TWI769228B - 水溶性組成物、其硬化物之製造方法、及其硬化物,以及醯基膦酸鹽 - Google Patents
水溶性組成物、其硬化物之製造方法、及其硬化物,以及醯基膦酸鹽 Download PDFInfo
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- TWI769228B TWI769228B TW107108779A TW107108779A TWI769228B TW I769228 B TWI769228 B TW I769228B TW 107108779 A TW107108779 A TW 107108779A TW 107108779 A TW107108779 A TW 107108779A TW I769228 B TWI769228 B TW I769228B
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- QERXHBDEEFLTOL-UHFFFAOYSA-M sodium 1-[[4-[(4-sulfophenyl)diazenyl]phenyl]diazenyl]naphthalen-2-olate Chemical compound [Na+].Oc1ccc2ccccc2c1N=Nc1ccc(cc1)N=Nc1ccc(cc1)S([O-])(=O)=O QERXHBDEEFLTOL-UHFFFAOYSA-M 0.000 description 1
- VMGPESHNHVBCDP-UHFFFAOYSA-M sodium 3-[(8-acetamido-2-hydroxynaphthalen-1-yl)diazenyl]-5-chloro-2-hydroxybenzenesulfonate Chemical compound [Na+].CC(=O)Nc1cccc2ccc(O)c(N=Nc3cc(Cl)cc(c3O)S([O-])(=O)=O)c12 VMGPESHNHVBCDP-UHFFFAOYSA-M 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229940100996 sodium bisulfate Drugs 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940001474 sodium thiosulfate Drugs 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- JRQGFDPXVPTSJU-UHFFFAOYSA-L sodium zirconium(4+) sulfate Chemical compound [Na+].[Zr+4].[O-]S([O-])(=O)=O JRQGFDPXVPTSJU-UHFFFAOYSA-L 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- GNTPCYMJCJNRQB-UHFFFAOYSA-M sodium;2-[[4-(dimethylamino)phenyl]diazenyl]benzoate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1C([O-])=O GNTPCYMJCJNRQB-UHFFFAOYSA-M 0.000 description 1
- IDOPRZMNYMUGCN-UHFFFAOYSA-K sodium;2-hydroxypropane-1,2,3-tricarboxylate;zirconium(4+) Chemical compound [Na+].[Zr+4].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O IDOPRZMNYMUGCN-UHFFFAOYSA-K 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- PMLFOMWMYRKZRF-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]-6-hydroxybenzene-1,3-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=C(O)C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 PMLFOMWMYRKZRF-UHFFFAOYSA-M 0.000 description 1
- YZORUOZKRBVLEG-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 YZORUOZKRBVLEG-UHFFFAOYSA-M 0.000 description 1
- VVLFAAMTGMGYBS-UHFFFAOYSA-M sodium;4-[[4-(ethylamino)-3-methylphenyl]-(4-ethylimino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-3-sulfobenzenesulfonate Chemical compound [Na+].C1=C(C)C(NCC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S(O)(=O)=O)=C1C=C(C)C(=NCC)C=C1 VVLFAAMTGMGYBS-UHFFFAOYSA-M 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 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
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OLSOUGWNONTDCK-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)OC)=C(O)C2=C1N OLSOUGWNONTDCK-UHFFFAOYSA-J 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910000597 tin-copper alloy Inorganic materials 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical group C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- FKVXIGHJGBQFIH-UHFFFAOYSA-K trisodium 5-amino-3-[[4-[4-[(7-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N)S(=O)(=O)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)[O-])N)[O-].[Na+].[Na+].[Na+] FKVXIGHJGBQFIH-UHFFFAOYSA-K 0.000 description 1
- AZQHNNFDQFPAJZ-UHFFFAOYSA-H trisodium;5,6-diaminonaphthalene-1,3-disulfonate;iron(3+) Chemical compound [Na+].[Na+].[Na+].[Fe+3].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=C(N)C(N)=CC=C21.[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=C(N)C(N)=CC=C21.[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=C(N)C(N)=CC=C21 AZQHNNFDQFPAJZ-UHFFFAOYSA-H 0.000 description 1
- FUIZKNBTOOKONL-DPSBJRLESA-K trisodium;5-[(e)-(3-carboxy-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)-(2,6-dichloro-3-sulfonatophenyl)methyl]-3-methyl-2-oxidobenzoate Chemical compound [Na+].[Na+].[Na+].C1=C(C([O-])=O)C(=O)C(C)=C\C1=C(C=1C(=C(C=CC=1Cl)S([O-])(=O)=O)Cl)\C1=CC(C)=C(O)C(C([O-])=O)=C1 FUIZKNBTOOKONL-DPSBJRLESA-K 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- OEERILNPOAIBKF-UHFFFAOYSA-J zirconium(4+);tetraformate Chemical compound [Zr+4].[O-]C=O.[O-]C=O.[O-]C=O.[O-]C=O OEERILNPOAIBKF-UHFFFAOYSA-J 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
- C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/037—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
-
- 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)]
- C07F9/304—Aromatic acids (P-C aromatic linkage)
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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)]
- C07F9/307—Acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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Abstract
本發明係提供保存穩定性為優異、能夠適應於廣範圍光源並可形成高精細圖型之水溶性組成物、其硬化物之製造方法、及其硬化物、以及醯基膦酸鹽。 其含有:下述一般式(I)所表示之醯基膦酸鹽(A)、與具有下述一般式(II)所表示之基之化合物(B),(式中,X1
為表示碳原子數6~15之芳基,X2
為表示碳原子數1~8之直鏈烷基等,Am+
為表示鹼金屬離子等,m為表示1~3之數),(式中,R1
為表示氫原子等,Z1
為表示氧原子等,R2
為表示氫原子等,Z2
為表示碳原子數1~6之伸烷基,n為表示0~30之數,*意味著鍵結部,若具有多個複數的一般式(II)所表示之基之情形時,複數存在的R1
、X1
、X2
、n係可分別為相同或相異)。
Description
本發明係關於水溶性組成物、其硬化物之製造方法、及其硬化物、以及醯基膦酸鹽,詳細而言係關於保存穩定性為優異、能夠適應於廣範圍光源並可形成高精細圖型之水溶性組成物、其硬化物之製造方法、及其硬化物、以及醯基膦酸鹽。
水溶性組成物係被使用在塗料、油墨、接著劑、光學薄膜等的各種用途。若關注在水溶性組成物的水溶性起始劑時,專利文獻1中提案著一種水溶性油墨組成物,其含有:微粒子、具有乙烯性不飽和基的聚合性化合物、具有甜菜鹼構造的光聚合起始劑及水;專利文獻2中提案著一種經時穩定性、硬化感度及著液位置精度(landing position accuracy)為良好的油墨組成物,其含有作為水溶性起始劑之具有嗎啉(morpholine)構造的α-胺基苯乙酮以及作為水溶性化合物之具有丙烯醯胺構造的化合物;專利文獻3中提案著一種對於牙本質(特別是象牙質)的接著性為優異的牙科用接著性組成物,其含有丙烯酸酯系單體及作為光聚合起始劑之水溶性的醯基氧化膦(acylphosphine oxide)化合物。 [先前技術文獻] [專利文獻]
專利文獻1:國際公開2014/050551號 專利文獻2:日本特開2012-007070號公報 專利文獻3:日本特開2000-159621號公報
[發明所欲解決之課題]
水溶性組成物係要求著保存穩定性為優異、能夠適應於廣範圍光源並可形成高精細圖型之水溶性組成物。如此般的狀況時,關於專利文獻1~3中所提案般之水溶性組成物,未必能以市場所要求的高水準來兼具該等特性,故要求著水溶性組成物的進一步改良為現狀。
因此,本發明之目的係提供保存穩定性為優異、能夠適應於廣範圍光源並可形成高精細圖型之水溶性組成物、其硬化物的製造方法、及其硬化物、以及醯基膦酸鹽。 [解決課題之手段]
本發明人為解決上述課題經深入研究之結果發現,藉由使用含有具有特定構造的醯基膦酸鹽與環氧烷烴改質(甲基)丙烯酸酯化合物或(甲基)丙烯醯胺化合物而成之水溶性組成物,可解決上述課題,因而完成本發明。
即,本發明之水溶性組成物,其特徵係含有:下述一般式(I)所表示之醯基膦酸鹽(A)、與具有下述一般式(II)所表示之基之化合物(B),(式中,X1
為表示碳原子數6~15之芳基, X1
所表示之基中之氫原子係可被碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基、碳原子數3~8之具有支鏈之鹵化烷氧基所取代; X2
為表示碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、或碳原子數6~15之芳基, X2
所表示之碳原子數6~15之芳基中之氫原子係可被碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基、碳原子數3~8之具有支鏈之鹵化烷氧基、鹵原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯基醚基、巰基、異氰酸酯基或含有雜環之基所取代, X2
所表示之基中之亞甲基係可被氧原子或硫原子所取代, Am+
為表示鹼金屬離子、鹼土類金屬離子或 N+
HY1
Y2
Y3
, Y1
、Y2
及Y3
為分別獨立表示氫原子、羥基、碳原子數1~6之烷基、碳原子數1~6之烯基、碳原子數6~15之芳基或碳原子數7~13之芳烷基, Y1
、Y2
及Y3
所表示之基中之氫原子係可被羥基所取代, Y1
、Y2
及Y3
所表示之基中之亞甲基係可被氧原子、硫原子、羰基、或-N+
H-
所取代, Y1
與Y2
、Y1
與Y3
及Y2
與Y3
中任一者以上可鍵結並形成環, m為表示1~3之數),(式中,R1
為表示氫原子或甲基, Z1
為表示氧原子或-NR2
-, R2
為表示氫原子或碳原子數1~20之烴基, Z2
為表示碳原子數1~6之伸烷基, n為表示0~30之數, *意味著鍵結部, 若具有多個複數的一般式(II)所表示之基之情形時,複數存在的R1
、Z1
、Z2
、n係可分別為相同或相異)。
本發明之水溶性組成物,以前述一般式(I)中之X1
為2,4,6-三甲基苯基為較佳。又,本發明之水溶性組成物,以前述一般式(I)中之X2
為苯基、且Am+
為N+
HY1
Y2
Y3
為較佳。進而,本發明之水溶性組成物,以前述一般式(I)中之Am+
為N+
HY1
Y2
Y3
、且Y1
、Y2
及Y3
中任一者以上的氫原子係被羥基所取代為較佳。再進而,本發明之水溶性組成物,以前述一般式(II)中之Z1
為-NR2
-為較佳。再進而,本發明之水溶性組成物,以進而含有著色劑(C)為較佳。
又,本發明之硬化物之製造方法,其特徵係藉由光照射或加熱來使本發明之水溶性組成物硬化。
進而,本發明之硬化物,其特徵係由本發明之水溶性組成物所得到。
進而,本發明之醯基膦酸鹽,其係下述一般式(I)所表示之醯基膦酸鹽,(式中,X1
為表示碳原子數6~15之芳基, X1
所表示之基中之氫原子係可被碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基、碳原子數3~8之具有支鏈之鹵化烷氧基所取代, X2
為表示碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、或碳原子數6~15之芳基, X2
所表示之碳原子數6~15之芳基中之氫原子係可被碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基、碳原子數3~8之具有支鏈之鹵化烷氧基、鹵原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯基醚基、巰基、異氰酸酯基或含有雜環之基所取代, X2
所表示之基中之亞甲基係可被氧原子或硫原子所取代, Am+
為表示鹼金屬離子、鹼土類金屬離子或 N+
HY1
Y2
Y3
, Y1
、Y2
及Y3
為分別獨立表示氫原子、羥基、碳原子數1~6之烷基、碳原子數1~6之烯基、碳原子數6~15之芳基或碳原子數7~13之芳烷基, Y1
、Y2
及Y3
所表示之基中之氫原子係可被羥基所取代, Y1
、Y2
及Y3
所表示之基中之亞甲基係可被氧原子、硫原子、羰基、或-N+
H-
所取代, Y1
與Y2
、Y1
與Y3
及Y2
與Y3
中任一者以上可鍵結並形成環, m為表示1~3之數), 特徵為前述一般式(I)中之X2
為苯基、Am+
為 N+
HY1
Y2
Y3
,且Y1
與Y2
、Y1
與Y3
及Y2
與Y3
中任一者以上鍵結並形成環。
本發明之醯基膦酸鹽,以前述一般式(I)中之Am+
為N+
HY1
Y2
Y3
、且Y1
、Y2
及Y3
中任一者以上的氫原子係被羥基所取代為較佳。 [發明的效果]
依據本發明,可提供保存穩定性為優異、能夠適應於廣範圍光源並可形成高精細圖型之水溶性組成物、其硬化物之製造方法、及其硬化物、以及醯基膦酸鹽。本發明之水溶性組成物在對應高壓水銀燈、超高壓水銀燈、無電極燈及LED光源等的各種波長的光時,可製作高精細圖型。又,由於保存穩定性為優異,故可適合使用在塗料、油墨、接著劑、光學薄膜等的各種用途。又,本發明之醯基膦酸鹽係可適合使用在本發明之水溶性組成物中。
[實施發明之最佳形態]
以下,對於本發明之水溶性組成物來進行說明。本發明之水溶性組成物係含有下述一般式(I)所表示之醯基膦酸鹽(A)與具有下述一般式(II)所表示之基之化合物(B)。本發明之水溶性組成物由於保存穩定性為優異,故可以單液(one liquid)存在,且可對應各種的波長的光源,故可簡便地製作硬化物。以下,對於各成分依序來進行說明。
於此,一般式(I)中,X1
為表示碳原子數6~15之芳基,X1
所表示之基中之氫原子係可被碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基、碳原子數3~8之具有支鏈之鹵化烷氧基所取代。
又,一般式(I)中,X2
為表示碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、或碳原子數6~15之芳基。
X2
所表示之碳原子數6~15之芳基中之氫原子係可被碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基、碳原子數3~8之具有支鏈之鹵化烷氧基、鹵原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯基醚基、巰基、異氰酸酯基或含有雜環之基所取代,X2
所表示之基中之亞甲基係可被氧原子或硫原子所取代。
又,Am+
為表示鹼金屬離子、鹼土類金屬離子或N+
HY1
Y2
Y3
,Y1
、Y2
及Y3
為分別獨立表示碳原子數1~6之烷基、碳原子數1~6之烯基、碳原子數6~15之芳基或碳原子數7~13之芳烷基。又,Y1
、Y2
及Y3
所表示之基中之氫原子係可被羥基所取代,Y1
、Y2
及Y3
所表示之基中之亞甲基係可被氧原子、硫原子、羰基、或-N+
H-
所取代,Y1
與Y2
、Y1
與Y3
及Y2
與Y3
中任一者以上可鍵結並形成環。又,m為表示1~3之數。
作為一般式(I)中之X1
、X2
及Y1
~Y3
所表示之碳原子數6~15之芳基,可舉例如苯基、三甲基苯基、甲苯基、二甲苯基、2,4,6-三甲基苯基、萘基及蒽基等。
作為取代一般式(I)中之X1
及X2
所表示之基中之氫原子的基,可舉出碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈鹵化烷基、碳原子數3~8之具有支鏈之鹵化烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、碳原子數1~8之直鏈鹵化烷氧基及碳原子數3~8之具有支鏈之鹵化烷氧基。作為鹵原子,可舉出氟原子、氯原子、溴原子、碘原子等。
作為上述碳原子數1~8之直鏈烷基,可舉例如甲基、乙基、丙基、丁基、戊基、己基、庚基及辛基等。
作為上述碳原子數3~8之具有支鏈之烷基,可舉例如異丙基、丁基、異丁基、s-丁基、t-丁基、異戊基、t-戊基、異辛基、2-乙基己基及t-辛基等。
作為上述碳原子數1~8之直鏈鹵化烷基,係表示上述碳原子數1~8之直鏈烷基的1個以上的氫原子被鹵原子所取代者。
作為上述碳原子數3~8之具有支鏈之鹵化烷基,係表示上述碳原子數3~8之直鏈烷基的1個以上的氫原子被鹵原子所取代者。
作為上述碳原子數1~8之直鏈烷氧基,可舉例如甲氧基、乙氧基、n-丙氧基、n-丁氧基、t-丁氧基、n-戊氧基、n-己氧基及n-辛氧基等。
作為上述碳原子數3~8之具有支鏈之烷氧基,可舉例如異丙氧基、異丁氧基、環丁氧基、t-丁氧基、異戊氧基、新戊氧基及異辛氧基等。
作為上述碳原子數1~8之直鏈鹵化烷氧基,係表示上述碳原子數1~8之直鏈烷氧基的1個以上的氫原子被鹵原子所取代者。
作為上述碳原子數3~8之具有支鏈之鹵化烷氧基,係表示上述碳原子數3~8之直鏈烷氧基的1個以上的氫原子被鹵原子所取代者。
一般式(I)中之X2
所表示之碳原子數1~8之直鏈烷基、碳原子數3~8之具有支鏈之烷基、碳原子數1~8之直鏈烷氧基、碳原子數3~8之具有支鏈之烷氧基、及碳原子數6~15之芳基,係與取代上述一般式(I)中之X1
及X2
所表示之基中之氫原子所示例之基為相同者。
作為一般式(I)中之Y1
~Y3
所表示之碳原子數1~6之烷基,可舉出甲基、乙基、丙基、異丙基、丁基、異丁基、s-丁基、t-丁基、戊基、異戊基、t-戊基及己基等。
作為一般式(I)中之Y1
~Y3
所表示之碳原子數1~6之烯基,可舉例如乙烯基、乙烯、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基及5-己烯基等。
作為一般式(I)中之Y1
~Y3
所表示之碳原子數7~13之芳烷基,係意味著烷基的氫原子被芳基所取代的具有7~13之碳原子之基。可舉例如苄基、α-甲基苄基、α,α-二甲基苄基、苯基乙基及萘基丙基等。
本發明之水溶性組成物,若一般式(I)中之X1
為苯基、甲苯基、二甲苯基、2,4,6-三甲基苯基及萘基的化合物時,因為穩定性、吸收波長及對水之溶解性為優異,故為較佳。其中,若上述一般式(I)中之X1
為2,4,6-三甲基苯基的醯基膦酸鹽時,因為水溶性組成物的感度高,故為更佳。
本發明之水溶性組成物,若上述一般式(I)中之X2
為苯基、甲苯基、二甲苯基、2,4,6-三甲基苯基及萘基的化合物時,因為穩定性、吸收波長及對水之溶解性為優異,故為較佳。其中,若上述一般式(I)中之X2
為苯基時,因為感度高,故為更佳。
本發明之水溶性組成物,若上述一般式(I)中之X2
為苯基、且Am+
為N+
HY1
Y2
Y3
的醯基膦酸鹽時,因為對水之溶解性高、且水溶性組成物的感度為高,故為較佳。作為N+
HY1
Y2
Y3
之較佳者,可舉出下述化合物No.A1~ A41。但,本發明之水溶性組成物不因此受到以下的化合物任何限制。
上述一般式(I)中,若X2
為苯基、Am+
為 N+
HY1
Y2
Y3
、且Y1
與Y2
、Y1
與Y3
及Y2
與Y3
中任一者以上鍵結並形成環的醯基膦酸鹽時,因為對水之溶解性高且水溶性組成物的感度為高,故為特佳。
作為Y1
與Y2
、Y1
與Y3
及Y2
與Y3
中任一者以上鍵結並形成環的N+
HY1
Y2
Y3
之較佳者,可舉出上述化合物No.A1~A15。
上述N+
HY1
Y2
Y3
中,Y1
~Y3
的氫原子係被1個以上的羥基所取代的醯基膦酸鹽(A)時,因為與水之相溶性高,故為較佳。
醯基膦酸鹽(A)的含有量,相對於醯基膦酸鹽(A)及化合物(B)的總和100質量份為0.05~50質量份,較佳為0.1~35質量份。若醯基膦酸鹽(A)的含有量在該範圍內之情形時,在高壓水銀燈、超高壓水銀燈、無電極燈及LED光源之類的廣範圍光源下,可得到硬化性為良好之水溶性組成物,因為藉由該水溶性組成物從而可得到具有高精細圖型的硬化物,故為較佳。
於此,一般式(II)中,R1
為表示氫原子或甲基,Z1
為表示氧原子或-NR2
-,R2
為表示氫原子或碳原子數1~20之烴基,Z2
為表示碳原子數1~6之伸烷基,n為表示0~30之數,*意味著鍵結部。若具有多個複數的一般式(II)所表示之基之情形時,複數存在的R1
、X1
、X2
、n係可分別為相同或相異。
一般式(II)中之R2
所表示之碳原子數1~20之烴基並無特別限定,較佳為碳原子數1~20之烷基、碳原子數2~20之烯基、碳原子數3~20之環烷基、碳原子數4~20之環烷基烷基、碳原子數6~20之芳基及碳原子數7~20之芳烷基等。因為水溶性組成物的感度為良好,故以碳原子數1~10之烷基、碳原子數2~10之烯基、碳原子數3~10之環烷基、碳原子數4~10之環烷基烷基、碳原子數6~10之芳基及碳原子數7~10之芳烷基等為又較佳。
作為碳原子數1~20之烷基,可舉例如甲基、乙基、丙基、異丙基、丁基、異丁基、s-丁基、t-丁基、戊基、異戊基、t-戊基、己基、庚基、辛基、異辛基、2-乙基己基、t-辛基、壬基、異壬基、癸基、異癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基及二十烷基等,作為上述碳原子數1~10之烷基,可舉例如甲基、乙基、丙基、異丙基、丁基、異丁基、s-丁基、t-丁基、戊基、異戊基、t-戊基、己基、庚基、辛基、異辛基、2-乙基己基、t-辛基、壬基、異壬基、癸基及異癸基等。
作為碳原子數2~20之烯基,可舉例如乙烯基、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基、5-己烯基、2-庚烯基、3-庚烯基、4-庚烯基、3-辛烯基、3-壬烯基、4-癸烯基、3-十一烯基、4-十二烯基、3-環己烯基、2,5-環己二烯基-1-甲基、及4,8,12-十四烷三烯基烯丙基等,作為上述碳原子數2~10之烯基,可舉例如乙烯基、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基、5-己烯基、2-庚烯基、3-庚烯基、4-庚烯基、3-辛烯基、3-壬烯基及4-癸烯基等。
所謂的碳原子數3~20之環烷基,係意味著具有3~20之碳原子之飽和單環式或飽和多環式烷基。可舉例如環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、金剛烷基、十氫萘基、八氫并環戊二烯、雙環[1.1.1]戊二烯及十四烷氫蒽基等,作為上述碳原子數3~10之環烷基,可舉例如環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、金剛烷基、十氫萘基、八氫并環戊二烯及雙環[1.1.1]戊二烯等。
所謂的碳原子數4~20之環烷基烷基,係意味著烷基的氫原子被環烷基所取代的具有4~20之碳原子之基。可舉例如環丙基甲基、環丁基甲基、環戊基甲基、環己基甲基、環庚基甲基、環辛基甲基、環壬基甲基、環癸基甲基、2-環丁基乙基、2-環戊基乙基、2-環己基乙基、2-環庚基乙基、2-環辛基乙基、2-環壬基乙基、2-環癸基乙基、3-環丁基丙基、3-環戊基丙基、3-環己基丙基、3-環庚基丙基、3-環辛基丙基、3-環壬基丙基、3-環癸基丙基、4-環丁基丁基、4-環戊基丁基、4-環己基丁基、4-環庚基丁基、4-環辛基丁基、4-環壬基丁基、4-環癸基丁基、3-3-金剛烷基丙基及十氫萘基丙基等,作為碳原子數4~10之環烷基烷基,可舉例如環丙基甲基、環丁基甲基、環戊基甲基、環己基甲基、環庚基甲基、環辛基甲基、環壬基甲基、2-環丁基乙基、2-環戊基乙基、2-環己基乙基、2-環庚基乙基、2-環辛基乙基、3-環丁基丙基、3-環戊基丙基、3-環己基丙基、3-環庚基丙基、4-環丁基丁基、4-環戊基丁基及4-環己基丁基等。
作為碳原子數6~20之芳基,例如苯基、甲苯基、二甲苯基、乙基苯基、萘基、蒽基、菲基等、或以上述烷基、上述烯基或羧基、鹵原子等1個以上所取代的苯基、聯苯基、萘基、蒽基等,可舉例如4-氯苯基、4-羧基苯基、4-乙烯基苯基、4-甲基苯基、2,4,6-三甲基苯基等,作為上述碳原子數6~10之芳基,例如苯基、甲苯基、二甲苯基、乙基苯基及萘基等、或以上述烷基、上述烯基或羧基、鹵原子等1個以上所取代的苯基、聯苯基、萘基、蒽基等,可舉例如4-氯苯基、4-羧基苯基、4-乙烯基苯基、4-甲基苯基、2,4,6-三甲基苯基等。
所謂的碳原子數7~20之芳烷基,係意味著烷基的氫原子被芳基所取代的具有7~30之碳原子之基。可舉例如苄基、α-甲基苄基、α,α-二甲基苄基、苯基乙基及萘基丙基等,上述所謂的碳原子數7~20之芳烷基,係意味著烷基的氫原子被芳基所取代的具有7~20之碳原子之基。可舉例如苄基、α-甲基苄基、α,α-二甲基苄基及苯基乙基等。
作為一般式(II)中之Z2
所表示之碳原子數1~6之伸烷基,可舉例如亞甲基、伸乙基、伸丙基、伸丁基、伸戊基、伸己基等的直鏈狀伸烷基以及異伸丙基及異伸丁基等的支鏈狀伸烷基等。
作為化合物(B),較佳可使用例如環氧烷烴改質(甲基)丙烯酸酯化合物及(甲基)丙烯醯胺化合物。
上述所謂的環氧烷烴改質(甲基)丙烯酸酯化合物,係意味著環氧烷烴改質丙烯酸酯化合物或環氧烷烴改質甲基丙烯酸酯化合物。
上述所謂的(甲基)丙烯醯胺化合物,係意味著丙烯醯胺化合物或甲基丙烯醯胺化合物。
上述所謂的環氧烷烴改質丙烯酸酯化合物,係一般式(II)中之R1
為氫原子、Z1
為氧原子、n為1~30之化合物,上述所謂的環氧烷烴改質甲基丙烯酸酯化合物,係一般式(II)中之R1
為甲基、Z1
為氧原子、n為1~30之化合物。
作為上述環氧烷烴改質丙烯酸酯化合物,可舉例如二環氧乙烷改質新戊二醇二丙烯酸酯、二環氧丙烷改質新戊二醇二丙烯酸酯、二環氧乙烷改質1,6-己二醇二丙烯酸酯、二環氧丙烷改質1,6-己二醇二丙烯酸酯等,作為上述環氧烷烴改質甲基丙烯酸酯化合物,可舉例如二環氧乙烷改質新戊二醇二甲基丙烯酸酯、二環氧丙烷改質新戊二醇二甲基丙烯酸酯、二環氧乙烷改質1,6-己二醇二甲基丙烯酸酯、二環氧丙烷改質1,6-己二醇二甲基丙烯酸酯等。
作為上述環氧烷烴改質丙烯酸酯化合物及上述環氧烷烴改質甲基丙烯酸酯化合物,亦可較佳使用市售品,可舉例如NK EsterA-600、A-GLY-20E、NK Ekonoma A-PG5054E(以上新中村化學工業製)等。
上述環氧烷烴改質丙烯酸酯化合物及上述環氧烷烴改質甲基丙烯酸酯化合物中,若上述一般式(II)中之X2
為伸乙基、或伸丙基時,因為水溶性為優異故為較佳,由於伸乙基時特別是水溶性為優異故為較佳。
若上述環氧烷烴改質丙烯酸酯化合物及上述環氧烷烴改質甲基丙烯酸酯化合物具有1個一般式(II)所表示之基時,因為水溶性為優異,故以n為6以上之情形為特佳。若上述環氧烷烴改質丙烯酸酯化合物及環氧烷烴改質甲基丙烯酸酯化合物具有複數個一般式(II)所表示之基時,因為水溶性為優異,故以複數存在的n的總和為10以上之情形為特佳。
上述所謂的丙烯醯胺化合物,係上述一般式(II)中之R1
為氫原子、Z1
為-NR2
-、n為0之化合物,上述所謂的甲基丙烯醯胺化合物,係上述一般式(II)中之R1
為甲基、Z1
為-NR2
-、n為0之化合物。
作為上述丙烯醯胺化合物,可舉出羥基丙烯醯胺、N-甲基丙烯醯胺、N-乙基丙烯醯胺、N-異丙基丙烯醯胺、N-丁基丙烯醯胺、二丙酮丙烯醯胺、N,N-二甲基丙烯醯胺、N,N-二乙基丙烯醯胺、N,N-二丙基丙烯醯胺、丙烯醯基嗎啉、N-n-丁氧基甲基丙烯醯胺、N-異丁氧基甲基丙烯醯胺、N-甲氧基甲基丙烯醯胺等,作為上述甲基丙烯醯胺化合物,可舉出羥基甲基丙烯醯胺、N-甲基甲基丙烯醯胺、N-乙基甲基丙烯醯胺、N-異丙基甲基丙烯醯胺、N-丁基甲基丙烯醯胺、二丙酮甲基丙烯醯胺、N,N-二甲基甲基丙烯醯胺、N,N-二乙基甲基丙烯醯胺、N,N-二丙基甲基丙烯醯胺、甲基丙烯醯基嗎啉、N-n-丁氧基甲基甲基丙烯醯胺、N-異丁氧基甲基甲基丙烯醯胺、N-甲氧基甲基甲基丙烯醯胺等。
作為上述丙烯醯胺化合物及上述甲基丙烯醯胺化合物,亦可較佳使用市售品,可舉例如FFM-2、FFM-3、FFM-4及FFM-5、(Fujifilm公司製)。
化合物(B)的含有量,相對於醯基膦酸鹽(A)及化合物(B)的總和100質量份為70~99.5質量份,較佳為90~99.5質量份,若化合物(B)的含有量在該範圍內之情形時,在廣範圍光源(LED)下可得到硬化性為良好之水溶性組成物,因為藉由該水溶性組成物從而可得到具有高精細圖型的硬化物,故為較佳。
<溶劑> 本發明之水溶性組成物可含有水來作為溶劑,亦能夠與有機溶劑併用,但作為溶劑若僅只水的單液時,因為環境負荷低以及塗佈至有機材料上之情形時不會侵入有機材料中,故為較佳。
作為上述有機溶劑,藉由與水併用而能夠溶解或分散上述各成分(醯基膦酸鹽(A)及化合物(B))等之溶劑,可舉例如甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮及2-庚酮等的酮類;乙基醚、二噁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷及二丙二醇二甲基醚等的醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸-n-丙酯、乙酸異丙酯、乙酸n-丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯及2,2,4-三甲基-1,3-戊二醇單異丁酸酯(texanol)等的酯系溶劑;乙二醇單甲基醚及乙二醇單乙基醚等的溶纖劑系溶劑;甲醇、乙醇、異-或n-丙醇、異-或n-丁醇及戊醇等的醇系溶劑;乙二醇單甲基乙酸酯、乙二醇單乙基乙酸酯、丙二醇-1-單甲基醚(PGM)、丙二醇-1-單甲基醚-2-乙酸酯(PGMEA)、二丙二醇單甲基醚乙酸酯、3-甲氧基丁基乙酸酯及乙氧基乙基丙酸酯等的醚酯系溶劑;苯、甲苯及二甲苯等的芳香族系溶劑;己烷、庚烷、辛烷及環己烷等的脂肪族烴系溶劑;松節油、D-檸檬烯及蒎烯等的萜烯系烴油;礦油精、Swasol #310(以上為Cosmo松山石油製)、及Solvesso #100(以上為Exon化學製)等的石蠟系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷及1,2-二氯乙烷等的鹵化脂肪族烴系溶劑;氯苯等的鹵化芳香族烴系溶劑;卡必醇系溶劑、苯胺、三乙胺、砒啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸及水等,因為與水之相溶性良好,故以醇系溶劑為較佳。
本發明之水溶性組成物,若使用上述溶劑之情形時,其使用量並無特別限定,相對於水溶性組成物全量以成為70~95質量%為較佳。若溶劑的含有量為上述範圍之情形時,因為是操作性(硬化性組成物的黏度或潤濕性)及液穩定性(不會隨著組成物中所包含的成分而析出或沉澱)為優異的硬化性組成物以及可適當地控制硬化物的厚度,故為較佳。
<其他> 本發明之水溶性組成物,因應所需亦可加入:具有感光基及羥基之水溶性聚合物、聚乙烯醇改質水溶性聚合物、交聯劑、不具有感光基及下述一般式(VI)所表示之部分構造之水溶性聚合物、有機酸、偶合劑、增感劑、界面活性劑、鹼性化合物、著色劑、自由基起始劑(除了醯基膦酸鹽(A))、水溶性防腐劑及導電性物質等。
作為上述具有感光基及羥基之水溶性聚合物之較佳者,因為硬化物的耐熱性、耐水性及耐濕熱性為高,故可舉出具有下述一般式(IIIα)~(IIIε)來作為構成單位之化合物,其中,具有(IIIδ)及(IIIε)來作為構成單位之化合物,即使在使用LED光源(365nm)之情形時,因為可得到硬化性為優異之水溶性組成物以及耐熱性、耐水性及耐濕熱性為優異的硬化物,故為又較佳。
作為一般式(IIIα)、(IIIβ)及(IIIγ)中之Y4
、Y5
及Y6
所表示之2價的連結基並無特別限制,但較佳可舉例如亞甲基、伸乙基、三亞甲基、伸丙基、伸丁基等之碳原子數1~10之伸烷基、伸苯基、萘基等之碳原子數6~30的伸芳基、雜環連結基、-CH=CH-、-O-、-S-、-C(=O)-、 -CO-、-NR-、-CONR-、-OC-、-SO-、-SO2
-及組合2個以上該等之連結基。於此,R為分別獨立表示氫原子、烷基、芳基、或雜環基。
作為一般式(IIIα)、(IIIβ)及(IIIγ)中之Q1
、Q2
及Q3
所表示之感光基,可舉例如桂醯基、桂皮醯基、亞肉桂基、亞肉桂基乙醯基、查耳酮基、香豆素基、異香豆素基、2,5-二甲氧基二苯乙烯基、馬來醯亞胺基、α-苯基馬來醯亞胺基、2-吡喃酮基、疊氮基、胸腺嘧啶、醌基、尿嘧啶基、嘧啶基、苯乙烯基吡啶鎓基、苯乙烯基吡啶鎓基、苯乙烯基喹啉鎓基、環氧基、氧雜環丁烷基、乙烯基醚基、烯丙基醚基、丙烯醯基、甲基丙烯醯基、丙烯醯胺基、甲基丙烯醯胺基、乙烯基、烯丙基、苯乙烯基等,該等之中,因為可得到感光性高、液穩定性(不伴隨著增稠、凝膠化、析出等)高之水溶性組成物,故較佳可使用苯乙烯基吡啶鎓(stilbazolium)基、桂皮醯基、丙烯醯基、甲基丙烯醯基、丙烯醯胺基或甲基丙烯醯胺基。
上述感光基之中,苯乙烯基吡啶鎓基係由於對水之溶解性為高,又,在365nm附近具有吸收帶,故可得到即使在LED光源(365nm)等的波長較長的光源下亦能展現出感光性之水溶性組成物。由該水溶性組成物,除了可得到耐熱性、耐水性及耐濕熱性以外,亦可得到高精細圖型的硬化物,故可特佳來使用。
作為較佳的具有感光基及羥基之水溶性聚合物之具體例,可舉出下述一般式(IV)及下述一般式(V)所表示之水溶性感光聚合物。
於此,式(IV)中之Y4
及Q1
係與上述一般式(IIIα)為相同,Y6
及Q3
係與上述一般式(IIIγ)為相同,a、b、c、及d係0~5000為止之數,a及d不同時為0,且100<a+b+c+d<5000,*係鍵結部。
因為藉由本發明之水溶性組成物所得到的硬化物的耐熱性及密著性為良好,故一般式(IV)及(V)中,a、b、c及d(莫耳比)的較佳值為a:b:c:d=0.1~4:5~30:5~70:0.1~4,重量平均分子量為1.5萬~500萬,較佳以10萬~100萬為佳。
一般式(V)所表示之聚合物,係藉由在pH1~4的條件下使丁烯二醇-聚乙烯醇共聚物與具有感光基的醛進行縮醛化反應而可得到。又,藉由使用市售品亦可進行製造,例如藉由在pH1~4的條件下,使日本合成化學公司製的G-plolymer(丁烯二醇乙烯醇共聚物)OKS-1081、OKS-1083、OKS-1109,與具有感光基的醛進行縮醛化反應而亦可得到。
所謂的聚乙烯醇改質水溶性聚合物,係在構造中不具有上述感光基、且具有下述一般式(VI)所表示之構成單位之水溶性聚合物,藉由與後述的交聯劑一起添加從而可提升所得到的硬化物的耐熱性。
聚乙烯醇改質水溶性聚合物,作為主鏈係與以往周知的聚乙烯醇為相同地,一般而言可舉出稱為聚乙烯醇(poval)的使乙烯醇聚合而成的聚乙烯醇、部分皂化聚乙烯醇、完全皂化聚乙烯醇、或與下述單體的共聚物的皂化物等,所述的單體係與乙酸乙烯酯具有共聚合性的單體。尚,構成聚乙烯醇改質水溶性聚合物的聚乙烯醇,可以是將乙烯醇作為必須單體的均聚物,亦可以是共聚物。
作為聚乙烯醇改質水溶性聚合物之製造方法,並無特別限定,但可舉例如使聚乙烯醇與二乙烯酮反應之方法、使聚乙烯醇與乙醯乙酸酯反應並進行酯交換之方法、使乙酸乙烯酯與乙醯乙酸乙烯酯的共聚物進行皂化之方法等。該等之中,因為可得到製造步驟為簡略、且具有品質為佳的乙醯乙酸酯基的聚乙烯醇,故以採用使聚乙烯醇與二乙烯酮反應之方法來製造為較佳。
作為與乙酸乙烯酯具有共聚合性的單體,可舉例如馬來酸、馬來酸酐、福馬酸、巴豆酸、伊康酸、丙烯酸、甲基丙烯酸等的不飽和羧酸及其酯類、乙烯、丙烯等的α-烯烴、烯丙基磺酸、甲基烯丙基磺酸、烯丙基磺酸鈉、甲基烯丙基磺酸鈉、磺酸鈉、磺酸鈉單烷基馬來酸酯、二磺酸鈉烷基馬來酸酯、N-羥甲基丙烯醯胺、丙烯醯胺烷基磺酸鹼鹽、N-乙烯基吡咯啶酮、N-乙烯基吡咯啶酮衍生物等,該等單體係全構造單位的10莫耳%以下,特別以5莫耳%為較佳。若過多時將會有水溶性降低之虞。
藉由在本發明之水溶性組成物中,添加經凝膠滲透層析法(GPC)之聚苯乙烯換算重量平均分子量(Mw)為10,000~200,000、皂化度(水解率)為85~100的聚乙烯醇改質水溶性聚合物與後述的交聯劑,所得到的硬化物的耐水性會提升、且膜的耐久性會提升,因而較佳,皂化度為95~100的聚乙烯醇改質水溶性聚合物時,因為耐水性會更加提升,故為又較佳。
一般式(VII)所表示之構成單位的含有量,通常為0.1~20莫耳%,進而為0.2~15莫耳%,特別是0.3~10莫耳%,但就硬化物的耐水性、交聯速度、水溶性、水溶液的穩定性之觀點而言為較佳。
作為聚乙烯醇改質水溶性聚合物亦可使用市售品,可舉例如GOHSENX Z-100、Z-200、Z-220、Z-300及Z-410(日本合成化學工業公司製)等。
上述交聯劑,只要是能夠使聚乙烯醇改質水溶性聚合物進行交聯者即可,並無限制而可使用。作為交聯劑,較佳可使用例如以往已知的有機系交聯劑、具有螯合化劑的金屬螯合錯合物、鋯化合物及鈦化合物。
作為有機系交聯劑,可從被慣用作為交聯劑之中任意地來選擇使用,可舉例如雙二疊氮化合物、具有羥基或烷氧基的胺基樹脂、聚乙烯亞胺、三聚氰胺樹脂、脲樹脂、胍胺樹脂、乙炔脲-甲醛樹脂、琥珀醯胺-甲醛樹脂、乙烯脲-甲醛樹脂等。該等係可以使用使三聚氰胺、脲、胍胺、乙炔脲、琥珀醯胺、乙烯脲在沸騰水中與福馬林反應來進行羥甲基化而得到的產物、或者使它們進而與低階醇反應來進行烷氧基化而得到的產物。
作為螯合化劑,可舉出羥基羧酸或其鹽、乙醛酸或其鹽、胺基醇、胺基羧酸、丙胺酸、精胺酸、白胺酸、異白胺酸、二羥基丙基甘胺酸、乙二胺四乙酸、二乙烯三胺五乙酸、氮基三乙酸、β-二酮、二甲基乙二肟、檸檬酸、酒石酸、馬來酸、聚醯肼、磷酸酯等,該等係可以1種或可組合2種以上來使用。
若使用具有螯合化劑的金屬螯合錯合物之情形時,由於交聯反應速度可適度地被調節故為較佳,所述的螯合化劑,其係可對1個的金屬原子藉由共價鍵或氫鍵等來進行二牙或其以上的多牙配位者。作為螯合型配位子,具體而言可舉出羥基羧酸或其鹽、胺基醇、β-二酮等。
作為鋯化合物,除了二氯氧化鋯、羥基氯化鋯、四氯化鋯、溴化鋯等的鹵化鋯;硫酸鋯、鹼性硫酸鋯、硝酸氧鋯、乙酸氧鋯、碳酸氧鋯等的礦酸的鋯鹽;甲酸鋯、乙酸鋯、丙酸鋯、醯辛酸鋯、硬脂酸鋯、乳酸鋯、硝酸鋯、碳酸鋯、辛酸鋯、檸檬酸鋯、磷酸鋯等的有機酸的鋯鹽;碳酸鋯銨、硫酸鋯鈉、乙酸鋯銨、碳酸鋯銨、碳酸鋯鉀、草酸鋯鈉、檸檬酸鋯鈉、檸檬酸鋯銨、乳酸鋯銨等的鋯錯鹽酯之外,可舉出將一種或二種以上的螯合化劑作為配位子的鋯螯合錯合物。該等之中,以水溶性鋯為較佳,以鹵氧化鋯、乙酸氧鋯、硫酸鋯及硝酸氧鋯為又較佳。
作為鋯螯合錯合物,可舉例如四乙醯丙酮鋯、單乙醯丙酮鋯、鹵氧化鋯、硝酸氧鋯、乳酸鋯銨、硫酸鋯及乙酸氧鋯、雙乙醯丙酮鋯、單乙基乙酸鋯酯、乙酸鋯酯等。
鋯化合物之中,四乙醯丙酮鋯、單乙醯丙酮鋯、鹵氧化鋯、硝酸氧鋯、乳酸鋯銨、硫酸鋯及乙酸氧鋯等,因為穩定性、水溶性、反應性較高故為較佳。該等係可以一種或可二種以上的混合物來使用。
作為鋯化合物亦可使用市售品,可舉例如二氯氧化鋯、Zircosol ZC-2、Zircosol ZN、Zircosol HA、Zircosol AC-7、Zircosol ZK-10、Zircosol ZN、Zircosol ZA-10、Zircosol ZA-20、辛酸鋯、碳酸鋯(以上第一希元素化學工業公司製)Orgatix ZA-45、Orgatix ZA-65、Orgatix ZB-126、Orgatix ZC-126、Orgatix ZC-150、Orgatix ZC-200、Orgatix ZC-300、Orgatix ZC-320、Orgatix ZC-540、Orgatix ZC-580、Orgatix ZC-700、ZC-300(以上Matsumoto Fine Chemical公司製)等。
作為鈦化合物,可舉出鈦酸四甲酯、鈦酸四乙酯、鈦酸四正丙酯、鈦酸四異丙酯、鈦酸四正丁酯、鈦酸四異丁酯、鈦酸四-t-丁酯、鈦酸四辛酯、四(2-乙基己基)鈦酸酯、鈦酸四甲酯等的鈦氧化物;鈦丁基二聚物、鈦丁基四聚物等的之藉由鈦氧化物的水解分解反應所得到的寡聚物或聚合物及此等的衍生物;乙醯丙酮酸鈦、辛二醇鈦、四乙醯丙酮酸鈦、乙基乙醯乙酸鈦、三乙醇胺鋁酸鈦、草酸鈦等的鈦螯合錯合物;聚羥基硬酯酸鈦等的醯化鈦;四氯化鈦、乳酸鈦、三乙醇胺鈦、二異丙氧基鈦雙(三乙醇胺)等,該等係可以一種或可二種以上的混合物來使用。
作為鈦化合物亦可使用市售品,可舉例如Orgatix TA-8、Orgatix TA-10、Orgatix TA-12、Orgatix TC-100、Orgatix TC-120、Orgatix TC-300、Orgatix TC-310、Orgatix TC-315、Orgatix TC-335、Orgatix TC-401、Orgatix TC-800、Orgatix WS-700(以上Matsumoto Fine Chemical公司製)TITA BOND T-100、TITA BOND T-120、TITA BOND T-120A、TITA BOND T-150、TITA BOND T-160、TITA BOND T-180E、TITA BOND T-185E(以上日本曹達製)等。
因為藉由本發明之水溶性組成物所得到的硬化物之耐濕熱性為良好,故上述交聯劑之中以鋯化合物或鈦化合物為特佳。
若添加交聯劑與聚乙烯醇改質水溶性聚合物之情形時,相對於聚乙烯醇改質水溶性聚合物的100質量份,交聯劑的添加量為0.01~5質量份,但由於沒有析出或增稠等的變化,而使水溶性組成物呈穩定故為較佳。
雖本發明之水溶性組成物中包含源自交聯劑的金屬成分,但在去除水溶性組成物的溶劑的成分中,金屬含有量係以0.01~3質量%為較佳,又較佳為0.01~1質量%。
作為不具有上述感光基及上述一般式(VI)所表示之構成單位之水溶性聚合物,可舉出氧化澱粉、經醚化・酯化・接枝化的改質澱粉、明膠・酪蛋白・羧甲基纖維素等的纖維素衍生物、聚乙烯基吡咯啶酮、水溶性聚酯樹脂、丙烯酸-2-羥基丙酯聚合物・丙烯酸-4-羥基丁酯聚合物等的水溶性聚丙烯酸酯樹脂、水溶性聚碳酸酯樹脂、水溶性聚乙酸乙烯酯樹脂、水溶性苯乙烯丙烯酸酯樹脂、水溶性乙烯基甲苯丙烯酸酯樹脂、水溶性聚胺基甲酸酯樹脂、聚乙烯基醯胺・聚丙烯醯胺、改質丙烯醯胺等的水溶性聚醯胺樹脂、水溶性脲樹脂、水溶性聚己內酯樹脂、水溶性聚苯乙烯樹脂、水溶性聚氯乙烯樹脂、水溶性聚丙烯酸酯樹脂、水溶性聚丙烯腈樹脂等的水溶性樹脂及苯乙烯・丁二烯共聚物、丙烯酸酯共聚物、乙烯・乙酸乙烯酯共聚物等。
作為上述有機酸,只要是具有羧基的弱酸性的化合物即可無限制的使用,可舉例如乙酸、檸檬酸、蘋果酸、乙醇酸、乳酸、碳酸、甲酸、草酸、丙酸、辛酸、醯辛酸、葡糖醛酸、硬脂酸、苯甲酸、杏仁酸等。該等之中,以乳酸、乙酸、檸檬酸、乙醇酸或蘋果酸為較佳。
作為上述偶合劑,可使用二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三甲氧基矽烷等之烷基官能性烷氧基矽烷、乙烯基三氯矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、烯丙基三甲氧基矽烷等的烯基官能性烷氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、2-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷、γ-縮水甘油氧基丙基甲基二乙氧基矽烷、β-(3,4-環氧基環己基)乙基三甲氧基矽烷等之環氧基官能性烷氧基矽烷、N-β(胺基乙基)-γ-胺基丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、N-苯基-γ-胺基丙基三甲氧基矽烷等的胺基官能性烷氧基矽烷及γ-巰基丙基三甲氧基矽烷等的巰基官能性烷氧基矽烷等。
上述增感劑係藉由光照射從而硬化時,可擴大能適用的光的波長範圍的化合物,作為增感劑係以例如日本特開2005-307199中所記載的噻吨酮類、日本特開2012-7071中所記載的噻吨酮類、WO2014/050551中所記載的二苯甲酮類、噻吨酮類、硫色滿酮類、聯咪唑類等為較佳。
作為上述以外的增感劑,可舉例如α-胺基苯乙酮類、α-羥基苯乙酮類、苄基縮酮類二苯甲酮、3-羥基二苯甲酮、4-羥基二苯甲酮、4,4-二羥基二苯甲酮、2-甲基二苯甲酮、3-甲基二苯甲酮、4-甲基二苯甲酮、2,5-二甲基二苯甲酮、3,4-二甲基二苯甲酮、4-甲氧基二苯甲酮、4,4-二甲氧基二苯甲酮、3,3-二甲基-4-甲氧基二苯甲酮、4-苯基二苯甲酮等的二苯甲酮類、苯乙酮、4-甲氧基苯乙酮、2,4-二甲氧基苯乙酮、2,5-二甲氧基苯乙酮、2,6-二甲氧基苯乙酮、4,4-二甲氧基苯乙酮、4-乙氧基苯乙酮、二乙氧基苯乙酮、2,2-二乙氧基苯乙酮、2-乙氧基-2-苯基苯乙酮、4-苯基苯乙酮等的苯乙酮類、蒽醌、羥基蒽醌、1-硝基蒽醌、胺基蒽醌、2-氯蒽醌、2-甲基蒽醌、2-乙基蒽醌、蒽醌磺酸、1,2-苯并蒽醌、1,4-羥基蒽醌(醌茜)等的蒽醌類、蒽、1,2-苯并蒽、9-氰基蒽、9,10-二氰基蒽、2-乙基-9,10-二甲氧基蒽、9,10-雙(苯基乙基)蒽等的蒽類、2,3-二氯-6-二氰基-p-苯醌、2,3-二甲氧基-5-甲基-1,4-苯醌、甲氧基苯醌、2,5-二氯-p-苯醌、2,6-二甲基-1,4-苯醌、9,10-菲醌、樟腦醌、2,3-二氯-1,4-萘醌、呫噸酮等的醌類、噻吨酮、2-甲基噻吨酮、2,4-二甲基噻吨酮、異丙基噻吨酮、2,4-二乙基噻吨酮、2,4-異丙基噻吨酮等的噻噁烷類、二苯并環庚酮、二苯并環庚烯、二苯并環庚醇、二苯并環庚烷等之環庚烷類、2-甲氧基萘、苯偶姻異丙基醚、4-苯甲醯二苯基、o-苯甲醯苯甲酸、o-苯甲醯苯甲酸甲酯、4-苯甲醯-4-甲基-二苯基硫醚、苄基、苯偶姻甲基醚等的芳香族化合物、及色素系增感性物質的香豆素系、噻系、氮苯系、吖啶系、二苯并哌喃系化合物等,其中,特別是就在水中的穩定性較高(難以受到水解)之類的觀點而言,以二苯甲酮類、噻吨酮類、硫色滿酮類、聯咪唑類、α-胺基苯乙酮類、α-羥基苯乙酮類、苄基縮酮類為較佳。
作為上述界面活性劑,可使用全氟烷基磷酸酯、全氟烷基羧酸鹽等的氟界面活性劑、高階脂肪酸鹼鹽、烷基磺酸鹽、烷基硫酸鹽等的陰離子系界面活性劑、高階胺鹵酸鹽、第四級銨鹽等的陽離子系界面活性劑、聚乙二醇烷基醚、聚乙二醇脂肪酸酯、去水山梨醇脂肪酸酯、脂肪酸甘油單酸酯等的非離子界面活性劑、兩性界面活性劑、聚矽氧系界面活性劑等的界面活性劑,該等係可組合來使用。
作為上述鹼性化合物,可舉例如氨、氫氧化鈉、氫氧化鉀、三乙胺、三乙醇胺、二乙醇胺、單乙醇胺、三異丙醇胺、二異丙醇胺、單異丙醇胺、N,N-二甲基乙醇胺、伸乙亞胺、吡咯啶、哌啶、聚乙烯亞胺等,該等係可一種或可組合二種以上來使用,有時會依照pH調整等的目的來添加鹼性化合物。
作為上述著色劑可使用顏料及染料。作為顏料及染料係可分別使用無機色料或有機色料,該等可以單獨或混合2種以上來使用。於此,所謂的顏料係指不溶於後述的溶劑中之著色劑,且亦包含即使是在無機或有機色料之中也不會溶於溶劑者、或者是使無機或有機染料被色澱化者。
作為上述顏料,可舉出藉由爐法、槽法或熱裂法所得到的碳黑、或者乙炔黑、科琴黑(Ketjen black)或燈黑等的碳黑,利用環氧樹脂來調整或被覆上述碳黑者、預先在溶劑中利用樹脂分散處理上述碳黑,並利用20~200mg/g的樹脂被覆者、將上述碳黑進行酸性或鹼性表面處理者、平均粒徑為8nm以上且DBP吸油量為90ml/100g以下的碳黑、由950℃下揮發分中之CO及CO2
所算出的全氧量為每表面積100m2
為9mg以上的碳黑、石墨化碳黑、石墨、活性碳、碳纖維、奈米碳管、微螺旋碳管、碳奈米角、碳氣凝膠、富勒烯、苯胺黑、顏料黑7、鈦黑等所代表的黑色顏料、氧化鉻綠、米洛麗藍、鈷綠、鈷藍、錳系、亞鐵氰化物、磷酸鹽群青、鐵藍、群青、天藍、鉻綠色、翡翠綠、硫酸鉛、黃色鉛、鋅黃、紅鐵(紅色氧化鐵(III))、鎘紅、合成鐵黑、棕土、色澱顏料等的有機或無機顏料,因為遮光性較高故以使用黑色顏料為較佳,作為黑色顏料以使用碳黑為更佳。
作為上述顏料亦可使用市售品,可舉例如MICROPI GMO WMYW-5、MICROPIGMO WMRD-5、MICROPIGMO WMBN-5、MICROPIGMO WMGN-5、MICROPIGMO WMBK-5、MICROPIGMO WMBE-5、MICROPIGMO WMVT-5、MICROPIGMO WMWE-1、BONJET BLACK CW-1(以上為ORIENT化學工業公司製)顏料紅1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、254、228、240及254;顏料橘13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65及71;顏料黃1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180及185;顏料綠7、10、36及58;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62及64;顏料紫1、19、23、27、29、30、32、37、40及50等。
作為上述染料,可舉例如亞硝基化合物、硝基化合物、偶氮化合物、重氮化合物、呫噸化合物、喹啉化合物、蒽醌化合物、香豆素化合物、花青素化合物、酞青素化合物、異吲哚啉酮化合物、異吲哚啉化合物、喹吖酮化合物、蒽垛蒽酮化合物、紫環酮化合物、苝化合物、二酮基吡咯并吡咯化合物、硫靛藍化合物、二噁嗪化合物、三苯基甲烷化合物、喹啉黃化合物、萘四羧酸、偶氮染料、花青素染料的金屬錯合物化合物等。
作為上述染料可適時使用水溶性染料及油溶性染料。
作為上述染料亦可使用市售品,可舉例如WATER YELLOW 1、WATER YELLOW 2、WATER YELLOW 6C、WATER YELLOW 6CL、WATER ORANGE 18、WATER ORANGE 25、WATER RED 1、WATER RED 2S、WATER RED 3、WATER RED 9、WATER RED 27、WATER PINK 2S、WATER BROWN 16、WATER GREEN 8、WATER BLUE3、WATER BLUE 9、WATER BLUE 105S、WATER BLUE 106、WATER BLUE 117-L、WATERVIOLET 7、WATER BLACK 31、WATER BLACK 191-L、WATER BLACK 256-L、WATER BLACK R-455、WATER BLACK R-510、BONJET YELLOW 161-L、BONJET MAGENTA XXX、BONJET CYAN XXX、BONJET BLACK 891-L、VALIFAST YELLOW 1101、VALIFAST YELLOW 3150、VALIFAST RED 1308、VALIFAST RED 2320、VALIFAST PINK 1364、VALIFAST PINK 2310N、ALIFAST VIOLET 1701、VALIFAST BLACK 1815、VALIFAST BLACK 1807、VALIFAST BLACK 3804、VALIFAST BLACK 3810、VALIFAST BLACK 3820、VALIFAST BLACK 3830、VALIFAST BLACK 3840、VALIFAST BLACK 3866、VALIFAST BLACK 3870、VALIFAST ORANGE 2210、VALIFAST BROWN 3402、VALIFAST BLUE1613及VALIFAST BLUE 1605(以上為ORIENT化學工業公司製)Acid Green 1、Acid Green 3、Acid Green 5、Acid Green 9、Acid Green 27、Acid Green 50、Acid Green A、Alizarin Cyanin Green F、Basic Green1、Basic Green 5、Bromocresol Green、Bromocresol Green Sodium Salt、ErioGreen B、Fast Green FCF、Fiter Blue Green Sodium Salt、Indocyanine Green、Janus Green B、Leuco Malachite Green、Malachite Green,Oxalate、Methyl Green、Palatine Chrome Green、Quinizarin Green SS、Acid Red 1、Acid Red 9、Acid Red 13、Acid Red 18、Acid Red 26、Acid Red 27、Acid Red 52、Acid Red 87、Acid Red 88、Acid Red 91、Acid Red 92、Acid Red 94、Acid Red 112、Acid Red 114、Acid Red 151、Acid Red 289、Alizarin、Allura Red AC、Astrazon Red 6B、Azo Rubine、Basic Red 5、Benzopurpurine 4B、Bordezux Red、Chlorantine Fast Red 5B、Chromotrope 2B、Chromotrope 2R、Congo Red、Cresol Red、Crezol Red Sodium Salt、Crocein Scarlet 3B、Direct Fast Red 3B、Direct Red 80、Direct Scarlet B、Eriochrome Red B、4-Ethoxychrysoidine Hydrochloride、Ethyl Red、Fast Red B Salt、Fast Red ITR Base、Lake Red CBA、Lithol Rubin BCA、Methoxy Red、Methyl Red、Methyl Red Sodium Salt、Oralith Brilliant Pink R、Para Red、Phenol Red Sodium Salt、Pigment Red、Pigment Red 254、Rhodamine 6G、Sudan II、Sudan III、Sudan R、2,3,5-Triphenyltetrazolium Chloride、Acid Black 1、Acid Blue 1、Acid Blue 9、Acid Blue 92、Acid Blue 3 Sodium Salt、Acid Red 91、Azo Blue、Basic Blue 1、Basic Blue 7、Basic Blue 12、Basic Blue 17、Basic Blue 24、Basic Blue 26、Briliant Blue G、Brilliant Blue R、Bromocresol Blue、Bromophenol Blue、Bromothymol Blue、Chrome Pure Blue BX、Coomassie Brilliant Blue G-250、Coomassie Brilliant Blue R-250、Direct Blue 1、Direct Blue 2、Direct Blue 14、Direct Sky Blue、Disperse Blue 14、Eriochrome Blue Black B、Eriochrome Cyanine R、Evans Blue、Filter Blue Green Sodium Salt、Indigo Carmine、Indigo、Methylene Blue Hydrate、Mordant Black 17、Mordant Blue 13、Mordant Blue 29、Omega Chrome Black Blue G、Pigment Blue 15、Quinizarin Blue、Sudan Blue、Thymol Blue、Xylene Cyanol FF、Acid Orange 5、Acid Orange 7、1-Amino-2-methylanthraquione、Astrazon Orange R、Basic Orange 14、Crocein Orange G、Ethyl Orange、Methyl Orange、Mordant Orange 1、α-Naphtol Orange、Oil Orange、Orange G、Permanent Orange、Pyrazolone Orange、Sudan I、Sudan II(以上為東京化成工業公司製)等。
作為上述自由基起始劑(除了醯基膦酸鹽(A))能夠使用以往已知的化合物,例如日本特開平6-228218、日本特開2009-102455、日本特開2012-007071、 WO2014/050551、日本特開平06-239910、日本特開 2003-192712、日本特開2016-185929中所記載者之外,可使用二苯甲酮、噻吨酮、1-氯基-4-丙氧基噻吨酮、異丙基噻吨酮、二乙基噻吨酮、乙基蒽醌等的脫氫型(hydrogen-drawing type)的光聚合起始劑;苯基聯苯基酮、1-羥基-1-苯甲醯環己烷(α-羥基烷基苯酮)、苯偶姻、苄基二甲基縮酮、1-苄基-1-二甲基胺基-1-(4’-嗎啉基苯甲醯基)丙烷、2-嗎啉基-2-(4’-甲基巰基)苯甲醯丙烷、4-苯甲醯-4’-甲基二苯基硫醚、苯偶姻丁基醚、2-羥基-2-苯甲醯丙烷、2-羥基-2-(4’-異丙基)苯甲醯丙烷、4-丁基苯甲醯三氯甲烷、4-苯氧基苯甲醯二氯甲烷、苯甲醯甲酸甲酯、1-羥基-環己基-苯基-酮、2-羥基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮、1,7-雙(9’-吖啶基)庚烷、9-n-丁基-3,6-雙(2’-嗎啉基異丁醯基)咔唑、2-甲基-4,6-雙(三氯甲基)-s-三嗪、2-苯基-4,6-雙(三氯甲基)-s-三嗪、2-萘基-4,6-雙(三氯甲基)-s-三嗪、2,2-雙(2-氯苯基)-4,5,4’,5’-四苯基-1-2’-聯咪唑等的光分解型光聚合起始劑,就反應性之點而言,以光分解型光聚合起始劑為較佳。
上述光分解型光聚合起始劑之中,以 Irg2959、Irg819DW(BASF公司製)、ESACURE ONE、ESACURE 1001M、ESACURE KIP 150及ESACURE DP 250(Lamberti公司)等的水溶性起始劑等,因為對水的親和性較高故為較佳。
作為上述水溶性防腐劑,可舉出對水的溶解度較高、且在室溫下的溶解度為1%以上者,具體而言可舉出對羥基苯甲酸甲酯、苯甲酸、苯甲酸鹽、水楊酸、水楊酸鹽、苯氧基乙醇、水溶性陽離子抗菌劑、有機硫化合物、鹵化化合物、環狀有機氮化合物、低分子量醛、對羥基苯甲酸、丙二醇物質、異噻唑啉酮、四級化合物、苯甲酸酯、低分子量醇、脫氫乙酸、ACQ(銅-第四級銨化合物)、CUAZ(銅-唑化合物)、AAQ(第4級銨化合物)、亞硫酸氫鈉、硫酸氫鈉、硫代硫酸鈉、抗壞血酸鹽、苯扎氯銨、氯丁醇、硫柳汞、乙酸苯基水銀、硼酸苯基水銀、硝酸苯基水銀、對羥基苯甲酸、對羥基苯甲酸甲酯、聚乙烯醇、苄醇、異噻唑啉酮、三嗪、溴硝丙二醇、噻苯咪唑、吡硫鎓鋅、多菌靈、吡啶氧化物硫醇鈉鹽及苯基乙醇等。
作為上述水溶性防腐劑亦可使用市售品,可舉出San-ai bac P、San-ai bac 300K、San-ai bac IT-15SA、San-ai bac AS-30、San-ai bac T-10、San-ai bac M-30、San-ai bac Sodium Omadine(皆為三愛石油製)等。
作為上述導電性物質,可舉例如金屬、金屬的氧化物、導電性碳及導電性聚合物等。
作為上述金屬,可舉例如金、銀、銅、鉑、鋅、鐵、鉛、錫、鋁、鈷、銦、鎳、鉻、鈦、銻、鉍、鍺及鎘等的金屬、以及由錫-鉛合金、錫-銅合金、錫-銀合金及錫-鉛-銀合金等的2種類以上的金屬所構成的合金等。其中,以鎳、銅、銀或金為較佳。
作為上述導電性碳,可舉例如科琴黑、乙炔黑、爐黑、槽法碳黑等的碳黑、富勒烯、奈米碳管、奈米碳纖維、石墨烯、無定形碳、碳纖維、天然石墨、人造石墨、石墨化科琴黑及中孔洞碳等。
作為上述導電性聚合物,可舉例如聚乙炔、聚吡咯、聚(3-甲基吡咯)、聚(3-丁基吡咯)、聚(3-辛基吡咯)、聚(3-癸基吡咯)、聚(3,4-二甲基吡咯)、聚(3,4-二丁基吡咯)、聚(3-羥基吡咯)、聚(3-甲基-4-羥基吡咯)、聚(3-甲氧基吡咯)、聚(3-乙氧基吡咯)、聚(3-辛氧基吡咯)、聚(3-羧基吡咯)、聚(3-甲基-4-羧基吡咯)、聚N-甲基吡咯、聚噻吩、聚(3-甲基噻吩)、聚(3-丁基噻吩)、聚(3-辛基噻吩)、聚(3-癸基噻吩)、聚(3-十二烷基噻吩)、聚(3-甲氧基噻吩)、聚(3-乙氧基噻吩)、聚(3-辛氧基噻吩)、聚(3-羧基噻吩)、聚(3-甲基-4-羧基噻吩)、聚(3,4-乙烯二氧噻吩)、聚苯胺、聚(2-甲基苯胺)、聚(2-辛基苯胺)、聚(2-異丁基苯胺)、聚(3-異丁基苯胺)、聚(2-苯胺磺酸)、聚(3-苯胺磺酸)及對於聚噻吩衍生物(PEDOT:聚(3,4)-乙烯二氧噻吩)摻雜聚苯乙烯磺酸(PSS)而成者等。
又,只要不損及本發明之效果,除上述以外因應所需亦可添加光聚合起始劑、熱聚合起始劑、光鹼起始劑、酸產生劑、無機填充料、有機填充料、消泡劑、增稠劑、調平劑、有機金屬偶合劑、觸變劑、碳化合物、金屬微粒子、金屬氧化物、耐燃劑、可塑劑、光穩定劑、熱穩定劑、抗老化劑、彈性物粒子、鏈轉移劑、聚合抑制劑、紫外線吸收劑、抗氧化劑、抗靜電劑、脫模劑、流動調整劑、密著促進劑、不飽和單體、環氧化合物・氧雜環丁烷化合物・乙烯基醚等的陽離子聚合性化合物等的各種樹脂添加物等。
接下來,對於本發明之硬化物之製造方法來進行說明。 本發明之硬化物之製造方法係藉由光照射或加熱來使本發明之水溶性組成物硬化。關於使用本發明之水溶性組成物的硬化物的製造方法。將較佳的塗佈方法、硬化條件表示於下述。
較佳的塗佈方法係利用旋轉塗佈機、棒塗佈機、輥塗佈機、淋幕式塗佈機、各種的印刷、浸漬等的周知的方法,來適用於玻璃、金屬、紙、塑膠等的支撐基體上。又,一旦施予在薄膜等的支撐基體上後,亦可轉印至其他的支撐基體上,其適用方法並無限制。
作為透明支撐體的材料,可舉例如玻璃等的無機材料;二乙醯纖維素、三乙醯纖維素(TAC)、丙醯纖維素、丁醯纖維素、乙醯基丙醯纖維素、硝化纖維素等的纖維素酯;聚醯胺;聚碳酸酯;聚對苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯、聚對苯二甲酸丁二醇酯、聚-1,4-環己烷對苯二甲酸二甲酯、聚乙烯-1,2-二苯氧基乙烷-4,4’-二羧酸酯、聚對苯二甲酸丁二酯等的聚酯;聚苯乙烯;聚乙烯、聚丙烯、聚甲基戊烯等的聚烯烴;聚甲基丙烯酸甲酯等的丙烯酸系樹脂;聚碳酸酯;聚碸;聚醚碸;聚醚酮;聚醚醯亞胺;聚氧乙烯、降莰烯樹脂等的高分子材料。透明支撐體的透過率係以80%以上為較佳,以86%以上為更佳。霧度係以2%以下為較佳,以1%以下為更佳。折射率係以1.45~1.70為較佳。
較佳的硬化條件係將本發明之水溶性組成物塗佈在透明支撐體上後進行光照射之情形時,所照射的光的波長、強度及照射時間等的照射條件係可藉由光起始劑的活性、所使用的光聚合性樹脂的活性等來做適當調整,但通常為了使光充分地進入內部,作為光波長係以波長波峰300~500nm者為較佳,又較佳為波長波峰350~450nm,最佳為波長波峰360~380nm。又,作為光強度係以10~300 mW/cm2
為較佳,又較佳為25~100mW/cm2
,照射時間係以5~500秒鐘為較佳,又較佳為10~300秒鐘。
藉由將本發明之水溶性組成物塗佈至透明支撐體上後進行加熱,亦可使交聯反應進行。加熱為50~200℃,較佳為70~150℃下進行10~1小時。低於50℃時將會有無法進行交聯反應之虞,若高於200℃時,將會有發生構成成分的分解、或光學薄膜的透明性降低之虞。
藉由光微影法(以下也稱為「光刻法」)來製作硬化物的圖型之情形時,藉由觸針式形狀測定器(Ulvac製Dektak150),使用條件調整以膜厚成為5.0~5.5μm之方式的旋轉塗佈機,將本發明之水溶性組成物塗佈至玻璃基板上後,利用90℃的加熱板進行10分鐘預烤。之後,冷卻至室溫,使用高壓水銀燈,透過光罩(LINE/SPACE=50μm/50 μm)來照射包含365nm的波長的光500mJ/cm2
,並在23℃的離子交換水中浸漬1分鐘後,利用氣槍去除附著的水,在140℃的烤箱內使基板乾燥30分鐘。較佳的硬化條件係與上述為相同。
本發明之硬化物係由本發明之水溶性組成物所成。作為本發明之水溶性組成物之具體的用途,可舉出眼鏡、攝影用透鏡所代表的光學材料、塗料、各種塗佈劑、襯裡劑、油墨、光阻劑、液狀光阻劑、接著劑、液晶滴液工法用密封劑、圖像形成材料、圖型形成材料、印刷版、絕緣清漆、絕緣薄片、層合板、印刷版、半導體裝置用・LED封裝用・液晶注入口用・有機EL用・光元件用・電絕緣用・電子零件用・分離膜用等的密封劑、成形材料、二次電池的電極、分隔板、油灰、建材、線板、玻璃纖維含浸劑、填縫劑、半導體用・太陽電池用等的鈍化膜、層間絕緣膜、保護膜、液晶顯示裝置的背光所使用的稜鏡透鏡薄片、投影電視等的螢幕所使用的菲涅耳透鏡薄片、雙凸透鏡薄片等的透鏡薄片的透鏡部、或使用如此般薄片的背光等、液晶濾色器的保護膜或間隔器、DNA分離晶片、微反應器、奈米生物裝置、硬碟用記錄材料、固體攝影元件、太陽電池面板、發光二極體、有機發光裝置、發光薄膜、螢光薄膜、MEMS元件、致動器、全像片、電漿裝置、偏光板、偏光薄膜、微透鏡等的光學透鏡、光學元件、光偶合器、光導波路、光學的造形用注模劑等,作為例如可適用為塗佈劑的基材,可舉出金屬、木材、橡膠、塑膠、玻璃、陶瓷製品等。
將本發明之水溶性組成物使用在光學薄膜之情形時,光學薄膜係可利用慣用的方法形成薄膜或薄片成形,且無需延伸所得到的薄膜或薄片(或配向處理)而可製造,或亦可藉由延伸(或配向處理)來製造。薄膜成形係可以利用擠壓成形、吹氣成形等的熔融成形法(熔融製膜法)、或亦可利用流延成形法(流延製膜法、溶液流延法)。
使用本發明之水溶性組成物的光學薄膜,關於形狀並無特別限制,但通常可舉出利用在透明支撐體上具有光學膜的光學用途的薄膜、使用在液晶顯示裝置等的偏光板用保護薄膜、相位差薄膜、視野角擴大薄膜、利用在電漿顯示器的抗反射薄膜、低反射率薄膜等的各種機能薄膜、或有機EL顯示器等所使用的各種機能薄膜等。
使用本發明之水溶性組成物而得的光學薄膜,可使用作為將光學薄膜適用在支撐體而成的追蹤型光碟片(CD±R、DVD±R、次世代型高密度碟片等)的光學記錄層;各種透鏡;圖像顯示裝置用光學過濾器;濾色器、變色過濾器所代表的各種過濾器;或有機EL發光元件、無機EL發光元件或電子紙顯示體等的保護密封薄膜。 [實施例]
以下為舉出實施例等來更詳細地說明本發明,但本發明並非被限定於該等的實施例中。尚,所謂本實施例中記載的固形分係意味著去除溶劑後的成分所佔的質量%。
[製造例1:苯基(2,4,6-三甲基苯甲醯基)膦酸的合成] 在附有迴流管的反應燒瓶中加入2,4,6-三甲基苯甲醯基苯基膦酸乙酯(ethyl(2,4,6-trimethylbenzoyl) phenylphosphinate)71.2g(225mmol)、2-丁酮(MEK)420g,並在氮氣流下、以室溫下一邊攪拌一邊使其溶解。添加碘化鈉35.4g(236mmol),直接在室溫下攪拌15分鐘後,使其升溫至65℃。繼續以65℃下攪拌8小時後,冷卻至室溫並過濾析出物,以MEK100g來洗淨過濾物。在減壓下以60℃使其乾燥,從而可得到53.8g(收率77.2%)的苯基(2,4,6-三甲基苯甲醯基)膦酸鈉。在附有迴流管的反應燒瓶中加入苯基(2,4,6-三甲基苯甲醯基)膦酸鈉50.0g(161mmol)、離子交換水278g,一邊攪拌一邊使其完全地溶解。之後,在室溫下滴入濃硫酸15.8g與離子交換水553g的混合液,並直接繼續攪拌2小時。過濾析出物,並利用水100ml來洗淨二次。利用60℃溫風烤箱來使過濾物乾燥,從而得到淡黃色結晶42.3g(收率91.2%)。
<實施例1-1:4-甲基嗎啉-4-鎓=苯基(2,4,6-三甲基苯甲醯基)膦酸鹽(醯基膦酸鹽No.1)的合成> 在反應燒瓶中加入苯基(2,4,6-三甲基苯甲醯基)膦酸3.0g(10.4mmol)、二氯甲烷15ml,在室溫下一邊攪拌一邊使其完全地溶解。緩慢地加入4-甲基嗎啉(4- methylmorpholine)1.05g(10.4mmol),並直接在室溫下繼續攪拌2小時。過濾不溶物後,進行脫溶劑並利用己烷洗淨殘渣,進行減壓乾燥後從而得到作為淡黃色的結晶之收量3.8g(收率93.8%)的醯基膦酸鹽No.1(下述構造)。將分析結果表示於[表1]及[表2]。
<實施例1-2:吡咯啶-1-鎓=苯基(2,4,6-三甲基苯甲醯基)膦酸鹽(醯基膦酸鹽No.2)的合成> 在反應燒瓶中加入苯基(2,4,6-三甲基苯甲醯基)膦酸1.0g(3.5mmol)、二氯甲烷5ml,在室溫下一邊攪拌一邊使其完全地溶解。緩慢地加入吡咯啶(pyrrolidine)0.25g (3.5mmol),並直接在室溫下繼續攪拌2小時。過濾不溶物後,進行脫溶劑並利用己烷洗淨殘渣,進行減壓乾燥後從而得到作為淡褐色的結晶之收量1.0g(收率80.0%)的醯基膦酸鹽No.2(下述構造)。將分析結果表示於[表1]及[表2]。
<實施例1-3:1-苄基-4-羥基哌啶-1-鎓=(苯基(2,4,6-三甲基苯甲醯基)膦酸鹽(醯基膦酸鹽No.3)的合成> 在反應燒瓶中加入苯基(2,4,6-三甲基苯甲醯基)膦酸1.0g(3.47mmol)、二氯甲烷5ml,在室溫下一邊攪拌一邊使其完全地溶解。滴入溶解在二氯甲烷3ml中的1-苄基-4-羥基哌啶(1-benzyl-4-hydroxypiperidine)0.796g(4.16mmol),並直接在室溫下繼續攪拌3小時。利用己烷洗淨將反應溶液進行脫溶劑的殘渣,並進行減壓乾燥後,從而得到作為淡黃色的結晶之收量1.5g(收率90.4%)的醯基膦酸鹽No.3(下述構造)。將分析結果表示於[表1]及[表2]。
<實施例1-4:N,N-雙(2-羥基乙基)丁烷-1-銨(aminium)=苯基(2,4,6-三甲基苯甲醯基)膦酸鹽(醯基膦酸鹽No.4)的合成> 在反應燒瓶中加入苯基(2,4,6-三甲基苯甲醯基)膦酸5.0g(17.3mmol)、二氯甲烷50ml,在室溫下一邊攪拌一邊使其完全地溶解。加入N-丁基二乙醇胺(N- butyldiethanolamine)2.8g(17.3mmol),直接在室溫下繼續攪拌5小時。將反應溶液進行脫溶劑,利用己烷洗淨將冷卻至10℃以下並固化的殘渣,並進行減壓乾燥後,從而得到作為淡黃色的結晶之收量7.5g(收率97.4%)的醯基膦酸鹽No.4(下述構造)。將分析結果表示於[表1]及[表2]。
[製造例2:具有感光基及羥基之水溶性聚合物水溶液No.1] 在已加入1000份的離子交換水的反應燒瓶中,緩慢地投入作為含有羥基之聚合物之Nichigo G-Polymer OKS-1083(皂化度99;日本合成化學工業製)138份,並攪拌1小時後,加溫至90℃來使其完全地溶解。冷卻至40℃,投入羥基2mol%份之作為感光基賦予劑之甲醯基苯乙烯基吡啶鎓與磷酸0.7份,並以40℃下繼續攪拌2小時。將溶液冷卻至室溫後,以固形分成為15%之方式來追加離子交換水,以室溫下進而進行攪拌1小時,並利用5μm過濾器進行過濾後,加入離子交換水將固形分調整成10質量%,從而得到具有感光基及羥基之水溶性聚合物水溶液No.1。
[製造例3:具有感光基及羥基之水溶性聚合物水溶液No.2] 在已加入1000份的離子交換水的反應燒瓶中,緩慢地投入[表1]所表示之作為含有羥基之聚合物之Gohsenol GL-05(皂化度87;日本合成化學工業製)138份,並攪拌1小時後,加溫至90℃來使其完全地溶解。冷卻至50℃,投入作為感光性賦予劑之羥基2mol%份之N-羥甲基丙烯醯胺與p-甲苯磺酸0.1份,並以50℃下繼續攪拌3小時。將溶液冷卻至室溫後,追加離子交換水,以室溫下進而進行攪拌1小時,並利用5μm過濾器進行過濾後,加入離子交換水將固形分調整成10質量%,從而得到具有感光基及羥基之水溶性聚合物水溶液No.2。
[製造例4:聚乙烯醇改質水溶性聚合物水溶液No.1] 將聚乙烯醇Gohsenol NL-05(皂化度98;日本合成化學工業製)10.0g緩慢地添加在攪拌中的離子交換水90.0g中,並直接在室溫下攪拌1小時。之後,將內溫從85℃調整至90℃,並繼續攪拌2小時。確認溶解後,冷卻至室溫並利用1μm過濾器進行過濾後,加入離子交換水將固形分調整成10質量%,從而得到聚乙烯醇改質水溶性聚合物水溶液No.1。
[製造例5:聚乙烯醇改質水溶性聚合物水溶液No.2] 將GOHSENX Z-200(皂化度99;日本合成化學工業製)10.0g緩慢地添加在攪拌中的離子交換水90.0g中,並直接在室溫下攪拌1小時。之後,將內溫從85℃調整至90℃,並繼續攪拌2小時。確認溶解後,冷卻至室溫並利用1μm過濾器進行過濾,從而得到聚乙烯醇改質水溶性聚合物水溶液No.2。
[製造例6:聚吡咯啶酮水溶液No.1] 將作為聚乙烯基吡咯啶酮(polyvinylpyrrolidone)之K90(日本觸媒製)10.0g緩慢地添加在攪拌中的離子交換水90.0g中,並直接在室溫下攪拌1小時。之後,將內溫從85℃調整至90℃,並繼續攪拌2小時。確認溶解後,冷卻至室溫並利用1μm過濾器進行過濾,從而得到聚吡咯啶酮水溶液No.1。
<實施例2-1~2-24及比較例2-1~2-8:水溶性組成物之調製> 根據[表3]~[表6]的調配,將各成分在室溫下攪拌1小時後,利用1μm過濾器來進行過濾,從而得到水溶性組成物(實施例2-1~2-24及比較例2-1~2-8)。尚,表中之調配之數值表示為質量份。又,表中之各成分的符號表示為下述之成分。 A-1:醯基膦酸鹽No.1 [本發明之醯基膦酸鹽(A)] A-2:醯基膦酸鹽No.2 [本發明之醯基膦酸鹽(A)] A-3:醯基膦酸鹽No.3 [本發明之醯基膦酸鹽(A)] A-4:醯基膦酸鹽No.4 [醯基膦酸鹽(A)] A-5:醯基膦酸鹽No.5 [醯基膦酸鹽(A):下述中記載構造] A-6’:比較自由基起始劑No.1 [下述中記載構造] A-7’:比較自由基起始劑No.2 [下述中記載構造] A-8’:比較自由基起始劑No.3 [下述中記載構造] B-1:NK EsterA-GLY-20E [化合物(B)] (環氧烷烴改質丙烯酸酯;新中村化學工業製) B-2:NK Ekonoma A-PG5054E [化合物(B)] (環氧烷烴改質丙烯酸酯;新中村化學工業製) B-3:FFM-2 [化合物(B)] (多官能丙烯醯胺化合物;Fujifilm製) B-4:丙烯醯嗎啉(acryloylmorpholine) B-5:羥基丙烯醯胺 C-1:BONJET BLACK CW-1 [著色劑(C)] (改質碳黑自分散體、濃度20%;Orient化學工業公司製) C-2:MICROPIGMO WMRD-5 [著色劑(C)] (Pigment Red17樹脂分散體、濃度20%;Orient化學工業公司製) C-3:MICROPIGMO WMGN-5 [著色劑(C)] (Pigment Green7樹脂分散體、濃度21%;Orient化學工業公司製) C-4:MICROPIGMO WMBE-5 [著色劑(C)] (Pigment Blue15:6樹脂分散體、濃度20%;Orient化學工業公司製) D-1:具有感光基及羥基之水溶性聚合物水溶液No.1 D-2:具有感光基及羥基之水溶性聚合物水溶液No.2 D-3:聚乙烯醇改質水溶性聚合物水溶液No.1 D-4:聚乙烯醇改質水溶性聚合物水溶液No.2 D-5:聚吡咯啶酮水溶液No.1 E-1:MEGAFACE F-444(氟系調平劑;DIC製) E-2:Orgatix ZC-126 (氯化鋯水溶液:成分濃度30%、Zr含有量11% ;Matsumoto Fine Chemical製) E-3:Orgatix WS-700 (有機鈦改質聚乙烯亞胺、成分濃度10%水溶液;Matsumoto Fine Chemical製)
[水溶性組成物及硬化物之評估] 對於各水溶性組成物(實施例2-1~2-24及比較例2-1~2-8),依下述流程來進行相溶性、塗佈性、光微影性及硬化物之耐濕熱性、及LED光源下之硬化性之評估。將結果合併紀錄在[表3]~[表6]中。
(相溶性) 利用目視確認各水溶性組成物(實施例2-1~2-19及比較例2-1~2-6)之狀態,並依據下述之基準來進行評估。 ◎:透明均勻 ○:微白濁 △:白濁 × :未相溶且可發現凝膠化或不溶物 ××:在室溫放置1日以內可發現析出、凝膠化或不溶物 若評估為◎或○者,則可較佳使用;若為◎者,則可為特佳使用;若評估為△者,則可藉由處理後來使用;若評估為×或××者,則不適合使用。
(含有著色劑之水溶性組成物之相溶性) 利用目視確認含有各著色劑之水溶性組成物(實施例2-20~2-24及比較例2-7、2-8)之狀態,並依據下述之基準來進行評估。 ○:均勻 × :未相溶且可發現凝膠化或不溶物 若評估為○者,則可較佳使用;若評估為×者,則不適合使用。
(塗佈性) 藉由觸針式形狀測定器(Ulvac製Dektak150),使用條件調整以膜厚成為5.0~5.5μm之方式的旋轉塗佈機,將各水溶性組成物(實施例2-1~2-24及比較例2-1~2-8)塗佈至玻璃基板上後,利用90℃的加熱板進行10分鐘預烤。利用目視確認此時的膜之狀態,依據下述之基準來進行評估。 ○:塗佈膜為透明均勻 × :可確認在表面有不均等不均勻之狀態或析出物 若評估為○者,則可較佳使用;若評估為×者,則不適合使用。
(光微影性) 藉由處針式形狀測定器(Ulvac製Dektak150),使用條件調整以膜厚成為5.0~5.5μm之方式的旋轉塗佈機,將各水溶性組成物(實施例2-1~2-24及比較例2-1~2-8)塗佈至玻璃基板上後,利用90℃的加熱板進行10分鐘預烤。之後,冷卻至室溫,並使用高壓水銀燈透過光罩(LINE/SPACE= 50μm/50μm),照射300mJ/cm2
的包含365nm的波長的光,並在23℃的離子交換水中浸漬1分鐘後,利用氣槍去除附著的水,在140℃的烤箱內使基板乾燥30分鐘。利用雷射顯微鏡確認乾燥後的圖型,並依據下述之基準來進行評估。 ○:圖型為50±3μm以內 △:50±10μm以內 × :超過50±10μm或未有圖型 若評估結果為○或△者,則可使用作為圖型形成劑,其中為○者,可為特佳使用;評估結果為×者,則不適合於需要圖型形成之用途。
(耐濕熱性) 藉由觸針式形狀測定器(Ulvac製Dektak150),使用條件調整以膜厚成為5.0~5.5μm之方式的旋轉塗佈機,將各水溶性組成物(實施例2-1~2-24及比較例2-1~2-8)塗佈至玻璃基板上後,利用90℃的加熱板進行10分鐘預烤。之後,冷卻至室溫後,使用高壓水銀燈照射500mJ/cm2
的包含365nm的波長的光,在140℃的烤箱內使基板乾燥30分鐘。將所得到的硬化物以85℃、85%RH的條件下放置24小時後,相同地測定硬化物的霧度。在耐濕性試驗前後,依據下述之基準來進行評估。 〇:霧度的變化量為未滿1.0 △:霧度的變化量為1以上未滿3 × :霧度的變化量為3以上 ××:膜的一部分為剝離或者溶出 評估結果若為○或△的硬化物,則可使用在要求耐濕熱性之用途,耐濕熱性之優異順序,依序為○、△。其中〇的硬化物,則特別適合在要求耐濕熱性之用途。另一方面,×及××的硬化物,則無法使用在要求耐濕熱性之用途。
(LED光源下之硬化性) 使用實施例2-13、2-15及2-16以及比較例2-4及2-5的組成物,並利用塗佈機塗佈至玻璃基板上,經曝光(365 nmLED光源、100mJ/cm2
)後,在23℃的離子交換水中浸漬30秒鐘,確認以140℃下乾燥10分鐘後的膜厚的變化(不浸漬於水,僅只曝光、乾燥的塗佈膜的膜厚為15μm)。
相較於實施例2-13、2-15及2-16之殘膜率分別為93%、92%、90%,比較例2-4之殘膜率為54%、比較例2-5之殘膜率為65%。根據以上結果可說明,本發明之水溶性組成物即使是對於LED光源曝光亦可展現出優異的硬化特性。
根據[表3]~[表6]可得知,本發明之水溶性組成物之相溶性為高、塗佈性為優異、光微影性為優異,所得到的硬化物之耐濕熱性為良好。因此,本發明之水溶性組成物係可適合使用在油墨、圖像形成材料及圖型形成劑等之用途,本發明之硬化物係可適合使用在光學薄膜等之用途。
Claims (9)
- 一種水溶性組成物,其特徵係含有:下述一般式(I)所表示之醯基膦酸鹽(A)、與具有下述一般式(II)所表示之基之化合物(B),
- 如請求項1之水溶性組成物,其中,前述一般式(I)中之X1為2,4,6-三甲基苯基。
- 如請求項1或2之水溶性組成物,其中,前述一般式(I)中之Am+為N+HY1Y2Y3、且Y1、Y2及Y3中任一者以上的氫原子係被羥基所取代。
- 如請求項1或2之水溶性組成物,其中,前述一般式(II)中之Z1為-NR2-。
- 如請求項1或2之水溶性組成物,其中,進而含有著色劑(C)。
- 一種硬化物之製造方法,其特徵係藉由光照射或加熱來使請求項1~5中任一項之水溶性組成物硬化。
- 一種硬化物,其特徵係由請求項1~5中任一項之水溶性組成物所得到。
- 一種醯基膦酸鹽,其係下述一般式(I)所表示之醯基膦酸鹽,
- 如請求項8之醯基膦酸鹽,其中,前述一般式(I)中之Am+為N+HY1Y2Y3、且Y1、Y2及Y3中任一者以上的氫原子係被羥基所取代。
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JP7276161B2 (ja) * | 2018-02-07 | 2023-05-18 | 三菱ケミカル株式会社 | 光硬化性組成物、造形物及びハイドロゲル |
CN111936924A (zh) * | 2018-05-25 | 2020-11-13 | 积水化学工业株式会社 | 液晶显示元件用密封剂、上下导通材料、及液晶显示元件 |
US20240117081A1 (en) * | 2019-11-14 | 2024-04-11 | Adeka Corporation | Polymerizable composition, vehicle, cured material, and method of manufacturing cured material |
KR20220106959A (ko) | 2019-11-25 | 2022-08-01 | 가부시키가이샤 아데카 | 아실포스핀 조성물, 중합 개시제, 중합성 조성물과, 경화물 및 그 제조 방법 |
US11397826B2 (en) | 2020-10-29 | 2022-07-26 | Snowflake Inc. | Row-level security |
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TW201843187A (zh) | 2018-12-16 |
EP3597670A4 (en) | 2020-09-09 |
KR20190125344A (ko) | 2019-11-06 |
JP6901292B2 (ja) | 2021-07-14 |
KR102498324B1 (ko) | 2023-02-08 |
US11649334B2 (en) | 2023-05-16 |
JP2018150497A (ja) | 2018-09-27 |
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CN110337454A (zh) | 2019-10-15 |
WO2018168870A1 (ja) | 2018-09-20 |
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