ES2659559T3 - Composición de adhesivo de doble curado con transparencia óptica - Google Patents

Composición de adhesivo de doble curado con transparencia óptica Download PDF

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ES2659559T3
ES2659559T3 ES12824090.0T ES12824090T ES2659559T3 ES 2659559 T3 ES2659559 T3 ES 2659559T3 ES 12824090 T ES12824090 T ES 12824090T ES 2659559 T3 ES2659559 T3 ES 2659559T3
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acrylate
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Rui Zhang
Daoqiang Lu
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Henkel AG and Co KGaA
Henkel IP and Holding GmbH
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Henkel IP and Holding GmbH
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J109/00—Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having 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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Una composición de adhesivo de doble curado con transparencia óptica, basado en el peso total de la composición de adhesivo, la composición comprende: el 60-70 % en peso de oligómero de uretano que tiene un grupo (met)acriloxi; el 20-40 % en peso de (met)acrilato; el 2-3 % en peso de fotoiniciador UV; y el 2-3 % en peso de iniciador térmico, en la que dicho oligómero de uretano que tiene un grupo (met)acriloxi tiene un grado medio de funcionalidad de 0,5 a 2,5; y la temperatura de transición vítrea Tg de la misma es de -60 a 0 ºC, y la viscosidad Brookfield de la misma a la temperatura de 25 ºC es de 5000 cps a 100000 cps, y el peso molecular medio numérico de 2000- 8000 Daltons, en la que dicho (met)acrilato se selecciona del grupo que consiste en acrilato de 2-(2-etoxietoxi)etilo, (met)acrilato de isobornilo, (met)acrilato de 2-hidroxipropilo, (met)acrilato de etilenglicol diciclopentenil éter y cualquier combinación de los mismos, y en la que dicho fotoiniciador UV se selecciona de: 2-hidroxi-2-metil-1-fenil-propan-1-ona, óxido de difenil (2,4,6- trimetil-benzoil)fosfina y una combinación de los mismos y en la que dicho iniciador térmico es peróxido orgánico seleccionado del grupo que consiste en 1,1-bis(terc butilperoxi)-3,3,5-trimetil ciclohexano, peroxibenzoato de terc-butilo y una combinación de los mismos.

Description

imagen1
imagen2
imagen3
imagen4
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imagen8
Prueba 4: experimento de transmitancia de luz
Se adoptó un espectrofotómetro de luz UV-luz visible para medir la transmitancia de la luz del material adhesivo tras el curado. El grosor del material adhesivo curado se controló a 100 µm aproximadamente. El procedimiento de
5 prueba se realizó según especificación de la norma ASTM D1005-2007. Tras la irradiación de UVA de 100 mW/cm2 para la composición de adhesivo entre láminas de vidrio y vidrio durante 30 segundos, se midió la transmitancia de la composición de adhesivo en consecuencia.
Prueba 5: revisión de área de sombra
10 Se mantuvo el área aplicada con la composición de adhesivo o el área solapada entre las láminas de prueba en completa oscuridad. Tras dicha disposición, se realizó el curado térmico de la composición de adhesivo. Después de alcanzar la condición de prueba del curado térmico, se revisan los resultados del cuerpo que se va a unir.
15 <Materia prima usada>
Compuestos
Productos
oligómero de uretano que tiene grupo (met)acriloxi 1-1
Genomer 4188/EHA (Rahn AG): mezcla que consiste en el 80 % en peso de un oligómero con base de poliéster con función monoacrilato que comprende al menos un enlace de uretano y el 20 % de monómeros de acrilato de 2-etilhexilo; el oligómero comprendido por GENOMER 4188 tiene un peso molecular medio en peso Mw de aproximadamente 8.000, grado medio de funcionalidad de aproximadamente 1, viscosidad a 25 °C: aproximadamente 70000 cps, Tg: aproximadamente -3 ºC
oligómero de uretano que tiene grupo (met)acriloxi 1-2
CN 9021 (empresa Sartomer, Inc.), grado medio de funcionalidad: 2, viscosidad a 25 °C: aproximadamente 32000 cps, Tg: -54 °C
oligómero de uretano que tiene grupo (met)acriloxi 1-3
CN 8004 (empresa Sartomer, Inc.); grado medio de funcionalidad: menos de 2, viscosidad a 60 °C: aproximadamente 9000 cps, Tg: aproximadamente -3 °C
poliisopreno que tiene grupo metacriloxi 2-1
UC-102 (empresa Kuraray), grado medio de funcionalidad: 2, peso molecular medio numérico: alrededor de 17.000, Tg: -60 °C
poliisopreno que tiene grupo metacriloxi
UC-203 (empresa Kuraray), grado medio de funcionalidad: 3, peso molecular medio numérico:
2-2
alrededor de 35.000, Tg: -60 °C
polibutadieno líquido 3-1
Ricon130 (empresa Sartomer, Inc.), peso molecular medio numérico: alrededor de 2500
monómero de (met)acrilato 4-1
acrilato de isobornilo disponible en el mercado
monómero de (met)acrilato 4-2
metacrilato de hidroxipropilo disponible en el mercado
monómero de (met)acrilato 4-3
acrilato de 2-(2-etoxietoxi)etilo disponible en el mercado
monómero de (met)acrilato 4-4
Metacrilato de etilenglicol diciclopentenil éter disponible en el mercado
Fotoiniciador UV 5-1
2-hidroxi-2-metil-1-fenil-1-propanona (empresa BASF, Inc.)
Fotoiniciador UV 5-2
óxido de difenil(2,4,6-trimetilbenzoil)-fosfina (empresa BASF, Inc.)
iniciador térmico 6-1
1,1-bis(terc-butilperoxi)-3,3,5-trimetil ciclohexano (J & K Scientific Ltd.)
iniciador térmico 6-2
peroxibenzoato de terc-butilo
Otros compuestos usados en los ejemplos son reactivos químicamente puros, y todos están disponibles en el mercado.
20 Ejemplo 1 (inventivo) La composición de adhesivo 1 se formuló de acuerdo con la composición de la tabla 1 y el método de formulación como se muestra a continuación:
25 10
imagen9
imagen10
Tabla 7
Componentes
Contenidos
poliisopreno que tiene grupo metacriloxi 2-1
30 partes en peso
Polibutadieno líquido 3-1
40 partes en peso
(Met)acrilato 4-2
12 partes en peso
(Met)acrilato 4-4
12 partes en peso
Fotoiniciador UV 5-1
2 partes en peso
Fotoiniciador UV 5-2
1 parte en peso
Iniciador térmico 6-1
2 partes en peso
Iniciador térmico 6-2
1 parte en peso
5 Ejemplo 8 (no inventivo) La composición de adhesivo 8 se formuló de acuerdo con la composición de la tabla 8 y el método como se muestra en el ejemplo 1. 10 Tabla 8
Componentes
Contenidos
poliisopreno que tiene grupo metacriloxi 2-1
30 partes en peso
poliisopreno que tiene grupo metacriloxi 2-2
10 partes en peso
Polibutadieno líquido 3-1
33 partes en peso
(Met)acrilato 4-1
12 partes en peso
(Met)acrilato 4-2
12 partes en peso
Fotoiniciador UV 5-1
2 partes en peso
Fotoiniciador UV 5-2
1 parte en peso
Ejemplo 9 (inventivo) 15 La composición de adhesivo 9 se formuló de acuerdo con la composición de la tabla 9 y el método como se muestra en el ejemplo 1. Tabla 9
Componentes
Contenidos
poliisopreno que tiene grupo metacriloxi 2-1
50 partes en peso
(Met)acrilato 4-1
12 partes en peso
(Met)acrilato 4-2
12 partes en peso
(Met)acrilato 4-4
20 partes en peso
Fotoiniciador UV 5-1
2 partes en peso
Fotoiniciador UV 5-2
1 parte en peso
Iniciador térmico 6-1
2 partes en peso
Iniciador térmico 6-2
1 parte en peso
20
Ejemplo 10 (inventivo)
25
La composición de adhesivo 10 se formuló de acuerdo con la composición de la tabla 10 y el método como se muestra en el ejemplo 1.
13
imagen11

Claims (1)

  1. imagen1
ES12824090.0T 2011-08-12 2012-08-09 Composición de adhesivo de doble curado con transparencia óptica Active ES2659559T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201110230724 2011-08-12
CN2011102307241A CN102925062A (zh) 2011-08-12 2011-08-12 光学透明的双固化粘合剂
PCT/CN2012/079869 WO2013023545A1 (en) 2011-08-12 2012-08-09 Optical transparent dual cure adhesives composition

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Publication Number Publication Date
ES2659559T3 true ES2659559T3 (es) 2018-03-16

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US (3) US20140163130A1 (es)
EP (1) EP2742108B1 (es)
JP (1) JP2014527106A (es)
KR (1) KR101951974B1 (es)
CN (2) CN102925062A (es)
ES (1) ES2659559T3 (es)
TW (1) TWI553082B (es)
WO (1) WO2013023545A1 (es)

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