CN107446540A - A kind of UV photocurable polyurethane acrylates adhesives and preparation method thereof - Google Patents

A kind of UV photocurable polyurethane acrylates adhesives and preparation method thereof Download PDF

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Publication number
CN107446540A
CN107446540A CN201710770693.6A CN201710770693A CN107446540A CN 107446540 A CN107446540 A CN 107446540A CN 201710770693 A CN201710770693 A CN 201710770693A CN 107446540 A CN107446540 A CN 107446540A
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polyurethane acrylates
adhesives
photocurable polyurethane
photocurable
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陈东进
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Dongguan Lianzhou Intellectual Property Operation and Management Co Ltd
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Dongguan Lianzhou Intellectual Property Operation and Management Co Ltd
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    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/48—Polyethers
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    • C08G18/67—Unsaturated compounds having active hydrogen
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
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    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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    • C09J11/04—Non-macromolecular additives inorganic
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    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
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    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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    • C08L2205/16—Fibres; Fibrils

Abstract

The invention discloses a kind of UV photocurable polyurethane acrylates adhesives, including following components：100 parts of urethane acrylate, 20 35 parts of EEA resins (ethylene ethyl acrylate copolymer), 15 28 parts of lignin fibre, 20 36 parts of tri (propylene glycol) diacrylate, 25 40 parts of pentaerythritol triacrylate, 59 parts of light trigger, 15 22 parts of diabase, 58 parts of coupling agent, 8 11 parts of stabilizer, 12 parts of preservative, 35 parts of defoamer, 8 13 parts of toughener, 25 parts of antioxidant.The adhesive of the application can be with rapid curing under UV light irradiations, and caking property is strong, and has stronger impact resistance, ageing resistance and weatherability, and service life is longer, and suitable liquid crystal display is installed and used.

Description

A kind of UV photocurable polyurethane acrylates adhesives and preparation method thereof
Technical field
The present invention relates to adhesive area, more particularly to a kind of UV photocurable polyurethane acrylates adhesives and its system Preparation Method.
Background technology
UV photocurings refer to that in the presence of UV light the light trigger in system can absorb the light in certain wavelength band Generation active group can be cracked, so as to which some groups in initiation system carry out the photochemical reaction of photo-crosslinking polymerization, is realized The quick-setting curing technology of matrix surface.Photocuring technology solves the disadvantages for needing largely to use organic solvent in traditional handicraft End, environmental pollution is smaller, while it has that curing rate is fast, save the energy, expense is relatively low, cured product performance is excellent etc. is excellent Point, have been widely used for the fields such as adhesive, coating.Photocuring technology energy- and time-economizing, even it can just solidify less than one side within several seconds For hard, wear-resisting and attractive in appearance cured coating film；Equipment volume needed for solidification process is smaller, and investment is low, it is not necessary to extra Drying plant, it is adapted to continuous production.Photocuring adhesive is one of main application fields of photocuring technology, because its is many excellent Point receives the extensive concern of people.
Photocuring adhesive is for main component with resin, light trigger, reactive diluent etc., then is equipped with other auxiliary agent groups Into.Photocuring adhesive is under ultraviolet light, and light trigger cracks after absorbing luminous energy, generates ion or free radical triggers glue Matrix and reactive diluent in glutinous agent system polymerize, and are cross-linked into 3 D stereo network structure so as to reach binding material Effect.Photocuring adhesive can be divided into radical UV curing type, cation photocuring type according to its curing mechanism, mix light consolidates Change type and dual light-cured type.Wherein base resin is photocuring system important component, decide solidfied material pliability, Hardness, adhesion strength etc., its own structure influence also very big on laser curing velocity.
The bulk composition of general UV curable adhesives is esters of acrylic acid, by changing its molecular chain structure and relative point The size of protonatomic mass, thus it is possible to vary the performance such as hardness, compliance, solvent resistance and permanent seal cooling of adhesive.Esters of acrylic acid The curing rate of curable adhesive is by the relative molecular mass of used polyacrylate, the species of functional group and property It is related.Acrylate adhesive is modified using polyurethane, the advantages of polyurethane adhesive can be integrated into acrylic acid In ester gum stick so that product has more excellent combination property.
Chinese patent CN201410740133.2 discloses a kind of polyether polyurethane-acrylate ultraviolet cured adhesive and glued Agent and preparation method thereof；The adhesive of the invention is made up of the raw material of following parts by weight：Polyether polyurethane-acrylate 20~ 70 parts, 10~40 parts of assisted resin, 5~20 parts of ethylene-acrylate rubber, 5~40 parts of acrylate monomer, the different ice of acrylic acid 0.5~2 part of 5~35 parts of piece ester, 1~7 part of light trigger, 1~5 part of aerosil and silane coupler.The invention introduces Polyether polyurethane-acrylate, assisted resin, ethylene-acrylate rubber and acrylate monomer, the ultraviolet light solidification of preparation Adhesive has more excellent long-term heat-resisting quantity, lower temperature resistance and high temperature and humidity resistance, possesses more excellent impact resistance Can, and cost is low, preparation method is simple.
The content of the invention
It is an object of the invention to provide a kind of UV photocurable polyurethane acrylates adhesives, the adhesive is in UV light irradiations Under can be with rapid curing, caking property is strong, and has stronger impact resistance, ageing resistance and weatherability, service life compared with Long, suitable liquid crystal display is installed and used.
It is a further object of the present invention to provide the preparation method of the UV photocurable polyurethane acrylates adhesives.
To achieve the above object, the present invention uses following technical scheme：
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, EEA resins (ethylene-ethyl acrylate copolymer) 20-35 parts, lignin fibre 15-28 parts, tri (propylene glycol) diacrylate 20-36 parts, pentaerythritol triacrylate 25-40 parts, light trigger 5-9 Part, diabase 15-22 parts, coupling agent 5-8 parts, stabilizer 8-11 parts, preservative 1-2 parts, defoamer 3-5 parts, toughener 8-13 Part, antioxidant 2-5 parts；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers.
Preferably, the PCDL, pyromellitic dianhydride, PolyTHF trihydroxylic alcohol, the use matter of polypropylene glycol Amount is than being 35：17：29：9.
Preferably, the light trigger is the mixture of methyl diethanolamine and 4- padimates.
Preferably, the coupling agent is titante coupling agent.
Preferably, the stabilizer is zinc stearate.
Preferably, the preservative is sodium benzoate.
Preferably, the defoamer is polypropylene glycerol aether.
Preferably, the toughener is ABS rubber and ethylene-methyl acrylate copolymer.
Preferably, antioxidant is the mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, is comprised the steps of：
(1) it will be dispersed in water after diabase flour breakdown mill, after stirring makes it well mixed, coupling agent be added dropwise thereto, Continue after being ultrasonically treated 45-60min, stand 12-16h, filter, drying, modified diabase powder is made after grinding；
(2) urethane acrylate, EEA resins and lignin fibre are added in kneading machine and be kneaded under the conditions of 150 DEG C 15-30min, mixture is put into reactor, regulation temperature adds modified diabase powder after being 180 DEG C, two contractings 3 the third two Alcohol diacrylate, pentaerythritol triacrylate, light trigger, coupling agent, stabilizer, preservative, defoamer, toughener, After antioxidant is well mixed, after excluding bubble, be cooled to normal temperature, both the UV photocurable polyurethane acrylates adhesives.
The invention has the advantages that
Using PCDL, pyromellitic dianhydride, PolyTHF trihydroxylic alcohol, polypropylene glycol and HMDI synthesis of polyurethane After performed polymer again with carboxy ethyl acrylate reaction made from bulk composition of the urethane acrylate as adhesive, the polyurethane Acrylate cross linked property is strong, has good caking property and shock resistance.Lignin fibre is that natural timber passes through at chemistry Obtained organic fiber is managed, there is good toughness and higher chemical stability, solvent resistant, acid and alkali corrosion.The application is led to Cross and add lignin fibre in adhesive, effectively raise the tensile resistance of adhesive, and adhesive can be provided Protection improves the weatherability of adhesive.Diabase can effectively improve the adhesive property of adhesive.
Embodiment
In order to be better understood from the present invention, below by embodiment, the present invention is further described, and embodiment is served only for solving The present invention is released, any restriction will not be formed to the present invention.
Embodiment 1
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, 20 parts of EEA resins, 15 parts of lignin fibre, tri (propylene glycol) diacrylate 20 parts, 25 parts of pentaerythritol triacrylate, 5 parts of light trigger, 15 parts of diabase, 5 parts of titante coupling agent, zinc stearate 8 parts, 1 part of sodium benzoate, 3 parts of polypropylene glycerol aether, 8 parts of toughener, 2 parts of antioxidant；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers；The PCDL, pyromellitic acid Acid anhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9；Light trigger be methyl diethanolamine and The mixture of 4- padimates；Toughener is ABS rubber and ethylene-methyl acrylate copolymer；Antioxidant is The mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, is comprised the steps of：
(1) it will be dispersed in water after diabase flour breakdown mill, after stirring makes it well mixed, titanate ester be added dropwise thereto Coupling agent, continue after being ultrasonically treated 50min, stand 14h, filter, drying, modified diabase powder is made after grinding；
(2) urethane acrylate, EEA resins and lignin fibre are added in kneading machine and be kneaded under the conditions of 150 DEG C 30min, mixture is put into reactor, regulation temperature adds modified diabase powder, tripropylene glycol two after being 180 DEG C Acrylate, pentaerythritol triacrylate, light trigger, coupling agent, zinc stearate, sodium benzoate, polypropylene glycerol aether, Toughener, after antioxidant is well mixed, after excluding bubble, be cooled to normal temperature, both the UV curable urethane acrylates Adhesive.
Embodiment 2
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, 35 parts of EEA resins, 28 parts of lignin fibre, tri (propylene glycol) diacrylate 36 parts, 40 parts of pentaerythritol triacrylate, 9 parts of light trigger, 22 parts of diabase, 8 parts of titante coupling agent, zinc stearate 11 parts, 2 parts of sodium benzoate, 5 parts of polypropylene glycerol aether, 13 parts of toughener, 5 parts of antioxidant；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers；The PCDL, pyromellitic acid Acid anhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9；Light trigger be methyl diethanolamine and The mixture of 4- padimates；Toughener is ABS rubber and ethylene-methyl acrylate copolymer；Antioxidant is The mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, it is same as Example 1.
Embodiment 3
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, 20 parts of EEA resins, 28 parts of lignin fibre, tri (propylene glycol) diacrylate 20 parts, 40 parts of pentaerythritol triacrylate, 5 parts of light trigger, 22 parts of diabase, 5 parts of titante coupling agent, zinc stearate 11 parts, 1 part of sodium benzoate, 5 parts of polypropylene glycerol aether, 8 parts of toughener, 5 parts of antioxidant；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers；The PCDL, pyromellitic acid Acid anhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9；Light trigger be methyl diethanolamine and The mixture of 4- padimates；Toughener is ABS rubber and ethylene-methyl acrylate copolymer；Antioxidant is The mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, it is same as Example 1.
Embodiment 4
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, 35 parts of EEA resins, 15 parts of lignin fibre, tri (propylene glycol) diacrylate 36 parts, 25 parts of pentaerythritol triacrylate, 9 parts of light trigger, 15 parts of diabase, 8 parts of titante coupling agent, zinc stearate 8 parts, 2 parts of sodium benzoate, 3 parts of polypropylene glycerol aether, 13 parts of toughener, 2 parts of antioxidant；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers；The PCDL, pyromellitic acid Acid anhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9；Light trigger be methyl diethanolamine and The mixture of 4- padimates；Toughener is ABS rubber and ethylene-methyl acrylate copolymer；Antioxidant is The mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, it is same as Example 1.
Embodiment 5
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, 23 parts of EEA resins, 17 parts of lignin fibre, tri (propylene glycol) diacrylate 24 parts, 29 parts of pentaerythritol triacrylate, 6 parts of light trigger, 17 parts of diabase, 6 parts of titante coupling agent, zinc stearate 9 parts, 1 part of sodium benzoate, 4 parts of polypropylene glycerol aether, 9 parts of toughener, 3 parts of antioxidant；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers；The PCDL, pyromellitic acid Acid anhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9；Light trigger be methyl diethanolamine and The mixture of 4- padimates；Toughener is ABS rubber and ethylene-methyl acrylate copolymer；Antioxidant is The mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, it is same as Example 1.
Embodiment 6
A kind of UV photocurable polyurethane acrylates adhesives, in parts by weight, including following components：
100 parts of urethane acrylate, 31 parts of EEA resins, 24 parts of lignin fibre, tri (propylene glycol) diacrylate 33 parts, 36 parts of pentaerythritol triacrylate, 7 parts of light trigger, 17 parts of diabase, 7 parts of titante coupling agent, zinc stearate 10 parts, 2 parts of sodium benzoate, 4 parts of polypropylene glycerol aether, 11 parts of toughener, 4 parts of antioxidant；
The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, poly- the third two It is made again with carboxy ethyl acrylate reaction after alcohol and HMDI synthesis of polyurethane performed polymers；The PCDL, pyromellitic acid Acid anhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9；Light trigger be methyl diethanolamine and The mixture of 4- padimates；Toughener is ABS rubber and ethylene-methyl acrylate copolymer；Antioxidant is The mixture of irgasfos 168 and antioxidant 264.
A kind of preparation method of UV photocurable polyurethane acrylates adhesives, it is same as Example 1.
After the cured processing of adhesive obtained by embodiment 1-6, the test of mechanical property is carried out, and comparative example is entered Go same test, it is as a result as shown in the table, wherein, comparative example is commercially available UV photocurable polyurethane acrylates adhesives；
Impact strength is tested with reference to GB/T1843-1996, and impact strength is higher to show that performance is better；
1-6 of embodiment of the present invention impact strength shows there is preferable shock resistance obviously higher than comparative example.

Claims (10)

  1. A kind of 1. UV photocurable polyurethane acrylates adhesives, it is characterised in that in parts by weight, including following components：
    100 parts of urethane acrylate, EEA resins (ethylene-ethyl acrylate copolymer) 20-35 parts, lignin fibre 15-28 Part, tri (propylene glycol) diacrylate 20-36 parts, pentaerythritol triacrylate 25-40 parts, light trigger 5-9 parts, brightness are green Rock 15-22 parts, coupling agent 5-8 parts, stabilizer 8-11 parts, preservative 1-2 parts, defoamer 3-5 parts, toughener 8-13 parts, antioxygen Agent 2-5 parts；
    The urethane acrylate is the pyromellitic dianhydride by PCDL, PolyTHF trihydroxylic alcohol, polypropylene glycol and It is made again with carboxy ethyl acrylate reaction after HMDI synthesis of polyurethane performed polymers.
  2. 2. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The makrolon Glycol, pyromellitic dianhydride, PolyTHF trihydroxylic alcohol, the use quality ratio of polypropylene glycol is 35：17：29：9.
  3. 3. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The light trigger For methyl diethanolamine and the mixture of 4- padimates.
  4. 4. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The coupling agent is Titante coupling agent.
  5. 5. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The stabilizer is Zinc stearate.
  6. 6. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The preservative is Sodium benzoate.
  7. 7. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The defoamer is Polypropylene glycerol aether.
  8. 8. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：The toughener is ABS rubber and ethylene-methyl acrylate copolymer.
  9. 9. UV photocurable polyurethane acrylates adhesives according to claim 1, it is characterised in that：Antioxidant is antioxygen Agent 168 and the mixture of antioxidant 264.
  10. 10. the preparation method of the UV photocurable polyurethane acrylates adhesives according to claim any one of 1-9, it is special Sign is：Comprise the steps of：
    (1) it will be dispersed in water after diabase flour breakdown mill, after stirring makes it well mixed, coupling agent be added dropwise thereto, continues After being ultrasonically treated 45-60min, 12-16h is stood, is filtered, drying, modified diabase powder is made after grinding；
    (2) urethane acrylate, EEA resins and lignin fibre are added in kneading machine and is kneaded 15- under the conditions of 150 DEG C 30min, mixture is put into reactor, regulation temperature adds modified diabase powder, tripropylene glycol two after being 180 DEG C Acrylate, pentaerythritol triacrylate, light trigger, coupling agent, stabilizer, preservative, defoamer, toughener, antioxygen After agent is well mixed, after excluding bubble, be cooled to normal temperature, both the UV photocurable polyurethane acrylates adhesives.
CN201710770693.6A 2017-08-31 2017-08-31 A kind of UV photocurable polyurethane acrylates adhesives and preparation method thereof Pending CN107446540A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109294511A (en) * 2018-09-03 2019-02-01 佛山艾仕仑科技有限公司 A kind of UV curing adhesive suitable for flexible parent metal bonding
CN115477912A (en) * 2022-05-13 2022-12-16 西南化工研究设计院有限公司 Preparation and application of bio-based ultraviolet curing adhesive for wet-process laminated inductor production

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Publication number Priority date Publication date Assignee Title
CN102359490A (en) * 2011-08-31 2012-02-22 北京航空航天大学 Five-freedom radial decoupling conical magnetic bearing
CN103173144A (en) * 2011-12-26 2013-06-26 第一毛织株式会社 Composition for anisotropic conductive adhesive film, anisotropic conductive adhesive film and semiconductor device
CN104531041A (en) * 2014-12-05 2015-04-22 烟台泰盛精化科技有限公司 Polyether-type urethane acrylate UV-cured adhesive and preparation method thereof

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Publication number Priority date Publication date Assignee Title
CN102359490A (en) * 2011-08-31 2012-02-22 北京航空航天大学 Five-freedom radial decoupling conical magnetic bearing
CN103173144A (en) * 2011-12-26 2013-06-26 第一毛织株式会社 Composition for anisotropic conductive adhesive film, anisotropic conductive adhesive film and semiconductor device
CN104531041A (en) * 2014-12-05 2015-04-22 烟台泰盛精化科技有限公司 Polyether-type urethane acrylate UV-cured adhesive and preparation method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109294511A (en) * 2018-09-03 2019-02-01 佛山艾仕仑科技有限公司 A kind of UV curing adhesive suitable for flexible parent metal bonding
CN109294511B (en) * 2018-09-03 2021-06-01 佛山艾仕仑科技有限公司 UV curing adhesive suitable for bonding flexible base materials
CN115477912A (en) * 2022-05-13 2022-12-16 西南化工研究设计院有限公司 Preparation and application of bio-based ultraviolet curing adhesive for wet-process laminated inductor production

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Application publication date: 20171208