CN107880209A - A kind of adhesive for quartz wafer rapid link and preparation method thereof - Google Patents

A kind of adhesive for quartz wafer rapid link and preparation method thereof Download PDF

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Publication number
CN107880209A
CN107880209A CN201711365945.3A CN201711365945A CN107880209A CN 107880209 A CN107880209 A CN 107880209A CN 201711365945 A CN201711365945 A CN 201711365945A CN 107880209 A CN107880209 A CN 107880209A
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CN
China
Prior art keywords
adhesive
component
acid
quartz wafer
oligomer
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Pending
Application number
CN201711365945.3A
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Chinese (zh)
Inventor
刘军
张晨辉
李峰
张瑞
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Shaanxi Research Design Institute of Petroleum and Chemical Industry
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Shaanxi Research Design Institute of Petroleum and Chemical Industry
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Priority to CN201711365945.3A priority Critical patent/CN107880209A/en
Publication of CN107880209A publication Critical patent/CN107880209A/en
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/34Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen

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  • 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 present invention discloses a kind of adhesive for quartz wafer rapid link and preparation method thereof, and the adhesive includes component A and B component, and component A comprises the following raw materials by weight percent:Resin monomer:90 98%, initiator:1 5%, stabilizer:0.01 1%, accelerator:0.1‑5%;B component comprises the following raw materials by weight percent:Surface conditioning agent:0.5 5%, organic solvent:95‑99.5%;Wherein, the resin monomer is the mixture of at least one of tetrabydrophthalic anhydride diethylene glycol (DEG) methacrylic acid oligomer, GMA isopropylamine oligomer or maleic anhydride 3-hydroxypivalic acid DOPCP GMA oligomer with dimethylaminoethyl methacrylate.Adhesive provided by the invention, adhesive strength, impact resistance, water resistance and oil resistivity are good, and the bonding time is short.

Description

A kind of adhesive for quartz wafer rapid link and preparation method thereof
Technical field
The invention belongs to field of adhesive technology, and in particular to a kind of adhesive for quartz wafer rapid link and its Preparation method.
Background technology
Due to the piezo-electric effect of quartz crystal, this inorganic transparent crystalline material to seem ordinary is just with electronics science skill The rapid development of art and yield unusually brilliant results.Initially it is simply applied to quartz clock, nowadays quartz-crystal resonator and quartz crystal Wave filter be applied in the circuit in need for carrying out time and FREQUENCY CONTROL.From household electrical appliance to precision instrument, from individual Mobile device is to giant brain.
The development of electronic information technology is maked rapid progress in recent years, to the requirement on machining accuracy of quartz crystal component increasingly Height, develop progressively towards miniaturization, ultrathin.Typically now by the outstanding quartzy crystal seed of artificial culture, then using multi-wire cutting After cutting mill cuts into the chip of certain specification size, bonding wafer is solidified into certain thickness square using automatic dispensing machine After completely and then it is cut to size, reuses degumming agent and remove adhesive, you can obtains the quartz wafer of small size.To quartz-crystal The bonding of piece can improve the efficiency subsequently cut, and can also improve the processing uniformity and processing efficiency of small size chip, realize compared with The package dimension of small quartz-crystal resonator.
Patent CN102585748A describe it is a kind of be used for crystal pro cessing during bonding wafer water-soluble hot-melt adhesive and Its preparation method.PUR is solid gum, in applying glue, adhesives is heated.It is required that chip is heated to necessarily After degree, applying glue is completed within a very short time.Material is waited thoroughly to solidify after cooling down after applying glue, it is not only ripe to operative employee Practice degree and require high, and continuous operation can not be realized.The PUR is using water-soluble polyester as matrix resin, although water-based Intensity can be kept in cutting fluid within a certain period of time, but at present, it is most of in quartz wafer cutting still to use oiliness cutting liquid.Should Resin can not keep certain use intensity in oiliness cutting liquid.
In research before, resin monomer is used as methacrylic acid -2- hydroxy propyl esters (HPMA) and 2,4- toluene two Polymer, 2,4 toluene diisocyanate (TDI-80) and the polyethers N210 and methacrylic acid -2- of isocyanates (TDI-80) Hydroxy propyl ester (HPMA) reacts the N210-TDI-HPMA oligomers prepared, methacrylic acid (MAA) under catalyst existence condition The epoxy vingl ester resin generated with the reaction of E-51 epoxy resin, but there are still the water resistance and oil resistant of anaerobic adhesive bonding agent The defects of property is undesirable.
Therefore it provides a kind of adhesive strength is good, the bonding time is short, and the bonding agent of good weatherability is significant.
The content of the invention
The defects of for prior art, the present invention provide a kind of adhesive and its preparation for quartz wafer rapid link Method.
A kind of adhesive for quartz wafer rapid link, including component A and B component,
Component A comprises the following raw materials by weight percent:Resin monomer:90-98%, initiator:1-5%, stabilizer:0.01- 1%, accelerator:0.1-5%;
B component comprises the following raw materials by weight percent:Surface conditioning agent:0.5-5%, organic solvent:95-99.5%;
Wherein, the resin monomer is tetrabydrophthalic anhydride-diethylene glycol (DEG)-methacrylic acid oligomer(THPA-HEE-MAA Oligomer), GMA-isopropylamine oligomer(GMA-PA oligomers)Or maleic anhydride-hydroxyl is special Valeric acid DOPCP-GMA oligomer(MAH-HPHP-GMA oligomers)At least one of and first The mixture of base dimethylaminoethyl acrylate (DMEAMA), the dimethylaminoethyl methacrylate account for the component A weight The 25-50% of amount.
Preferably, the tetrabydrophthalic anhydride-diethylene glycol (DEG)-methacrylic acid oligomer is to be prepared by the following method Obtain:By tetrabydrophthalic anhydride (THPA), diethylene glycol (DEG)(HEE), methacrylic acid (MAA) mixing, add solvent toluene With the catalyst concentrated sulfuric acid, stirring, isothermal reaction 5h after being heated to 100 DEG C, after obtained product is washed into neutrality, it is evaporated under reduced pressure Remove toluene, you can;Wherein, tetrabydrophthalic anhydride, diethylene glycol (DEG), methacrylic acid, toluene, the mass ratio of the concentrated sulfuric acid are 30:42:35:40:1.
Preferably, the GMA-isopropylamine oligomer is prepared by the following method to obtain: Under ice bath state, by isopropylamine(PA)It is added drop-wise to GMA(GMA)In, controlling reaction temperature is not higher than 30 DEG C, react 8h, you can;Wherein, the mass ratio of GMA and isopropylamine is 33:7.
Preferably, the maleic anhydride -3-hydroxypivalic acid DOPCP-GMA oligomerisation Thing is prepared by the following method to obtain:By maleic anhydride(MAH), 3-hydroxypivalic acid DOPCP(HPHP)It is mixed Close, 6h is reacted at 100 DEG C, 80 DEG C is then cooled to, adds GMA(GMA), it is anti-at 80 DEG C 6h is answered, is cooled down, you can;Wherein, maleic anhydride, 3-hydroxypivalic acid DOPCP, GMA Mass ratio is 19:21:29.
Preferably, the initiator is cumyl hydroperoxide, tert-butyl peroxide, benzoic acid t-butylperbenzoate In any one.
Preferably, the stabilizer is at least two in hydroquinones, benzoquinone, disodium ethylene diamine tetraacetate, oxalic acid Kind.
Preferably, the accelerator is DDM dodecyl mercaptan, triethylamine, propane diamine, triethanolamine, dimethylformamide, benzene Hydrazine, to toluene hydrazone, the hydrazine of 1,5- diphenyl phosphinylidyne two, N, accelerine, tetrahydroquinoline, benzoic sulfimide, adjacent benzene two At least one of acid imide, aminopyridine.
Preferably, the surface conditioning agent is ferrocene, isooctyl acid copper, naphthoic acid nickel, cobalt naphthenate, ascorbic acid, methylene Any one in base thiocarbamide, phenylthiourea.
Preferably, the organic solvent is in absolute ethyl alcohol, acetone, trichloroacetic acid, chloroform, methanol, trichloro ethylene At least one.
The preparation method of the above-mentioned adhesive for quartz wafer rapid link, comprises the following steps:
(1)Prepare component A:Resin monomer, initiator, stabilizer, accelerator are mixed, 0.5h is stirred, obtains component A;
(2)Prepare B component:Surface conditioning agent is added in organic solvent, 0.5h is stirred, obtains B component.
Provided by the present invention for the application method of the adhesive of quartz wafer rapid link:It will treat that gluing of surfaces cleaning is dry Only dry it is stand-by, with adhesive B component brushing gluing of surfaces, after 3min, then brushing adhesive A components, cementation laminated.
Advantages of the present invention:
Adhesive provided by the invention, is used cooperatively by component A and B component, adhesive strength, impact resistance, water resistance and resistance to Oiliness is good, and the bonding time is short, and quartz wafer plane adhesion positioning time can be foreshortened within 30s, can improve production operation efficiency.
Embodiment
Prepare tetrabydrophthalic anhydride-diethylene glycol (DEG)-methacrylic acid oligomer of the present invention, methacrylic acid contracting Water glyceride-isopropylamine oligomer, maleic anhydride -3-hydroxypivalic acid DOPCP-GMA Oligomer, it is specific as follows:
1. the preparation of tetrabydrophthalic anhydride-diethylene glycol (DEG)-methacrylic acid oligomer:By tetrabydrophthalic anhydride, two sweet Alcohol, methacrylic acid mixing, solvent toluene and the catalyst concentrated sulfuric acid are added, stirring, isothermal reaction 5h after being heated to 100 DEG C will After obtained product is washed to neutrality, it is evaporated under reduced pressure and removes toluene, you can;Wherein, tetrabydrophthalic anhydride, diethylene glycol (DEG), first Mass ratio between base acrylic acid, toluene, the concentrated sulfuric acid is 30:42:35:40:1.
2. the preparation method of GMA-isopropylamine oligomer:Under ice bath state, by isopropylamine It is added drop-wise in GMA, controlling reaction temperature is not higher than 30 DEG C, reacts 8h, you can;Wherein, metering system The mass ratio of acid glycidyl ester and isopropylamine is 33:7.
3. the preparation of maleic anhydride -3-hydroxypivalic acid DOPCP-GMA oligomer Method:Maleic anhydride, 3-hydroxypivalic acid DOPCP are mixed, 6h is reacted at 100 DEG C, is then cooled to 80 DEG C, GMA is added, 6h is reacted at 80 DEG C, is cooled down, you can;Wherein, maleic anhydride, hydroxyl are special Valeric acid DOPCP, the mass ratio of GMA are 19:21:29.
Embodiment 1
A kind of adhesive for quartz wafer rapid link, including component A and B component, specific such as table 1,
The component of adhesive in the embodiment 1 of table 1
The preparation method of the adhesive is as follows:
(1)Prepare component A:Resin monomer, initiator, stabilizer, accelerator are mixed, 0.5h is stirred, obtains component A;
(2)Prepare B component:Surface conditioning agent is added in organic solvent, 0.5h is stirred, obtains B component.
Embodiment 2
A kind of adhesive for quartz wafer rapid link, including component A and B component, it is specific as table 2, preparation method are same real Apply example 1.
The component of adhesive in the embodiment 2 of table 2
Embodiment 3
A kind of adhesive for quartz wafer rapid link, including component A and B component, it is specific as table 3, preparation method are same real Apply example 1.
The component of adhesive in the embodiment 3 of table 3
Embodiment 4
A kind of adhesive for quartz wafer rapid link, including component A and B component, it is specific as table 4, preparation method are same real Apply example 1.
The component of adhesive in the embodiment 4 of table 4
Embodiment 5
A kind of adhesive for quartz wafer rapid link, including component A and B component, it is specific as table 3, preparation method are same real Apply example 5.
The component of adhesive in the embodiment 5 of table 5
Comparative example 1
Quartz wafer bonding anaerobic adhesive of the prior art, composition are shown in Table 6, specific as follows:
The composition of anaerobic adhesive in the comparative example 1 of table 6
The adhesive property of the unorganic glass test piece test bonding agent of same size is respectively adopted:
It will treat that gluing of surfaces cleans up and dry stand-by, with adhesive B component brushing gluing of surfaces, after 3min, solvent volatilization, make With matched somebody with somebody adhesive component A cementation laminated, the solidified and located time is tested(Glass-glass), the drawing reached is tested after solidification 5min Stretch shear strength.And bonding test piece is immersed in machinery oil with testing tensile shear strength after 2h in distilled water respectively, with evaluation Its its medium-resistance.Test result is as follows:
After testing, the adhesive that prepared by the present invention can be realized within a short period of time under surface conditioning agent effect solidifies and reaches one Fixed intensity, the continuous operations demand of quartz wafer bonding can be met.Bonding test piece is totally submerged in machinery oil respectively, steamed Adhesive strength decay is less after 2h in distilled water.Therefore the quartz wafer after bonding agent bonding is cut in water-base cutting fluid or oil base Still have certain weatherability in liquid, remain to keep certain use intensity.It can be seen that its combination property can meet quartz completely The technique of bonding wafer and follow-up cutting processing needs.

Claims (10)

  1. A kind of 1. adhesive for quartz wafer rapid link, it is characterised in that:Including component A and B component,
    Component A comprises the following raw materials by weight percent:Resin monomer:90-98%, initiator:1-5%, stabilizer:0.01- 1%, accelerator:0.1-5%;
    B component comprises the following raw materials by weight percent:Surface conditioning agent:0.5-5%, organic solvent:95-99.5%;
    Wherein, the resin monomer is tetrabydrophthalic anhydride-diethylene glycol (DEG)-methacrylic acid oligomer, methacrylic acid contracting Water glyceride-isopropylamine oligomer or maleic anhydride -3-hydroxypivalic acid DOPCP-GMA The mixture of at least one of oligomer and dimethylaminoethyl methacrylate, the dimethylaminoethyl methacrylate Account for the 25-50% of the component A weight.
  2. A kind of 2. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:
    Tetrabydrophthalic anhydride-diethylene glycol (DEG)-methacrylic acid the oligomer is prepared by the following method to obtain:By four Hydrogen phthalic anhydride, diethylene glycol (DEG), methacrylic acid mixing, add solvent toluene and the catalyst concentrated sulfuric acid, stirring, are heated to Isothermal reaction 5h after 100 DEG C, after obtained product is washed into neutrality, it is evaporated under reduced pressure and removes toluene, you can;Wherein, tetrahydrochysene is adjacent Phthalate anhydride, diethylene glycol (DEG), methacrylic acid, toluene, the mass ratio of the concentrated sulfuric acid are 30:42:35:40:1.
  3. A kind of 3. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:The methyl Glycidyl acrylate-isopropylamine oligomer is prepared by the following method to obtain:Under ice bath state, isopropylamine is dripped It is added in GMA, controlling reaction temperature is not higher than 30 DEG C, reacts 8h, you can;Wherein, methacrylic acid The mass ratio of ethylene oxidic ester and isopropylamine is 33:7.
  4. A kind of 4. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:The suitable fourth Enedioic acid acid anhydride -3-hydroxypivalic acid DOPCP-GMA oligomer is to be prepared by the following method Arrive:Maleic anhydride, 3-hydroxypivalic acid DOPCP are mixed, 6h is reacted at 100 DEG C, is then cooled to 80 DEG C, GMA is added, 6h is reacted at 80 DEG C, is cooled down, you can;Wherein, maleic anhydride, hydroxyl are special Valeric acid DOPCP, the mass ratio of GMA are 19:21:29.
  5. A kind of 5. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:The initiation Agent is any one in cumyl hydroperoxide, tert-butyl peroxide, benzoic acid t-butylperbenzoate.
  6. A kind of 6. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:The stabilization Agent is at least two in hydroquinones, benzoquinone, disodium ethylene diamine tetraacetate, oxalic acid.
  7. A kind of 7. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:The promotion Agent be DDM dodecyl mercaptan, triethylamine, propane diamine, triethanolamine, dimethylformamide, phenylhydrazine, to toluene hydrazone, 1,5- diphenyl carbon The hydrazine of acyl two, N, at least one in accelerine, tetrahydroquinoline, benzoic sulfimide, phthalimide, aminopyridine Kind.
  8. A kind of 8. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:The surface Inorganic agent is any in ferrocene, isooctyl acid copper, naphthoic acid nickel, cobalt naphthenate, ascorbic acid, methylenethioureas, phenylthiourea It is a kind of.
  9. A kind of 9. adhesive for quartz wafer rapid link according to claim 1, it is characterised in that:It is described organic Solvent is any one in absolute ethyl alcohol, acetone, trichloroacetic acid, chloroform, methanol, trichloro ethylene.
  10. 10. it is used for the preparation method of the adhesive of quartz wafer rapid link described in claim any one of 1-9, including following step Suddenly:
    (1)Prepare component A:Resin monomer, initiator, stabilizer, accelerator are mixed, 0.5h is stirred, obtains component A;
    (2)Prepare B component:Surface conditioning agent is added in organic solvent, 0.5h is stirred, obtains B component.
CN201711365945.3A 2017-12-18 2017-12-18 A kind of adhesive for quartz wafer rapid link and preparation method thereof Pending CN107880209A (en)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868409A (en) * 1969-09-24 1975-02-25 Broadview Chem Corp Acrylic acid esters
JPS5058186A (en) * 1973-09-25 1975-05-20
JPS52121089A (en) * 1976-04-05 1977-10-12 Toagosei Chem Ind Co Ltd Anaerobic compositions with good stability
DE2714537A1 (en) * 1977-04-01 1978-10-12 Henkel Kgaa Anaerobic adhesive or sealant contg. acrylate! or methacrylate! - prepd. from glycidyl ester and linear oligo:ester of ester diol and di:carboxylic acid anhydride
JPS58168515A (en) * 1982-03-31 1983-10-04 Nitto Electric Ind Co Ltd Bonding method
US6335060B1 (en) * 1999-06-01 2002-01-01 Nippon Shokubai Co., Ltd. Curable treating agent and curing treatment process
CN1720308A (en) * 2002-12-04 2006-01-11 蒂萨股份公司 Poly(meth)acrylate-based pressure-sensitive adhesive
CN101735754A (en) * 2009-12-30 2010-06-16 黑龙江省科学院石油化学研究院 Method for plasticizing phenol formaldehyde adhesive by using polyurethane/acrylate composite resin
CN104004494A (en) * 2014-06-09 2014-08-27 成都泰美克晶体技术有限公司 Quartz wafer and crystal lump adhesive for surface mounted device (SMD) and preparation technology thereof
CN105694749A (en) * 2014-12-09 2016-06-22 日东电工株式会社 Pressure-sensitive adhesive sheet to be used in production of semiconductor

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868409A (en) * 1969-09-24 1975-02-25 Broadview Chem Corp Acrylic acid esters
JPS5058186A (en) * 1973-09-25 1975-05-20
JPS52121089A (en) * 1976-04-05 1977-10-12 Toagosei Chem Ind Co Ltd Anaerobic compositions with good stability
DE2714537A1 (en) * 1977-04-01 1978-10-12 Henkel Kgaa Anaerobic adhesive or sealant contg. acrylate! or methacrylate! - prepd. from glycidyl ester and linear oligo:ester of ester diol and di:carboxylic acid anhydride
JPS58168515A (en) * 1982-03-31 1983-10-04 Nitto Electric Ind Co Ltd Bonding method
US6335060B1 (en) * 1999-06-01 2002-01-01 Nippon Shokubai Co., Ltd. Curable treating agent and curing treatment process
CN1720308A (en) * 2002-12-04 2006-01-11 蒂萨股份公司 Poly(meth)acrylate-based pressure-sensitive adhesive
CN101735754A (en) * 2009-12-30 2010-06-16 黑龙江省科学院石油化学研究院 Method for plasticizing phenol formaldehyde adhesive by using polyurethane/acrylate composite resin
CN104004494A (en) * 2014-06-09 2014-08-27 成都泰美克晶体技术有限公司 Quartz wafer and crystal lump adhesive for surface mounted device (SMD) and preparation technology thereof
CN105694749A (en) * 2014-12-09 2016-06-22 日东电工株式会社 Pressure-sensitive adhesive sheet to be used in production of semiconductor

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* Cited by examiner, † Cited by third party
Title
李子东等编著: "《现代胶粘技术手册》", 31 January 2002, 新时代出版社 *

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Application publication date: 20180406