ES2642061T3 - Composiciones de recubrimiento para artículos de envasado y métodos de recubrimiento - Google Patents

Composiciones de recubrimiento para artículos de envasado y métodos de recubrimiento Download PDF

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ES2642061T3
ES2642061T3 ES11769696.3T ES11769696T ES2642061T3 ES 2642061 T3 ES2642061 T3 ES 2642061T3 ES 11769696 T ES11769696 T ES 11769696T ES 2642061 T3 ES2642061 T3 ES 2642061T3
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polymer
formula
coating
parts
polyether
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Richard H. Evans
Jeffrey Niederst
Robert M. O'brien
Benoit Prouvost
Kevin Romagnoli
Grant Schutte
Paul Stenson
Tom Van Kuren
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Sherwin Williams Co
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Valspar Sourcing Inc
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/22—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to internal surfaces, e.g. of tubes
    • B05D7/227—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to internal surfaces, e.g. of tubes of containers, cans or the like
    • 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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/007—After-treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B21—MECHANICAL METAL-WORKING WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
    • B21D—WORKING OR PROCESSING OF SHEET METAL OR METAL TUBES, RODS OR PROFILES WITHOUT ESSENTIALLY REMOVING MATERIAL; PUNCHING METAL
    • B21D31/00—Other methods for working sheet metal, metal tubes, metal profiles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D25/00—Details of other kinds or types of rigid or semi-rigid containers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D25/00—Details of other kinds or types of rigid or semi-rigid containers
    • B65D25/34—Coverings or external coatings
    • 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
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
    • 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
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; 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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C09D171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C09D171/12—Polyphenylene oxides
    • 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
    • C09D5/08—Anti-corrosive paints
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2518/00—Other type of polymers
    • 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
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
    • Y10T428/1355—Elemental metal containing [e.g., substrate, foil, film, coating, etc.]

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Mechanical Engineering (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
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  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)

Description

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1,1-di(4-hidroxi-3,5-dimetilfenil)-ciclohexano.
En determinadas realizaciones preferentes, el polímero de poliéter incluye uno o más de los segmentos anteriores de Fórmula I, en la que: cada n es 1 y R incluye uno o más grupos policíclicos. En otra realización, R no incluye un grupo policíclico y el uno o más grupos policíclicos no están presentes en el polímero o están incluidos en diferentes segmentos del polímero.
En realizaciones preferentes, el polímero de poliéter incluye una pluralidad de segmentos de fórmula I, que están preferentemente dispersos a lo largo de un esqueleto del polímero, más preferentemente un esqueleto de poliéter. En realizaciones preferentes, los segmentos de Fórmula I constituyen una parte sustancial de las unidades estructurales totales del polímero. Normalmente, los segmentos de Fórmula I constituyen, en porcentaje en peso, al menos 10 % en peso, preferentemente al menos 30 % en peso e incluso más preferentemente al menos 40 % en peso del polímero. El porcentaje en peso de segmentos de Fórmula I en el polímero de poliéter puede estar por debajo de las cantidades indicadas anteriormente en ciertas situaciones e incluso puede ser sustancialmente inferior. A modo de ejemplo, la concentración de segmentos de Fórmula I puede estar fuera de los intervalos indicados anteriormente si el polímero de poliéter incluye componentes adicionales de gran peso molecular, tales como se pueden producir, por ejemplo, cuando el polímero es un copolímero tal como un copolímero que contiene acrílico (por ejemplo, un copolímero acrílico-poliéter formado por injerto de acrílico sobre un polímero de poliéter de la presente invención). En dichas realizaciones, el porcentaje en peso de segmentos de Fórmula I presentes en el polímero es tal como se ha descrito anteriormente, basado en el porcentaje en peso de los segmentos de Fórmula I con respecto a la fracción total de poliéter del polímero (sin considerar el peso total de las porciones no poliéter tales como, por ejemplo, porciones acrílicas). En general, la fracción total de poliéter del polímero se puede calcular sobre la base del peso total de poliepóxido y de los reactivos de fenol polihídrico (por ejemplo, monofenoles y/o difenoles polihídricos) incorporados en el polímero.
Se puede usar cualquier reactivo adecuado para formar el polímero de poliéter. En realizaciones preferentes, el polímero de poliéter es un producto de reacción de reactivos que incluye un compuesto poliepóxido (es decir, un compuesto que tiene dos o más grupos oxirano) y un fenol polihídrico. El polímero de poliéter es, normalmente, un producto de la reacción de uno o más compuestos diepóxido reaccionados con uno o más compuestos fenólicos dihídricos.
Ejemplos de fenoles dihídricos adecuados para su uso en la formación del polímero de poliéter incluyen compuestos de la Fórmula II siguiente:
HO-Ar-(Rn-Ar)n-OH, (II)
en la que Ar, R y n son como se han definido anteriormente para la Fórmula I. Por tanto, en algunas realizaciones, los compuestos de Fórmula II pueden usarse para incorporar segmentos de Fórmula I en el polímero de la invención. Ejemplos de dihidroxifenoles adecuados de Fórmula II incluyen hidroquinona, catecol, resorcinol, 1,1-bis(4hidroxifenil)-3,3,5-trimetil-ciclohexano, 1,1-di(4-hidroxifenil)-ciclohexano, 1,1-di (4-hidroxi-3-metilfenil)-ciclohexano, 1,1-di(4-hidroxi-3,5-dimetilfenil)-ciclohexano, dihidroxinaftaleno, 4,4’-bifenol, compuestos de difenol de la fórmula III siguiente o una mezcla de los mismos.
Los polímeros de poliéter de la presente invención pueden prepararse por métodos que implican el avance del peso molecular de los compuestos de Fórmula II. En determinadas realizaciones, se puede hacer reaccionar los compuestos de Fórmula II con un poliepóxido (más preferentemente, un diepóxido) para hacer avanzar el peso molecular, por ejemplo, se puede hacer reaccionar compuestos de fórmula II con diepóxidos no basados en BPA para formar polímeros de poliéter que tienen, preferentemente, grupos hidroxilo secundarios unidos a la estructura que se puede formular con reticulantes y aditivos para recubrimientos para envasado rígido. Como alternativa, los compuestos de Fórmula II se pueden hacer reaccionar con epiclorhidrina para formar un análogo diepóxido de compuestos de Fórmula II, que después puede hacerse reaccionar con otros compuestos de Fórmula II para formar un polímero que incluye segmentos de -CH2-CH(OH)-CH2-. A modo de ejemplo, se puede formar un polímero de poliéter de la presente invención haciendo reaccionar 1,1-di(4-hidroxifenil)-ciclohexano (o una variante sustituida del mismo) con un éter diglicidílico de 1,1-di (4-hidroxifenil)-ciclohexano (o una variante sustituida del mismo). Las
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completamente corroído, observado por la formación de burbujas o la formación de ampollas de la película en todas las áreas. Un "10" indica que el recubrimiento no ha cambiado desde antes de ser sometido al medio corrosivo.
Resistencia a las manchas
La resistencia a las manchas es una medida de la capacidad de un recubrimiento para resistir la tinción mediante un medio. Generalmente se mide en una escala de 0-10. Un "0" indica que el recubrimiento está completamente manchado, observándose un cambio de color completo de la película en todas las áreas. Un "10" indica que la coloración del recubrimiento no ha cambiado desde antes de ser sometido al ambiente de manchas.
Ensayo de resistencia a disolventes
El grado de "curado" o reticulación de un recubrimiento se mide como una resistencia a disolventes, tales como metiletilcetona (MEK) o alcohol isopropílico (IPA). Este ensayo se realiza como se describe en la norma ASTM D5402-93. Se indica el número de frotaciones dobles (es decir, un movimiento de vaivén). Preferentemente, la resistencia al disolvente MEK es de al menos 30 frotaciones dobles.
Ejemplos
Los ejemplos siguientes se ofrecen para ayudar a entender la presente invención y no deben interpretarse como limitantes del alcance de la misma. A menos que se indique lo contrario, todas las partes y porcentajes se expresan en peso.
Lista de materias primas e Ingredientes
En la tabla siguiente se enumeran algunas de las materias primas e ingredientes utilizados en los siguientes ejemplos. Pueden sustituirse materiales o suministradores alternativos como aprecia un experto en la técnica.
Materia prima
Suministrador Localización
PHENODUR PR 612 reticulante fenólico
Cytec Smyrna, Georgia
ERISYS GE-22 éter diglicidílico de ciclohexano dimetanol
CVC Thermoset Specialties Moorestown, NJ
1,1-bis(4-hidroxifenil)-3,3,5-trimetil-ciclohexano
Honshu Chemical Tokio, Japón
CATALYST 1201 catalizador de la polimerización
Shell Houston, Texas
1,1-di(4-hidroxifenil)-ciclohexano
Honshu Chemical Tokio, Japón
RDGE éter diglicidílico de resorcinol
CVC Thermoset Specialties Moorestown, NJ
EPON 828 éter diglicidílico de bisfenol A
Hexion Houston, Texas
Bisfenol A
Dow Chemical Midland, IF
Ejemplo 1: Polímeros de poliéter
Ciclo 1:
A un matraz de fondo redondo de 4 bocas equipado con un agitador mecánico, un condensador refrigerado con agua y un termopar conectado a un dispositivo de control de calentamiento y una camisa calefactora se añadieron 138,4 partes de ERISYS GE-22, 140,3 partes de 1,1-bis (4-hidroxifenil)-3,3,5-trimetil-ciclohexano, 0,26 partes de CATALYST 1201 y 13,4 partes de metilisobutilcetona. Se inició la agitación y el calentamiento y se continuó hasta que el lote alcanzó 130 ºC, momento en el cual se interrumpió el calentamiento y se dejó que el lote desprendiera calor a 158 ºC. El lote se calentó a 155 ºC durante 180 minutos, momento en el cual el valor de epoxi fue de 0,038 equivalentes/100 gramos. En este momento se interrumpió el calentamiento cuando se añadieron lentamente 84,2 partes de éter butílico de etilenglicol, seguido de 42,1 partes de butanol. La resina final tenía un contenido de no volátiles de 66,9 %, un valor de epoxi de 0,036, una viscosidad de Brookfield de 75.000 Centipoise a ~ 27 ºC (80 ºF) y una Tv de 60 ºC. Basándose en un cálculo teórico, la resina final incluía 20,6 % en peso de grupos arilo, basado en el peso total de los grupos arilo en el polímero con relación al peso del polímero.
Ciclo 2:
A un matraz de fondo redondo de 4 bocas equipado con un agitador mecánico, un condensador refrigerado con agua y un termopar conectado a un dispositivo de control de calentamiento y una camisa calefactora se añadieron 169,8 partes de ERISYS GE-22, 130,2 partes de 1,1-di(4-hidroxifenil)-ciclohexano, 0,30 partes de catalizador 1201 y 15,9 partes de metilisobutilcetona. Se inició la agitación y el calentamiento y se continuó hasta que el lote alcanzó 125 ºC, momento en el cual se interrumpió el calentamiento y se dejó que el lote desprendiera calor a 166 ºC. El lote se calentó a 155 ºC durante 120 minutos, momento en el cual el valor de epoxi fue de 0,035 equivalentes/100 gramos. En este momento se interrumpió el calentamiento cuando se añadieron lentamente 122 partes de éter
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se almacenaron durante 2 semanas a 120 ºF (~49 ºC). Después de 2 semanas se retiraron los extremos del producto alimentario, se aclararon con agua y se evaluó la adherencia, la corrosión, las manchas y el velado. Los resultados se muestran en la Tabla 2 siguiente.
5 Tal como se muestra en la Tabla 2, las formulaciones que contienen RDGE de los Ejemplos 4 y 5 muestran un rendimiento similar a la formulación que contiene BPA del Ejemplo Comparativo 6. Las formulaciones que contienen CHDMDGE de Tv menor de los Ejemplos 2 y 3 fueron inferiores en este ensayo a las formulaciones que contienen RDGE de Tv mayor de los Ejemplos 4 y 5.
10 Tabla 2
Composición de recubrimiento
Ejemplo 2 Ejemplo 3 Ejemplo 4 Ejemplo 5 Ejemplo comparativo 6
Resina
Ejemplo 1, Ciclo 1 Ejemplo 1, Ciclo 2 Ejemplo 1, Ciclo 1 Ejemplo 1, Ciclo 2 Ejemplo 1, Ciclo 5
ETP
Producto alimentario agresivo 1
Adherencia/Velado
8/10 8/10 10/10 10/10 10/10
Manchas/Corrosión
7/7 5/7 10/10 10/10 10/10
Producto alimentario agresivo 2
Adherencia/Velado
8/10 8/10 10/10 10/10 10/10
Manchas/Corrosión
7/7 5/5 9/9 10/9 10/10
TFS
Producto alimentario agresivo 1
Adherencia/Velado
8/7 8/7 10/10 10/10 10/10
Manchas/Corrosión
9/7 9/5 10/10 10/10 10/10
Producto alimentario agresivo 2
Adherencia/Velado
8/5 8/5 10/10 10/10 10/10
Manchas/Corrosión
9/7 9/5 10/9 10/8 10/10
Los siguientes Ejemplos 7-13 se refieren a realizaciones de la presente invención que incluyen un polímero de poliéter que tiene grupos policíclicos opcionales.
15 Ejemplo 7: Aducto de 2 moles de ácido 4-hidroxifenilacético (HPAA) con 1 mol de triciclodecano dimetanol (TCDM)
A un matraz de fondo redondo de 4 bocas equipado con un agitador mecánico, un condensador refrigerado con agua encima de una trampa de Dean-Stark y un termopar conectado un dispositivo de control de calentamiento y 20 una camisa calefactora se añadieron 705,6 partes de TCDM (de OXEA), 1094,4 partes de HPAA (de Aceto), 1,8 partes del catalizador de la polimerización CATALYST 4201 (óxido de dibutilestaño de Atofina). Se inició la agitación y el calentamiento durante 4 horas hasta que el lote alcanzó los 230 ºC. El lote se calentó a 230 ºC durante 4 horas más, momento en el cual el índice de acidez fue de 2,0 mg de KOH/gramo. En este momento, el calentamiento se interrumpió hasta que el lote alcanzó 120 ºC, momento en el que se descargó el lote. El material era un semisólido
25 pegajoso a temperatura ambiente.
Ejemplo 8: Aducto de 2 moles de ácido 4-hidroxifenilacético (HPAA) con 1 mol de isosorbida
A un matraz de fondo redondo de 4 bocas equipado con un agitador mecánico, un condensador refrigerado con
30 agua encima de una trampa de Dean-Stark y un termopar conectado un dispositivo de control de calentamiento y una camisa calefactora se añadieron 162,2 partes de isosorbida (de calidad polimérica de ADM), 337,8 partes de HPAA, 0,5 partes del catalizador de la polimerización CATALYST 4201. Se inició la agitación y el calentamiento
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US20130280455A1 (en) 2013-10-24
US20210024774A1 (en) 2021-01-28
WO2011130671A3 (en) 2012-03-15
CN106085168B (zh) 2018-10-16
PL2558543T3 (pl) 2018-01-31
KR20130061132A (ko) 2013-06-10
RU2544676C2 (ru) 2015-03-20
JP5752784B2 (ja) 2015-07-22
US11130881B2 (en) 2021-09-28
WO2011130671A2 (en) 2011-10-20
EP2558543B1 (en) 2017-08-30
RU2012140144A (ru) 2014-05-27
EP3611235A1 (en) 2020-02-19
BR112012026240A2 (pt) 2020-07-28
JP2013529226A (ja) 2013-07-18
CA2793541A1 (en) 2011-10-20
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CN106085168A (zh) 2016-11-09
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AU2011239491A1 (en) 2012-09-27
EP2558543A4 (en) 2014-07-30
US20180112102A1 (en) 2018-04-26
CN102858893B (zh) 2016-08-03
KR102032749B1 (ko) 2019-10-16
EP3263664B1 (en) 2020-11-04
BR112012026240B1 (pt) 2021-08-03
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EP3263664A1 (en) 2018-01-03
MX2012011843A (es) 2012-11-12

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