CN115232578B - UV (ultraviolet) adhesive and preparation method thereof - Google Patents
UV (ultraviolet) adhesive and preparation method thereof Download PDFInfo
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- CN115232578B CN115232578B CN202210987973.3A CN202210987973A CN115232578B CN 115232578 B CN115232578 B CN 115232578B CN 202210987973 A CN202210987973 A CN 202210987973A CN 115232578 B CN115232578 B CN 115232578B
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 83
- 239000000853 adhesive Substances 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 82
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 68
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 60
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 75
- 239000000178 monomer Substances 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 29
- 239000003999 initiator Substances 0.000 claims description 26
- 238000002156 mixing Methods 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- 239000002390 adhesive tape Substances 0.000 claims description 13
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 12
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 8
- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 claims description 8
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 8
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 claims description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- UERLHASVVYLVKI-UHFFFAOYSA-N 1-propan-2-yl-9h-thioxanthene Chemical compound S1C2=CC=CC=C2CC2=C1C=CC=C2C(C)C UERLHASVVYLVKI-UHFFFAOYSA-N 0.000 claims description 2
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 2
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- IIQWTZQWBGDRQG-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C(C)=C IIQWTZQWBGDRQG-UHFFFAOYSA-N 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000013557 residual solvent Substances 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 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 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 abstract description 14
- 239000003292 glue Substances 0.000 abstract description 6
- 238000004132 cross linking Methods 0.000 abstract description 3
- 238000013508 migration Methods 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- -1 alkyl methacrylate Chemical compound 0.000 description 20
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000007599 discharging Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 238000001029 thermal curing Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- 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
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- 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
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a UV (ultraviolet) adhesive and a preparation method thereof, wherein the UV adhesive comprises the following components in parts by weight: 10 to 40 parts of carbon-carbon double bond-containing high molecular weight acrylic resin, 10 to 40 parts of carbon-carbon double bond-containing low molecular weight acrylic resin, 0.5 to 3 parts of photoinitiator, 0.01 to 1 part of thermosetting agent and 30 to 50 parts of organic solvent; the weight average molecular weight of the carbon-carbon double bond-containing high molecular weight acrylic resin is 50-100 ten thousand, and the weight average molecular weight of the carbon-carbon double bond-containing high molecular weight acrylic resin is 5-40 ten thousand. The UV glue reducing adhesive prepared by the invention utilizes the low molecular weight acrylic resin to improve the initial adhesion and the stripping force of the UV glue reducing adhesive, and forms an interpenetrating structure with the high molecular weight acrylic resin and the low molecular weight acrylic resin to avoid the phenomenon of residual glue during stripping, and simultaneously utilizes the carbon-carbon double bond of the acrylic resin body to generate polymerization and crosslinking after UV irradiation, so that larger volume shrinkage is generated to reduce the stripping force, and the glue reducing adhesive does not need to be added with a flatting agent, so that the pollution of migration of the flatting agent to the attached object can be reduced.
Description
Technical Field
The invention relates to the technical field of adhesives, in particular to a UV (ultraviolet) adhesive reducing adhesive and a preparation method thereof.
Background
The UV anti-adhesion adhesive tape has high adhesion before UV irradiation, has good adhesion, greatly reduces adhesion after short-time UV irradiation when separation is needed, and is easy to tear, so that the UV anti-adhesion adhesive tape is widely applied to the processing and manufacturing processes of products such as semiconductor chips, transistors, integrated circuits, printed circuit boards, optical microscopes and the like.
However, most of UV (ultraviolet) adhesive in the current market is formed by mixing an acrylic polymer adhesive, and then adding a polyfunctional reactive diluent, a photoinitiator and a curing agent, wherein the reactive diluent is mostly small molecules, and after an adhesive tape is attached to an object to be attached, migration of the small molecule reactive diluent to the interface of the object to be attached is caused due to limited compatibility in a system, so that initial viscosity and stripping force are reduced, and adhesive residues are easy to occur after crosslinking; in addition, the UV-curable adhesive has a problem of low initial adhesion after the preparation of the adhesive-reducing tape, resulting in difficulty in adhesion. At present, the initial adhesion of the adhesive tape is improved by reducing the weight average molecular weight, but the adhesive tape can cause the phenomenon of adhesive residue when the adhesive tape is peeled off an object to be adhered after the weight average molecular weight is reduced; while the excessively high weight average molecular weight can improve the defect of residual adhesive, the peeling strength of the adhesive tape on the adhered object can be reduced, the fixing, protecting and adhesive transferring effects of the UV anti-adhesive tape in the manufacturing process of the semiconductor wafer are reduced, and the product is easy to be scrapped due to displacement.
Disclosure of Invention
The invention aims to solve the technical problem of providing a UV (ultraviolet) adhesive and a preparation method thereof, wherein two acrylic resins containing carbon-carbon double bonds with different molecular weights are synthesized and mixed with a photoinitiator and a curing crosslinking agent according to a certain proportion, so that the UV adhesive with low viscosity, high initial adhesion, high stripping force before UV irradiation, low stripping force after UV irradiation and no adhesive residue can be achieved.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention provides a UV (ultraviolet) adhesive, which comprises the following components in parts by weight: 10 to 40 parts of carbon-carbon double bond-containing high molecular weight acrylic resin, 10 to 40 parts of carbon-carbon double bond-containing low molecular weight acrylic resin, 0.5 to 3 parts of photoinitiator, 0.01 to 1 part of thermosetting agent and 30 to 50 parts of organic solvent;
the weight average molecular weight of the high molecular weight acrylic resin containing carbon-carbon double bonds is 50-100 ten thousand, and the glass transition temperature is-50 to-20 ℃; the content of the carbon-carbon double bond in the carbon-carbon double bond-containing high molecular weight acrylic resin is 0.1-2 mmol/g;
the weight average molecular weight of the low molecular weight acrylic resin containing carbon-carbon double bonds is 5 ten thousand to 40 ten thousand, and the glass transition temperature is-50 to-20 ℃; the content of the carbon-carbon double bond in the carbon-carbon double bond-containing low molecular weight acrylic resin is 0.1-2 mmol/g.
Further, the weight average molecular weight of the high molecular weight acrylic resin containing carbon-carbon double bonds is preferably 70 to 100 tens of thousands; the weight average molecular weight of the low molecular weight acrylic resin containing carbon-carbon double bonds is preferably 10 to 30 ten thousand.
Further, the reaction raw materials of the high molecular weight acrylic resin containing carbon-carbon double bonds comprise the following components in parts by weight: 50-80 parts of soft monomer, 0-20 parts of hard monomer, 5-15 parts of functional monomer, 5-25 parts of functional monomer containing active hydroxyl, 0.02-0.5 part of first initiator, 0.01-1 part of catalyst, 3-30 parts of isocyanate containing carbon-carbon double bond and 50-210 parts of first solvent; the first initiator is azodiisobutyronitrile, and the first solvent is ethyl acetate and/or butyl acetate;
further, the reaction raw materials of the low molecular weight acrylic resin containing carbon-carbon double bonds comprise the following components in parts by weight: 40-70 parts of soft monomer, 3-8 parts of hard monomer, 7-15 parts of functional monomer, 5-30 parts of functional monomer containing active hydroxyl, 0.02-0.5 part of second initiator, 0.01-1 part of catalyst, 7-35 parts of isocyanate containing carbon-carbon double bond and 50-210 parts of second solvent; the second initiator is benzoyl peroxide, and the second solvent is toluene and/or heptane.
Further, the soft monomer is alkyl acrylate, and the carbon number of the alkyl is an integer of 1-12.
Further, the soft monomer is preferably one or more of methyl acrylate, ethyl acrylate, butyl acrylate and isooctyl acrylate.
Further, the hard monomer is alkyl methacrylate, and the carbon number of the alkyl is an integer of 1 to 6.
Further, the hard monomer is preferably one or more of methyl methacrylate, ethyl methacrylate and butyl methacrylate.
Further, the functional monomer is one or more of acrylic acid, methacrylic acid, N-methylolacrylamide, glycidyl acrylate and N, N-dimethylacrylamide.
Further, the functional monomer containing active hydroxyl is one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, 4-hydroxybutyl acrylate and 4-hydroxybutyl methacrylate.
Further, the initiator is one or more of benzoyl peroxide, azodiisobutyronitrile, di-tert-butyl hydroperoxide and tert-butyl peroxy-2-ethylhexanoic acid.
Further, the catalyst is one or more of dioctyltin laurate, dibutyl tin dilaurate and zirconium acetylacetonate.
Further, the isocyanate containing carbon-carbon double bonds is isocyanate ethyl acrylate and/or isocyanate ethyl methacrylate.
Further, the isocyanate containing carbon-carbon double bond is added in the same molar amount as the functional monomer containing active hydroxyl group. The isocyanate containing a carbon-carbon double bond reacts with the hydroxyl group on the hydroxyl group-containing acrylic resin chain to introduce the carbon-carbon double bond to the acrylic resin chain.
Further, the preparation method of the high molecular weight acrylic resin containing carbon-carbon double bonds and the low molecular weight acrylic resin containing carbon-carbon double bonds comprises the following steps:
(1) Mixing soft monomer, hard monomer, functional monomer and functional monomer containing active hydroxyl with solvent under inert atmosphere, heating to reflux temperature under stirring, adding initiator step by step and preserving heat for 2-8 h, and cooling the reaction solution to 40-60 ℃;
(2) Adding a catalyst into the reaction liquid cooled in the step (1), dropwise adding a mixed liquid of isocyanate containing carbon-carbon double bonds and the residual solvent under the stirring condition, and reacting for 3-5 h to obtain the high molecular weight/low molecular weight acrylic resin containing carbon-carbon double bonds;
the weight average molecular weight of the high molecular weight acrylic resin containing carbon-carbon double bonds is 50-100 ten thousand, and the weight average molecular weight of the low molecular weight acrylic resin containing carbon-carbon double bonds is 5-40 ten thousand.
The preparation method of the acrylic resin containing carbon-carbon double bonds with different molecular weights is the same, and the molecular weight of the acrylic resin is regulated and controlled mainly by regulating the types and the addition amount of the initiator and the solvent.
Further, in the step (1), part of the initiator is added, the temperature is kept for 1 to 3 hours, then the rest of the initiator is added, and the temperature is kept for 1 to 5 hours.
Further, in the step (2), the time of the dripping is 0.1-1 h.
Further, the photoinitiator is one or more of benzil dimethyl ether, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 4-p-phenylmercapto benzophenone, 4-methylbenzophenone, isopropylthioxanthene and 2-ethyl anthraquinone.
Further, the thermosetting agent is one or more of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate and hexamethylene diisocyanate.
Further, the organic solvent is one or more of dimethyl ether, dipropylene glycol methyl ether, ethyl acetate, toluene, butyl acetate and heptane.
The second aspect of the invention provides a preparation method of the UV-curable adhesive of the first aspect, which comprises the steps of uniformly mixing a high molecular weight acrylic resin containing carbon-carbon double bonds, a low molecular weight acrylic resin containing carbon-carbon double bonds, a photoinitiator, a thermosetting agent and an organic solvent, standing and defoaming to obtain the UV-curable adhesive.
In a third aspect the present invention provides a UV reducing adhesive tape comprising the UV reducing adhesive of the first aspect.
Compared with the prior art, the invention has the beneficial effects that:
1. the UV adhesive-reducing adhesive comprises acrylic resins with different molecular weights, wherein the low-molecular-weight acrylic resin has good wettability to a substrate of an object to be adhered, so that the initial adhesion and the stripping force of an adhesive tape prepared by the adhesive are improved; the introduced high molecular weight acrylic resin and low molecular weight acrylic resin form an interpenetrating structure, thereby overcoming the defect of generating residual glue on the attached object during stripping. In addition, compared with the high-molecular-weight acrylic resin adhesive with the same solid content, the viscosity of the low-molecular-weight acrylic resin adhesive is obviously reduced, the coating and the use are convenient, the introduction of a multifunctional reactive diluent is not needed, the pollution to the attached object caused by the migration of the diluent in the attaching process of the attached object is avoided, and the product yield is improved.
2. The UV-curable adhesive prepared by the invention contains acrylic resins containing carbon-carbon double bonds with different molecular weights, and after being irradiated by a UV light source, the photoinitiator initiates double bond polymerization crosslinking, so that obvious volume shrinkage is generated, and the stripping force is reduced.
3. The adhesive-reducing tape prepared from the UV adhesive-reducing adhesive has strong initial adhesion, good holding viscosity, large peeling of an object to be adhered before UV irradiation, rapid decrease of the adhesive property after UV irradiation, easy peeling, and no residual adhesive after peeling before and after UV irradiation.
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 herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
The present invention will be further described with reference to specific examples, which are not intended to be limiting, so that those skilled in the art will better understand the present invention and practice it.
Example 1
This example relates to the synthesis of acrylic esters of carbon-carbon double bonds of different molecular weights, in particular as follows:
1. the synthesis of the acrylic resin liquid 1 comprises the following steps:
(1) Uniformly mixing 40 parts of isooctyl acrylate, 30 parts of butyl acrylate, 15 parts of methyl methacrylate, 10 parts of hydroxyethyl acrylate, 5 parts of N, N-dimethylacrylamide and 100 parts of ethyl acetate, stirring and heating to 66 ℃ under nitrogen atmosphere, adding 0.02 part of azo-diisobutyronitrile serving as an initiator, preserving heat for 2 hours, adding 0.01 part of an initiator, heating to 76 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (3) adding 0.02 part of dibutyltin dilaurate into the reaction liquid treated in the step (1), stopping introducing nitrogen, dropwise adding a mixed liquid of 12.15 parts of isocyanate ethyl acrylate and 12.15 parts of ethyl acetate into the reaction liquid for half an hour under stirring, preserving heat for 5 hours, cooling and discharging to obtain the carbon-carbon double bond-containing high molecular weight acrylate resin liquid 1.
2. The synthesis of the acrylic resin liquid 2 comprises the following steps:
(1) Uniformly mixing 30 parts of isooctyl acrylate, 35 parts of butyl acrylate, 10 parts of methyl methacrylate, 5 parts of acrylic acid, 15 parts of hydroxyethyl acrylate, 5 parts of N, N-dimethylacrylamide and 100 parts of ethyl acetate, stirring and heating to 66 ℃ under a nitrogen atmosphere, adding 0.02 part of azo-diisobutyronitrile serving as an initiator, preserving heat for 2 hours, adding 0.01 part of an initiator, heating to 76 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (3) adding 0.03 part of dibutyltin dilaurate into the reaction solution treated in the step (1), stopping introducing nitrogen, dropwise adding the mixed solution of 18.23 parts of isocyanate ethyl acrylate and 18.23 parts of ethyl acetate into the reaction solution for half an hour under stirring, preserving heat for 5 hours, cooling and discharging to obtain the carbon-carbon double bond-containing high molecular weight acrylate resin solution 2.
3. The synthesis of the acrylic resin liquid 3 comprises the following steps:
(1) Uniformly mixing 40 parts of isooctyl acrylate, 40 parts of butyl acrylate, 10 parts of 4-hydroxybutyl acrylate, 10 parts of N, N-dimethylacrylamide and 100 parts of ethyl acetate, stirring and heating to 66 ℃ under nitrogen atmosphere, adding 0.02 part of azo-diisobutyronitrile serving as an initiator, preserving heat for 2 hours, adding 0.01 part of an initiator, heating to 76 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (3) adding 0.02 part of dibutyltin dilaurate into the reaction solution treated in the step (1), stopping introducing nitrogen, dropwise adding 9.79 parts of mixed solution of isocyanate ethyl acrylate and 9.79 parts of ethyl acetate into the reaction solution for half an hour under stirring, preserving heat for 4 hours, cooling and discharging to obtain the high-molecular-weight acrylate resin solution 3 containing carbon-carbon double bonds.
4. The synthesis of the acrylic resin liquid 4 comprises the following steps:
(1) Uniformly mixing 40 parts of isooctyl acrylate, 15 parts of butyl acrylate, 5 parts of methyl methacrylate, 10 parts of hydroxyethyl acrylate, 10 parts of N, N-dimethylacrylamide and 100 parts of toluene, stirring and heating to 70 ℃ under a nitrogen atmosphere, adding 0.04 part of benzoyl peroxide serving as an initiator, preserving heat for 2 hours, adding 0.01 part of an initiator, heating to 80 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (3) adding 0.02 part of dibutyltin dilaurate into the reaction solution treated in the step (1), stopping introducing nitrogen, dropwise adding a mixed solution of 12.15 parts of isocyanate ethyl acrylate and 12.15 parts of ethyl acetate into the reaction solution for half an hour under stirring, preserving heat for 5 hours, cooling and discharging to obtain the carbon-carbon double bond-containing low molecular weight acrylate resin solution 4.
5. The synthesis of the acrylic resin liquid 5 comprises the following steps:
(1) Uniformly mixing 30 parts of isooctyl acrylate, 35 parts of butyl acrylate, 5 parts of methyl methacrylate, 20 parts of hydroxyethyl acrylate, 10 parts of N, N-dimethylacrylamide and 100 parts of toluene, stirring and heating to 70 ℃ under a nitrogen atmosphere, adding 0.03 part of benzoyl nitrile peroxide serving as an initiator, preserving heat for 2 hours, adding 0.01 part of initiator, heating to 80 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (3) adding 0.04 part of dibutyltin dilaurate into the reaction liquid treated in the step (1), stopping introducing nitrogen, dropwise adding the mixed liquid of 24.3 parts of isocyanate ethyl acrylate and 24.3 parts of ethyl acetate into the reaction liquid for half an hour under stirring, preserving heat for 5 hours, cooling and discharging to obtain the carbon-carbon double bond-containing low molecular weight acrylate resin liquid 5.
6. The synthesis of the acrylic resin liquid 6 comprises the following steps:
(1) Uniformly mixing 30 parts of isooctyl acrylate, 33 parts of butyl acrylate, 30 parts of 4-hydroxybutyl acrylate, 2 parts of acrylic acid, 5 parts of N, N-dimethylacrylamide and 100 parts of toluene, stirring and heating to 70 ℃ under a nitrogen atmosphere, adding 0.03 part of initiator benzoyl peroxide, preserving heat for 2 hours, adding 0.01 part of initiator, heating to 80 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (3) adding 0.05 part of dibutyltin dilaurate into the reaction solution treated in the step (1), stopping introducing nitrogen, dropwise adding the mixed solution of 29.37 parts of isocyanate ethyl acrylate and 29.37 parts of ethyl acetate into the reaction solution for half an hour under stirring, preserving heat for 4 hours, cooling and discharging to obtain the carbon-carbon double bond-containing low molecular weight acrylate resin solution 6.
Example 2
The embodiment relates to preparation of a UV (ultraviolet) adhesive, which comprises the following specific steps: uniformly mixing 30 parts of high molecular weight acrylic ester resin liquid 1 containing carbon-carbon double bonds, 20 parts of low molecular weight acrylic ester resin liquid 4 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide, 0.1 part of thermosetting agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV glue reducing adhesive A1.
Example 3
The embodiment relates to preparation of a UV (ultraviolet) adhesive, which comprises the following specific steps: uniformly mixing 25 parts of carbon-carbon double bond-containing high molecular weight acrylic ester resin liquid 1, 25 parts of carbon-carbon double bond-containing low molecular weight acrylic ester resin liquid 5, 0.5 part of benzil dimethyl ether, 0.12 part of thermosetting agent isophorone diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive A2.
Example 4
The embodiment relates to preparation of a UV (ultraviolet) adhesive, which comprises the following specific steps: uniformly mixing 25 parts of high molecular weight acrylic ester resin liquid 1 containing carbon-carbon double bonds, 25 parts of low molecular weight acrylic ester resin liquid 6 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide, 0.1 part of thermosetting agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive A3.
Example 5
The embodiment relates to preparation of a UV (ultraviolet) adhesive, which comprises the following specific steps: uniformly mixing 30 parts of carbon-carbon double bond-containing high molecular weight acrylic ester resin liquid 2, 20 parts of carbon-carbon double bond-containing low molecular weight acrylic ester resin liquid 5, 0.5 part of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide, 0.1 part of thermosetting agent isophorone diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV-reducing adhesive A4.
Example 6
The embodiment relates to preparation of a UV (ultraviolet) adhesive, which comprises the following specific steps: uniformly mixing 25 parts of carbon-carbon double bond-containing high molecular weight acrylic ester resin liquid 2, 25 parts of carbon-carbon double bond-containing low molecular weight acrylic ester resin liquid 5, 0.5 part of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide, 0.1 part of thermosetting agent isophorone diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV-reducing adhesive A5.
Example 7
The embodiment relates to preparation of a UV (ultraviolet) adhesive, which comprises the following specific steps: uniformly mixing 20 parts of carbon-carbon double bond-containing high molecular weight acrylic ester resin liquid 3, 30 parts of carbon-carbon double bond-containing low molecular weight acrylic ester resin liquid 6, 0.5 part of benzil dimethyl ether, 0.1 part of thermosetting agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min for defoaming, and thus obtaining the UV adhesive A6.
Comparative example 1
The comparative example relates to the preparation of a UV (ultraviolet) adhesive reducing adhesive, which comprises the following specific steps: uniformly mixing 50 parts of high molecular weight acrylic ester resin liquid 1 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermocuring agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive B1.
Comparative example 2
The comparative example relates to the preparation of a UV (ultraviolet) adhesive reducing adhesive, which comprises the following specific steps: uniformly mixing 50 parts of high molecular weight acrylic ester resin liquid 2 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of dicyclohexylmethane diisocyanate serving as a thermosetting agent and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive B2.
Comparative example 3
The comparative example relates to the preparation of a UV (ultraviolet) adhesive reducing adhesive, which comprises the following specific steps: uniformly mixing 50 parts of high molecular weight acrylic ester resin liquid 3 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermocuring agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive B3.
Comparative example 4
The comparative example relates to the preparation of a UV (ultraviolet) adhesive reducing adhesive, which comprises the following specific steps: uniformly mixing 50 parts of high molecular weight acrylic ester resin liquid 4 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermocuring agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive B4.
Comparative example 5
The comparative example relates to the preparation of a UV (ultraviolet) adhesive reducing adhesive, which comprises the following specific steps: uniformly mixing 50 parts of high molecular weight acrylic ester resin liquid 5 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermocuring agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive B5.
Comparative example 6
The comparative example relates to the preparation of a UV (ultraviolet) adhesive reducing adhesive, which comprises the following specific steps: uniformly mixing 50 parts of high molecular weight acrylic ester resin solution 6 containing carbon-carbon double bonds, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermocuring agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, standing for 30min, and defoaming to obtain the UV adhesive B6.
Performance testing
1. Performance test of the synthesized acrylic resin solutions with different molecular weights
The solid content, viscosity and weight average molecular weight of the double bond-containing acrylate resin solutions of different molecular weights synthesized in the examples were tested as follows:
solid content: reference is made to GB/T2793-1995;
viscosity: reference GB/T21059-2007;
weight average molecular weight: refer to GB/T27843-2011.
The test results are shown in table 1:
TABLE 1 results of Performance test of different acrylate resin solutions
2. Performance test of the prepared UV-curable adhesive
The UV-curable adhesive prepared in the above examples and comparative examples was coated on PO substrates having a thickness of 150 μm, respectively, with a coating amount of 40g/cm 2 Baking at 80deg.C for 4min to form uniform coating with thickness of 10 μm, standing at 45deg.C for 72 hr, adhering PO film coated with the reduced adhesive on SUS304 steel plate, and irradiating with ultraviolet lamp for 5s with ultraviolet light intensity of 300mJ/cm 2 And (5) standby test. The initial adhesion, holding adhesion, peel strength before and after UV irradiation and residual adhesive phenomenon after peeling were tested for different UV-reduced adhesives, and the test criteria were as follows:
initial tack test: referring to GB/T4852-2002, the ball ramp is stopped experimentally, at a 30℃tilt angle.
Hold tack test: with reference to GB/T4851-1998, the adhesion tester was tested at 80℃with a weight of 1kg.
180 ° peel strength: with reference to GB/T2792-1998, the electronic tensile tester was 25mm wide with a tape width and a peel rate of 300mm/min.
The test results are shown in table 2:
TABLE 2 Performance test values for different UV-reduced adhesives
As can be seen from the performance test data in Table 2, comparative examples 1 to 3 were UV-curable adhesives B1 to B3 prepared from a single high molecular weight acrylic resin having a carbon-carbon double bond, which had no adhesive residue after peeling before and after UV irradiation, but the adhesive-curable tapes prepared therefrom had a small initial adhesion, a small peeling force before UV irradiation, and a relatively large peeling force after UV irradiation. The UV-curable adhesive B4-B6 prepared by adopting the single low-molecular-weight acrylic resin containing carbon-carbon double bonds in comparative examples 4-6 has higher initial adhesiveness, but has low cohesive force, is easy to generate cohesive failure in the peeling process, causes the phenomenon of adhesive residue, has insufficient holding adhesiveness, and has displacement phenomenon.
Examples 2-7 are UV-curable adhesives prepared from high molecular weight acrylic resin containing carbon-carbon double bonds and low molecular weight acrylic resin containing carbon-carbon double bonds, which can achieve synergistic enhancement effect, not only improve the initial adhesion of UV-curable adhesives, but also have good holding viscosity, and solve the problem of residual adhesives caused by cohesive failure; in addition, the prepared UV-curable adhesive A1-A6 has large stripping force before UV irradiation and no cohesive problem, and the stripping force after UV irradiation is rapidly reduced and is easy to strip. In addition, the UV adhesive does not contain flatting agents and the like, can not pollute the attached object in the attaching process, and meets the performance requirements of the UV adhesive tape in the fine processing process of semiconductor chips, transistors, integrated circuits, printed circuit boards, optical microscopes and the like.
The above-described embodiments are merely preferred embodiments for fully explaining the present invention, and the scope of the present invention is not limited thereto. Equivalent substitutions and modifications will occur to those skilled in the art based on the present invention, and are intended to be within the scope of the present invention. The protection scope of the invention is subject to the claims.
Claims (5)
1. The UV adhesive is characterized by comprising the following components in parts by weight: 10-40 parts of carbon-carbon double bond-containing high-molecular-weight acrylic resin, 10-40 parts of carbon-carbon double bond-containing low-molecular-weight acrylic resin, 0.5-3 parts of photoinitiator, 0.01-1 part of thermosetting agent and 30-50 parts of organic solvent;
the weight average molecular weight of the high molecular weight acrylic resin containing carbon-carbon double bonds is 50-100 ten thousand, and the glass transition temperature is-50 to-20 ℃; the content of the carbon-carbon double bond in the carbon-carbon double bond-containing high molecular weight acrylic resin is 0.1-2 mmol/g;
the weight average molecular weight of the low molecular weight acrylic resin containing carbon-carbon double bonds is 5-40 ten thousand, and the glass transition temperature is-50 to-20 ℃; the content of the carbon-carbon double bond in the carbon-carbon double bond-containing low molecular weight acrylic resin is 0.1-2 mmol/g;
the reaction raw materials of the high molecular weight acrylic resin containing carbon-carbon double bonds comprise the following components in parts by weight: 50-80 parts of soft monomer, 0-20 parts of hard monomer, 5-15 parts of functional monomer, 5-25 parts of functional monomer containing active hydroxyl, 0.02-0.5 part of first initiator, 0.01-1 part of catalyst, 3-30 parts of isocyanate containing carbon-carbon double bond and 50-210 parts of first solvent; the first initiator is azodiisobutyronitrile, and the first solvent is ethyl acetate and/or butyl acetate;
the reaction raw materials of the low molecular weight acrylic resin containing carbon-carbon double bonds comprise the following components in parts by weight: 40-70 parts of soft monomer, 3-8 parts of hard monomer, 7-15 parts of functional monomer, 5-30 parts of functional monomer containing active hydroxyl, 0.02-0.5 part of second initiator, 0.01-1 part of catalyst, 7-35 parts of isocyanate containing carbon-carbon double bond and 50-210 parts of second solvent; the second initiator is benzoyl peroxide, and the second solvent is toluene and/or heptane;
the soft monomer is one or more of ethyl acrylate, butyl acrylate and isooctyl acrylate; the hard monomer is one or more of methyl methacrylate, ethyl methacrylate and butyl methacrylate;
the functional monomer is one or more of acrylic acid, methacrylic acid, N-methylolacrylamide, glycidyl acrylate and N, N-dimethylacrylamide;
the functional monomer containing active hydroxyl is one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, 4-hydroxybutyl acrylate and 4-hydroxybutyl methacrylate;
the isocyanate containing carbon-carbon double bonds is isocyanate ethyl acrylate and/or isocyanate ethyl methacrylate; the molar quantity of the isocyanate containing carbon-carbon double bonds is the same as that of the functional monomer containing active hydroxyl;
the preparation method of the high molecular weight/low molecular weight acrylic resin containing carbon-carbon double bonds comprises the following steps:
(1) Mixing a soft monomer, a hard monomer, a functional monomer containing active hydroxyl and a solvent under an inert atmosphere, heating to a reflux temperature under a stirring condition, adding an initiator step by step, preserving heat for 2-8 h, and cooling a reaction solution to 40-60 ℃;
(2) Adding a catalyst into the reaction liquid cooled in the step (1), dropwise adding a mixed liquid of isocyanate containing carbon-carbon double bonds and the residual solvent under the stirring condition, and reacting for 3-5 h to obtain the high molecular weight/low molecular weight acrylic resin containing carbon-carbon double bonds; the dripping time is 0.1-1 h.
2. The UV reducing adhesive according to claim 1, wherein the catalyst is one or more of dioctyltin laurate, dibutyltin dilaurate, and zirconium acetylacetonate.
3. The UV-reducing adhesive according to claim 1, wherein the photoinitiator is one or more of benzil dimethyl ether, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 4-p-phenylmercapto benzophenone, 4-methylbenzophenone, isopropylthioxanthene, 2-ethylanthraquinone;
the thermosetting agent is one or more of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate and hexamethylene diisocyanate;
the organic solvent is one or more of dimethyl ether, dipropylene glycol methyl ether, ethyl acetate, toluene, butyl acetate and heptane.
4. A method for preparing the UV-reducing adhesive according to any one of claims 1 to 3, wherein the UV-reducing adhesive is obtained by uniformly mixing a high molecular weight acrylic resin containing carbon-carbon double bonds, a low molecular weight acrylic resin containing carbon-carbon double bonds, a photoinitiator, a thermosetting agent and an organic solvent, and standing for defoaming.
5. A UV reducing adhesive tape, characterized in that the UV reducing adhesive tape comprises the UV reducing adhesive according to any one of claims 1 to 3.
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| CN108300352A (en) * | 2018-02-02 | 2018-07-20 | 苏州城邦达力材料科技有限公司 | A kind of UV visbreakings composition of acid and alkali-resistance, UV visbreaking films and preparation method thereof |
| CN108864957A (en) * | 2018-06-29 | 2018-11-23 | 新纶科技（常州）有限公司 | A kind of preparation method of the adjustable UV visbreaking pressure sensitive adhesive of peeling force |
| CN110591611A (en) * | 2019-09-20 | 2019-12-20 | 上海精珅新材料有限公司 | UV (ultraviolet) viscosity-reducing protective film glue with reduced viscosity at high temperature and protective film production method thereof |
| 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 |
| CN114231205A (en) * | 2021-12-31 | 2022-03-25 | 深圳市云启科技有限公司 | Heat-resistant UV (ultraviolet) viscosity-reducing adhesive tape |
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