WO2008003191A1 - Radiation curable adhesion promoter - Google Patents

Radiation curable adhesion promoter Download PDF

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Publication number
WO2008003191A1
WO2008003191A1 PCT/CN2006/003385 CN2006003385W WO2008003191A1 WO 2008003191 A1 WO2008003191 A1 WO 2008003191A1 CN 2006003385 W CN2006003385 W CN 2006003385W WO 2008003191 A1 WO2008003191 A1 WO 2008003191A1
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WO
WIPO (PCT)
Prior art keywords
radiation curable
adhesion promoter
adhesion
acrylate
amino groups
Prior art date
Application number
PCT/CN2006/003385
Other languages
French (fr)
Inventor
Jibing Lin
Jinshan Zhang
Original Assignee
Shanghai Phichem Corporation
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Filing date
Publication date
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Publication of WO2008003191A1 publication Critical patent/WO2008003191A1/en

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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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/809—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
    • 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
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
    • C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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

Definitions

  • This invention relates to a new type of radiation curable adhesion promoters, which can be applied to coatings, inks and adhesives to improve adhesion between cured materials and substrates. In particular they can be applied to radiation curable coatings and adhesives to promote adhesion between cured materials and substrates.
  • Radiation curable materials have been developed rapidly in the past 20 years. They have been widely used in coatings, inks and adhesives etc since they provide high productivity, low energy consumption and zero environment pollution. Radiation curable materials are in general composed of four ingredients: oligomers, reactive monomers, photoinitiators and additives. Radiation curable materials are commonly first coated on the substrates, and cured via radiation resources (ultraviolet light or electron beam). The adhesion between the substrates and the cured radiation curable materials varies considerably from system to system. Adhesion promoters are the most common additives that improve adhesion between cured materials and substrates. The most common adhesion promoters are alkoxysilanes.
  • Alkoxysilane adhesion promoters are generally polymerization inactive-can not participate in polymerization reactions of monomers and oligomers during curing. As a result, their levels in formulations are considerably limited.
  • the only commonly used polymerizable alkoxysilane adhesion promoter in industry is methacryloxypropyl trimethoxysilane. However it contains a certain level of starting material-allylmethacrylate, which is a volatile and odorous compound. Therefore its applicability is limited. See Waldman, Silane Coupling Agents Improving Performance, Modern Paints and Coatings, February, 1996.
  • WO 96/12749 discloses an oligomer containing alkoxysilanes and optical fiber coating containing the oligomer.
  • the silane oligomers are high in molecular weight (500-11000) and a high level of silane oligomers in the composition is needed (5-99%).
  • Such oligomers are typically polyurethane materials.
  • this invention provides a radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilane containing isocyanate, with acrylate or methacrylate monomers containing hydroxy or amino groups, at 40-60 0 C in the presence of dibutyltion dilaurate catalyst, as shown in Equation 1 :
  • the second radiation curable adhesion promoter put forward in this invention was obtained by reaction of acrylate or methacrylate containing hydroxy or amino groups, with diisocyanate, followed by reaction with alkoxysilane containing mercapto or amino groups, as shown in Equation 2.
  • above two radiation curable adhesion promoters in this invention due to polymerization activity, are unrestricted in quantity in their application to coatings, inks, and adhesives.
  • Particularly in radiation curable coatings, inks and adhesives use of above adhesion promoters in large quantities can greatly change adhesion power between cured materials and substrates.
  • Equation 1 20.5 g of 3-isocyanate propyl trimethylsilane and 0.02 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 13.0 g of 2-hydroxyethyl methyl methacrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 40 0 C for an hour and the content of isocyanate was below 0.1% obtained by chemical titration. The resulting light yellow liquid was radiation curable adhesion promoter A.
  • DBTDL dibutyltion dilaurate
  • Equation 2 22.3 g of isophorone diisocyanate (IPDI) and 0.03 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 17.4 g of 2-hydroxyethyl acrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 40 0 C for an hour and then 19.6 g of 3-mercapto propyl trimethoxysilane was added. After heating to 80 0 C for 12 hours the resulting viscous and colorless liquid was radiation curable adhesion promoter B. Its viscosity was 34000 cps (60 0 C).
  • IPDI isophorone diisocyanate
  • DBTDL dibutyltion dilaurate
  • HDDA 12% hexane-l,6-diol diacrylate
  • trimethlolpropane triacrylate (TMPTA)

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

New type of adhesion promoter in particular can be used in radiation curable coating material, adhesive and ink. This adhesion promoter is obtained by fast reaction of alkoxysilane containing isocyanate, with acrylate or methacrylate monomers containing hydroxyl or amino groups, in the presence of dibutyltin dilaurate catalyst at a temperature 40-60°C. This adhesion promoter has adhesion promotive functional groups such as alkoxysilanes at one end, and polymerisable groups of (meth)acrylate at the other end. This invention can be applied to coating material, adhesive and ink to improve adhesion between cured materials and substrates.

Description

RADIATION CURABLE ADHESION PROMOTER
Technical Field
This invention relates to a new type of radiation curable adhesion promoters, which can be applied to coatings, inks and adhesives to improve adhesion between cured materials and substrates. In particular they can be applied to radiation curable coatings and adhesives to promote adhesion between cured materials and substrates. Background Art
Radiation curable materials (including ultraviolet light curable materials and electron beam curable materials) have been developed rapidly in the past 20 years. They have been widely used in coatings, inks and adhesives etc since they provide high productivity, low energy consumption and zero environment pollution. Radiation curable materials are in general composed of four ingredients: oligomers, reactive monomers, photoinitiators and additives. Radiation curable materials are commonly first coated on the substrates, and cured via radiation resources (ultraviolet light or electron beam). The adhesion between the substrates and the cured radiation curable materials varies considerably from system to system. Adhesion promoters are the most common additives that improve adhesion between cured materials and substrates. The most common adhesion promoters are alkoxysilanes.
Alkoxysilane adhesion promoters are generally polymerization inactive-can not participate in polymerization reactions of monomers and oligomers during curing. As a result, their levels in formulations are considerably limited. The only commonly used polymerizable alkoxysilane adhesion promoter in industry is methacryloxypropyl trimethoxysilane. However it contains a certain level of starting material-allylmethacrylate, which is a volatile and odorous compound. Therefore its applicability is limited. See Waldman, Silane Coupling Agents Improving Performance, Modern Paints and Coatings, February, 1996.
On May 2, 1996, WO 96/12749 discloses an oligomer containing alkoxysilanes and optical fiber coating containing the oligomer. The silane oligomers are high in molecular weight (500-11000) and a high level of silane oligomers in the composition is needed (5-99%). Such oligomers are typically polyurethane materials.
On the other hand, US patent US6391463B1 discloses a new polymerisable alkoxysilane monomer, which is obtained by hydrosilylation reactions. Disclosure of Invention
Aiming at above-mentioned shortcomings of current technologies, it is an object of this invention to provide two easily made and industrialized new adhesion promoters, which are polymerizable thus can be widely applied to radiation curable coatings, inks, and adhesives at high contents.
In order to solve above technical problems, this invention provides a radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilane containing isocyanate, with acrylate or methacrylate monomers containing hydroxy or amino groups, at 40-600C in the presence of dibutyltion dilaurate catalyst, as shown in Equation 1 :
cat. DBTDL
Figure imgf000004_0001
Equation 1
The second radiation curable adhesion promoter put forward in this invention was obtained by reaction of acrylate or methacrylate containing hydroxy or amino groups, with diisocyanate, followed by reaction with alkoxysilane containing mercapto or amino groups, as shown in Equation 2.
DBTDL
Figure imgf000004_0002
Figure imgf000004_0003
Figure imgf000004_0004
(X= NH, NR, S) Equation 2
In contrast to current techniques, above two radiation curable adhesion promoters in this invention due to polymerization activity, are unrestricted in quantity in their application to coatings, inks, and adhesives. Particularly in radiation curable coatings, inks and adhesives use of above adhesion promoters in large quantities can greatly change adhesion power between cured materials and substrates. Modes for Carrying Out the Invention
This invention will be further described with the following illustrative examples: Example 1
According to Equation 1, 20.5 g of 3-isocyanate propyl trimethylsilane and 0.02 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 13.0 g of 2-hydroxyethyl methyl methacrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 400C for an hour and the content of isocyanate was below 0.1% obtained by chemical titration. The resulting light yellow liquid was radiation curable adhesion promoter A. Example 2
According to Equation 2, 22.3 g of isophorone diisocyanate (IPDI) and 0.03 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 17.4 g of 2-hydroxyethyl acrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 400C for an hour and then 19.6 g of 3-mercapto propyl trimethoxysilane was added. After heating to 800C for 12 hours the resulting viscous and colorless liquid was radiation curable adhesion promoter B. Its viscosity was 34000 cps (600C). Example 3
According to Equation 2, 22.3 g of isophorone diisocyanate (IPDI) and 0.03 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 17.4 g of 2-hydroxyethyl methacrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 400C for an hour and then 22.1 g of N-ethyl-3-aminoisobutyl trimethylsilane and 14 g of isobornyl acrylate.(IBOA) monomer as a dilution agent were added. After agitation at 600C for 1 hour the resulting viscous and yellow liquid was radiation curable adhesion promoter C. Its viscosity was 8300 cps (250C). Example 4-Radiation curable adhesive
50% radiation curable adhesion promoter B
47% isobornyl acrylate (IBOA)
3% 1-hydroxycyclohexyl phenyl ketone (Irgacure 184)
Above ingredients were added successively into a reactor. After agitation at 600C for two hours an UV curable adhesive was obtained via filtration. Its viscosity was 400 cps at 250C. The adhesive can be used in bonding metals and glass etc with very tight bonding. Example 5-UV curable ink 45% aromatic polyurethane acrylate oligomer (RMAT 650)
12% hexane-l,6-diol diacrylate (HDDA)
20% trimethlolpropane triacrylate (TMPTA)
15% white color paste (55% titanium dioxide dispersed in TMPTA)
3% 1 -hydroxy cyclohexyl phenyl ketone (Irgacure 184)
1% 2,4,6-trimethylphenol (Irganox 1010)
4% radiation curable adhesion promoter B
Above ingredients were added successively into a reactor. After agitation at 600C for two hours an UV curable ink was obtained via filtration. Its viscosity was 1720 cps at 250C. This UV curable ink has good bonding to glass, metals, and some plastics. Other colored inks can be made in a similar way to above.

Claims

1. A radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilane containing isocyanate, with acrylate or methacrylate monomers containing hydroxy or amino groups, at 40-600C in the presence of dibutyltion dilaurate catalyst.
2. A radiation curable adhesion promoter, which is obtained by reaction of acrylate or methacrylate containing hydroxy or amino groups, with diisocyanate, followed by reaction with alkoxysilane containing mercapto or amino groups.
3. A radiation curable coating, which contains 0.1-60% radiation curable promoters of claim 1 or/and 2.
4. A radiation curable adhesive, which contains 0.1-99% radiation curable promoters of claim 1 or/and 2.
5. A radiation curable ink, which contains 0.1-10% radiation curable promoters of claim 1 or/and 2.
PCT/CN2006/003385 2006-06-26 2006-12-13 Radiation curable adhesion promoter WO2008003191A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200610028117.6 2006-06-26
CNA2006100281176A CN101096472A (en) 2006-06-26 2006-06-26 Adhesive property promoter for radiation curing material

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011023409A1 (en) 2009-08-31 2011-03-03 Byk-Chemie Gmbh Adhesion promoter for coatings on different substrate surfaces
CN102516907A (en) * 2011-12-13 2012-06-27 烟台德邦电子材料有限公司 Preparation method of ultraviolet-curable organosilicone-modified pressure-sensitive adhesive
US8784947B2 (en) * 2008-10-15 2014-07-22 Kansai Paint Co., Ltd. Silsesquioxane compound having polymerizable functional group
US9856392B2 (en) 2010-12-28 2018-01-02 Akzo Nobel Coatings International B.V. Radiation curable coating compositions for metal
CN110734713A (en) * 2019-11-27 2020-01-31 上海蒂姆新材料科技有限公司 adhesion promoter for adhesive, synthesis method and application
US11028214B2 (en) 2018-01-22 2021-06-08 Corning Incorporated Synthesis of oligomer for optical fiber coating
JP2021531359A (en) * 2018-06-12 2021-11-18 ダウ シリコーンズ コーポレーション Aqueous hybrid pressure-sensitive adhesive composition and method for producing the same

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CN102140110A (en) * 2010-09-08 2011-08-03 上海飞凯光电材料股份有限公司 High-adhesive force radiation curable activated monomer and preparation method and use thereof
CN101921511B (en) * 2010-09-16 2012-04-25 珠海保税区天然宝杰数码科技材料有限公司 Ink composition for ink-jet printing
CN102167925A (en) * 2011-03-02 2011-08-31 中国科学院长春应用化学研究所 Adhesion promoter of optical fiber coating and preparation method thereof
CN103172830A (en) * 2013-02-25 2013-06-26 淮南联合大学 Method for modifying acrylic ester by using organic silicon
TWI527863B (en) * 2014-12-17 2016-04-01 奇美實業股份有限公司 Peelable adhesive composition and peelable tape
CN109868107B (en) * 2017-12-01 2021-04-20 万华化学（宁波）有限公司 Adhesive and preparation method and application thereof
KR20210081391A (en) * 2018-11-20 2021-07-01 아그파-게바에르트 엔.브이. Radiation Curable Inkjet Inks for Manufacturing Printed Circuit Boards
CN115340783B (en) * 2022-08-31 2023-07-04 武汉镱得飞光电技术有限公司 Optical fiber coating adhesion promoter and preparation method thereof
CN115785850B (en) * 2022-11-30 2024-05-28 成都硅宝科技股份有限公司 Adhesion promoter, preparation method and application thereof, and waterproof adhesive single-component polyurethane sealant, and preparation method and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5041494A (en) * 1987-11-03 1991-08-20 Bayer Aktiengesellschaft Aqueous solutions or dispersions of polyurethanes, a process for their preparation and their use in coating compositions
US5854338A (en) * 1997-04-14 1998-12-29 Bayer Aktiengesellschaft Aqueous two-component binders and their use in coating and sealing compositions
CN1487982A (en) * 2001-01-24 2004-04-07 Polyurethane bonding agent having two constituents and used as an adhesive

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5041494A (en) * 1987-11-03 1991-08-20 Bayer Aktiengesellschaft Aqueous solutions or dispersions of polyurethanes, a process for their preparation and their use in coating compositions
US5854338A (en) * 1997-04-14 1998-12-29 Bayer Aktiengesellschaft Aqueous two-component binders and their use in coating and sealing compositions
CN1487982A (en) * 2001-01-24 2004-04-07 Polyurethane bonding agent having two constituents and used as an adhesive

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8784947B2 (en) * 2008-10-15 2014-07-22 Kansai Paint Co., Ltd. Silsesquioxane compound having polymerizable functional group
WO2011023409A1 (en) 2009-08-31 2011-03-03 Byk-Chemie Gmbh Adhesion promoter for coatings on different substrate surfaces
US8778458B2 (en) 2009-08-31 2014-07-15 Byk-Chemie Gmbh Adhesion promoter for coatings on different substrate surfaces
US9593246B2 (en) 2009-08-31 2017-03-14 Byk-Chemie Gmbh Object or an article whose surface is provided with a coating produced using and adhesion promoter
US9856392B2 (en) 2010-12-28 2018-01-02 Akzo Nobel Coatings International B.V. Radiation curable coating compositions for metal
CN102516907A (en) * 2011-12-13 2012-06-27 烟台德邦电子材料有限公司 Preparation method of ultraviolet-curable organosilicone-modified pressure-sensitive adhesive
US11028214B2 (en) 2018-01-22 2021-06-08 Corning Incorporated Synthesis of oligomer for optical fiber coating
JP2021531359A (en) * 2018-06-12 2021-11-18 ダウ シリコーンズ コーポレーション Aqueous hybrid pressure-sensitive adhesive composition and method for producing the same
JP7193553B2 (en) 2018-06-12 2022-12-20 ダウ シリコーンズ コーポレーション Aqueous hybrid pressure-sensitive adhesive composition and method for producing the same
US12024658B2 (en) 2018-06-12 2024-07-02 Dow Silicones Corporation Water-based hybrid pressure sensitive adhesive composition and method of producing the same
CN110734713A (en) * 2019-11-27 2020-01-31 上海蒂姆新材料科技有限公司 adhesion promoter for adhesive, synthesis method and application

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