CN114015388B - Hydroxyl-containing viscose-reducing composition and preparation method and application thereof - Google Patents
Hydroxyl-containing viscose-reducing composition and preparation method and application thereof Download PDFInfo
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- CN114015388B CN114015388B CN202111564311.7A CN202111564311A CN114015388B CN 114015388 B CN114015388 B CN 114015388B CN 202111564311 A CN202111564311 A CN 202111564311A CN 114015388 B CN114015388 B CN 114015388B
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- hydroxyl
- adhesive
- parts
- acrylate
- reducing composition
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 233
- 239000000203 mixture Substances 0.000 title claims abstract description 93
- 238000002360 preparation method Methods 0.000 title claims abstract description 67
- 239000000853 adhesive Substances 0.000 claims abstract description 149
- 230000001070 adhesive effect Effects 0.000 claims abstract description 149
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 86
- 230000001603 reducing effect Effects 0.000 claims abstract description 86
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 56
- 239000000178 monomer Substances 0.000 claims abstract description 46
- 239000002994 raw material Substances 0.000 claims abstract description 40
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims abstract description 5
- 239000003292 glue Substances 0.000 claims description 58
- 239000010410 layer Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 19
- 239000002390 adhesive tape Substances 0.000 claims description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 11
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 11
- 229920006222 acrylic ester polymer Polymers 0.000 claims description 11
- 230000000181 anti-adherent effect Effects 0.000 claims description 11
- 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 10
- 230000001681 protective effect Effects 0.000 claims description 10
- 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 9
- 239000003999 initiator Substances 0.000 claims description 9
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 9
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
- 239000012790 adhesive layer Substances 0.000 claims description 8
- 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 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical group CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000005520 cutting process Methods 0.000 claims description 5
- 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 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- -1 acrylic ester Chemical class 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 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
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-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
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 230000008569 process Effects 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
- 238000005286 illumination Methods 0.000 abstract description 7
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 229920000297 Rayon Polymers 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 49
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011179 visual inspection 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
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
- H01L21/3043—Making grooves, e.g. cutting
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
- C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
- C09J2301/122—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present only on one side of the carrier, e.g. single-sided adhesive tape
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
- H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/68327—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used during dicing or grinding
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides a hydroxyl-containing viscose reducing composition, a preparation method and application thereof. The hydroxyl-containing adhesive reducing composition comprises 89-96 parts by weight of hydroxyl-containing unsaturated acrylate adhesive, 1-5 parts by weight of photoinitiator and 1-3 parts by weight of curing agent; the hydroxyl-containing unsaturated acrylate adhesive comprises an acrylate adhesive containing hydroxyl and carbon-carbon double bonds; the raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 45-55 parts of hydroxyl-containing acrylate polymer and 4-10 parts of acrylate monomer containing isocyanate groups by weight; according to the adhesive reducing composition provided by the invention, through the synergistic effect of the specific hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent, the adhesive reducing composition can be directly crosslinked and cured under UV illumination without adding a UV active monomer or oligomer, so that the purpose of reducing the adhesive is achieved, the adhesive is easy to fall off, no adhesive residue exists, the initial peel strength is high, and the fixity is good.
Description
Technical Field
The invention belongs to the technical field of chip cutting protective films, and particularly relates to a hydroxyl-containing viscose-reducing composition, a preparation method and application thereof.
Background
In the manufacturing process of semiconductor wafers, there are singulation steps, and various adhesive protection sheets are used for dicing and polishing wafers. In the step of cutting and dividing the semiconductor chip into the element chips, these protective sheets mainly serve to fix and protect the chips, and can be peeled from the wafer surface after the completion of a specific process operation.
Most of the anti-adhesion protective films applied to semiconductor wafer cutting in the current market are UV anti-adhesion protective films, and the products generally have high adhesion before UV irradiation and good adhesion, and the adhesion is obviously reduced after UV irradiation with proper energy of a certain wavelength, so that the products are easy to peel. In the prior art, the UV anti-sticking protective film is prepared by uniformly stirring and mixing an acrylic polymer, a multifunctional acrylic monomer or low polymer, a photoinitiator and a curing agent, and coating the mixture on a substrate; however, this method has high compatibility requirements for the components, and residual gum is present after crosslinking. For example, CN110903779a discloses a glue reducing composition and a method for preparing the same, wherein the glue reducing composition is prepared by mixing a polyfunctional oligomer and/or polyfunctional monomer, a solvent type polyacrylate pressure sensitive adhesive, a cross-linking agent, a photoinitiator, an antistatic agent and a solvent according to a certain proportion, and then coating the mixture on a substrate to obtain a glue reducing film. However, the method is easy to cause uneven material mixing, the viscosity reducing composition has wide molecular weight distribution and more small molecular weight substances, and residual glue shadows are easy to form.
CN105778806a discloses a heat-resistant UV-reducing adhesive composition and a UV-reducing protective film. The UV glue reducing composition comprises the following raw materials in percentage by mass: 1 to 25 percent of polyfunctional oligomer or polyfunctional monomer or a composition thereof, 30 to 50 percent of solvent type high temperature resistant polyacrylate pressure sensitive adhesive, 0.5 to 1.5 percent of cross-linking agent A, 0.3 to 1.5 percent of photoinitiator and 35 to 60 percent of solvent. The heat-resistant UV anti-sticking protective film comprises a base material, an undercoat layer coated on the surface of the base material, a UV anti-sticking layer coated on the undercoat layer and a release film. The heat-resistant UV anti-sticking protective film prepared by the invention can resist the high temperature of 120 ℃, but has low stripping force before UV illumination and is easy to leave residual glue.
CN108300352a discloses an acid and alkali resistant UV viscosity reducing composition, a UV viscosity reducing film and a preparation method thereof, wherein the UV viscosity reducing composition comprises the following components: 25-45% of polyacrylate pressure-sensitive adhesive, 1-20% of polyfunctional oligomer and/or polyfunctional monomer, 0.1-1.5% of photoinitiator, 0.1-2% of curing agent and 30-60% of solvent. However, the composition has poor system compatibility, is easy to generate residual glue, has low stripping force before UV irradiation and has poor fixity.
Therefore, developing an anti-adhesive tape with high stripping force before UV irradiation, rapid reduction of stripping force after irradiation, easy falling, no residual adhesive and ring test resistance is a problem to be solved in the field.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a hydroxyl-containing viscose-reducing composition, and a preparation method and application thereof. The hydroxyl-containing adhesive reducing composition can be directly crosslinked and cured with a photoinitiator and a curing agent under UV illumination by selecting a specific hydroxyl-containing unsaturated acrylate adhesive without adding a UV active monomer or oligomer, so that the adhesive reducing effect is achieved, the adhesive is easy to fall off, no residual adhesive exists, the ring measurement is resistant, and the adhesive tape has high initial peel strength and good fixity.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the invention provides a hydroxyl-containing glue reducing composition, which comprises 89-96 parts by weight of hydroxyl-containing unsaturated acrylate adhesive, 1-5 parts by weight of photoinitiator and 1-3 parts by weight of curing agent; the hydroxyl-containing unsaturated acrylate adhesive comprises an acrylate adhesive containing hydroxyl and carbon-carbon double bonds; the raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 45-55 parts of hydroxyl-containing acrylate polymer and 4-10 parts of acrylate monomer containing isocyanate groups by weight; the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 42 ten thousand-70 ten thousand; the glass transition temperature of the hydroxyl-containing unsaturated acrylate adhesive is-45 to-20 ℃.
According to the invention, the material comprising the hydroxyl-containing adhesive-reducing composition has high peel strength by compounding the specific hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent, the viscosity can be rapidly reduced after UV illumination without adding an additional UV active monomer or oligomer, the system compatibility is good, the risk of adhesive residue is avoided, and the adhesive force of the material to the substrate can be improved and the stability is good due to the existence of hydroxyl on the hydroxyl-containing unsaturated acrylate adhesive.
Preferably, the hydroxyl-containing glue reducing composition comprises 89 to 96 parts by weight of hydroxyl-containing unsaturated acrylate glue, for example 89 parts, 90 parts, 91 parts, 92 parts, 93 parts, 94 parts, 95 parts, 96 parts and the like.
In the invention, the specific hydroxyl-containing unsaturated acrylate adhesive is selected, so that the initial viscosity of the adhesive tape is high, the stripping force is high, the viscosity reduction effect is good, and no residual adhesive exists; when the hydroxyl-containing unsaturated acrylate adhesive has no hydroxyl functional group or no carbon-carbon double bond, but a monomer containing hydroxyl or carbon-carbon double bond is additionally added, the obtained adhesive tape has poor viscosity reducing effect and has the risk of adhesive residue.
Preferably, the hydroxyl-containing glue reducing composition comprises 1 to 5 parts by weight of photoinitiator, for example, 1 part, 2 parts, 3 parts, 4 parts, 5 parts, etc.
Preferably, the hydroxyl-containing glue reducing composition comprises 1 to 3 parts by weight of a curing agent, for example, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts, etc.
Preferably, the raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 45-55 parts of hydroxyl-containing acrylate polymer, for example, 45 parts, 46 parts, 47 parts, 48 parts, 49 parts, 50 parts, 51 parts, 52 parts, 53 parts, 54 parts, 55 parts and the like.
Preferably, the raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 4-10 parts of acrylate monomers containing isocyanate groups in parts by weight, and can be 4 parts, 5 parts, 6 parts, 7 parts, 8 parts, 9 parts, 10 parts and the like.
In the invention, the molar ratio of hydroxyl in the hydroxyl-containing acrylate polymer to isocyanate groups in the isocyanate-containing acrylate monomer is greater than 1:1, so that hydroxyl exists on the molecular chain of the hydroxyl-containing unsaturated acrylate adhesive.
Preferably, the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 42 ten thousand to 70 ten thousand, for example, 42 ten thousand, 45 ten thousand, 50 ten thousand, 55 ten thousand, 60 ten thousand, 65 ten thousand, 70 ten thousand and the like.
In the invention, the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is less than 42 ten thousand, the peeling force is reduced after UV irradiation, and residual adhesive is easy to leave; the weight average molecular weight is more than 70 ten thousand or more, the viscosity is high in the production process, and the uniform mixing is not facilitated; in addition, when the weight average molecular weight is large, the initial peel force is also low.
Preferably, the glass transition temperature of the hydroxyl-containing unsaturated acrylate adhesive is-45 to-20 ℃, and can be-45 ℃, -40 ℃, -35 ℃, -30 ℃, -25 ℃, -20 ℃ and the like.
Preferably, the raw materials of the hydroxyl-containing acrylate polymer comprise 40 to 55 parts by weight of soft monomer, 4 to 8 parts by weight of hard monomer, 12 to 16 parts by weight of hydroxyl-containing monomer and 0.25 to 0.6 part by weight of initiator.
Preferably, the raw materials of the hydroxyl-containing acrylate polymer include 40 to 55 parts by weight of soft monomers, for example, 40 parts, 41 parts, 42 parts, 43 parts, 44 parts, 45 parts, 46 parts, 47 parts, 48 parts, 49 parts, 50 parts, 51 parts, 52 parts, 53 parts, 54 parts, 55 parts, etc.
Preferably, the hydroxyl-containing acrylate polymer raw material comprises 4 to 8 parts by weight of hard monomer, for example, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts, etc.
Preferably, the hydroxyl-containing acrylate polymer comprises 12 to 16 parts by weight of hydroxyl-containing monomer, for example, 12 parts, 13 parts, 14 parts, 15 parts, 16 parts, etc.
Preferably, the hydroxyl-containing acrylate polymer comprises 0.25 to 0.6 parts by weight of initiator, for example, 0.25 parts, 0.28 parts, 0.3 parts, 0.32 parts, 0.34 parts, 0.36 parts, 0.38 parts, 0.4 parts, 0.5 parts, 0.6 parts, etc.
Preferably, the soft monomer comprises any one or a combination of at least two of isooctyl acrylate, butyl acrylate or ethyl acrylate.
Preferably, the hard monomer comprises any one or a combination of at least two of vinyl acetate, acrylonitrile, acrylamide, styrene, methyl methacrylate or methyl acrylate.
Preferably, the hydroxyl-containing monomer comprises any one or a combination of at least two of hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate.
Preferably, the raw material of the hydroxyl-containing acrylate polymer further comprises 1 to 2 parts of acrylic acid and/or 0.1 to 3 parts of N, N-dimethylacrylamide in parts by weight.
Preferably, the raw material of the hydroxyl-containing acrylate polymer further comprises 1 to 2 parts of acrylic acid in terms of weight parts, for example, 1 part, 1.2 parts, 1.3 parts, 1.4 parts, 1.5 parts, 1.6 parts, 1.7 parts, 1.8 parts, 2 parts, etc.
Preferably, the hydroxyl-containing acrylate polymer further comprises 0.1 to 3 parts by weight of N, N-dimethylacrylamide, for example, 0.1 part, 0.5 part, 1 part, 1.5 part, 2 parts, 2.5 parts, 3 parts, etc.
Preferably, the initiator comprises azobisisobutyronitrile.
As a preferred technical scheme, the raw materials of the hydroxyl-containing acrylic ester polymer comprise a combination of isooctyl acrylate, vinyl acetate, hydroxyethyl acrylate, acrylic acid and N, N-dimethylacrylamide.
In the invention, hydroxyethyl acrylate provides hydroxyl groups for reacting with acrylate monomers containing isocyanate groups; the acrylic acid provides polar group carboxyl, which is beneficial to improving the stripping force; meanwhile, the adhesive force of the adhesive reducing composition to the substrate can be improved through the synergistic effect of the hydroxyethyl acrylate and the acrylic acid.
Preferably, the hydroxyl-containing acrylate polymer is prepared by a solution free radical polymerization method, which comprises the following steps: and carrying out free radical polymerization reaction on the soft monomer, the hard monomer, the hydroxyl-containing monomer and the initiator to obtain the hydroxyl-containing acrylate polymer.
Preferably, the reaction is carried out in a solvent.
Preferably, the solvent comprises any one or a combination of at least two of ethyl acetate, toluene or isopropanol.
Preferably, the solvent comprises ethyl acetate.
In the invention, when the polymer containing hydroxyl acrylate is prepared, the solvent with low chain transfer constant (such as ethyl acetate) is selected to obtain the polymer with narrow molecular weight distribution, and side reaction is reduced, so that the problem that the adhesive residue is easy to occur after the adhesive reducing composition is cured is avoided.
Preferably, the initiator is added in three additions to the process to effect the reaction.
Preferably, the reaction comprises a first stage reaction, a second stage reaction and a third stage reaction.
Preferably, the temperature of the first stage reaction is 65 to 67 ℃, for example, 65 ℃, 66 ℃, 67 ℃, or the like.
Preferably, the time of the first stage reaction is 20 to 40min, for example, 20min, 25min, 30min, 35min, 40min, etc.
Preferably, the temperature of the second stage reaction is 73 to 74 ℃, for example, 73 ℃, 73.5 ℃, 74 ℃, and the like.
Preferably, the second stage reaction time is 1.5 to 2.5 hours, for example, 1.5 hours, 2 hours, 2.5 hours, etc.
Preferably, the temperature of the third reaction stage is not less than 78 ℃, for example, 78 ℃, 79 ℃, 80 ℃, 81 ℃, 82 ℃ and the like.
In the present invention, the third stage reaction temperature is related to the boiling point of the solvent.
Preferably, the time of the third reaction is 3 to 4 hours, for example, 3 hours, 3.5 hours, 4 hours, etc.
In the present invention, when preparing the hydroxyl-containing acrylate polymer, in order to increase the molecular weight of the polymer and obtain a product with a narrow molecular weight distribution, the initiator is added in three times, and the reaction is started from a relatively low temperature, and the reaction is performed by three-stage gradient heating (the temperature of each stage is controlled within the range of 1 ℃).
Preferably, the hydroxyl group-containing acrylate polymer has a solids content of 45 to 70%, for example, 45%, 50%, 55%, 60%, 65%, 70%, etc.
Preferably, the acrylate monomer containing isocyanate group comprises isocyanate ethyl acrylate and/or isocyano ethyl methacrylate.
Preferably, the raw materials of the hydroxyl-containing unsaturated acrylate adhesive further comprise 0.01-0.015 part of catalyst, for example, 0.01 part, 0.011 part, 0.012 part, 0.013 part, 0.014 part, 0.015 part and the like.
Preferably, the catalyst comprises an organotin catalyst.
Preferably, the organotin catalyst comprises dioctyltin laurate and/or dibutyltin dilaurate.
In the invention, the acrylate monomer containing isocyanate groups can coordinate with organic tin due to the existence of the isocyanate groups, so that the isocyanate groups are polarized, and therefore, positively charged carbon atoms are more active, and the reaction efficiency is improved.
Preferably, the hydroxyl value of the hydroxyl-containing unsaturated acrylate adhesive is 5-35 mg KOH/g, and can be, for example, 5mg KOH/g, 10mg KOH/g, 15mg KOH/g, 20mg KOH/g, 25mg KOH/g, 30mg KOH/g, 35mg KOH/g, etc.
Preferably, the hydroxyl-containing unsaturated acrylate adhesive has an acid value of 1 to 5mg KOH/g, for example, 1mg KOH/g, 2mg KOH/g, 3mg KOH/g, 4mg KOH/g, 5mg KOH/g, etc.
In the invention, the hydroxyl value and the acid value of the hydroxyl-containing unsaturated acrylate adhesive are related to the weight parts of the hydroxyl-containing unsaturated acrylate adhesive.
Preferably, the hydroxyl-containing unsaturated acrylate adhesive is prepared by a method comprising: and (3) reacting the hydroxyl-containing acrylic polymer, the acrylic monomer containing isocyanate groups and an optional catalyst to obtain the hydroxyl-containing unsaturated acrylic adhesive.
Preferably, the temperature of the reaction is 30 to 50 ℃, for example, 30 ℃, 35 ℃, 40 ℃, 45 ℃, 50 ℃ and the like can be used.
Preferably, the reaction is carried out in a solvent.
Preferably, the solvent comprises n-butyl acetate.
Preferably, the reaction comprises mixing the hydroxyl-containing acrylate polymer with the catalyst, and then dropwise adding the acrylate monomer containing isocyanate groups and the solvent for reaction.
Preferably, the time of the dropping is 20 to 40min, for example, 20min, 25min, 30min, 35min, 40min, etc.
Preferably, the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 45-65%, for example, 45%, 50%, 55%, 60%, 65% and the like.
Preferably, the photoinitiator comprises diphenyl (2, 4, 6-trimethylbenzoyl) phosphine oxide and/or 1-hydroxycyclohexyl phenyl ketone.
Preferably, the curing agent comprises any one or a combination of at least two of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate or hexamethylene diisocyanate.
In a second aspect, the present invention provides a method for preparing the hydroxyl-containing glue reducing composition according to the first aspect, the method comprising the steps of:
and mixing the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent to obtain the hydroxyl-containing glue reducing composition.
Preferably, the mixing is carried out under light-protected conditions.
In the invention, firstly, a hydroxyl-containing acrylic ester polymer is obtained through solution free radical polymerization; the hydroxyl groups in the hydroxyl-containing acrylate polymer react with isocyanate groups in the isocyanate-containing acrylate monomer, so that unsaturated double bonds are reserved for UV irradiation crosslinking.
In a third aspect, the invention provides an adhesive tape comprising a substrate layer, an anti-adhesive layer and a release film layer which are laminated in sequence; the adhesive reducing layer comprises the hydroxyl-containing adhesive reducing composition according to the first aspect.
Preferably, the thickness of the anti-adhesive layer is 8 to 10 μm, for example, 8 μm, 9 μm, 10 μm, etc.
Preferably, the substrate layer comprises a polyolefin substrate layer and/or a polyvinyl chloride substrate layer.
Preferably, the release film layer comprises a polyester release film layer.
The adhesive tape provided by the invention is prepared by the following method, which comprises the following steps: coating a hydroxyl-containing adhesive reducing composition on the release film layer, passing through a drying tunnel, attaching with the substrate layer, and drying to obtain the adhesive tape.
Preferably, the drying temperature is 80 to 100 ℃, for example, 80 ℃, 85 ℃, 90 ℃, 95 ℃, 100 ℃ and the like.
Preferably, the drying time is 2 to 4min, for example, 2min, 3min, 4min, etc.
In a fourth aspect, the present invention provides a die-cut protective film comprising the hydroxyl-containing glue reducing composition according to the first aspect and/or the tape according to the third aspect.
The numerical ranges recited herein include not only the recited point values, but also any point values between the recited numerical ranges that are not recited, and are limited to, and for the sake of brevity, the invention is not intended to be exhaustive of the specific point values that the recited range includes.
Compared with the prior art, the invention has the beneficial effects that:
the hydroxyl-containing adhesive reducing composition provided by the invention can be crosslinked and cured after UV irradiation to reduce the adhesive of the adhesive tape by selecting the specific hydroxyl-containing unsaturated acrylate adhesive and using the specific hydroxyl-containing unsaturated acrylate adhesive in cooperation with the photoinitiator and the curing agent, wherein the peel strength is higher than or equal to 1569g/25mm before UV irradiation, the peel strength is lower than or equal to 18g/25mm after UV irradiation, the adhesive is easy to fall off, and no residual adhesive is generated.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The materials used in the examples and comparative examples of the present invention can be prepared by a conventional method or commercially available, unless otherwise specified.
Experimental example 1
The raw materials of the hydroxyl-containing acrylic ester polymer comprise, by weight, 45 parts of isooctyl acrylate, 4 parts of vinyl acetate, 15 parts of hydroxyethyl acrylate, 1 part of acrylic acid, 3 parts of N, N-dimethylacrylamide and 0.35 part of azobisisobutyronitrile; the solid content of the hydroxyl-containing acrylate polymer is 59.8%, and the specific preparation method comprises the following steps:
and (3) reacting isooctyl acrylate, vinyl acetate, hydroxyethyl acrylate, acrylic acid, N-dimethylacrylamide and 0.12 part of azobisisobutyronitrile in ethyl acetate according to the formula amount for 30min at the reaction temperature of 66 ℃, heating to 73 ℃, continuously adding 0.12 part of azobisisobutyronitrile for 2h, heating to 78 ℃, and adding 0.11 part of azobisisobutyronitrile for 3.5h to obtain the hydroxyl-containing acrylate polymer.
Experimental example 2
The raw materials of the hydroxyl-containing acrylic ester polymer comprise, by weight, 45 parts of isooctyl acrylate, 4 parts of vinyl acetate, 12 parts of hydroxyethyl acrylate, 1.3 parts of acrylic acid, 3 parts of N, N-dimethylacrylamide and 0.35 part of azobisisobutyronitrile; the solid content of the hydroxyl-containing acrylate polymer was 58.8%, and the specific preparation method was the same as that of experimental example 1.
Experimental example 3
The raw materials of the hydroxyl-containing acrylic ester polymer comprise 43 parts of isooctyl acrylate, 4 parts of vinyl acetate, 14.4 parts of hydroxyethyl acrylate, 1.2 parts of acrylic acid, 3 parts of N, N-dimethyl acrylamide and 0.3 part of azodiisobutyronitrile in parts by weight; the solid content of the hydroxyl-containing acrylate polymer was 57.9%, and the specific preparation method was the same as that of experimental example 1.
Experimental example 4
The raw materials of the hydroxyl-containing acrylic ester polymer comprise, by weight, 30 parts of isooctyl acrylate, 25 parts of butyl acrylate, 4 parts of vinyl acetate, 4 parts of methyl methacrylate, 15 parts of hydroxyethyl acrylate, 1 part of acrylic acid, 3 parts of N, N-dimethylformamide and 0.35 part of azodiisobutyronitrile; the solid content of the hydroxyl-containing acrylate polymer was 64.2%, and the specific preparation method was the same as that of experimental example 1.
Comparative experiment example 1
The raw materials of the hydroxyl-containing acrylic ester polymer comprise 43 parts of isooctyl acrylate, 4 parts of vinyl acetate, 15 parts of hydroxyethyl acrylate, 1 part of acrylic acid, 3 parts of N, N-dimethylacrylamide and 0.6 part of azodiisobutyronitrile in parts by weight; the hydroxyl-containing acrylate polymer had a solids content of 58.1% and the specific preparation method was different from experimental example 1 only in that ethyl acetate was replaced with toluene, and other steps and parameters were the same as those of experimental example 1.
Comparative experiment example 2
The raw materials of the hydroxyl-containing acrylic ester polymer comprise, by weight, 45 parts of isooctyl acrylate, 4 parts of vinyl acetate, 15 parts of hydroxyethyl acrylate, 1 part of acrylic acid, 3 parts of N, N-dimethylacrylamide and 0.35 part of azobisisobutyronitrile; the hydroxyl-containing acrylate polymer had a solids content of 59.8% and the specific preparation method was different from experimental example 1 only in that ethyl acetate was replaced with isopropyl alcohol in equal parts by weight, and the other steps and parameters were the same as those of experimental example 1.
Comparative experiment example 3
A hydroxyl-containing acrylate polymer, the raw materials of which comprise 45 parts by weight of isooctyl acrylate, 4 parts by weight of vinyl acetate, 14 parts by weight of hydroxyethyl acrylate, 1 part by weight of acrylic acid and 0.35 part by weight of azobisisobutyronitrile; the hydroxyl-containing acrylate polymer had a solids content of 58.3% and the specific preparation method was different from experimental example 1 only in that ethyl acetate was replaced with isopropyl alcohol in equal parts by weight, and the other steps and parameters were the same as those of experimental example 1.
Comparative experiment example 4
The hydroxyl-containing acrylate polymer was different from experimental example 1 only in that the hydroxyethyl acrylate was 16 parts by weight, and no acrylic acid was present, and other raw materials, amounts and preparation methods were the same as those of experimental example 1.
Comparative experiment example 5
An acrylic polymer was different from experimental example 1 only in that hydroxyethyl acrylate was replaced with an equal weight part of acrylamide, and other raw materials, amounts and preparation methods were the same as those of experimental example 1.
Preparation example 1
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 50 parts of hydroxyl-containing acrylate polymer (experimental example 1), 5 parts of isocyanate ethyl acrylate and 0.015 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 54.5%; the preparation method comprises the following steps:
mixing a hydroxyl-containing acrylic ester polymer and dioctyltin laurate in a reaction bottle according to the formula amount, adjusting the reaction temperature to 40 ℃, diluting isocyanate ethyl acrylate with n-butyl acetate for 10 times, slowly dripping the mixture into the reaction bottle for 30min, and obtaining the hydroxyl-containing unsaturated acrylic ester adhesive.
Preparation example 2
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 55 parts of hydroxyl-containing acrylate polymer (experimental example 2), 5 parts of isocyanate ethyl acrylate and 0.015 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 56.7%; the specific preparation method is the same as in preparation example 1.
Preparation example 3
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 53 parts of hydroxyl-containing acrylate polymer (experimental example 1), 5 parts of isocyanate ethyl acrylate and 0.01 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 55.8%; the specific preparation method is the same as in preparation example 1.
Preparation example 4
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 53 parts of hydroxyl-containing acrylate polymer (experimental example 3), 5 parts of isocyanoethyl methacrylate and 0.01 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 55.8%; the specific preparation method is the same as in preparation example 1.
Preparation example 5
A hydroxyl-containing unsaturated acrylate adhesive comprising 45 parts of hydroxyl-containing acrylate polymer (experimental example 4), 10 parts of isocyanate ethyl acrylate and 0.012 part of dibutyltin dilaurate; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 54.5%; the specific preparation method is the same as in preparation example 1.
Comparative preparation example 1
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 53 parts of hydroxyl-containing acrylate polymer (comparative experiment example 1), 5 parts of isocyanoethyl methacrylate and 0.01 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 55.8%; the specific preparation method is the same as in preparation example 1.
Comparative preparation example 2
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 53 parts of hydroxyl-containing acrylate polymer (comparative experiment 2), 5 parts of isocyanate ethyl acrylate and 0.01 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 55.8%, and the specific preparation method is the same as that of preparation example 1.
Comparative preparation example 3
The raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 53 parts of hydroxyl-containing acrylate polymer (comparative experiment 3), 5 parts of isocyanate ethyl acrylate and 0.01 part of dioctyltin laurate in parts by weight; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 55.8%, and the specific preparation method is the same as that of preparation example 1.
Comparative preparation example 4
The hydroxyl-containing unsaturated acrylate adhesive is different from the preparation example 1 only in that the hydroxyl-containing acrylate polymer is the hydroxyl-containing acrylate polymer provided in comparative experiment example 4, and other raw materials, the amount and the preparation method are the same as those of the preparation example 1.
Comparative preparation example 5
An unsaturated acrylate adhesive differs from preparation example 1 only in that the hydroxyl-containing acrylate polymer is replaced with an equal weight part of the acrylate polymer provided in comparative experiment 5, and other raw materials, amounts and preparation methods are the same as those of preparation example 1.
Glass transition temperatures (Tg), weight average molecular weights (Mw), acid values, and hydroxyl values of the hydroxyl group-containing unsaturated acrylate adhesives provided in preparation examples 1 to 5, comparative preparation examples 1 to 4, and the unsaturated acrylate adhesives provided in comparative preparation example 5 are shown in Table 1.
TABLE 1
Example 1
This example provides a hydroxyl-containing glue reducing composition comprising, in parts by weight, 95 parts of a hydroxyl-containing unsaturated acrylate adhesive (preparation 1), 3 parts of a photoinitiator (TPO) and 2 parts of isocyanate (HDI).
The embodiment provides a preparation method of the hydroxyl-containing viscose-reducing composition, which comprises the following specific steps: and mixing the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the isocyanate under the light-shielding condition according to the formula amount to obtain the glue reducing composition.
Example 2
This example provides a hydroxyl-containing glue reducing composition comprising, in parts by weight, 95 parts of a hydroxyl-containing unsaturated acrylate adhesive (preparation 2), 3 parts of a photoinitiator (TPO) and 1.5 parts of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific steps are the same as in example 1.
Example 3
This example provides a hydroxyl-containing glue reducing composition comprising, in parts by weight, 95 parts of a hydroxyl-containing unsaturated acrylate adhesive (preparation 3), 3 parts of a photoinitiator (184) and 1.5 parts of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific steps are the same as in example 1.
Example 4
This example provides a hydroxyl-containing glue reducing composition comprising 94 parts by weight of a hydroxyl-containing unsaturated acrylate adhesive (preparation 4), 2 parts of a photoinitiator (184) and 1.5 parts of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific steps are the same as in example 1.
Example 5
This example provides a hydroxyl-containing glue reducing composition comprising 89 parts by weight of a hydroxyl-containing unsaturated acrylate adhesive (preparation 5), 5 parts of a photoinitiator (184) and 3 parts of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific steps are the same as in example 1.
Comparative example 1
This comparative example provides a hydroxyl-containing glue reducing composition comprising 94 parts by weight of a hydroxyl-containing unsaturated acrylate adhesive (comparative preparation 1), 2 parts of a photoinitiator (184) and 1.5 parts of isocyanate (IPDI).
This comparative example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific procedure is the same as in example 1.
Comparative example 2
This comparative example provides a hydroxyl-containing glue reducing composition comprising, in parts by weight, 90 parts of a hydroxyl-containing unsaturated acrylate adhesive (comparative preparation 2), 3 parts of a photoinitiator (184) and 1.5 parts of isocyanate (IPDI).
This comparative example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific procedure is the same as in example 1.
Comparative example 3
This comparative example provides a hydroxyl-containing glue reducing composition comprising, in parts by weight, 92 parts of a hydroxyl-containing unsaturated acrylate adhesive (comparative preparation 3), 3 parts of a photoinitiator (TPO) and 1.5 parts of isocyanate (HDI).
This comparative example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific procedure is the same as in example 1.
Comparative example 4
This example provides a hydroxyl-containing glue reducing composition which differs from example 1 only in that the hydroxyl-containing unsaturated acrylate adhesive is the hydroxyl-containing unsaturated acrylate adhesive provided in comparative preparation example 4, and other raw materials and amounts are the same as those in example 1.
This example provides a method for preparing the hydroxyl-containing glue reducing composition, and the specific steps are the same as in example 1.
Comparative example 5
This comparative example provides a glue reducing composition which differs from example 1 only in that the hydroxyl-containing unsaturated acrylate adhesive is replaced by an equal mass of acrylate polymer (comparative experiment 5), the glue reducing composition further comprises 15 parts of pentaerythritol triacrylate, and other raw materials, amounts and preparation methods are the same as in example 1.
Comparative example 6
This comparative example provides a hydroxyl-containing glue reducing composition which differs from example 1 only in that the hydroxyl-containing unsaturated acrylate adhesive is replaced with equal parts by weight of a hydroxyl-containing acrylate polymer (experimental example 1), and the hydroxyl-containing glue reducing composition further comprises 15 parts of pentaerythritol triacrylate, and other raw materials, amounts and preparation methods are the same as in example 1.
Comparative example 7
This comparative example provides a glue reducing composition which differs from example 1 only in that the hydroxyl-containing unsaturated acrylate adhesive is replaced by an equal weight of unsaturated acrylate adhesive (comparative preparation 5), and the glue reducing composition further comprises 15 parts of pentaerythritol triacrylate, and other raw materials, amounts and preparation methods are the same as in example 1.
Comparative example 8
This comparative example provides a hydroxyl-containing glue reducing composition which differs from example 1 only in that the hydroxyl-containing unsaturated acrylate adhesive is 100 parts by weight, and other raw materials, amounts and preparation methods are the same as example 1.
Comparative example 9
This comparative example provides a hydroxyl-containing glue reducing composition which differs from example 1 only in that the curing agent is 5 parts by weight, and other raw materials, amounts and preparation methods are the same as in example 1.
Application example
An adhesive tape comprising a Polyolefin (PO) substrate layer, an anti-adhesive layer (9 μm in thickness) and a polyethylene terephthalate (PET) release film layer laminated in this order; the anti-adhesive layer comprises the hydroxyl-containing anti-adhesive compositions provided in examples 1 to 5, comparative examples 1 to 4,6 and 8 to 9 and the anti-adhesive compositions provided in comparative examples 5 and 7. The preparation method comprises the following steps: coating a hydroxyl-containing adhesive reducing composition or an adhesive reducing composition on the PET release film layer, bonding the PET release film layer with the PO substrate layer after passing through a drying tunnel, and drying the PET release film layer for 3min at 90 ℃ to obtain the adhesive tape.
Performance testing
(1) Peel force before UV irradiation: conditions of UV irradiation: UV irradiation intensity 323mJ/cm 2 The time is 5 seconds, and the GB/T2792 method is adopted for testing;
(2) Peel force after UV irradiation: conditions of UV irradiation: UV irradiation intensity 323mJ/cm 2 The time is 5 seconds, and the GB/T2792 method is adopted for testing;
(3) Residual tackiness after peeling: after the adhesive tape is stripped by visual inspection, whether residual adhesive exists on the surface of the chip or not;
(4) Adhesion of the anti-adhesive layer to the substrate layer: coating the adhesive reducing composition on the surface of the substrate layer to prepare an adhesive coating film, and cutting the adhesive coating film into a plurality of strip-shaped sections until a plurality of marking lines are drawn on the substrate, wherein the strip-shaped sections extend along the longitudinal direction of the adhesive coating film; tearing the adhesive coating film, and observing the residual degree of the coating film on the substrate to judge the adhesive force of the adhesive;
wherein, the adhesive has residues on the base material, and the adhesive force is poor; has no residue and good adhesive force.
The specific test results are shown in table 2:
TABLE 2
As can be seen from the table, the hydroxyl-containing adhesive reducing composition provided by the invention can be crosslinked and cured after UV irradiation in the presence of a photoinitiator and a curing agent by selecting a specific hydroxyl-containing unsaturated acrylate adhesive without adding an additional UV active monomer or oligomer, so that the purpose of reducing the adhesive is achieved, and the adhesive tape has high stripping force before UV irradiation in a specific proportion by the hydroxyl-containing unsaturated acrylate adhesive and the curing agent; after UV illumination, the adhesive is easy to fall off and no adhesive residue exists; as is clear from examples 1 to 5, the peeling force of the adhesive tape before irradiation with UV light was 1569 to 1784g/25mm, and after irradiation, the peeling force was reduced to 15 to 18g/25mm.
As can be seen from the comparison of the examples 1 and the comparative examples 1 to 3, the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is less than 42 ten thousand, i.e. the hydroxyl-containing unsaturated acrylate adhesive has a wide molecular weight distribution, has oligomers or monomers, has higher stripping force after UV irradiation, and has residual glue; as is clear from comparison of example 1 with comparative example 4, when acrylic acid is not contained in the raw material of the hydroxyl group-containing acrylic polymer, the adhesion of the anti-adhesive layer to the base material layer in the adhesive tape is poor, and the adhesive tape is peeled off with a residual adhesive after UV irradiation; as is clear from a comparison of example 1 and comparative examples 5 to 9, the formulation of the hydroxyl-containing adhesive reducing composition is not the combination and the proportion of the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent which are preferable in the present invention, and the adhesive tape has residual adhesive after release or has low peeling force before UV irradiation and poor fixity.
In summary, the hydroxyl-containing adhesive reducing composition provided by the invention has the advantages that the specific acrylate adhesive, the photoinitiator and the curing agent are selected for cooperative use, so that the adhesive tape comprising the hydroxyl-containing adhesive reducing composition has high stripping force before UV illumination, rapidly reduces stripping force after illumination, is easy to fall off and has no residual adhesive.
While the foregoing is directed to embodiments of the present invention, other and further details of the invention may be had by the present invention, it should be understood that the foregoing description is merely illustrative of the present invention and that no limitations are intended to the scope of the invention, except insofar as modifications, equivalents, improvements or modifications are within the spirit and principles of the invention.
Claims (25)
1. The hydroxyl-containing adhesive reducing composition is characterized by comprising, by weight, 95 parts of hydroxyl-containing unsaturated acrylate adhesive, 3-5 parts of photoinitiator and 2-3 parts of curing agent;
the hydroxyl-containing unsaturated acrylate adhesive comprises an acrylate adhesive containing hydroxyl and carbon-carbon double bonds;
the raw materials of the hydroxyl-containing unsaturated acrylate adhesive comprise 48-52 parts of hydroxyl-containing acrylate polymer and 4-6 parts of acrylate monomer containing isocyanate groups by weight;
the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 55-60 ten thousand;
the glass transition temperature of the hydroxyl-containing unsaturated acrylate adhesive is-41 to-38 ℃;
the raw materials of the hydroxyl-containing acrylate polymer comprise, by weight, 44-54 parts of soft monomers, 4-8 parts of hard monomers, 15-16 parts of hydroxyl-containing monomers and 0.25-0.6 part of initiator;
the raw materials of the hydroxyl-containing acrylic ester polymer further comprise 1-2 parts of acrylic acid and 0.1-3 parts of N, N-dimethylacrylamide by weight;
the acrylic ester monomer containing isocyanate groups is isocyanate ethyl acrylate;
the hydroxyl-containing acrylic ester polymer is prepared by adopting a solution free radical polymerization method; the solution is ethyl acetate;
the hydroxyl-containing unsaturated acrylate adhesive is prepared by the following method, which comprises the following steps: reacting a hydroxyl-containing acrylate polymer, an isocyanate-containing acrylate monomer and an optional catalyst to obtain the hydroxyl-containing unsaturated acrylate adhesive; the reaction is carried out in a solvent; the solvent is n-butyl acetate.
2. The hydroxyl-containing glue reducing composition according to claim 1, wherein the soft monomer comprises any one or a combination of at least two of isooctyl acrylate, butyl acrylate, or ethyl acrylate.
3. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hard monomer comprises any one or a combination of at least two of vinyl acetate, acrylonitrile, acrylamide, styrene, methyl methacrylate or methyl acrylate.
4. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl-containing monomer comprises any one or a combination of at least two of hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate.
5. The hydroxyl-containing glue reducing composition according to claim 1, wherein the initiator comprises azobisisobutyronitrile.
6. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl-containing acrylate polymer is prepared by a process comprising: and carrying out free radical polymerization reaction on the soft monomer, the hard monomer, the functional monomer, the hydroxyl-containing monomer and the initiator to obtain the hydroxyl-containing acrylate polymer.
7. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl-containing acrylate polymer has a solids content of 45-70%.
8. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl-containing unsaturated acrylate adhesive further comprises 0.01-0.015 parts of a catalyst in parts by weight.
9. The hydroxyl-containing glue reducing composition according to claim 8, wherein the catalyst comprises an organotin catalyst.
10. The hydroxyl-containing glue reducing composition according to claim 9, wherein the organotin catalyst comprises dioctyltin laurate and/or dibutyltin dilaurate.
11. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl value of the hydroxyl-containing unsaturated acrylate adhesive is 5-35 mg KOH/g.
12. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl-containing unsaturated acrylate adhesive has an acid value of 1-5 mg KOH/g.
13. The hydroxyl-containing adhesive reducing composition according to claim 1, wherein the reaction temperature is 30-50 ℃ in the preparation method of the hydroxyl-containing unsaturated acrylate adhesive.
14. The hydroxyl-containing adhesive reducing composition according to claim 1, wherein the hydroxyl-containing unsaturated acrylate adhesive is prepared by mixing a hydroxyl-containing acrylate polymer with a catalyst, and then adding an isocyanate-containing acrylate monomer and a solvent dropwise for reaction.
15. The hydroxyl-containing glue reducing composition according to claim 14, wherein the time of dripping is 20-40 min.
16. The hydroxyl-containing glue reducing composition according to claim 1, wherein the hydroxyl-containing unsaturated acrylate adhesive has a solids content of 45-65%.
17. The hydroxyl-containing glue reducing composition according to claim 1, wherein the photoinitiator comprises diphenyl (2, 4, 6-trimethylbenzoyl) phosphine oxide and/or 1-hydroxycyclohexyl phenyl ketone.
18. The hydroxyl-containing glue reducing composition according to claim 1, wherein the curing agent comprises any one or a combination of at least two of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, or hexamethylene diisocyanate.
19. A method of preparing a hydroxyl-containing glue reducing composition according to any one of claims 1 to 18, comprising the steps of:
and mixing the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent to obtain the adhesive reducing composition.
20. The method of claim 19, wherein the mixing is performed under light-protected conditions.
21. The adhesive tape is characterized by comprising a substrate layer, an anti-adhesive layer and a release film layer which are sequentially laminated;
the adhesive reducing layer comprising the hydroxyl-containing adhesive reducing composition according to any one of claims 1 to 18.
22. The tape of claim 21, wherein the thickness of the anti-adhesive layer is 8-10 μm.
23. The tape of claim 21, wherein the substrate layer comprises a polyolefin substrate layer and/or a polyvinyl chloride substrate layer.
24. The tape of claim 21, wherein the release film layer comprises a polyester release film layer.
25. A die cutting protective film comprising the hydroxyl-containing adhesive reducing composition according to any one of claims 1 to 18 or the tape according to any one of claims 21 to 24.
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| CN114685709A (en) * | 2022-03-25 | 2022-07-01 | 东莞澳中新材料科技股份有限公司 | Acrylic resin for high-temperature-resistant UV (ultraviolet) adhesive reducing agent and preparation method and application thereof |
| CN115232578B (en) * | 2022-08-17 | 2024-02-23 | 苏州赛伍应用技术股份有限公司 | UV (ultraviolet) adhesive and preparation method thereof |
| 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 |
| CN117624498A (en) * | 2023-12-15 | 2024-03-01 | 江苏科麦特科技发展有限公司 | Polyacrylate and UV-curable adhesive-reducing composition containing photocurable alkenyl groups in side chains |
| CN118005837A (en) * | 2024-04-09 | 2024-05-10 | 广州慧谷功能材料有限公司 | Low-temperature-response acrylic ester copolymer, adhesive, optical film and preparation method and application thereof |
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