EP2121795A2 - Film-forming material containing phosphorous and methods of producing coating compositions containing phosphorous - Google Patents

Film-forming material containing phosphorous and methods of producing coating compositions containing phosphorous

Info

Publication number
EP2121795A2
EP2121795A2 EP08780364A EP08780364A EP2121795A2 EP 2121795 A2 EP2121795 A2 EP 2121795A2 EP 08780364 A EP08780364 A EP 08780364A EP 08780364 A EP08780364 A EP 08780364A EP 2121795 A2 EP2121795 A2 EP 2121795A2
Authority
EP
European Patent Office
Prior art keywords
group
film
resin
forming material
anhydride
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.)
Withdrawn
Application number
EP08780364A
Other languages
German (de)
English (en)
French (fr)
Inventor
Sergio Gonzalez
Timothy S. December
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.)
BASF Corp
Original Assignee
BASF Corp
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
Priority claimed from US11/672,548 external-priority patent/US7671170B2/en
Priority claimed from US11/672,556 external-priority patent/US7674874B2/en
Application filed by BASF Corp filed Critical BASF Corp
Publication of EP2121795A2 publication Critical patent/EP2121795A2/en
Withdrawn legal-status Critical Current

Links

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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1405—Polycondensates modified by chemical after-treatment with inorganic compounds
    • C08G59/1422—Polycondensates modified by chemical after-treatment with inorganic compounds containing phosphorus
    • 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
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4407—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained by polymerisation reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
    • C09D5/443—Polyepoxides
    • C09D5/4434—Polyepoxides characterised by the nature of the epoxy binder
    • C09D5/4442—Binder characterised by functional groups
    • 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
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
    • C09D5/4465—Polyurethanes

Definitions

  • a grind resin usually includes a film- forming material, with which a pigment paste is made by wetting out pigment, filler, and catalyst, such as a metal catalyst, where the grind resin is blended or mixed with the other materials by milling in, e.g., a sandmill, ball mill, attritor, or other equipment.
  • the pigment paste is combined with the principal resin and, typically, a curing agent.
  • the grind resin and the principal resin can include the same, different, or mixtures of various film-forming materials.
  • the film-forming material is produced by a process comprising reacting a resin having at least one pendent hydroxyl group with a carboxylic anhydride having an ethylenically unsaturated group to form a grafted resin having an ester group, a carboxylic acid group, and an ethylenically unsaturated group, wherein the resin has at least one group reactive with a crosslinker; and reacting the ethylenically unsaturated group of the grafted resin with a phosphate, organophosphate, phosphonate, organophosphonate, phosphinate, or organophosphinate.
  • a method of producing a coating composition includes combining a film-forming material and a crosslinker, wherein the film-forming material comprises a resin having at least one pendent group comprising a covalently bonded phosphorous atom, said phosphorous atom having at least one covalently bonded oxygen atom; and at least one crosslinkable group.
  • Exemplary carboxylic anhydrides include aconitic anhydride, chloromaleic anhydride, citraconic anhydride, ethylmaleic anhydride, itaconic anhydride, maleic anhydride, mellitic anhydride, methoxymaleic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, hexahydrophthalic anhydride, or tetrahydrophthalic anhydride.
  • Acrylic resins can have an equivalent weight (grams resin solid per mol equivalent -OH group) from about 150 to 950, including about 300 to about 600, and further including about 350 to about 550.
  • the number average molecular weight (Mn) can be from about 5,000 to about 10,000 for high solids.
  • a typical acrylic polymer is a hydroxy functional acrylic polyol.
  • an acrylic resin can be used to form an electrocoating composition.
  • a cathodic electrocoating composition may be formed by copolymerizing an amine-functional ethyleneically unsaturated monomer. The amine is salted and dispersed in water.
  • the resin is a polyester resin.
  • Examples of useful polyols include, but are not limited to, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, glycerine, trimethyloipropane, trimethylolethane, pentaerythritol, neopentyl glycol, 2,2,4-trimethyl-1 ,3- pentanediol, 1 ,6-hexanediol, 1 ,4-cyclohexane dimethanol, hydrogenated bisphenol A, and ethoxylated bisphenols.
  • the resin can be a polyurethane resin.
  • Polyurethanes can be formed from two components, where the first includes compounds containing hydroxyl groups, which are at least difunctional for the purposes of the isocyanate-addition reaction.
  • the second component includes at least one polyisocyanate compound.
  • the polyol component must be at least difunctional for the purpose of the polymerization reaction. These compounds generally have an average functionality of about two to eight, preferably about two to four. These compounds generally have a molecular weight of from about 60 to about 10,000, preferably from 400 to about 8,000. However, it is also possible to use low molecular weight compounds having molecular weights below 400. The only requirement is that the compounds used should not be volatile under the heating conditions, if any, used to cure the compositions.
  • Preferred macromonomer compounds containing isocyanate-reactive hydrogen atoms are the known polyester polyols, polyether polyols, polyhydroxy polyacrylates and polycarbonates containing hydroxy! groups.
  • polyhydroxl compounds it is also possible to use polyhydroxy polyacetals, polyhydroxy polyester amides, polythioethers containing terminal hydroxyl groups or sulfhydryl groups or at least difunctional compounds containing amino groups, thiol groups or carboxyl groups.
  • Mixtures of the compounds containing isocyanate-reactive hydrogen atoms may also be used.
  • Other exemplary hydroxyl containing compounds can be found in U.S. Pat. No. 4,439,593 issued on March 27, 1984, which is hereby incorporated by reference.
  • the film-forming material comprises formula (2):
  • film-forming materials include a resin that is capped with an amine, aminoorganophosphate, or aminoorganophosphonate; i.e., where a functional group on the resin is reacted with the amine-containing compound to covalently bond the amine to the resin.
  • the resin can be any resin as described, such as a resin including at least one pendent group comprising a covalently bonded phosphorous atom, the phosphorous atom having at least one covalently bonded oxygen atom, and at least one group reactive with a crosslinker.
  • the film-forming material can include a mixed population of resin molecules.
  • these reactions can result in film-forming material products consisting of fractions of various film-forming materials with different numbers of repeating monomer units. These film-forming materials can result from variations in the rate of propagation and termination events in the reaction used to form the resin and/or by adding various reactants in stages.
  • Film-forming materials can therefore coordinate one or more metals or metal compounds, including metal substrates and/or metal catalysts that improve the cure response of the film-forming material when used in a coating composition.
  • Metals and metal compounds can include those selected from a group consisting of M, MO, M 2 O 3 , M(OH) n , R x MO, and combinations thereof; wherein, n is an integer satisfying the valency of M; R is an alkyl or aromatic group; and x is an integer from 1 to 6.
  • M is selected from the group consisting of Al, Au, Bi, Ce, Cu, Fe, Pb, Sn, Sb, Ti, Y, Zn, and Zr.
  • Exemplary metal catalysts can include dibutyl tin oxide, dibutyl tin dilaurate, zinc oxide, bismuth oxide, tin oxide, yttrium oxide, copper oxide, and combinations thereof.
  • a coating composition contains a crosslinker (i.e., curing agent) for polymerizing a film-forming material comprises an organic compound including at least two functional groups reactive with a film-forming material and at least one pendent group comprising a covalently bonded phosphorous atom, the phosphorous atom having at least one covalently bonded oxygen atom.
  • Functional groups reactive with a film-forming resin include isocyanate, blocked isocyanate, uretdione, epoxide, hydroxyl, carboxyl, ester, ether, carbamate, aminoalkanol, aminoalkylether, amide, or amine groups.
  • a film-forming material is produced by a process comprising reacting a resin having at least one pendent hydroxyl group with a carboxylic anhydride having an ethylenically unsaturated group to form a grafted resin having an ester group, a carboxylic acid group, and an ethylenically unsaturated group, wherein the resin has at least one group reactive with a crosslinker; and reacting the ethylenically unsaturated group of the grafted resin with a phosphate, organophosphate, phosphonate, organophosphonate, phosphinate, or organophosphinate.
  • Such reactions include: epoxide reacted with acid resulting in an ester linkage; epoxide reacted with amine resulting in an amine linkage; hydroxyl reacted with isocyanate resulting in a urethane linkage; hydroxyl reacted with anhydride resulting in an ester linkage; epoxide reacted with hydroxyl resulting in an ether linkage; and other types of linkages generally used in forming coating resins.
  • the resulting film-forming resin contains a crosslinkable group, which can be a group reactive with a crosslinker, a self-condensing group, an addition poiymerizable group, or a group curable with actinic radiation.
  • the film-forming material can comprise a vinyl or acrylic resin, wherein the vinyl resin has at least one pendent group comprising a covalently bonded phosphorous atom, the phosphorous atom having at least one covalently bonded oxygen atom, and at least one group reactive with a crosslinker.
  • the vinyl resin formed by polymerizing a compound having an unsaturated carbon bond and a pendent group comprising a covalently bonded phosphorous atom, the phosphorous atom having at least one covalently bonded oxygen atom, in the resin synthesis.
  • the film-forming materials of the present invention can be the sole film-forming resin, form a population of resins, or can be combined with additional resins.
  • the film-forming materials can be used as a grind resin, principal resin, and/or crosslinker.
  • the same resin can be used in preparing a pigment dispersion and the principal resin, or mixtures of various resins can be used to form a coating composition.
  • the grind resin and the principal resin can be combined in forming a coating composition containing film-forming material(s) according to the present invention.
  • Additional resins can be included with the film-forming materials of the present invention.
  • suitable additional resins include epoxy oligomers and polymers, such as polymers and oligomers of polyglycidyl ethers of polyhydric phenols such as bisphenol A. These can be produced by etherification of a polyphenol with an epihalohydrin or dihalohydrin such as epichlorohydrin or dichlorohydrin in the presence of alkali.
  • Suitable polyhydric phenols include bis-2,2-(4-hydroxyphenyl)propane, bis-1 ,1-(4-hydroxyphenyl)ethane, bis(2-hydroxynaphthyl)methane and the like.
  • these additional resins can be a liquid epoxy that is the reaction product of diglycidyl ether of bisphenol A and bisphenol A.
  • examples include modified upgraded epoxy resins having epoxy equivalent weights of approximately 100 to 1200 or more.
  • Suitable liquid epoxies are GY2600, commercially available from Huntsman, and Epon® 828, commercially available from Hexion Specialty Chemicals, Inc.
  • epoxy-containing compounds can be reacted with hydroxyl- containing compounds, such as bisphenol A, ethoxylated bisphenol A, phenol, polyols, or substituted polyols.
  • the present invention also includes incorporating a metal or a metal compound with the film-forming material to complex the metal or metal compound with the resin.
  • a metal or a metal compound with the film-forming material to complex the metal or metal compound with the resin.
  • one or more electron-rich oxygen atoms such as an oxygen atom bound to a phosphorous atom or an oxygen atom bound to a carbon atom (e.g., an oxygen atom in a carboxylic acid group) may coordinate a metal or metal compound through monodentate or polydentate geometries.
  • the film-forming materials and associated metal(s) can form an associated complex.
  • Metals include the various metals and metal catalysts already mentioned.
  • Suitable examples include 1 ,2-ethylene diisocyanate, 1 ,4- tetramethylene diisocyanate, 1 ,6-hexamethylene diisocyanate, 2,2,4- and 2,4,4-trimethyl-1 ,6-hexamethylene diisocyanate, 1 ,12-dodecane diisocyanate, omega,omega'-diisocyanatodipropyl ether, cyclobutane 1 ,3- diisocyanate, cyclohexane 1 ,3- and 1,4-diisocyanate, 2,2- and 2,6- diisocyanato-1 -methylcyclohexane, 3-isocyanatomethyl-3,5,5- trimethylcyclohexyl isocyanate ("isophorone diisocyanate”), 2,5- and 3,5- bis(isocyanatomethyl)-8-methyI-1 ,4-methano-decahydronaphthalene

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
EP08780364A 2007-02-08 2008-01-07 Film-forming material containing phosphorous and methods of producing coating compositions containing phosphorous Withdrawn EP2121795A2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/672,548 US7671170B2 (en) 2007-02-08 2007-02-08 Film-forming material containing phosphorous
US11/672,556 US7674874B2 (en) 2007-02-08 2007-02-08 Methods of producing coating compositions containing phosphorous
PCT/US2008/050359 WO2008127744A2 (en) 2007-02-08 2008-01-07 Film-forming material containing phosphorous and methods of producing coating compositions containing phosphorous

Publications (1)

Publication Number Publication Date
EP2121795A2 true EP2121795A2 (en) 2009-11-25

Family

ID=39757641

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08780364A Withdrawn EP2121795A2 (en) 2007-02-08 2008-01-07 Film-forming material containing phosphorous and methods of producing coating compositions containing phosphorous

Country Status (5)

Country Link
EP (1) EP2121795A2 (enExample)
JP (1) JP2010518231A (enExample)
CA (1) CA2635857A1 (enExample)
MX (1) MX2008009984A (enExample)
WO (1) WO2008127744A2 (enExample)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102282223B (zh) * 2008-12-29 2015-04-22 巴斯夫涂料有限公司 电涂组合物和代替磷酸盐预处理的方法
WO2010077404A1 (en) * 2008-12-29 2010-07-08 Basf Coatings Gmbh Pyridine group-containing electrocoat resin
US9206284B2 (en) 2008-12-29 2015-12-08 Basf Coatings Gmbh Coating compositions with branched phosphorous-containing resin
US20100163423A1 (en) * 2008-12-29 2010-07-01 Basf Corporation Electrocoat composition and process replacing phosphate pretreatment
EP2384358B1 (en) * 2008-12-29 2017-05-24 BASF Coatings GmbH Electrocoat composition and process replacing phosphate pretreatment
US8192603B2 (en) 2008-12-29 2012-06-05 Basf Coatings Gmbh Electrocoat composition and process replacing phosphate pretreatment
US9382638B2 (en) 2008-12-29 2016-07-05 Basf Corporation Electrocoat composition and process replacing phosphate pretreatment
US8961768B2 (en) 2008-12-29 2015-02-24 Basf Corporation Metal containing integrated electrocoat for better corrosion resistance
US8354471B2 (en) * 2008-12-29 2013-01-15 Basf Coatings Gmbh Acrylic electrocoat composition and process replacing phosphate pretreatment
US8574414B2 (en) 2010-07-14 2013-11-05 Ppg Industries Ohio, Inc Copper prerinse for electrodepositable coating composition comprising yttrium
US20140131212A1 (en) * 2012-11-12 2014-05-15 Ppg Industries Ohio, Inc. Electrodepositable coating compositions containing dimethyl catalyst

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2344584A1 (fr) * 1976-03-19 1977-10-14 Poudres & Explosifs Ste Nale Nouveaux polyethers polyols phosphores et leur procede de preparation
US5086156A (en) * 1989-10-06 1992-02-04 Virginia Tech Intellectual Properties, Inc. Novel phosphorus containing epoxy networks based on trihydrocarbyl phosphine oxides having active substituents
WO2001042253A2 (en) * 1999-12-13 2001-06-14 The Dow Chemical Company Phosphorus element-containing crosslinking agents and flame retardant phosphorus element-containing epoxy resin compositions prepared therewith

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008127744A3 *

Also Published As

Publication number Publication date
CA2635857A1 (en) 2008-08-08
JP2010518231A (ja) 2010-05-27
MX2008009984A (es) 2009-02-27
WO2008127744A3 (en) 2009-05-22
WO2008127744A2 (en) 2008-10-23

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