US20030105236A1 - Additives for powder coatings - Google Patents
Additives for powder coatings Download PDFInfo
- Publication number
- US20030105236A1 US20030105236A1 US10/295,795 US29579502A US2003105236A1 US 20030105236 A1 US20030105236 A1 US 20030105236A1 US 29579502 A US29579502 A US 29579502A US 2003105236 A1 US2003105236 A1 US 2003105236A1
- Authority
- US
- United States
- Prior art keywords
- acrylate
- copolymers
- monomers
- meth
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
- C09D5/037—Rheology improving agents, e.g. flow control agents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/47—Levelling agents
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2998—Coated including synthetic resin or polymer
Definitions
- the invention relates to the use of fluoro- and hydroxyl group-containing copolymers as additives for powder coating materials.
- Powder coating materials are a cost-effective and environmentally friendly alternative to liquid paints.
- Crosslinking of the binders to form a protective paint film is generally effected by thermal activation, the coated articles being subjected in an oven to a temperature of customarily from about 160 to about 200° C.
- the powder melts, within a temperature range of customarily from about 80 to about 120° C., and runs out to form a uniform film, which on further heating (from about 110 to about 140° C.) finally cures as a result of the onset of the thermally activated crosslinking reaction.
- complete crosslinking takes between 10 and 30 minutes.
- This object can be achieved in accordance with the invention by adding certain additives to powder coating materials, the additives used being certain fluoro- and hydroxyl group-containing polymers. These additives enhance the levelling of the coating materials and prevent or render less visible the surface defects described above.
- Fluoro- and hydroxyl group-containing copolymers are known from EP-A 0 849 283. They are in the form of nonaqueous dispersions, and are combined with hydroxyl group-containing resins and crosslinkers together to form coating compositions. Their use as additives to powder coating materials is not described.
- Copolymers of hydroxyalkyl acrylates and fluoroalkyl acrylates are also known from WO-A 97/01 114, EP-A 0 620 455, EP-A 0 563 047, and EP-A 0 167 634, and are used for contact lenses. The use of these copolymers as additives to powder coating materials is not described.
- the present invention accordingly provides for the use of copolymers containing fluoro groups and hydroxyl groups as additives in powder coating compositions, said copolymers comprising units of the following monomers:
- a from 5 to 50%; preferably from 7 to 40%; in particular from 9 to 35%;
- [0018] b from 35 to 94.8%; preferably from 40 to 93%; in particular from 45 to 91%;
- c from 0.2 to 15%; preferably from 1 to 12%; in particular from 2 to 10%;
- the present invention further provides for the use of the copolymers of the invention as additives for powder coating materials based on saturated or unsaturated polyesters for the purpose of improving the flow and the quality of the surface of the coatings produced therewith.
- the present invention additionally provides powder coating materials, especially those based on polyesters, which comprise the copolymers of the invention as additives, preferably powder clearcoat materials, and also provides the articles coated therewith.
- the copolymers customarily have a hydroxyl number of from 15 to 250 mg/g, preferably from 20 to 200 mg/g.
- the hydroxyl number called “OHN” below, is defined in accordance with DIN 53 240 as the ratio of that mass m KOH of potassium hydroxide which has exactly the same number of hydroxyl groups as a sample under analysis to the mass m B of that sum (mass of the solid in the sample in the case of solutions or dispersions); its customary unit is “mg/g”.
- the number-average molar mass M n (determined by gel permeation chromatography using polystyrene as standard) of the copolymers is customarily between 1000 and 100 000 g/mol, but preferably between 1500 and 20,000 g/mol.
- the monomers a are preferably hydroxyalkyl esters of olefinically unsaturated carboxylic acids al, the hydroxyalkyl group being linear, branched or cyclic, containing from 2 to 12 carbon atoms, preferably up to 6, and in particular up to 4 carbon atoms, and being preferably selected from the following radicals: 2-hydroxyethyl, 2-hydroxypropyl, 1-hydroxy-2-propyl, 3-hydroxypropyl, 2,2-dimethyl-3-hydroxypropyl, 4-hydroxybutyl, 2-hydroxybutyl, and 6-hydroxyethyl.
- the olefinically unsaturated carboxylic acids are preferably selected from acrylic acid, methacrylic acid, vinyl acetic acid, crotonic acid and isocrotonic acid.
- suitable are bishydroxyalkyl esters of olefinically unsaturated dicarboxylic acids a2 such as the bis(2-hydroxyethyl) esters and bis(hydroxy-propyl)esters of maleic, fumaric, itaconic, citraconic or mesaconic acid, and also monohydroxyalkyl esters of said acids, the remaining carboxyl group being esterified with a linear, branched or cyclic alkanol having from 1 to 20 carbon atoms.
- hydroxyethyl (meth)acrylate 3-hydroxypropyl (meth)acrylate, and the mixtures available commercially, which are referred to as hydroxypropyl (meth)acrylate, of the isomeric adducts of methyloxirane with (meth)acrylic acid, these mixtures containing 2-hydroxypropyl (meth)acrylate and 1-hydroxypropyl 2-(meth)acrylate, in each case alone or in a mixture with one another.
- the monomers b are alkyl esters of monoolefinically unsaturated monocarboxylic acids as stated under al or dialkyl esters of olefinically unsaturated dicarboxylic acids as stated under a2 or mixtures thereof, the alkyl radicals being linear, branched or cyclic and having from 1 to 20 carbon atoms and the carboxylic acids having from 3 to 12 carbon atoms.
- esters of acrylic or methacrylic acid and also of maleic acid with the alcohols methanol, ethanol, n- and iso-propanol, n-, iso-, sec- and tert-butanol, amyl alcohol, n-hexanol, cyclohexanol, and 2-ethylhexanol.
- Particular preference is given to methyl methacrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, dimethyl maleate, and 2-ethylhexyl (meth)acrylate.
- the monomers c are (per)fluoroalkyl esters of the carboxylic acids stated under al, the (per)fluoroalkyl group having from 2 to 20 carbon atoms. Suitable examples include trifluoroethyl (meth)acrylate, hexafluoroisopropyl (meth)acrylate, heptafluorobutyl (meth)acrylate, and perfluorooctyl (meth)acrylate.
- the higher perfluoroalkanols are preferably obtained conventionally by telomerization of tetrafluoroethylene and are then converted into the desired esters C n F 2n+1 —O—CO—R where n ⁇ 2 to 20.
- esters of partly fluorinated alcohols in which context the commercially available mixtures of the 2-perfluoroalkyl ethyl esters of acrylic and methacrylic acid are particularly preferred.
- Further monomers which may be used where appropriate to synthesize the copolymers are those of group d, namely olefinically unsaturated copolymerizable monomers which are free from hydroxyl groups, acid groups, amide groups and fluoro groups, and which do not belong to group b, and those of group e, namely the olefinically unsaturated carboxylic acids stated under a1 and/or the monoalkyl esters of the olefinically unsaturated dicarboxylic acids stated under a2, with linear, branched or cyclic C 1 to C 20 alkyl radicals.
- the monomers d also include vinylaromatic compounds such as styrene, ⁇ -methylstyrene, the isomeric vinyltoluenes and mixtures thereof, chlorostyrene, and also vinyl esters of aliphatic linear, branched or cyclic carboxylic acids having from 1 to 20 carbon atoms, especially vinyl acetate, the vinyl ester of 2-ethylhexanoic acid and the vinyl esters of ⁇ -branched aliphatic carboxylic acids having from 5 to 12 carbon atoms (known as Koch acids or ®Versatic acids), vinyl halides such as vinyl chloride and vinylidene chloride, and nitriles such as acrylonitrile and methacrylo-nitrile.
- vinylaromatic compounds such as styrene, ⁇ -methylstyrene, the isomeric vinyltoluenes and mixtures thereof, chlorostyrene
- Preferred monomers e are acrylic acid, methacrylic acid and mixtures thereof.
- copolymers of the invention are prepared by free-radical copolymerization in a suitable solvent, which is preferably removed by distillation after the preparation.
- the copolymers are used as additives for improving the leveling and the surface in powder coatings. For this purpose they are admixed to the resins, and pigments where appropriate, and other adjuvants and are homogenized with them in conventional manner, by melting and mixing below the crosslinking temperature.
- the mass fraction of these copolymers as additives in the finished powder coating material is customarily from 0.1 to 3%, preferably from 0.2 to 2%, and in particular from 0.3 to 1%.
- the copolymers may also be premixed preferentially with the resins which are used as binders in the powder coating materials or with other resins which are solid at room temperature (20° C.), examples being saturated polyester resins.
- the mixtures of resins and the copolymers may be homogenized together in the melt and comminuted after cooling. The result of such an operation is referred to as a masterbatch.
- the resins are melted with the copolymers, for example, in an extruder and homogenized, and, after cooling, the extrudate is ground to the desired degree of fineness.
- the mass fraction of the copolymer in the mixture of resin and copolymers is customarily between 2 and 30%, preferably between 4 and 20%, and in particular from 6 to 15%.
- a further possibility is to coat the copolymers in liquid form (as a melt or solution) onto finely divided silicon dioxide (silica).
- the resultant powder flows readily and does not tend to stick. This powder is easy to mix into the desired powder coating formulation.
- the powder coating materials modified in this way can be used for coating, for example, metals such as, in particular, steel, aluminum, copper, and also plastics, wood, and natural and artificial stone.
- the acid number is defined in accordance with DIN EN ISO 3682 (DIN 53 402) as the ratio of that mass m KOH of potassium hydroxide which is needed to neutralize a sample under analysis to the mass m B of that sample (mass of the solid in the sample in the case of solutions or dispersions); its customary unit is “mg/g”.
- the additives of the invention were tested in a powder coating material based on a polyesterresin (®Alftalat AN 725 from Solutia Italy S.p.A., saturated polyester having a melting temperature of approximately 80° C. and an acid number of approximately 34 mg/g), using the following formulation: Powder coating P1: Polyester resin 865 g Triglycidyl isocyanurate 70 g Mixture M1 from Example 2 60 g Benzoin 5 g
- the powder clearcoat composition was melted and homogenized in a twin-screw extruder (temperature zones: 80° C./100° C.) with a screw speed of 300/min.
- the extrudate was cooled and ground to give a powder coating material P1 having an average particle size of approximately 40 ⁇ m.
- Powder coatings P2 to P5 and PC were prepared similarly using the mixtures M2 to M5 and MC from Example 2.
- the powder coating materials P1 to P5 and PC were applied using corona guns to steel plates and were cured at 180° C. for 20 minutes. This gave coating films having a thickness of from about 60 to 70 ⁇ m.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/967,987 US7056974B2 (en) | 2001-11-30 | 2004-10-19 | Additives for powder coatings |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT0187401A AT410944B (de) | 2001-11-30 | 2001-11-30 | Additive für pulverlacke |
ATA1874/2001 | 2001-11-30 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/967,987 Division US7056974B2 (en) | 2001-11-30 | 2004-10-19 | Additives for powder coatings |
Publications (1)
Publication Number | Publication Date |
---|---|
US20030105236A1 true US20030105236A1 (en) | 2003-06-05 |
Family
ID=3689193
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/295,795 Abandoned US20030105236A1 (en) | 2001-11-30 | 2002-11-15 | Additives for powder coatings |
US10/967,987 Expired - Lifetime US7056974B2 (en) | 2001-11-30 | 2004-10-19 | Additives for powder coatings |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/967,987 Expired - Lifetime US7056974B2 (en) | 2001-11-30 | 2004-10-19 | Additives for powder coatings |
Country Status (8)
Country | Link |
---|---|
US (2) | US20030105236A1 (de) |
EP (1) | EP1316592B1 (de) |
AT (2) | AT410944B (de) |
CA (1) | CA2413090C (de) |
DE (1) | DE50210741D1 (de) |
DK (1) | DK1316592T3 (de) |
ES (1) | ES2291413T3 (de) |
PT (1) | PT1316592E (de) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1642947A1 (de) * | 2003-07-08 | 2006-04-05 | Kyoeisha Chemical Co., Ltd. | Die oberflächenspannung steuerndes mittel für beschichtungsstoff sowie es enthaltender beschichtungsstoff |
US20060167170A1 (en) * | 2003-07-08 | 2006-07-27 | Kyoeisha Chemical Co., Ltd | Surface tension control agent for coating material and coating material containing same |
US20110040018A1 (en) * | 2008-02-22 | 2011-02-17 | Basf Se | Fluoro levelling agents |
CN103717625A (zh) * | 2011-08-04 | 2014-04-09 | 株式会社Lg化学 | 氟树脂和包含其的光敏树脂组合物 |
CN106279500A (zh) * | 2016-08-24 | 2017-01-04 | 六安科瑞达新型材料有限公司 | 一种高光疏水耐污功能固体丙烯酸树脂 |
CN107099184A (zh) * | 2017-03-24 | 2017-08-29 | 九江市杰克西涂料有限公司 | 一种粉末涂料用固体流平剂及其制备方法 |
CN108250351A (zh) * | 2017-03-12 | 2018-07-06 | 杨记 | 一种耐高温耐黄变含氟环氧树脂的制备方法及应用 |
CN109306201A (zh) * | 2018-09-29 | 2019-02-05 | 黄山华惠科技有限公司 | 一种耐高温、耐水煮型流平剂及其制备粉末涂料的用途 |
US20210024702A1 (en) * | 2018-06-27 | 2021-01-28 | AGC Inc. | Powder dispersion liquid, laminate, film, and impregnated woven fabric |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150051106A (ko) * | 2013-10-30 | 2015-05-11 | 아크조노벨코팅스인터내셔널비.브이. | 분말 코팅 조성물 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5030684A (en) * | 1988-09-28 | 1991-07-09 | Vianova Kunstharz, A.G. | Acrylate copolymers containing hydroxyl and fluorine groups as additives for aqueous anionic paint systems |
US5397669A (en) * | 1992-09-18 | 1995-03-14 | Minnesota Mining And Manufacturing Company | Liquid toners for use with perfluorinated solvents |
US20010005735A1 (en) * | 1998-07-03 | 2001-06-28 | John Ring | Powder coating compositions |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999035195A1 (en) * | 1998-01-06 | 1999-07-15 | H.B. Fuller Company | Powder coating composition |
DE10048258B4 (de) * | 2000-09-29 | 2004-08-19 | Byk-Chemie Gmbh | Verlaufmittel für Oberflächenbeschichtungen |
-
2001
- 2001-11-30 AT AT0187401A patent/AT410944B/de not_active IP Right Cessation
-
2002
- 2002-11-15 US US10/295,795 patent/US20030105236A1/en not_active Abandoned
- 2002-11-21 DE DE50210741T patent/DE50210741D1/de not_active Expired - Lifetime
- 2002-11-21 PT PT02026325T patent/PT1316592E/pt unknown
- 2002-11-21 ES ES02026325T patent/ES2291413T3/es not_active Expired - Lifetime
- 2002-11-21 AT AT02026325T patent/ATE370996T1/de not_active IP Right Cessation
- 2002-11-21 DK DK02026325T patent/DK1316592T3/da active
- 2002-11-21 EP EP02026325A patent/EP1316592B1/de not_active Expired - Lifetime
- 2002-11-28 CA CA002413090A patent/CA2413090C/en not_active Expired - Lifetime
-
2004
- 2004-10-19 US US10/967,987 patent/US7056974B2/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5030684A (en) * | 1988-09-28 | 1991-07-09 | Vianova Kunstharz, A.G. | Acrylate copolymers containing hydroxyl and fluorine groups as additives for aqueous anionic paint systems |
US5397669A (en) * | 1992-09-18 | 1995-03-14 | Minnesota Mining And Manufacturing Company | Liquid toners for use with perfluorinated solvents |
US20010005735A1 (en) * | 1998-07-03 | 2001-06-28 | John Ring | Powder coating compositions |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1642947A1 (de) * | 2003-07-08 | 2006-04-05 | Kyoeisha Chemical Co., Ltd. | Die oberflächenspannung steuerndes mittel für beschichtungsstoff sowie es enthaltender beschichtungsstoff |
EP1642947A4 (de) * | 2003-07-08 | 2006-07-19 | Kyoeisha Chemical Co Ltd | Die oberflächenspannung steuerndes mittel für beschichtungsstoff sowie es enthaltender beschichtungsstoff |
US20060167170A1 (en) * | 2003-07-08 | 2006-07-27 | Kyoeisha Chemical Co., Ltd | Surface tension control agent for coating material and coating material containing same |
US7196133B2 (en) | 2003-07-08 | 2007-03-27 | Kyoeisha Chemical Co., Ltd. | Surface tension control agent for coating material and coating material containing same |
US20110040018A1 (en) * | 2008-02-22 | 2011-02-17 | Basf Se | Fluoro levelling agents |
US8669336B2 (en) | 2008-02-22 | 2014-03-11 | Basf Se | Fluoro levelling agents |
CN103717625A (zh) * | 2011-08-04 | 2014-04-09 | 株式会社Lg化学 | 氟树脂和包含其的光敏树脂组合物 |
US9274423B2 (en) | 2011-08-04 | 2016-03-01 | Lg Chem, Ltd. | Fluorine-based resins and photosensitive resin composition comprising the same |
CN106279500A (zh) * | 2016-08-24 | 2017-01-04 | 六安科瑞达新型材料有限公司 | 一种高光疏水耐污功能固体丙烯酸树脂 |
CN108250351A (zh) * | 2017-03-12 | 2018-07-06 | 杨记 | 一种耐高温耐黄变含氟环氧树脂的制备方法及应用 |
CN107099184A (zh) * | 2017-03-24 | 2017-08-29 | 九江市杰克西涂料有限公司 | 一种粉末涂料用固体流平剂及其制备方法 |
US20210024702A1 (en) * | 2018-06-27 | 2021-01-28 | AGC Inc. | Powder dispersion liquid, laminate, film, and impregnated woven fabric |
CN109306201A (zh) * | 2018-09-29 | 2019-02-05 | 黄山华惠科技有限公司 | 一种耐高温、耐水煮型流平剂及其制备粉末涂料的用途 |
Also Published As
Publication number | Publication date |
---|---|
DK1316592T3 (da) | 2008-01-02 |
US20050053786A1 (en) | 2005-03-10 |
PT1316592E (pt) | 2007-11-20 |
EP1316592A1 (de) | 2003-06-04 |
US7056974B2 (en) | 2006-06-06 |
CA2413090A1 (en) | 2003-05-30 |
ES2291413T3 (es) | 2008-03-01 |
ATA18742001A (de) | 2003-01-15 |
EP1316592B1 (de) | 2007-08-22 |
CA2413090C (en) | 2009-09-08 |
ATE370996T1 (de) | 2007-09-15 |
DE50210741D1 (de) | 2007-10-04 |
AT410944B (de) | 2003-08-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: SOLUTIA AUSTRIA GMBH, AUSTRIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HOBISCH, GERALD;MORRE, PETER;CAVALIERI, ROBERTO;AND OTHERS;REEL/FRAME:013518/0635 Effective date: 20021024 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |