯酸酯、丙烯腈、苯乙烯、及氯乙烯等烯烴類。
側鏈上具有不飽和(甲基)丙烯酸基之聚
合物,能夠作為成分b)使用。該等聚合物通常可為:酚醛清漆型環氧樹脂與(甲基)丙烯酸之反應產物;經與(甲基)丙烯酸進行酯化之乙烯醇或其羥烷基衍生物之均聚物或共聚物;及經與(甲基)丙烯酸羥烷酯進行酯化之(甲基)丙烯酸酯之均聚物或共聚物。
本發明之光硬化性組成物,除了成分a)
及b)以外,還能夠包含其他光起始劑c)及/或添加劑d)。
該其他光起始劑c),在本發明之組成物
中,能夠存在0.5~15重量%的量,較佳是存在1~10重量%的量。
適合的其他光起始劑c)之例子為:樟腦
醌、二苯甲酮、二苯甲酮衍生物、苯乙酮、苯乙酮衍生物、二烷氧基苯乙酮、α-羥基酮、α-胺基酮、4-芳醯基-1,3-二氧雜環戊烷、安息香烷基醚;及苯偶醯二甲基縮酮等苯偶醯縮酮(benzil ketal);1-[4-[(4-苯甲醯基苯基)硫基]苯基]-2-甲基-2-[(4-甲基苯基)磺醯基]丙-1-酮(Esacure 1001,來自Lamberti S.p.A.公司)等酮基碸;苯基乙醛酸酯及其衍生物、乙醛酸苯
酯二聚物;像例如EP 126541中所記載這樣的二苯甲酮四甲酸過酸酯等過酸酯;醯基膦氧化物光起始劑(其能夠選自單醯基膦氧化物、雙醯基膦氧化物、參醯基膦氧化物);鹵甲基三嗪(halomethyltriazine);由鄰氯六苯基雙咪唑與2-巰基苯并噻唑所組合而成之六芳基雙咪唑/共起始劑系統;二茂鐵鎓鹽(ferrocenium)化合物或雙(環戊二烯基)雙(2,6-二氟-3-(N-吡咯基)苯基)鈦等二茂鈦;O-醯基肟酯光起始劑。
α-羥基酮及α-胺基酮之例子為:1-羥
基環己基苯基酮、2-羥基-2-甲基-1-苯基-丙-1-酮、1-[4-(2-羥基乙氧基)苯基]-2-羥基-2-甲基-1-丙-1-酮、2-羥基-1-{4-[4-(2-羥基-2-甲基丙醯基)苯甲基]苯基}-2-甲基丙-1-酮、2-羥基-1-{4-[4-(2-羥基-2-甲基丙醯基)苯氧基]苯基}-2-甲基-丙-1-酮、2-甲基-1-(4-甲硫基苯基)-2-(N-嗎啉基)丙-1-酮)、2-苯甲基-2-二甲胺基-1-(4-(N-嗎啉基)苯基)丁-1-酮、及(2-(二甲胺基)-2-[(4-甲基苯基)甲基]-1-[4-(4-嗎啉基)苯基]-1-丁酮)。
O-醯基肟酯光起始劑之例子為:1,2-
辛二酮,1-[4-(苯硫基)苯基]-2-(O-苯甲醯基肟)、乙酮1-[9-乙基-6-(2-甲基苯甲醯基)-9H-
咔唑-3-基]1-(O-乙醯基肟)、或GB 2339571中所記載之O-醯基肟酯光起始劑。
醯基膦氧化物光起始劑之例子包括:雙
(2,4,6-三甲基苯甲醯基)苯基膦氧化物、雙(2,6-二甲氧基苯甲醯基)-2,4,4-三甲基戊基膦氧化物、雙(2,4,6-三甲基苯甲醯基)-(2,4-二戊氧基苯基)、2,4,6-三甲基苯甲醯基二苯基膦氧化物、及(2,4,6-三甲基苯甲醯基)苯基次膦酸乙酯,但並不限於此等。
該鹵甲基三嗪型光起始劑之例子為:2-
[2-(4-甲氧基苯基)乙烯基]-4,6-雙(三氯甲基)-[1,3,5]三嗪、2-(4-甲氧基苯基)-4,6-雙(三氯甲基)-[1,3,5]三嗪、2-(3,4-二甲氧基苯基)-4,6-雙(三氯甲基)-[1,3,5]三嗪、2-甲基-4,6-雙(三氯甲基)-[1,3,5]三嗪。
當將本發明之光硬化性組成物用於混成
系統(在此情況中是意指自由基硬化性系統與陽離子硬化性系統之混合物)中時,亦能夠進而使用陽離子光起始劑作為光起始劑c)。適合的陽離子光起始劑之例子為:像US 4,950,581中所記載這樣的芳香族的鋶鹽、鏻鹽或錪鹽;或六氟磷酸(η6-異丙基苯)(η5-環戊二烯基)鐵(II)等環戊二烯基芳烴-鐵(II)錯合物鹽;或例如像GB 2348644、US
4,450,598、US 4,136,055、WO 00/10972及WO 00/26219中所記載這樣的肟型光潛在性酸添加劑d)能夠為例如:光敏化劑、促進劑/共起始劑、熱起始劑、黏合劑、安定劑、及該等之混合物。
該光硬化程序亦能夠藉由進而至少添加
光敏化劑0.05~12重量%作為添加劑d)來改善,該光敏化劑較佳是添加0.1~10重量%。
光敏化劑之例子為:本技術領域中慣用
的光敏化劑;二苯甲酮類、噻噸酮(thioxanthone)類、蒽醌類及3-醯基香豆素衍生物等芳香族羰基化合物;聯三苯類、苯乙烯基酮類、及3-(芳醯基亞甲基)噻唑啉類、樟腦醌類;以及曙紅染料、羅丹明(rhodamine)染料及赤蘚紅(erythrosine)染料。
噻噸酮類之例子為:噻噸酮、2-異丙基
噻噸酮、2-氯噻噸酮、2-十二烷基噻噸酮、2,4-二乙基噻噸酮、2,4-二甲基噻噸酮、1-甲氧羰基噻噸酮、2-乙氧羰基噻噸酮、3-(2-甲氧基乙氧羰基)噻噸酮、4-丁氧羰基噻噸酮、3-丁氧羰基-7-甲基噻噸酮、1-氰基-3-氯噻噸酮、1-乙氧羰基-3-氯噻噸酮、1-乙氧羰基-3-乙氧基噻噸酮、1-乙氧羰基-3-胺基噻噸酮、1-乙氧羰基-3-苯硫基噻噸酮、3,4-二[2-(2-甲氧基乙氧基)乙氧羰基]噻噸酮、
1-乙氧羰基-3-(1-甲基-1-(N-嗎啉基)乙基)噻噸酮、2-甲基-6-二甲氧基甲基噻噸酮、2-甲基-6-(1,1-二甲氧基苯甲基)噻噸酮、2-(N-嗎啉基)甲基噻噸酮、2-甲基-6-(N-嗎啉基)甲基噻噸酮、N-烯丙基噻噸酮-3,4-二甲醯亞胺、N-辛基噻噸酮-3,4-二甲醯亞胺、N-(1,1,3,3-四甲基丁基)噻噸酮-3,4-二甲醯亞胺、1-苯氧基噻噸酮、6-乙氧羰基-1,2-甲氧基噻噸酮、6-乙氧羰基-2-甲基噻噸酮、噻噸酮2-聚乙二醇酯、氯化2-羥基-3-(3,4-二甲基-9-酮基-9H-噻噸酮-2-基氧基)-N,N,N-三甲基-1-丙銨(2-hydroxy-3-(3,4-dimethyl-9-oxo-9H-thioxanthon-2-yloxy)-N,N,N-trimethyl-1-propanaminium chloride)、或例如7-甲基噻噸酮-3-甲酸正十二烷酯及N,N-二異丁基-7-甲基噻噸酮-3-胺甲醯胺等PCT/EP2011/069514號專利申請案中所記載之噻噸酮類。噻噸酮衍生物聚合物(例如來自IGM Resins B.V.公司之Omnipol TX;來自Rahn A.G.公司之Genopol TX-1;來自Lambson有限公司之Speedcure 7010)亦適合。
二苯甲酮類之例子為:二苯甲酮、4-苯
基二苯甲酮、4-甲氧基二苯甲酮、4,4’-二甲氧基二苯甲酮、4,4’-二甲基二苯甲酮、4,4’-二氯二苯
甲酮、4,4’-二甲胺基二苯甲酮、4,4’-二乙胺基二苯甲酮、4-甲基二苯甲酮、2,4,6-三甲基二苯甲酮、4-(4-甲硫基苯基)二苯甲酮、3,3’-二甲基-4-甲氧基二苯甲酮、2-苯甲醯基苯甲酸甲酯、4-(2-羥基乙硫基)二苯甲酮、4-(4-甲苯硫基)二苯甲酮、氯化4-苯甲醯基-N,N,N-三甲基苯甲銨(4-benzoyl-N,N,N-trimethylbenzene methanaminium chloride)、氯化2-羥基-3-(4-苯甲醯基苯氧基)-N,N,N-三甲基-1-丙銨一水合物、4-(13-丙烯醯基-1,4,7,10,13-五氧雜十三烷基)二苯甲酮、氯化4-苯甲醯基-N,N-二甲基-N-[2-(1-酮基-2-丙烯基)氧基乙基]苯甲銨。二苯甲酮衍生物聚合物(例如來自IGM Resins B.V.公司之Omnipol BP、Omnipol 2702及Omnipol 682;來自Rahn A.G.公司之Genopol BP-2;來自Lambson有限公司之Speedcure 7005)亦適合。
3-醯基香豆素衍生物之例子為:3-苯
甲醯基香豆素、3-苯甲醯基-7-甲氧基香豆素、3-苯甲醯基-5,7-二(丙氧基)香豆素、3-苯甲醯基-6,8-二氯豆素、3-苯甲醯基-6-氯香豆素、3,3’-羰基雙[5,7-二(丙氧基)香豆素]、3,3’-羰基雙(7-甲氧基香豆素)、3,3’-羰基雙(7-二乙胺基香豆素)、3-異丁醯基香豆素、3-苯甲醯基-5,7-二甲
氧基香豆素、3-苯甲醯基-5,7-二乙氧基香豆素、3-苯甲醯基-5,7-二丁氧基香豆素、3-苯甲醯基-5,7-二(甲氧基乙氧基)香豆素、3-苯甲醯基-5,7-二(烯丙氧基)香豆素、3-苯甲醯基-7-二甲胺基香豆素、3-苯甲醯基-7-二乙胺基香豆素、3-異丁醯基-1,7-二甲胺基香豆素、5,7-二甲氧基-3-(1-萘甲醯基)香豆素、5,7-二甲氧基-3-(1-萘甲醯基)香豆素、3-苯甲醯基苯并[f]香豆素、7-二乙胺基-3-噻吩甲醯基香豆素、3-(4-氰基苯甲醯基)-5,7-二甲氧基香豆素、或ITVA20120041中所記載之3-醯基香豆素衍生物。
3-(芳醯基亞甲基)噻唑啉類之例子
為:3-甲基-1,2-苯甲醯基亞甲基-β-萘并噻唑啉、3-甲基-2-苯甲醯基亞甲基苯并噻唑啉、3-乙基-2-丙醯基亞甲基-β-萘并噻唑啉;其他芳香族羰基化合物為:苯乙酮、3-甲氧基苯乙酮、4-苯基苯乙酮、例如WO 2013/164394中所記載之苯偶醯、2-乙醯基萘、2-萘甲醛、9,10-蒽醌、9-茀酮、二苯并環庚烯酮、呫噸酮(xanthone)、2,5-雙(4-二乙胺基苯亞甲基)環戊酮、例如2-(4-二甲胺基苯亞甲基)茚-1-酮或3-(4-二甲胺基苯基)-1-茚-5-基丙烯酮等α-(對二甲胺基苯亞甲基);酮類、3-苯硫基酞醯亞胺、N-甲基-3,5-二(乙硫基)酞醯亞胺。
本發明之光硬化性組成物,亦能夠為了
方便而包括促進劑/共起始劑,該促進劑/共起始劑為例如:醇類、硫醇類、硫醚類、胺類或醚類,該等具有與鄰接雜原子之碳鍵結而能夠利用的氫;像EP 438123及GB 2180358中所記載這樣的二硫醚類及膦類。這樣的促進劑/共起始劑一般是存在0.2~15重量%的量,較佳是0.2~8重量%的量。
胺類促進劑/共起始劑之適合的例子包
括:脂肪族、環脂族、芳香族、芳基脂肪族、雜環式等的胺類之寡聚物或聚合物,但不限於此等。該等胺類能夠為一級胺、二級胺、或三級胺,例如:丁胺、二丁胺、三丁胺、環己胺、苯甲基二甲基胺、二環己胺、N-苯基甘胺酸、三乙胺、苯基二乙醇胺、三乙醇胺、哌啶、哌嗪(piperazine)、嗎啉、吡啶、喹啉、二甲胺基苯甲酸之酯、米其勒酮(Michler's ketone)(亦即4,4’-雙(二甲胺基)二苯甲酮)、及對應的衍生物。
作為該胺類促進劑/共起始劑,能夠使
用胺改質丙烯酸酯化合物,這樣的胺改質丙烯酸酯之例子包括:US 3,844,916、EP 280222、US 5,482,649或US 5,734,002中所記載丙烯酸酯類,其經藉由與一級胺或二級胺進行反應來改質。
胺聚合物衍生物亦適合作為共起始劑
(例如來自IGM Resins B.V.公司之Omnipol ASA;來自Rahn A.G.公司之Genopol AB-2;來自Lambson有限公司之Speedcure 7040)。
尤其是當為顏料組成物(例如經二氧化
鈦所著色之組成物)時,亦可藉由添加作為額外的添加劑d)之熱起始劑來輔助該硬化程序,該熱起始劑為一種加熱時會形成自由基之化合物,例如:2,2’-偶氮雙(4-甲氧基-2,4-二甲基戊腈)、三氮烯(triazene)、重氮硫醚(diazosulfide)、五氮雜二烯(pentazadiene)等偶氮化合物;或像例如EP 245639中所記載這樣的三級丁基氫過氧化物等氫過氧化物或過氧碳酸酯等過氧化合物。
該光硬化性組成物中亦可添加黏合劑。
當該光硬化性化合物為液狀物質或黏性物質時,添加黏合劑特別有利。黏合劑的量可為例如5~60重量%,較佳為10~50重量%。黏合劑是依照所使用之技術領域及該技術領域需要的性質來選擇,例如:水性溶劑系統及有機溶劑系統中之顯影性、對基材之黏著性、及對氧氣之敏感性。
適合的黏合劑為例如:分子量約5,000
~2,000,000之聚合物,分子量較佳為約10,000~1,000,000。具體例為:甲基丙烯酸甲酯/丙烯
酸乙酯/甲基丙烯酸之共聚物、聚(甲基丙烯酸烷酯)、聚(丙烯酸烷酯)等丙烯酸酯及甲基丙烯酸酯之均聚物及共聚物;纖維素乙酸酯、纖維素乙酸酯丁酸酯、甲基纖維素、乙基纖維素等纖維素之酯及醚;聚乙烯醇縮丁醛、聚乙烯醇縮甲醛、環化橡膠;聚環氧乙烷、聚環氧丙烷、聚四氫呋喃等聚醚;聚苯乙烯、聚碳酸酯、聚胺酯;聚氯乙烯、氯乙烯/偏二氯乙烯之共聚物、偏二氯乙烯與丙烯腈及甲基丙烯酸甲酯及乙酸乙烯酯之共聚物等氯化聚烯烴;聚乙酸乙烯酯、共聚(乙烯/乙酸乙烯酯)、聚己內醯胺及聚(六亞甲基己二醯胺)等聚合物、聚(乙二醇對酞酸酯)及聚(六亞甲基二醇琥珀酸酯)等聚酯。
適合的安定劑為例如能夠防止過早進行
聚合之熱抑制劑,該熱抑制劑為例如:氫醌、氫醌衍生物、對甲氧基苯酚、β-萘酚、2,6-二(三級丁基)對甲酚等立體受阻的酚類。為了增加在黑暗中的儲存安定性,能夠使用例如:環烷酸銅、硬脂酸銅或辛酸銅等銅化合物;三苯膦、三丁膦、亞磷酸三乙酯、亞磷酸三苯酯或亞磷酸三苯甲酯等磷化合物;氯化四甲銨或氯化三甲基苯甲基銨等四級銨化合物;或N,N-二乙基羥基胺等羥基胺衍生物。為了在進行聚合時去除大氣中的氧之目的,能夠添加石蠟或類似的蠟狀物質,該石蠟或類似的蠟狀物質不
溶於聚合物中並且在開始進行聚合時會遷移至表面而形成防止空氣進入之透明的表層。
亦能夠添加例如UV吸收劑等光安定
劑,例如:羥苯基苯并***、羥苯基二苯甲酮、草醯胺、或羥苯基-s-三嗪型。這樣的化合物能夠單獨使用或以混合物之形式使用,且能夠與立體受阻的胺類(HALS)一起使用或不一起使用。
本發明之組成物,亦可包含作為額外的
添加劑d)之光還原性染料,例如:呫噸染料、苯并呫噸染料、苯并噻噸染料、噻嗪染料、派洛寧(pyronin)染料、卟啉(porphyrin)染料、或吖啶染料、及/或放射線裂解性三鹵甲基化合物。此等化合物已記載於例如EP 445624中。
依照目標用途,慣用的額外的添加劑d)
有:增亮劑、填料、顏料、白色及彩色雙方的顏料、著色劑、抗靜電劑、潤濕劑、流動性改進劑(flow improver)、及黏著促進劑。
本發明之組成物中,亦能夠添加本技術
領域中慣用的鏈轉移試劑。該鏈轉移試劑之例子為:硫醇類、胺類及苯并噻唑。
為了使較厚的且經著色之塗料硬化,適
合添加像美國專利第5,013,768號中所記載這樣的玻璃微珠或玻璃纖維粉末。
本發明之組成物,亦可包含著色劑及/
或白色或彩色的顏料。依照目標用途,可使用無機顏料及有機顏料雙方。這樣的添加劑為本發明所屬技術領域中具有通常知識者所周知,一些例子為:金紅石型或銳鈦礦型等的二氧化鈦顏料、碳黑、像鋅白這樣的氧化鋅、像黃色氧化鐵及紅色氧化鐵這樣的氧化鐵、鉻黃、鉻氯、鎳鈦黃、群青藍、鈷藍、釩酸鉍、鎘黃、及鎘紅。有機顏料之例子為:單偶氮顏料或雙偶氮顏料及該等之金屬錯合物;酞菁顏料;苝(perylene)顏料、蒽醌顏料、硫靛顏料、喹吖啶酮顏料或三苯基甲烷顏料等多環顏料;以及二酮基吡咯并吡咯、四氯異吲哚啉酮等異吲哚啉酮、異吲哚啉、二噁嗪(dioxazine)、苯并咪唑酮及喹啉基茚二酮(quinophthalone)顏料。該等顏料可單獨用於配方、或用於混合添加劑。
依照目標用途,該等顏料能夠在配方中
添加本技術領域中慣用的量,例如:以總量為基準時為0.1~30重量%或10~25重量%的量。
本發明之組成物亦可包含例如:非常多
種分級的有機著色劑。例子為:偶氮染料、次甲基染料、蒽醌染料、及金屬錯合物染料。濃度通常為例如:以總量為基準時為0.1~20wt%,尤其是1~5wt%。
添加劑是依照所使用於問題之技術領域
及該技術領域需要的性質來選擇。上述之添加劑d)為本技術領域中慣用者且是依情況來使用本技術領域中慣用的量。
該光硬化性組成物能夠用於各種目的,
例如:作為網版印刷墨水、柔版印刷墨水、膠版印刷墨水及噴墨列印墨水等印刷墨水;作為透明塗層、作為彩色塗層、作為白色塗層來用於例如木材或金屬;作為粉末塗料;作為塗佈材料來尤其是用於紙、木材、金屬或塑膠;作為日光硬化性塗料來用於標記結構及道路、用於相片復原程序、用於全像記錄材料、用於影像記錄程序、或用於製作能夠使用有機溶劑或水性-鹼性介質來進行顯影之印刷板;用於製作網版印刷之遮罩;作為牙科填充複合物;作為黏著劑;作為感壓黏著劑;作為積層樹脂;作為電蝕阻劑(galvanoresist)等光阻;作為抗蝕劑或永久性阻劑;液體及乾膜兩者;作為光建構性介電體;及作為電路之防焊劑;作為製作濾色片時之阻劑來用於任何類型的顯示螢幕;或在製造電漿顯示器及電激發光顯示器時構築結構時作為阻劑;在製作光交換器(optical switch)或光柵(干涉光柵)時作為阻劑;在藉由大量硬化(在透明鑄模中進行紫外線(UV)硬化)或依照像例如美國專利第4,575,330號中所記載這樣的立體微影程序來製
造三維物品時作為阻劑;在製造複合材料(例如苯乙烯聚酯,其可包括玻璃纖維及/或其他纖維及其他佐劑)及厚的層狀組成物時作為阻劑;在將電子零件塗佈或密封時作為阻劑;或作為塗料用於光纖。本發明之組成物亦適合:用於製作隱形眼鏡或佛氏(Fresnel)透鏡等光學透鏡;在製造醫療設備、輔助設備或植入物時使用;在乾膜塗料中使用。
本發明之組成物亦適合製備具有熱向性
之凝膠。這樣的凝膠已記載於例如DE 19700064及EP 678534中。
本發明之化合物及組成物,亦可作為自
由基起始劑或光起始系統來用於放射線硬化性粉末塗料。
本發明之光硬化性組成物適合例如:作
為塗佈材料用於所有種類的基材,該基材為例如木材、紡織品、紙、陶瓷、玻璃、塑膠及金屬,該塑膠為例如聚酯、聚對酞酸乙二酯、聚烯烴及纖維素乙酸酯且尤其是以薄膜之形態使用,該金屬為例如Al、Cu、Ni、Fe、Zn、Mg或Co及GaAs、Si或SiO2,該基材上經藉由例如成像式曝光來附加有保護層或附加有影像。
本發明之光硬化程序,通常是藉由下述
方式來進行:使該光硬化性組成物暴露在約200nm~約600nm的光。依情況,可使用大量的最多
種的光源。點光源及扁平輻射器(地毯燈)雙方均適合。其例子為:碳弧燈、氙弧燈;適當地經金屬鹵化物所摻雜之中壓汞弧輻射器、高壓汞弧輻射器、及低壓汞弧輻射器(金屬鹵化物燈);經微波激發之金屬蒸氣燈、準分子燈、超光化螢光燈管、螢光燈、氬白熾燈、閃光燈、攝影泛光燈、發光二極體(LED)、電子束、X射線、及雷射。燈與被曝光之本發明之基材之間的距離,可依照目標用途及類型以及燈的強度來改變,且可為例如1cm~150cm。
在下述段落中記載本發明之式I之醯基
膦氧化物及光硬化性組成物之製備例,其目的僅為用於例示,並非用於限制。
在氮氣環境中,將甲苯20mL、三乙胺1.41g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯(依照DE 10206117所製備)3.88g之溶液加熱至50℃。添加季戊四醇肆(3-巰基丙酸酯)1.28g,並將該溶液攪拌1小時。將該反應混合物冷卻至室溫,並加入去離子水10mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液20mL清洗1次且以水20mL清洗2次,最後以Na2SO4乾燥。在減壓下將溶劑去除。藉由使用矽膠進行之快速管柱層析法(甲苯/乙酸乙酯,8:2)來將反應產物純化,而以黏性液體之形式獲得光起始劑2.1g。
1H-NMR(CDCl3,δ ppm):2.10(s,24H),2.24(s,12H),2.64(t,8H),2.91-3.16(m,8H),3.99(t,8H),6.80(s,8H),7.41-7.51(m,8H),7.51-7.61(m,4H),7.81-7.91(m,8H)
在氮氣環境中,將三氯甲烷150mL、三乙胺3.49g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯5.31g之溶液加熱至50℃。添加Aionico GL/609(乙氧化甘油,Lamberti S.p.A.公司)1.5g,並將該溶液攪拌2小時。將該反應混合物冷卻至室溫,並加入去離子水10mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液100mL清洗3次且以水100mL清洗2次,並以Na2SO4乾燥。在減壓下將溶劑去除,而以黏性液體之形式獲得光起始劑2.99g。
1H-NMR(CDCl3,δ ppm):2.08(s,18H),2.21(s,9H),3.31-3.78(m,34H),4.03-4.19(m,6H),6.75(s,6H),7.36-7.48(m,6H),7.48-7.58(m,3H),7.71-7.82(m,6H)
31P-NMR(CDCl3,δ ppm):18.2
在氮氣環境中,將甲苯70mL、三乙胺2.44g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯3.5g之溶液加熱至50℃。添加Sorbilene RE/20(乙氧化山梨糖醇,Lamberti S.p.A.公司)3g,並將該溶液攪拌1小時。將該反應混合物冷卻至室溫,並加入去離子水50mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液50mL清洗1次且以水50mL清洗2次,最後以Na2SO4乾燥。在減壓下將溶劑去除,而以黏性液體之形式獲得光起始劑2.1g。
1H-NMR(CDCl3,δ ppm):2.10(s,36H),2.23(s,18H),3.42-3.91(m,100H),4.04-4.28(m,12H),6.78(s,12H),7.42-7.51(m,12H),7.54-7.62(m,6H),7.74-7.88(m,12H)
31P-NMR(CDCl3,δ ppm):18.2
在氮氣環境中,將甲苯100mL、三乙胺3.49g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯5.31g之溶液加熱至70℃。添加Polyol 4640(乙氧化季戊四醇,Perstorp Specialty Chemicals A.B.公司)1g,並將該溶液攪拌1.5小時。將該反應混合物冷卻至室溫,並加入去離子水100mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液100mL清洗1次且以水100mL清洗2次,最後以Na2SO4乾燥。在減壓下將溶劑去除,而以黏性液體之形式獲得光起始劑2.8g。
1H-NMR(CDCl3,δ ppm):2.00-2.15(m,24H),2.15-2.25(m,12H),3.23-3.72(m,19H),3.95-4.30(m,8H),6.72-
6.82(m,8H),7.38-7.65(m,12H),7.70-7.89(m,8H)
31P-NMR(CDCl3,δ ppm):18.2
在氮氣環境中,將甲苯25mL、三乙胺4.18g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯3.5g之溶液加熱至50℃。添加三羥甲基丙烷0.54g,並將該溶液攪拌1小時。將該反應混合物冷卻至室溫,並加入去離子水10mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液20mL清洗1次且以水20mL清洗2次,最後以Na2SO4乾燥。在減壓下將溶劑去除。藉由使用矽膠進行之快速管柱層析法(甲苯/乙酸乙酯,6:4)來將反應產物純化,而以黏性液體之形式獲得光起始劑1.5g。
1H-NMR(CDCl3,δ ppm):0.2-0.3(m,3H),1.19-1.38(m,2H),2.02-2.11(m,18H),2.28-2.38(m,9H),3.88-4.06
(m,6H),6.70-6.80(m,6H),7.36-7.54(m,9H),7.73-7.88(m,6H)
在氮氣環境中,將甲苯100mL、三乙胺3.49g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯5.31g在室溫攪拌1小時。添加4-胺甲基-1,8-辛二胺(美國Ascend Performance Materials LLC公司),並將該溶液攪拌1.5小時。反應結束時,加入去離子水100mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液100mL清洗1次且以水100mL清洗2次。然後將該有機溶液以Na2SO4乾燥,並在減壓下將溶劑去除。藉由使用矽膠進行之快速管柱層析法(二氯甲烷/甲醇,95:5)來將反應產物純化,而以黏性液體之形式獲得光起始劑1g。
1H-NMR(CDCl3,δ ppm):0.9-1.72(m,11H),1.90-2.04(m,12H),2.16-2.25(m,9H),2.78-3.52(m,6H),6.56-6.68(m,6H),7.26-7.88(m,15H)
在氮氣環境中,將甲苯25mL、三乙胺3.5g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯3.5g之溶液加熱至60℃。添加季戊四醇0.5g,並將該溶液攪拌1小時。將該反應混合物冷卻至室溫,並加入去離子水10mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液20mL清洗1次且以水20mL清洗2次,最後以Na2SO4乾燥。在減壓下將溶劑去除。藉由使用矽膠進行之快速管柱層析法(甲苯/乙酸乙酯,6:4;保留因子(Rf)0.7)來將反應產物純化,而以黏性液體之形式獲得光起始劑0.3g。
1H-NMR(CDCl3,δ ppm):1.85-1.96(m,24H),2.05-2.11(m,12H),4.02-4.12(m,8H),6.56-6.66(m,8H),7.21-7.51(m,12H),7.59-7.61(m,8H)
依照與實施例7相同的程序來製備光起始劑。藉由使用矽膠進行之快速管柱層析法(甲苯/乙酸乙酯,6:4;Rf 0.3)來將反應產物純化,而以黏性液體之形式獲得光起始劑0.5g。
1H-NMR(CDCl3,δ ppm):1.88-2.00(m,18H),2.05-2.08(m,9H),3.20(s,2H),3.82-4.00(m,6H),6.58-6.70(m,6H),7.24-7.40(m,6H),7.40-7.54(m,3H),7.60-7.75(m,6H)
在氮氣環境中,將三氯甲烷150mL、三乙胺3.49g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯
5.31g之溶液加熱至50℃。添加三乙醇胺0.4g,並將該溶液攪拌2小時。將該反應混合物冷卻至室溫,並加入去離子水10mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液100mL清洗3次且以水100mL清洗2次,最後以Na2SO4乾燥。在減壓下使溶劑蒸發。藉由使用矽膠進行之快速管柱層析法(二氯甲烷/甲醇,9:1)來將反應產物純化,而以黏性液體之形式獲得光起始劑0.5g。
1H-NMR(CDCl3,δ ppm):1.98(s,18H),2.14(s,9H),3.08-3.22(m,4H),3.97-4.15(m,4H),6.68(s,6H),7.27-7.39(m,6H),7.41-7.51(m,3H),7.61-7.76(m,6H).
在氮氣環境中,將三氯甲烷150mL、三乙胺10.5g及苯基(2,4,6-三甲基苯甲醯基)次膦醯氯15g之溶液加熱至50℃。添加Perstorp 3380(乙氧化三羥甲基丙烷,Perstorp Specialty Chemicals A.B.公司)5g,並將該溶液攪拌2小時。將該反應混合物冷卻至室溫,並加入去離子水200mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液200mL清洗3次且以水200mL清洗2次,並以Na2SO4乾燥。在減壓下將溶劑去除,並藉由使用矽膠進行之快速管柱層析法(二氯甲烷/甲醇,97:3)來將反應產物純化,而以黏性液體之形式獲得光起始劑7.35g。
1H-NMR(CDCl3,δ ppm):0.64-0.82(m,3H),1.20-1.38(m,2H),2.02(s,18H),2.19(s,9H),3.11-3.63(m,30H),3.80-4.6(m,7H),6.72(s,6H),7.32-7.58(m,9H),7.68-7.82(m,6H)
在氮氣環境中,將三氯甲烷10mL、三乙胺56.67mg及雙(2,4,6-三甲基苯甲醯基)次膦醯氯(依照WO2014/095724(BASF A.G.公司)所製備)210mg之溶液加熱至50℃。添加86mg的Aionico GL/609,並將該溶液攪拌1小時。將該反應混合物冷卻至室溫,並加入去離子水5mL。將有機相分離,並將該有機相以NaHCO3之飽和水溶液5mL清洗1次且以水5mL清洗2次,並以Na2SO4乾燥,並在減壓下使溶劑蒸發。藉由使用矽膠進行之快速管柱層析法(二氯甲烷/甲醇,9:1)來將反應產物純化,而獲得光起始劑0.1g。
1H-NMR(CDCl3,δ ppm):2.15(s,18H),2.26(s,36H),3.42-3.89(m,40H),6.72(s,12H)
使實施例1~6之光起始劑,以使濃度成為4wt%之方式溶於Ebecryl 605與Ebecryl 350(Allnex公司)的99.5:0.5w/w之混合物中,而製備本發明之光硬化性組成物。
作為比較例,是使用包含4wt%的Lucirin TPO-L(BASF AG公司)之光硬化性組成物。
將各個光硬化性組成物放置於FT-IR
分光光度計(FT-IR 430,Jasco公司)的樣品槽中,並暴露在不同光源(160W汞燈及發出400nm的光之9000mW/cm2的LED)中,該光源是設定成:與樣品之間的距離為65mm、角度為30°。
IR光譜是在暴露期間以固定的時間間
隔來進行測定,且使用IR軟體測得在1408cm-1的峰值面積經時地減少,該峰值面積是顯示出丙烯酸雙鍵。由此能夠對聚合度甚至是光起始劑之效率進行定量。
表2是表示經時的聚合%。表3是表示
針對每個配方中之光活性基的數目進行校正後之經時的聚合%。
表2及3之結果證明本發明之多功能單
及雙醯基膦氧化物之高反應性、尤其是考慮到每個光活性基之反應性(表3)。此等性能是與下述文獻揭示之先前技術的光起始劑具有同等的效能:US2012/0046376(表8及9)、US 7,166,647(表1)及US 7,354,957(第14欄第44-54行)、以及Macromol.Chem.Phys.208,2007,1694-1706(表4及5)及J.Photochem.Photobio.A:Chem.159,2003,103-114(表5)。
藉由使實施例1~5之光起始劑,以使濃度成為5.0wt%之方式分別溶於用於噴墨列印之青藍色墨水中,而製備用於測試之光硬化性組成物。
作為比較例,是使用包含5wt%的
Lucirin TPO-L(BASF A.G.公司)之光硬化性組成物。
將該光硬化性組成物放置於FT-IR分
光光度計(FT-IR 430,Jasco公司)的樣品槽中,並暴露在LED光源(400nm的9000mW/cm2)中,該光源是設定成:與樣品之間的距離為65mm、角度為30°。
IR光譜是在暴露期間以固定的時間間
隔來進行測定,且使用IR軟體測得在1408cm-1的峰值面積經時地減少,該峰值面積是顯示出丙烯酸雙鍵。由此能夠對聚合度甚至是光起始劑之效率進行定量。
結果是表示於表4中,該結果是以經時
的聚合%來表示。
藉由使實施例1~5之光起始劑,以使
濃度成為6.0wt%之方式分別溶於白色著色系統中,而製備用於測試之光硬化性組成物,該白色著色系統包含:經苯乙烯稀釋之不飽和聚苯乙烯、及20wt%的二氧化鈦。
使用機械攪拌機來使所得之組成物均質
化,並藉由薄膜塗抹器(film applicator)(Erichsen公司,Quadruple Film Applicator,Model 360)將該組成物以使厚度成為100μm之方式供給至玻璃基材(20cm×10cm)上。藉由在30℃晾乾(flashing-off)5分鐘來將溶劑去除,然後以10m/min的線速度來使薄膜暴露在鎵燈(120W/cm)中。
作為比較例,是使用包含6wt%的
Lucirin TPO-L(BASF A.G.公司)之光硬化性白色組成物。
藉由依照標準方法ASTM
D4366(König擺)測定厚度,並依照White Berger索引且使用色彩指南45/0(BYK公司)測定顏色安定性,來評估光起始劑之性能。
在測定性能前,硬化後之薄膜是置於下
述條件下:在室溫在黑暗中12小時。
結果是表示於表5中。
本發明之多功能單及雙醯基膦氧化物,在經著色而成之組成物中,亦顯示與Lucirin TPO-L同等或更高的反應性。本發明之多功能單及雙醯基膦氧化物,亦顯示與單功能起始劑同等的顏色安定性(無黃變)。
Claims (10)
- 一種式I之光起始劑:
- 如請求項1所述之式I之光起始劑,其中,式I中,m+n在3~8之間。
- 如請求項1所述之式I之光起始劑,其中,式I中,m+n在3~6之間。
- 如請求項1所述之式I之光起始劑,其中,式I中,R1為苯基、2,6-二氯苯基、2,4,6-三氯苯基、2,6-二甲基苯基、2,4,6-三甲基苯基、2,6-二乙基苯基、2,6-二甲氧基苯基、2,6-二乙氧基苯基、α-萘基、2,6-二硝基苯基、2,6-二甲基環己基、2,6-二乙基環己基、2,6-二甲氧基環己基、2,6-二乙氧基環己基、或2,6-二氯環己基、三級丁基、戊基、己基、庚基、辛基、及2-乙基己基。
- 如請求項1所述之式I之光起始劑,其中,式I中,R2為R1-(C=O)-、甲基、乙基、丙基、異丙基、正丁基、二級丁基、三級丁基、戊基、己基、2-乙基己基、苯基、二甲苯基、4-聯苯基、2-氯苯基、3-氯苯基或4-氯苯基、2,4-二氯苯基、2-甲基苯基、3-甲基苯基或4-甲基苯基、2,4-二甲基苯基、2-乙基苯基、3-乙基苯基或4-乙基苯基、2-甲氧基苯基、3-甲氧基苯基或4-甲氧基苯基、2,4-二甲氧基苯基、2-乙氧基苯基、3-乙氧基苯基或4-乙氧基苯基、α-萘基、甲基萘基、氯 萘基、乙氧基萘基、及2-硝基苯基或4-硝基苯基。
- 如請求項1所述之式I之光起始劑,其中,G-(A-H)m+n是選自多元醇之單體、寡聚物、聚合物及該等之混合物。
- 一種光硬化性組成物,其包含:a)0.05至20重量%的至少一種的式I之光起始劑;及b)30至99.9重量%的至少一種乙烯性不飽和化合物;
- 如請求項7所述之光硬化性組成物,其包含:a)0.2至10重量%的至少一種的式I之光起始劑;及b)50至98.9重量的至少一種乙烯性不飽和化合物。
- 如請求項7所述之光硬化性組成物,其進而包含:c)0.5至15重量%的另一種光起始劑。
- 如請求項7所述之光硬化性組成物,其進而包含:d)0.05至12重量%的光敏化劑。
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JP6599446B2 (ja) | 2019-10-30 |
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TWI651328B (zh) | 2019-02-21 |
JP2017522364A (ja) | 2017-08-10 |
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US20170240659A1 (en) | 2017-08-24 |
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