CN112210327A - OCA optical cement, preparation method and application thereof - Google Patents

OCA optical cement, preparation method and application thereof Download PDF

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Publication number
CN112210327A
CN112210327A CN202011083404.3A CN202011083404A CN112210327A CN 112210327 A CN112210327 A CN 112210327A CN 202011083404 A CN202011083404 A CN 202011083404A CN 112210327 A CN112210327 A CN 112210327A
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Prior art keywords
oca optical
optical cement
release film
molecular weight
steps
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Chinese (zh)
Inventor
刘晓阳
金成国
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Shixing Technology Co ltd
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Shixing Technology Co ltd
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Priority to CN202011083404.3A priority Critical patent/CN112210327A/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/38Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/10Adhesives in the form of films or foils without carriers

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses an OCA optical cement, a preparation method and application thereof, wherein the OCA optical cement comprises 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and a molecular weight control agent dodecyl mercaptan; the preparation method of the OCA optical cement comprises the following steps: the method comprises the following steps: mixing 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and dodecyl mercaptan to obtain a monomer prepolymer; step two: exposing the monomer prepolymer to ultraviolet radiation in a nitrogen protection environment, and adding a photoinitiator and a crosslinking agent to obtain OCA optical cement; the application of the OCA optical cement comprises the following steps: step A: unreeling the release film; and B: coating OCA optical cement on the release film to obtain the release film coated with the OCA optical cement; and C: placing the release film coated with the OCA optical cement under illumination to be cured to obtain a cured release film; step D: and winding the cured release film.

Description

OCA optical cement, preparation method and application thereof
Technical Field
The invention relates to the field of adhesives, in particular to an OCA optical adhesive, a preparation method and an application thereof.
Background
At present, most adhesives on the market are produced by heating and thermal polymerization in a reaction kettle, and in the production and heating process, the phenomena of solvent backflow, pressure rise and the like are accompanied, and some optical adhesives are produced by UV ultraviolet polymerization, but the production process cannot be controlled in the production process, and the molecular weight of polymers cannot be controlled in the polymerization process.
Disclosure of Invention
The invention aims to provide an OCA optical adhesive with controllable molecular weight, a preparation method and application thereof.
The technical scheme adopted by the invention for solving the technical problems is as follows: an OCA optical adhesive comprises 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and a molecular weight control agent, dodecyl mercaptan.
Further, the method comprises the following steps: the part range of the acrylic acid-2-ethylhexyl ester is 30-95, the part range of the acrylic acid isobornyl ester is 0-50, the part range of the 2-hydroxyethyl acrylate is 0-30, the part range of the 1-hydroxycyclohexyl benzophenone is 0.01-1, and the part range of the molecular weight control agent dodecyl mercaptan is 0-2.
The preparation method of the OCA optical cement comprises the following steps:
the method comprises the following steps: mixing 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and dodecyl mercaptan to obtain a monomer prepolymer;
step two: and (3) adding a photoinitiator and a crosslinking agent into the monomer prepolymer obtained in the step one by exposing to ultraviolet radiation under the environment of nitrogen protection to obtain the OCA optical adhesive.
Further, the method comprises the following steps: the molecular weight of the monomer prepolymer is controllable, so that different OCA optical cement can be prepared according to different requirements.
Further, the method comprises the following steps: the molecular weight of the monomer prepolymer can be controlled by changing the ultraviolet energy intensity, changing the part of the photoinitiator or changing the part of the molecular weight control agent.
The application of the OCA optical cement comprises a preparation method of the OCA optical cement, and further comprises the following steps:
step A: unreeling the release film;
and B: uniformly coating OCA optical cement on the unreeled release film in the step A to obtain the release film coated with the OCA optical cement;
and C: placing the release film coated with the OCA optical adhesive in the step B under illumination for curing to obtain a cured optical adhesive film;
step D: and C, rolling the cured optical adhesive film obtained in the step C.
The invention has the beneficial effects that: the invention can control the molecular weight of the monomer prepolymer by changing the ultraviolet energy intensity, the part of the photoinitiator or the part of the molecular weight control agent, so that different OCA optical adhesives can be prepared according to different requirements.
Detailed Description
The present invention will be further described with reference to the following embodiments.
An OCA optical adhesive comprises 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and a molecular weight control agent, dodecyl mercaptan.
On the basis of the above, the part range of the acrylic acid-2-ethylhexyl ester is 30-95, the part range of the acrylic acid isobornyl ester is 0-50, the part range of the 2-hydroxyethyl acrylate is 0-30, the part range of the 1-hydroxycyclohexyl benzophenone is 0.01-1, and the part range of the molecular weight control agent dodecyl mercaptan is 0-2.
The preparation method of the OCA optical cement comprises the following steps:
the method comprises the following steps: mixing 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and dodecyl mercaptan to obtain a monomer prepolymer;
step two: adding a photoinitiator and a crosslinking agent into the monomer prepolymer obtained in the step one by exposing to ultraviolet radiation in a nitrogen protection environment to obtain the OCA optical cement, wherein the photoinitiator can be 11732-hydroxy-2-methyl-1-phenyl acetone, 1841-hydroxycyclohexyl phenyl ketone, 9072-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone, TPO-2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide, TPO-L2, 4, 6-trimethyl benzoyl phenyl ethyl phosphonate, IHT-9102-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone, or, 6592 hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone or MBF benzoyl carboxylic acid methyl ester.
On the basis, the molecular weight of the monomer prepolymer is controllable, so that different OCA optical adhesives can be manufactured according to different requirements.
On the basis of the above, the molecular weight of the monomer prepolymer can be controlled by changing the ultraviolet energy intensity, changing the part of the photoinitiator or changing the part of the molecular weight control agent.
The application of the OCA optical cement comprises a preparation method of the OCA optical cement, and further comprises the following steps:
step A: unreeling the release film;
and B: uniformly coating OCA optical cement on the unreeled release film in the step A to obtain the release film coated with the OCA optical cement;
and C: placing the release film coated with the OCA optical adhesive in the step B under illumination for curing to obtain a cured optical adhesive film;
step D: and C, rolling the cured optical adhesive film obtained in the step C.
The first embodiment is as follows:
an OCA optical adhesive comprises 65 parts of 2-ethylhexyl acrylate, 14.5 parts of isobornyl acrylate, 20 parts of 2-hydroxyethyl acrylate, 0.5 part of 1-hydroxycyclohexyl benzophenone and 0.2 part of a molecular weight control agent dodecyl mercaptan.
The preparation method of the OCA optical cement comprises the following steps:
the method comprises the following steps: mixing 65 parts of 2-ethylhexyl acrylate, 14.5 parts of isobornyl acrylate, 20 parts of 2-hydroxyethyl acrylate, 0.5 part of 1-hydroxycyclohexyl benzophenone and 0.2 part of dodecanethiol to obtain a monomer prepolymer;
step two: adding 11732-hydroxy-2-methyl-1-phenyl acetone and a multifunctional crosslinking agent into the monomer prepolymer obtained in the step one under the protection of nitrogen by exposing to ultraviolet radiation to partially polymerize the monomer prepolymer, thereby obtaining a prepolymer with the viscosity of about 300-10000 centipoises.
On the basis, the molecular weight of the monomer prepolymer is controllable, so that different OCA optical adhesives can be manufactured according to different requirements.
On the basis of the above, the molecular weight of the monomer prepolymer can be controlled by changing the fraction of the molecular weight controlling agent.
The application of the OCA optical cement comprises a preparation method of the OCA optical cement, and further comprises the following steps:
step A: unreeling the release film;
and B: uniformly coating the obtained OCA optical cement on the unreeled release film in the step A to obtain the release film coated with the OCA optical cement;
and C: placing the release film coated with the OCA optical adhesive in the step B under illumination for curing to obtain a cured optical adhesive film;
step D: and C, rolling the cured optical adhesive film obtained in the step C.
In the polymerization reaction process, according to the parts of the mixture molecular weight control agent, the molecular weights of different acrylate monomer polymers can be obtained, and the experimental data of the molecular weights are as follows:
molecular weight controlling agent (parts) Molecular weight
0 200W
0.1 110W
0.15 50W
0.2 30W
0.3 8W
0.5 7W
Example two:
the OCA optical cement comprises 45 parts of 2-ethylhexyl acrylate, 30 parts of isobornyl acrylate, 24.2 parts of 2-hydroxyethyl acrylate and 0.1 part of 1-hydroxycyclohexyl benzophenone.
The preparation method of the OCA optical cement comprises the following steps:
the method comprises the following steps: mixing 45 parts of 2-ethylhexyl acrylate, 30 parts of isobornyl acrylate, 24.2 parts of 2-hydroxyethyl acrylate and 0.1 part of 1-hydroxycyclohexyl benzophenone to obtain a monomer prepolymer;
step two: and (3) adding the 1841-hydroxycyclohexyl phenyl ketone photoinitiator and the trifunctional crosslinking agent into the monomer prepolymer obtained in the step one by exposing the monomer prepolymer to ultraviolet radiation in a nitrogen protection environment to enable the monomer prepolymer to be partially polymerized, and stopping the reaction by turning off the ultraviolet after the temperature of the mixture is increased by 10 ℃ during the polymerization reaction, thereby obtaining the prepolymer with the viscosity of about 300-10000 centipoises.
On the basis, the molecular weight of the monomer prepolymer is controllable, so that different OCA optical adhesives can be manufactured according to different requirements.
On the basis of the above, the molecular weight of the monomer prepolymer can be controlled by changing the ultraviolet energy intensity.
The application of the OCA optical cement comprises a preparation method of the OCA optical cement, and further comprises the following steps:
step A: unreeling the release film;
and B: uniformly coating the obtained OCA optical cement on the unreeled release film in the step A to obtain the release film coated with the OCA optical cement;
and C: placing the release film coated with the OCA optical adhesive in the step B under illumination for curing to obtain a cured optical adhesive film;
step D: and C, rolling the cured optical adhesive film obtained in the step C.
The experimental data of the ultraviolet energy intensity and the molecular weight are as follows:
intensity of irradiated ultraviolet energy (mw/cm)2) Molecular weight
0.3 180W
1 170W
4 150W
10 120W
50 90W
100 65W
Example three: the OCA optical adhesive comprises 80 parts of 2-ethylhexyl acrylate, 10 parts of isobornyl acrylate, 9.8 parts of 2-hydroxyethyl acrylate, 0.2 part of 1-hydroxycyclohexyl benzophenone and 1 part of a molecular weight control agent dodecyl mercaptan.
The preparation method of the OCA optical cement comprises the following steps:
the method comprises the following steps: mixing 80 parts of 2-ethylhexyl acrylate, 10 parts of isobornyl acrylate, 9.8 parts of 2-hydroxyethyl acrylate, 0.2 part of 1-hydroxycyclohexyl benzophenone and 1 part of dodecanethiol to obtain a monomer prepolymer;
step two: exposing the monomer prepolymer obtained in the step one to the atmosphere protected by nitrogen to the strength of 0.8mw/cm2The monomer prepolymer was partially polymerized by UV irradiation with 1841-hydroxycyclohexyl phenyl ketone photoinitiator and a trifunctional crosslinker, by varying the fraction of photoinitiator during the polymerization, to give a prepolymer having a viscosity of about 300 and 10000 centipoise.
On the basis, the molecular weight of the monomer prepolymer is controllable, so that different OCA optical adhesives can be manufactured according to different requirements.
On the basis of the above, the molecular weight of the monomer prepolymer can be controlled by changing the fraction of the photoinitiator.
The application of the OCA optical cement comprises a preparation method of the OCA optical cement, and further comprises the following steps:
step A: unreeling the release film;
and B: uniformly coating the obtained OCA optical cement on the unreeled release film in the step A to obtain the release film coated with the OCA optical cement;
and C: placing the release film coated with the OCA optical adhesive in the step B under illumination for curing to obtain a cured optical adhesive film;
step D: and C, rolling the cured optical adhesive film obtained in the step C.
The experimental data for photoinitiator fraction and molecular weight are as follows:
photoinitiator (parts) Molecular weight
0.01 320W
0.1 110W
0.5 68W
1 47W
1.5 28W
2 16W
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention, and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (6)

1. An OCA optical cement, which is characterized in that: including 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone, and a molecular weight control agent, dodecyl mercaptan.
2. An OCA optical cement as claimed in claim 1, wherein: the part range of the acrylic acid-2-ethylhexyl ester is 30-95, the part range of the acrylic acid isobornyl ester is 0-50, the part range of the 2-hydroxyethyl acrylate is 0-30, the part range of the 1-hydroxycyclohexyl benzophenone is 0.01-1, and the part range of the molecular weight control agent dodecyl mercaptan is 0-2.
The preparation method of the OCA optical cement is characterized by comprising the following steps: an OCA optical cement comprising the OCA optical cement of claims 1-2, further comprising the steps of:
the method comprises the following steps: mixing 2-ethylhexyl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 1-hydroxycyclohexyl benzophenone and dodecyl mercaptan to obtain a monomer prepolymer;
step two: and (3) adding a photoinitiator and a crosslinking agent into the monomer prepolymer obtained in the step one by exposing to ultraviolet radiation under the environment of nitrogen protection to obtain the OCA optical adhesive.
4. The method of claim 3, wherein the OCA optical cement comprises: the molecular weight of the monomer prepolymer is controllable.
5. The method of claim 3, wherein the OCA optical cement comprises: the molecular weight of the monomer prepolymer can be controlled by varying the ultraviolet energy intensity, varying the fraction of photoinitiator, or varying the fraction of molecular weight controlling agent.
The application of the OCA optical cement is characterized in that: a method of making an OCA optical cement comprising the steps of claims 3-5, further comprising the steps of:
step A: unreeling the release film;
and B: uniformly coating the OCA optical cement obtained in the claim 3 on the unreeled release film in the step A to obtain the release film coated with the OCA optical cement;
and C: placing the release film coated with the OCA optical adhesive in the step B under illumination for curing to obtain a cured optical adhesive film;
step D: and C, rolling the cured optical adhesive film obtained in the step C.
CN202011083404.3A 2020-10-12 2020-10-12 OCA optical cement, preparation method and application thereof Pending CN112210327A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114539953A (en) * 2022-03-28 2022-05-27 中山市长浩合成科技有限公司 OCA glue and preparation method and application thereof
CN115368832A (en) * 2022-09-13 2022-11-22 苏州科丽尔光电材料有限公司 Mini LED packaging adhesive film and preparation method thereof

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114539953A (en) * 2022-03-28 2022-05-27 中山市长浩合成科技有限公司 OCA glue and preparation method and application thereof
CN115368832A (en) * 2022-09-13 2022-11-22 苏州科丽尔光电材料有限公司 Mini LED packaging adhesive film and preparation method thereof

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Application publication date: 20210112