CN115232578A - UV viscosity-reducing adhesive and preparation method thereof - Google Patents
UV viscosity-reducing adhesive and preparation method thereof Download PDFInfo
- Publication number
- CN115232578A CN115232578A CN202210987973.3A CN202210987973A CN115232578A CN 115232578 A CN115232578 A CN 115232578A CN 202210987973 A CN202210987973 A CN 202210987973A CN 115232578 A CN115232578 A CN 115232578A
- Authority
- CN
- China
- Prior art keywords
- carbon
- molecular weight
- double bond
- parts
- carbon double
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 75
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 75
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 87
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 83
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 51
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 238000001029 thermal curing Methods 0.000 claims abstract description 19
- 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 36
- 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
- 239000012295 chemical reaction liquid Substances 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- 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 9
- 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
- 239000011259 mixed solution Substances 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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 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
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 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
- -1 alkyl methacrylate Chemical compound 0.000 claims description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 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
- 239000002994 raw material Substances 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 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
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 2
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-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
- 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
- 125000005250 alkyl acrylate group Chemical group 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
- 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
- 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 1
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 abstract description 12
- 239000003292 glue Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 10
- 239000002390 adhesive tape Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000007599 discharging Methods 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 230000008569 process Effects 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
- 238000004132 cross linking Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000003287 optical effect Effects 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
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001723 curing Methods 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
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005096 rolling process Methods 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
- 238000010998 test method Methods 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 viscosity-reducing adhesive and a preparation method thereof, wherein the UV viscosity-reducing adhesive comprises the following components in parts by weight: 10 to 40 portions of carbon-carbon double bond containing high molecular weight acrylic resin, 10 to 40 portions of carbon-carbon double bond containing low molecular weight acrylic resin, 0.5 to 3 portions of photoinitiator, 0.01 to 1 portion of thermal curing agent and 30 to 50 portions 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 visbreaking glue prepared by the invention utilizes the low molecular weight acrylic resin to improve the initial adhesion force and the stripping force of the UV visbreaking glue, and an interpenetrating structure is formed by the high molecular weight acrylic resin and the low molecular weight acrylic resin, so that the phenomenon of glue residue during stripping is avoided, and simultaneously, the carbon-carbon double bond of the acrylic resin body is polymerized and crosslinked after UV irradiation to generate larger volume shrinkage so as to reduce the stripping force.
Description
Technical Field
The invention relates to the technical field of adhesives, and particularly relates to a UV viscosity-reducing adhesive and a preparation method thereof.
Background
The UV anti-adhesive tape should have high adhesion before UV irradiation and good adhesion, and when separation is required, after UV irradiation for a short time, the adhesion is greatly reduced and easy to tear, so that it is widely used in the manufacturing process of products such as semiconductor chips, transistors, integrated circuits, printed circuit boards, optical microscopes, and the like.
However, most of the UV visbreaking adhesives in the current market are formed by mixing an acrylate polymer adhesive and then adding a multifunctional reactive diluent, a photoinitiator and a curing agent, but in the method, most of the reactive diluents are small molecules, and after the adhesive tape is attached to an attached object, the compatibility in the system is limited, so that the migration of the small molecule reactive diluents to the interface of the attached object is caused, the initial viscosity and the stripping force are reduced, and the adhesive is easy to remain after crosslinking; in addition, the UV viscosity-reducing adhesive has the problem of low initial adhesion after the preparation of the viscosity-reducing tape, so that the adhesion is difficult. At present, the initial adhesion of the adhesive tape is improved by reducing the weight average molecular weight, but the adhesive tape can have the adhesive residue phenomenon when an object to be pasted is peeled off after the weight average molecular weight is reduced; although the defect of residual adhesive can be improved by the excessively high weight-average molecular weight, the peeling strength of the adhesive tape on an adhered object is reduced, the fixing, protecting, adhering and conveying functions of the UV adhesive-reducing tape in the manufacturing process of the semiconductor wafer are reduced, and the UV adhesive-reducing tape is easy to displace so as to scrap products.
Disclosure of Invention
The invention aims to solve the technical problem of providing a UV (ultraviolet) viscosity-reducing adhesive and a preparation method thereof.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention provides a UV viscosity-reducing adhesive which comprises the following components in parts by weight: 10 to 40 parts of high molecular weight acrylic resin containing carbon-carbon double bonds, 10 to 40 parts of low molecular weight acrylic resin containing carbon-carbon double bonds, 0.5 to 3 parts of photoinitiator, 0.01 to 1 part of thermal curing 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 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 carbon-carbon double bond-containing low molecular weight acrylic resin is 5-40 ten thousand, and the glass transition temperature is-50 to-20 ℃; the content of the carbon-carbon double bond in the low molecular weight acrylic resin containing the carbon-carbon double bond is 0.1-2 mmol/g.
Further, the weight average molecular weight of the carbon-carbon double bond-containing high molecular weight acrylic resin is preferably 70 to 100 ten thousand; 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 material of the carbon-carbon double bond-containing high molecular weight acrylic resin comprises 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 azobisisobutyronitrile, and the first solvent is ethyl acetate and/or butyl acetate;
further, the reaction raw material of the low molecular weight acrylic resin containing carbon-carbon double bonds comprises 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 number of carbon atoms of the alkyl group is an integer of 1 to 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 number of carbon atoms of the alkyl group 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-hydroxymethyl acrylamide, 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, azobisisobutyronitrile, di-tert-butyl hydroperoxide and tert-butyl peroxy-2-ethyl hexanoic acid.
Further, the catalyst is one or more of dioctyltin laurate, dibutyltin dilaurate and zirconium acetylacetonate.
Further, the isocyanate containing the carbon-carbon double bond is isocyanate ethyl acrylate and/or isocyanate ethyl methacrylate.
Further, the isocyanate containing carbon-carbon double bond and the functional monomer containing active hydroxyl are added in the same molar amount. The isocyanate containing carbon-carbon double bonds reacts with the hydroxyl groups on the acrylic resin chain containing hydroxyl groups to introduce the carbon-carbon double bonds into 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 a soft monomer, a hard monomer, a functional monomer containing active hydroxyl and a solvent in an inert atmosphere, heating to a reflux temperature under the condition of stirring, adding an initiator step by step, preserving heat for 2-8 hours, 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 solution of isocyanate containing carbon-carbon double bonds and the rest solvent under the stirring condition, and reacting for 3-5 hours 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 the carbon-carbon double bond is 50-100 ten thousand, and the weight average molecular weight of the low molecular weight acrylic resin containing the carbon-carbon double bond 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 adding amounts of the initiator and the solvent.
Further, in the step (1), part of the initiator is added firstly, the temperature is kept for 1 to 3 hours, the rest of the initiator is added, and the temperature is kept for 1 to 5 hours.
Further, in the step (2), the dropping time is 0.1 to 1 hour.
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-trimethyl benzoyl-diphenyl phosphine oxide, 4-p-phenyl mercapto benzophenone, 4-methyl benzophenone, isopropyl thia-anthracene and 2-ethyl anthraquinone.
Further, the thermal curing 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 dimethanol methyl 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 viscosity-reducing adhesive of the first aspect, wherein the UV viscosity-reducing adhesive is prepared by uniformly mixing carbon-carbon double bond-containing high molecular weight acrylic resin, carbon-carbon double bond-containing low molecular weight acrylic resin, a photoinitiator, a thermal curing agent and an organic solvent, and standing for defoaming.
The invention provides a UV visbreaking adhesive tape in a third aspect, which comprises the UV visbreaking adhesive in the first aspect.
Compared with the prior art, the invention has the beneficial effects that:
1. the UV viscosity-reducing adhesive comprises acrylic resins with different molecular weights, wherein the low-molecular-weight acrylic resin has good wettability on a substrate of an adhered object, so that the initial adhesion force and the stripping force of an adhesive tape prepared from the adhesive are improved; the introduced high molecular weight acrylic resin and the low molecular weight acrylic resin form an interpenetrating structure, and the defect of generating residual glue on a stuck object during stripping is overcome. In addition, compared with high-molecular-weight acrylic resin adhesive with the same solid content, the low-molecular-weight acrylic resin adhesive has the advantages that the viscosity is obviously reduced, the coating and the use are convenient, a multifunctional reactive diluent is not required to be introduced, the attached object is not polluted due to the migration of the diluent in the process of attaching the attached object, and the product yield is improved.
2. The UV viscosity-reducing adhesive prepared by the invention contains acrylic resin containing carbon-carbon double bonds with different molecular weights, and after the UV light source irradiates, the photoinitiator initiates double bond polymerization crosslinking, so that obvious volume shrinkage is generated, and the stripping force is reduced.
3. The anti-sticking adhesive tape prepared from the UV anti-sticking adhesive has strong initial adhesion and good permanent adhesion, can peel an adhered object greatly before UV irradiation, is quickly reduced in adhesion after UV irradiation and easy to peel, and has no adhesive residue 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 in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The present invention is further described below with reference to specific examples so that those skilled in the art can better understand the present invention and can practice the present invention, but the examples are not intended to limit the present invention.
Example 1
The present example relates to the synthesis of carbon-carbon double bond acrylates of different molecular weights, as follows:
1. the synthesis of the acrylate 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 ℃ in a nitrogen atmosphere, adding 0.02 part of azodiisobutyronitrile serving as an initiator, keeping the temperature for 2 hours, adding 0.01 part of the initiator, heating to 76 ℃, keeping the temperature for 3 hours, and cooling to 50 ℃.
(2) And (2) adding 0.02 part of dibutyltin dilaurate into the reaction liquid 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 liquid for half an hour under the stirring condition, 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 acrylate 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 ℃ in a nitrogen atmosphere, adding 0.02 part of azodiisobutyronitrile serving as an initiator, preserving heat for 2 hours, adding 0.01 part of the initiator, heating to 76 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (2) adding 0.03 part of dibutyltin dilaurate into the reaction liquid treated in the step (1), stopping introducing nitrogen, dropwise adding a mixed solution of 18.23 parts of isocyanate ethyl acrylate and 18.23 parts of ethyl acetate into the reaction liquid for half an hour under the stirring condition, preserving heat for 5 hours, and cooling and discharging to obtain the carbon-carbon double bond-containing high molecular weight acrylate resin liquid 2.
3. The synthesis of the acrylate 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 the atmosphere of nitrogen, adding 0.02 part of azodiisobutyronitrile serving as an initiator, preserving heat for 2 hours, adding 0.01 part of the initiator, heating to 76 ℃, preserving heat for 3 hours, and cooling to 50 ℃.
(2) And (2) adding 0.02 part of dibutyltin dilaurate into the reaction liquid treated in the step (1), stopping introducing nitrogen, dropwise adding a mixed solution of 9.79 parts of isocyanate ethyl acrylate and 9.79 parts of ethyl acetate into the reaction liquid for half an hour under the stirring condition, preserving heat for 4 hours, and cooling and discharging to obtain the carbon-carbon double bond-containing high molecular weight acrylate resin liquid 3.
4. The synthesis of the acrylate 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 ℃ in a nitrogen atmosphere, adding 0.04 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 (2) adding 0.02 part of dibutyltin dilaurate into the reaction liquid 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 liquid for half an hour under the stirring condition, preserving heat for 5 hours, cooling and discharging to obtain the carbon-carbon double bond-containing low-molecular-weight acrylate resin liquid 4.
5. The synthesis of the acrylate 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 ℃ in a nitrogen atmosphere, adding 0.03 part of initiator benzoyl peroxide nitrile, 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 (2) adding 0.04 part of dibutyltin dilaurate into the reaction liquid treated in the step (1), stopping introducing nitrogen, dropwise adding a mixed solution of 24.3 parts of isocyanate ethyl acrylate and 24.3 parts of ethyl acetate into the reaction liquid for half an hour under the stirring condition, preserving heat for 5 hours, and cooling and discharging to obtain the carbon-carbon double bond-containing low-molecular-weight acrylate resin liquid 5.
6. The synthesis of the acrylate 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 ℃ in 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 (2) adding 0.05 part of dibutyltin dilaurate into the reaction liquid treated in the step (1), stopping introducing nitrogen, dropwise adding a mixed solution of 29.37 parts of isocyanate ethyl acrylate and 29.37 parts of ethyl acetate into the reaction liquid for half an hour under the stirring condition, preserving heat for 4 hours, cooling and discharging to obtain the carbon-carbon double bond-containing low-molecular-weight acrylate resin liquid 6.
Example 2
The embodiment relates to a preparation method of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 30 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 1, 20 parts of carbon-carbon double bond-containing low molecular weight acrylate resin liquid 4, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive A1.
Example 3
The embodiment relates to a preparation method of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 25 parts of carbon-carbon double bond containing high molecular weight acrylate resin liquid 1, 25 parts of carbon-carbon double bond containing low molecular weight acrylate resin liquid 5, 0.5 part of benzil dimethyl ether, 0.12 part of thermal curing agent isophorone diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive A2.
Example 4
The embodiment relates to a preparation method of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 25 parts of carbon-carbon double bond-containing high-molecular-weight acrylate resin liquid 1, 25 parts of carbon-carbon double bond-containing low-molecular-weight acrylate resin liquid 6, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive A3.
Example 5
The embodiment relates to a preparation method of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 30 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 2, 20 parts of carbon-carbon double bond-containing low molecular weight acrylate resin liquid 5, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, 0.1 part of thermal curing agent isophorone diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive A4.
Example 6
The embodiment relates to a preparation method of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 25 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 2, 25 parts of carbon-carbon double bond-containing low molecular weight acrylate resin liquid 5, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of thermal curing agent isophorone diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive A5.
Example 7
The embodiment relates to a preparation method of a UV viscosity-reducing adhesive, which specifically comprises the following steps: and (3) uniformly mixing 20 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 3, 30 parts of carbon-carbon double bond-containing low molecular weight acrylate resin liquid 6, 0.5 part of benzil dimethyl ether, 0.1 part of thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive A6.
Comparative example 1
The comparative example relates to preparation of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 50 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 1, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of a thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive B1.
Comparative example 2
The comparative example relates to preparation of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 50 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 2, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of a thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive B2.
Comparative example 3
The comparative example relates to preparation of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 50 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 3, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of a thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive B3.
Comparative example 4
The comparative example relates to preparation of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 50 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 4, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of a thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive B4.
Comparative example 5
The comparative example relates to preparation of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 50 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 5, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of a thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive B5.
Comparative example 6
The comparative example relates to preparation of a UV viscosity-reducing adhesive, which specifically comprises the following steps: uniformly mixing 50 parts of carbon-carbon double bond-containing high molecular weight acrylate resin liquid 6, 0.5 part of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 0.1 part of a thermal curing agent dicyclohexylmethane diisocyanate and 50 parts of ethyl acetate, and standing for 30min for defoaming to obtain the UV viscosity-reducing adhesive B6.
Performance testing
1. The performance test is carried out on the synthesized acrylate resin liquid with different molecular weights
The solid content, viscosity and weight average molecular weight of the double bond-containing acrylate resin liquids with different molecular weights synthesized in the examples are tested according to the following test standards:
solid content: reference GB/T2793-1995;
viscosity: reference GB/T21059-2007;
weight average molecular weight: reference is made to GB/T27843-2011.
The test results are shown in table 1:
TABLE 1 Performance test results for different acrylate resin solutions
2. Performing performance test on the prepared UV viscosity-reducing adhesive
The UV visbreaking adhesives prepared in the above examples and comparative examples were respectively coated on PO substrates with a thickness of 150 μm, and the coating amount was 40g/cm 2 Baking at 80 deg.C for 4min to form a uniform coating with thickness of 10 μm, standing at 45 deg.C for 72 hr, sticking PO film coated with viscose reducing agent on SUS304 steel plate, and usingUltraviolet lamp irradiating for 5s, ultraviolet light intensity 300mJ/cm 2 And (5) testing for standby. Testing the initial viscosity, the permanent viscosity and the peeling strength before and after UV irradiation of different UV viscosity-reducing adhesives and observing whether the residual adhesive phenomenon exists after peeling, wherein the testing standards are as follows:
initial tack testing: reference is made to GB/T4852-2002, rolling ball ramp stop test method, 30 ° tilt angle.
Tack-holding test: referring to GB/T4851-1998, a viscosity tester with a test temperature of 80 ℃ and a weight of 1kg.
180 ° peel strength: referring to GB/T2792-1998, an electronic tensile tester with a tape width of 25mm and a peeling rate of 300mm/min.
The test results are shown in table 2:
TABLE 2 Performance test values for different UV visbreaking adhesives
As can be seen from the performance test data in Table 2, the UV visbreaking adhesives B1-B3 prepared by using the acrylate resin with single high molecular weight and carbon-carbon double bond in the comparative examples 1-3 have no residual adhesive after stripping before and after UV irradiation, but the visbreaking tapes prepared by using the UV visbreaking adhesives have small initial adhesion, small stripping force before UV irradiation and relatively large stripping force after UV irradiation. Comparative examples 4 to 6 UV visbreaking adhesives B4 to B6 prepared from single low molecular weight acrylic resin containing carbon-carbon double bonds have high initial viscosity, but low cohesive force, and are easy to generate cohesive failure in the stripping process to cause adhesive residue, and the adhesive retaining property is insufficient to cause displacement.
In the embodiments 2 to 7, the UV visbreaking adhesive prepared by using the high molecular weight acrylate resin containing carbon-carbon double bonds and the low molecular weight acrylate resin containing carbon-carbon double bonds can realize a synergistic enhancement effect, not only improves the initial adhesion of the UV visbreaking adhesive, has good cohesive property, but also solves the problem of adhesive residue caused by cohesive failure; in addition, the prepared UV viscosity-reducing adhesives A1-A6 have large stripping force before UV irradiation and no cohesion problem, and the stripping force after UV irradiation is sharply reduced and easy to strip. In addition, the UV viscosity-reducing adhesive prepared by the invention does not contain a leveling agent and the like, does not pollute an attached object in the process of attaching the attached object, and meets the performance requirements of the UV viscosity-reducing adhesive tape in the fine processing processes of semiconductor chips, transistors, integrated circuits, printed circuit boards, optical microscopes and the like.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (10)
1. The UV viscosity-reducing adhesive is characterized by comprising the following components in parts by weight: 10 to 40 portions of carbon-carbon double bond containing high molecular weight acrylic resin, 10 to 40 portions of carbon-carbon double bond containing low molecular weight acrylic resin, 0.5 to 3 portions of photoinitiator, 0.01 to 1 portion of thermal curing agent and 30 to 50 portions 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 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 carbon-carbon double bond-containing low molecular weight acrylic resin 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.
2. The UV viscosity-reducing adhesive according to claim 1, wherein 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 azobisisobutyronitrile, and the first solvent is ethyl acetate and/or butyl acetate;
the reaction raw materials of the carbon-carbon double bond-containing low molecular weight acrylic resin 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.
3. The UV visbreaking adhesive of claim 2, wherein the soft monomer is alkyl acrylate, and the number of carbon atoms of the alkyl group is an integer of 1 to 12; the hard monomer is alkyl methacrylate, and the carbon number of the alkyl is an integer of 1-6.
4. The UV viscosity-reducing adhesive according to claim 3, wherein the soft monomer is one or more of methyl acrylate, ethyl acrylate, butyl acrylate and isooctyl acrylate; the hard monomer is one or more of methyl methacrylate, ethyl methacrylate and butyl methacrylate.
5. The UV viscosity-reducing adhesive according to claim 2, wherein 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 catalyst is one or more of dioctyltin laurate, dibutyltin dilaurate and zirconium acetylacetonate.
6. The UV viscosity-reducing adhesive according to claim 2, wherein the isocyanate containing a carbon-carbon double bond is isocyanate ethyl acrylate and/or isocyanate ethyl methacrylate; the isocyanate containing the carbon-carbon double bond and the functional monomer containing the active hydroxyl are added in the same molar amount.
7. The UV viscosity-reducing adhesive according to claim 2, wherein the preparation method of the carbon-carbon double bond-containing high molecular weight/low molecular weight acrylic resin comprises the following steps:
(1) Mixing a soft monomer, a hard monomer, a functional monomer containing active hydroxyl and a solvent in an inert atmosphere, heating to a reflux temperature under the condition of stirring, adding an initiator step by step, preserving heat for 2-8 hours, 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 solution of isocyanate containing carbon-carbon double bonds and the rest solvent under the stirring condition, and reacting for 3-5 hours to obtain the high molecular weight/low molecular weight acrylic resin containing carbon-carbon double bonds; the dripping time is 0.1-1 h;
the weight average molecular weight of the high molecular weight acrylic resin containing the carbon-carbon double bond is 50-100 ten thousand, and the weight average molecular weight of the low molecular weight acrylic resin containing the carbon-carbon double bond is 5-40 ten thousand.
8. The UV vis-breaking adhesive of 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-diphenylphosphine oxide, 4-p-phenyl mercapto benzophenone, 4-methyl benzophenone, isopropylthioxanthene, 2-ethyl anthraquinone;
the thermal curing 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 dimethanol methyl ether, dipropylene glycol methyl ether, ethyl acetate, toluene, butyl acetate and heptane.
9. The preparation method of the UV viscosity-reducing adhesive according to any one of claims 1 to 8, wherein the UV viscosity-reducing adhesive is obtained by uniformly mixing a carbon-carbon double bond-containing high molecular weight acrylic resin, a carbon-carbon double bond-containing low molecular weight acrylic resin, a photoinitiator, a thermal curing agent and an organic solvent, and standing for defoaming.
10. A UV visbreaking tape comprising the UV visbreaking adhesive of any one of claims 1-8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210987973.3A CN115232578B (en) | 2022-08-17 | 2022-08-17 | UV (ultraviolet) adhesive and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210987973.3A CN115232578B (en) | 2022-08-17 | 2022-08-17 | UV (ultraviolet) adhesive and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115232578A true CN115232578A (en) | 2022-10-25 |
| CN115232578B CN115232578B (en) | 2024-02-23 |
Family
ID=83680229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210987973.3A Active CN115232578B (en) | 2022-08-17 | 2022-08-17 | UV (ultraviolet) adhesive and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115232578B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115627135A (en) * | 2022-11-04 | 2023-01-20 | 苏州高泰电子技术股份有限公司 | Multifunctional UV viscosity-reducing composition and preparation method and application thereof |
| CN115746715A (en) * | 2022-11-30 | 2023-03-07 | 浙江工业大学 | High-temperature-resistant UV-cured peelable elastic adhesive and synthesis process thereof |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070048600A (en) * | 2005-11-04 | 2007-05-09 | 스미또모 가가꾸 가부시끼가이샤 | Acryl resin composition and adhesive |
| CN101198671A (en) * | 2005-06-23 | 2008-06-11 | 木本股份有限公司 | Adhesive and adhesive sheet |
| KR20080062642A (en) * | 2006-12-29 | 2008-07-03 | 제일모직주식회사 | Adhesive, adhesive composition and dicing film prepared therefrom |
| CN101376797A (en) * | 2007-08-31 | 2009-03-04 | 第一毛织株式会社 | Photocurable composition for the formation of pressure-sensitive adhesive layer and dicing tape produced using the same |
| JP2012067250A (en) * | 2010-09-27 | 2012-04-05 | Sekisui Chem Co Ltd | Active energy ray-curable type hot-melt adhesive composition, and adhesive sheet and adhesive label using the adhesive composition |
| CN108300336A (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, UV visbreaking films and preparation method thereof |
| 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 |
-
2022
- 2022-08-17 CN CN202210987973.3A patent/CN115232578B/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101198671A (en) * | 2005-06-23 | 2008-06-11 | 木本股份有限公司 | Adhesive and adhesive sheet |
| KR20070048600A (en) * | 2005-11-04 | 2007-05-09 | 스미또모 가가꾸 가부시끼가이샤 | Acryl resin composition and adhesive |
| KR20080062642A (en) * | 2006-12-29 | 2008-07-03 | 제일모직주식회사 | Adhesive, adhesive composition and dicing film prepared therefrom |
| CN101376797A (en) * | 2007-08-31 | 2009-03-04 | 第一毛织株式会社 | Photocurable composition for the formation of pressure-sensitive adhesive layer and dicing tape produced using the same |
| JP2012067250A (en) * | 2010-09-27 | 2012-04-05 | Sekisui Chem Co Ltd | Active energy ray-curable type hot-melt adhesive composition, and adhesive sheet and adhesive label using the adhesive composition |
| CN108300336A (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, UV visbreaking films and preparation method thereof |
| 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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115627135A (en) * | 2022-11-04 | 2023-01-20 | 苏州高泰电子技术股份有限公司 | Multifunctional UV viscosity-reducing composition and preparation method and application thereof |
| CN115746715A (en) * | 2022-11-30 | 2023-03-07 | 浙江工业大学 | High-temperature-resistant UV-cured peelable elastic adhesive and synthesis process thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115232578B (en) | 2024-02-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101927012B1 (en) | Pressure-sensitive adhesive sheet, process for producing same, and process for producing optical member using same | |
| CN115232578B (en) | UV (ultraviolet) adhesive and preparation method thereof | |
| CN110093107B (en) | Adhesive sheet, method for producing same, and method for producing image display device | |
| US20130236674A1 (en) | Adhesive composition for touch panel, adhesive film, and touch panel | |
| TWI829805B (en) | Adhesive sheet, manufacturing method thereof, and image display device manufacturing method | |
| JP2005247909A (en) | Pressure-sensitive adhesive composition and surface protective film | |
| EP2439246B1 (en) | Photocurable adhesive composition, photocurable adhesive layer, and photocurable adhesive sheet | |
| CN110093111B (en) | Adhesive sheet, method for producing same, and image display device | |
| CN112694855B (en) | Modified acrylate adhesive, adhesive tape, and preparation method and application method thereof | |
| CN114015388A (en) | Hydroxyl-containing viscose reducing agent composition and preparation method and application thereof | |
| JP6375467B2 (en) | Adhesive, adhesive film, adhesive tape, and film substrate | |
| EP2508583B1 (en) | Photocurable pressure-sensitive adhesive composition, photocurable pressure-sensitive adhesive layer, and photocurable pressure-sensitive adhesive sheet | |
| CN116948572B (en) | UV (ultraviolet) viscosity-reducing polymer composition without small molecular photoinitiator and preparation method thereof | |
| KR20170102096A (en) | Transparent bonding film and touch screen panel | |
| TWI721364B (en) | Back grinding tape | |
| CN115926690A (en) | Viscosity-reducing adhesive composition, viscosity-reducing adhesive tape and preparation method thereof | |
| CN116082985A (en) | UV (ultraviolet) adhesive-reducing tape and preparation method thereof | |
| KR20170116901A (en) | Adhesive composition and adhesive sheet for optical use | |
| JP2016224327A (en) | Polarizing plate | |
| CN116987468B (en) | Migration-free rapid UV viscosity-reducing polymer composition and preparation method thereof | |
| JP3384980B2 (en) | Baseless pressure-sensitive double-sided adhesive tape / sheet and method for producing the same | |
| KR20150045109A (en) | Method of solvent-type adhesive composition by photopolymerisation | |
| KR102596425B1 (en) | Uv curable adhesive composition for micro led display and adhesive sheet using the same | |
| KR20150045107A (en) | Solvent-type adhesive composition by photopolymerisation | |
| KR20110064979A (en) | Acrylate-adhesive resin composition, photocurable removable adhesive composition comprising the same and adhesive tape comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |