CN113056528A - 新型光引发剂 - Google Patents
新型光引发剂 Download PDFInfo
- Publication number
- CN113056528A CN113056528A CN201980077851.7A CN201980077851A CN113056528A CN 113056528 A CN113056528 A CN 113056528A CN 201980077851 A CN201980077851 A CN 201980077851A CN 113056528 A CN113056528 A CN 113056528A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- photoinitiator
- heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000000524 functional group Chemical group 0.000 claims abstract description 4
- 230000005855 radiation Effects 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 238000007641 inkjet printing Methods 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
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- -1 phosphate ester Chemical class 0.000 description 20
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- 238000004458 analytical method Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001479434 Agfa Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZWZREAICFWEXQH-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(Cl)(=O)C1=CC=CC=C1 ZWZREAICFWEXQH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
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- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical class OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
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- 125000004434 sulfur atom Chemical group 0.000 description 2
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
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- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical class COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
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- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
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- 230000036211 photosensitivity Effects 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- 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)
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- 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)
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- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
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- 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)
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F216/04—Acyclic compounds
- C08F216/08—Allyl alcohol
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- C09D11/00—Inks
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- 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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Abstract
选自酰基氧化膦、α‑羟基‑酮和α‑氨基‑酮的光引发剂,其特征在于所述光引发剂包括至少一个脂肪族二硫化物作为官能团。
Description
技术领域
本发明涉及新型光引发剂及其在用于制造印刷电路板的可辐射固化的喷墨油墨中的用途。
背景技术
印刷电路板(PCB)的生产工作流程正逐渐从标准工作流程向数字工作流程转变,以减少方法步骤的量并降低PCB生产的成本和环境影响,尤其是对于小批量生产。
喷墨是PCB制造方法的不同步骤中(从焊接掩模上的防蚀涂层到图案印刷)的优选的数字制造技术之一。优选的喷墨油墨是可UV固化的喷墨油墨。
在例如EP-A 2725075 (AGFA)和US 7845785 (MARKEM-IMAJE)中已经公开了喷墨印刷方法和喷墨油墨用于图案印刷,并且在例如EP-A 2809735 (AGFA)和EP-A 3000853(AGFA)中已经公开了喷墨印刷方法和喷墨油墨用于在铜表面上施加防蚀涂层。
在例如EP-A 1543704 (AVECIA)和EP-A 1624001 (TAIYO INK MANUFACTURING)中还已经公开了喷墨印刷方法和喷墨油墨用于施加焊接掩模。
在不同的生产步骤中,喷墨油墨对不同基材的粘合是至关重要的。为了使粘合性能最大化,通常需要助粘剂。
现有技术中已经公开了几类助粘剂,它们中的大多数本质上是酸性的。
WO2004/026977 (AVECIA)公开了一种非水性耐蚀刻喷墨油墨,其包含1-30重量%的含有一个或多个酸性基团的丙烯酸酯官能单体作为在剥离期间的助粘剂和助溶解剂。
WO2004/106437 (AVECIA)公开了一种耐蚀刻喷墨油墨,其优选包含(甲基)丙烯酸酯酸性助粘剂,例如(甲基)丙烯酸酯化的羧酸、(甲基)丙烯酸酯化的磷酸酯和(甲基)丙烯酸酯化的磺酸。
在着色的***(例如焊接掩模油墨和图案油墨)中,酸性助粘剂通常干扰颜料分散,导致油墨有限的稳定性。这可能对工业印刷***在PCB印刷中的可靠性具有影响,导致不可接受的生产能力损失。
因此,还需要设计无需酸性助粘剂的可喷射的可辐射固化的制剂。
发明内容
本发明的目的是提供新型光引发剂及其在用于PCB制造的可辐射固化的喷墨油墨中的用途,其特征在于对各种基材良好的粘合,同时保持可辐射固化的喷墨油墨优异的喷射和稳定性性能。
本发明的目的通过根据权利要求1所述的光引发剂实现。
已经发现包含如在权利要求1所定义的光引发剂的可辐射固化的组合物对各种基材具有优异的粘合,而无需酸性助粘剂。
本发明的其它目的将从下文的描述中变得显而易见。
具体实施方式
定义
在例如单官能可聚合化合物中的术语“单官能”是指可聚合化合物包括一个可聚合基团。
在例如双官能可聚合化合物中的术语“双官能”是指可聚合化合物包括两个可聚合基团。
在例如多官能可聚合化合物中的术语“多官能”是指可聚合化合物包括多于两个可聚合基团。
术语“烷基”是指烷基中对于每个碳原子数可能的所有变体,即,甲基;乙基;对于三个碳原子:正丙基和异丙基;对于四个碳原子:正丁基、异丁基和叔丁基;对于五个碳原子:正戊基、1,1-二甲基-丙基、2,2-二甲基丙基和2-甲基-丁基等。
除非另有说明,否则取代或未取代的烷基优选为C1-C6-烷基。
除非另有说明,否则取代或未取代的烯基优选为C2-C6-烯基。
除非另有说明,否则取代或未取代的炔基优选为C2-C6-炔基。
除非另有说明,否则取代或未取代的烷芳基优选为包括一个、两个、三个或更多个C1-C6烷基的苯基或萘基。
除非另有说明,否则取代或未取代的芳烷基优选为包括苯基或萘基的C7-C20-烷基。
除非另有说明,否则取代或未取代的芳基优选为苯基或萘基。
除非另有说明,否则取代或未取代的杂芳基优选为被一个、两个或三个氧原子、氮原子、硫原子、硒原子或其组合取代的五元或六元环。
在例如取代的烷基中的术语“取代的”是指烷基可以被除了通常存在于这样的基团中的原子(即,碳和氢)以外的其它原子取代。例如,取代的烷基可以包括卤素原子或硫醇基。未取代的烷基仅含有碳和氢原子。
除非另有说明,否则取代的烷基、取代的烯基、取代的炔基、取代的芳烷基、取代的烷芳基、取代的芳基和取代的杂芳基优选被选自以下的一个或多个成分取代:甲基、乙基、正丙基、异丙基、正丁基、异丁基和叔丁基、酯、酰胺、醚、硫醚、酮、醛、亚砜、砜、磺酸酯、磺酰胺、-Cl、-Br、-I、-OH、-SH、-CN和-NO2。
光引发剂
根据本发明的光引发剂选自酰基氧化膦、α-羟基-酮和α-氨基-酮,被至少一个脂肪族二硫化物进一步官能化。
脂肪族二硫化物定义为其中两个硫原子键合到饱和碳原子的二硫化物,意味着所述碳原子不是芳族或杂芳族环、双键或三键的一部分。
在优选的实施方案中,光引发剂具有根据式I的化学结构,
其中
R1、R3和R5独立地选自氢、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和OR8,
R2和R4独立地选自氢、酰胺、磺酰胺、氨基甲酸酯、脲基、酯和醚,
R6选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和OR8,
R7选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和酰基,
R8选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基和取代或未取代的芳基或杂芳基,
条件是R1至R8中的至少一个被脂肪族二硫化物取代。
在特别优选的实施方案中,光引发剂具有根据式II的化学结构,
其中
L1表示包含不超过20个碳原子的二价连接基团;
R10和R11独立地选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基和取代或未取代的芳基或杂芳基;
R12表示取代或未取代的烷基或取代或未取代的芳烷基;
X选自OH和NR13R14;
R13和R14独立地选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基和取代或未取代的芳烷基;
R10和R11可以表示形成5-8元环所必需的原子;
R13和R14可以表示形成5-8元环所必需的原子;
L1和R12可以表示形成5-8元环所必需的原子。
根据式II的光引发剂优选为包含两个光引发剂部分的对称的二硫化物。
在另一个优选的实施方案中,光引发剂具有根据式III的化学结构,
其中
R15选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和酰基,
L2表示包含不超过20个碳原子,更优选包含不超过10个碳原子,最优选包含不超过6个碳原子的二价连接基团。
R15优选表示取代或未取代的芳基。
在进一步优选的实施方案中,光引发剂具有根据式IV的化学结构,
其中
R16选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和OR18,
R17选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和酰基,
R18选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基和取代或未取代的芳基或杂芳基,
L3表示包含不超过20个碳原子的二价连接基团。
R16优选选自取代或未取代的芳基和OR18。
R17优选选自取代或未取代的芳基和酰基。
L3优选包含选自酰胺、氨基甲酸酯和脲基的至少一个官能团。
根据本发明的光引发剂的典型实例在下表1中给出。
表1
可辐射固化的喷墨油墨
可辐射固化的喷墨油墨包含可聚合化合物和如上所述的光引发剂。
可辐射固化的喷墨油墨可以进一步包含着色剂、聚合物分散剂、聚合抑制剂、阻燃剂或表面活性剂。
可辐射固化的喷墨油墨可以通过任何类型的辐射而固化,例如通过电子束辐射,但优选通过UV辐射,更优选通过来自UV LED的UV辐射而固化。因此,可辐射固化的喷墨油墨优选为可UV固化的喷墨油墨。
对于可靠的工业喷墨印刷,可辐射固化的喷墨油墨的粘度优选在45℃下不超过20mPa.s,更优选在45℃下在1-18 mPa.s之间,并且最优选在45℃下在4-14 mPa.s之间,均在1000 s-1剪切速率下。
优选的喷射温度在10-70℃之间,更优选在20-55℃之间,并且最优选在25-50℃之间。
为了良好的图像质量和粘合性,可辐射固化的喷墨油墨的表面张力优选在25℃下在18-70 mN/m范围内,更优选在25℃下在20-40 mN/m范围内。
可聚合化合物
可聚合化合物优选为可自由基聚合的化合物。
可自由基聚合的化合物可以是单体、低聚物和/或预聚物。单体也称为稀释剂。
这些单体、低聚物和/或预聚物可以具有不同程度的官能度,即不同量的可自由基聚合的基团。
可以使用包括单官能、双官能、三官能和更高官能的单体、低聚物和/或预聚物的组合的混合物。可辐射固化的喷墨油墨的粘度可以通过改变单体与低聚物之间的比率来调节。
在优选的实施方案中,单体、低聚物或聚合物包括至少一个丙烯酸酯基团作为可聚合基团。
优选的单体和低聚物为在EP-A 1911814的段落[0106]至[0115]中所列的那些。
在优选的实施方案中,可辐射固化的喷墨油墨包含含有乙烯基醚基团和丙烯酸酯或甲基丙烯酸酯基团的单体。这样的单体公开于EP-A 2848659的段落[0099]至[0104]中)。含有乙烯基醚基团和丙烯酸酯基团的特别优选的单体为丙烯酸2-(2-乙烯氧基乙氧基)乙酯。
当用于形成焊接掩模时,可聚合化合物优选选自丙烯酰基吗啉、环状三甲基丙烯甲醛丙烯酸酯、丙烯酸异冰片酯、二丙二醇二丙烯酸酯、三羟甲基丙烷三丙烯酸酯和丙烯酸2-(乙烯基乙氧基)乙酯。
当可辐射固化的喷墨油墨用于形成防蚀涂层时,优选的可聚合化合物公开于WO2013/113572的段落[0056]至[0058],WO2015/132020的段落[0031]至[0052],或WO2016/050504的段落[0028]至[0066]中。
酚类化合物
可辐射固化的喷墨油墨优选包含酚类化合物,更优选包含至少两个酚基的酚类化合物。酚类化合物可以包含两个、三个、四个或更多个酚基。
优选的酚类化合物包含两个酚基。
特别优选的酚类化合物具有根据式II的结构:
其中,
R17和R18独立地选自氢原子、取代或未取代的烷基、羟基和取代或未取代的烷氧基,
Y选自CR19R20、SO2、SO、S、O和CO,
R19和R20独立地选自氢原子、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的烷芳基、取代或未取代的芳烷基、取代或未取代的(杂)芳基,
R19和R20可以表示形成5-8元环所必需的原子。
Y优选为CR19R20或SO2,R19和R20优选表示氢原子或烷基。
在另一个优选的实施方案中,酚类化合物为包含至少两个酚基的聚合物。优选地,包含至少两个酚基的聚合物为支化的或超支化的聚合物。
优选的包含至少两个酚基的聚合物为酚醛树脂,即酚醛清漆(novolac)或甲阶酚醛树脂(resole)。
酚醛树脂为酚类化合物与醛或酮的反应产物。可以使用的酚类是:苯酚、邻甲酚、对甲酚、间甲酚、2,4-二甲酚、3,5-二甲酚或2,5-二甲酚。可以使用的醛为甲醛、乙醛或丙酮。
用于酚醛清漆制备的最广泛使用的方法是苯酚/甲酚和甲醛的酸催化的一步合成,其得到树脂的统计结构(参见以下反应方案)。
通常,将盐酸、硫酸、对甲苯硫酸或草酸用作催化剂。在常规酚醛清漆树脂中通常使用各种比例的甲醛和苯酚/甲酚。较高的苯酚含量增加支化度,而反应可以在邻位和对位发生。对于具有较高对甲酚含量的树脂,由于对位被甲基的存在所堵塞,获得更多的线性聚合物。
苯酚和甲醛的酚醛清漆共聚物具有高支化度,因为反应在邻位和对位两者发生。为了降低粘度,优选高支化度和/或低分子量。对于甲酚酚醛清漆,与邻甲酚和对甲酚相比,使用间甲酚可以更容易地得到高分子量。
酚醛树脂也可以在碱催化的反应中制备,这导致甲阶酚醛树脂的形成。甲阶酚醛树脂是也具有羟甲基的酚类聚合物。
为了并入焊接掩模喷墨油墨中,优选酚醛清漆树脂以获得足够的油墨稳定性,因为酚醛清漆树脂仅在高温(>150℃)下是反应性的。甲阶酚醛树脂可能在较低温度下已经反应,并且由于羟甲基的存在可能导致喷墨油墨的耐化学性较差。
如在US5554719和US2005250042中所公开的,可以使用4-羟基苯基甲基甲醇制备具有至少两个酚基的更明确定义的支化的聚合物。由4-羟基苯基甲基甲醇制备的具有至少两个酚基的特别优选的支化的聚合物已由Du Pont Electronic Polymers开发,并由Hydrite Chemical Company以商品名PB-5 (CASRN 166164-76-7)供应。
根据本发明的酚类化合物的实例在表2中给出,而不限于此。
表2
具有至少两个酚基的聚合物的典型实例在下表3中给出,而不限于此。
表3
相对于喷墨油墨的总重量,酚类化合物的量优选在0.5-20重量%之间,更优选在1-15重量%之间,最优选在2.5-10重量%之间。
着色剂
可辐射固化的喷墨可以是基本上无色的喷墨油墨或者可以包括至少一种着色剂。例如,当喷墨油墨用作防蚀涂层时,着色剂使得临时掩模对于导电图案的制造商清晰可见,允许视觉检查质量。当喷墨油墨用于施加焊接掩模时,它通常含有着色剂。焊接掩模的优选颜色是绿色,然而也可以使用其它颜色,例如黑色或红色。
着色剂可以是颜料或染料,但优选为颜料。
有色颜料可以选自由HERBST, Willy等人, Industrial Organic Pigments,Production, Properties, Applications, 第3版.Wiley - VCH, 2004, ISBN3527305769所公开的那些。
合适的颜料公开于WO2008/074548的段落[0128]至[0138]。
喷墨油墨中的颜料颗粒应足够小,以允许油墨自由流动通过喷墨印刷装置,尤其是在喷嘴处。还期望使用小颗粒以获得最大的颜色强度并减缓沉降。最优选地,平均颜料粒度不大于150 nm。颜料颗粒的平均粒度优选基于动态光散射原理用BrookhavenInstruments Particle Sizer BI90Plus来确定。
在PCB中,焊接掩模通常具有蓝色或绿色。蓝色颜料优选为酞菁系列中的一种。蓝色颜料的实例为C.I.颜料蓝1、15、15:1、15:2、15:3、15:4、15:6、16、24和60。
绿色颜料通常是蓝色和黄色或橙色颜料的混合物或者可以是绿色颜料或染料本身,例如卤代酞菁,例如铜或镍溴化酞菁。
在优选的实施方案中,基于可辐射固化的喷墨油墨的总重量,着色剂以0.2-6.0重量%,更优选0.5-2.5重量%的量存在。
聚合物分散剂
如果可辐射固化的喷墨中的着色剂为颜料,则可辐射固化的喷墨油墨优选含有分散剂,更优选聚合物分散剂,用于分散颜料。
合适的聚合物分散剂为两种单体的共聚物,但它们可以含有三种、四种、五种或甚至更多种单体。聚合物分散剂的性质取决于单体的性质和它们在聚合物中的分布两者。共聚物分散剂优选具有以下聚合物组成:
•统计聚合的单体(例如单体A和B聚合成ABBAABAB);
•交替聚合的单体(例如单体A和B聚合成ABABABAB);
•梯度(递变)聚合的单体(例如单体A和B聚合成AAABAABBABBB);
•嵌段共聚物(例如单体A和B聚合成AAAAABBBBBB),其中各嵌段的嵌段长度(2、3、4、5或甚至更多)对于聚合物分散剂的分散能力是重要的;
•接枝共聚物(接枝共聚物由聚合物主链和与主链相连的聚合物侧链组成);和
•这些聚合物的混合形式,例如嵌段梯度共聚物。
合适的聚合物分散剂列于EP-A 1911814中“分散剂”部分,更具体地[0064]至[0070]和[0074]至[0077]。
聚合物分散剂的商品实例如下:
• DISPERBYKTM分散剂,可从BYK CHEMIE GMBH获得;
• SOLSPERSETM分散剂,可从NOVEON获得;
• TEGOTM DISPERSTM分散剂,来自EVONIK;
• EDAPLANTM分散剂,来自MÜNZING CHEMIE;
• ETHACRYLTM分散剂,来自LYONDELL;
• GANEXTM分散剂,来自ISP;
• DISPEXTM和EFKATM分散剂,来自CIBA SPECIALTY CHEMICALS INC;
• DISPONERTM分散剂,来自DEUCHEM;和
• JONCRYLTM分散剂,来自JOHNSON POLYMER。
光引发剂和光引发***
可辐射固化的喷墨含有如上所述的光引发剂。然而,喷墨油墨可以含有其它光引发剂。
通常,所谓的共引发剂与光引发剂组合使用。共引发剂和光引发剂的这样的组合称为光引发***。
合适的光引发剂公开于CRIVELLO, J.V.等人,Photoinitiators for FreeRadical Cationic and Anionic Photopolymerization.第2版.由BRADLEY, G编辑.London, UK: John Wiley and Sons Ltd, 1998.第276-293页。
为了进一步增加光敏性,可辐射固化的喷墨可以另外含有共引发剂。
共引发剂的合适实例可以分类为三组:
(1)叔脂肪胺,例如甲基二乙醇胺、二甲基乙醇胺、三乙醇胺、三乙胺和N-甲基吗啉;
(2)芳族胺,例如对二甲基氨基苯甲酸戊酯、4-(二甲基氨基)苯甲酸2-正丁氧基乙酯、苯甲酸2-(二甲基氨基)-乙酯、4-(二甲基氨基)苯甲酸乙酯和4-(二甲基氨基)苯甲酸2-乙基己酯;和
(3) (甲基)丙烯酸酯化的胺,例如二烷基氨基烷基(甲基)丙烯酸酯(例如二乙基氨基乙基丙烯酸酯)或N-吗啉代烷基-(甲基)丙烯酸酯(例如N-吗啉代乙基-丙烯酸酯)。优选的共引发剂为氨基苯甲酸酯。
可辐射固化的喷墨油墨优选包括(扩散受阻的)共引发剂,其量为可辐射固化的喷墨油墨总重量的0.1-20重量%,更优选其量为可辐射固化的喷墨油墨总重量的0.5-15重量%,最优选其量为可辐射固化的喷墨油墨总重量的1-10重量%。
聚合抑制剂
可辐射固化的喷墨油墨可以含有至少一种抑制剂,用于改进油墨的热稳定性。
合适的聚合抑制剂包括酚型抗氧化剂、受阻的胺光稳定剂、磷型抗氧化剂、通常用于(甲基)丙烯酸酯单体的氢醌单甲醚和氢醌。还可以使用叔丁基儿茶酚、连苯三酚、2,6-二叔丁基-4-甲基苯酚(=BHT)和吩噻嗪。
合适的商品抑制剂为例如SumilizerTM GA-80、SumilizerTM GM和SumilizerTM GS,由Sumitomo Chemical Co. Ltd. 生产;GenoradTM 16、GenoradTM18和GenoradTM 22,来自Rahn AG;IrgastabTMUV10和IrgastabTM UV22、TinuvinTM 460和CGS20,来自Ciba SpecialtyChemicals;FlorstabTM UV系列(UV-1、UV-2、UV-5和UV-8),来自Kromachem Ltd;AdditolTMS系列(S100、S110、S120和S130)和PTZ,来自Cytec Solvay Group。
抑制剂优选为可聚合的抑制剂。
由于这些聚合抑制剂的过量加入可能降低固化速度,优选在共混之前确定能够防止聚合的量。聚合抑制剂的量优选低于总可辐射固化的喷墨油墨的5重量%,更优选低于总可辐射固化的喷墨油墨的3重量%。
表面活性剂
可辐射固化的喷墨可以含有至少一种表面活性剂,但优选不存在表面活性剂。
表面活性剂可以是阴离子表面活性剂、阳离子表面活性剂、非离子表面活性剂或两性离子表面活性剂,并且基于可辐射固化的喷墨油墨的总重量,通常以小于1重量%的总量加入。
合适的表面活性剂包括氟化的表面活性剂、脂肪酸盐、高级醇的酯盐、烷基苯磺酸盐、磺基琥珀酸酯盐和高级醇的磷酸酯盐(例如十二烷基苯磺酸钠和二辛基磺基琥珀酸钠)、高级醇的环氧乙烷加合物、烷基酚的环氧乙烷加合物、多元醇脂肪酸酯的环氧乙烷加合物和乙炔二醇(acetylene glycol)及其环氧乙烷加合物(例如聚氧乙烯壬基苯基醚和SURFYNOLTM 104、104H、440、465和TG,可从AIR PRODUCTS & CHEMICALS INC. 获得)。
优选的表面活性剂选自含氟表面活性剂(例如氟化的烃)和有机硅表面活性剂。有机硅表面活性剂优选为硅氧烷,并且可以是烷氧基化的、聚醚改性的、聚醚改性的羟基官能的、胺改性的、环氧改性的和其它改性或其组合。优选的硅氧烷为聚合的,例如聚二甲基硅氧烷。
优选的商品有机硅表面活性剂包括BYKTM 333和BYKTM UV3510,来自BYK Chemie;以及Tego Rad 2100,来自Evonik Industries。
在优选的实施方案中,表面活性剂为可聚合化合物。
优选的可聚合的有机硅表面活性剂包括(甲基)丙烯酸酯化的有机硅表面活性剂。最优选地,(甲基)丙烯酸酯化的有机硅表面活性剂为丙烯酸酯化的有机硅表面活性剂,因为丙烯酸酯比甲基丙烯酸酯更具有反应性。
在优选的实施方案中,(甲基)丙烯酸酯化的有机硅表面活性剂为聚醚改性的(甲基)丙烯酸酯化的聚二甲基硅氧烷或聚酯改性的(甲基)丙烯酸酯化的聚二甲基硅氧烷。
优选地,基于可辐射固化的喷墨油墨的总重量,表面活性剂以0-3重量%的量存在于可辐射固化的喷墨油墨中。
阻燃剂
优选的阻燃剂为无机阻燃剂,例如三水合氧化铝和勃姆石,以及有机磷化合物例如有机磷酸酯(例如磷酸三苯酯(TPP)、间苯二酚双(二苯基磷酸酯) (RDP)、双酚A二苯基磷酸酯(BADP)和磷酸三甲苯酯(TCP));有机膦酸酯(例如甲基膦酸二甲酯(DMMP));和有机次膦酸盐(例如二甲基次膦酸铝)。
其它优选的有机磷化合物公开于US8273805中。
喷墨油墨的制备
着色的可辐射固化的喷墨油墨的制备是本领域技术人员公知的。优选的制备方法公开于WO2011/069943的段落[0076]至[0085]中。
印刷电路板的制造
根据本发明的制造印刷电路板(PCB)的方法包括喷墨印刷步骤,其中将如上所述的可辐射固化的喷墨油墨喷射并固化在基材上。
根据优选的实施方案,制造PCB的方法包括喷墨印刷步骤,其中在金属表面(优选铜表面)上提供防蚀涂层。
通过在金属表面上喷射并固化可辐射固化的喷墨油墨,在金属表面上提供防蚀涂层,从而形成金属表面的受保护区域。然后通过蚀刻从金属表面的未受保护的区域去除金属。在蚀刻之后,从金属表面的受保护区域去除至少部分防蚀涂层。
金属表面优选为附着于基材的金属箔或片材。
对于结合到金属片材的基材的类型没有实际限制,只要它是非导电的。基材可以由陶瓷、玻璃或塑料(例如聚酰亚胺)制成。
金属片材通常厚度在9-105 µm之间。
对金属表面的性质没有限制。金属表面优选由铜、铝、镍、铁、锡、钛或锌组成,但也可以是包括这些金属的合金。在非常优选的实施方案中,金属表面由铜制成。铜具有高导电性,并且是相对便宜的金属,使得它非常适合于制造印刷电路板。
该方法还可以用于制造装饰性蚀刻的金属面板。
所用的金属表面可以选自上述金属,用于其中制备导电图案的实施方案。在这种情况下,优选使用实心金属面板。然而,也可以使用附着于基材的金属箔。对于结合到金属箔的基材的类型没有实际限制。基材可以由陶瓷、玻璃或塑料制成,或者甚至由第二(较便宜的)金属板制成。金属也可以是合金。
这样的装饰性金属面板可以用于除了纯装饰性之外的目的,例如提供信息。例如,铝铭牌(其中将耐蚀刻的可辐射固化的喷墨油墨作为信息(例如人名或公司名)印刷,然后去除以在垫蚀刻背景上产生有光泽的闪亮的名称)也认为是包括装饰性元素的装饰性金属面板。蚀刻引起金属表面的光学性质的变化,例如光泽的变化。在从金属表面去除固化的可辐射固化的喷墨油墨之后,在蚀刻的和非蚀刻的金属表面之间产生美学作用。
在喷墨印刷方法的优选的实施方案中,在印刷可辐射固化的喷墨油墨之前清洁金属表面。当用手处理金属表面并且不戴手套时,这是特别期望的。清洁去除可能干扰可辐射固化的喷墨油墨对金属表面的粘合的灰尘颗粒和油脂。在PCB中,通常通过微蚀刻来清洁铜。去除铜的氧化物层,并且引入粗糙度以改进粘合。
喷墨方法也可以用于制造装饰性蚀刻的玻璃面板。这样的方法例如公开于WO2013/189762 (AGC)中。
根据另一优选的实施方案,制造PCB的方法包括喷墨印刷步骤,其中提供焊接掩模。
通常在含有导电图案的介电基材上通过喷射并固化可辐射固化的喷墨油墨来提供焊接掩模。
优选对喷射并固化的可辐射固化的喷墨油墨施加热处理。热处理优选在80℃至250℃之间的温度下进行。该温度优选不低于100℃,更优选不低于120℃。为了防止焊接掩模的炭化,该温度优选不高于200℃,更优选不高于160℃。
热处理通常进行15-90分钟之间。
热处理的目的是进一步增加焊接掩模的聚合度。
电子装置的介电基材可以是任何非导电的材料。基材通常是纸/树脂复合材料或树脂/玻璃纤维复合材料、陶瓷基材、聚酯或聚酰亚胺。
导电图案通常由常规用于制备电子装置的任何金属或合金制成,例如金、银、钯、镍/金、镍、锡、锡/铅、铝、锡/铝和铜。导电图案优选由铜制成。
在两个实施方案中,通过将油墨暴露于光化辐射(例如电子束或紫外(UV)辐射),可以固化可辐射固化的喷墨油墨。优选地,可辐射固化的喷墨油墨通过UV辐射固化,更优选使用UV LED固化。
制造PCB的方法可以包括两个、三个或更多个喷墨印刷步骤。例如,该方法可以包括两个喷墨印刷步骤,其中在一个喷墨印刷步骤中在金属表面上提供防蚀涂层,并且其中在另一个喷墨印刷步骤中在含有导电图案的介电基材上提供焊接掩模。
第三喷墨印刷步骤可以用于图案印刷。
蚀刻
通过使用蚀刻剂来进行金属表面的蚀刻。蚀刻剂优选为pH<3或其中8<pH<10的水溶液。
在优选的实施方案中,蚀刻剂为pH小于2的酸性水溶液。酸性蚀刻剂优选包括选自硝酸、苦味酸、盐酸、氢氟酸和硫酸的至少一种酸。
本领域已知的优选的蚀刻剂包括Kalling's N°2、ASTM N° 30、Kellers蚀刻剂、Klemm's试剂、Kroll's试剂、Marble's试剂、Murakami's试剂、Picral和Vilella's试剂。
在另一个优选的实施方案中,蚀刻剂为pH不大于9的碱性水溶液。碱性蚀刻剂优选包括选自氨或氢氧化铵、氢氧化钾和氢氧化钠的至少一种碱。
蚀刻剂还可以含有金属盐,例如二氯化铜、硫酸铜、铁***和三氯化铁。
在PCB应用中,金属表面的蚀刻优选在数秒至几分钟,更优选5-200秒的时间框内进行。蚀刻优选在35℃至60℃之间的温度下进行。
在其它应用中,例如在制造装饰性金属面板中,金属表面的蚀刻时间可以大幅地更长,这取决于在蚀刻步骤期间必须去除的金属的类型和量。蚀刻时间可以大于15分钟、30分钟或甚至60分钟。
在其中蚀刻玻璃表面的方法中,蚀刻溶液优选为氢氟酸的水溶液。通常,蚀刻溶液的pH在0-5之间。
蚀刻之后优选用水冲洗以去除任何残余的蚀刻剂。
剥离
在蚀刻之后,必须从金属表面至少部分地去除固化的可辐射固化的喷墨油墨,使得例如电气装置或电子装置可以与剩余的金属表面(导电图案)接触,或者使得蚀刻的金属面板的装饰性特征变得完全可见。例如,电子元件(例如晶体管)必须能够与印刷电路板上的导电(铜)图案建立电接触。在优选的实施方案中,将固化的可辐射固化的喷墨油墨从金属表面完全去除。
在优选的实施方案中,通过碱性剥离浴去除固化的可辐射固化的喷墨油墨。这样的碱性剥离浴通常是pH>10的水溶液。
在另一个实施方案中,通过干脱层去除固化的可辐射固化的喷墨油墨。这种“干剥离”技术在制造印刷电路板的领域中目前是未知的,并且在制造方法中引入了若干生态和经济的优点。干剥离不仅消除对腐蚀性碱性剥离浴的需要及其固有的液体废物,而且允许更高的生产量。例如,通过使用粘合剂箔和辊对辊层压机脱层器,可以实施干剥离。首先将粘合剂箔以其粘合剂侧层压在存在于金属表面上的固化的可辐射固化的喷墨油墨上,并随后脱层,从而从金属表面去除固化的可辐射固化的喷墨油墨。通过辊对辊层压机脱层器的脱层可以在数秒内完成,而碱性剥离可能花费数分钟。
喷墨印刷装置
可辐射固化的喷墨油墨可以通过喷嘴以受控方式通过喷射小液滴的一个或多个印刷头喷射到相对于一个或多个印刷头移动的基材上。
用于喷墨印刷***的优选的印刷头为压电头。压电喷墨印刷基于当向其施加电压时压电陶瓷换能器的移动。电压的施加改变了印刷头中的压电陶瓷换能器的形状,产生空隙,然后用油墨填充该空隙。当再次去除电压时,陶瓷膨胀到其原始形状,从印刷头喷射墨滴。然而,根据本发明的喷墨印刷方法不限于压电喷墨印刷。可以使用其它喷墨印刷头,并且包括各种类型,例如连续型。
喷墨印刷头通常跨移动的受墨体表面在横向来回扫描。通常喷墨印刷头在返回的途中不印刷。双向印刷对于获得高面积生产量是优选的。另一种优选的印刷方法是通过“单程印刷方法”,其可以通过使用页宽喷墨印刷头或覆盖受墨体表面的整个宽度的多个交错的喷墨印刷头来进行。在单程印刷方法中,喷墨印刷头通常保持静止,而受墨体表面在喷墨印刷头下方传送。
固化装置
可辐射固化的喷墨油墨可以通过将它们暴露于光化辐射(例如电子束或紫外辐射)而固化。优选地,可辐射固化的喷墨油墨通过紫外辐射而固化,更优选使用UV LED固化。
在喷墨印刷中,固化装置可以与喷墨印刷机的印刷头组合布置,与其一起行进,使得可固化液体在喷射后非常短的时间内暴露于固化辐射。
在这样的布置中,除了UV LED之外,可能难以提供足够小的辐射源,该辐射源连接到印刷头并与印刷头一起行进。因此,可以使用静态固定辐射源,例如固化UV光源,其通过柔性辐射传导装置(例如光纤束或内部反射的柔性管)连接到辐射源。
或者,光化辐射可以从固定源通过包括在辐射头上的镜子的镜子布置而供应到辐射头。
辐射源也可以是跨待固化的基材横向延伸的细长的辐射源。它可以邻近印刷头的横向路径,使得由印刷头形成的图像的后续行逐步地或连续地在辐射源下方通过。
只要部分发射的光可以被光引发剂或光引发剂***吸收,任何紫外光源都可以用作辐射源,例如高压或低压汞灯、冷阴极管、黑光灯、紫外LED、紫外激光器和闪光灯。其中,优选的源是表现出具有主波长300-400 nm的相对长波长UV贡献的源。特别地,优选UV-A光源,因为其具有的减少的光散射导致更有效的内部固化。
UV辐射通常如下分类为UV-A、UV-B和UV-C:
• UV-A:400 nm至320 nm
• UV-B:320 nm至290 nm
• UV-C:290 nm至100 nm。
在优选的实施方案中,可辐射固化的喷墨油墨通过UV LED固化。喷墨印刷装置优选含有优选波长大于360 nm的一个或多个UV LED,优选波长大于380 nm的一个或多个UVLED,并且最优选波长为约395 nm的UV LED。
此外,可以连续地或同时地使用不同波长或照度的两个光源来固化油墨图像。例如,可以将第一UV源选择为富含UV-C(特别是在260 nm至200 nm的范围内)。第二UV源则可以富含UV-A,例如掺镓灯,或者是UV-A和UV-B两者都高的不同的灯。已经发现使用两种UV源具有优点,例如固化速度快和固化程度高。
为了促进固化,喷墨印刷装置通常包括一个或多个氧消耗单元。氧消耗单元放置了具有可调节位置和可调节惰性气体浓度的氮气或其它相对惰性气体(例如CO2)的覆盖层,以降低固化环境中的氧浓度。残余的氧水平通常保持低至200 ppm,但一般在200 ppm至1200 ppm的范围内。
实施例
材料
除非另有说明,否则在以下实施例中使用的所有材料都可容易地从标准来源(例如ALDRICH CHEMICAL Co.(比利时)和ACROS (比利时))获得。所用的水为去离子水。
光引发剂的制备
LC-MS分析
在AmaZonTM SL质谱仪(由Brüker Daltonics供应)上,使用Alltech Alltima C18(150 mm×3.2 mm)柱,在0.5 ml/min的流速下,在30℃的温度下和ESI作为电离技术,分析一些光引发剂。使用如下所述的梯度洗脱:
- 洗脱剂A:在水/甲醇(9/1)中的10 mmol乙酸铵
- 洗脱剂B:在甲醇中的10 mmol乙酸铵
洗脱时间(分钟) | 洗脱剂B% |
0 | 0 |
15 | 100 |
21 | 100 |
22 | 0 |
30 | 停止 |
INI-3的合成
如在DE10206117中所公开,制备[氯(苯基)磷酰基]-(2,4,6-三甲基苯基)甲酮(CASRN577956-23-2)。
根据以下反应方案制备光引发剂INI-3。
将15.33 g (0.05 mol) [氯(苯基)磷酰基]-(2,4,6-三甲基苯基)甲酮溶解于60ml二氯甲烷中。经5分钟加入3.08 g (0.02 mol) 2,2’-羟基乙基二硫化物在15 ml二氯甲烷中的溶液。
让反应在室温下继续16小时。
加入另外的6.1 g (0.01 mol) [氯(苯基)磷酰基]-(2,4,6-三甲基苯基)-甲酮,并将反应混合物回流24小时。
使反应混合物冷却至室温并在减压下去除溶剂。
在Prochrom LC80柱上,使用Kromasil Si60 10μm作为固定相,并且二氯甲烷/乙酸乙酯60/40作为洗脱剂,通过制备柱色谱法纯化INI-1。
分离出4.1 g的INI-3 (产率=29.5%) (在由Merck供应的TLC硅胶60F254上TLC分析,洗脱剂:正己烷/乙酸乙酯60/40,Rf:0.5)。
使用1H-NMR-光谱学(DMSO d6)分析INI-3 (参见表4)。
表4
INI-6的合成
根据以下反应方案制备光引发剂INI-6。
将3.1 g (15 mmol)硫辛酸溶解于50 ml乙酸乙酯中。分批加入3.3 g (16.5mmol)羰基二咪唑,并且让反应在室温下继续45分钟。加入0.2 g N-羟基琥珀酰亚胺,随后加入3.4 g (15 mmol) Darocur 2959。将反应混合物回流10小时。使反应混合物冷却至室温。加入另外的60 ml乙酸乙酯,并且用100 ml水萃取混合物。有机部分经MgSO4干燥并在减压下去除溶剂。使用制备柱色谱法在Varian Mega Bond柱上,使用从二氯甲烷到二氯甲烷/乙酸乙酯(90/10)的梯度洗脱分离INI-6。
分离出4.46 g的INI-6 (产率=72 %;在由Grace供应的Reveleris RP C18 TLC板上TLC分析,洗脱剂:MeOH/1M NaCl 85/15,Rf:0.43)。
使用1H-NMR-光谱学(CDCl3/TMS)分析INI-6 (参见表5)。
表5
Claims (12)
1.光引发剂,其选自酰基氧化膦、α-羟基-酮和α-氨基-酮,其特征在于所述光引发剂包括至少一个脂肪族二硫化物作为官能团。
2.根据权利要求1所述的光引发剂,其具有根据式I的化学结构,
其中
R1、R3和R5独立地选自氢、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和OR8;
R2和R4独立地选自氢、酰胺、磺酰胺、氨基甲酸酯、脲基、酯和醚;
R6选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和OR8;
R7选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、取代或未取代的芳基或杂芳基和酰基;
R8选自取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基和取代或未取代的芳基或杂芳基;
条件是R1至R8中的至少一个被脂肪族二硫化物取代。
5.根据权利要求4所述的光引发剂,其中R15表示取代或未取代的芳基。
6.根据权利要求4或5所述的光引发剂,其中L2表示包含不超过10个碳原子的二价连接基团。
8.根据权利要求7所述的光引发剂,其中R16选自取代或未取代的芳基和OR18。
9.根据权利要求7或8所述的光引发剂,其中R17选自取代或未取代的芳基和酰基。
10.根据权利要求7-9中任一项所述的光引发剂,其中L3包含选自酰胺、氨基甲酸酯和脲基的至少一个官能团。
11.可辐射固化的喷墨油墨,其包含如前述权利要求中任一项所定义的光引发剂。
12.制造印刷电路板(PCB)的方法,所述方法包括喷墨印刷步骤,其中将根据权利要求11所述的可辐射固化的喷墨油墨喷射并固化在基材上。
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