CN115627135A - Multifunctional UV viscosity-reducing composition and preparation method and application thereof - Google Patents

Multifunctional UV viscosity-reducing composition and preparation method and application thereof Download PDF

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Publication number
CN115627135A
CN115627135A CN202211377832.6A CN202211377832A CN115627135A CN 115627135 A CN115627135 A CN 115627135A CN 202211377832 A CN202211377832 A CN 202211377832A CN 115627135 A CN115627135 A CN 115627135A
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multifunctional
acrylate
polymer
composition
parts
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汪义方
曹又文
岳威
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Suzhou Gaotai Electronic Technology Co ltd
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Suzhou Gaotai Electronic Technology Co ltd
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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
    • 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
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
    • C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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
    • C09J2467/00—Presence of polyester

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (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 multifunctional UV visbreaking composition which comprises, by weight, 100 parts of solvent type acrylate polymer, 25-75 parts of macromolecular polymer of a multi-photosensitive group, 0.05-5 parts of curing agent, 1-5 parts of photoinitiator and solvent, wherein the macromolecular polymer of the multi-photosensitive group is a (methyl) acrylate polymer with a side group containing carbon-carbon double bonds, and the weight-average molecular weight of the macromolecular polymer is 8-50 ten thousand. The invention also discloses a preparation method of the multifunctional UV viscosity-reducing composition and a UV viscosity-reducing adhesive tape. The multifunctional UV viscosity-reducing composition disclosed by the invention adopts the two-component collocation, so that the condition that the number of photosensitive groups is limited by the number of polar groups on an acrylic main chain is avoided, and more preparation space is provided for use; meanwhile, as the additive component is macromolecule, after the coating film is formed, the macromolecule chains are wound, so that the adhesive has stronger cohesion and is not easy to have adhesive residue.

Description

Multifunctional UV viscosity-reducing composition and preparation method and application thereof
Technical Field
The invention relates to the technical field of adhesives, in particular to a multifunctional UV (ultraviolet) viscosity-reducing composition and a preparation method and application thereof.
Background
The existing UV viscosity reducing adhesives can be roughly classified into two types, one is to modify the main chain of the existing acrylic adhesive so that the side group has a large number of (meth) acrylate photosensitive groups, and since the reaction needs to consume a large number of polar groups such as hydroxyl groups and amino groups on the acrylic main chain, the viscosity of the finally prepared UV viscosity reducing adhesive is greatly reduced compared with that of the original acrylic adhesive before UV irradiation. Meanwhile, the number of the photosensitive groups is limited by the number of the polar groups on the acrylic main chain, so that the adjustable peeling force range after UV is further limited.
The other is to add a multifunctional UV viscosity-reducing composition into the main component of the existing acrylic adhesive. Although the limitation of the number of polar groups on the acrylic main chain is avoided, the added multifunctional UV viscosity-reducing composition on the market generally has a small molecular weight, and when a peeling force test before UV irradiation is carried out, the possibility of adhesive residue is extremely high, which also causes a certain degree of doubt to many users.
Disclosure of Invention
The invention aims to solve the technical problem of providing a multifunctional UV viscosity-reducing composition, wherein the viscosity-reducing composition avoids the condition that the number of photosensitive groups is limited by the number of polar groups on an acrylic main chain by matching two components, and provides more preparation space for use; meanwhile, as the additive component is macromolecule, after the coating film is formed, the macromolecule chains are wound, so that the adhesive has stronger cohesion and is not easy to have adhesive residue.
In order to solve the technical problems, the invention provides the following technical scheme:
in a first aspect, the invention provides a multifunctional UV viscosity-reducing composition, which comprises, by weight, 100 parts of a solvent-based acrylate polymer, 25-75 parts of a multi-photosensitive group macromolecular polymer, 0.05-5 parts of a curing agent, 1-5 parts of a photoinitiator and a solvent, wherein the multi-photosensitive group macromolecular polymer is a (methyl) acrylate polymer with a side group containing a carbon-carbon double bond, and the weight-average molecular weight of the multi-photosensitive group macromolecular polymer is 8-50 ten thousand.
Further, the macromolecular polymer of the poly-sensitive group is obtained by the reaction of (methyl) acrylic ester polymer containing hydroxyl and (methyl) acrylic ester monomer containing isocyanate group; wherein the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 5-30 ten thousand.
Further, the hydroxyl-containing (meth) acrylate polymer is obtained by polymerizing a (meth) acrylate monomer with a hydroxyl group on a side group, wherein the (meth) acrylate monomer with a hydroxyl group on a side group comprises one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate.
Further, the isocyanate group-containing (meth) acrylate monomer includes at least one of isocyanoethyl acrylate and isocyanoethyl methacrylate.
Further, the molar ratio of the hydroxyl group to the isocyanate group is (1.01 to 1.1): 1.
Further, the photoinitiator includes at least one of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide, and 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone.
The curing agent is one of epoxy resin curing agent, isocyanate curing agent and amine curing agent.
Further, the multifunctional UV viscosity-reducing composition also comprises additives, wherein the additives comprise one or more of a tackifier, a coupling agent, a defoaming agent and a leveling agent.
Further, the solvent is one or more of hexane, cyclohexane, xylene, toluene, tetrahydrofuran, ethyl acetate, butanone, acetone, isopropanol, and isobutanol.
In a second aspect, the invention provides a preparation method of a multifunctional UV viscosity-reducing composition, which comprises the steps of uniformly mixing a solvent type acrylate polymer, a macromolecular polymer of a multi-photosensitive group, a curing agent and a photoinitiator in a solvent under the condition of keeping out of the sun, and standing for defoaming to obtain the multifunctional UV viscosity-reducing composition.
In a third aspect, the invention provides a UV anti-adhesive tape, which comprises a substrate, an adhesive layer and a release layer, wherein the substrate, the adhesive layer and the release layer are sequentially stacked, and the adhesive layer is prepared by coating the multifunctional UV anti-adhesive composition on the substrate and thermally curing.
Further, the base material is a PO film, a PVC film, a PP film, a PET film or a PC film; and/or the release layer is a PET release layer.
Compared with the prior art, the invention has the beneficial effects that:
1. compared with other micromolecule additives, the multifunctional UV viscosity-reducing composition provided by the invention has the advantages that the macromolecular polymer added with multiple photosensitive groups has stronger cohesion when being coated into a glue film, and the glue film is not easy to have the glue residue phenomenon.
2. Compared with the main chain modified UV visbreaking glue, the multifunctional UV visbreaking composition obtained by compounding the solvent type acrylate polymer and the macromolecular polymer of the multi-photosensitive group can adjust the stripping force before and after UV by regulating the proportion of the macromolecular polymer of the multi-photosensitive group in the composition, so that the multifunctional UV visbreaking composition has wider application range and field.
Detailed Description
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The invention provides a multifunctional UV visbreaking composition, which comprises a solvent type acrylate polymer, a multi-photosensitive group macromolecular polymer, a curing agent, a photoinitiator and a solvent, wherein the multi-photosensitive group macromolecular polymer is a (methyl) acrylate polymer with a side group containing a carbon-carbon double bond, the weight average molecular weight of the multi-photosensitive group macromolecular polymer is 8-50 ten thousand, and for example, the weight average molecular weight can be 8-ten thousand, 10-ten thousand, 15-ten thousand, 20-ten thousand, 25-ten thousand, 30-ten-thousand, 35-ten-thousand, 40-thousand, 45-thousand, 50-ten-thousand and the like.
The UV viscosity-reducing composition is a multifunctional UV viscosity-reducing composition formed by compounding a solvent type acrylate polymer and a macromolecular polymer of a multi-photosensitive group, wherein the solvent type acrylate polymer is used as a main adhesive component, so that the composition is endowed with good initial viscosity; and the side group of the macromolecule of the multi-photosensitive group contains a large number of photosensitive groups, namely carbon-carbon double bonds, so that compared with the main chain modification type UV visbreaking acrylic adhesive, the number of the photosensitive groups in the composition is not limited by the number of the polar groups on the acrylic main chain, so that the composition has a larger preparation space during use, and the adjustable peeling force range after UV irradiation is larger.
In addition, in the UV viscosity-reducing composition, the added component is a macromolecular (methyl) acrylate polymer, and the weight average molecular weight of the macromolecular (methyl) acrylate polymer reaches 8-50 ten thousand, so that after the UV viscosity-reducing composition is coated to form a film, macromolecular chains are wound to enable the macromolecular chains to have stronger cohesive force, and no adhesive residue exists.
In the invention, the solvent type polyacrylate polymer used can be solvent type polyacrylate polymer glue which is sold in the market and does not contain or contains little tackifying resin. As an illustrative example, the solvent-type polyacrylate can be Y-2600 (solid content of 19%), Y-4003 (solid content of 23.5%), Y-1410 (solid content of 40%), Y-1411 (solid content of 40%), Y-1420 (solid content of 35%), Y-1421 (solid content of 35%), ND-981 (solid content of 46%), ND-975 (solid content of 42%), D-953 (solid content of 37%), D-943H (solid content of 31%), NC-838 (solid content of 19%), ND-094 (solid content of 26%) and the like of Naozo chemical.
In the invention, the macromolecular polymer of the poly-photosensitive group is obtained by reacting a (methyl) acrylate polymer containing hydroxyl and a (methyl) acrylate monomer containing isocyanate groups. The side group of the hydroxyl-containing (methyl) acrylate polymer contains a large number of hydroxyl groups, and the isocyanate-containing (methyl) acrylate monomer contains a photosensitive group carbon-carbon double bond, so that the photosensitive group can be grafted onto the hydroxyl-containing (methyl) acrylate polymer through the reaction of the hydroxyl groups and the isocyanate groups, and the macromolecular polymer with the side group containing a large number of photosensitive groups is obtained. The weight average molecular weight of the hydroxyl group-containing (meth) acrylate polymer is preferably 5 to 30 ten thousand, and may be, for example, 5, 10, 15, 20, 25, 30 ten thousand, or the like.
In the present invention, the hydroxyl group-containing (meth) acrylate polymer may be obtained by polymerizing a (meth) acrylate monomer having a hydroxyl group at a side group, wherein the (meth) acrylate monomer having a hydroxyl group at a side group includes, but is not limited to, one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, and hydroxypropyl methacrylate. During the synthesis process, the viscosity and the hardness degree of the product can be regulated and controlled by regulating the ratio of different monomers. According to the proportion of the reaction monomers and the selection of the catalyst, the reaction temperature is generally controlled to be 60 ℃ to about 100 ℃, the reaction time is generally in the range of about 2h to 48h, and the reaction environment is nitrogen-filled and oxygen-free.
In the synthesis of the hydroxyl group-containing (meth) acrylate-based polymer, a catalyst known in the art is generally used, and the amount of the catalyst used is generally from 3% to about 0.05% by weight based on the above-mentioned monomers. By way of illustrative example, the catalyst includes, but is not limited to, one or more of Benzoyl Peroxide (BPO), tert-amyl 2-ethylhexyl peroxide (TAPO), 1,1 'bis (tert-amylperoxy) cyclohexane, 1,1' bis (tert-butylperoxy) -3,3,5-trimethylcyclohexane, tert-amyl peroxyacetate (TAPA), tert-amyl peroxybenzoate (TAPB).
After the free radical reaction is finished, a free radical terminator is added to terminate the reaction, and the free radical terminator comprises but is not limited to compounds containing nitrogen or oxygen single electrons, such as DPPH, VDZ, TEMPOL and valence-variable metal salt polymerization inhibitors. The amount of the polymerization inhibitor to be used may be generally determined in accordance with the details of the reaction, such as the amount of the initiator to be added, the reaction temperature and the reaction time, but in general, the amount of the polymerization inhibitor to be added is from 0.5 to about 0.05% by weight based on the above-mentioned monomers to be used. In the synthesis examples given in the present invention, 0.1% by weight is preferable.
The viscosity of the hydroxyl group-containing (meth) acrylate polymer can be controlled using a solvent, and commonly added solvents include, but are not limited to, ketones (acetone, methyl ethyl ketone, etc.), esters (ethyl acetate, butyl acetate, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.), and mixtures thereof.
In the present invention, the isocyanate group-containing (meth) acrylate monomer includes, but is not limited to, isocyanoethyl acrylate (AOI-VM), isocyanoethyl methacrylate (IEM), and the like. In some embodiments, the reaction of the hydroxyl-containing (meth) acrylate polymer with the isocyanate-containing (meth) acrylate monomer is generally controlled to have a hydroxyl to isocyanate molar ratio of (1.01 to 1.1): 1, and may be, for example, 1.1, 1.05.
In the present invention, the curing agent may be any one of an epoxy resin curing agent, an isocyanate curing agent, and an amine curing agent. Specifically, the epoxy resin curing agent can be any one of DER-331, DER-332, E-44 and E-51 which are commercially available; the isocyanate curing agent can be L-75 or L-45 on the market; the amine curing agent may be a commercially available diethylenetriamine or triethylenetetramine.
In the present invention, the photoinitiator may be selected from those commonly used in the art. As illustrative examples, the photoinitiator may be one or more of 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, and 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone.
In the present invention, the solvent may be selected from one or more of hexane, cyclohexane, xylene, toluene, tetrahydrofuran, ethyl acetate, butanone, acetone, isopropanol, and isobutanol.
In some embodiments, the composition further comprises one or more additives, and the present invention is not limited to the kind of the additives, including but not limited to adhesion promoters, leveling agents, antifoaming agents, coupling agents, and the like. Wherein the tackifier is selected from one or more of terpene resin, C5/C9 petroleum resin and rosin resin; the coupling agent may be a silane coupling agent; the leveling agent can be one or more of isophorone, diacetone alcohol and fluoacid ester modified acrylate.
In the invention, no special requirements are made on the content of each component in the composition, and users can adjust the amounts of the macromolecular polymer with multiple photosensitive groups, the curing agent and the photoinitiator according to the requirements. In some embodiments, the multi-photosensitive group macromolecular polymer (solid part) is generally 25 to 75 parts by weight relative to 100 parts by weight of the solvent-type polyacrylate (solid part), and may be, for example, 25 parts, 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, 55 parts, 60 parts, 65 parts, 70 parts, 75 parts, or any value therebetween. The curing agent is generally used in an amount of 0.05 to 5 parts, and may be, for example, 0.05 part, 0.1 part, 0.2 part, 0.4 part, 0.5 part, 0.6 part, 0.8 part, 1 part, 1.5 part, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, 5 parts, or any value therebetween. The photoinitiator is generally used in an amount of 1 to 5 parts, and may be, for example, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, 5 parts, or any value therebetween. The content of the solvent and other additives is not particularly limited as long as curability and adhesive properties of the composition of the present invention are not affected.
When the multifunctional UV viscosity-reducing composition is prepared, a solvent type acrylate polymer, a multi-photosensitive group macromolecular polymer, a curing agent and a photoinitiator are uniformly mixed in a solvent under a light-proof condition, and then the mixture is stood for defoaming.
The multifunctional UV viscosity-reducing composition can be further prepared into a UV viscosity-reducing adhesive tape. The UV anti-adhesive tape generally comprises a base material, an adhesive layer and a release layer which are sequentially laminated, wherein the adhesive layer is prepared by coating the multifunctional UV anti-adhesive composition on the base material and thermally curing. The temperature for thermal curing may be selected according to the particular curing agent used, and typically the curing temperature may be selected to be 80-120 ℃.
In the UV adhesive tape, the substrate may be selected from the substrates commonly used for adhesive tapes, such as PO film, PVC film, PP film, PET film, PC film, etc., and the release layer may be selected from PET release film.
The present invention is further described below in conjunction with specific examples to enable those skilled in the art to better understand the present invention and to practice it, but the examples are not intended to limit the present invention.
The experimental methods used in the following examples are conventional methods unless otherwise specified, and materials, reagents and the like used therein are commercially available without otherwise specified.
TABLE 1 raw materials List
Abbreviation name Name of Chinese Manufacturer or distributor
HEA Acrylic acid hydroxy ethyl ester Aladdin
HEMA Hydroxyethyl methacrylate Aladdin
HPA Hydroxypropyl acrylate Aladdin
IEM Isocyanoethyl methacrylate Aladdin
AOI-VM Acrylic acid isocyano ethyl ester Aladdin
L-75 L-75 polyurethane curing agent Fully developed high-tech materials (Nanjing) Ltd
EA Ethyl acetate Suzhou Chengxin chemical materials Co., ltd
BPO Benzoyl peroxide Jiangsu Qiangsheng chemical industry
TEMPOL 2,2,6,6-Tetramethylpiperidine oxide Changzhou jiana chemical industry
Y-2600 Polyacrylate An Zuo chemistry
Y-1410 Polyacrylates An Zuo chemistry
1. Synthesis of poly (hydroxyethyl (meth) acrylate)
Synthesis example S1
Adding 100g HEA,100g EA and 1g BPO into a reaction kettle provided with a mechanical stirrer, a condensing device, a heating device and a nitrogen filling device, uniformly stirring, opening a nitrogen valve, removing air in the device, reacting for 4 hours at 85 ℃, closing the nitrogen valve, reducing the temperature, adding 0.1g TEMPOL for polymerization inhibition to prepare poly (methyl) hydroxyethyl acrylate S1 (the solid content of the product is about 50 percent, and the weight-average molecular weight is 125724).
Synthesis example S2
50g of HEMA, 50g of HEA,100g of EA and 3g of BPO are added into a reaction kettle provided with a mechanical stirrer, a condensing device, a heating device and a nitrogen filling device for uniform stirring, a nitrogen valve is opened, the air in the device is removed, the reaction lasts for 4 hours at 85 ℃, the nitrogen valve is closed, the temperature is reduced, and 0.1g of TEMPOL is added for polymerization inhibition to prepare the poly (methyl) hydroxyethyl acrylate S2 (the solid content of the product is about 50 percent, and the weight-average molecular weight is 93164).
Synthesis example S3
Adding 100g HPA,100 g EA and 3g BPO into a reaction kettle provided with a mechanical stirrer, a condensing device, a heating device and a nitrogen filling device, uniformly stirring, opening a nitrogen valve, removing air in the device, reacting for 4 hours at 85 ℃, closing the nitrogen valve, reducing the temperature, adding 0.1g TEMPOL for polymerization inhibition to prepare the poly (methyl) hydroxyethyl acrylate S3 (the solid content of the product is about 50 percent, and the weight-average molecular weight is 67285).
2. Synthesis of macromolecular polymers of multiple photosensitive groups
Synthesis example S4
Into a reaction vessel equipped with a mechanical stirrer, a condenser and a heater, 100g of S1 (containing 0.431mol of hydroxyl group) and 66g of IEM (containing 0.425mol of isocyanate group) were charged, stirred uniformly, and reacted at 80 ℃ for 4 hours to obtain a photosensitive block-type macromolecular polymer S4 (weight average molecular weight 261399).
Synthesis example S5
Into a reaction vessel equipped with a mechanical stirrer, a condenser and a heater, 100g of S2 (containing 0.407mol of hydroxyl group) and 57g of AOI-VM (containing 0.404mol of isocyanate group) were added, and the mixture was stirred uniformly and reacted at 80 ℃ for 4 hours to obtain a photosensitive block-based macromolecular polymer S5 (weight average molecular weight 172394).
Synthesis example S6
Into a reaction vessel equipped with a mechanical stirrer, a condenser and a heater, 100g of S3 (containing 0.384mol of hydroxyl group) and 54g of AOI-VM (containing 0.382mol of isocyanate group) were added, and the mixture was stirred uniformly and reacted at 80 ℃ for 4 hours to obtain a photosensitive block-based macromolecular polymer S6 (weight-average molecular weight 124506).
3. Synthesis of multifunctional UV visbreaking compositions
Example E1
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 71g of macromolecular polymer S4 of multi-photosensitive group (solid content: 70%), 1.5g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E1 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E2
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 71g of macromolecular polymer S5 of multi-photosensitive group (solid content: 70%), 1.5g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E2 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E3
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 75g of macromolecular polymer S6 of multi-photosensitive group (solid content: 67%), 1.5g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E3 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E4
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 36g of macromolecular polymer S4 of multi-photosensitive group (solid content: 70%), 1.5g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E4 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E5
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 107g of macromolecular polymer S4 of poly-photosensitive group (solid content: 70%), 1.5g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone and 50g of ETAC are added into a 250mL plasticizing cup to be mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E5 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E6
250g of solvent type polyacrylate Y-1410 (solid content: 40%), 71g of multi-photosensitive group macromolecular polymer S4 (solid content: 70%), 0.05g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E6 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film for testing.
Example E7
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 71g of macromolecular polymer S4 of multi-photosensitive group (solid content: 70%), 5g of curing agent L-75,2g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E7 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E8
526g of solvent-based polyacrylate Y-2600 (solid content: 19%), 71g of multi-photosensitive macromolecular polymer S4 (solid content: 70%), 5g of curing agent L-75,1g of photoinitiator 2-hydroxy-2-methyl-1-phenylacetone and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E8 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film used for testing.
Example E9
526g of solvent type polyacrylate Y-2600 (solid content: 19%), 71g of macromolecular polymer S4 of multi-photosensitive group (solid content: 70%), 5g of curing agent L-75,5g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added into a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed solution obtained in the embodiment E9 on a layer of PET release film, baking for 3min in a 120 ℃ baking oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film for testing.
Comparative example C1
526g of solvent-based polyacrylate Y-2600 (19% solids), 1.5g of curing agent L-75, and 50g of ETAC were added to a 250mL plasticizing cup and mixed and stirred uniformly.
Preparing an adhesive film: and uniformly coating the uniformly mixed liquid of the comparative example C1 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and covering another layer of PET release film on the surface of the obtained dried adhesive film after drying to obtain the adhesive film for testing.
Comparative example C2
71g of the macromolecular polymer S4 (solid content: 70%) of the multi-photosensitive group, 1.5g of the curing agent L-75,2g of the photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added to a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and (3) uniformly coating the uniformly mixed liquid of the comparative example C2 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and after drying, covering another layer of PET release film on the surface of the obtained dried adhesive film to obtain the adhesive film for testing.
Comparative example C3
71g of the macromolecular polymer S5 (solid content: 69%) of the multi-photosensitive group, 1.5g of the curing agent L-75,2g of the photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone, and 50g of ETAC were added to a 250mL plasticizing cup, mixed and stirred uniformly.
Preparing an adhesive film: and uniformly coating the uniformly mixed liquid of the comparative example C3 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and covering another layer of PET release film on the surface of the obtained dried adhesive film after drying to obtain the adhesive film for testing.
Comparative example C4
71g of the macromolecular polymer S6 (solid content: 67%) of the multi-photosensitive group, 1.5g of the curing agent L-75,2g of the photoinitiator 2-hydroxy-2-methyl-1-phenylpropanone and 50g of ETAC were added to a 250mL plasticizing cup and mixed and stirred uniformly.
Preparing an adhesive film: and uniformly coating the uniformly mixed liquid of the comparative example C4 on a layer of PET release film, baking for 3min in a 120 ℃ oven, and covering another layer of PET release film on the surface of the obtained dried adhesive film after drying to obtain the adhesive film for testing.
The adhesive films of examples E1 to E9 and comparative examples C1 to C4 were tested for their properties according to the following test methods:
adhesion of SUS (mirror steel plate) with 180 ° peel force before UV: the prepared adhesive film is attached to a 50um PET substrate, and the test is carried out according to GB 2792-81;
after UV 180 ° peel force to SUS (mirror steel plate): the prepared adhesive film was attached to a 50um PET substrate, and the irradiation was adjusted to 70mW for 60s using a 350nM LED lamp, and the test was performed with reference to GB 2792-81.
TABLE 2 results of Performance test of examples E1 to E9 and comparative examples C1 to C4
Figure BDA0003927490200000111
According to the test results in table 2, the E1 to E3 products have better peeling force before UV and lower peeling force after UV, and the macromolecular polymers S4 to S6 of different poly-sensitive groups do not show obvious difference in peeling force before UV due to no obvious difference in the addition amount of the composition. Adjusting the ratio of the macromolecular polymer of the multisensory mass, e.g., E4, the pre-UV ratio tended to be comparative example C1, but the corresponding post-UV peel force increased. Increasing the proportion of the polymeric macromolecules of the multisensitive clusters, such as E5, decreases the pre-UV peel force and correspondingly decreases the post-UV peel force. By comparing E7, E8 and E9, data tests show that the peeling force before UV and after UV is not obviously different, and a small amount of the initiator can play a role in UV viscosity reduction.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.

Claims (10)

1. The multifunctional UV visbreaking composition is characterized by comprising 100 parts by weight of solvent type acrylate polymer, 25-75 parts by weight of macromolecular polymer of a multi-photosensitive group, 0.05-5 parts by weight of curing agent, 1-5 parts by weight of photoinitiator and solvent, wherein the macromolecular polymer of the multi-photosensitive group is a (methyl) acrylate polymer with a side group containing carbon-carbon double bonds, and the weight-average molecular weight of the macromolecular polymer is 8-50 ten thousand.
2. The multifunctional UV visbreaking composition of claim 1, wherein the macromolecular polymer of the polysensitive group is obtained by reacting a hydroxyl group-containing (meth) acrylate polymer with an isocyanate group-containing (meth) acrylate monomer; wherein the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 5-30 ten thousand.
3. The multifunctional UV vis-breaking composition of claim 2, wherein the hydroxyl-containing (meth) acrylate polymer is obtained by polymerization of a hydroxyl-pendant (meth) acrylate monomer comprising one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, and hydroxypropyl methacrylate.
4. The multifunctional UV vis-breaking composition of claim 2, wherein the isocyanate group-containing (meth) acrylate monomer comprises at least one of isocyanatoethyl acrylate and isocyanatoethyl methacrylate.
5. The multifunctional UV visbreaking composition of claim 2, wherein the molar ratio of hydroxyl groups to isocyanate groups is (1.01-1.1): 1.
6. The multifunctional UV vis-breaking composition of claim 1, wherein the photoinitiator comprises at least one of 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxycyclohexylphenylketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, and 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone;
the curing agent is one of an epoxy resin curing agent, an isocyanate curing agent and an amine curing agent;
the solvent is one or more of hexane, cyclohexane, xylene, toluene, tetrahydrofuran, ethyl acetate, butanone, acetone, isopropanol and isobutanol.
7. The multifunctional UV visbreaking composition of claim 1, further comprising additives including one or more of adhesion promoters, coupling agents, defoamers, and leveling agents.
8. The method for preparing a multifunctional UV visbreaking composition according to any one of claims 1 to 7, wherein the multifunctional UV visbreaking composition is obtained by uniformly mixing a solvent type acrylate polymer, a multi-photosensitive group macromolecular polymer, a curing agent and a photoinitiator in a solvent under the condition of avoiding light, and then standing for defoaming.
9. A UV anti-adhesive tape comprising a substrate, an adhesive layer and a release layer laminated in this order, wherein the adhesive layer is obtained by applying the multifunctional UV anti-adhesive composition according to any one of claims 1 to 7 to the substrate and thermally curing the composition.
10. The UV adhesive tape according to claim 9, wherein the substrate is a PO film, a PVC film, a PP film, a PET film or a PC film; and/or the release layer is a PET release layer.
CN202211377832.6A 2022-11-04 2022-11-04 Multifunctional UV viscosity-reducing composition and preparation method and application thereof Pending CN115627135A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130047234A (en) * 2011-10-31 2013-05-08 (주)엘지하우시스 Composition of adhesive film in touch screen panel for rework process
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
CN115232578A (en) * 2022-08-17 2022-10-25 苏州赛伍应用技术股份有限公司 UV viscosity-reducing adhesive and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130047234A (en) * 2011-10-31 2013-05-08 (주)엘지하우시스 Composition of adhesive film in touch screen panel for rework process
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
CN115232578A (en) * 2022-08-17 2022-10-25 苏州赛伍应用技术股份有限公司 UV viscosity-reducing adhesive and preparation method thereof

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