CN114350286A - Adhesive containing fluorine acrylate structure and application method thereof - Google Patents
Adhesive containing fluorine acrylate structure and application method thereof Download PDFInfo
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- CN114350286A CN114350286A CN202210168131.5A CN202210168131A CN114350286A CN 114350286 A CN114350286 A CN 114350286A CN 202210168131 A CN202210168131 A CN 202210168131A CN 114350286 A CN114350286 A CN 114350286A
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- acrylate
- fluorine
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- methacrylate
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 45
- 239000000853 adhesive Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 7
- QWYSJTTWCUXHQO-UHFFFAOYSA-N [F].OC(=O)C=C Chemical group [F].OC(=O)C=C QWYSJTTWCUXHQO-UHFFFAOYSA-N 0.000 title description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 48
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 38
- 239000011737 fluorine Substances 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 36
- 239000003999 initiator Substances 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
- 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 19
- 238000003756 stirring Methods 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- 229920002818 (Hydroxyethyl)methacrylate Polymers 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 12
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 12
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 12
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- DEQJNIVTRAWAMD-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)(F)CC(F)C(F)(F)OC(=O)C=C DEQJNIVTRAWAMD-UHFFFAOYSA-N 0.000 claims description 5
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 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 4
- 239000013638 trimer Substances 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 2
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 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
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 2
- 229960001826 dimethylphthalate Drugs 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-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
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 claims description 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-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
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- ZYMKZMDQUPCXRP-UHFFFAOYSA-N fluoro prop-2-enoate Chemical compound FOC(=O)C=C ZYMKZMDQUPCXRP-UHFFFAOYSA-N 0.000 claims 5
- 239000004342 Benzoyl peroxide Substances 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims 1
- -1 polytetrafluoroethylene Polymers 0.000 abstract description 19
- 229920001343 polytetrafluoroethylene Polymers 0.000 abstract description 17
- 239000004810 polytetrafluoroethylene Substances 0.000 abstract description 17
- 239000011347 resin Substances 0.000 abstract description 7
- 229920005989 resin Polymers 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000003292 glue Substances 0.000 description 34
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 15
- 239000012528 membrane Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000004321 preservation Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000005303 weighing Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 6
- 239000004642 Polyimide Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- YJKHMSPWWGBKTN-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F YJKHMSPWWGBKTN-UHFFFAOYSA-N 0.000 description 1
- 239000002998 adhesive polymer Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- HFUSECPXGUISGB-UHFFFAOYSA-N benzoyl benzenecarboperoxoate;2-tert-butylperoxy-2-methylpropane Chemical compound CC(C)(C)OOC(C)(C)C.C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 HFUSECPXGUISGB-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting 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
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a fluorine-containing acrylate structural adhesive and a use method thereof, wherein the fluorine-containing acrylate structural adhesive is prepared from the following components in parts by weight: 10-20 parts of a fluorine-containing acrylate monomer; 10-35 parts of an acrylate soft monomer; 40-50 parts of an acrylate hard monomer; 14-16 parts of a functional monomer; 0.05-0.07 part of thermal initiator; 100 portions and 120 portions of solvent. The invention introduces the fluorine-containing acrylate monomer into an acrylate adhesive system, applies the adhesive to the adhesion of fluorine-containing low surface energy materials such as polytetrafluoroethylene and the like for the first time, obtains excellent adhesion effect and has high innovation and practical value. Meanwhile, the fluorine-containing resin is crosslinked by using the curing agent to form a three-dimensional network, and compared with the non-crosslinked fluorine-containing resin, the durability and the bonding strength of the fluorine-containing resin are remarkably improved.
Description
Technical Field
The invention relates to the field of structural adhesives, in particular to a fluorine-containing acrylate structural adhesive and a use method thereof.
Background
The structural adhesive is generally an adhesive applied to a stressed part, and generally takes thermosetting resin as a raw material, is matched with components such as a curing agent and the like, and is fully cured by heating and the like to achieve an adhesive effect. The acrylate structural adhesive is widely applied by virtue of the outstanding advantages of high strength, impact resistance, aging resistance, strong adhesion and the like. However, any of these adhesives cannot achieve adhesion to a fluorine-containing material such as polytetrafluoroethylene or a low surface energy material. The reason is that the low surface energy characteristics of these materials prevent the conventional adhesives from spreading and wetting on their surfaces and thus from achieving adhesion. The fluorine-containing acrylate adhesive is expected to solve the problem, and because fluorine atoms are introduced into the structure of the fluorine-containing acrylate adhesive, the medium resistance and the durability of the polymer are improved, the surface energy of the adhesive is reduced, and the fluorine-containing acrylate adhesive can be spread on the surface with low surface energy to realize bonding. At present, no related products appear in the market, and in the aspect of published research documents, the Sun Xianzhi et al reports a fluorine-containing acrylate structural adhesive which has good water resistance and has the adhesion property to aluminum sheets reaching 28.89Mpa, however, a system mainly comprises acrylic monomers, the surface of the acrylic monomers is bound to shrink due to low surface energy, the curing effect is seriously influenced, and the system also has the problems of large smell, environmental pollution, low fault tolerance and the like.
Disclosure of Invention
The invention aims to overcome the defect that the traditional adhesive cannot bond fluorine-containing low-surface-energy materials such as polytetrafluoroethylene and the like, and provide a fluorine-containing acrylate structural adhesive which can provide bonding effect for the fluorine-containing low-surface-energy materials such as polytetrafluoroethylene and the like in order to effectively bond the fluorine-containing low-surface-energy materials with other base materials.
The invention takes acrylic ester monomers as main materials, synthesizes adhesive polymer by a way of thermally initiating free radical copolymerization, wherein, the surface energy of the adhesive is controlled by adding fluorine-containing acrylic ester monomers, the glass transition temperature of the adhesive is adjusted by adjusting the proportion of soft and hard monomers, and the functionality of the adhesive is adjusted by functional monomers.
The specific technical scheme of the invention is as follows:
the adhesive with the fluorine-containing acrylate structure is prepared from the following components in parts by weight:
10-20 parts of a fluorine-containing acrylate monomer;
10-35 parts of an acrylate soft monomer;
40-50 parts of an acrylate hard monomer;
14-16 parts of a functional monomer;
0.05-0.07 part of thermal initiator;
100 portions and 120 portions of solvent.
In some embodiments, the fluorine-containing acrylate monomer is one or more of dodecafluorooctyl methacrylate, hexafluorobutyl acrylate, trifluoroethyl acrylate and trifluoroethyl methacrylate.
In some embodiments, the acrylate soft monomer is one or more of n-butyl acrylate, isooctyl acrylate, ethyl acrylate, and n-octyl acrylate.
In some embodiments, the acrylate hard monomer is one or more of methyl methacrylate, ethyl methacrylate, isobutyl methacrylate, n-propyl methacrylate, and styrene.
In some embodiments, the functional monomer is one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, acrylic acid, methacrylic acid, glycidyl methacrylate, acrylamide, acrylonitrile, vinyl acetate, hydroxypropyl acrylate, and isobornyl (meth) acrylate.
In some embodiments, the thermal initiator is one or more of azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide tert-butyl peroxide, methyl ethyl ketone peroxide; the solvent is one or more of toluene, dimethyl phthalate, ethyl acetate, ethanol and isopropanol.
The invention also provides a use method of the adhesive containing the fluorine acrylate structure, which comprises the following steps:
adding a curing agent accounting for 2% of the weight of the fluorine-containing acrylate structural adhesive into the fluorine-containing acrylate structural adhesive, and uniformly stirring;
coating the mixed solution on the surface of a material to be adhered, adhering the material to be adhered to the surface of a target object, and curing for 24h at 70-80 ℃.
In some embodiments, the curing agent is one or more of toluene diisocyanate and its trimer, isophorone diisocyanate and its trimer, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and lysine diisocyanate.
The invention introduces the fluorine-containing acrylate monomer into an acrylate adhesive system, applies the adhesive to the adhesion of fluorine-containing low surface energy materials such as polytetrafluoroethylene and the like for the first time, obtains excellent adhesion effect and has high innovation and practical value. Meanwhile, the fluorine-containing resin is crosslinked by using the curing agent to form a three-dimensional network, and compared with the non-crosslinked fluorine-containing resin, the durability and the bonding strength of the fluorine-containing resin are remarkably improved.
Detailed Description
The description is further elucidated with reference to specific examples. The description is to be regarded as illustrative and explanatory only and should not be taken as limiting the scope of the invention in any way.
Example 1
A fluorine-containing acrylate structural adhesive and a preparation method thereof comprise the following steps:
1) weighing 40g of methyl methacrylate, 25g of n-butyl acrylate, 10g of isooctyl acrylate, 5g of vinyl acetate, 5g of acrylic acid, 5g of hydroxyethyl methacrylate, 10g of hexafluorobutyl acrylate, 0.05g of initiator AIBNB, and ethyl acetate solvent: 100 g.
Methyl methacrylate, n-butyl acrylate, isooctyl acrylate, vinyl acetate, and acrylic acid were mixed, and 60g of a solvent was added to make a monomer mixture solution.
The mixture solution is poured into a four-neck flask with mechanical stirring, a thermometer and a condenser tube and heated to 78 ℃, wherein the stirring speed is 150r/min, and the reaction system is carried out under the protection of nitrogen. And then adding a mixed solution of an initiator AIBN, hydroxyethyl methacrylate, hexafluorobutyl acrylate and 35g of ethyl acetate into the reaction system through a constant-pressure dropping funnel, wherein the dropping time is 2 hours, and after the dropping is finished, carrying out heat preservation reaction for 1 hour.
2) After the reaction, 0.012g of AIBN initiator is added, the AIBN initiator is dissolved in 5g of ethyl acetate solvent and then added into the reaction system, the reaction temperature is increased by 83 ℃, the stirring speed is increased to 220r/min, and then the heat preservation reaction is carried out for 2 hours.
3) And after the reaction, cooling and discharging.
4) Weighing part of glue solution, adding curing agent isophorone diisocyanate (IPDI) and fully stirring, wherein the using amount of the curing agent accounts for 2% of the weight of the weighed glue solution, coating the obtained glue solution on the surface of a polytetrafluoroethylene membrane by using a glass rod, controlling the thickness of the glue solution to be 50 micrometers, standing at room temperature for 1min, respectively bonding the glue solution with the polytetrafluoroethylene membrane, a polyimide membrane and a stainless steel plate, transferring the bonded glue solution into an oven at 80 ℃ after full bonding for curing for 24h, and finally taking out the glue solution for sample preparation and testing.
Example 2
A fluorine-containing acrylate structural adhesive and a preparation method thereof comprise the following steps:
1) weighing 40g of methyl methacrylate, 25g of n-butyl acrylate, 10g of isooctyl acrylate, 5g of vinyl acetate, 5g of acrylic acid, 5g of hydroxyethyl methacrylate, 10g of dodecafluoroheptyl acrylate, 0.05g of an initiator, and an ethyl acetate solvent: 100 g.
Methyl methacrylate, n-butyl acrylate, isooctyl acrylate, vinyl acetate and acrylic acid are mixed, 60g of solvent is added to form monomer mixture solution, the mixture solution is poured into a four-neck flask with mechanical stirring, a thermometer and a condenser tube and is heated to 78 ℃, wherein the stirring speed is 150r/min, and the reaction system is carried out under the protection of nitrogen. And then adding a mixed solution of an initiator AIBN, hydroxyethyl methacrylate, dodecafluoroheptyl acrylate and 35g of ethyl acetate into the reaction system through a constant-pressure dropping funnel, wherein the dropping time is 2 hours, and after the dropping is finished, carrying out heat preservation reaction for 1 hour.
2) After the reaction, 0.012g of AIBN initiator is added, the AIBN initiator is dissolved in 5g of ethyl acetate solvent and then added into the reaction system, the reaction temperature is increased by 83 ℃, the stirring speed is increased to 220r/min, and then the heat preservation reaction is carried out for 2 hours.
3) And after the reaction, cooling and discharging.
4) Weighing part of glue solution, adding curing agent isophorone diisocyanate (IPDI) and fully stirring, wherein the using amount of the curing agent accounts for 2% of the weight of the weighed glue solution, coating the obtained glue solution on the surface of a polytetrafluoroethylene membrane by using a glass rod, controlling the thickness of the glue solution to be 50 micrometers, standing at room temperature for 1min, respectively bonding the glue solution with the polytetrafluoroethylene membrane, a polyimide membrane and a stainless steel plate, transferring the bonded glue solution into an oven at 80 ℃ after full bonding for curing for 24h, and finally taking out the glue solution for sample preparation and testing.
Example 3
1) Weighing 40g of methyl methacrylate, 25g of n-butyl acrylate, 10g of isooctyl acrylate, 5g of vinyl acetate, 5g of acrylic acid, 5g of hydroxyethyl methacrylate, 15g of dodecafluoroheptyl acrylate, 0.05g of an initiator, and an ethyl acetate solvent: 100 g.
Methyl methacrylate, n-butyl acrylate, isooctyl acrylate, vinyl acetate and acrylic monomer are mixed, 60g of solvent is added to form monomer mixture solution, the mixture solution is poured into a four-neck flask with mechanical stirring, a thermometer and a condenser tube and is heated to 78 ℃, wherein the stirring speed is 150r/min, and the reaction system is carried out under the protection of nitrogen. And then adding a mixed solution of an initiator AIBN, hydroxyethyl methacrylate, dodecafluoroheptyl acrylate and 35g of ethyl acetate into the reaction system through a constant-pressure dropping funnel, wherein the dropping time is 2 hours, and after the dropping is finished, carrying out heat preservation reaction for 1 hour.
2) After the reaction, 0.012g of AIBN initiator is supplemented, the AIBN initiator is dissolved in 5g of ethyl acetate solvent and then added into the reaction system, the reaction temperature is increased by 83 ℃, the stirring speed is increased to 220r/min, and then the heat preservation reaction is carried out for 2 hours.
3) And after the reaction, cooling and discharging.
4) Weighing part of glue solution, adding a curing agent Toluene Diisocyanate (TDI) and fully stirring, wherein the using amount of the curing agent accounts for 2% of the weight of the weighed glue solution, coating the obtained glue solution on the surface of a polytetrafluoroethylene membrane by using a glass rod, controlling the thickness of the glue solution to be 50 microns, standing at room temperature for 1min, respectively bonding the glue solution with the polytetrafluoroethylene membrane, a polyimide membrane and a stainless steel plate, transferring the bonded glue solution into an oven at 80 ℃ after full bonding for curing for 24h, and finally taking out and testing a sample.
Example 4
1) Weighing 40g of methyl methacrylate, 15g of n-butyl acrylate, 10g of isooctyl acrylate, 5g of vinyl acetate, 5g of acrylic acid, 5g of hydroxyethyl methacrylate, 20g of dodecafluoroheptyl acrylate, 0.05g of an initiator, and an ethyl acetate solvent: 100 g.
Methyl methacrylate, n-butyl acrylate, isooctyl acrylate, vinyl acetate and acrylic monomer are mixed, 60g of solvent is added to form monomer mixture solution, the mixture solution is poured into a four-neck flask with mechanical stirring, a thermometer and a condenser tube and is heated to 78 ℃, wherein the stirring speed is 150r/min, and the reaction system is carried out under the protection of nitrogen. And then adding a mixed solution of an initiator AIBN, hydroxyethyl methacrylate, dodecafluoroheptyl acrylate and 35g of ethyl acetate into the reaction system through a constant-pressure dropping funnel, wherein the dropping time is 2 hours, and after the dropping is finished, carrying out heat preservation reaction for 1 hour.
2) After the reaction, 0.012g of AIBN initiator is added, the AIBN initiator is dissolved in 5g of ethyl acetate solvent and then added into the reaction system, the reaction temperature is increased by 83 ℃, the stirring speed is increased to 220r/min, and then the heat preservation reaction is carried out for 2 hours.
3) And after the reaction, cooling and discharging.
4) Weighing part of glue solution, adding curing agent isophorone diisocyanate (IPDI) and fully stirring, wherein the using amount of the curing agent accounts for 2% of the weight of the weighed glue solution, coating the obtained glue solution on the surface of a polytetrafluoroethylene membrane by using a glass rod, controlling the thickness of the glue solution to be 50 micrometers, standing at room temperature for 1min, respectively bonding the glue solution with the polytetrafluoroethylene membrane, a polyimide membrane and a stainless steel plate, transferring the bonded glue solution into an oven at 80 ℃ after full bonding for curing for 24h, and finally taking out the glue solution for sample preparation and testing.
Example 5
1) Weighing 55g of methyl methacrylate, 10g of isooctyl acrylate, 5g of vinyl acetate, 5g of acrylic acid, 5g of hydroxyethyl methacrylate, 20g of dodecafluoroheptyl acrylate, 0.05g of an initiator AIBNB, and an ethyl acetate solvent: 100 g.
Methyl methacrylate, isooctyl acrylate, vinyl acetate and acrylic monomer are mixed, 60g of solvent is added to form monomer mixture solution, the mixture solution is poured into a four-neck flask with mechanical stirring, a thermometer and a condenser tube and is heated to 78 ℃, wherein the stirring speed is 150r/min, and the reaction system is carried out under the protection of nitrogen. And then adding a mixed solution of an initiator AIBN, hydroxyethyl methacrylate, dodecafluoroheptyl acrylate and 35g of ethyl acetate into the reaction system through a constant-pressure dropping funnel, wherein the dropping time is 2 hours, and after the dropping is finished, carrying out heat preservation reaction for 1 hour.
2) After the reaction, 0.012g of AIBN initiator is supplemented, the AIBN initiator is dissolved in 5g of ethyl acetate solvent and then added into the reaction system, the reaction temperature is increased by 83 ℃, the stirring speed is increased to 220r/min, and then the heat preservation reaction is carried out for 2 hours.
3) And after the reaction, cooling and discharging.
4) Weighing part of glue solution, adding curing agent isophorone diisocyanate (IPDI) and fully stirring, wherein the using amount of the curing agent accounts for 2% of the weight of the weighed glue solution, coating the obtained glue solution on the surface of a polytetrafluoroethylene membrane by using a glass rod, controlling the thickness of the glue solution to be 50 micrometers, standing at room temperature for 1min, respectively bonding the glue solution with the polytetrafluoroethylene membrane, a polyimide membrane and a stainless steel plate, transferring the bonded glue solution into an oven at 80 ℃ after full bonding for curing for 24h, and finally taking out the glue solution for sample preparation and testing.
And (3) performance testing:
and (3) testing the shear strength: shear strength was measured at room temperature (22-25 ℃) at a pull-up rate of 10mm/min, as carried out according to the dynamic shear test standard ASTM-D1002-72.
And (3) testing the resistance to wet heat and aging: the samples were placed in a humid heat ageing oven at 85 ℃ and 85% humidity for 480 h. And then taking out the product to perform a shear strength test, and calculating the shear strength retention rate according to the shear strength value.
The performance characteristics of the examples and comparative examples are shown in the following table:
as can be seen from the results of the examples and comparative examples, the adhesive containing the fluorine-containing acrylate structure has significantly improved adhesive strength and resistance to wet heat aging for difficult-to-adhere materials such as polytetrafluoroethylene, compared with the adhesive containing no fluorine-containing acrylate structure. Further, the comparison of example 2 with example 1 shows that dodecafluoroheptyl methacrylate has a more excellent adhesion effect to a polytetrafluoroethylene material than hexafluorobutyl acrylate.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. The adhesive with the fluorine-containing acrylate structure is characterized by being prepared from the following components in parts by weight:
10-20 parts of a fluorine-containing acrylate monomer;
10-35 parts of an acrylate soft monomer;
40-50 parts of an acrylate hard monomer;
14-16 parts of a functional monomer;
0.05-0.07 part of thermal initiator;
100 portions and 120 portions of solvent.
2. The structural adhesive of claim 1, wherein the fluorine-containing acrylate monomer is one or more of dodecafluorooctyl methacrylate, hexafluorobutyl acrylate, trifluoroethyl acrylate and trifluoroethyl methacrylate.
3. The fluoroacrylate structural adhesive of claim 1, wherein said acrylate soft monomer is one or more of n-butyl acrylate, isooctyl acrylate, ethyl acrylate, and n-octyl acrylate.
4. The fluoroacrylate structural adhesive of claim 1, wherein said acrylate hard monomer is one or more of methyl methacrylate, ethyl methacrylate, isobutyl methacrylate, n-propyl methacrylate, and styrene.
5. The structural adhesive of claim 1, wherein the functional monomer is one or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, acrylic acid, methacrylic acid, glycidyl methacrylate, acrylamide, acrylonitrile, vinyl acetate, hydroxypropyl acrylate, and isobornyl (meth) acrylate.
6. The fluoroacrylate structural adhesive of claim 1, wherein said thermal initiator is one or more of azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide t-butyl peroxide, methyl ethyl ketone peroxide; the solvent is one or more of toluene, dimethyl phthalate, ethyl acetate, ethanol and isopropanol.
7. A method of using the fluoroacrylate structure adhesive of any of claims 1-6, wherein:
adding a curing agent accounting for 2% of the weight of the fluorine-containing acrylate structural adhesive into the fluorine-containing acrylate structural adhesive, and uniformly stirring;
coating the mixed solution on the surface of a material to be adhered, adhering the material to be adhered to the surface of a target object, and curing for 24h at 70-80 ℃.
8. The method for using the structural adhesive containing fluoroacrylate of claim 7 wherein the curing agent is one or more of toluene diisocyanate and its trimer, isophorone diisocyanate and its trimer, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and lysine diisocyanate.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114656902A (en) * | 2022-04-22 | 2022-06-24 | 哈尔滨工业大学无锡新材料研究院 | Heat and moisture dual-curing fluorine-containing acrylate adhesive and preparation method thereof |
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| WO2007073826A1 (en) * | 2005-12-27 | 2007-07-05 | Lohmann Gmbh & Co. Kg | Thermally hardenable adhesive |
| CN102504717A (en) * | 2011-11-07 | 2012-06-20 | 北京天山新材料技术股份有限公司 | Adhesive tape for bonding low-surface-energy material and preparation method thereof |
| CN104449483A (en) * | 2014-11-11 | 2015-03-25 | 哈尔滨工业大学无锡新材料研究院 | Fluorine-containing conductive pressure-sensitive adhesive and preparation method thereof |
| CN106543374A (en) * | 2016-10-13 | 2017-03-29 | 四川大学 | Fluoro-acrylate copolymer emulsion and preparation method thereof and prepare latex film method |
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2022
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007073826A1 (en) * | 2005-12-27 | 2007-07-05 | Lohmann Gmbh & Co. Kg | Thermally hardenable adhesive |
| CN102504717A (en) * | 2011-11-07 | 2012-06-20 | 北京天山新材料技术股份有限公司 | Adhesive tape for bonding low-surface-energy material and preparation method thereof |
| CN104449483A (en) * | 2014-11-11 | 2015-03-25 | 哈尔滨工业大学无锡新材料研究院 | Fluorine-containing conductive pressure-sensitive adhesive and preparation method thereof |
| CN106543374A (en) * | 2016-10-13 | 2017-03-29 | 四川大学 | Fluoro-acrylate copolymer emulsion and preparation method thereof and prepare latex film method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114656902A (en) * | 2022-04-22 | 2022-06-24 | 哈尔滨工业大学无锡新材料研究院 | Heat and moisture dual-curing fluorine-containing acrylate adhesive and preparation method thereof |
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