WO1994010221A1 - Peinture en poudre a base d'acryliques - Google Patents

Peinture en poudre a base d'acryliques Download PDF

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Publication number
WO1994010221A1
WO1994010221A1 PCT/NL1993/000212 NL9300212W WO9410221A1 WO 1994010221 A1 WO1994010221 A1 WO 1994010221A1 NL 9300212 W NL9300212 W NL 9300212W WO 9410221 A1 WO9410221 A1 WO 9410221A1
Authority
WO
WIPO (PCT)
Prior art keywords
agent
isocyanate
crosslinking agent
powder paint
glycol
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.)
Ceased
Application number
PCT/NL1993/000212
Other languages
English (en)
Inventor
Szu-Ping Lu
Han Xieng Xiao
Kurt Charles Frisch
Franciscus Maria Witte
Antonius Franciscus Maria Josephus VAN DE PLOEG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Koninklijke DSM NV
Original Assignee
DSM NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DSM NV filed Critical DSM NV
Priority to AU54345/94A priority Critical patent/AU5434594A/en
Publication of WO1994010221A1 publication Critical patent/WO1994010221A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • 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
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/20—Compositions for powder coatings

Definitions

  • the invention relates to a powder paint based on acrylics.
  • Acrylic based powder coatings which are used in practice, are almost exclusively based on epoxy functional acrylic resins cured with long-chain dicarboxylic acids as hardeners.
  • the long aliphatic chain of the crosslinker provides flexibility and impact resistance to the cured film, but still far below the values which are usually obtainable with the other powder coating systems. In most cases the impact resistance of the acrylic powder coatings does not exceed 30 inch- pounds. This is still several times lower compared to the values of polyester and polyurethane based powder coatings.
  • the crosslinker has a melting point higher than 45°C and a molecular weight M n between 100 and 3000, more preferably between 300 and 1500.
  • the mixture of glycols and/or polyglycols contains preferably more than 50% by weight of polytetra- methylene ether glycol as one polyol. More preferably this amount is between 60 and 75% by weight.
  • Suitable other glycols or polyglycols include a great number of diols, triols and polyols, such as for example butanediol, ethanediol, neopentylglycol, 2,2-bis- (l-hydroxy-2-oxyethylphenyl)propane, 1 ⁇ 1-isopropylidene- bis(phenylene-ox )di-2-propanol-2, cyclohexyldimethylol, trimethylolpropane, trimethylolethane, adipate polyols, polycaprolactone glycols and polycarbonate glycols.
  • diols such as for example butanediol, ethanediol, neopentylglycol, 2,2-bis- (l-hydroxy-2-oxyethylphenyl)propane, 1 ⁇ 1-isopropylidene- bis(phenylene-ox
  • the second additional polyglycol is a polyether polyol.
  • a suitable polyether polyol is Voranol 220-530TM (of Dow) .
  • a suitable polytetramethylene ether glycol is
  • Suitable isocyanates include aliphatic (poly)isocyanates such as for example hydrogenated methylene diphenyldiisocyanate (HMDI), isophorone diisocyanate (IPDI), trimer(isocyanate) of isophorone dissocyanate (T1890TM, H ⁇ ls), 1,6-hexamethylene diisocyanate (HDI) and the trimer of 1,6-hexane- diisocyanate (Tolonate HDTTM, Rhone Poulenc), 1,3-bis- (1-isocyanato-l-methylethyl)-benzene (TMXDI; American Cyanamid) or aromatic polyisocyanates, such as for example 2,4 or 2,6-diisocyanatetolueen (TDI) and 4,4 '-di- isocyanatediphenylmethaan.
  • HMDI hydrogenated methylene diphenyldiisocyanate
  • IPDI isophor
  • HMDI is used.
  • the flexible crosslinker can be prepared by first reacting half of the molar equivalents of an isocyanate with the polyglycol mixture and next reacting the remaining isocyanate equivalent with a blocking agent.
  • a blocked isocyanate is an isocyanate which has been reacted with a material which will prevent its reaction at roomtemperature with compounds that conventionally react with isocyanates but will permit that reaction to occur at higher temperature.
  • the blocking agent is a non-volatile agent having a polymerisable double bond and an oxime function.
  • These agents have the general formula (I):
  • R 1 , R 2 , R 3 H or (Ci-Cs.alkyl
  • the amidegroup is steric hindered.
  • the aliphatic group preferably, contains 1-10 carbon atoms.
  • the organic estergroup can be characterized by 0
  • R 6 (C 1 -C 10 )alkyl
  • the agent having a polymerizable double bond and an oxime function is preferably an acrylamide derivative having the formula (II):
  • This suitable blocking agent according to the invention is diacetoneacrylamide oxime (DAAOX).
  • DAAOX diacetoneacrylamide oxime
  • the preparation of DAAOX is disclosed in Macromolecules, Vol. 16, 10, 1983, pages 1561-1563.
  • the use of DAAOX and other blocking agents having a polymerisable double bond and an oxime function is very advantageous, because these blocking agents do not evolve during the cure of a hydroxy-isocyanate powder paint system.
  • the blocking agent can be polymerised during cure of the powder paint, because they consist of a blocking side and a pol merizable double bond.
  • the polymerizable double bond can be polymerized during the cure of the coating by adding a suitable peroxide. Any peroxide having a suitable halflife-time at the curing temperature of the coatings can be used.
  • the peroxide has a halflife-time of less then 10 minutes at the temperature at which the coating is cured.
  • the amount of peroxide can vary between 0.5 and 4 wt.%, preferably between 1 and 2%, based on the weight of the added blocked isocyanate crosslinker.
  • Suitable peroxides include tert.- amyl-peroxybenzoate, tert.-butylperoxybenzoate and tert.- butylperoxy-2-ethylhexyl carbonate.
  • Said non-volatile blocking agents can be obtained from compounds having a ketone or aldehyde group which can be converted into an oxime and having an unsaturated double bond as well.
  • Suitable examples of unsaturated ketones or aldehydegroups include methyl-vinyl-ketone, ethyl-vinyl-ketone, mesityl-oxide, allylacetone, crotonaldehyde, 2-hexanal and citronellal.
  • the blocking agent can be reacted with a (poly)isocyanate in a conventional way.
  • the molar equivalent ratio (poly)isocyanate: blocking agent is substantially 1:1.
  • the main features of the isocyanate-hydroxyl curing reaction are described in the foregoing cited Powder Coatings, Chemistry and Technology at pages 56-58.
  • the use of a non-volatile agent having a polymerizable double bond and an oxime function is not limited to the reaction between a blocked isocyanate and a hydroxyl functional acrylic resin.
  • the hydroxyl functional resin can also be, for example, a polyester or a polyurethane.
  • Suitable volatile blocking agents include for example phenol, cresol, long-aliphatic-chain substituted phenols such as isononylphenol, amides such as ⁇ -caprolactam, active methylene group containing compounds like malonates such as isopropylidene malonate and acetoacetic esters, sodium bisulfite and oximes such as for example methylethylketone oxime and butanone oxime.
  • Suitable hydroxyl-functional acrylate resin include for example resins based on hydroxyethyl
  • the resin may also be b"ased on methacrylic acid and alkyl esters of (meth)acrylic acid such as methyl acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, n-propyl (meth)acrylate, isobutyl (meth)acrylate, ethylhexyl acrylate and/or cyclohexyl (meth)acrylate and vinyl compounds such as styrene.
  • the hydroxylacrylate resins have a hydroxyl number between 40 and 150 mg KOH/g resin and an acid number lower than 20 mg KOH/g resin.
  • the acrylate resins can be prepared by a (co)polymerization, where solvent is fed to a reactor and then heated until the solvent boils. Monomers, and subsequently monomers, initiator and, optionally, mercaptan are added during a period of, for instance, between 2 and 4 hours, after which the temperature is kept at the reflux temperature for, for instance, two hours. The solvent is distilled off by increasing the temperature followed by a vacuum distillation lasting, for instance, one to two hours. Then the product is drained and cooled. Suitable solvents include for example toluene, xylene and butylacetate.
  • Suitable initiators include azo-bis- isobutyronitrile, dibenzoylperoxide and tert.-amyl- peroxy-2-ethyl-hexanoate.
  • the weight ratio polymer:crosslinker is generally between 90:10 and 50:50.
  • the molar equivalent ratio of polymer:crosslinker is between 1:0,8 and 1:1,5. Very suitable ratios are between 1:1 and 1:1,2.
  • customary additives include pigments, fillers, flow aids, stabilizers and catalysts.
  • Suitable pigments include inorganic pigments, for instance titanium oxide, zinc sulphide, iron oxide and chromium oxide, and organic pigments, for instance azo compounds.
  • Suitable fillers include metal oxides, silicates, carbonates and sulphates. The technology and production of powder coatings is described at pages 224-226 of Powder Coatings, Chemistry and Technology, by Tosko Misev (1991; John Wiley and Sons) .
  • Powder coatings according to the present invention can be applied in general industrial and domestic appliances, metal furnitures, architectural applications, automotive topfinishes, corrosion protective coatings and finishes for wood, plastics and paper.
  • US-A-5097010 relates to the preparation of thermally-reversible isocyanate polymer by reacting a labile hydrogen segment with an isocyanate segment.
  • the obtained compositions are useful as hot-melt adhesives, coatings and mouldings and furthermore in injection reaction moulding applications and composite and laminate manufacturing followed by thermal forming and pulltrusion.
  • poly- tetramethylene ether glycol incorporated in a poly- urethane resin results in a flexible network. Applying polytetramethylene ether glycol as the glycol alone will not result in a superior powder coating resin.
  • the mixture of polytetramethylene ether glycol with at least one other glycol or polyglycol produces the desired properties. One glycol is responsible for the flexibility, the other glycol is responsible for the level of the glass transition temperature.
  • the coatings of the present invention are further illustrated by the following experiments and examples. The examples are included for illustrative purposes and should not be considered to limit the present invention.
  • the monomer mixture was fed to the reactor in 2.5 hours.
  • the reflux temperature was maintained in the reactor for another 2.5 hours.
  • a separator vessel was included in the setup, and the solvent was removed by a gradual increase of the temperature and application of a vacuum.
  • a clear product was obtained with a glass transition temperature (Tg, Mettler TA-3000, system 5°C/min) of 46°C and a viscosity ( ) (measured with Emila rheo eter, 165°C) of 350 dPa.s.
  • the glycol blend was made by mixing two glycols in a ratio as mentioned in Table I.
  • a reactor equipped with a stirrer and under a stream of dry nitrogen the respective glycol blend and the appropriate amount of HMDI (see Table I) were charged.
  • Methylethylketone (MEK) was added to reduce the viscosity.
  • a small amount of dibutyl- tindilaurate was added (see Table I) as a catalyst, the reaction mixture was heated to 70°C. It was kept at that temperature until the NCO percentage (as determined by titration) was reduced to half of the initial value.
  • DAAOX was dissolved in MEK and then added into the reaction mixture. The reaction temperature was kept at 70°C until the NCO peak (2270 cm -1 ) disappeared by checking the infrared spectrum of the product.
  • the powder coating ingredients were weighted (in grammes) in the formulations as showed in Table II.
  • the formulations were dissolved is aceton to prepare a solution of 25-30% solids content.
  • the solutions were added into cold water dropwise under vigorous agitation.
  • the precipitates in powder form were then filtered and dried.
  • the dried powders were ground into a very fine particle size. They were sprayed electrostatically on plates and cured as showed in Table II.
  • the examples show that the isocyanate crosslinker according to the invention results in very flexible acrylic powder coatings with good properties.
  • the claimed invention results in a remarkable increase in impact resistance.
  • DAAOX 10 > 193,2 193,2 14 , 75 14 , 75 14 , 75 14,75 14,75 15 DBTL 1X) 0,0123
  • HMDI 1 Hydrogenated Methylene Diphenyl Diisocyanate
  • Voranol 2 Voranol 220-530 (Dow Chemical); polyether polyol
  • Terat 2000 9 Terathane 2000 (Du Pont): polytetramethylene ether glycol with molecular weight 2000
  • Resin Exp. I 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention se rapporte à une peinture en poudre à base d'acryliques. La peinture en poudre thermodurcissable comprend une résine acrylique fonctionnelle hydroxyle et un agent de réticulation isocyanate bloqué à l'aide d'un agent de blocage. L'agent de réticulation isocyanate est un produit d'addition constitué d'un isocyanate et d'un mélange d'un glycol d'éther de polytétraméthylène et d'au moins un glycol supplémentaire, mais différent, choisi dans le groupe comprenant les glycols et les polyglycols.
PCT/NL1993/000212 1992-10-27 1993-10-21 Peinture en poudre a base d'acryliques Ceased WO1994010221A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU54345/94A AU5434594A (en) 1992-10-27 1993-10-21 Acrylic based powder paint

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US96674792A 1992-10-27 1992-10-27
US96674892A 1992-10-27 1992-10-27
US07/966,747 1992-10-27
US07/966,748 1992-10-27

Publications (1)

Publication Number Publication Date
WO1994010221A1 true WO1994010221A1 (fr) 1994-05-11

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Application Number Title Priority Date Filing Date
PCT/NL1993/000212 Ceased WO1994010221A1 (fr) 1992-10-27 1993-10-21 Peinture en poudre a base d'acryliques

Country Status (2)

Country Link
AU (1) AU5434594A (fr)
WO (1) WO1994010221A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0987283A1 (fr) * 1998-09-18 2000-03-22 Dsm N.V. Copolymère en bloc et composition pour liant de peinture en poudre
EP1178080A3 (fr) * 2000-07-19 2003-07-09 Nippon Shokubai Co., Ltd. Composition de résine durcissable utilisée dans un revêtement
EP1559751A2 (fr) 2004-01-28 2005-08-03 Xerox Corporation Procédé de fabrication d'émulsification et d'aggrégation des revêtements en poudre réticulables, revêtements en poudre réticulables et leurs procédés d'utilisation
US7112394B2 (en) 2004-03-01 2006-09-26 Xerox Corporation Thermosetting toner compositions, thermosetting developer compositions and methods for making and using the same
US7247415B2 (en) 2004-08-31 2007-07-24 Xerox Corporation Process for preparing toner particles and toner particles
US7501150B2 (en) 2004-01-28 2009-03-10 Xerox Corporation Emulsion aggregation process for forming powder coating compositions, powder coating compositions and method for using the same
US9469768B1 (en) * 2012-05-30 2016-10-18 Pison Stream Solutions Powder coating composition useful as a finish
CN110167985A (zh) * 2017-01-12 2019-08-23 巴斯夫欧洲公司 聚氨酯的物理性能改进

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2568884A1 (fr) * 1984-08-08 1986-02-14 Stevens Genin Compositions a base de polyurethane et comportant un polymere d'oxime ethylenique, procede de preparation desdites compositions et leurs utilisations
EP0327031A2 (fr) * 1988-02-01 1989-08-09 Asahi Kasei Kogyo Kabushiki Kaisha Composition de prépolymère d'uréthane et système de composition de revêtement de polyuréthane

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2568884A1 (fr) * 1984-08-08 1986-02-14 Stevens Genin Compositions a base de polyurethane et comportant un polymere d'oxime ethylenique, procede de preparation desdites compositions et leurs utilisations
EP0327031A2 (fr) * 1988-02-01 1989-08-09 Asahi Kasei Kogyo Kabushiki Kaisha Composition de prépolymère d'uréthane et système de composition de revêtement de polyuréthane

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0987283A1 (fr) * 1998-09-18 2000-03-22 Dsm N.V. Copolymère en bloc et composition pour liant de peinture en poudre
EP1178080A3 (fr) * 2000-07-19 2003-07-09 Nippon Shokubai Co., Ltd. Composition de résine durcissable utilisée dans un revêtement
US6713551B2 (en) 2000-07-19 2004-03-30 Nippon Shokubai Co., Ltd. Resin composition for coating and coating composition for curing
KR100563420B1 (ko) * 2000-07-19 2006-03-22 가부시키가이샤 닛폰 쇼쿠바이 코팅용 수지 조성물 및 경화용 코팅 조성물
EP1559751A2 (fr) 2004-01-28 2005-08-03 Xerox Corporation Procédé de fabrication d'émulsification et d'aggrégation des revêtements en poudre réticulables, revêtements en poudre réticulables et leurs procédés d'utilisation
US7501150B2 (en) 2004-01-28 2009-03-10 Xerox Corporation Emulsion aggregation process for forming powder coating compositions, powder coating compositions and method for using the same
US7985524B2 (en) 2004-01-28 2011-07-26 Xerox Corporation Emulsion aggregation process for forming curable powder coating compositions, curable powder coating compositions and method for using the same
US7112394B2 (en) 2004-03-01 2006-09-26 Xerox Corporation Thermosetting toner compositions, thermosetting developer compositions and methods for making and using the same
US7247415B2 (en) 2004-08-31 2007-07-24 Xerox Corporation Process for preparing toner particles and toner particles
US9469768B1 (en) * 2012-05-30 2016-10-18 Pison Stream Solutions Powder coating composition useful as a finish
CN110167985A (zh) * 2017-01-12 2019-08-23 巴斯夫欧洲公司 聚氨酯的物理性能改进

Also Published As

Publication number Publication date
AU5434594A (en) 1994-05-24

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