CN1107484A - 由丙烯酸聚合物组成的无液滴薄膜或片材及其制备方法 - Google Patents
由丙烯酸聚合物组成的无液滴薄膜或片材及其制备方法 Download PDFInfo
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- CN1107484A CN1107484A CN94113833A CN94113833A CN1107484A CN 1107484 A CN1107484 A CN 1107484A CN 94113833 A CN94113833 A CN 94113833A CN 94113833 A CN94113833 A CN 94113833A CN 1107484 A CN1107484 A CN 1107484A
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- 238000002360 preparation method Methods 0.000 title claims description 10
- 229920000058 polyacrylate Polymers 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims abstract description 20
- 239000004926 polymethyl methacrylate Substances 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 33
- 238000000576 coating method Methods 0.000 claims description 29
- 239000011248 coating agent Substances 0.000 claims description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 239000000377 silicon dioxide Substances 0.000 claims description 11
- 229910044991 metal oxide Inorganic materials 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical group C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 150000004706 metal oxides Chemical class 0.000 claims description 6
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 5
- 238000009736 wetting Methods 0.000 claims description 5
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- -1 hexanediyl ester Chemical class 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- OQIOVJHINWLQCM-UHFFFAOYSA-J dizinc prop-2-enoate Chemical compound [Zn++].[Zn++].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C OQIOVJHINWLQCM-UHFFFAOYSA-J 0.000 claims description 3
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- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001298 alcohols Chemical class 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 2
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- 239000000539 dimer Substances 0.000 claims description 2
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- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 1
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- 239000003999 initiator Substances 0.000 description 7
- OGBWMWKMTUSNKE-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CCCCCC(OC(=O)C(C)=C)OC(=O)C(C)=C OGBWMWKMTUSNKE-UHFFFAOYSA-N 0.000 description 5
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- 229920000642 polymer Polymers 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- OWDBMKZHFCSOOL-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)propoxy]propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(C)COC(C)COC(=O)C(C)=C OWDBMKZHFCSOOL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- NGMNTLCQDNNBNT-UHFFFAOYSA-N C(C=C)(=O)OC.C(CS)(=O)OCCOC(CS)=O Chemical compound C(C=C)(=O)OC.C(CS)(=O)OCCOC(CS)=O NGMNTLCQDNNBNT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- INXWLSDYDXPENO-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CO)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C INXWLSDYDXPENO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 230000008030 elimination Effects 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- YOQPJXKVVLAWRU-UHFFFAOYSA-N ethyl carbamate;methyl prop-2-enoate Chemical compound CCOC(N)=O.COC(=O)C=C YOQPJXKVVLAWRU-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
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- 210000003746 feather Anatomy 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
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Classifications
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J7/04—Coating
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
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- 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
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- 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
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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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- 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
- C08J2433/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/256—Heavy metal or aluminum or compound thereof
- Y10T428/257—Iron oxide or aluminum oxide
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/259—Silicic material
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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Abstract
具有无液滴和消雾性的薄膜、片材和成型件产
品,该产品包括由丙烯酸聚合物构成的基材和单体组
合物涂层。所述单体组合物的组成如说明书所述。
Description
本发明涉及无液滴和消雾性产品,尤其涉及薄膜和片材。所述产品包括由丙烯酸聚合物构成的载体和聚合的紫外线固化涂层。所述涂层是包含特定丙烯酸单体与少量亲水性金属氧化物的混合物。
众所周知,基于诸如聚甲基丙烯酸甲酯之类的热塑料聚合物透明片材在使用时通常存在的问题之一是水以或大或小的液滴形式凝结在表面上,从而降低了透明片材的透明性。
先有技术提出了多种所述片材的表面处理方法,以解决上述问题,但是效果不佳,因为无液滴性能的保持时间太短或者要采用复杂的和造成污染的方法,对于丙烯酸片材还产生不希望的泛黄。
专利DE 3400079描述了一种处理丙烯酸聚合物尤其是聚甲基丙烯酸甲酯的方法,它是用不溶于水的、极性基团含量适中的聚合物以其溶液或分散体的形式施用而涂上第一层表面涂层,然后通过将胶状二氧化硅或不溶于水的胶状金属氧化物以其溶液或分散体的形式再喷上一层涂层。
该方法复杂且耗资,因为它包括先后施以两层涂层。由于使用溶剂,它可产生污染。而且施加涂层与聚合物片材之间的粘附也不好。
欧洲专利申请EP 374516描述了这样的方法:在热塑性聚合物尤其是聚碳酸酯透明片材上涂上由至少92%(重量)有机溶剂和0-8%下述物质组成的混合物所构成的溶液:
a)可固化的多官能团芳族单体,尤其是1,6-己二醇二丙烯酸酯,
b)胶状金属氧化物,尤其是二氧化硅,和
c)紫外线交联剂,通常用量为1-10%(重量);其中b/a重量比为1.9-19。随后用紫外光将所述溶液固化,形成含65-95%(重量)胶状金属氧化物的交联涂层。
该方法由于使用分散大量金属氧化物所需的大量污染性和毒性溶剂,使得热塑性片材不透明,并且由于使用大量紫外线交联催化剂,使得聚合物片材产生不希望的浅黄色,因而是不利的。
欧洲专利申请EP317410描述了用一种丙烯酸单体混合物来处理聚甲基丙烯酸片材(PMMA)的方法,所述混合物包含至少40%(重量)丙烯酸或甲基丙烯酸,至少0.1-5%(重量)紫外光聚合引发剂。随后用紫外光使施用单体聚合。
这样的处理会引起PMMA一定程度的泛黄,因为使用了大量引起泛黄的紫外线引发剂,还使用了通常含有大量阻聚剂的大量(甲基)丙烯酸。此外,还需要大量所述丙烯酸,它们是挥发性和刺激性的,带来毒性和污染问题。
在本发明人的共同未决的意大利专利申请第MI 92A001300号中,描述了无液滴涂料,它由丙烯酸单体的混合物制得,能够避免先有技术的不便之处。
在进行研究的过程中,本发明人现在通过采用其它丙烯酸单体混合物的方法进一步改进了所述涂料,尤其改进了雾度和透明度方面的性能。
现在我们发现了一种通用的简单而无污染的方法,它能使基于丙烯酸聚合物、尤其是PMMA的薄膜、片材和成型件表面无液滴和消雾,它不产生已知方法的不便。该方法包括用特定的含有少量亲水性胶状金属氧化物的丙烯酸单体混合物涂覆成型件的表面,然后用紫外光使所述混合物就地聚合和交联。
该方法可以与成型件的制备构成一个整体而仅成为一个阶段。在该方法中,不必使用有机溶剂,并且通常不使用紫外线聚合引发剂或者仅使用低于0.06%的有限量的紫外线聚合引发剂。
这样制得的成型件具有很好的无液滴性和消雾性、良好的表面硬度、可忽略的或很低的黄度指数、良好的抗静电性。对于透明件,其透明度基本上保持不变。
此外,这样施加的无液滴层对成型件表面的粘着力强,该涂层稳定、耐磨、耐洗涤并且在鉴定期间保持不变。
本发明的目的是提供具有无液滴和消雾性的产品,如薄膜、片材和成型件,该产品包括由丙烯酸聚合物构成的基材和组成如下的涂层:
a) 50-70%(重量)C2-C18脂肪二醇或由1-6个C2-C4氧化烯单元形成的(聚)氧化烯的丙烯酸或甲基丙烯酸酯;
b) 10-30%(重量)的下式单体或其低聚物,
式中R是H,CH3;R2是C2-C6羟基烷基或乙氧基基团-(CH2-CH2O)n-H,其中n是一个1-10的整数;
c) 10-30%、优选15-20%(重量)丙烯酸或甲基丙烯酸或含有式(Ⅱ)基团的丙烯酸或甲基丙烯酸单体或者优选其二聚体或其衍生物,可选地和优选地是部分盐化的,最好不超过10%,最好是用氨、金属离子或铵盐化的。式(Ⅱ)如下:
式中,R具有上述意义,
d) 1-10%(重量)交联剂,它由一种或多种多官能团醇的丙烯酸酯或甲基丙烯酸酯组成,具有至少三个双键,但不包括a)类的成分;
e) 每100重量份a+b+c+d,0.01-3重量份、优选0.05-1重量份、更优选0.1-0.5重量份亲水性胶状金属氧化物;
f) 每100重量份a+b+c+d,0-0.06重量份紫外线聚合引发剂,a)、b)、c)、d)之和为100,其中所述涂层用紫外线聚合并交联。
如果a、b、c以及可选的d成分含有工业产品常加的阻聚剂的话,则优选使用较大量的的聚合引发剂f),通常用量为100-200ppm。这是为了消除阻聚剂的作用。
正如本领域公知的,在本发明混合物中每100份混合物也可使用0-4份紫外光吸收剂。
在这种情况下,f)的量优选与紫外光吸收剂的量相近。
这样便可获得较好的耐大气老化性的优点。
当化合物f)高于0.06份时,上面已说过,片材便出现着色的问题。
本申请人意外地发现,通过将紫外光过滤以除去大部分波长低于300nm的光便能够消除该着色现象。
这可例如用Pyrex过滤器获得。
因此,为了不过度损害聚合动力学,我们发现在氮气流、优选在富氮空气流中进行聚合是适宜的。
就形成载体的丙烯酸聚合物而言,可以使用通常为透明的丙烯酸酯或甲基丙烯酸酯的均聚物和共聚物,优选聚甲基丙烯酸甲酯(PMMA)或其与例如聚氯乙烯(PVC)和聚偏氟乙烯(PVdF)的透明合金。
就成分a)的单体而言,优选使用己二醇二甲基丙烯酸酯(HDDA)、三缩丙二醇二甲基丙烯酸酯、乙二醇二(甲基)丙烯酸酯(EGDM)、四甘醇二(甲基)丙烯酸酯(TEGDM)。
就成分b)的单体而言,可以使用丙烯酸羟乙酯和羟丙酯或甲基丙烯酸羟乙酯和羟丙酯,优选(甲基)丙烯酸α-羟乙酯。
就c)所述的化合物而言,可以使用例如丙烯酸、甲基丙烯酸、β-羧乙基丙烯酸和二丙烯酸锌、铵或钠。
就成网剂(reticulation agent)而言,可以使用例如季戊四醇三丙烯酸酯(PETIA)、二羟甲基丙烷三丙烯酸酯、二季戊四醇五丙烯酸酯、季戊四醇四丙烯酸酯。
就交联剂而言,也可以使用聚氨酯类聚(甲基)丙烯酸酯,例如脂族氨基甲酸酯六(甲基)丙烯酸酯、氨基甲酸酯三(甲基)丙烯酸酯,它们可通过二元醇与异氰酸酯与(甲基)丙烯酸羟乙酯的反应制得。
就亲水性胶状金属氧化物而言,可以使用例如将诸如TYXOSY L38
(Rh
ne-Poulenc)沉淀或者将诸如HDK N20
(Wacker)燃烧获得的亲水性胶状二氧化硅,以及氢氧化铝,优选使用胶状二氧化硅。
使用少量紫外线聚合引发剂是有用的,它优选是基于二苯甲酮的,例如ESACURE KT 37
与UVECRYC P115
(Fratelli Lamberti)的混合物,或Irgacure 500
(CIBA-GEIGY)。也可使用Darocur 1173
和上述欧洲专利374516所述的其它化合物。
制备包括丙烯酸聚合物薄膜、片材和成型件的无液滴和消雾性产品的方法,它包括在所述产品表面均匀地涂上一层具有前述组成的单体组合物a)+b)+c)+d)+e)+f),然后使该涂覆产品经受紫外线幅射以便将涂层聚合并交联。
由于本发明简单且用途广泛,因而它可以在工厂中连续进行,可以与载体成型件的制备、尤其是与丙烯酸薄膜和丙烯酸片材的制膜或挤出制造构成一体。
更具体地说,该方法在工业上可以这样实施:以协调的方式在挤出片材例如PMMA片材从挤出口模中出来时,直接地和连续地将单体混合物涂于其上,尤其是双面涂覆,然后通常是连续地使涂覆的片材经受紫外线灯幅射。该方法的又一优点是形成涂覆混合物的单体的蒸发被降至最低限度。
单体混合物的粘度可通过改变各单体、聚合物和二氧化硅的用量而任意调节,它可以工业上采用的任一种涂覆方法(例如喷涂或涂布的方法)施工,以形成均匀涂层。
片材表面最好十分干净、平滑,以免在聚合阶段产生不均一性。
施用的单体层厚度可以为约0.5-30μm。
一般不必使用紫外线聚合引发剂,但是如果单体层厚度超过15μm的话,则最好使用少量所述引发剂,以便加快涂层内部的聚合与成网。
按照本发明,10-15μm厚度已足以得到具有良好的附着力、耐水洗性和希望的无液滴性和消雾性的紫外线聚合涂层。
单体层的聚合和交联是通过暴露在紫外线幅射下而进行的。但是没有必要在缺氧气氛中操作。对于紫外线下长时间暴露的情况,则最好在氮气氛中操作,以免氧气抑制聚合和交联。
显然,聚合速率因而在紫外线下暴露的时间可以在很宽的范围内变化。这取决于多种因素,例如所用单体的种类、所用紫外线灯的功率和类型、单体涂层的厚度及其与灯之间的距离、单体混合物的粘度、载体温度等。
根据本发明,在无紫外线引发剂的情况下操作时,可以根据紫外线灯的功率而采用几秒钟到大约15分钟的很短的幅射时间。最好使用大功率紫外线灯。
为了证实处理所赋予的无液滴性和消雾性的有效程度,对按照本发明方法涂覆的PMMA片材试样和对比片材试样进行了试验。
为了进行试验,使用了50℃的热水浴,在热水浴上方倾斜18-23°放置涂覆的片材,涂覆的表面与蒸汽接触,与对比的未涂覆试样并排放置。
在进行消雾性评估时,是测定涂覆的片材上用眼观察雾消失所需的时间。
将片材置于恒温槽上方保持至少15天,以评估在此期间涂层是否还能保持附着和在此期间无液滴性和消雾性是否能保持不变。
在无液滴试验中,测定凝结的水的量,通过在24小时期间内在每个倾斜片材的下部流动收集测定。
在试验的最后,测定雾状和片材最终透明度。
下面是用于说明的实施例。
实施例1
制备包含1,6-己二醇二丙烯酸酯(HDDA,55%(重量)单体溶液)、丙烯酸二羟乙酯(HEA,25%)、丙烯酸β-羧乙酯(βCEA,12%)和季戊四醇三丙烯酸酯(PETIA,8%)单体溶液,加入胶状二氧化硅(HDK T30-Wacker,1hps)和光引发剂UV(DAROCURE 1173,CIBA-GEIGY)(每100重量份单体溶液加1份),预混合后,将其以10μm的厚度铺在PMMA片材上,然后在中压紫外线灯下固化(灯功率=125W/cm;待固化膜与灯之间的距离是150cm)不超过10秒钟。
将片材在50℃水温的恒温槽上方试验,在外部为室温的情况下,三个月后仍显示出消雾性。消雾性并不立即呈现,通常在恒温槽上方3或4天后片材不雾化或仅轻微雾化。
当恒温槽与室温的温差至少为20℃时,24小时内计量的凝结水约为未涂覆的PMMA片材的3倍。
一个月后,雾度为25%,透明度91%(ASTM D1003),而初始值分别为0.7%和92.1%。黄度指数保持不变(ASTM D1925)。
实施例2
将含有实施例1单体、并加有胶状二氧化硅(HDK T30,每100份单体溶液(phs)加1份)紫外光引发剂(DAROCURE 1173,2phs)和紫外线吸收剂(TINUVIN 1130 CIBA-GEIGY,1phs和TINUVIN 292 CIBA-GEIGY,1phs)的制剂铺展在PMMA片材上,如实施例1那样固化。
尽管涂覆的片材黄度指数稍高,但是消雾性和防雾凝性与实施例1的类似。
将涂覆的片材暴露在QUV/B试验中,暴露3000小时后,未见微裂。在QUV/B下暴露1000小时后,黄度指数与实施例1中相同时间暴露片材的相同。
实施例3
将实施例2的制剂铺展(厚度:10μm)在PMMA片材上,在Philips HPK 125灯(大约25W/cm)下固化,灯与膜之间的距离为10mm,在灯与涂覆的片材之间插一块Pyrex玻璃片(厚度为2mm),在氮气流下固化约5分钟。所和片材具有与前述实施例的片材相同的消雾性和抗凝结性,但其黄度指数有所改善。
实施例4
制备含有单体三缩丙二醇二丙烯酸酯(TPGDA)50%单体溶液、甲基丙烯酸2-羟乙酯(HEMA,20%)、IRR
189(用量:20%)(UCB推出的丙烯酸二聚体混合物)和三羟甲基丙烷三丙烯酸酯(TMPTA,10%),加入2phs(每100重量份溶液的份数)胶状二氧化硅(HDK 740,Wacker)和2phs紫外光引发剂(DAKOCURE 1173),将其铺展在PMMA片材上,象实施例1那样固化。由于TPGDA受大气氧的抑制比HDDA更甚,因此要多加一些光引发剂。涂层的表面性质与实施例1涂层的类似。
实施例5
向含有单体HDDA(55%(重量)单体溶液)、HEMA(25%)、二丙烯酸锌(3%)、βCEA(10%)和二季戊四醇五丙烯酸酯(DPEPA,7%)的溶液中加入胶状二氧化硅(HDKT 30,1phs),将混合物于40℃加热搅拌1小时。
然后,加入紫外光引发剂(IRGACURE 184-CIBA,1phs),于室温搅拌约1小时使其溶于所述溶液中。将如此制得的混合物铺展(厚度:10μ)在PMMA片材上,用与实施例1相同的方法固化。
一天后,我们便可得到初始消雾效果,较之实施例1得到的要快。
实施例6(比较例)
在PMMA片材上涂布15μm的混合物涂层,所述混合物含有55%(重量)甲基丙烯酸甲酯(含有约13份PMMA和87份单体的浆状物形式)、20%(重量)甲基丙烯酸α-羟乙酯(HEMA)、18%(重量)丙烯酸(AA)、6.98%交联剂季戊四醇三丙烯酸酯(PETIA)和0.02%(重量)胶状二氧化硅。使用Philips灯HPK125(大约2.5W/cm),使片材与灯保持20cm的距离,照射10分钟。
将片材置于50℃水温的恒温槽上方进行试验,外部为室温,即使在一个月后仍表现出消雾性。
计量24小时的水凝结量,为未涂覆PMMA片材的三倍。
一个月后,雾度为7%,透明度为89%,而初始值分别为1%和92%。
Claims (9)
1、具有无液滴和消雾性的薄膜、片材和成型件产品,该产品包括由丙烯酸聚合物构成的基材和组成如下的涂层:
a)50-70%(重量)C2-C18脂肪二醇或由1-6个C2-C4氧化烯单元形成的(聚)氧化烯的丙烯酸或甲基丙烯酸酯;
b)10-30%(重量)的下式单体或其低聚物,
式中R是H,CH3;R2是C2-C6羟基烷基或乙氧基基团-(CH2-CH2O)n-H,其中n是一个1-10的整数;
c)10-30%、优选15-20%(重量)丙烯酸或甲基丙烯酸或含有式(Ⅱ)基团的丙烯酸或甲基丙烯酸单体或者优选其二聚体或其衍生物,可选地和优选地是部分盐化的,最好不超过10%,最好是用氨、金属离子或铵盐化的,式(Ⅱ)如下:
式中,R具有上述意义,
d)1-10%(重量)交联剂,它由一种或多种多官能团醇的丙烯酸酯或甲基丙烯酸酯组成,具有至少三个双键,但不包括a)类的成分;
e)每100重量份a+b+c+d,0.01-3重量份、优选0.05-1重量份、更优选0.1-0.5重量份亲水性胶状金属氧化物;
f)每100重量份a+b+c+d,0-0.06重量份紫外线聚合引发剂,
a)、b)、c)、d)之和为100,其中所述涂层用紫外线聚合并交联。
2、权利要求1的产品,其中载体丙烯酸聚合物是丙烯酸酯或甲基丙烯酸酯的均聚物或共聚物。
3、权利要求1的产品,其中载体是聚甲基丙烯酸甲酯。
4、权利要求1的产品,其中单体成分a)是己二醇二丙烯酸酯、三缩丙二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、四甘醇二(甲基)丙烯酸酯。
5、权利要求1的产品,其中单体成分b)是羟乙基或羟丙基丙烯酸酯或甲基丙烯酸酯、(甲基)丙烯酸α-羟乙酯。
6、权利要求1的产品,其中c)中所述的单体是丙烯酸或甲基丙烯酸、β-羧乙基丙烯酸或二丙烯酸锌或铵。
7、权利要求1的产品,其中成网剂是季戊四醇三丙烯酸酯、二羟甲基丙烷三丙烯酸酯、二季戊四醇五丙烯酸酯或季戊四醇四丙烯酸酯。
8、权利要求1的产品,其中胶状金属氧化物是胶状二氧化硅或胶状氢氧化铝。
9、制备权利要求1-8的产品的方法,它具有无液滴性和消雾性,该方法包括在由丙烯酸聚合物构成的载体的表面均匀地涂上一层权利要求1-8的单体组合物,接着将如此涂覆的载体暴露在紫外线幅射下,以便将所述涂覆层聚合并交联。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT93MI002399A IT1266807B1 (it) | 1993-11-10 | 1993-11-10 | Films o lastre antigoccia a base di polimeri acrilici e processo per la loro preparazione |
ITMI93A002399 | 1993-11-10 |
Publications (1)
Publication Number | Publication Date |
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CN1107484A true CN1107484A (zh) | 1995-08-30 |
Family
ID=11367183
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN94113833A Pending CN1107484A (zh) | 1993-11-10 | 1994-11-10 | 由丙烯酸聚合物组成的无液滴薄膜或片材及其制备方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US5547750A (zh) |
EP (1) | EP0652249A1 (zh) |
CN (1) | CN1107484A (zh) |
CA (1) | CA2135089A1 (zh) |
IT (1) | IT1266807B1 (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1269796B (it) * | 1994-05-19 | 1997-04-15 | Marco Rigamonti | Processo per la preparazione di articoli formati antigraffio e antiabrasione,a base di polimeri acrilici |
DE19707185A1 (de) * | 1997-02-22 | 1998-08-27 | Ppg Industries Inc | Kunststoffolie, ihre Verwendung in Verfahren zur Herstellung von Verpackungsbehältern, die so hergestellten Verpackungsbehälter sowie die Verwendung von Lacken zur Applikation über Druckfarbe |
JP3901534B2 (ja) * | 2001-10-11 | 2007-04-04 | 株式会社クレハ | 制電性樹脂組成物 |
CN1321164C (zh) * | 2003-06-20 | 2007-06-13 | 上海小糸车灯有限公司 | 亲水性高分子防雾涂料及其制备方法 |
FR2925912B1 (fr) * | 2007-12-26 | 2010-01-22 | Toray Plastics Europ | Film polyester enroulable comprenant sur au moins l'une de ses faces, un revetement reticule resistant aux rayures, procede d'obtention de ce film polyester |
JP6323108B2 (ja) * | 2014-03-26 | 2018-05-16 | 三菱ケミカル株式会社 | 防曇剤組成物および積層フィルム。 |
JP6334318B2 (ja) * | 2014-08-22 | 2018-05-30 | 三菱ケミカルアグリドリーム株式会社 | 防曇性フィルムおよび積層物 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3400079A1 (de) * | 1984-01-03 | 1985-07-11 | Röhm GmbH, 6100 Darmstadt | Wasserspreitendes kunststoffmaterial, verfahren zu seiner herstellung u. verwendung als verglasungs- und bedachungsmaterial |
FR2623516B1 (fr) * | 1987-11-19 | 1994-04-15 | Saint Gobain Vitrage | Composition pour revetement antibuee, produit revetu de cette composition et procede de preparation de ce produit |
US5104732A (en) * | 1988-12-22 | 1992-04-14 | General Electric Company | Thermoplastic sheet having enhanced water wetting and spreading characteristics |
CA2016740A1 (en) * | 1989-05-26 | 1990-11-26 | Shih-Chung Chen | Anti-fog coating |
IT1255297B (it) * | 1992-05-26 | 1995-10-26 | Marco Rigamonti | Films o lastre antigoccia a base di polimeri acrilici e processo per la loro preparazione |
-
1993
- 1993-11-10 IT IT93MI002399A patent/IT1266807B1/it active IP Right Grant
-
1994
- 1994-11-03 EP EP94117308A patent/EP0652249A1/en not_active Withdrawn
- 1994-11-04 CA CA002135089A patent/CA2135089A1/en not_active Abandoned
- 1994-11-10 CN CN94113833A patent/CN1107484A/zh active Pending
- 1994-11-10 US US08/337,054 patent/US5547750A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ITMI932399A0 (it) | 1993-11-10 |
US5547750A (en) | 1996-08-20 |
CA2135089A1 (en) | 1995-05-11 |
ITMI932399A1 (it) | 1995-05-10 |
EP0652249A1 (en) | 1995-05-10 |
IT1266807B1 (it) | 1997-01-21 |
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