CN101392151B - Ultraviolet ray/anaerobic dual curing binding agent and preparation method thereof - Google Patents
Ultraviolet ray/anaerobic dual curing binding agent and preparation method thereof Download PDFInfo
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- CN101392151B CN101392151B CN 200810218889 CN200810218889A CN101392151B CN 101392151 B CN101392151 B CN 101392151B CN 200810218889 CN200810218889 CN 200810218889 CN 200810218889 A CN200810218889 A CN 200810218889A CN 101392151 B CN101392151 B CN 101392151B
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Abstract
The invention discloses an ultraviolet/anaerobic double-curing adhesive which comprises components with the following parts by weight: altogether 100 portions of monomer or oligomer comprising vinyl or a mixture of both, 0.01 portion to 0.5 portion of inhibitor, 0.1 portion to 10 portions of photo-initiator and an appropriate portion of anaerobic-adhesive initiator; the anaerobic-adhesive initiator comprises components with the following weight portions: 0.05 portion to 5 portions of organic hydrazide, 0.05 portion to 5 portions of tertiary amine, 0.01 portion to 2 portions of ascorbic acid, 0 portion to 1 portion of ascorbate, 0.1 portion to 5 portions of saccharin, 0 portion to 1 portion of saccharin salt, 0.5 portion to 5 portions of organic salt and 0.5 portion to 10 portions of organic peroxide. The invention also provides a preparation method of the adhesive, which comprises the steps as follows: the other components, except the organic peroxide and the photo-initiator, are mutually blended for dissolution by the conventional method; then the photo-initiator is added and dissolved; and the organic peroxide is added and mixed evenly at the temperature below 40 DEG C, and finally the adhesive is prepared. The adhesive has not only highly efficient anaerobic curing performance, but also excellent adhesive performance as an ultraviolet curing adhesive, with wide application prospect.
Description
Technical field
The present invention relates to a kind ofly not only can solidify but also the tackiness agent of anaerobically curable and preparation method thereof through uviolizing.
Background technology
Ultraviolet curing adhesive is a kind ofly to have curing and rapidly, do not contain the tackiness agent that VOC, environmental protection, bonding force are strong, do not have heat effect, characteristics such as applied widely when solidifying.Ultraviolet curing glue can solidify rapidly under uviolizing, but for opaque base material be in the slit corner portions located, accept the energy shortage of irradiation, tackiness agent can not fully solidify, and can not form effectively bonding.Prior art is in binder compsn, to add the thermofixation composition to this way to solve the problem; Thereby this part tackiness agent that is not exposed to uviolizing can be cured through heating; Yet this method need be acquired equipment such as baker in addition; Troublesome poeration, and can not be used for temperature-sensitive material.Second method is the composition that in binder compsn, adds moisture-curable.This method also is unfavorable, because can receiving influence of moisture, compsn solidifies in advance through the shelf lives of being everlasting, and active reduction the when causing exceeding the time limit to store, and also curing depth is limited.
Anaerobic glue be a kind of be the tackiness agent of main body composition with unsaturated compounds such as propenoate or methacrylic esters, when contacting, do not solidify and can keep liquid state for a long time with air or oxygen, under the situation that has completely cut off air or oxygen, solidify rapidly.Based on this character, anaerobic glue is by with the sealing between being connected of the locking of screw thread, axle and bearing, the flange etc.When used for anaerobic adhesive during in big gap bonding be exposed to airborne glue and can not well solidify, this has also just limited the range of application of anaerobic glue.Similar property based on the main body composition of ultraviolet curing and anaerobic glue; The complementarity of curing performance; Someone attempts with these two kinds of adhesive bond together; Work out a kind of ultraviolet ray/anaerobic dual curing binding agent, this tackiness agent can solidify down through uviolizing, again can be under secluding air or oxygen condition anaerobic curing.When its be applied between the lighttight material uviolizing when bonding less than the sol in gap because of the secluding air anaerobic curing, excessive tree lace is accepted uviolizing and is solidified.Yet because the complicacy of anaerobic glue composition; The composition of ultraviolet curing glue and anaerobic glue composition regular meeting influence each other; For example some compositions of ultraviolet curing glue such as adhesion promoter, light trigger etc. can cause anaerobic curing speed to slow down, and some components of anaerobic glue can make the surface drying property variation of tackiness agent or the intensity after the influence curing.Therefore this professional skill field needs a kind of ultraviolet ray/anaerobic dual curing binding agent of excellent combination property.
Summary of the invention
The present invention seeks to provides a kind of ultraviolet ray/anaerobic dual curing binding agent in order to overcome the deficiency of prior art, and the existing speed of anaerobic curing is not fast lost the adhesiveproperties as the excellence of ultraviolet curing glue again.
Another object of the present invention provides the preparation method of above-mentioned tackiness agent.
The present invention realizes above-mentioned purpose through following technical proposals:
A kind of ultraviolet ray/anaerobic dual curing binding agent, process by the component of following parts by weight:
Totally 100 parts in monomer or oligopolymer or the mixture of the two containing vinyl, 0.01～0.5 part of stopper, 0.5～10 part of organo-peroxide, 0.1～10 part of light trigger, 2～20 parts of anaerobic glue initiators;
The component that consists of following parts by weight of said anaerobic glue initiator: 0.05～5 part of organic hydrazides; 0.05～5 part of tertiary amine, 0.01～2 part in xitix, 0～1 part of ascorbate salt; 0.1～5 part of saccharin; 0～1 part of saccharin salt, 0.5～5 part of organic acid, 0.5～10 part of organo-peroxide.
Contain the group shown at least one formula I in the described monomer that contains vinyl or its molecule of oligopolymer:
R is hydrogen or methyl in the formula.
The described monomer that contains vinyl is selected from mono acrylic ester, diacrylate, many propenoate or monomethacrylates, dimethacrylate, many methacrylic esters.This compounds is for example: Hydroxyethyl acrylate; Diethylene glycol diacrylate; 2-(2-ethoxy ethoxy) ethyl propylene acid esters; Pentaerythritol triacrylate; Rocryl 400; Rocryl 410; TGM 1; The triethylene glycol dimethacrylate; The tripropylene glycol dimethacrylate; Polyethylene glycol dimethacrylate; The ethoxyquin bisphenol a dimethacrylate; Trimethylolpropane trimethacrylate; Ethoxyquin trimethylolpropane trimethacrylate etc.
The said oligopolymer that contains vinyl is selected from epoxy acrylate, urethane acrylate or polyester acrylate; Wherein epoxy acrylate is by epoxy resin and the reaction of acrylic or methacrylic acid esters and make, and according to structure type bisphenol-a epoxy acrylate is arranged, phenolic aldehyde epoxy acrylate, modified epoxy acrylic ester or epoxidized oil propenoate; Urethane acrylate is the compound that contains several Urethylane chain links
in its molecule; And contain two above propenoate or methacrylate end-groups at least; This compounds is by POLYMETHYLENE POLYPHENYLISOCYANATE, long chain diol, hydroxy functional acrylate synthetic; Can in very large range regulate its performance according to raw material of being selected for use and technology; Like hardness, flexibility, tolerance etc.; Said polyester acrylate is by diprotic acid, divalent alcohol, and the acrylic or methacrylic acid-respons makes.
Ultraviolet ray/anaerobic dual curing binding agent of the present invention; Can contain a kind of to multiple monomer or a kind of extremely multiple oligopolymer that contains vinyl that contains vinyl; Also can contain a kind of simultaneously to multiple monomer and a kind of extremely multiple oligopolymer that contains vinyl that contains vinyl; Be preferably and contain a kind ofly to the multiple monomer that contains vinyl and a kind of to the multiple oligopolymer that contains vinyl simultaneously, its total amount is 100 parts according to the mass fraction.
Tackiness agent of the present invention can also contain the conventional light trigger of 0.1～10 weight part, and said light trigger is selected from the st-yrax that belongs to the bitter almond oil camphor class, benzoin isopropyl ether, benzoin isobutyl ether, benzoin dimethylether etc.; Belong to 2 of acetophenone derivs class, 2-diethoxy acetophenone, to phenoxy-α, α-dichloroacetophenone, hydroxy-cyclohexyl methyl phenyl ketone, α, alpha-alpha-dimethyl-Alpha-hydroxy methyl phenyl ketone etc.; The UVNUL MS-40, diphenyl antimony chloride ketone, acroleic acid esterification UVNUL MS-40, the 4-phenyl benzophenone, 3 that belong to benzophenone, 3-dimethyl--4-methoxy benzophenone etc.; The 2-chlorination thioxanthone, the isopropyl thioxanthone, 2 that belong to thioxanthones, 4-dimethyl-thia anthrone, 2,4-two chlorothiaxanthenones etc.; Belong to 2,4 of acylphosphine oxide, 6-Three methyl Benzene formyl diethyl phosphonate, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide etc.; Some light trigger is a patented product; Like the IRGACURE 907 of vapour Bagong department, IRGACURE 369, IRGACURE 784, DAROCUR 4263, DAROCUR 4265, IRGACURE 754, IRGACURE819, IRGACURE 2022, IRGACURE 250 etc., the Lucirin BAPO of BASF AG, LucirinTPO, Lucirin TPO-L, Lucirin TMPO, Lucirin TEPO etc.
Said light trigger can select one or more conventional light trigger to mix use; The reasonable composite use of two or more light trigger is helpful for the curing performance that improves tackiness agent; Can widen the wavelength region of absorption; Improve surface drying property, obtain the solidified surface of dry and comfortable property.Light trigger is the key component of photocuring system; Thereby can behind ultraviolet ray that has absorbed certain part wavelength or visible light, produce radical and cause the glue polymerizing curable; Light trigger is of a great variety, and the wavelength region of absorption can drop on ultraviolet region (250～420nm) or visible region (400～800nm) according to different kinds.
Can also add as required in the ultraviolet ray/anaerobic dual curing binding agent of the present invention compound bearing active hydrogen can be provided; These materials and light trigger are used can improve ultraviolet curing speed, improve surface drying property; Use benzophenone or thioxanthones carry the Hydrogen light trigger time; Can provide compound bearing active hydrogen to exist simultaneously; Because this type carried the light trigger of Hydrogen and need can be provided under the condition that compound bearing active hydrogen exists having, just can receive ultraviolet ray excited generation radical and cause curing reaction.The said normally tertiary amine of compound bearing active hydrogen that provides; Be called as reactive amines; Optional example is triethylamine, trolamine, N for example, N-dimethylethanolamine, N, N-diethylethanolamine, N-methyl-diethylolamine, vinylformic acid (N; The N-dimethylamino) ethyl ester or p-(dimethylamino)-benzoic acid ester etc., the parts by weight of adding are 0～10 part.
Described organic hydrazides is the compound that comprises
structure in the molecule; Be selected from benzoyl hydrazine, N-pyrodin, para hydroxybenzene formyl hydrazine or 4-tert.-butylbenzene formyl hydrazine, preferably benzoyl hydrazine and N-pyrodin.
Described tertiary amine is aliphatic tertiary amine or aromatic nitrile base, for example tri-n-butylamine, triethylamine, trolamine or N, and N-xylidine is preferably tri-n-butylamine or triethylamine.
Described ascorbate salt is sodium, potassium or the calcium salt of xitix.
Sodium, potassium or calcium salt that described saccharin salt is saccharin.
Described organic acid is carboxylic acid, chlorinated carboxylic acid or sulfonic compound, like acetate, trichoroacetic acid(TCA), dichloro acetic acid or Phenylsulfonic acid; Preferably intramolecularly contains the carboxylic acid of two keys, like vinylformic acid, methylacrylic acid, toxilic acid, methylene-succinic acid etc.
Described organo-peroxide be contain one to a plurality of peroxy-O-O-; Be selected from dialkyl peroxide, alkyl peroxide or alkyl peroxy acids and peracid ester compound; For example peroxo-diisopropyl benzene, tert-butyl hydroperoxide isopropyl benzene, isopropyl benzene hydroperoxide, tertbutyl peroxide, Lucidol, peroxidized t-butyl perbenzoate, 2; 5-dimethyl--2; 5-(di-tert-butyl peroxide) hexane or ring have been pitched the diperoxy thing, and optional one or more mix use.
Described stopper is one type of polymerization retarder, generally is phenols or quinones, is selected from one or more mixing uses in Resorcinol, p-tert-butylphenol, p methoxy phenol, para benzoquinone or the naphthoquinones.
In addition, tackiness agent of the present invention can also add the thickening material (or being called thixotropic agent) that is used to adjust viscosity where necessary, like polymethylmethacrylate, PVA or aerosil; Or adding is used to regulate the softening agent such as the Witcizer 300 of intensity; Or adding is as disodium EDTA, trisodium salt or the tetra-na salt of sequestrant; Or adding adhesion promoter, silane coupling agent, tinting material, mask agent and other conventional auxiliary agents.Whether these materials need add or add on a small quantity according to the performance requriements of the different varieties of ultraviolet ray/anaerobic dual curing glue is decided.
The preparation method of ultraviolet ray/anaerobic dual curing binding agent of the present invention is by the mutual mixed dissolution of ordinary method with other each components except that organo-peroxide and light trigger; Also can be heated to 50～70 ℃ with hydrotropy; Add the light trigger mixed dissolution then, add down organo-peroxides and mix and make being lower than 40 ℃ at last.
Compared with prior art, the present invention has following beneficial effect:
Anaerobic glue initiator regular meeting commonly used receives the influence of some compositions in the ultraviolet curing glue, can make the efficient of anaerobic glue initiator system reduce like adhesion promoter, light trigger, amine acvator, causes solidification rate to slow down.Initiator in the opposite anaerobic glue and methacrylic ester also can make the reduction of ultraviolet curing speed, surface drying property variation; And the present invention cooperates general promotor such as organic hydrazides, tertiary amine to reach preferred anaerobic glue initiator system through adding xitix, ascorbate salt, saccharin salt; An initiator system efficiently is provided; Do not lower its adhesiveproperties again, make the superior ultraviolet ray/anaerobic dual curing binding agent of over-all properties.
The ultraviolet ray/anaerobic dual curing binding agent that the present invention makes, the existing performance of anaerobic curing is not efficiently lost the excellent viscosity ability as ultraviolet curing glue again.Can use in some occasions that can not use with simple ultraviolet curing glue and anaerobic glue, have broad application prospects in technical fields such as industry such as electronics, electromechanics, instrument, artworks.
Embodiment
Below further specify technical scheme of the present invention through concrete embodiment.
Said umber is parts by weight.
Embodiment 1
With 40 parts of dimethacrylate triglycol esters, 60 parts of epoxy acrylate oligomers, 0.05 part of Resorcinol, 0.5 part of pyrodin; 0.5 part of tri-n-butylamine, 0.1 part in xitix, saccharin mixes to dissolving for 1 part; Add light trigger α then, 3 parts of alpha-alpha-dimethyls-Alpha-hydroxy methyl phenyl ketone add 2 parts of isopropyl benzene hydroperoxides down being lower than 40 ℃ at last; After mixing, be sub-packed in the new LDPE (film grade) bottle of black, be filled to 2/3 bottle at most.
Embodiment 2～9, press the formula ratio sampling preparation shown in the table 1, and compound method is with embodiment 1.
The tackiness agent prescription of table 1 embodiment 2～9
| Embodiment | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
| Epoxy acrylate | 60 | 60 | -- | 60 | -- | -- | 60 | -- |
| Urethane acrylate | -- | -- | 60 | -- | 60 | 60 | -- | 60 |
| Rocryl 400 | 40 | -- | 40 | -- | -- | 20 | 20 | -- |
| The 2-phenoxyethyl acrylate | -- | 20 | -- | 40 | 40 | -- | -- | 20 |
| Tripropylene glycol diacrylate | -- | 20 | -- | -- | -- | 20 | 20 | 20 |
| Resorcinol | 0.05 | 0.05 | 0.02 | 0.02 | 0.02 | 0.02 | 0.02 | 0.02 |
| Pyrodin | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
| Tri-n-butylamine | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
| Xitix | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Sodium ascorbate | -- | -- | -- | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
| Saccharin | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
| Saccharin sodium | -- | -- | -- | -- | 0.05 | 0.05 | 0.05 | 0.05 |
| Isopropyl benzene hydroperoxide | 2 | 2 | 2 | 2 | -- | -- | 2 | 2 |
| Tertiary butyl hydrogen oxide | -- | -- | -- | -- | 2 | 2 | -- | -- |
| α, alpha-alpha-dimethyl-Alpha-hydroxy methyl phenyl ketone | 3 | 3 | 3 | 3 | 3 | -- | -- | -- |
| 1-hydroxy-cyclohexyl methyl phenyl ketone | -- | -- | -- | -- | -- | 3 | -- | -- |
| The st-yrax n-butyl ether | -- | -- | -- | -- | -- | -- | 3 | -- |
| 2,4,6-trimethylbenzoyl diphenyl phosphine oxide | -- | -- | -- | -- | -- | -- | -- | 2 |
Comparative Examples 1～3 is pressed the formula ratio sampling preparation shown in the table 2, and compound method is with embodiment 1.
The tackiness agent prescription of table 2 Comparative Examples 1～3
| Comparative Examples | 1 | 2 | 3 |
| Epoxy acrylate | 60 | 60 | -- |
| Urethane acrylate | -- | -- | 60 |
| Rocryl 400 | 40 | -- | 40 |
| The 2-phenoxyethyl acrylate | -- | 20 | -- |
| Tripropylene glycol diacrylate | -- | 20 | -- |
| Resorcinol | 0.05 | 0.05 | 0.02 |
| Pyrodin | 0.5 | -- | 0.5 |
| N, the N-dimethyl-p-toluidine | -- | 0.5 | 0.5 |
| Saccharin | 1 | 1 | 1 |
| Isopropyl benzene hydroperoxide | 2 | -- | 2 |
| Tertiary butyl hydrogen oxide | -- | 2 | -- |
| α, alpha-alpha-dimethyl-Alpha-hydroxy methyl phenyl ketone | 3 | 3 | -- |
| 1-hydroxy-cyclohexyl methyl phenyl ketone | -- | -- | 3 |
The curability test:
Solidification rate (anaerobic curing time) is measured: process 100 * 25mm test piece with the 40# steel, with the foregoing description and each compsn of comparative example, intersected with each otherly carry out bondingly, overlap the about 15 * 25mm of area, and load the 10g counterweight above that and fix.25 ℃ the mensuration intersection irremovable time of test piece is setting time down in room temperature.The result sees table 3.
Shearing resistance is measured: iron/iron shears shearing stress, process 100 * 25mm test piece with the 40# steel, and with the foregoing description and each compsn of comparative example, intersected with each otherly carry out bondingly, overlap the about 12.5 * 25mm of area, and load the 100g counterweight above that and fix.Solidify down for 25 ℃ in room temperature, test shearing resistance with tension testing machine after 24 hours.The result sees table 3.
The PMMA/PMMA shearing resistance; Process 25 * 25 * 10 test blocks with transparent PMMA; With the foregoing description and each compsn of comparative example, intersected with each other carry out bonding, overlap joint area about 12.5 * 25mm; With 400W ultra violet lamp 15 seconds, place after 24 hours and carry out the test of piece shearing resistance by ASTMD4501 with tension testing machine.The result sees table 3.
Table 3 embodiment and comparative example curability test result
Show ultraviolet ray/anaerobic dual curing binding agent of the present invention from top example test result, have efficiently anaerobic curing performance fast, do not lose again as ultraviolet curing glue.Has excellent viscosity ability for metal and plastics.
Claims (8)
1. ultraviolet ray/anaerobic dual curing binding agent is made up of the component of following parts by weight: contain 100 parts in monomer or oligopolymer or the mixture of the two of vinyl, 0.01～0.5 part of stopper, 0.1～10 part of light trigger, 2～20 parts of anaerobic glue initiators totally;
Said anaerobic glue initiator is made up of the component of following parts by weight: 0.05～5 part of organic hydrazides; 0.05～5 part of tertiary amine, 0.01～2 part in xitix, 0～1 part of ascorbate salt; 0.1～5 part of saccharin; 0～1 part of saccharin salt, 0.5～5 part of organic acid, 0.5～10 part of organo-peroxide;
The said monomer that contains vinyl is selected from mono acrylic ester, diacrylate, many propenoate or monomethacrylates, dimethacrylate, many methacrylic esters;
The said oligopolymer that contains vinyl is selected from epoxy acrylate, urethane acrylate or polyester acrylate.
2. tackiness agent as claimed in claim 1 is characterized in that: described stopper is to be selected from Resorcinol, p-tert-butylphenol, p methoxy phenol, para benzoquinone or the naphthoquinones one or more.
3. tackiness agent as claimed in claim 2 is characterized in that: described organic hydrazides is selected from benzoyl hydrazine, N-pyrodin, para hydroxybenzene formyl hydrazine or 4-tert.-butylbenzene formyl hydrazine; Described tertiary amine is tri-n-butylamine, triethylamine, trolamine or N, accelerine; Described ascorbate salt is sodium salt, sylvite or the calcium salt of xitix; Sodium salt, sylvite or calcium salt that described saccharin salt is saccharin; Described organic acid is carboxylic acid, chlorinated carboxylic acid or sulfonic compound; Described organo-peroxide is selected from one or more in dialkyl peroxide, alkyl peroxide, alkyl peroxo-acid or the peracid ester compound.
4. tackiness agent as claimed in claim 3 is characterized in that said light trigger is selected from one or more the mixture in the following substances: the st-yrax, benzoin isopropyl ether, benzoin isobutyl ether, the benzoin dimethylether that belong to the bitter almond oil camphor class; Belong to 2 of acetophenone derivs class, 2-diethoxy acetophenone, to phenoxy-α, α-dichloroacetophenone, hydroxy-cyclohexyl methyl phenyl ketone, α, alpha-alpha-dimethyl-Alpha-hydroxy methyl phenyl ketone; The UVNUL MS-40, diphenyl antimony chloride ketone, acroleic acid esterification UVNUL MS-40, the 4-phenyl benzophenone, 3 that belong to benzophenone, 3-dimethyl--4-methoxy benzophenone; The 2-chlorination thioxanthone, the isopropyl thioxanthone, 2 that belong to thioxanthones, 4-dimethyl-thia anthrone, 2,4-two chlorothiaxanthenones; Belong to 2 of acylphosphine oxide; 4; 6-Three methyl Benzene formyl diethyl phosphonate, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide; The IRGACURE 907 of vapour Bagong department, IRGACURE 369, IRGACURE 784, DAROCUR 4263, DAROCUR4265, IRGACURE 754, IRGACURE 819, IRGACURE 2022, IRGACURE 250, the Lucirin BAPO of BASF AG, Lucirin TPO, Lucirin TPO-L, Lucirin TMPO, Lucirin TEPO.
5. tackiness agent according to claim 4; It is characterized in that also adding the provided compound bearing active hydrogen of 0～10 weight part; The said compound bearing active hydrogen that provides is selected from triethylamine, trolamine, N; N-dimethylethanolamine, N, N-diethylethanolamine, N-methyl-diethylolamine, vinylformic acid (N, N-dimethylamino) ethyl ester or p-(dimethylamino)-benzoic acid ester.
6. tackiness agent as claimed in claim 5 is characterized in that also having added thickening material, softening agent, sequestrant, adhesion promoter, silane coupling agent, tinting material or mask agent.
7. the preparation method of the said tackiness agent of claim 1; It is characterized in that will be except that organo-peroxide and light trigger other each components by the mutual mixed dissolution of ordinary method; Add light trigger then and mix, dissolving mixes and makes adding organo-peroxide below 40 ℃ at last.
8. preparation method as claimed in claim 7 is characterized in that described dissolving is to be heated to 50～70 ℃ of dissolvings.
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| KR20100137972A (en) * | 2009-06-24 | 2010-12-31 | 삼성전자주식회사 | Sealant, liquid crystal display having the same and method of fabricating the same |
| KR20130072549A (en) * | 2011-12-22 | 2013-07-02 | 삼성전기주식회사 | Sealing resin composition for hdd motor and hdd motor fabricated by using the same |
| CN102969116B (en) * | 2012-07-20 | 2015-05-27 | 横店集团东磁股份有限公司 | UV (ultraviolet) solidified bonding magnet and preparation method thereof |
| CN104046280A (en) * | 2014-06-04 | 2014-09-17 | 重庆聚瑞化工新材料有限公司 | Anaerobic adhesive for sealing bowl-shaped plug of engine |
| CN107286305A (en) * | 2016-04-01 | 2017-10-24 | 陈珏 | A kind of laser fast shaping photosensitive resin material |
| CN106634795A (en) * | 2016-12-27 | 2017-05-10 | 深圳市荣昌科技有限公司 | UV (Ultraviolet) anaerobic adhesive |
| CN109957369B (en) * | 2019-03-29 | 2021-12-14 | 东莞初创应用材料有限公司 | Ultraviolet-curing black adhesive and preparation method thereof |
| CN110373115B (en) * | 2019-07-22 | 2022-04-05 | 中国兵器工业第五九研究所 | UV anaerobic sealant suitable for quickly sealing small workpieces |
| CN111234756B (en) * | 2020-03-09 | 2021-12-07 | 杭州电子科技大学 | UV-anaerobic dual-mode curing bonding material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101205451A (en) * | 2007-11-30 | 2008-06-25 | 华南理工大学 | Ultraviolet-anaerobic dual curing adhesive |
-
2008
- 2008-10-30 CN CN 200810218889 patent/CN101392151B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101205451A (en) * | 2007-11-30 | 2008-06-25 | 华南理工大学 | Ultraviolet-anaerobic dual curing adhesive |
Non-Patent Citations (2)
| Title |
|---|
| 张大勇等.J-213快速固化厌氧胶的研究.《粘接》.2005,第26卷(第1期),1-3. * |
| 林可君.厌氧胶粘剂.《黎明化工》.1985,(第04期),31-36. * |
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