CN116731616A - UV (ultraviolet) curing acrylic pressure-sensitive adhesive, pressure-sensitive adhesive film and preparation method of pressure-sensitive adhesive film - Google Patents
UV (ultraviolet) curing acrylic pressure-sensitive adhesive, pressure-sensitive adhesive film and preparation method of pressure-sensitive adhesive film Download PDFInfo
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- CN116731616A CN116731616A CN202310758537.3A CN202310758537A CN116731616A CN 116731616 A CN116731616 A CN 116731616A CN 202310758537 A CN202310758537 A CN 202310758537A CN 116731616 A CN116731616 A CN 116731616A
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- China
- Prior art keywords
- sensitive adhesive
- acrylate
- pressure
- monomer
- acrylic
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 70
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 59
- 239000000178 monomer Substances 0.000 claims abstract description 51
- 238000004132 cross linking Methods 0.000 claims abstract description 19
- -1 acrylic ester Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000003848 UV Light-Curing Methods 0.000 claims abstract description 14
- 239000004971 Cross linker Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- 239000000853 adhesive Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 5
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 4
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims description 4
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 3
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 8
- 238000001723 curing Methods 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 5
- 238000005286 illumination Methods 0.000 abstract description 4
- 238000007711 solidification Methods 0.000 abstract description 4
- 230000008023 solidification Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002390 adhesive tape Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000004831 Hot glue Substances 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
- C09J7/24—Plastics; Metallised plastics based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/241—Polyolefin, e.g.rubber
- C09J7/243—Ethylene or propylene polymers
-
- 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
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- 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
- C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
- C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
- C09J2301/122—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present only on one side of the carrier, e.g. single-sided adhesive tape
-
- 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
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
-
- 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
- C09J2423/00—Presence of polyolefin
- C09J2423/10—Presence of homo or copolymers of propene
- C09J2423/106—Presence of homo or copolymers of propene in the substrate
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a UV (ultraviolet) curing acrylic ester pressure-sensitive adhesive, a pressure-sensitive adhesive film and a preparation method thereof, wherein the pressure-sensitive adhesive comprises the following raw material components in parts by weight: acrylic soft monomer: 75-90%; acrylic ester functional monomer: 5-15%; heat-resistant crosslinking monomer: 3-8%; multifunctional acrylate crosslinker: 0.01 to 2 percent; and (3) a photoinitiator: 0.01-2%. The synthesis process of the invention is simple, and the UV curing acrylic pressure-sensitive adhesive can be obtained in two steps, thereby reducing the production cost. The UV curing method is adopted, and an organic solvent is not needed, so that the problem of solvent volatilization is not needed when the UV curing method is used, and the environment is protected; and ultraviolet light has strong penetrability, can realize the solidification of thick coating type products under proper illumination intensity, and has obvious advantages compared with the heat solidification in conversion rate.
Description
Technical Field
The invention relates to the field of pressure-sensitive adhesive materials, in particular to a UV (ultraviolet) curing acrylic pressure-sensitive adhesive, a pressure-sensitive adhesive film and a preparation method thereof.
Background
Pressure Sensitive Adhesives (PSAs) are adhesives that are sensitive to pressure, adhere to the surface of an object under light pressure, and do not leave a residue on the surface of the object when peeled. In recent years, pressure-sensitive adhesives have been rapidly developed and widely used in the fields of automobiles, electronics, medicine, industry and the like. The acrylic pressure-sensitive adhesive is the adhesive which has the most rapid development and the most wide application prospect at present, is mainly prepared by copolymerizing acrylic monomers, and has the advantages of good chemical stability, wide bonding range, no toxicity, aging resistance, low cost and the like. Acrylate pressure-sensitive adhesives can be further classified into emulsion type, solvent type, hot melt type and radiation curable type.
However, with the continuous development of industrialization, the requirements of partial industries on the performance of the pressure-sensitive adhesive are more and more strict, the performance of the common pressure-sensitive adhesive is poor after the pressure-sensitive adhesive is subjected to high temperature and high humidity, and residual adhesive exists after stripping, so that the application field of the pressure-sensitive adhesive is greatly limited.
The patent CN103205226B adopts isooctyl acrylate, acrylic acid, (methyl) acrylic ester containing two double bonds, benzoyl peroxide and solvent ethyl acetate to prepare solvent type acrylic ester pressure-sensitive adhesive, and the acrylic ester pressure-sensitive adhesive prepared by compounding with polyfunctional aziridine crosslinking agent has good high-temperature and high-humidity aging resistance, and can not leave residual glue and mottle after being torn off from the surface of ASA profile.
The patent CN111234739A is a bi-component temperature-resistant aqueous pressure-sensitive adhesive, which is prepared by crosslinking aqueous acrylic ester pressure-sensitive emulsion, tackifying emulsion, thickening agent, defoamer, bactericide, PH regulator and the like after being compounded with aliphatic polyisocyanate with hydrophilic groups, thus improving the temperature resistance of the pressure-sensitive adhesive and having certain boiling resistance.
The patent CN112457806A is a high-temperature-resistant hot-melt pressure-sensitive adhesive, and the formula is composed of polyisobutene, a plasticizer, matrix resin, tackifying resin, styrene-butadiene rubber, inorganic filler, an antioxidant, an ultraviolet absorber and a coupling agent, and the mixture is stirred at 160-200 ℃ until the materials are completely melted, and then a thermoplastic elastomer is added, vacuumized and uniformly mixed, so that the prepared hot-melt adhesive has excellent high-temperature viscosity, high-low temperature resistance and wide use temperature range.
The existing scheme mainly has the following defects:
1. the process is complex and the energy consumption is high. The solvent-type or emulsion-type pressure-sensitive adhesive reaction conditions all require continuous heating for a plurality of hours, and the polymerization process has complex steps and long time; the hot melt adhesive needs to be heated and melted in the configuration process, the heat is needed to be much, the UV curing can initiate polymerization at normal temperature, the polymerization process can be completed in tens of seconds to a few minutes, and the process time is greatly shortened.
2. Solvent type acrylic ester pressure-sensitive adhesive, which mostly uses toluene, ethyl acetate, n-hexane and other organic solvents as reaction medium, has large smell and pollutes the environment.
3. For solvent-based or emulsion-based pressure-sensitive adhesives, the cost of producing thick-coated products is too great. The thickness is increased, and the solvent and water in the system are difficult to volatilize in a short time, so that a considerable amount of hot ovens are needed, and the production cost and the energy consumption are increased intangibly.
Disclosure of Invention
The invention aims to solve the technical problems of the prior art and provides a UV curing acrylic pressure-sensitive adhesive, a pressure-sensitive adhesive film and a preparation method thereof.
In order to solve the technical problems, the invention adopts the following technical scheme: the invention provides a UV-curable acrylate pressure-sensitive adhesive, which comprises the following raw material components in parts by weight:
acrylic soft monomer: 75-90%;
acrylic ester functional monomer: 5-15%;
heat-resistant crosslinking monomer: 3-8%;
multifunctional acrylate crosslinker: 0.01 to 2 percent;
and (3) a photoinitiator: 0.01-2%.
Preferably, the heat-resistant crosslinking monomer contains both an unsaturated ethylenic bond and a polar group in the molecular chain.
Preferably, the heat-resistant crosslinking monomer is one or more of acryloylmorpholine, vinylcaprolactam, N-vinylpyrrolidone and N-vinylcarbazole.
Preferably, the acrylic soft monomer comprises one or more of butyl acrylate, butyl methacrylate, isooctyl acrylate and lauryl acrylate.
Preferably, the acrylate functional monomer comprises one or more of acrylic acid, methacrylic acid, itaconic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate.
Preferably, the multifunctional acrylate crosslinking agent is an acrylate monomer with a functional group of more than or equal to 2.
Preferably, the multifunctional acrylate cross-linking agent is one or more of triethylene glycol dimethacrylate, diethylene glycol dimethacrylate, 1, 6-hexanediol diacrylate, 1, 3-butanediol dimethacrylate, ethoxylated bisphenol A diacrylate and ethoxylated bisphenol A dimethacrylate.
Preferably, the photoinitiator selected is one or a mixture of several of TPO, irgacure 184, irgacure 819, darocure1173, omnirad 651.
In a second aspect of the present invention, there is provided a method for preparing the UV-curable acrylate pressure-sensitive adhesive as described above, comprising the steps of:
s1, synthesizing an acrylic ester prepolymer: mixing and stirring acrylate soft monomers, acrylate functional monomers, heat-resistant crosslinking monomers and partial photoinitiators uniformly under nitrogen atmosphere, and irradiating under UV light to prepare acrylate prepolymer;
s2, preparing a UV curing acrylate pressure-sensitive adhesive: and (2) adding the multifunctional acrylate crosslinking agent and the rest of photoinitiator into the acrylate prepolymer prepared in the step (S1), uniformly mixing, filtering and removing bubbles to obtain the UV-cured acrylate pressure-sensitive adhesive.
In a third aspect of the present invention, there is provided a pressure-sensitive adhesive film prepared by the following method:
and coating the UV-cured acrylate pressure-sensitive adhesive on a substrate, attaching a release film on the adhesive surface, and curing under UV illumination to obtain the pressure-sensitive adhesive film.
The beneficial effects of the invention are as follows:
the synthesis process of the invention is simple, and the UV curing acrylic pressure-sensitive adhesive can be obtained in two steps, thereby reducing the production cost.
The UV curing method is adopted, and an organic solvent is not needed, so that the problem of solvent volatilization is not needed when the UV curing method is used, and the environment is protected; and ultraviolet light has strong penetrability, can realize the solidification of thick coating type products under proper illumination intensity, and has obvious advantages compared with the heat solidification in conversion rate.
According to the formula, the heat-resistant monomer is adopted to participate in polymerization, and the selected heat-resistant monomer not only contains C=C which can participate in free radical polymerization, but also contains a group with strong polarity, so that the rigidity of a molecular chain segment is improved to a certain extent, and meanwhile, N-H in the polar group can also form a hydrogen bond with C=O and OH on the chain segment, so that the intermolecular acting force is further improved, and the heat resistance of the adhesive film is improved.
Detailed Description
The present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the same by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The test methods used in the following examples are conventional methods unless otherwise specified. The material reagents and the like used in the following examples are commercially available unless otherwise specified. The following examples were conducted under conventional conditions or conditions recommended by the manufacturer, without specifying the specific conditions. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The invention provides a UV (ultraviolet) curing acrylic ester pressure-sensitive adhesive which comprises the following raw material components in parts by weight:
acrylic soft monomer: 75-90%;
acrylic ester functional monomer: 5-15%;
heat-resistant crosslinking monomer: 3-8%;
multifunctional acrylate crosslinker: 0.01 to 2 percent;
and (3) a photoinitiator: 0.01-2%.
In a preferred embodiment, the acrylic soft monomer comprises one or more of butyl acrylate, butyl methacrylate, isooctyl acrylate, and lauryl acrylate.
In a preferred embodiment, the acrylate-based functional monomer comprises one or more of acrylic acid, methacrylic acid, itaconic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate.
In a preferred embodiment, the heat-resistant crosslinking monomer contains both an unsaturated ethylenic bond and a polar group on the molecular chain that can participate in the polymerization reaction. The heat-resistant crosslinking monomer is one or more of acryloylmorpholine, vinylcaprolactam, N-vinylpyrrolidone and N-vinylcarbazole.
In a preferred embodiment, the multifunctional acrylate crosslinker is an acrylate monomer having a functional group of ≡2. The multifunctional acrylate cross-linking agent is one or more of triethylene glycol dimethacrylate, diethylene glycol dimethacrylate, 1, 6-hexanediol diacrylate, 1, 3-butanediol dimethacrylate, ethoxylated bisphenol A diacrylate and ethoxylated bisphenol A dimethacrylate.
In a preferred embodiment, the photoinitiator selected is one or a mixture of several of TPO, irgacure 184, irgacure 819, darocure1173, omnirad 651. The photoinitiator belongs to a free radical initiator, and the substances absorb energy with a certain wavelength under ultraviolet light so as to generate free radicals to initiate double bond polymerization to form a stable adhesive layer.
The invention also provides a preparation method of the UV curing acrylic pressure-sensitive adhesive, which comprises the following steps:
s1, synthesizing an acrylic ester prepolymer: mixing and stirring acrylate soft monomers, acrylate functional monomers, heat-resistant crosslinking monomers and partial photoinitiators uniformly under nitrogen atmosphere, and irradiating under UV light to prepare acrylate prepolymer;
s2, preparing a UV curing acrylate pressure-sensitive adhesive: and (2) adding the multifunctional acrylate cross-linking agent and the rest of photoinitiator into the acrylate prepolymer prepared in the step (S1), uniformly mixing, filtering and removing bubbles to obtain the UV-cured acrylate pressure-sensitive adhesive.
The invention also provides a pressure-sensitive adhesive film, which is prepared by the following method:
and coating the UV-cured acrylate pressure-sensitive adhesive on a substrate, attaching a release film on the adhesive surface, and curing under UV illumination to obtain the pressure-sensitive adhesive film.
The following provides detailed examples and comparative examples to further illustrate the invention.
The pressure-sensitive adhesive films provided in the following examples and comparative examples were prepared in substantially the same manner, and were specifically as follows:
s1, synthesizing an acrylic ester prepolymer: mixing and stirring acrylate soft monomer, acrylate functional monomer, heat-resistant crosslinking monomer and partial photoinitiator under nitrogen atmosphere uniformly at 1.5mW/cm 2 Irradiating for 2min under UV light to obtain acrylate prepolymer;
s2, preparing a UV curing acrylate pressure-sensitive adhesive: and (2) adding the multifunctional acrylate crosslinking agent and the rest of photoinitiator into the acrylate prepolymer prepared in the step (S1), uniformly mixing, filtering by 200 meshes, vacuumizing and removing bubbles to obtain the UV-cured acrylate pressure-sensitive adhesive.
S3, coating the UV-cured acrylate pressure-sensitive adhesive on a substrate (PP film), controlling the coating thickness to be 100+/-5 mu m, then attaching a PET release film on the adhesive surface, and using the energy of 3500mj/cm 2 And (3) irradiating for 3min by UV light, and curing to obtain the pressure-sensitive adhesive film.
Wherein, for a part of the components not contained in the examples or comparative examples, the components were omitted in the corresponding steps.
In the following examples and comparative examples, specific choices of each type of component involved are as follows:
the acrylic ester soft monomer is a mixture of isooctyl acrylate and butyl acrylate, the acrylic ester functional monomer is a mixture of hydroxyethyl acrylate and acrylic acid, the heat-resistant crosslinking monomer is vinyl caprolactam and/or acryloylmorpholine, the multifunctional acrylic ester crosslinking agent is 1, 6-hexanediol diacrylate, and the photoinitiator is Darocure1173, namely a photoinitiator 1173.
The specific formulations of the following examples and comparative examples are shown in the following tables 1 and 2, respectively, in which the numerical units are parts by weight.
TABLE 1
TABLE 2
The pressure-sensitive adhesive films of examples and comparative examples were subjected to the following performance tests:
1. detection of primary adhesion: the adhesive tape was tested for loop tack according to GB/T31125-2014.
2. And (3) detection of peel strength: measured according to the 180 DEG peel strength test method of GB 2792-1998 pressure sensitive adhesive tape.
3. And (3) detecting the holding power: according to GB/T4851-1998, 1.0kg weight, 85% humidity, 85 ℃ x 72h, viscosity performance test result displacement distance
4. And (3) wet heat resistance detection: and (3) leaching absolute ethyl alcohol by absorbent cotton to wipe the stainless steel plate clean, uniformly attaching the prepared pressure-sensitive adhesive on the mirror surface steel plate, putting the mirror surface steel plate into an oven, standing for 3 days under the condition of 85 ℃/85%RH, taking out and cooling to room temperature, then slowly stripping the adhesive tape, observing the surface condition of the mirror surface steel plate, and mainly observing the deformation condition and the adhesive residue phenomenon of the adhesive tape.
The test results are shown in table 3 below:
TABLE 3 Table 3
Compared with examples 1-9, the adhesive tapes prepared by the comparative example 1 have the advantages that the holding force displacement of examples 1-9 is obviously improved, no residual adhesive exists in the heat resistance test, and the method for modifying the heat-resistant crosslinking monomer adopted by the invention can obviously improve the holding force and the wet heat resistance of the pressure-sensitive adhesive.
Comparative examples 2 to 3 are compared with examples 1 to 9, and it can be found that when the addition ratio of the heat-resistant crosslinking monomer is less than 3%, the adhesive tape produced is excellent in initial adhesion, but is inferior in holding power and wet heat resistance, mainly because the number of hydrogen bonds formed between the heat-resistant monomer and other functional monomers is small, and the cohesive force of the adhesive tape cannot be significantly improved.
Comparative examples 4 to 5 compared with examples 1 to 9, it was found that when the addition ratio of the heat-resistant crosslinking monomer was higher than 8%, the peel strength and the primary adhesion of the produced adhesive tape were lower, but the holding adhesion and wet heat resistance were better, mainly because the homopolymer of the heat-resistant monomer had a higher glass transition temperature, resulting in an increase in the glass transition temperature of the adhesive tape, and a decrease in the wettability of the adhesive film; meanwhile, the polar group has large steric hindrance, and the movement capability of the chain segment is limited after the macromolecular chain is introduced, so that the viscoelasticity of the adhesive tape is reduced, and the performance of the adhesive tape is finally influenced.
Although embodiments of the present invention have been disclosed above, it is not limited to the use of the description and embodiments, it is well suited to various fields of use for the invention, and further modifications may be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the particular details without departing from the general concepts defined in the claims and the equivalents thereof.
Claims (10)
1. The UV curing acrylic pressure-sensitive adhesive is characterized by comprising the following raw material components in parts by weight:
acrylic soft monomer: 75-90%;
acrylic ester functional monomer: 5-15%;
heat-resistant crosslinking monomer: 3-8%;
multifunctional acrylate crosslinker: 0.01 to 2 percent;
and (3) a photoinitiator: 0.01-2%.
2. The UV curable acrylate pressure sensitive adhesive according to claim 1, wherein the heat resistant cross-linking monomer contains both an unsaturated olefinic bond and a polar group on the molecular chain.
3. The UV curable acrylate pressure sensitive adhesive according to claim 2, wherein the heat resistant crosslinking monomer is one or more of acryloylmorpholine, vinylcaprolactam, N-vinylpyrrolidone and N-vinylcarbazole.
4. The UV curable acrylate pressure sensitive adhesive according to claim 1 wherein the acrylic soft monomer comprises one or more of butyl acrylate, butyl methacrylate, isooctyl acrylate and lauryl acrylate.
5. The UV curable acrylate pressure sensitive adhesive according to claim 1 wherein the acrylate functional monomer comprises one or more of acrylic acid, methacrylic acid, itaconic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate.
6. The UV curable acrylate pressure sensitive adhesive according to claim 1, wherein the multifunctional acrylate cross-linking agent is an acrylate monomer having a functional group of 2 or more.
7. The UV curable acrylate pressure sensitive adhesive according to claim 6 wherein the multifunctional acrylate cross-linking agent is one or more of triethylene glycol dimethacrylate, diethylene glycol dimethacrylate, 1, 6-hexanediol diacrylate, 1, 3-butanediol dimethacrylate, ethoxylated bisphenol a diacrylate, ethoxylated bisphenol a dimethacrylate.
8. The UV curable acrylate pressure sensitive adhesive according to claim 1, wherein the selected photoinitiator is one or a mixture of several of TPO, irgacure 184, irgacure 819, darocure1173, omnirad 651.
9. A method for preparing the UV-curable acrylate pressure-sensitive adhesive according to any one of claims 1 to 8, comprising the steps of:
s1, synthesizing an acrylic ester prepolymer: mixing and stirring acrylate soft monomers, acrylate functional monomers, heat-resistant crosslinking monomers and partial photoinitiators uniformly under nitrogen atmosphere, and irradiating under UV light to prepare acrylate prepolymer;
s2, preparing a UV curing acrylate pressure-sensitive adhesive: and (2) adding the multifunctional acrylate crosslinking agent and the rest of photoinitiator into the acrylate prepolymer prepared in the step (S1), uniformly mixing, filtering and removing bubbles to obtain the UV-cured acrylate pressure-sensitive adhesive.
10. The pressure-sensitive adhesive film is characterized by being prepared by the following steps:
the UV-curable acrylate pressure-sensitive adhesive according to any one of claims 1 to 8 is coated on a substrate, and then a release film is attached to the adhesive surface, and cured under UV light irradiation, thereby obtaining the pressure-sensitive adhesive film.
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