CN114015388A - Hydroxyl-containing viscose reducing agent composition and preparation method and application thereof - Google Patents
Hydroxyl-containing viscose reducing agent composition and preparation method and application thereof Download PDFInfo
- Publication number
- CN114015388A CN114015388A CN202111564311.7A CN202111564311A CN114015388A CN 114015388 A CN114015388 A CN 114015388A CN 202111564311 A CN202111564311 A CN 202111564311A CN 114015388 A CN114015388 A CN 114015388A
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- Prior art keywords
- hydroxyl
- parts
- adhesive
- acrylate
- weight
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 219
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 238000002360 preparation method Methods 0.000 title claims abstract description 72
- 229920000297 Rayon Polymers 0.000 title claims abstract description 11
- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 7
- 239000000853 adhesive Substances 0.000 claims abstract description 159
- 230000001070 adhesive effect Effects 0.000 claims abstract description 159
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 85
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 68
- 239000000178 monomer Substances 0.000 claims abstract description 47
- 239000002994 raw material Substances 0.000 claims abstract description 40
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000010410 layer Substances 0.000 claims description 28
- 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 24
- 239000002390 adhesive tape Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 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
- 230000000181 anti-adherent effect Effects 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 13
- 239000003054 catalyst Substances 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
- 230000001681 protective 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
- 239000012790 adhesive layer Substances 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 238000002156 mixing Methods 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
- 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 compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 239000002253 acid Substances 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
- 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
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 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
- 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
- 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
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 12
- 150000002513 isocyanates Chemical class 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000005286 illumination Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000001603 reducing effect Effects 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000012360 testing method Methods 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
- 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
- 239000004065 semiconductor Substances 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 2
- 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
- 230000007547 defect Effects 0.000 description 2
- WELLGRANCAVMDP-UHFFFAOYSA-N isocyanatoethane;prop-2-enoic acid Chemical compound CCN=C=O.OC(=O)C=C WELLGRANCAVMDP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002987 primer (paints) Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 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
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (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)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides a hydroxyl-containing viscose reducing agent composition, a preparation method and application thereof. The hydroxyl-containing visbreaking adhesive 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, by weight, 45-55 parts of hydroxyl-containing acrylate polymer and 4-10 parts of acrylate monomer containing isocyanate group; according to the anti-adhesion adhesive composition provided by the invention, through the synergistic effect of the specific hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent, the anti-adhesion adhesive composition can be directly crosslinked and cured under the irradiation of UV (ultraviolet) without adding UV active monomers or oligomers, so that the anti-adhesion purpose is achieved, the anti-adhesion adhesive composition is easy to fall off, has no residual adhesive, and is high in initial peel strength and good in fixity.
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, and a preparation method and application thereof.
Background
In the manufacturing process of semiconductor wafers, there is a singulation step, and various adhesive protective sheets are used when wafers are cut and polished. In the step of cutting and separating the semiconductor chips into the component pieces, these protective sheets mainly serve to fix and protect the chips, and can be peeled off 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 market at present are UV anti-adhesion protective films, the products generally have high adhesive force before UV irradiation, the adhesion is good, the adhesive force is obviously reduced after the UV irradiation with proper energy and certain wavelength, and the purpose of easy peeling is achieved. In the prior art, a UV viscosity-reducing protective film is uniformly stirred and mixed by acrylate polymer, multifunctional acrylate monomer or oligomer, photoinitiator and curing agent, and is coated on a substrate to prepare a viscosity-reducing adhesive film; however, this method requires high compatibility of each component, and there is residual gum after crosslinking. For example, CN110903779A discloses a viscosity-reducing adhesive composition and a preparation method thereof, in which polyfunctional oligomers and/or polyfunctional monomers, a solvent-based polyacrylate pressure-sensitive adhesive, a crosslinking agent, a photoinitiator, an antistatic agent and a solvent are mixed in a certain proportion and then coated on a substrate to obtain a viscosity-reducing adhesive film. However, the method is easy to cause uneven mixing of materials, the viscosity-reducing adhesive composition has wide molecular weight distribution and more small molecular weight substances, and the residual adhesive shadow is easy to form.
CN105778806A discloses a heat-resistant UV viscosity-reducing adhesive composition and a UV viscosity-reducing protective film. The UV visbreaking adhesive composition is prepared from the following raw materials in percentage by mass: 1-25% of polyfunctional oligomer or polyfunctional monomer or composition thereof, 30-50% of solvent type high-temperature-resistant polyacrylate pressure-sensitive adhesive, 0.5-1.5% of cross-linking agent A, 0.3-1.5% of photoinitiator and 35-60% of solvent. The heat-resistant UV anti-sticking protective film comprises a base material, a primer coating coated on the surface of the base material, a UV anti-sticking adhesive layer coated on the primer coating and a release film. The heat-resistant UV anti-sticking protective film prepared by the invention can resist the high temperature of 120 ℃, but the peeling force before UV illumination is low, and residual glue is easy to remain.
CN108300352A discloses an acid and alkali resistant UV visbreaking composition, a UV visbreaking film and a preparation method thereof, wherein the UV visbreaking 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 viscosity-reducing adhesive composition has poor system compatibility, easy generation of adhesive residue, low stripping force before UV irradiation and poor fixation.
Therefore, the development of an anti-adhesive tape with high peeling force before UV irradiation, rapid reduction of peeling force after irradiation, easy peeling, no adhesive residue and ring-pull resistance is a problem to be solved in the field.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a hydroxyl-containing viscose reducing agent composition, and a preparation method and application thereof. The hydroxyl-containing viscose reducing agent 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 viscosity reducing effect is achieved, the adhesive tape is easy to fall off, has no residual adhesive and is resistant to ring measurement, and the adhesive tape is high in initial peel strength and good in fixity.
In order to achieve the purpose, the invention adopts the following technical scheme:
according to the first aspect, the invention provides a hydroxyl-containing visbreaking adhesive 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, by weight, 45-55 parts of hydroxyl-containing acrylate polymer and 4-10 parts of acrylate monomer containing isocyanate group; the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 42-70 ten thousand; the glass transition temperature of the hydroxyl-containing unsaturated acrylate adhesive is-45 to-20 ℃.
According to the invention, the material containing the hydroxyl-containing viscose reducing agent composition is high in 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 additionally adding UV active monomers or oligomers, the system compatibility is good, the residual adhesive risk is avoided, and the adhesive force of the material to a base material can be improved due to the existence of hydroxyl on the hydroxyl-containing unsaturated acrylate adhesive, so that the stability is good.
Preferably, the hydroxyl-containing viscosity-reducing adhesive composition comprises 89-96 parts by weight of hydroxyl-containing unsaturated acrylate adhesive, for example, 89 parts, 90 parts, 91 parts, 92 parts, 93 parts, 94 parts, 95 parts, 96 parts and the like.
According to the invention, the specific hydroxyl-containing unsaturated acrylate adhesive is selected, so that the adhesive tape has the advantages of high initial viscosity, high peeling force, good viscosity reducing effect and no residual adhesive; when the hydroxyl-containing unsaturated acrylate adhesive does not have a hydroxyl functional group or a carbon-carbon double bond, a monomer containing a hydroxyl group or a carbon-carbon double bond is additionally added, the obtained adhesive tape has a poor viscosity reducing effect and has a residual adhesive risk.
Preferably, the hydroxyl-containing visbreaking composition includes 1 to 5 parts by weight of photoinitiator, for example, 1 part, 2 parts, 3 parts, 4 parts, 5 parts, and the like.
Preferably, the hydroxyl-containing visbreaking composition comprises 1 to 3 parts by weight of the curing agent, for example, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts and the like.
Preferably, the raw material of the hydroxyl-containing unsaturated acrylate adhesive comprises 45-55 parts by weight 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 material of the hydroxyl-containing unsaturated acrylate adhesive comprises 4-10 parts by weight of acrylate monomer containing isocyanate group, for example, 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 group in the isocyanate-containing acrylate monomer is more 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 group-containing unsaturated acrylate adhesive is 42 to 70 ten thousand, and may be, for example, 42 ten thousand, 45 ten thousand, 50 ten thousand, 55 ten thousand, 60 ten thousand, 65 ten thousand, 70 ten thousand, or the like.
In the invention, the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is less than 42 ten thousand, the reduction range of the peeling force after UV irradiation is small, and residual adhesive is easy to remain; the weight average molecular weight is more than 70 ten thousand and even higher, 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 peeling force is also low.
Preferably, the glass transition temperature of the hydroxyl group-containing unsaturated acrylate adhesive is-45 to-20 ℃, and can be, for example, -45 ℃, -40 ℃, -35 ℃, -30 ℃, -25 ℃, -20 ℃ and the like.
Preferably, the raw materials of the hydroxyl-containing acrylate polymer comprise 40-55 parts of soft monomer, 4-8 parts of hard monomer, 12-16 parts of hydroxyl-containing monomer and 0.25-0.6 part of initiator by weight.
Preferably, the raw material of the hydroxyl-containing acrylate polymer comprises 40-55 parts by weight of soft monomer, such as 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 and the like.
Preferably, the raw material of the hydroxyl-containing acrylate polymer comprises 4 to 8 parts by weight of hard monomer, for example, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts and the like.
Preferably, the raw material of 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 and the like.
Preferably, the hydroxyl-containing acrylate polymer raw material comprises 0.25-0.6 part of initiator by weight, and can be 0.25 part, 0.28 part, 0.3 part, 0.32 part, 0.34 part, 0.36 part, 0.38 part, 0.4 part, 0.5 part, 0.6 part and the like.
Preferably, the soft monomer comprises any one of isooctyl acrylate, butyl acrylate or ethyl acrylate or a combination of at least two thereof.
Preferably, the hard monomer comprises any one of vinyl acetate, acrylonitrile, acrylamide, styrene, methyl methacrylate or methyl acrylate or a combination of at least two thereof.
Preferably, the hydroxyl group-containing monomer includes any one of hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate or a combination of at least two thereof.
Preferably, the hydroxyl-containing acrylate polymer raw material further comprises 1-2 parts of acrylic acid and/or 0.1-3 parts of N, N-dimethylacrylamide.
Preferably, the raw material of the hydroxyl-containing acrylate polymer further comprises 1-2 parts by weight of acrylic acid, 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 and the like.
Preferably, the hydroxyl-containing acrylate polymer raw material further comprises 0.1-3 parts by weight of N, N-dimethylacrylamide, and can be 0.1 part, 0.5 part, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts and the like.
Preferably, the initiator comprises azobisisobutyronitrile.
As a preferred technical scheme, the raw material of the hydroxyl-containing acrylate polymer comprises isooctyl acrylate, vinyl acetate, hydroxyethyl acrylate, acrylic acid and a combination of N, N-dimethylacrylamide.
In the invention, hydroxyethyl acrylate provides a hydroxyl group for reacting with an acrylate monomer containing an isocyanate group; acrylic acid provides polar group carboxyl, which is beneficial to improving stripping force; meanwhile, the adhesive force of the viscosity-reducing adhesive composition to the base material 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 an initiator to obtain the hydroxyl-containing acrylate polymer.
Preferably, the reaction is carried out in a solvent.
Preferably, the solvent comprises any one of ethyl acetate, toluene or isopropanol or a combination of at least two thereof.
Preferably, the solvent comprises ethyl acetate.
In the invention, when the hydroxyl-containing acrylate polymer is prepared, the solvent is selected from a solvent with a low chain transfer constant (such as ethyl acetate), so that the polymer with narrow molecular weight distribution is obtained, and the occurrence of side reaction is reduced, thereby avoiding the problem that the viscose reducing composition is easy to generate residual gum after being cured.
Preferably, the method is carried out in which the initiator is added in three portions.
Preferably, the reaction includes 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 ℃ and the like.
Preferably, the time of the first stage reaction is 20-40 min, for example, 20min, 25min, 30min, 35min, 40min, etc.
Preferably, the temperature of the second stage reaction is 73 to 74 ℃, and for example, the temperature can be 73 ℃, 73.5 ℃, 74 ℃ and the like.
Preferably, the time of the second stage reaction is 1.5-2.5 h, for example, 1.5h, 2h, 2.5h, etc.
Preferably, the temperature of the third stage reaction is not less than 78 ℃, for example, 78 ℃, 79 ℃, 80 ℃, 81 ℃, 82 ℃ and the like.
In the present invention, the reaction temperature in the third stage is related to the boiling point of the solvent.
Preferably, the time of the third stage reaction is 3-4 h, for example, 3h, 3.5h, 4h, etc.
In the invention, when the hydroxyl-containing acrylate polymer is prepared, in order to improve the molecular weight of the polymer and obtain a product with narrow molecular weight distribution, the initiator is added in three times, the reaction is started at a relatively low temperature, and the reaction is carried out by gradient temperature rise in three stages (the temperature of each stage is controlled within 1 ℃).
Preferably, the hydroxyl-containing acrylate polymer has a solids content of 45 to 70%, for example, 45%, 50%, 55%, 60%, 65%, 70%, and the like.
Preferably, the acrylate monomer containing an isocyanate group includes isocyanatoethyl acrylate and/or isocyanatoethyl methacrylate.
Preferably, the raw material of the hydroxyl group-containing unsaturated acrylate adhesive further comprises 0.01 to 0.015 parts by weight of a catalyst, which may be, 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 the isocyanate group can coordinate with organic tin due to the existence of the isocyanate group, so that the isocyanate group is polarized, the carbon atom with positive charge is 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 may be, for example, 5mg KOH/g, 10mg KOH/g, 15mg KOH/g, 20mg KOH/g, 25mg KOH/g, 30mg KOH/g, 35mg KOH/g, and the like.
Preferably, the acid value of the hydroxyl-containing unsaturated acrylate adhesive is 1-5 mg KOH/g, and may be, for example, 1mg KOH/g, 2mg KOH/g, 3mg KOH/g, 4mg KOH/g, 5mg KOH/g, and the like.
In the invention, the hydroxyl value and the acid value of the hydroxyl-containing unsaturated acrylate adhesive are related to the weight part of the hydroxyl-containing unsaturated acrylate adhesive.
Preferably, the hydroxyl group-containing unsaturated acrylate adhesive is prepared by the following method, and the method 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.
Preferably, the reaction temperature is 30 to 50 ℃, for example, 30 ℃, 35 ℃, 40 ℃, 45 ℃, 50 ℃ and the like.
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 and the catalyst, and then dropwise adding the isocyanate-group-containing acrylate monomer and the solvent to perform the reaction.
Preferably, the dropping time is 20-40 min, for example, 20min, 25min, 30min, 35min, 40min, and the like.
Preferably, the solid content of the hydroxyl group-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-hydroxycyclohexylphenylketone.
Preferably, the curing agent comprises any one of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate or hexamethylene diisocyanate or a combination of at least two thereof.
In a second aspect, the present invention provides a method for preparing a hydroxyl group-containing visbreaking 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 viscosity-reducing adhesive composition.
Preferably, the mixing is carried out under exclusion of light.
In the invention, firstly, a hydroxyl-containing acrylate polymer is obtained through solution free radical polymerization; hydroxyl in the hydroxyl-containing acrylate polymer reacts 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, which comprises a substrate layer, an anti-adhesive layer and a release film layer which are sequentially stacked; the visbreaking layer comprises a hydroxyl-containing visbreaking composition as described in the first aspect.
Preferably, the thickness of the anti-adhesive layer is 8-10 μm, for example, 8 μm, 9 μm, 10 μm, and the like.
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 adopting the following method, and the method comprises the following steps: and coating the hydroxyl-containing viscosity-reducing adhesive composition on the release film layer, passing through a drying channel, attaching the release film layer to 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 2-4 min, for example, 2min, 3min, 4min, etc.
In a fourth aspect, the present invention provides a die-cut protective film comprising the hydroxyl group-containing psa composition according to the first aspect and/or the adhesive tape according to the third aspect.
The recitation of numerical ranges herein includes not only the above-recited values, but also any values between any of the above-recited numerical ranges not recited, and for brevity and clarity, is not intended to be exhaustive of the specific values encompassed within the range.
Compared with the prior art, the invention has the beneficial effects that:
according to the hydroxyl-containing visbreaking adhesive composition provided by the invention, a specific hydroxyl-containing unsaturated acrylate adhesive is selected and used in cooperation with a photoinitiator and a curing agent, so that the hydroxyl-containing visbreaking adhesive composition can be crosslinked and cured after UV illumination without adding an additional UV active monomer or oligomer, the viscosity of the adhesive tape is reduced, the peel strength before UV illumination is high, the peel force is not less than 1569g/25mm, and after UV illumination, the peel force is not more than 18g/25mm, and the adhesive tape is easy to fall off and has no residual adhesive.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The materials used in the examples and comparative examples of the present invention can be prepared by a conventional method or can be commercially available, unless otherwise specified.
Experimental example 1
A hydroxyl-containing acrylate polymer is prepared from raw materials including, 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:
according to the formula, isooctyl acrylate, vinyl acetate, hydroxyethyl acrylate, acrylic acid, N-dimethylacrylamide and 0.12 part of azobisisobutyronitrile are reacted in ethyl acetate at the reaction temperature of 66 ℃ for 30min, the temperature is increased to 73 ℃, 0.12 part of azobisisobutyronitrile is continuously added for reaction for 2h, the temperature is increased to 78 ℃, 0.11 part of azobisisobutyronitrile is added for reaction for 3.5h, and the hydroxyl-containing acrylate polymer is obtained.
Experimental example 2
A hydroxyl-containing acrylate polymer is prepared from raw materials including, 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 hydroxyl-containing acrylate polymer had a solids content of 58.8% and the specific preparation method was the same as in experimental example 1.
Experimental example 3
A hydroxyl-containing acrylate polymer is prepared from 43 parts by weight of isooctyl acrylate, 4 parts by weight of vinyl acetate, 14.4 parts by weight of hydroxyethyl acrylate, 1.2 parts by weight of acrylic acid, 3 parts by weight of N, N-dimethylacrylamide and 0.3 part by weight of azobisisobutyronitrile; the hydroxyl-containing acrylate polymer had a solids content of 57.9% and the specific preparation method was the same as in experimental example 1.
Experimental example 4
A hydroxyl-containing acrylate polymer is prepared from raw materials including, 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 azobisisobutyronitrile; the hydroxyl-containing acrylate polymer had a solids content of 64.2% and the specific preparation method was the same as in experimental example 1.
Comparative Experimental example 1
A hydroxyl-containing acrylate polymer is prepared from 43 parts by weight of isooctyl acrylate, 4 parts by weight of vinyl acetate, 15 parts by weight of hydroxyethyl acrylate, 1 part by weight of acrylic acid, 3 parts by weight of N, N-dimethylacrylamide and 0.6 part by weight of azobisisobutyronitrile; the solid content of the hydroxyl-containing acrylate polymer was 58.1%, and the specific preparation method was different from that of 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
A hydroxyl-containing acrylate polymer is prepared from raw materials including, 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 was 59.8%, and the specific preparation method was different from that of experimental example 1 only in that ethyl acetate was replaced with equal parts by weight of isopropyl alcohol, and other steps and parameters were the same as those of experimental example 1.
Comparative experiment example 3
A hydroxyl-containing acrylate polymer, wherein the raw materials of the hydroxyl-containing acrylate polymer comprise, by weight, 45 parts of isooctyl acrylate, 4 parts of vinyl acetate, 14 parts of hydroxyethyl acrylate, 1 part of acrylic acid, and 0.35 part of azobisisobutyronitrile; the solid content of the hydroxyl-containing acrylate polymer was 58.3%, and the specific preparation method was different from that of experimental example 1 only in that ethyl acetate was replaced with equal parts by weight of isopropyl alcohol, and other steps and parameters were the same as those of experimental example 1.
Comparative experiment example 4
A hydroxyl group-containing acrylate polymer which was different from experimental example 1 only in that 16 parts by weight of hydroxyethyl acrylate was used without acrylic acid, and other raw materials, amounts and preparation methods were the same as those of experimental example 1.
Comparative experiment example 5
An acrylate polymer was distinguished from Experimental example 1 only in that hydroxyethyl acrylate was replaced with acrylamide in an equal weight part, and other raw materials, amounts and preparation methods were the same as those of Experimental example 1.
Preparation example 1
The hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 50 parts of a hydroxyl-containing acrylate polymer (experimental example 1), 5 parts of ethyl isocyanate acrylate and 0.015 part of dioctyl tin laurate; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 54.5%; the preparation method comprises the following steps:
according to the formula, mixing the hydroxyl-containing acrylate polymer and dioctyl tin laurate in a reaction bottle, adjusting the reaction temperature to 40 ℃, diluting isocyanate ethyl acrylate by 10 times with n-butyl acetate, and slowly dripping the mixture into the reaction bottle for 30min to obtain the hydroxyl-containing unsaturated acrylate adhesive.
Preparation example 2
The hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 55 parts of a hydroxyl-containing acrylate polymer (experimental example 2), 5 parts of ethyl isocyanate acrylate and 0.015 part of dioctyl tin laurate; the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 56.7 percent; the specific preparation method is the same as in preparation example 1.
Preparation example 3
The hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 53 parts of hydroxyl-containing acrylate polymer (experimental example 1), 5 parts of isocyanate ethyl acrylate and 0.01 part of dioctyl tin laurate; 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 hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 53 parts of a hydroxyl-containing acrylate polymer (experimental example 3), 5 parts of isocyano ethyl methacrylate and 0.01 part of dioctyl tin laurate; 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 comprises 45 parts of a 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 hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 53 parts of hydroxyl-containing acrylate polymer (comparative experiment example 1), 5 parts of isocyano ethyl methacrylate and 0.01 part of dioctyl tin laurate; 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 hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 53 parts of hydroxyl-containing acrylate polymer (comparative experiment example 2), 5 parts of isocyanate ethyl acrylate and 0.01 part of dioctyl tin laurate; 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 hydroxyl-containing unsaturated acrylate adhesive comprises the following raw materials, by weight, 53 parts of hydroxyl-containing acrylate polymer (comparative experiment example 3), 5 parts of isocyanate ethyl acrylate and 0.01 part of dioctyl tin laurate; 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
A hydroxyl-containing unsaturated acrylate adhesive is different from 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, use amounts and preparation methods are the same as those of preparation example 1.
Comparative preparation example 5
An unsaturated acrylate adhesive is different from the preparation example 1 only in that the hydroxyl-containing acrylate polymer is replaced by the acrylate polymer provided in comparative experiment example 5 in an equal weight part, and other raw materials, the using amount and the preparation method are the same as those of the preparation example 1.
The glass transition temperature (Tg), the weight average molecular weight (Mw), the acid value and the hydroxyl value of the hydroxyl group-containing unsaturated acrylate adhesives provided in preparation examples 1 to 5 and comparative preparation examples 1 to 4 and the unsaturated acrylate adhesive provided in comparative preparation example 5 are shown in table 1.
TABLE 1
Example 1
This example provides a hydroxyl-containing anti-adhesive composition comprising, in parts by weight, 95 parts of a hydroxyl-containing unsaturated acrylate adhesive (preparation example 1), 3 parts of a photoinitiator (TPO), and 2 parts of isocyanate (HDI).
The embodiment provides a preparation method of the hydroxyl-containing visbreaking adhesive composition, which comprises the following specific steps: according to the formula, the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the isocyanate are mixed under the condition of keeping out of the sun to obtain the viscosity-reducing adhesive composition.
Example 2
This example provides a hydroxyl-containing visbreaking composition comprising, in parts by weight, 95 parts of hydroxyl-containing unsaturated acrylate adhesive (preparation example 2), 3 parts of photoinitiator (TPO), and 1.5 parts of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing visbreaking adhesive composition, which comprises the same steps as in example 1.
Example 3
This example provides a hydroxyl-containing anti-tackiness agent composition, which comprises, in parts by weight, 95 parts of a hydroxyl-containing unsaturated acrylate adhesive (preparation example 3), 3 parts of a photoinitiator (184), and 1.5 parts of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing visbreaking adhesive composition, which comprises the same steps as in example 1.
Example 4
This example provides a hydroxyl-containing anti-tackiness agent composition, which comprises 94 parts by weight of hydroxyl-containing unsaturated acrylate adhesive (preparation example 4), 2 parts by weight of photoinitiator (184) and 1.5 parts by weight of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing visbreaking adhesive composition, which comprises the same steps as in example 1.
Example 5
This example provides a hydroxyl-containing anti-tackiness agent composition, which comprises 89 parts by weight of hydroxyl-containing unsaturated acrylate adhesive (preparation example 5), 5 parts by weight of photoinitiator (184), and 3 parts by weight of isocyanate (IPDI).
This example provides a method for preparing the hydroxyl-containing visbreaking adhesive composition, which comprises the same steps as in example 1.
Comparative example 1
The present comparative example provides a hydroxyl-containing visbreaking adhesive composition comprising, in parts by weight, 94 parts of a hydroxyl-containing unsaturated acrylate adhesive (comparative preparation example 1), 2 parts of a photoinitiator (184), and 1.5 parts of isocyanate (IPDI).
The comparative example provides a preparation method of the hydroxyl-containing visbreaking adhesive composition, and the specific steps are the same as those of example 1.
Comparative example 2
The present comparative example provides a hydroxyl-containing visbreaking adhesive composition comprising, in parts by weight, 90 parts of a hydroxyl-containing unsaturated acrylate adhesive (comparative preparation example 2), 3 parts of a photoinitiator (184), and 1.5 parts of isocyanate (IPDI).
The comparative example provides a preparation method of the hydroxyl-containing visbreaking adhesive composition, and the specific steps are the same as those of example 1.
Comparative example 3
The present comparative example provides a hydroxyl group-containing anti-tackiness agent composition including, in parts by weight, 92 parts of a hydroxyl group-containing unsaturated acrylate adhesive (comparative preparation example 3), 3 parts of a photoinitiator (TPO), and 1.5 parts of isocyanate (HDI).
The comparative example provides a preparation method of the hydroxyl-containing visbreaking adhesive composition, and the specific steps are the same as those of example 1.
Comparative example 4
This example provides a hydroxyl-containing visbreaking adhesive composition, which is different 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 visbreaking adhesive composition, which comprises the same steps as in example 1.
Comparative example 5
This comparative example provides a visbreaking composition, which is different from example 1 only in that the hydroxyl group-containing unsaturated acrylate adhesive is replaced with an equal mass of acrylate polymer (comparative experiment example 5), the visbreaking composition further includes 15 parts of pentaerythritol triacrylate, and other raw materials, amounts and preparation methods are the same as those of example 1.
Comparative example 6
This comparative example provides a hydroxyl group-containing pressure-reducing adhesive composition, which is different from example 1 only in that a hydroxyl group-containing unsaturated acrylate adhesive is replaced with an equal weight part of hydroxyl group-containing acrylate polymer (experimental example 1), the hydroxyl group-containing pressure-reducing adhesive composition further includes 15 parts of pentaerythritol triacrylate, and other raw materials, amounts and preparation methods are the same as those of example 1.
Comparative example 7
This comparative example provides a visbreaking composition, which is different from example 1 only in that the hydroxyl group-containing unsaturated acrylate adhesive is replaced with an equal weight part of unsaturated acrylate adhesive (comparative preparation example 5), the visbreaking composition further includes 15 parts of pentaerythritol triacrylate, and other raw materials, amounts and preparation methods are the same as those of example 1.
Comparative example 8
This comparative example provides a hydroxyl-containing anti-adhesive composition, which is different from example 1 only in that the hydroxyl-containing unsaturated acrylate adhesive is 100 parts by weight, and other raw materials, use amounts and preparation methods are the same as those of example 1.
Comparative example 9
This comparative example provides a hydroxyl-containing visbreaking adhesive composition, which differs from example 1 only in that the curing agent is 5 parts by weight, and the other raw materials, amounts and preparation methods are the same as those of example 1.
Application example
An adhesive tape comprises a Polyolefin (PO) substrate layer, an anti-adhesive layer (with the thickness of 9 mu m) and a polyethylene terephthalate (PET) release film layer which are sequentially laminated; the anti-adhesive layer comprises the hydroxyl-containing anti-adhesive composition provided by the examples 1-5 and the comparative examples 1-4, 6 and 8-9 and the anti-adhesive composition provided by the comparative examples 5 and 7. The preparation method comprises the following steps: coating a hydroxyl-containing viscose reducing composition or a viscose reducing composition on a PET release film layer, laminating the PET release film layer with a PO (polyethylene glycol terephthalate) base material layer after passing through a drying tunnel, and drying the PO base material layer for 3min at the temperature of 90 ℃ to obtain the adhesive tape.
Performance testing
(1) Peel force before UV irradiation: conditions of UV irradiation: UV irradiation intensity 323mJ/cm2The time is 5 seconds, and a GB/T2792 method is adopted for testing;
(2) peel force after UV irradiation: conditions of UV irradiation: UV irradiation intensity 323mJ/cm2The time is 5 seconds, and a GB/T2792 method is adopted for testing;
(3) residual gum property after peeling: observing whether the surface of the chip has residual adhesive after the adhesive tape is peeled off by visual observation;
(4) the adhesive force of the anti-adhesive layer to the substrate layer is as follows: coating the viscosity-reducing adhesive composition on the surface of the base material layer to prepare an adhesive coating, cutting the adhesive coating into a plurality of strip-shaped sections until a plurality of marking lines are marked on the base material, wherein the plurality of strip-shaped sections extend along the longitudinal direction of the adhesive coating; tearing the adhesive coating film, and observing the residual degree of the coating film on the base material to judge the adhesive force of the adhesive;
wherein, if the adhesive is remained on the base material, the adhesive force is poor; no residue and good adhesion.
The specific test results are shown in table 2:
TABLE 2
As can be seen from the above table, the hydroxyl-containing anti-adhesive composition provided by the invention can be cross-linked and cured after being subjected to UV illumination in the presence of a photoinitiator and a curing agent by selecting a specific hydroxyl-containing unsaturated acrylate adhesive without additionally adding a UV active monomer or oligomer, so that the purpose of anti-adhesion is achieved, and the adhesive tape has high peel strength before being subjected to UV illumination by the hydroxyl-containing unsaturated acrylate adhesive and the curing agent in a specific ratio; after UV illumination, the coating is easy to fall off and does not have adhesive residue; as can be seen from examples 1 to 5, the peeling force of the adhesive tape before UV irradiation was 1569 to 1784g/25mm, and after irradiation, the peeling force was reduced to 15 to 18g/25 mm.
As can be seen from the comparison between example 1 and comparative examples 1 to 3, when the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is less than 42 ten thousand, that is, the hydroxyl-containing unsaturated acrylate adhesive has a wide molecular weight distribution, oligomers or monomers exist, and after UV irradiation, the peeling force is high and residual adhesives exist; as can be seen from comparison of example 1 with comparative example 4, when acrylic acid was not present in the starting material of the hydroxyl group-containing acrylic polymer, the adhesive force of the pressure-sensitive adhesive layer to the base material layer in the adhesive tape was poor, and the adhesive tape was peeled off with residual adhesive after UV irradiation; as can be seen from the comparison between example 1 and comparative examples 5 to 9, the formula of the hydroxyl-containing anti-tack adhesive composition is not the preferable combination and proportion of the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent, and the adhesive tape has the defects of adhesive residue after being stripped or low stripping force before UV irradiation and poor fixity.
In summary, the hydroxyl-containing anti-adhesive composition provided by the invention selects the specific acrylate adhesive, the photoinitiator and the curing agent for synergistic use, so that the adhesive tape comprising the hydroxyl-containing anti-adhesive composition has high peeling before UV irradiation, and rapidly reduces peeling force after irradiation, is easy to fall off, and has no adhesive residue.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention, and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The hydroxyl-containing viscosity-reducing adhesive composition is characterized by comprising 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, by weight, 45-55 parts of hydroxyl-containing acrylate polymer and 4-10 parts of acrylate monomer containing isocyanate group;
the weight average molecular weight of the hydroxyl-containing unsaturated acrylate adhesive is 42-70 ten thousand;
the glass transition temperature of the hydroxyl-containing unsaturated acrylate adhesive is-45 to-20 ℃.
2. The hydroxyl-containing visbreaking adhesive composition as claimed in claim 1, wherein the raw materials of the hydroxyl-containing acrylate polymer comprise 40-55 parts by weight of soft monomer, 4-8 parts by weight of hard monomer, 12-16 parts by weight of hydroxyl-containing monomer and 0.25-0.6 part by weight of initiator;
preferably, the soft monomer comprises any one of isooctyl acrylate, butyl acrylate or ethyl acrylate or a combination of at least two of the same;
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 group-containing monomer comprises any one of hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate or a combination of at least two thereof;
preferably, the raw material of the hydroxyl-containing acrylate polymer also comprises 1-2 parts of acrylic acid and/or 0.1-3 parts of N, N-dimethylacrylamide;
preferably, the initiator comprises azobisisobutyronitrile;
preferably, the hydroxyl-containing acrylate polymer is prepared by a solution free radical polymerization method, which comprises the following steps: carrying out free radical polymerization reaction on a soft monomer, a hard monomer, a functional monomer, a hydroxyl-containing monomer and an initiator to obtain the hydroxyl-containing acrylate polymer;
preferably, the solid content of the hydroxyl-containing acrylate polymer is 45-70%.
3. A hydroxyl-containing visbreaking composition according to claim 1 or 2, wherein the isocyanate group-containing acrylate monomer comprises isocyanate ethyl acrylate and/or isocyanatoethyl methacrylate.
4. The hydroxyl-containing visbreaking composition as claimed in any one of claims 1 to 3, wherein the hydroxyl-containing unsaturated acrylate adhesive further comprises 0.01 to 0.015 parts by weight of a catalyst;
preferably, the catalyst comprises an organotin catalyst;
preferably, the organotin catalyst comprises dioctyltin laurate and/or dibutyltin dilaurate;
preferably, the hydroxyl value of the hydroxyl-containing unsaturated acrylate adhesive is 5-35 mg KOH/g;
preferably, the acid value of the hydroxyl-containing unsaturated acrylate adhesive is 1-5 mg KOH/g;
preferably, the hydroxyl group-containing unsaturated acrylate adhesive is prepared by the following method, and the method comprises the following steps: reacting a hydroxyl-containing acrylate polymer, an isocyanate-group-containing acrylate monomer and an optional catalyst to obtain the hydroxyl-containing unsaturated acrylate adhesive;
preferably, the reaction temperature is 30-50 ℃;
preferably, the reaction is carried out in a solvent;
preferably, the solvent comprises n-butyl acetate;
preferably, the reaction comprises the steps of firstly mixing the hydroxyl-containing acrylate polymer and the catalyst, and then dropwise adding the acrylate monomer containing the isocyanate group and the solvent for reaction;
preferably, the dripping time is 20-40 min;
preferably, the solid content of the hydroxyl-containing unsaturated acrylate adhesive is 45-65%.
5. A hydroxyl-containing visbreaking composition according to any one of claims 1 to 4, wherein the photoinitiator comprises diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide and/or 1-hydroxycyclohexyl phenyl ketone;
preferably, the curing agent comprises any one of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate or hexamethylene diisocyanate or a combination of at least two thereof.
6. A preparation method of the hydroxyl-containing viscose reducing agent composition according to any one of claims 1 to 5, wherein the preparation method comprises the following steps:
and mixing the hydroxyl-containing unsaturated acrylate adhesive, the photoinitiator and the curing agent to obtain the viscosity-reducing adhesive composition.
7. The method according to claim 6, wherein the mixing is performed under a condition of shielding from light.
8. The adhesive tape is characterized by comprising a substrate layer, an anti-adhesive layer and a release film layer which are sequentially stacked;
the viscosity-reducing adhesive layer comprises the hydroxyl group-containing viscosity-reducing adhesive composition according to any one of claims 1 to 5.
9. The adhesive tape according to claim 8, wherein the thickness of the anti-adhesive layer is 8 to 10 μm;
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.
10. A die-cut protective film comprising the hydroxyl group-containing pressure-reducing adhesive composition according to any one of claims 1 to 5 and/or the adhesive tape according to claim 8 or 9.
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