TW522165B - Aqueous (meth)acrylate copolymers and their use as coating compositions - Google Patents
Aqueous (meth)acrylate copolymers and their use as coating compositions Download PDFInfo
- Publication number
- TW522165B TW522165B TW088101562A TW88101562A TW522165B TW 522165 B TW522165 B TW 522165B TW 088101562 A TW088101562 A TW 088101562A TW 88101562 A TW88101562 A TW 88101562A TW 522165 B TW522165 B TW 522165B
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- Prior art keywords
- copolymer
- weight
- acid
- monomers
- macromonomer
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 34
- 239000008199 coating composition Substances 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 239000002253 acid Substances 0.000 claims abstract description 24
- 229920001400 block copolymer Polymers 0.000 claims abstract description 14
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- 239000003431 cross linking reagent Substances 0.000 claims abstract 3
- -1 fluorenyl acrylate Chemical compound 0.000 claims description 30
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000012986 chain transfer agent Substances 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- IHFPPXNDWUTVAZ-UHFFFAOYSA-N C(C(=C)C)(=O)OCC.C(CCC)N(CCCC)CCCC Chemical compound C(C(=C)C)(=O)OCC.C(CCC)N(CCCC)CCCC IHFPPXNDWUTVAZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 31
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 description 35
- 239000011248 coating agent Substances 0.000 description 25
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 13
- 239000000049 pigment Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000004381 surface treatment Methods 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 239000012972 dimethylethanolamine Substances 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- 238000009500 colour coating Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
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- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- APAUNQLFVGBQQW-UHFFFAOYSA-N (1,2,2-trimethylcyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCCCC1(C)C APAUNQLFVGBQQW-UHFFFAOYSA-N 0.000 description 1
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- ZKEUVTROUPQVTM-UHFFFAOYSA-N 1-pentylperoxypentane Chemical compound CCCCCOOCCCCC ZKEUVTROUPQVTM-UHFFFAOYSA-N 0.000 description 1
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- HYJSEQRQFKDEAT-UHFFFAOYSA-N 2-(dimethylamino)ethanol 2-(2-hydroxyethylamino)ethanol Chemical compound CN(C)CCO.OCCNCCO HYJSEQRQFKDEAT-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
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- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-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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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- SYOYTIYFEGZNHN-UHFFFAOYSA-N pentyl ethaneperoxoate Chemical compound CCCCCOOC(C)=O SYOYTIYFEGZNHN-UHFFFAOYSA-N 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
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- 230000000485 pigmenting effect Effects 0.000 description 1
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- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
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- 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
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- G06T11/00—2D [Two Dimensional] image generation
- G06T11/20—Drawing from basic elements, e.g. lines or circles
- G06T11/206—Drawing of charts or graphs
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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
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- 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
- C08F290/061—Polyesters; Polycarbonates
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
- C08F291/06—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to oxygen-containing macromolecules
- C08F291/08—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to oxygen-containing macromolecules on to macromolecules containing hydroxy radicals
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
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- G—PHYSICS
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- G05B—CONTROL OR REGULATING SYSTEMS IN GENERAL; FUNCTIONAL ELEMENTS OF SUCH SYSTEMS; MONITORING OR TESTING ARRANGEMENTS FOR SUCH SYSTEMS OR ELEMENTS
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- G05B19/418—Total factory control, i.e. centrally controlling a plurality of machines, e.g. direct or distributed numerical control [DNC], flexible manufacturing systems [FMS], integrated manufacturing systems [IMS] or computer integrated manufacturing [CIM]
- G05B19/41865—Total factory control, i.e. centrally controlling a plurality of machines, e.g. direct or distributed numerical control [DNC], flexible manufacturing systems [FMS], integrated manufacturing systems [IMS] or computer integrated manufacturing [CIM] characterised by job scheduling, process planning, material flow
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- G—PHYSICS
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- G05B—CONTROL OR REGULATING SYSTEMS IN GENERAL; FUNCTIONAL ELEMENTS OF SUCH SYSTEMS; MONITORING OR TESTING ARRANGEMENTS FOR SUCH SYSTEMS OR ELEMENTS
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- G05B2219/30—Nc systems
- G05B2219/32—Operator till task planning
- G05B2219/32161—Object oriented control, programming
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P90/00—Enabling technologies with a potential contribution to greenhouse gas [GHG] emissions mitigation
- Y02P90/02—Total factory control, e.g. smart factories, flexible manufacturing systems [FMS] or integrated manufacturing systems [IMS]
Landscapes
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- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
522165 五、發明說明(1) 祖JL申請案之交互參考文獻 本申請案係1 9 9 8年2月1 9曰提供申請之美國臨時申請案 第6 0 / 〇 7 5,1 4 8號之部分連續申請案。 發明之昔景 本發明係關於水性(甲基)丙烯酸酯共聚物之組合物,及 此組合物之製法,及此組合物在具改良性質之含水塗料方 面之用途。更特定而言,本發明係關於羥基值大於2 〇 〇,
酸值低於50,及重量平均分子量低於20, 〇〇〇之(甲基)丙稀 酸酯共聚物組合物,其包含於實質上不含任何酸基之水溶 性巨單體存在下,在水、溶劑或水/溶劑掺合物中直接製 備之叙段或接技共聚物,以致最終得到之乳劑在低黏度下 具有南固體含量。本發明同時包括以此等水性共聚物之級 合物為基礎之塗料組合物。 ' 汽車及 面處理提 引人美感 型汽車鋼 地先以無 其可為電 底塗層表 力。繼而 層。典型 處理則包 質,眾所 卡車接受 供防腐蝕 之表面處 板或基材 機防鏽磷 塗佈底塗 面處理劑 再在底塗 I礎塗層 括金屬薄 週知可在 外表處理有數 之屏障。其次 理,包括高光 具有數層表面 酸鋅或鐵層塗 層或修補底塗 ,以提供較佳 層上加上一層 或顏色塗層包 片’為了保護 著色(含顏料) ,消費者喜愛外表具有 澤及DO I (形象特色)。^ 處理或塗層。該基材典 佈’其上提供一底塗層 層。另外可選擇性地加 =外觀及/或改良之附; 著色之基礎塗層或顏色 含顏料,其若為金屬表 及保持汽車外表美感之 之基礎塗層上施加一
522165 五、發明說明(2) 明(不含顏料) 中基礎塗層也 膜共聚物,丙 聯劑反應使其 已被揭示,然 之應用有限。 環境法規之 (VOC)之產物《 性質之水性產 質及可靠度上 知且已經用於 劑等。 之表塗層,因此即使長s ^ 不會受到影響。塗料如^暴路在環境或天候 土竹組合物勺入 、 埽酸系聚合物為直鏈奸 匕3一或多種成 硬化。使用非直鏈形此取而在應用時以交 而目前發現此等聚人^ =物做為塗料組合物 見美國專利第5, 〇1〇, 14〇號'旱表面處理方面 ,然而鮮少開發具含量 品。如上所述’此種表飞/表面處理所需 有高性能。水分散性卺人仏+ 貝在吴感口口 形成水基性塗料組合物、孜*中為已 顏料分散劑、黏著 在製備水性共聚物分散體用 限用於製造接技共聚物中接技 之可離子化基者。大多數此等 在轉化成水性分散體之前先在 曼」既要 之巨單體方面,鈷螯合物只 或主鏈含有有酸或胺等形式 申凊案也教示該接技共聚物 溶劑中製備。 吾等如今發現水性接技或嵌段共聚物可在水、溶劑或水 /溶劑摻合物中,使用實質上不含任何酸基之水溶性巨單 體製備,以製造在低黏度下具有高固體含量之塗料組合 物。含有該共聚物之分散體及溶液顯示與含水二包裝配方 中之聚異氰酸酯具有優良相容性。 該水性接技或嵌段共聚物包含2 0至9 8重量% (而以5 0至8 5 重量%為較佳)水溶性巨單體,其具有低於6 0 0 0之重量平均
522165
分子量(較佳低於2 0 0 0 ),高於3 0 0之羥基值(較佳高於 400 ) ’且包含少於1〇重量%之酸官能性及/或胺官能性不餘 和單體。該共聚物之其餘2-80%(較佳15-50%)包含主鍵(在 接技共聚物實例中)或B嵌段(在嵌段共聚物實施例中)。$ 接技或嵌段共聚物為重量平均分子量低於2 〇,〇 〇 〇 (較佳在" 1 5 0 0與8 0 0 0之間);羥基值至少2 〇 〇,酸值低於5 〇 (較佳 超過5%)之可離子化單體。 該水溶性巨單體較佳使用自由基引發劑,在水或溶劑或 其掺合物中’使用鈷(11)或鈷(ΠΙ)螯合鏈轉移劑而製1 一 備。 發明之詳細說@
該接技或嵌段共聚物之主鏈或B嵌段,相對於侧鏈(或a 嵌段1/具有較低0H值,且可含有聚合之乙烯系不飽和酸 或胺單體或其鹽類。該主鏈或B嵌段可含有聚合之單體, 其較佳為曱基丙烯酸酯類,但可含有至多5〇%之丙烯酸酯 或乙烯系芳私化合物。此等單體,如下文所列,可包含曱 $丙烯酸及丙烯酸之烷酯、甲基丙烯酸及丙烯酸之環脂族 酉曰以及曱基丙烯酸及丙烯酸之芳族酯等。其可含有至多 為共聚物重量之50重量%之含反應性官能基之乙烯系不飽 和非疏水性單體。其他可加入主鏈或β嵌段中之乙烯系單 $ ,例如乙缚系不飽和確酸、亞石黃酸、膦酸或次膦酸及其 曰^ 也可使用例如笨乙烯確酸、丙烯龜胺曱基丙烧石蔷 酸、乙烯膦酸及其酯類等。 ” 在一個實施例中,接技共聚物乳劑包含50至8 5%之聚曱
第7頁 522165 五、發明說明(4) 基丙烯酸2 -羥基乙酯巨單體,以及15至50 %之主鏈(或B嵌 段)單體(主要為聚曱基丙烯酸酯)。甲基丙烯酸酯單體之 例子有甲基丙烯酸烷酯,諸如甲基丙烯酸曱酯、曱基丙烯 酸乙酯、曱基丙烯酸正丁酯、甲基丙烯酸2-乙基己酯、曱 基丙稀酸壬酯、曱基丙稀酸月桂自旨、甲基丙稀酸硬脂酯 等。其他可使用之曱基丙烯酸酯之例子有曱基丙烯酸三甲 基環己酯、曱基丙烯酸異冰片酯及甲基丙烯酸I酯等。 含有羥基官能基之乙烯系不飽和單體,包括丙烯酸羥烷 酯及甲基丙烯酸羥烷酯,其中之烷基具有1至1 2個碳原 子。適合之單體包括丙烯酸2-羥乙酯、丙烯酸2-羥丙酯、_ 丙烯酸4-羥丁酯、甲基丙烯酸2-羥乙酯、曱基丙烯酸2 -羥 丙酯、曱基丙烯酸4-羥丁酯等及其混合物。反應性官能基 也可得自单體之先質,例如聚合物中曱基丙稀酸縮水甘油 酯單元中之環氧基。此等環氧基可在後續縮合反應中以水 或少量酸轉化為羥基,或用氨及/或一級胺以產生羥胺。 其他合適之烯烴系不飽和共單體,其包括:丙烯醯胺及甲 基丙烯醯胺,及其衍生物如烷氧甲基(曱基)丙烯醯胺單 體,例如N-異丁氧甲基曱基丙烯醯胺及N -羥曱基曱基丙烯 醯胺;順丁烯二酸、衣康酸及順丁烯二酸酐及其半酯及二 酯類;乙烯系芳族如苯乙烯及乙烯系甲苯;聚乙二醇之單 ® 丙烯酸酯及單甲基丙烯酸酯;胺基官能性(曱基)丙烯酸 酯,例如曱基丙烯酸二乙基胺乙酯及甲基丙烯酸第三丁胺 -乙酯;縮水甘油基官能性(甲基)丙烯酸酯,例如甲基丙烯 酸縮水甘油酯。亦可採用其他官能性單體如丙稀睛、丙燦
522165 五、發明說明(5) 酸、甲基丙烯酸烯丙酯、乙醯基乙醯氧乙基曱基丙烯酸 _、甲基丙烯醯胺羥乙酸酯甲醚、甲基丙烯酸乙烯尿素乙 酉曰 2丙稀酿胺-2 -甲基丙礦酸、甲基丙稀酸之三烧氧基 石夕烧基丙酯、單環氧酯或單環氧醚與α-石 -不飽和酸之反 應產物,及(甲基)丙烯酸縮水甘油酯與2 2碳原子以下之單 官能酸之反應產物。上述單體也可使用在共聚物之主鏈及 β嵌段中。如果巨單體可溶於水且含有少於1 0 %之酸官能性 單體’則其也可使用於該巨單體中。 為確定所得到之巨單體只有一個終端乙烯系不飽和基 (其將與殘餘單體聚合以形成接技或嵌段共聚物),將該巨 單體用催化性鏈轉移劑聚合。典型地,製備該巨單體方法 之第一步中,係將單體與可與水互溶或在水中分散之惰性 溶劑及録鏈轉移劑摻合,並通常加熱至反應混合物之回流 溫度。在後續步驟中,加入另外之單體及鈷觸媒及一般聚 合反應觸媒,使聚合反應持續至巨單體成長到所需之分子 量。較佳之鈷鏈轉移劑或觸媒如美國專利第4,6 8 0,3 5 2號 及美國專利第4, 722, 984號及W0 8 7/ 0 36 0 5所述。而以五氱 基鈷酸鹽(II或III)、二水貳(硼二氟二曱基乙二肟醯)鈷 酸鹽(II或III)、及二水貳(硼二氟苯基乙二肟醯)鈷酸鹽 (I I或I I I )為最佳。視所用單體之種類,此等鍵轉移劑之 使用濃度為約2至5 0 0 0 ppm。 巨單體最好在溶劑或溶劑摻合物中,使用自由基引發劑 及鈷(I I或I I I )螯合鏈轉移劑而形成(雖然當使用二水貳 (硼二氟二曱基乙二肟醯)鈷酸鹽(II或III)時’其也可在
第9頁 522l65 五、發明說明(6) 水溶液或乳液中形成)。偶氮塑引發劑(單體之〇· 5至5重量 % )可於存在2至5 0 0 0 ppm (基於總單體)鈷(I I )螯合劑及7 0 至140 °C之溫度範圍下,用於巨單體之合成,更佳之偶氮 型引發劑例如有2, 2,-偶氮貳(2, 4一二甲基戊睛)、2, 2’ —偶 氮貳(2 -甲基丙睛)、2, 2,-偶氮貳(2-甲基丁睛)、l1’ —偶 氮(環己睛)及4, 4,-偶氮貳(4 一氰基戊酸)。可用於形成巨 單體共聚物之典型溶劑有芳族類、脂族類、酮類(例如甲 基乙基酮、異丁酮、乙基戊基酮、丙酮)、醇類(例如甲 醇、乙醇、正丁醇、異丙醇)、3旨類(例如乙酸乙醋)’二 醇類(例如乙二醇、丙二醇),醚類例如四氫呋喃、乙二醇_ 單丁醚等,及如上所述之水及其與水溶混性溶劑之混合 物0 此接技或嵌段共聚物可直接在水、溶劑或水/溶劑混合 物中,藉將剩餘單體摻合物在水溶性巨單體存在下共聚合 而形成。
任何前述偶氮型觸媒皆可被使用,也可使用其他合適之 觸媒,例如過氧化物或氫過氧化物。此等觸媒之典型實例 有二(第三丁基)過氧化物、二(異丙基苯)過氧化物、第三 戊基過氧化物、異丙基苯氫過氧化物、過氧二碳酸二(正 丙基)酯、及過氧酯類如過氧乙酸戊酯等。聚合反應通常 於反應混合物之回流溫度持續進行,直到接技或嵌段共聚 物成長到所需之分子量。也可以使用水溶性自由基引發劑 (宜在2 0至9 8 °C之溫度範圍内使用),例如過氧化物諸如過 硫酸銨,或氧化還原引發劑如第三丁基氫過氧化物/抗壞
522165 ^----- 九、發明說明⑺ — 灰酸。當單體與巨單體共聚合時,町使用鈷螯合物以外之 鏈轉移劑,例如硫醇類Γ氫二基乙酪、第三-十二烷基硫 醇、正十二烷基硫醇。此等黏合劑系統,按照一般漆調配 技術與其他適合之成分摻合,以製造含水塗料。本發明之 接技共聚物在含水塗料組合物(例如汽車應用方面所用之 透明塗料或基礎塗料組合物)之製造上可做為成膜載劑、 生成之塗料組合物具有低揮發性有機物含量,較佳最多為 3 · 5 Q榜/加舍。
本發明之水性接技及嵌段共聚物顯示與聚異氰酸酯交聯 劑有顯著之相容性。聚異氰酸酯之例子包括縮二脲、1,6-己二異氰酸酯之環狀三聚體、異佛爾酮二異氰酸酯、
3,5, 5’ -三曱基-ι,6-己二異氰酸酯及其異構物;4, 4, -二 環己基甲烧一異氰酸自旨(拜耳公司供應之” D e s m 〇 d u r W ’’); 甲苯二異氰酸酯;4, 4,—二苯基甲烷二異氰酸酯;及四甲 基伸二甲苯基二異氰酸酯。進一步之例子包括多元醇(例 如三經甲基丙烷)與過量二異氰酸酯之反應產物,以形成 異氰酸醋官能性聚胺基曱酸酯。可選擇性地使用聚異氰酸 S旨官能性聚S旨-胺基曱酸酯或丙烯酸類-胺基曱酸I旨。可選 擇性地使用自甲基丙烯酸2—異氰酸乙酸或(苯,ι_(卜異氰 酸-1-甲基乙基)〜4-(1-甲基乙烯基))(氰特公司供應之商 品"Μ - Τ Μ Iπ )與其他不飽和化合物聚合所衍生之聚異氰酸酯 官能性丙烯酸類。 該異氰酸酯類可用親水基改質以利於納入水中。親水基 之例子包括聚氧化乙烯。而以使用疏水性聚異氰酸酯為
第11頁 五、發明說明(8) 硬化時,^干==發明之水性共聚物,當用聚異氰酸酯 質、硬度:=ΓΓ2—包裝表面處理系統之成膜性 硬化促進觸=1學品與溶劑抗性。 用異氰酸酯% 7本發明之塗料組合物中,如同使 機金屬化合物,較適合者有二式。較佳之觸媒為有 鋅、二丁基錫二乙酸醋、土,:月桂酸醋、辛酸 酮酸鍅,其以有效硬化量使 乙烯丙_酸釩或乙烯丙 〇. 1至2重量%。㈣觸媒非必· /通常為由黏合劑之約 度及/或時間也足以將組合物ς ^在’舉例而言,升高溫 其他成獏黏合劑,例如丙燒。 醋類、聚醚類、聚醯胺類及:::、及酯類、聚胺基甲酸 組合物中。再者,本發明組:::::存在於最後之塗料 之成分,包括顏料、金屬光;=包含各種可選擇性存在 氧化劑、界面活性劑及流動 土真充劑、可塑劑、抗 組合物所產生表面處理之耐=劑。為改良由本發明塗料 紫外光安定劑之組合物,复用^可加入紫外光安定劑或 重量η等安定劑包括紫外用光 上黏合劑⑻ 劑、及特定受阻胺類光安定卜劑先及^劑、渡光劑、消止 其用量約為•合劑重量之〇 卜,可加入抗氧化劑, 1主b重量%。血型有用之紫外 光安定劑包括二苯甲酮類、二眦相牝/、i有用之 外 及其混合物等。紫外光安定=酸醋類、受阻,類 4, 591,533號所揭示。該組合物也疋列子如吴國專利第 如流動控制劑,例如Resifl〇w物;^包括習用配方添加物 uw 聚丙烯酸丁酯)、BYK320
522165 五、發明說明(9) 及325 (高分子 矽石等。當本 上之透明塗層 時,可將少量 美感效果,例 色塗層、單塗 物對各種金屬 鋼、碟處理鋼 異之附著力。 本組合物可 維、反應射出 當本塗料組合 中之典型顏料 不同顏色之氧 土、重晶石、 例如唉卩丫酮、 咔唾類如咔唾 咪唑咐嗣,金 述用於塗料組 與其他相容性 砂研磨、球研 料組合物中。 份摻合。該塗 電喷塗、浸潰
第13頁 量聚丙烯酸酯類);流變拎 組合物被用做加顏料之工^如發煙 ,以提供透明塗層/有色塗色層塗二(基;塗層) 顏料加在此透明塗料中, 面处理 如色暈。本發明組合物也可加^殊顏色或 層、底塗層、或底塗層表面處以做為 或:ί屬基材’例如已上漆之基合 、及猎電沉積包覆有底塗層之鋼有優 用來塗佈塑膠基材,例如 成型之胺基甲酸酿及部分結:曰璃:纖 物被用做基礎塗料時,則可來醯胺等。 包括:金屬氧化物諸如二氧 σ \此組合物 化鐵、碳黑,填充顏料諸二鈇石:化菩辞、 碳酸鹽、石夕酸鹽及各式各樣 ^ ^,鞑 銅酞菁、m偶氮 有J者色顏料 紫、異吲哚滿,、異吲哚嗣、硫、 屬薄片顏料如銘薄片等。顏料‘二以 ^物中之聚合物形成漆漿或顏料分與前 聚合物或分散劑藉一般方法例如言ό丄或 磨、磨碎機研磨或雙滾輪研磨门品/tc*s 、 繼而將此漆漿與該塗料組合物=用力口入塗 料組合物之塗佈可採用一般
、塗刷、流動塗佈等…嘴塗及靜電噴J 522165
五、發明說明(ίο) 為車父佳。本發明板人你可伯a 1在、w σ物可使用常溫硬化(尤其是再處理 時)’也可升溫硬仆。力flFM# 1ΛΛ 。 更化在〇ΕΜ之應用,該組合物可血型妯户 1〇〇至15(^烘烤約15至30分鐘,以形成約qi至3二= ί ί右Γίί合物用做透明塗層時,可施加在有色塗:
At =有色塗層在施加透明塗層之前,須先乾燥至不黏狀 悲且被石更J匕(最好蕪里日各、 "^心速乾燥)。繼而將該有色塗層/透 ^層之表面處理烘烤’以提供乾燥且硬化之表面處理透 高k上係將透明表塗層藉”濕對濕”之方式施加在基礎塗芦 上,亦即將表塗層施加在未經硬化或完全乾燥之基礎塗^ 丨· 上。繼而將此塗佈之基材加熱歷預設之時間,以使基】 透明塗層同時硬化。 以下實施例係說明本發明。所有,,份”及百分比,除非另 有指定,皆係以重量計。所有此處揭示之分子量係藉透膠 層析法測定,而用聚苯乙烯為基準。 ^ 實例 實例1 巨單韙 本實例指出Co (I I)螯合物在合成下列巨單體上之用途。 BF2架橋之Co( 11 ) (1,2 -二苯基~1,二氧亞胺曱烷)(1〇)螯 合物係如ΕΡ0 1 9 9 43 6之實例4 4B所述。混合物ι(如了列2)係 於保持在氮氣下之反應槽中,於回流(± 1 〇 〇 °c )加熱。混 合物2經4小時添加’隨後立即加入混合物3以供洗務。然 後,將此反應混合物於回流再保持3 〇分鐘。在本製程中 溫度保持在回流,約1〇〇 °C。 ^
第14頁 522165 五、發明說明(π) 混合物1 曱基乙基酮 9. 5 Co( I I )螯合物 0.01 曱基丙烯酸2 -羥乙酯 14 混合物2 甲基丙烯酸2 -羥乙酯 56 VAZ0® 52引發劑(杜邦) 0. 56 曱基乙基酮 18.93 混合物3 曱基乙基酮 1 測試結果:固體含量 65. 6 黏度 B (加德納-候德特氏) 酸值 0.8 Μη 990 Mm 1340 « 此巨單體完全溶於水中。 實例2 巨單體 本實例指出Co (I I I)螯合物在合成下列巨單體上之用 途。該螯合物為氣[1,2_二曱基乙稀-1,2 -二酮-二§5酿(二 氟硼酸)](異丙基)鈷I I I水合物。採用實施例1之步驟與百 分比,而有下列改變。 混合物1
第15頁 522165 五、發明說明(12) 16.95 0. 05 14 56 10.45 0. 3 0. 25 2 39. 5% 小於A 6. 4 940 1280 去離子水 Co(III)整合物 曱基丙烯酸2 -羥乙酯 混合物2 曱基丙烯酸2-羥乙酉旨 去離子水 (4, 4’ -偶氮貳)4-氰基戊羧酸 二甲基乙醇胺 混合物3 去離子水 測試結果:固體含量 黏度 pH Μη Mm 此巨單體完全溶於水中。 實例3至fi 共聚物乳劑 此等實例說明本發明,其中低分子量接技共聚物乳劑係 在水/溶劑摻合物中直接製備,而隨後將該溶劑汽提。該 接技共聚物乳劑係在巨單體(其為水溶性且基本上無任何 酸基)存在下形成。混合物1 (如下列)係在反應槽中加熱 流。混合物2與混合物3經4小時同時添加,隨後加 …人° 物4做為洗梅步驟。將此内容物保持在回流丨小時,繼心而口經
第16頁 522165 五、發明說明(13) 2 0分鐘加入混合物5。加入混合物6做為洗務步驟,並將此 反應槽内容物保持在回流歷1小時。然後,加入混合物7, 並將有機揮發物汽提。
第17頁 522165 五、發明說明(14) 實例 3 4 5 6 混合物1 去離子水 10 10 10 10 巨單體(實例1) 65 65 65 65 混合物2 甲基丙烯酸甲酯 甲基丙烯酸丁酯 甲烯酸乙酯 21.7 22.5 21.7 21.7 甲基丙烯酸 丙烯酸 2.8 2.45 2.8 2.8 混合物3 4,4’《{禺氮威-(4-氯 基戊酸) 0.3 0.3 0.3 0.3 二甲基乙醇胺 0.25 0.25 0.25 0.25 去離子水 9.45 9.45 9.45 9.45 混合物4 去離子水 1 1 1 1 混合物5 4,4’-偶氮貳-(4-氰 基戊酸) 0.03 0.03 0.03 0.03 二甲基乙醇胺- 0.025 0.025 0.025 0.025 去離子水 0.945 0.945 0.945 0.945 混合物6 去離子水 1 1 1 1 混合物7 二乙醇胺 二甲基乙醇胺 3.25 2.75 -2.75 '2.75 1 去離子水 3.75 20.85 11.95 4.25 總量 119.5 136.1 127.2 119.5 汽提 19.5 19.5 19.5 19.5 產率 100.0 116.6 107.7 100.0
II1HU 第18頁 522165 五、發明說明(15) 實例 3 4 測試結果 固體含量(%) 70.2 60.0 黏度*(CPS) 12600 7700 pH Μη 8.3 880 8.6 1180 Mm 2200 2600 *用布魯克非爾^ 黏度計在2〇rpn 1測得 5 65.0 12000 8.7 2700 6900 6 69.9 2750 7.6 1770 3200
實例7 嵌段共聚物分散液 在本實例中,一種AB嵌段共聚物之組合物,使用上述步 驟與下列混合物而製備: 混合物1
巨單體(實例1 ) 65 甲基乙基酮 3. 5 混合物2 曱基丙烯酸丁酯 21.7 曱基丙烯酸 2.8 混合物3 VAZO© 67引發劑(杜邦) 0. 3 曱乙酮 3:7 ' 混合物4 曱基乙基_ 1 第19頁 522165
苐20頁 522165 五、發明說明(17) 實例 混合物1 巨單體(實例1) 8 85.7 9 85.7 10 85.7 11 85.7 12 85.7 13 85.7 14 85.7 混合物2 甲基丙烯酸正丁酯 34 34 24 34 33 甲基丙烯酸2-乙基己酯 33 甲基丙烯酸第三丁胺乙 2 2 2 2 3 2 醋 3 甲基丙烯酸二乙胺乙酯 甲基丙烯酸 4 4 4 4 4 4 4 甲基丙烯酸2-羥丙酯 10 混合物3 VAZ〇®64 0.3 0.3 0.3 0.3 0.3 0.3 0.3 甲基乙基酮 3.83 3.83 3.83 3.83 3.83 3.83 3.83 混合物4 甲基乙基酮 0.5 0.5 0.5 0.5 0.5 0.5 0.5 混合物5 VAZO®64 0.1 0.1 0.1 0.1 0.1 0.1 0.1 甲基乙基酮 0.9 0.9 0.9 0.9 0.9 0.9 0.9 混合物6 甲基乙基酮 2 2 2 2 2 2 2 混合物7 二甲基乙醇胺 4 4 4 4 4 參(羥胺基)甲烷 5.44 三乙醇胺 6.69 去離子水 96 143.3 146 144.6 96 146 50 合計 〇〇 〇 勹 187.3 283.3 283.3 〇 〇 〇 283.3 187.3 汽提 ο ο ο Ο 〇 勹 :〇·:> ,ο ο JJ.O 產率 200 154 250 250 200 250 154 ΙΙΙΙΙΙΗΙ 第21頁 522165 五、發明說明(18) 測試結果: 實例 8 9 10 11 12 13 14 固體含量 51.5 40.12 40.7 40 49,3 40.7 64.4 黏度(CPS) 23250 5350 6400 5600 7250 12300 4150 pH 8.6 8 8.7 7.9 8.6 8.8 8.8 數量平均 分子量 1600 1600 1800 1600 1500 1500 2000 重量平均 分子量 3100 2900 5200 2900 2800 3100 4200 比較例1 重覆實例5之步驟,然而該巨單體包含70重量%曱基丙烯 酸2-羥乙酯之曱基乙基酮溶液,且使用增多%之c〇(ii) 螯合物以降低分子量。本步驟結果產生關=81〇〇且 M W = 1 7 3 0 0之隨機排列直鏈形共聚物。此共聚物乳劑具有非 常高之黏度,因而必須稀釋至31 %固體含量(4300 cps)。 該乳劑無法典型二異氰酸-1,6 -己二酯為基礎之交聯劑相 容。 比較例2 使用實例7之步驟’且使用C ο ( I I )螯合劑做為鏈轉移 劑,以製備相同分子量之隨機排列直鏈形共聚物分散液及 其組合物。所產生之共聚物分散液以二甲基乙醇胺中和, 其ΜΝ=196〇且MW=34〇0。此分散液並不专定(會沉降)。 比較例3 製備與實例1 1總體組成相同之直鏈形隨機排列共聚物。 該共聚物之Μ N = 1 140且MW = 3100。此分散液並不安定(相分
第22頁 522165 五、發明說明(19) 一 離)。 呈jLM比較例1 仿巨單體實例1之步驟’然而使用曱基丙稀酸2 —羥丙 酯取代曱基丙烯酸2-羥乙酯。此巨單體為非水溶性,具有 0.3之酸值,550之MN及1200之MW 〇 电較及5 使用比較巨單體1重覆實例7及1 1之步驟。生成之分散液 及乳劑均不安定。 皇例 仿照W095/ 322 29之實例11步驟,製備自身安定之乳膠, ?包575义主鏈及25%巨單體。此共聚物之重量平均分子量 = 17000、羥基值為96及胺值為15。繼而將此乳膠與上述 二例1 1之共聚物分散液,以乳膠/分散液比(以固體重量 计)為1 00/0 (樣品A)、80 /20 (樣品B)與50/ 50 (樣品C)之比 例互相摻合。接著將德仕摩杜爾LS2〇25聚異氰酸酯交 ^拜耳公司),以幾基/異氰酸酯莫耳比為1/;L25之比例加1 :各個摻合物-中。繼而將此混合物用去離子水稀釋至 =特杯噴黏度,再塗佈在鋼板上,於45t硬化45分鐘。碩 之後,測量其硬度、光澤度、透明度及抗水斑社 破報告於下: …果 透明度 失敗 失敗 通過 榻 失敗 通過 遇過
第23頁 硬度 樣本 勃索茲 (秒) 費瑟 (奴普) 光澤度(60) A 160 4.5 70 B 180 7.0 73 C 185 6.0 95
O:\56\56861.ptc 第1頁
Claims (1)
- 522165 育號_…881 OH 562 六、申 够^1續《本 .一種共聚物修正本 __ 包含: (a) 2 0 - 9 8重量%水溶性巨單體,其具有至少3 0 0之羥基 值’低於6000之重量平均分子量’含有少於10重量%之酸 官能性單體,並具有終端不飽和雙鍵,其中該巨單體包含 已在鈷螯合物鏈轉移劑存在下反應之曱基丙烯酸酯單體單 元;及 (b) 2至80%之聚合單體,其選自乙烯系單體、丙烯酸 酯單體、曱基丙烯酸酯單體及其混合物; 其中該共聚物係選自接技共聚物及嵌段共聚物,其具 有低於20,000之重量平均分子量’大於200之經基值及低 於5 0之酸值。 2. 根據申請專利範圍第1項之共聚物 含至少5 0重量%之曱基丙烯酸2 -羥乙酯 3. 根據申請專利範圍第1項之共聚物 含0. 5至2 0重量%之胺基官能性單體。 4. 根據申請專利範圍第4項之共聚物 性單體係曱基丙烯酸第三丁胺乙酯。 5. 根據申請專利範圍第1項之共聚物,其中該共聚物包 含少於7重量%之酸官能性單體,且其中至少1 0 %之該酸基 已用胺中和。 6 . —種塗料組合物,包含: (a) 1 0至9 5 %之共聚物黏合劑,包含: (1 ) 2 0至9 8重量%水溶性巨單體,其具有至少3 0 0之 羥基值,低於6 0 0 0之重量平均分子量,包含少於1 0重量% 其中該巨單體包 其中該共聚物包 其中該胺基官能O:\56\56861.ptc 第25頁 522165 案號 88101562 Λ_Ά 臼 修正 六、申請專利範圍 之酸官能性單體,並具有終端不飽和雙鍵,其中該巨單體 包含已在鈷螯合物鏈轉移劑存在下反應之曱基丙烯酸酯單 體單元;及 (2)2至8 0%之聚合單體,其選自乙烯系單體、丙烯 酸酯單體、曱基丙烯酸酯單體及其混合物; 其中該共聚物係選自接技共聚物及嵌段共聚物,其具有 低於2 0, 0 0 0之重量平均分子量,大於2 0 0之羥基值及低於 5 0之酸值。 (b) 為共聚物黏合劑重量之5至6 0 %之交聯劑;及 (c) 為共聚物黏合劑重量之0至8 5 %之輔助黏合劑。 7.根據申請專利範圍第6項之組合物,其中該交聯劑包 含衍生自二異氰酸酯之聚異氰酸酯,該二異氰酸酯選自脂 族、環脂族及芳族二異氰酸酯。 8 .根據申請專利範圍第7項之組合物,其中該聚異氰酸 酯係從選自1,6 -己二異氰酸酯及異佛爾酮二異氰酸酯之二 異氰酸酯衍生。 «O:\56\56861.ptc 第26頁
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WO1993003081A1 (en) | 1991-07-31 | 1993-02-18 | E.I. Du Pont De Nemours And Company | Coating compositions based on graft polymers |
US5264530A (en) | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
DE4323192A1 (de) * | 1993-07-10 | 1995-01-12 | Basf Ag | Verfahren zur Herstellung von Homo- und Copolymerisaten von Alk-1-enen |
TW287192B (zh) | 1994-01-21 | 1996-10-01 | Ei Du Pont De Nemours Amd Co | |
JP3884065B2 (ja) | 1994-05-19 | 2007-02-21 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | 水系キャリア中で調製される自己安定化ラテックスを含有する塗料 |
US5770646A (en) | 1996-10-29 | 1998-06-23 | E. I. Du Pont De Nemours And Company | Aqueous branched polymer dispersant for hydrophobic materials |
-
1999
- 1999-01-29 US US09/240,082 patent/US6174953B1/en not_active Expired - Lifetime
- 1999-02-02 TW TW088101562A patent/TW522165B/zh not_active IP Right Cessation
- 1999-02-17 NZ NZ505795A patent/NZ505795A/xx not_active IP Right Cessation
- 1999-02-17 IL IL13707499A patent/IL137074A/xx not_active IP Right Cessation
- 1999-02-17 CA CA002319540A patent/CA2319540A1/en not_active Abandoned
- 1999-02-17 BR BR9908134-2A patent/BR9908134A/pt not_active IP Right Cessation
- 1999-02-17 WO PCT/US1999/003317 patent/WO1999042505A1/en not_active Application Discontinuation
- 1999-02-17 KR KR1020007009078A patent/KR20010041044A/ko not_active Application Discontinuation
- 1999-02-17 DE DE69920179T patent/DE69920179T2/de not_active Expired - Lifetime
- 1999-02-17 AU AU26826/99A patent/AU748306B2/en not_active Ceased
- 1999-02-17 JP JP2000532457A patent/JP2002504575A/ja not_active Withdrawn
- 1999-02-17 ES ES99907076T patent/ES2228009T3/es not_active Expired - Lifetime
- 1999-02-17 EP EP99907076A patent/EP1054915B1/en not_active Expired - Lifetime
- 1999-02-17 MX MXPA00008100 patent/MXPA00008100A/es not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
IL137074A (en) | 2005-09-25 |
MX214854B (zh) | 2003-06-20 |
CA2319540A1 (en) | 1999-08-26 |
JP2002504575A (ja) | 2002-02-12 |
NZ505795A (en) | 2003-01-31 |
AU2682699A (en) | 1999-09-06 |
ES2228009T3 (es) | 2005-04-01 |
EP1054915A1 (en) | 2000-11-29 |
KR20010041044A (ko) | 2001-05-15 |
AU748306B2 (en) | 2002-05-30 |
BR9908134A (pt) | 2000-12-05 |
IL137074A0 (en) | 2001-06-14 |
US6174953B1 (en) | 2001-01-16 |
DE69920179T2 (de) | 2005-09-22 |
EP1054915B1 (en) | 2004-09-15 |
WO1999042505A1 (en) | 1999-08-26 |
MXPA00008100A (es) | 2001-04-01 |
DE69920179D1 (de) | 2004-10-21 |
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