CN118005837A - Low-temperature-response acrylic ester copolymer, adhesive, optical film and preparation method and application thereof - Google Patents

Low-temperature-response acrylic ester copolymer, adhesive, optical film and preparation method and application thereof Download PDF

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Publication number
CN118005837A
CN118005837A CN202410417534.8A CN202410417534A CN118005837A CN 118005837 A CN118005837 A CN 118005837A CN 202410417534 A CN202410417534 A CN 202410417534A CN 118005837 A CN118005837 A CN 118005837A
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adhesive
acrylate
low temperature
acrylic ester
temperature
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CN118005837B (en
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刘俏
张琴
陈磊
黎永铭
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Guangzhou Huigu Functional Materials Co ltd
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Guangzhou Huigu Functional Materials Co ltd
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    • 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
    • C08F220/1804C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (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
    • 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
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062Copolymers with monomers not covered by C09J133/06
    • C09J133/066Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • 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
    • C09J7/30Adhesives in the form of films or foils characterised by the adhesive composition
    • 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
    • C09J2433/00Presence of (meth)acrylic polymer

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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)

Abstract

The invention discloses a low-temperature-response acrylic ester copolymer, an adhesive, an optical film, a preparation method and application. The acrylate copolymer provided by the invention has the characteristics of 20-35 ten thousand weight average molecular weight, glass transition temperature of-10-0 ℃ and hydroxyl value of 100-101 mgKOH/g. The adhesive containing the acrylic ester copolymer and the optical film can achieve the effect of losing adhesion after being subjected to low-temperature treatment, so that the adhesive can be separated from the flexible touch film, the problem that the adhesive is easy to foam back in the production process is solved, and the adhesive can be easily removed from the surface of an adherend under the condition of no solvent, thereby saving cost, protecting environment and improving efficiency.

Description

Low-temperature-response acrylic ester copolymer, adhesive, optical film and preparation method and application thereof
Technical Field
The invention belongs to the technical field of adhesives, and particularly relates to a low-temperature-response acrylic ester copolymer, an adhesive, an optical film, a preparation method and application.
Background
The temperature control adhesive is a novel functional adhesive film which can be subjected to adhesion-stripping control along with temperature change, and is mainly applied to process protection and auxiliary materials for producing flexible touch films. When the adhesive is used as an auxiliary material for producing the flexible touch film, the adhesive is required to have better optical performance so as to observe the change of the flexible touch film during production, and meanwhile, the adhesive is required to have certain viscosity under the initial fitting condition, so that the adhesive is ensured to be fixed in a series of environmental changes in the production process of the flexible touch film; in order to separate the flexible touch control film from the temperature control adhesive with a fixing function after the production of the flexible touch control film is finished, the flexible touch control film needs to be subjected to high temperature (120 ℃) in the production process, so that the flexible touch control film is required to be free of adhesive residue at high temperature, meanwhile, the temperature control adhesive left on the carrier plate can be removed from the carrier plate under the condition of no need of cleaning by means of a solvent, so that efficient continuous production is achieved, the temperature control adhesive is required to have a good low-temperature adhesion loss effect, the adhesive film has certain strength after the low-temperature treatment, and certain high-temperature resistance is required, and the adhesive residue is avoided at high temperature.
In the prior art, the need for such products is generally achieved by adjusting the Tg (glass transition temperature) of the adhesive to achieve its effect of tack-free at low temperatures. However, the simple adjustment of Tg cannot solve the following problems, such as the fact that the flexible touch film is not separated from the temperature control adhesive, the temperature control adhesive remains on the carrier plate and cannot be peeled off, and the foam is easy to return in the production process.
Therefore, it is necessary to develop an adhesive and a temperature-controlling adhesive that can solve the above problems.
Disclosure of Invention
The primary object of the present invention is to overcome the disadvantages and shortcomings of the prior art and to provide a low temperature responsive acrylate copolymer.
Another object of the present invention is to provide an adhesive for low temperature response, comprising the above-mentioned low temperature response acrylate copolymer.
It is still another object of the present invention to provide an optical film for low temperature response, and a method for preparing the same and application thereof.
The aim of the invention is achieved by the following technical scheme:
A low temperature responsive acrylate copolymer having the following characteristics: the weight average molecular weight is 20-35 ten thousand, the glass transition temperature (Tg) is-10-0 ℃ and the hydroxyl value is 100-101 mgKOH/g; preferably has the following characteristics: the weight average molecular weight is 20-30 ten thousand, the glass transition temperature (Tg) is-7 ℃ to-4 ℃ and the hydroxyl value is 100-101 mgKOH/g; more preferably, the method has the following characteristics: the weight average molecular weight is 20-30 ten thousand, the glass transition temperature (Tg) is-6.4 ℃ to-4.2 ℃ and the hydroxyl value is 100.1-100.3 mgKOH/g.
The Tg of the low temperature responsive acrylate copolymer can be controlled by acrylate monomers in the main structure, wherein the acrylate monomers comprise acrylate soft monomers, acrylate hard monomers and acrylate functional monomers.
The acrylic ester soft monomer refers to an acrylic ester monomer with a glass transition temperature lower than 0 ℃.
The hard acrylate monomer refers to an acrylate monomer with a glass transition temperature higher than 0 ℃.
The acrylate functional monomer refers to an acrylate monomer containing a special functional group.
The acrylate copolymer preferably comprises the following components in parts by weight: 100 parts of acrylate monomer, 0.2-0.4 part of initiator and 0.004-0.04 part of chain transfer agent.
The acrylate copolymer further includes an organic solvent as a reaction medium for dispersing the reaction raw materials, thereby facilitating the progress of the reaction.
The dosage of the organic solvent is preferably 50-200 parts by mass; more preferably 80 to 120 parts by mass.
The organic solvent is at least one of ketone and esters.
The ketone is preferably at least one of butanone and methyl isobutyl ketone.
The ester is preferably at least one of ethyl acetate and butyl acetate.
In the acrylic ester monomer, the acrylic ester soft monomer accounts for 45-55% by mass, the acrylic ester hard monomer accounts for 25-35% by mass, and the acrylic ester functional monomer accounts for the rest; preferably, in the acrylate monomer, the acrylate soft monomer accounts for 48-52% by mass, the acrylate hard monomer accounts for 27-31% by mass, and the acrylate functional monomer accounts for the balance.
The acrylic ester soft monomer is preferably at least one of ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate and lauryl acrylate; more preferably a combination of butyl acrylate and 2-ethylhexyl acrylate; most preferably, the compound is prepared by mixing butyl acrylate and 2-ethylhexyl acrylate according to a mass ratio of 38-42:10.
The acrylate hard monomer is preferably at least one of methyl acrylate, methyl methacrylate, isobornyl methacrylate and cyclohexyl methacrylate.
The acrylate functional monomer is preferably at least one of acrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate and hydroxybutyl acrylate.
The initiator is at least one selected from azodiisobutyronitrile, azodiisoheptonitrile, azodiisovaleronitrile, dimethyl azodiisobutyrate, dibenzoyl peroxide and tert-butyl peroxy-2-ethylhexanoate;
the chain transfer agent is preferably at least one of n-dodecyl mercaptan, tert-dodecyl mercaptan and n-octyl mercaptan.
The preparation method of the acrylic ester copolymer with low temperature response comprises the following steps: in an organic solvent medium, polymerizing an acrylic ester soft monomer, an acrylic ester hard monomer, an acrylic ester functional monomer and a chain transfer agent under the action of an initiator to obtain the polymer; preferably comprises the following specific steps:
(1) Uniformly mixing an acrylic ester soft monomer, an acrylic ester hard monomer, an acrylic ester functional monomer and a chain transfer agent to obtain a mixture;
(2) Uniformly mixing part of the mixture obtained in the step (1) with an organic solvent, and preserving heat at 70-90 ℃ in a nitrogen atmosphere;
(3) Then adding an initiator, and reacting at 70-90 ℃ in a nitrogen atmosphere;
(4) Uniformly mixing the rest part of the mixture obtained in the step (1) with an initiator to obtain a mixed solution; dropwise adding the mixed solution into the heat-preserving reaction system in the step (3), and continuing the heat-preserving reaction after the dropwise adding;
(5) Then adding an initiator, and carrying out heat preservation reaction at 70-90 ℃ in a nitrogen atmosphere to obtain the low-temperature-response acrylic ester copolymer.
The portion described in step (2) is preferably 1/2 to 2/3.
The time of heat preservation in the step (2) is preferably 10-30 min; more preferably 15min.
The initiator in the step (3) is preferably used in an amount of 0.10 to 0.15% of the total mass of the monomers; more preferably 0.13% of the total mass of the monomers.
The time of the heat preservation reaction in the step (3) is preferably 20-40 min; more preferably 30min.
The initiator in the step (4) is preferably used in an amount of 0.15 to 0.25% of the total mass of the monomers; more preferably 0.20% of the total mass of the monomers.
The time of dripping in the step (4) is preferably 2-4 hours; more preferably 3h.
The time of the heat preservation reaction in the step (4) is preferably 60-120 min; more preferably 90min.
The initiator in the step (5) is preferably used in an amount of 0.05 to 0.10% of the total mass of the monomers; more preferably 0.07% of the total mass of the monomers.
The time of the heat preservation reaction in the step (5) is preferably 2-4 hours; more preferably 3h.
The application of the low-temperature-response acrylic ester copolymer in preparing the low-temperature-response adhesive.
The adhesive with low temperature response comprises the following components in parts by weight: 100 parts of the low-temperature-response acrylic ester copolymer and 1-2 parts of a cross-linking agent; the composition preferably comprises the following components in parts by weight: 100 parts of low-temperature response acrylate copolymer and 1.5 parts of cross-linking agent.
The adhesive with low temperature response also comprises an organic solvent; the organic solvent is used for diluting the crosslinking agent and adjusting the viscosity so as to improve the workability of the adhesive.
The dosage of the organic solvent is preferably 10-20 parts by mass; more preferably 12 parts by mass.
The organic solvent is at least one of ketone and ester.
The ketone is preferably at least one of butanone and methyl isobutyl ketone.
The ester is preferably at least one of ethyl acetate and butyl acetate.
The cross-linking agent is a compound containing 2-3 functional reactive groups; preferably at least one of isophorone diisocyanate (IPDI), toluene Diisocyanate (TDI), 1, 4-cyclohexane isocyanate (CHDI), xylylene Diisocyanate (XDI), tetramethyl isophthalene diisocyanate (TMXDI), cyclohexane dimethylene diisocyanate (HXDI), trimethyl-1, 6-hexamethylene diisocyanate (TMHDI), hexamethylene Diisocyanate (HDI), HDI trimer, TDI trimer, IPDI trimer, XDI trimer; more preferably at least one of HDI trimer (e.g., bayer N3390, rhodia HDT-90B, degussa HT 2500L) and TDI trimer (e.g., bayer L75).
The preparation method of the adhesive with low temperature response comprises the following steps: and uniformly mixing the acrylic ester copolymer, the cross-linking agent and the organic solvent to obtain the adhesive with low-temperature response.
The application of the adhesive with low temperature response in the preparation of the optical film.
A low-temperature-response optical film contains the low-temperature-response adhesive.
The preparation method of the optical film with low temperature response comprises the following steps: coating and drying the adhesive with low temperature response to obtain an optical film with low temperature response; more preferably, the preparation is carried out by the following steps: and coating the adhesive with the low temperature response on a substrate, drying and curing to obtain the optical film with the low temperature response.
The coating method can be a Slot Die, a Micro-gram, a reverse roll coating method, a doctor blade method, a spin coating method and the like.
The substrate is preferably a PET substrate.
The thickness of the base material is preferably 30-100 mu m; more preferably 50 to 75. Mu.m.
The drying temperature is preferably 50-110 ℃; more preferably 70 to 100 ℃.
The curing conditions are preferably as follows: placing for 12-28 h at 35-60 ℃; more preferably: placing for 24 hours at 50-60 ℃.
The thickness of the optical film is preferably 25-200 mu m; more preferably 50 to 100. Mu.m.
The application of the optical film in preparing the flexible touch film is used for fixing the flexible touch film during production.
Compared with the prior art, the invention has the following advantages and effects:
The adhesive for the temperature control adhesive provided by the invention has the advantages that the chain segment of the acrylic ester copolymer is designed and controlled, and the weight average molecular weight is as follows: 20-35 ten thousand glass transition temperature Tg: the temperature of between 10 ℃ below zero and 0 ℃ below zero, so that the viscosity loss effect can be achieved after the low-temperature treatment, and the separation of the flexible touch membrane and the flexible touch membrane can be realized; meanwhile, a large amount of acrylate monomers containing hydroxyl are introduced into a main structure of the copolymer through a special synthesis process, so that the distribution density of the hydroxyl is higher, and after the acrylate monomers react with a cross-linking agent, a compact structure is formed, so that the acrylate monomers have more and smaller bonding anchor points, the problem that the acrylate monomers are easy to foam back in the production process is solved, and the acrylate monomers are easy to remove from the surface of an adherend under the condition of no solvent, so that the cost is saved, the environment is protected, and the efficiency is improved.
Detailed Description
The present invention will be described in further detail with reference to examples, but embodiments of the present invention are not limited thereto.
The materials referred to in the examples below are all commercially available.
The preparation method of the acrylate copolymer is a conventional free radical copolymerization method, and resins with different Tg and hydroxyl values are synthesized by adding hydroxyl-containing acrylate monomers with different mass parts by adjusting the proportion of soft and hard monomers. The following is one of the preparation methods, but not the only preparation method, and other methods for obtaining the target structure of the copolymer of the present invention are all the methods that can be realized by the present invention.
Preparation example
(1) The preparation method of the acrylic ester copolymer comprises the following steps:
S1: uniformly mixing Butyl Acrylate (BA), 2-ethylhexyl acrylate (2-EHA), methyl Methacrylate (MMA), hydroxyethyl acrylate (also known as 2-hydroxyethyl acrylate, HEA) and dodecyl mercaptan to obtain a mixture; wherein the total mass of the monomers is 100g;
S2: adding 2/3 of the total mass of the mixture obtained in the step S1 and 100g of ethyl acetate into a reaction kettle, introducing nitrogen, heating to 80 ℃, and preserving heat for 15 minutes;
S3: 0.13g of Azodiisobutyronitrile (AIBN) is added, evenly mixed and reacted for 30 minutes at 80 ℃;
S4: dropwise adding a mixed solution formed by the residual mixture prepared in the step S1 and 0.2g of AIBN for 3 hours, and preserving heat for reaction for 1.5 hours after the completion of dropwise adding;
S5: 0.07g AIBN solution is added, and the temperature is kept for 3 hours to obtain the acrylic ester copolymer.
(2) Preparation of temperature-control adhesive
100G of the acrylic ester copolymer prepared in the step (1), 1.5g of a cross-linking agent (Bayer L75) and 12g of ethyl acetate are uniformly mixed, stirred, dispersed, defoamed and filtered, the mixture is coated on a PET heavy release film with the thickness of 50 mu m by using a coater, and the mixture is dried for 3 minutes at the temperature of 100 ℃, and is covered with a light release film, so that the dry glue thickness is 50 mu m, and the temperature-control glue is obtained.
Examples 1 to 3 and comparative examples 1 to 6: using the above copolymer preparation method, the raw materials in Table 1 were prepared according to the step (1) to obtain an acrylic ester copolymer, and the corresponding acrylic ester copolymer was obtained. And then preparing the copolymers obtained in examples 1-3 and comparative examples 1-5 according to the step (2) to obtain the temperature-control adhesive.
Table 1: the proportions and amounts (parts by mass) of the respective material components in examples and comparative examples
Wherein the weight average molecular weight is measured by Gel Permeation Chromatography (GPC);
the glass transition temperature (Tg) is measured by a Differential Scanning Calorimeter (DSC);
The hydroxyl number was determined by titration.
Effect examples
1. Test of the properties of the adhesives for temperature-controlled adhesives prepared in examples 1 to 3 and comparative examples 1 to 5
Performance test: the overall performance of the temperature-controlled glue layers prepared from the glues of examples 1 to 3 and comparative examples 1 to 5 were evaluated, wherein:
the method for detecting the thickness of the adhesive film is shown in GB/T7125-1986.
The tensile strength is measured in GB/T30776-2014.
The light transmittance was measured by the method described in JIS K-7105.
Haze was measured according to JIS K-7105.
The peel force was measured as described in GB/T2792-1998.
The retention force is measured as described in GB/T4851-1998.
The method for detecting the annular initial adhesion is disclosed in GB/T31125-2014.
The simulation test method for the bonding bubbles and the production process of returning bubbles is as follows:
And (3) attaching air bubbles: a temperature-controlled adhesive sample with the size of 90mm multiplied by 150mm is taken, reinforced by 50 mu m PET, then is attached to glass by a counter-adhesive machine at the speed of 3m/min under the pressure of 0.1MPa, and whether foaming exists or not is observed after the attachment is finished.
And (3) returning bubbles: and (3) placing the bonded materials in an environment of-0.1 MPa and 120 ℃ for 4 hours, taking out the bonded materials, and comparing whether the bonded materials return to bubbles.
The low temperature removal application simulation test method is as follows:
Taking a temperature control adhesive sample with the size of 160mm multiplied by 210mm, peeling off a light release film, reinforcing with 50 mu m PET, attaching on glass at normal temperature, standing at 120 ℃ for 4 hours, taking out, standing to normal temperature, taking out after standing at-5 ℃ for 5 minutes, picking up the reinforcing film from a small corner by a knife, wherein the reinforcing film can be easily separated from an adhesive block, and the adhesive can be removed from the surface of the glass to be qualified.
The performance results of examples 1 to 3 and comparative examples 1 to 5 are shown in Table 2.
Table 2 evaluation of temperature-controlled glue layer Performance
As can be seen from the performance data in examples 1-3 in Table 1, the adhesive layer prepared by using the structural acrylate copolymer and the crosslinking agent, and the adhesives prepared by selecting the preferred components in different proportions, has little difference in performance, and can meet the production line requirements.
Comparative examples 1 to 5 are respectively compared with the temperature-controlled adhesive properties prepared by the acrylate copolymer with a specific structure according to the invention in terms of hydroxyl value, tg and molecular weight, and it can be found that when the molecular weight is too large or too small, tg is lower or higher, the low-temperature removal performance is not qualified, and in addition, defects such as lamination bubbles can occur in the lamination process; when the hydroxyl value is lower, bubbles can be generated during bonding due to insufficient bonding anchor points, and the bubbles can be returned in the process.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.

Claims (10)

1. An acrylic acid ester copolymer having a low temperature response, characterized by the following features: the weight average molecular weight is 20-35 ten thousand, the glass transition temperature is-10-0 ℃ and the hydroxyl value is 100-101 mgKOH/g.
2. The low temperature responsive acrylate copolymer according to claim 1, characterized by comprising the following components in parts by mass: 100 parts of acrylic ester monomer, 0.2 to 0.4 part of initiator and 0.004 to 0.04 part of chain transfer agent;
in the acrylic ester monomer, the acrylic ester soft monomer accounts for 45-55% by mass, the acrylic ester hard monomer accounts for 25-35% by mass, and the acrylic ester functional monomer accounts for the rest;
The acrylic ester soft monomer is a compound prepared by mixing butyl acrylate and 2-ethylhexyl acrylate according to a mass ratio of 38-42:10.
3. The low temperature responsive acrylate copolymer according to claim 2 wherein: also comprises an organic solvent.
4. A low temperature responsive acrylate copolymer according to claim 2 or 3, characterized in that:
The acrylate hard monomer is at least one of methyl acrylate, methyl methacrylate, isobornyl methacrylate and cyclohexyl methacrylate;
The acrylate functional monomer is at least one of acrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate and hydroxybutyl acrylate;
The initiator is at least one of azodiisobutyronitrile, azodiisoheptonitrile, azodiisovaleronitrile, dimethyl azodiisobutyrate, dibenzoyl peroxide and tert-butyl peroxy-2-ethylhexanoate;
the chain transfer agent is at least one of n-dodecyl mercaptan, tert-dodecyl mercaptan and n-octyl mercaptan.
5. The adhesive with low temperature response is characterized by comprising the following components in parts by weight: the low temperature-responsive acrylic acid ester copolymer according to any one of claims 1 to 4, wherein the acrylic acid ester copolymer comprises 100 parts of a low temperature-responsive acrylic acid ester copolymer and 1 to 2 parts of a crosslinking agent.
6. The low temperature responsive adhesive of claim 5, wherein: also comprises an organic solvent.
7. The low temperature responsive adhesive of claim 5 or 6, wherein:
The cross-linking agent is at least one of isophorone diisocyanate, toluene diisocyanate, 1, 4-cyclohexane isocyanate, xylylene diisocyanate, tetramethyl m-xylylene diisocyanate, cyclohexane dimethylene diisocyanate, trimethyl-1, 6-hexamethylene diisocyanate, HDI trimer, TDI trimer, IPDI trimer and XDI trimer.
8. An optical film having a low temperature response, characterized by: an adhesive comprising the low temperature response of any one of claims 5 to 7.
9. The method for producing a low-temperature-responsive optical film according to claim 8, comprising the steps of: coating and drying the adhesive with low temperature response according to claim 8 to obtain the optical film with low temperature response.
10. Use of the optical film of claim 8 in the preparation of a flexible touch film.
CN202410417534.8A 2024-04-09 2024-04-09 Low-temperature-response acrylic ester copolymer, adhesive, optical film and preparation method and application thereof Active CN118005837B (en)

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Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102732176A (en) * 2012-07-06 2012-10-17 中国航空工业集团公司北京航空材料研究院 Peelable polyacrylate pressure-sensitive adhesive film with controllable peeling force
US20130211028A1 (en) * 2010-08-19 2013-08-15 Daido Chemical Corporation Acrylic polymer for use in pressure-sensitive adhesive composition for touch screen panel
TWI424037B (en) * 2005-06-20 2014-01-21 Toyo Ink Mfg Co Solvent-based antistatic acrylic pressure sensitive adhesive agent for optical element and protective film for optical element
JP2018053145A (en) * 2016-09-29 2018-04-05 東洋インキScホールディングス株式会社 Pressure sensitive adhesive, pressure sensitive adhesive film and optical laminate
CN108350332A (en) * 2015-12-28 2018-07-31 综研化学株式会社 Adhesive composition, adhesive phase and surface protective plate
CN108641620A (en) * 2018-03-28 2018-10-12 广州慧谷工程材料有限公司 A kind of pressure sensitive adhesive and its application process being used for imagery optical component, touch panel, display device
US20190077134A1 (en) * 2015-09-25 2019-03-14 Toyo Ink Sc Holdings Co., Ltd. Decorative film and method for producing same, and decorated molded article
CN111196912A (en) * 2018-11-16 2020-05-26 日本电石工业株式会社 Adhesive composition for optical member protective film and optical member protective film
CN114015388A (en) * 2021-12-20 2022-02-08 苏州赛伍应用技术股份有限公司 Hydroxyl-containing viscose reducing agent composition and preparation method and application thereof
CN115926690A (en) * 2022-11-29 2023-04-07 苏州赛伍应用技术股份有限公司 Viscosity-reducing adhesive composition, viscosity-reducing adhesive tape and preparation method thereof
CN116355559A (en) * 2021-12-28 2023-06-30 南京清尚新材料科技有限公司 Pressure-sensitive adhesive and adhesive sheet for low-temperature peeling and method for producing the same
CN116875228A (en) * 2023-07-31 2023-10-13 派乐玛光学薄膜(东莞)有限公司 Environment-friendly ultraviolet-resistant OCA optical cement and preparation method thereof
CN117511456A (en) * 2023-11-14 2024-02-06 中山大学 Acrylate-based microsphere pressure-sensitive adhesive and preparation method and application thereof
CN117777896A (en) * 2023-12-27 2024-03-29 苏州赛伍应用技术股份有限公司 Adhesive composition and preparation method and application thereof

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI424037B (en) * 2005-06-20 2014-01-21 Toyo Ink Mfg Co Solvent-based antistatic acrylic pressure sensitive adhesive agent for optical element and protective film for optical element
US20130211028A1 (en) * 2010-08-19 2013-08-15 Daido Chemical Corporation Acrylic polymer for use in pressure-sensitive adhesive composition for touch screen panel
CN102732176A (en) * 2012-07-06 2012-10-17 中国航空工业集团公司北京航空材料研究院 Peelable polyacrylate pressure-sensitive adhesive film with controllable peeling force
US20190077134A1 (en) * 2015-09-25 2019-03-14 Toyo Ink Sc Holdings Co., Ltd. Decorative film and method for producing same, and decorated molded article
CN108350332A (en) * 2015-12-28 2018-07-31 综研化学株式会社 Adhesive composition, adhesive phase and surface protective plate
JP2018053145A (en) * 2016-09-29 2018-04-05 東洋インキScホールディングス株式会社 Pressure sensitive adhesive, pressure sensitive adhesive film and optical laminate
CN108641620A (en) * 2018-03-28 2018-10-12 广州慧谷工程材料有限公司 A kind of pressure sensitive adhesive and its application process being used for imagery optical component, touch panel, display device
CN111196912A (en) * 2018-11-16 2020-05-26 日本电石工业株式会社 Adhesive composition for optical member protective film and optical member protective film
CN114015388A (en) * 2021-12-20 2022-02-08 苏州赛伍应用技术股份有限公司 Hydroxyl-containing viscose reducing agent composition and preparation method and application thereof
CN116355559A (en) * 2021-12-28 2023-06-30 南京清尚新材料科技有限公司 Pressure-sensitive adhesive and adhesive sheet for low-temperature peeling and method for producing the same
CN115926690A (en) * 2022-11-29 2023-04-07 苏州赛伍应用技术股份有限公司 Viscosity-reducing adhesive composition, viscosity-reducing adhesive tape and preparation method thereof
CN116875228A (en) * 2023-07-31 2023-10-13 派乐玛光学薄膜(东莞)有限公司 Environment-friendly ultraviolet-resistant OCA optical cement and preparation method thereof
CN117511456A (en) * 2023-11-14 2024-02-06 中山大学 Acrylate-based microsphere pressure-sensitive adhesive and preparation method and application thereof
CN117777896A (en) * 2023-12-27 2024-03-29 苏州赛伍应用技术股份有限公司 Adhesive composition and preparation method and application thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
文智霞等: "水性丙烯酸酯复膜胶的制备", 中国胶粘剂, vol. 26, no. 04, 30 April 2017 (2017-04-30), pages 45 - 49 *
石亮等: "聚氨酯丙烯酸酯涂料的性能研究", 涂料工业, vol. 40, no. 03, 31 March 2010 (2010-03-31), pages 36 - 40 *
罗春晖等: "水性双组分涂料用丙烯酸酯乳液的羟值因素", 涂料工业, vol. 39, no. 10, 31 October 2009 (2009-10-31), pages 36 - 40 *

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