ES2572974T3 - Composiciones de recubrimiento electrodepositables y métodos relacionados - Google Patents

Composiciones de recubrimiento electrodepositables y métodos relacionados Download PDF

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ES2572974T3
ES2572974T3 ES03799399.5T ES03799399T ES2572974T3 ES 2572974 T3 ES2572974 T3 ES 2572974T3 ES 03799399 T ES03799399 T ES 03799399T ES 2572974 T3 ES2572974 T3 ES 2572974T3
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electrodepositable coating
resin
coating composition
catalyst
electrodepositable
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Venkatachalam Eswarakrishnan
Alan J. Kaylo
Gregory J. Mccollum
Ellor James Van Buskirk
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PPG Industries Ohio Inc
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PPG Industries Ohio Inc
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • 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
    • 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
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
    • 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
    • C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
    • 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
    • C08G18/58—Epoxy resins
    • 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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
    • C08G18/643—Reaction products of epoxy resins with at least equivalent amounts of amines
    • 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
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • 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
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • C08G18/8019—Masked aromatic polyisocyanates
    • 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
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy 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
    • 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
    • C09D5/4457—Polyepoxides containing special additives, e.g. pigments, polymeric particles
    • 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
    • C09D5/4488—Cathodic paints
    • C09D5/4492—Cathodic paints containing special additives, e.g. grinding agents

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Molecular Biology (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Una composición de recubrimiento electrodepositable que comprende una fase resinosa dispersa en un medio acuoso, comprendiendo dicha fase resinosa: (a) una resina que contiene un grupo salino catiónico que contiene hidrógeno activo; y (b) un agente de curación de poliisocianato al menos parcialmente bloqueado con un agente de bloqueo que comprende uno o más 1,2- glicoles con lo cual la composición de recubrimiento electrodepositable comprende un catalizador de organoestaño para efectuar la curación entre la resina (a) y el agente de curación (b), en donde dicho catalizador es un compuesto de dialquilestaño que tiene la siguiente estructura (I):**Fórmula** donde R1 y R2 son iguales o diferentes, y cada uno representa independientemente un grupo hidrocarbonado monovalente, en donde la suma de los átomos de carbono de R1 y R2 es mayor de 8, estando presente dicho catalizador en la composición de recubrimiento electrodepositable en una cantidad suficiente para efectuar la curación de la composición electrodepositable a una temperatura a o por debajo de 340 ºF (171,1 ºC).

Description

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puede tener un contenido de hidrógeno activo de entre 1 y 4 miliequivalentes, normalmente de entre 2 y 3 miliequivalentes de hidrógeno activo por gramo de sólido de resina.
El grado de formación del grupo salino catiónico debería ser tal que cuando se mezcle la resina con un medio
5 acuoso y otros ingredientes se forme una dispersión estable de la composición electrodepositable. Por "dispersión estable" se entiende aquella que no sedimenta y que no es fácilmente redispersable si se produce alguna sedimentación. Además, la dispersión debería tener un carácter lo suficientemente catiónico como para que las partículas de resina dispersadas se electrodepositen en un cátodo cuando se establezca un potencial eléctrico entre un ánodo y un cátodo sumergidos en la dispersión acuosa.
Generalmente, la resina catiónica en la composición electrodepositable de la presente invención contiene desde aproximadamente 0,1 hasta 3,0, preferiblemente desde aproximadamente 0,1 hasta 0,7 miliequivalentes de grupo salino catiónico por gramo de sólido de resina. La resina catiónica normalmente no está gelificada, tiene un peso molecular medio en número que varía desde aproximadamente 2.000 hasta aproximadamente 15.000,
15 preferiblemente desde aproximadamente 5.000 hasta aproximadamente 10.000. Por "no gelificada" se entiende que la resina está sustancialmente exenta de reticulación y antes de la formación del grupo salino catiónico, la resina tiene una viscosidad intrínseca mensurable cuando se disuelve en un disolvente adecuado. Por el contrario, una resina gelificada, que tiene esencialmente un peso molecular infinito, tendría una viscosidad intrínseca demasiado alta para ser medida.
La resina que contiene un grupo salino catiónico que contiene hidrógeno activo (a) puede estar presente en la composición electrodepositable de la presente invención en una cantidad que varía desde el 40 hasta el 95 por ciento en peso, normalmente desde el 50 hasta el 75 por ciento en peso basado en el peso de los sólidos de resina totales presentes en la composición.
25 La composición electrodepositable de la presente invención también contiene un agente de curación de poliisocianato al menos parcialmente bloqueado. El agente de curación de poliisocianato puede ser un poliisocianato completamente bloqueado sustancialmente sin ningún grupo isocianato libre, o puede estar parcialmente bloqueado y reaccionar con el esqueleto de la resina según se describe en la Patente de EE.UU. 3.984.299. El poliisocianato puede ser un poliisocianato alifático o aromático, o una mezcla de los dos. Se prefieren los diisocianatos, aunque pueden usarse poliisocianatos superiores en lugar de, o junto con, los diisocianatos.
Algunos ejemplos de diisocianatos alifáticos adecuados son diisocianatos alifáticos de cadena lineal tales como 1,4tetrametilén diisocianato, norbornano diisocianato y 1,6hexametilén diisocianato. También pueden emplearse
35 diisocianatos cicloalifáticos. Algunos ejemplos incluyen isoforona diisocianato y 4,4’metilenbis(ciclohexil isocianato). Algunos ejemplos de diisocianatos aromáticos adecuados son pfenilén diisocianato, difenilmetan4,4’diisocianato y 2,4 o 2,6toluén diisocianato. Algunos ejemplos de poliisocianatos superiores adecuados son trifenilmetan4,4’,4"triisocianato, 1,2,4bencén triisocianato y polimetilén polifenil isocianato y trímeros de 1,6hexametilén diisocianato.
También pueden usarse prepolímeros de isocianato, por ejemplo, los productos de la reacción de poliisocianatos con polioles tales como neopentil glicol y trimetilol propano, o con polioles poliméricos tales como dioles y trioles de policaprolactona (la proporción equivalente de NCO / OH es mayor de uno). Se prefiere una mezcla de difenilmetan4,4’diisocianato y polimetilén polifenil isocianato.
45 Puede usarse cualquier alcohol o poliol adecuado como agente de bloqueo para el poliisocianato de la composición electrodepositable de la presente invención, siempre que el agente se desbloquee a la temperatura de curación, y siempre que no se forme un producto gelificado.
En la presente invención, el agente de bloqueo comprende uno o más 1,2glicoles. En una forma de realización de la presente invención, el agente de bloqueo comprende uno o más 1,2glicoles, normalmente uno o más 1,2glicoles C3 aC6. Por ejemplo, el agente de bloqueo puede seleccionarse de entre al menos uno de 1,2propanodiol, 1,2butanodiol, 1,2pentanodiol y 1,2hexanodiol. Se ha observado que la presencia de dichos agentes de bloqueo facilita la disolución o la dispersión del catalizador de organoestaño en la fase resinosa o en los componentes de la
55 misma.
Otros agentes de bloqueo adecuados incluyen oximas tales como metil etil cetoxima, acetona oxima y ciclohexanona oxima, y lactamas tales como epsiloncaprolactama.
El agente de curación de poliisocianato (b) está presente habitualmente en la composición electrodepositable en una cantidad que varía desde aproximadamente el 5 hasta el 60 por ciento en peso, normalmente desde aproximadamente el 25 hasta el 50 por ciento en peso basado en el peso de los sólidos de resina totales.
Debería entenderse que cualquiera de los catalizadores de organoestaño descritos previamente, que son
65 catalizadores de organoestaño que tienen la anterior estructura (I), los derivados de los mismos y las mezclas de los mismos, pueden ser incorporados en la composición electrodepositable de la presente invención mediante cualquier
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Claims (1)

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ES03799399.5T 2002-10-01 2003-10-01 Composiciones de recubrimiento electrodepositables y métodos relacionados Expired - Lifetime ES2572974T3 (es)

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US41514602P 2002-10-01 2002-10-01
US415146P 2002-10-01
PCT/US2003/031258 WO2004031306A1 (en) 2002-10-01 2003-10-01 Electrodepositable coating compositions and related methods

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US (2) US7497936B2 (es)
EP (1) EP1546271B1 (es)
JP (2) JP2006501357A (es)
KR (1) KR100791701B1 (es)
CN (1) CN100582172C (es)
AU (1) AU2003277236B2 (es)
BR (1) BR0315006B1 (es)
CA (1) CA2500436C (es)
ES (1) ES2572974T3 (es)
HU (1) HUE029209T2 (es)
MX (1) MXPA05003458A (es)
WO (1) WO2004031306A1 (es)

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CA3199506A1 (en) * 2020-12-18 2022-06-23 Corey James DEDOMENIC Thermally conductive and electrically insulating and/or fire-retardant electrodepositable coating compositions
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BR0315006B1 (pt) 2014-06-17
KR20050052522A (ko) 2005-06-02
AU2003277236B2 (en) 2007-02-08
WO2004031306A1 (en) 2004-04-15
CA2500436C (en) 2009-12-15
KR100791701B1 (ko) 2008-01-03
US7497936B2 (en) 2009-03-03
JP2008144181A (ja) 2008-06-26
MXPA05003458A (es) 2005-09-12
CN100582172C (zh) 2010-01-20
US20040069637A1 (en) 2004-04-15
JP2006501357A (ja) 2006-01-12
US8168700B2 (en) 2012-05-01
AU2003277236A1 (en) 2004-04-23
EP1546271B1 (en) 2016-03-30
CA2500436A1 (en) 2004-04-15
HUE029209T2 (en) 2017-02-28
BR0315006A (pt) 2005-08-09
US20090111916A1 (en) 2009-04-30
CN1703469A (zh) 2005-11-30

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