WO2001079366A1 - Wässrige primärdispersionen und beschichtungsstoffe, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Wässrige primärdispersionen und beschichtungsstoffe, verfahren zu ihrer herstellung und ihre verwendung Download PDFInfo
- Publication number
- WO2001079366A1 WO2001079366A1 PCT/EP2001/002707 EP0102707W WO0179366A1 WO 2001079366 A1 WO2001079366 A1 WO 2001079366A1 EP 0102707 W EP0102707 W EP 0102707W WO 0179366 A1 WO0179366 A1 WO 0179366A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- monomers
- coating materials
- aqueous
- dispersions
- monomer
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims abstract description 92
- 239000006185 dispersion Substances 0.000 title claims abstract description 87
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- 239000000178 monomer Substances 0.000 claims abstract description 107
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 53
- 239000002245 particle Substances 0.000 claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 48
- 239000007787 solid Substances 0.000 claims abstract description 32
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- 238000000576 coating method Methods 0.000 claims description 102
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- 150000003254 radicals Chemical class 0.000 claims description 22
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- FCXSGAKSWAEXPU-UHFFFAOYSA-N iminocarbamic acid Chemical compound OC(=O)N=N FCXSGAKSWAEXPU-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- SOOARYARZPXNAL-UHFFFAOYSA-N methyl-thiophenol Natural products CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- CHOHXTASGQTYKN-UHFFFAOYSA-N n,n-dimethyl-2-phenylprop-1-en-1-amine Chemical compound CN(C)C=C(C)C1=CC=CC=C1 CHOHXTASGQTYKN-UHFFFAOYSA-N 0.000 description 1
- SKHDXTZKLIHWBC-UHFFFAOYSA-N n-(1-chlorohexan-2-ylidene)hydroxylamine Chemical compound CCCCC(CCl)=NO SKHDXTZKLIHWBC-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XVNKRRXASPPECQ-UHFFFAOYSA-N phenyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1 XVNKRRXASPPECQ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 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
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Chemical class 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Chemical class 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YAQCYZLLBMLGOB-UHFFFAOYSA-N tricyclo[5.2.1.02,6]dec-3-ylmethanol Chemical compound C1CC2C3C(CO)CCC3C1C2 YAQCYZLLBMLGOB-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Chemical class 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
-
- 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
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
Definitions
- the present invention relates to new aqueous polymer dispersions and coating materials which are dispersed and / or emulsified, solid and / or liquid
- Micro and mini emulsions are dispersions of water, an oil phase and a 20 or more surface-active substances that have droplet sizes from 'to SO nm (microemulsions) or from SO to S00 nm.Microemulsions are considered thermodynamically stable, whereas the mini emulsions are considered metastable (see Emulsion Polyme ⁇ zation and Emulsion Polymers, editors PA Lovell and Mohamed S El-Aassei, John Wiley and Sons, Chichester 2S New York, Weinheim, 1 997, pages 700 and following, Mohamed S El-Aasser, Advances in Emulsion Polvme ⁇ zation and Latex Technology, 30 1 'Annual Short Couise Volume 3, June 7- 1 1 1999, Emulsion Polymers Institute, Lehigh University, Bethlehem, Pennsylvania, USA) Both types of dispersions are widely used in technology, for example in cleaners, cosmetics or Personal care products, however, they can also be used for polymerisation reactions instead of the usual macroemulsions in which
- aqueous polymer dispersions with the aid of radical mini-emulsion polymerization is known, for example, from international patent application WO 98/02466 or German patents DE 196 28 143 A 1 and DE 196 28 142 A 1.
- the monomers can be different in the presence of different low molecular weight , oligomeric or
- polymeric hydrophobic substances which are also referred to as costabilizers, are copolymerized.
- hydrophobic, water-insoluble organic auxiliaries such as plasticizers, improvers of the stickiness of the resulting film, film-forming aids or other unspecified organic additives can be added to the monomer droplets of the mini emulsion
- Aqueous coating materials based on aqueous polymer dispersions which contain 20 solid core-shell particles and which have been prepared by mimemulsion polymerization of monomers in the presence of hydrophobic polymers are known from patent applications EP 0 401 565 A 1, WO 97/49739 or EP 0 755 946 A 1 known
- the known coating materials already have numerous advantageous properties, problems still arise which are associated with an inadequate distribution of the crosslinking agents in the aqueous dispersions. This leads in particular to the fact that a larger amount of crosslinking agents must be used, Unreacted crosslinking agents may then be theoretically necessary Properties of the coatings produced from the coating materials damage
- the radical polymerization used for the production of acrylate copolymers is often very exothermic and difficult to regulate. For the conduct of the reaction, this means that high concentrations of monomers and / or the so-called batch procedure, in which the total amount of monomers in an aqueous medium presented, emulsified and then polymerized out, must be avoided.
- the targeted adjustment of definedi molecular weights, molecular weight distributions and other properties often causes difficulties.
- the property profile of acrylate copolymers is of great importance for their use as binders in coating materials, especially aqueous coating materials, since this can directly influence the application properties profile of the coating materials 5
- aqueous polymer dispersions and coating materials which contain dispersed and / or emulsified, solid and / or liquid polymer particles and / or dispersed solid core-shell particles with a particle diameter of 500 nm included and by radikahsche micro or
- S contain particle diameters ⁇ 500 nm and can be prepared by free-radical micro- or miniemulsion polymerization of an olefinically unsaturated monomer (A) and a diarylethylene (A) in the presence of at least one hydrophobic crosslinking agent for the copolymer resulting from the monomers (A) the monomers (A) and the crosslinking agents
- the object of the present invention is to provide new aqueous polymer dispersions
- I S coating materials containing dispersed and / or emulsified, solid and / or liquid polymer particles and / or dispersed solid core-shell particles
- Coating materials containing finely divided crosslinking agents contain die
- Copolyme ⁇ sate the new aqueous P ⁇ mai dispersions
- Coating materials are included, should have defined molecular weights and, if necessary, can also be produced according to the batch mode without
- novel aqueous polymer dispersions and coating materials comprising dispersed and / or emulsified, solid and / or liquid polymer particles and / or dispersed solid core-shell particles with a particle diameter 500 500 nm, which can be obtained by radical micro- or miniemulsion polymerization of
- At least one olefinically unsaturated monomer (A) can be prepared in the presence of at least one hydrophobic crosslinking agent for the (co) polymer resulting from the monomer or the monomers (A), the monomer or the monomers (A) before the (co ) Polyme ⁇ sat ⁇ on dispersed in an aqueous dispersion of the crosslinking agent or the crosslinking agent, and in
- I S are hereinafter referred to as “inventive powder dispersions or coating materials”.
- the property hydrophilic is understood to mean the constitutional property of a molecule or a functional group, to penetrate into the aqueous phase or then to remain. Accordingly, in the context of the present invention, the constitutional property of a molecule or a functional group is called hydrophobic To understand the group to be exophilic towards water, ie they show a tendency not to penetrate water or to leave the aqueous phase.
- the powder dispersions and coating materials contain dispersed and / or emulsified solid and / or liquid polymer particles and / or dispersed solid core-shell particles.
- the size of the polymer particles or the 5 dispersed core-shell particles results directly from the process according to the invention described below the average particle diameter is below 500 nm. It is preferably from 10 to 500 nm, preferably from 50 to 400 nm and very particularly preferably from 100 to 350 nm.
- novel polymer dispersions and coating materials have an advantageously high solids content, for example of more than 20% by weight. , preferably over 30% by weight, even solids contents of over 40% by weight can be achieved.
- the polymer dispersions and coating materials according to the invention have a low viscosity even with a high solids content
- the core-shell particles to be used according to the invention result from the graft copolymerization of organic solids and the monomers (A) to be used according to the invention described below.
- the organic solids are preferably hydrophobic polymers, as described, for example, in the patents EP 0 401 565 A 1, page 3, lines 5, to page 4, 0 line 50, WO 97/49739, page 4, lines 1 9, to page 5, line 3, or EP 0 755 946 A1, page 3, line 26, to Page 5, line 38, These hydrophobic polymers can also be prepared by the process according to the invention
- the polymer dispersions and coating materials according to the invention can also have 2S a bimodal particle size distribution in which 0.1 to 80% by weight, in particular 1.0 to 50% by weight, of the (co) polymer resulting from the monomers (A) has a particle size , determined with an analytical Ultiazent ⁇ fuge, from 20 to 500 nm, in particular 50 to 300 nm, and 20 to 99.9% by weight, in particular 50 to 99% by weight of the (co) polymer, have a Have particle sizes from 200 to 1,500 nm, in particular 300 to 900 nm, the particle sizes differing by at least 50 nm, in particular by at least 100 nm, very particularly preferably by at least 200 nm.
- lines 5 to 9 are supplemented by Page 6 of the German patent application DE 196 28 142 A1 referenced
- the first starting compound which is essential to the invention for the polymer dispersions or coating materials according to the invention or for the process according to the invention is at least one olefinically unsaturated monomer (A) 0
- At least one monomer (A) which contains reactive functional groups which can undergo crosslinking reactions with the complementary reactive functional groups of the crosslinking agents is preferably used here.
- suitable complementary reactive functional groups to be used according to the invention are summarized in the overview below the variable R stands for an acychic or cychsch ahphatic, an aromatic and / or an aromatic-aliphatic (araliphatic) radical, the variables R and R stand for identical or different aliphatic radicals or are linked together to form an ahphatic or heteroahphatic ring 0
- the selection of the respective complementary groups is based on the one hand on the fact that they do not undergo any undesirable reactions when storing the novel polymer dispersions or coating materials and / or, if appropriate, they do not interfere or inhibit curing with actinic radiation, and on the other hand in which temperature range the crosslinking to be held
- Crosslinking temperatures of from 100 to 180 ° C. are preferably used in the coating materials of the invention.
- Monomers (A) with thio, hydroxyl, alkoxymethylammo, imino, carbamate, allophanate and / or carboxy groups, but especially amino, are preferably used.
- suitable monomers (A) are
- Carbon atoms in the alkyl radical in particular methyl, ethyl, propyl, n-butyl, sec-butyl, tert-butyl, hexyl, ethylhexyl, stearyl and lauryl acrylate or methacrylate, cycloaliphatic (meth) acrylic acid esters, in particular Cyclohexyl, isobornyl, dicyclopentadienyl, octahydro-4,7-methano-1 H-indene-methanol or tert-butylcyclohexyl (meth) acrylate,
- a2) monomers which have at least one hydroxyl, thio, amino, alkoxymethylammo, carbamate, allophanate or imino group, in particular a hydroxyl group.
- Alkylene oxide are available, in particular hydroxyalkyl esters of acrylic acid, methacrylic acid, ethacrylic acid, crotonic acid, maleic acid, fumaric acid or itaconic acid.
- the hydroxyalkyl group contains up to 20 carbon atoms, such as 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl, 4-hydroxybutyl acrylate, methacrylate, ethacrylate, crotonate, maleinate, fumarate or -itaconate, or hydroxycycloalkyl esters such as 1,4-bis (hydroxymethyl) cyclohexane, octahydro-4,7-methano-1 H-indene-dimethanol or methyl propanediol monoacrylate, -monomethacrylate, monoethacrylate, -monocrotonate, -monomaleinate, -monofumarate or - monoitaconate, or reaction products of
- the monomers (a3) are not used as the sole monomers (A) s, but always in connection with other monomers (A) and this only in such small amounts that the monomers (a3) do not polymerize outside the droplets of the miniemulsion
- the branched monocarboxylic acids can be obtained by reacting formic acid or carbon monoxide and water with olefins in the presence of a liquid, strongly acidic catalyst, the olefins can be cracked products of paraffinic hydrocarbons, such as mineral oil fractions, and can be both
- I S contain branched and straight-chain acychic and / or cycloahphatic olefins When such olefins are reacted with formic acid or with carbon monoxide and water, a mixture of carboxylic acids is formed in which the carboxyl groups are predominantly located on a quaternary carbon atom.
- Other olefinic starting materials are, for example, propylene
- the vinyl esters (a4) can, however, also be prepared from the acids in a manner known per se, for example by letting the acid react with acetylene.
- Particularly preferred - because of the good availability - vinyl esters of saturated ahphatic monocarboxylic acids with 9 to 1 1 carbon atoms which are branched at the alpha carbon atom,
- Cych's and / or acych's olefins such as ethylene, propylene, but-1-ene, pent-1-ene, hexylene-1-ene, cyclohexene, cyclopentene, norbornene, butadiene, isoprene, cyclopentadiene and / or dicyclopentadiene
- (Meth) acrylic acid amide such as (meth) acrylic acid amide, N-methyl-, N, N-
- Vinylaromatic hydrocarbons such as styrene, alpha-alkylstyrenes, in particular alpha-methylstyiol, and / or vinyltoluene, vinylbenzoesaui e
- Methyl vinylbenzoic acid (all isomers), N, N-dimethylamino-alpha-methylstyrene (all isomers) and / or p-vinylbenzenesulfonic acid
- radicals R 1 , R 2 , R ' and R each independently of one another represent hydrogen atoms or substituted or unsubstituted alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl
- Arylalkyl or arylcycloalkyl radicals with the proviso that at least two of the variables R, R ", R and R are substituted or unsubstituted aryl, arylalkyl or arylcycloalkyl radicals, in particular substituted or unsubstituted aryl radicals.
- suitable alkyl radicals are methyl, ethyl, Propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, amyl, hexyl or 2-
- Suitable cycloalkyl radicals are cyclobutyl, cyclopentyl or cyclohexyl.
- suitable alkylcycloalkyl radicals are methylene cyclohexane, ethylene cyclohexane or propane-1,3-cyclohexane.
- suitable cycloalkylalkyl radicals are 2-, 3- or 4-methyl, ethyl, or propyl -Butylcyclohex- 1 -yl
- suitable aryl radicals are phenyl,
- Naphthyl or biphenylyl preferably phenyl and naphthyl and especially phenyl.
- suitable alkylaryl radicals are benzyl or ethylene or propane-1,3-benzyl examples
- Cycloalkylaryl radicals are 2-, 3-, or 4-phenylcyclohexyl
- examples of suitable arylalkyl radicals are 2-, 3- or 4-methyl-, -ethyl-, -propyl- or -
- arylcycloalkyl radicals are 2-, 3- or 4-cyclohexylphen-1 -yl.
- the aryl radicals R 1 , R 2 , R ' and / or R are preferably phenyl or naphthyl radicals, in particular phenyl radicals any substituents present in the radicals R, R ⁇ , R 'and / or R are electron-withdrawing or electron-donating atoms or organic radicals, in particular halogen atoms, nit ⁇ l, nitro, partially or completely halogenated alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl , Aryl, alkylaryl, cycloalkylaryl, arylalkyl and ⁇ :
- the monomers (al 0) are not the only ones Monomers used, but always together with other monomers (A), where they regulate the Copolyme ⁇ sation advantageously such that a radical
- Nit ⁇ le such as Acrylnit ⁇ l and / or Methacrylnit ⁇ l
- vinyl compounds in particular vinyl and / or vinylidene dihalides such as vinylchloride, vinylfluid, vinylhide dichloride or vinyldendifluoride, N-ylamides such as vinyl-N-methylformamide, N-vinylcaprolactam, 1-
- Vinylmidazole or N-vinylpy ⁇ olidone vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl thei0 and / or vinyl cyclohexyl thei, and / or vinyl esters such as vinyl acetate,
- allyl compounds in particular allyl methyl and esters such as allyl methyl,
- polysiloxane macromonomers which have a number average molecular weight Mn of 1,000 to 40,000 and an average of 0.5 to 2.5 ethylenically unsaturated double bonds per molecule
- Polysiloxane macromonomers which have a number average molecular weight Mn of 2,000 to 20,000, particularly preferably 2,500 to 10,000 and in particular 3,000 to 7,000 and on average 0.5 to 2.5, preferably 0.5 to 1.5, ethylenically Have unsaturated double bonds per molecule, as described in DE 38 07 571 A1 on pages 5 to 7, DE 37 06 095 A1 in columns 3 to 7, EP 0 358 1 53 B1 on pages 3 to 6 , in US 4,754,014 A1 in columns 5 to 9, in DE 44 21 823 A1 or in international patent application WO 92/2261 5 on page 12, line 1 8, to page 18, line 10 are
- Acryloxysilane-containing vinyl monomers which can be prepared by reacting hydroxy-functional silanes with epichlorohydrin and then reacting the reaction product with (meth) acrylic acid and / or
- the monomers (A) are preferably selected so that (meth) acrylate (co) polymers result, whose profile of properties is determined primarily by the (meth) acrylates described above.
- Comonomers (A) are then preferably vinylaromatic hydrocarbons (a9), especially S styrene used
- the monomers (A) to be used according to the invention are in the presence of at least one water- and / or ollosque, radical-forming initiator
- initiators examples include dialkyl peroxides, such as di-tert-butyl peroxide or dicumyl peroxide, hydroperoxides, such as cumene hydroperoxide or tert-butyl hydroperoxide, peresters, such as tert-butyl perbenzoate, tert-butyl perpivalate, tert-butyl per- 3,5,5-t ⁇ methyl hexanoate or tert-butyl pe 2-ethylhexanoate
- dialkyl peroxides such as di-tert-butyl peroxide or dicumyl peroxide
- hydroperoxides such as cumene hydroperoxide or tert-butyl hydroperoxide
- peresters such as tert-butyl perbenzoate, tert-butyl perpivalate, tert-butyl per- 3,5,5-t ⁇ methyl hexanoate or tert-butyl pe 2-
- azo initiators for example azodinit ⁇ le such as azobisisobutyronit ⁇ l, C-C-cleaving initiators such as benzpinacol silylethei, or a combination of a non-oxidizing initiator with hydrogen peroxide Des can also be used in combinations of the initiators described above
- the monomers (A) are copolymerized in the presence of at least one hydrophobic crosslinking agent.
- the hydrophobic crosslinking agents preferably contain the reactive functional groups described above, the complementary reactive functional groups present in the resulting (co) polymerisates
- crosslinking agents are blocked polyisocyanates, T ⁇ s (alkoxycarbonylam ⁇ no) t ⁇ az ⁇ ne or completely etherified amino resins
- blocking agents for the preparation of the blocked polyisocyanates are the blocking agents known from US Pat. No. 4,444,954
- phenols such as phenol, cresol, xylenol, nitrophenol, chlorophenol,
- lactams such as ⁇ -caprolactam, ⁇ -valerolactam, ⁇ -butyrolactam or ß-propiolactam
- active methylenic compounds such as diethyl malonate, dimethyl malonate, methyl or methyl acetoacetate or acetylacetone
- alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, 5 isobutanol, t-butanol, n-amyl alcohol, t-amyl alcohol, lauryl alcohol,
- Methylolmelamine diacetone alcohol, ethylene chlorohydrin,
- I S v) mercaptans such as butyl mercaptan, hexyl mercaptan, t-butyl mercaptan, t-dodecyl mercaptan, 2-mercaptobenzoth ⁇ azol, thiophenol, methylthiophenol or ethylthiophenol,
- acid amides such as acetoanihd, acetoanisidinamide, acrylamide, methacrylamide, 20 acetic acid amide, stearic acid amide or benzamide,
- vn) imides such as succinimide, phthahmid or maleimide
- amines such as diphenylamine, phenylnaphthylamine, xylidine, N-phenylxyhdin, 25 carbazole, arnim, naphthylamine, butylamine, dibutylamine or
- imidazoles such as imidazole or 2-ethyl imazole
- ureas such as urea, thioham, ethylene urea, ethylene thiourea or 1,3-diphenylurea
- xi) carbamates such as phenyl N-phenylcarbamate or 2-oxazolione
- oximes such as acetone oxime, formal doxime, acetaldoxime, acetoxime, methyl ethyl ketoxime, dnsobutyl ketoxime, diacetyl monoxime, benzophenone oxime or chlorohexanone oxime,
- xiv) salts of the sulfuric acid such as sodium bisulfite or potassium bisulfite
- xv) hydroxamic acid esters such as benzyl methacrylohydroxamate (BMH) or allyl methacrylohydroxamate, or
- suitable organic polyisocyanates to be blocked are in particular the so-called lacquer polyisocyanates with ahphatic, cycloaliphatic, arahphatic and / or aromatically bound isocyanate groups.
- Polyisocyanates with 2 to 5 isocyanate groups per molecule and with viscosities of 100 to 10,000, preferably 100 to 5000, are preferred
- Further examples of suitable polyisocyanates to be blocked are found in "Methods of Organic Chemistry", Houben-Weyl, Volume 14/2, 4th Edition, Georg Thieme Verlag, Stuttgart 1 963, pages 61 to 70, and by W Siefken, Liebigs Annalen der Chemie , Volume 562, pages 75 to 136, for example, the 5 isocyanate group-containing polyurethane prepolymers are suitable, which can be prepared by reacting polyols with an excess of polyisocyanates and which are preferably low-viscosity
- suitable polyisocyanates to be blocked are isocyanurate,
- Polyisocyanates containing 10 biuret, allophanate, iminooxadiazinedione, urethane, urea and / or uretdione groups are obtained, for example, by reacting some of the isocyanate groups with polyols, such as, for example, methyl methyl propane and glycerol, preferably ahphatic or cycloaliphatic,
- uretdione and / or isocyanurate groups and / or allophanate groups containing polyisocyanates are very particularly preferred Base of hexamethylene densocyanate, such as those formed by catalytic ohgome ⁇ sation of hexamethylene dnsocyanate using suitable catalysts, is used.
- the isocyanurate of hexamethylene dnsocyanate blocked with 3,5-dimethylpyrazole is used
- aminoplast resins examples include melamine resins, guanamine resins or urea resins. Any aminoplast resin suitable for clearcoats or a mixture of such aminoplast resins can be used. Rompp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, 1998, page 29, “Amino Resins” and the textbook “Lackadditive” by Johan Bieleman, Wiley-VCH, Weinheim, New York, 1 998, pages 242 ff, or on the book “Paints, Coatings and Solvents", second completely revised edition, Edit D Stoye and W Freitag, Wiley -VCH, Weinheim, New York, 1998, pages 80 ff.
- T ⁇ s (alkoxycarbonylam ⁇ no) t ⁇ az ⁇ ne had the following formula
- T ⁇ s alkoxycarbonylam ⁇ no
- T ⁇ s alkoxycarbonylam ⁇ no
- T ⁇ s alkoxycarbonylam ⁇ no
- t ⁇ az ⁇ ne examples of particularly suitable T ⁇ s (alkoxycarbonylam ⁇ no) t ⁇ az ⁇ ne are described in the patents US 4,939,213 A 1, US 5,084,541 A 1 or EP 0 624 577 A 1.
- the T ⁇ s (methoxy-, T ⁇ s (butoxy- and / or T ⁇ s (2 - ethylhexoxycarbonylam ⁇ no) t ⁇ az ⁇ ne (R methyl, butyl or ethylhexyl) used
- methyl-butyl mixed esters, the butyl-2-ethylhexyl mixed esters and the butyl esters are advantageous. Compared to the pure methyl ester, these have the advantage of better solubility in polymer melts and are also less prone to crystallize out
- the molar ratio of complementary reactive functional groups in (A) is complementary reactive functional groups in the crosslinking agents at 5.0 1.0 to 1.0 5.0, preferably 4.0 1.0 to 1.0 4.0, particularly preferably 3.0 1.0 to 1.0 3.0 0, and in particular 2.0 1 to 1 2.0, there are special advantages if the molar ratio is approximately or exactly 1.0, 0
- the monomer or the monomers (A) is added to an aqueous dispersion of at least one of the crosslinking agents described above before the (co) polymerisation
- the total amount of the crosslinking agents used in each case for example the total amount of the crosslinking agents used in a given coating material according to the invention, or only a part thereof, for example up to 50, preferably 60, preferably 70, particularly preferably 80, very particularly preferably 90 and According to the invention, it is advantageous if the total amount of crosslinking agents is present in the aqueous dispersion
- the content of crosslinking agent in the aqueous dispersion can vary widely and depends primarily on the dispersibility of the crosslinking agent used in each case. It is preferably 1 0 to 80, preferably 1 5 to 70, particularly preferably 20 to 65, very particularly preferably 25 to 60 and in particular 30 to 55% by weight, in each case based on the dispersion
- the continuous phase of the dispersion essentially contains water.
- the aqueous medium can already contain part of the radical initiators described above and / or the emulsifiers, protective colloids, hydrophobic compounds and / or customary and known additives as well as optionally contain other dissolved or dispersed, solid, liquid or gaseous, organic and / or inorganic, low and / or high molecular weight substances, provided that the latter does not negatively influence or even inhibit the (co) polyme ⁇ sat ⁇ on
- minor amount is understood to mean an amount which does not cancel out the aqueous character of the aqueous medium
- the aqueous medium can also be pure or almost pure water, which is advantageous according to the invention.
- the substances listed above, optionally including at least one additional crosslinking agent are only added with or after the addition of the monomers (A) added to the aqueous dispersion of the crosslinking agents
- “almost pure water” is understood to mean water which contains a minor amount, as defined above, of at least one water-miscible organic cosolvent such as N-methylpyrrohdon
- the amount of the monomers (A) which are dispersed in the aqueous dispersion of the crosslinking agents depends primarily on the above-described molar ratio of complementary reactive functional groups in the monomers (A) to complementary reactive functional groups in the crosslinking agents therefore easily calculate the amount of monomers (A) which are preferably used in a given case
- the resulting pre-emulsion of the monomers (A) in the aqueous dispersion of the crosslinking agent is converted into a micro- or mini-emulsion, in particular a mini-emulsion.
- the average particle diameter of the emulsified monomer droplets is less than 500 nm. It is preferably from 0 to 500 nm , preferably 50 to 400 nm and whole particularly preferably 100 to 300 nm
- the particle diameter is the so-called z-average particle diameter, which is determined by means of photon correlation spectroscopy according to the principle of dynamic, quasi-elastic light scattering.
- an S Coulter N4 Plus Particle Analyzer from Coulter Scientific Instruments or a PCS Malvern Zetasizer 1000 are used.
- the measurement is usually carried out on an aqueous emulsion which contains 0.01% by weight of the emulsified monomer droplets.
- the aqueous emulsion furthermore contains the corresponding monomers in dissolved form in the aqueous phase (until saturation). so that the emulsified monomer droplets do not dissolve
- the monomers (A) can be copolymerized in the presence of emulsifiers and / or protective colloids.
- emulsifiers and / or protective colloids examples of suitable emulsifiers and / or protective colloids and the amounts in which they are advantageously used are described in German patent application DE-A-1 96 28 142. Page 3, lines 8 to 48. It is a particular advantage of the method according to the invention that comparatively small amounts of emulsifiers and / or protective colloids 2S have to be used
- hydrophobic can also be used in the (co) polymerisation of the monomers (A) to be used according to the invention Compounds which differ materially from the crosslinking agents are present. These hydrophobic compounds are also known by experts as costabilizers
- hydrophobic compounds are water-insoluble, low-molecular, ohomeric or polymeric substances.
- suitable hydrophobic compounds are esters of 3 to 6 carbon atoms containing alpha, beta-monoolefinically unsaturated carboxylic acids with alcohols with 12 to 30 carbon atoms in the alkyl radical, esters of vinyl and / or allyl alcohol with 12 to
- K 30 carbon atoms in the molecule having alkane monocarbon, sulfonic and / or phosphonic acids, amides of 3 to 6 carbon atoms having alpha, beta-monoolefinically unsaturated carboxylic acids with alkylamines with 12 to 30 carbon atoms in the alkyl radical, macromomers based on olefinically unsaturated compounds with im statistical means at least one,
- I S in particular terminal, olefinically unsaturated group in the molecule, polysiloxane macromonomers with an average of at least one, in particular terminal, olefinically unsaturated group in the molecule, ohgomeric and / or polymeric polymerization, polycondensation and / or polyaddition products, water-insoluble molecular weight rules, in particular
- hydrophobic compounds 20 mercaptans, ahphatic, cycloaliphatic and / or aromatic halogenated and / or non-halogenated hydrocarbons, alkanols and / or alkylamines with at least 12 carbon atoms in the alkyl radical, organosilanes and / or siloxanes, vegetable, animal, semi-synthetic and / or synthetic oils, hydrophobic dyes Further examples of suitable hydrophobic compounds or
- the reactors for the (co) polymer processes are the customary and lo-known Ruhr kettles, Ruhr kettle cascades, tubular reactors, loop reactors or Taylor reactors, as described, for example, in the patents DE 1 071 241 B1, EP 0 498 583 A1 or DE 198 28 742 A1 or in the article by K Kataoka in Chemical Engineering Science, volume 50, number 9, 1 995, pages 1409 to 141 6, into consideration.
- the radical IS (co) polymerization is carried out in Ruhr kettles or Taylor reactors, the Taylor reactors are designed in such a way that the conditions of the Taylor flow are met over the entire length of the reactor, even if the kinematic viscosity of the reaction medium changes greatly, in particular rises, owing to the (co) polymerization
- the (co) polymerization is advantageously carried out at temperatures above room temperature, a temperature range from 30 to 95 ° C., very particularly preferably 50 to 90 ° C., preferably being chosen
- the (co) polymerization can also be carried out under pressure, preferably under 1.5 to 3000 bar, particularly preferably 5 to 1500 and in particular 10 to 1000 bar In individual cases, temperatures higher than 95 "C
- pressure preferably under 1.5 to 3000 bar, particularly preferably 5 to 1500 and in particular 10 to 1000 bar
- temperatures higher than 95 "C The procedures described in German patent application DE-A-196 28 142, page 4, lines 6 to 36 can be used here
- the method according to the invention can be carried out in such a way that the bimodal particle size distribution described above results.
- Methods for producing bimodal particle size distributions are customary and known in the technological field in question. This is preferably described in German patent application DE-A-196 28 142, page 5, Lines 3 1 to 49, described seed method applied
- the polymer dispersions according to the invention are suitable as adhesives, sealants and coating materials or for their production. In particular, they are suitable for the production of coating materials
- Pnmar dispersions according to the invention are added before, while and / or after their preparation, at least one customary and known additive is added in effective amounts. During the preparation of the Pnmar dispersions according to the invention, only those additives are added which do not interfere with or even inhibit the miniemulsion polymerization
- additives mentioned are preferably added after the preparation of the Pnmar dispersions according to the invention.
- suitable additives are pigments such as those found in Rompp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, 1,998, pages 176, "Effect Pigments", pages 380 and 381 "Metalloxid-Gmmer-Pigments” to "Metallpigmente", pages 1 80 and 181 , "Iron blue pigments” to "Iron oxide black", pages 451 to 453, “Pigments” S to "Pigment volume concentration", page 563, “Thioindigo pigments", and page 567, “Titanium dioxide pigments", are described.
- Pigments are used, if the coating materials according to the invention are used as fillers, solid-color topcoats or water-based lacquers, but in particular as water-based lacquers in the context of the so-called wet-on-wet method (cf. for example the European patent EP 10 0 089 497 B1) for the production of color and / or effect multi-layer lacquers become
- IS binders such as thermoplastic and polymeric, thermally hardenable, linear and / or branched and / or block-like, comb-like and / or randomly constructed poly (meth) acrylates or acrylate copolymers, in particular the polyesters described in the patent DE 1 97 36 535 A1, in particular those described in the patents DE 40 09 858 A1 or DE 44 37 535 A1, alkyds, acrylic 0 polyesters, polylactones, polycarbonates, polyethers, epoxy resin-amine adducts, (meth) acrylate diols, partially saponified polyvinyl esters, polyurethanes and acrylic polyurethanes, such as those described in the patents EP 0 521 928 A1, EP 0 522 420 A1, EP 0 522 41 9 A1, EP 0 730 613 A1 or DE 44 37 535 A1, or polyureas
- suitable additives are customary and known paint additives such as organic and inorganic fillers, thermally hardenable reactive thinners, low-boiling and / or high-boiling organic solvents ("long solvents"), UV absorbers, light stabilizers, radical scavengers, thermolabile free radical initiators, Catalysts for the crosslinking, venting agents, slip additives, polymerization inhibitors, defoamers, emulsifiers, wetting agents, adhesion promoters, flow control agents, film-forming aids, rheology-controlling additives or flame retardants.
- suitable coating additives are given in the textbook “coating additives" by Johan Bieleman, Wiley-VCH, Wemheim, New York, 1,998
- the coating materials, adhesives and sealants according to the invention are also to be hardenable with actinic radiation (dual cure), they contain additives which can be hardened with actinic radiation.
- the actimic radiation can be electromagnetic radiation such as near infrared (NIR), visible light, UV - Act light or X-rays or corpuscular radiation such as electron radiation. Examples of suitable additives which can be hardened with actinic radiation are known from German patent DE 197 09 467 C1
- the application of the coating materials, adhesives and sealants according to the invention has no peculiarities, but can be carried out by all customary application methods, such as spraying, knife coating, brushing, pouring, dipping, dripping or rolling, for example, spray application methods are preferably used in the 20 coating materials according to the invention, such as for example compressed air spraying, airless spraying, high rotation, electrostatic spray application (ESTA), possibly combined with hot spray application such as hot air - hot spraying
- spray application methods are preferably used in the 20 coating materials according to the invention, such as for example compressed air spraying, airless spraying, high rotation, electrostatic spray application (ESTA), possibly combined with hot spray application such as hot air - hot spraying
- Suitable substrates are all surfaces to be painted that are not damaged by hardening of the coating materials, adhesives and sealants on them using heat and possibly actinic radiation, e.g. metals, plastics, wood, ceramics, stone , Textile, fiber composites, leather, glass, glass fibers, glass and rock wool, mineral and resin-bound building materials, such as gypsum and cement boards or roof tiles, as well as composites of these materials
- the coating materials according to the invention are used to a high degree for applications in automotive painting, in particular initial automotive painting (OEM), the painting of furniture, doors or windows, the coating of buildings indoors and outdoors or industrial painting, including coil coating, containers Coating and the impregnation or coating of electrical components, under consideration
- OEM initial automotive painting
- it is suitable for painting practically all parts for private or industrial use such as radiators, household appliances, small parts made of metal such as screws and nuts, hubcaps, rims, packaging or electrotechnical components such as motor windings or transformer windings
- primers can be used which are produced in a customary and known manner from electrocoat materials (ETL).
- ETL electrocoat materials
- ATL anodic
- KTL cathodic
- ATL anodic
- KTL cathodic
- a coating treatment in a known manner, such as with a plasma or with flame treatment, or can be provided with a hydro primer
- the hardening of the applied coating materials, adhesives and sealing compounds according to the invention has no special methodological features, but is carried out according to the usual and known thermal methods such as heating in a forced air oven or irradiation with IR lamps, which in the case of Dual Cure can also be supplemented by irradiation with actinic radiation.
- Radiation sources such as high-pressure or high-pressure mercury vapor lamps, which may be doped with lead in order to open a radiation window up to 405 nm, or electron beam sources can be used
- the resulting coatings according to the invention in particular the single- or multi-layer color and / or effect paint systems and clear coat systems according to the invention are simple to produce and have excellent optical properties and a very high chemical and weather resistance. Accordingly, the substrates according to the invention are also the at least one coating according to the invention contain, of a particularly high use value and a particularly long service life, which makes them economically and technically particularly attractive for manufacturers and users
- the adhesive layers and seals according to the invention produced from the adhesives and sealants according to the invention also have excellent application properties, such as high adhesion and complete sealing under extreme climatic conditions, even when there are strong fluctuations in temperature and humidity, so that the substrates bonded and / or sealed with them are also particularly useful economic and technical
- Table 1 gives an overview of the starting materials used for the mini emulsions, the amounts in which they were used, and the z-average particle diameter of the monomer droplets, which can be measured using ⁇ > photon correlation spectroscopy based on the principle of dynamic, quasielastic light scattering using a PCS Malvern Zetasizer 1000 was determined
- the mini-emulsions were transferred to a suitable steel reactor and slowly heated to 70 or 80 U C under partial stirring. The mini-emulsions were stirred at this temperature until the solids content of the resulting P ⁇ mai dispersions according to the invention did not increase for a long time and stable for several weeks S
- Table 1 gives an overview of the polymerization time, the theoretical glass transition temperature Tg dei calculated according to Fox in the Pnmard dispersions according to the invention, of the (co) polyates, the hydroxyl number and the medium particle diameters (measured with a PCS Malvern Zetasizei 1000), the solids content, the screen printing residue and the sediment of the Pnmar dispersions according to the invention
- the P ⁇ braspersions according to the invention were adjusted with the help of the commercially available Collacral® VL S thickener from BASF Aktiengesellschaft to a run-out time in the DIN 4 run-out cup of 24 s, knife-coated onto glass plates with a wet film thickness of 150 ⁇ m and for 30 minutes at 145 ° C., 1 60 ° C and 1 80 ⁇ C baked the Eigebnisse of methyl ethyl ketone tests listed in dei Table 1 show that the resultant tough and clear coatings according to the invention 10 having a particularly high Loseschstabihtat
- Table 1 Material composition and properties of the mini-emulsions according to the invention
- composition (weight point)
Abstract
Description
Claims
Priority Applications (5)
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EP01911758A EP1274805B1 (de) | 2000-04-14 | 2001-03-10 | Verfahren zur herstellung wässriger primärdispersionen und beschichtungsstoffe und deren verwendung |
US10/239,938 US7034074B2 (en) | 2000-04-14 | 2001-03-10 | Aqueous primary dispersions and coating agents, methods for producing them and their use |
AU2001240691A AU2001240691A1 (en) | 2000-04-14 | 2001-03-10 | Aqueous primary dispersions and coating agents, methods for producing them and their use |
JP2001577353A JP2003531240A (ja) | 2000-04-14 | 2001-03-10 | 水性一次分散液および被覆材料、その製法およびその使用 |
DE50111734T DE50111734D1 (de) | 2000-04-14 | 2001-03-10 | Verfahren zur herstellung wässriger primärdispersionen und beschichtungsstoffe und deren verwendung |
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EP (1) | EP1274805B1 (de) |
JP (1) | JP2003531240A (de) |
AT (1) | ATE349503T1 (de) |
AU (1) | AU2001240691A1 (de) |
DE (2) | DE10018601A1 (de) |
ES (1) | ES2278725T3 (de) |
WO (1) | WO2001079366A1 (de) |
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DE102011006674A1 (de) | 2011-04-01 | 2012-10-04 | Bayer Materialscience Aktiengesellschaft | Polymere Nanopartikel und Beschichtungsmittel mit polymeren Nanopartikel |
JP2015193853A (ja) * | 2009-06-08 | 2015-11-05 | 三菱レイヨン株式会社 | 水性被覆材および塗装物 |
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DE10106566A1 (de) | 2001-02-13 | 2002-08-22 | Basf Coatings Ag | Von flüchtigen organischen Stoffen im wesentlichen oder völlig freier wäßriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
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DE10241294A1 (de) * | 2002-09-04 | 2004-03-18 | Basf Ag | Hybriddispersionen aus Polyadditionsprodukten und radikalischen Polymerisaten |
DE10357533A1 (de) | 2003-12-08 | 2005-07-07 | Basf Ag | Verfahren zur Herstellung von Blockcopolymerisaten in Miniemulsion |
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JP6869245B2 (ja) * | 2015-09-23 | 2021-05-12 | ビーエイエスエフ・ソシエタス・エウロパエアBasf Se | 二成分コーティング組成物 |
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2000
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2001
- 2001-03-10 JP JP2001577353A patent/JP2003531240A/ja active Pending
- 2001-03-10 EP EP01911758A patent/EP1274805B1/de not_active Expired - Lifetime
- 2001-03-10 AT AT01911758T patent/ATE349503T1/de not_active IP Right Cessation
- 2001-03-10 ES ES01911758T patent/ES2278725T3/es not_active Expired - Lifetime
- 2001-03-10 WO PCT/EP2001/002707 patent/WO2001079366A1/de active IP Right Grant
- 2001-03-10 DE DE50111734T patent/DE50111734D1/de not_active Expired - Lifetime
- 2001-03-10 US US10/239,938 patent/US7034074B2/en not_active Expired - Fee Related
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JP2004149793A (ja) * | 2002-10-15 | 2004-05-27 | Rohm & Haas Co | 架橋ポリマーナノ粒子の連続生成 |
JP2015193853A (ja) * | 2009-06-08 | 2015-11-05 | 三菱レイヨン株式会社 | 水性被覆材および塗装物 |
DE102011006674A1 (de) | 2011-04-01 | 2012-10-04 | Bayer Materialscience Aktiengesellschaft | Polymere Nanopartikel und Beschichtungsmittel mit polymeren Nanopartikel |
Also Published As
Publication number | Publication date |
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US7034074B2 (en) | 2006-04-25 |
ATE349503T1 (de) | 2007-01-15 |
JP2003531240A (ja) | 2003-10-21 |
EP1274805A1 (de) | 2003-01-15 |
DE50111734D1 (de) | 2007-02-08 |
DE10018601A1 (de) | 2001-10-25 |
EP1274805B1 (de) | 2006-12-27 |
ES2278725T3 (es) | 2007-08-16 |
US20030143414A1 (en) | 2003-07-31 |
AU2001240691A1 (en) | 2001-10-30 |
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