CN100543097C - A kind of have low dismounting force moment fire resistant anaerobic adhesive and preparation method thereof - Google Patents
A kind of have low dismounting force moment fire resistant anaerobic adhesive and preparation method thereof Download PDFInfo
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- CN100543097C CN100543097C CNB2007100722718A CN200710072271A CN100543097C CN 100543097 C CN100543097 C CN 100543097C CN B2007100722718 A CNB2007100722718 A CN B2007100722718A CN 200710072271 A CN200710072271 A CN 200710072271A CN 100543097 C CN100543097 C CN 100543097C
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Abstract
A kind of have low dismounting force moment fire resistant anaerobic adhesive and preparation method thereof, and it relates to a kind of anaerobic glue and preparation method thereof.It is poor to the invention solves existing fire resistant anaerobic adhesive serviceability, and adhering part dismounting difficulty is in the nothing, the problem of low strength product.Product of the present invention is made as follows: a. is stirred to dissolving fully with methacrylic acid diester monomer and stablizer; B. add promotor and adjacent benzenesulfonimide and be stirred to dissolving fully; C. add heat-resisting additive, high temperature resistant torque adjusting agent and aerosil, after treating to dissolve fully, be cooled to room temperature; D. adding organo-peroxide again stirs.Product of the present invention is easy to dismounting when parts for maintenance, intensity is adjustable, and this anaerobic glue does not have influence to heat resistance simultaneously, has guaranteed the high temperature breakdown torque of anaerobic glue.The present invention has overcome in the past the difficult dismounting of fire resistant anaerobic adhesive and detachable anaerobic adhesive high temperature breakdown torque is low, the shortcoming of temperature tolerance difference, and it is low also to have a cost, the characteristics of high efficiency.
Description
Technical field
The present invention relates to a kind of anaerobic glue and preparation method thereof.
Background technology
Present practical fire resistant anaerobic adhesive product category is a lot, but because fire resistant anaerobic adhesive monomer molecule chain presents rigidity, and intermolecular cross-linking density is big behind the hot setting, so commercially available fire resistant anaerobic adhesive generally all is high-intensity anaerobic glue, bonding test specimen is the dismounting difficulty when maintenance.
The factor that influences screw element and Flange Plane dismounting intensity has a lot as diameter of screw, length and tolerance clearance etc., but mainly is the character of tackiness agent.Estimate tackiness agent dismounting complexity main reference wracking moment/dismounting force moment (T at present
b/ T
p) ratio.When being used for permanent locking and not needing to dismantle, wish this value＜1, this is to be easy to reach in the anaerobic type locking glue prescription; When being used for detachable situation, require this ratio〉1, T
b/ T
pRatio big more, dismounting property is good more.1974, the famous in the world Loctite.Co of anaerobic glue company delivered the patent of detachable anaerobic adhesive, and (US3794610) this patent adopts polyester plasticizer that the methacrylic acid diester is carried out modification, prepares T
b/ T
pRatio is greater than 1 anaerobic glue kind; At the end of the seventies, the someone adopts a small amount of Viscotrol C, and polycaprolactone etc. carry out moment modification (special public clear 60-50202) to anaerobic glue; Since the eighties, ESCHEMINC has delivered the patent (US4569977) of unsaturated polyester modified anaerobic glue; Japanese a company in 1985 delivers patent (US4510270) and adopts Tripyrophosphoric acid modified methacrylic acid dibasic acid esters, can increase substantially wracking moment, reduces dismounting force moment.
These methods play effect preferably to use temperature for the detachable performance of-55～150 ℃ anaerobic glue, but do not fit into the preparation of the fire resistant anaerobic adhesive of use temperature more than 150 ℃, because the heat-resisting deficiency of these torque adjusting agent, have a strong impact on the resistance toheat of anaerobic glue after the adding, particularly the reduction of high temperature wracking moment is bigger, has destroyed the thermotolerance of anaerobic glue.The fire resistant anaerobic adhesive product that does not also have low dismounting force moment in the market.
Summary of the invention
It is poor to the objective of the invention is in order to solve existing fire resistant anaerobic adhesive serviceability, and adhering part dismounting difficulty is in the nothing, the problem of low strength product; And provide a kind of low dismounting force moment fire resistant anaerobic adhesive and preparation method thereof that has.The present invention is a kind of in order to reduce existing fire resistant anaerobic adhesive dismounting force moment, makes wracking moment/dismounting force moment (T of fire resistant anaerobic adhesive
b/ T
p) ratio 1, do not reduce simultaneously the method for the resistance toheat of anaerobic glue and the dismounting and the maintenance of convenient bonding test specimen again.Of the present invention have the low dismounting force moment fire resistant anaerobic adhesive by weight by 50～95 parts of methacrylic acid diester monomers, 10～40 parts of heat-resisting additives, 0.1～5 part of promotor, 0.1～5 part of adjacent benzenesulfonimide, 0.01～2 part of stablizer, 5～40 parts of high temperature resistant torque adjusting agent, 0.1～5 part of aerosil and organo-peroxide are made for 1～10 part, heat-resisting additive is selected bismaleimides for use, triallyl isocyanide urea ester, cyanate resin or polyimide, molybdenumdisulphide is selected in high temperature resistant torque adjusting agent for use, graphite, talcum powder, end epoxy group(ing) silicone oil, end hydroxypropyl silicone oil, end hydroxyethyl silicone oil or vinyl-terminated silicone fluid.
Above-mentioned methacrylic acid diester monomer is selected glycolmethacrylate, multicondensed ethylene glycol double methyl methacrylate, ethoxyquin dihydroxyphenyl propane dimethyl allene acid diester, the many acrylate of many hydroxymethyl phenols, polyurethane-type methacrylic ester, the methacrylic ester that contains allyloxy benzene or multiple epoxy acrylate monomer for use.
Heat-resisting additive has the stable on heating effect of the anaerobic glue of raising.
Promotor is selected pyrodin or benzoyl hydrazine for use, also can select N for use, N-dimethyl-p-toluidine, N, N-diethyl-p-tlouidine or triethylamine.
Stablizer is selected oxalic acid, ethylenediamine tetraacetic acid (EDTA), o-aminophenol, oxine, dihydroxy-benzene, benzoquinones, naphthoquinones or anthraquinone stopper for use.
High temperature resistant torque adjusting agent is to be used for regulating the wracking moment of anaerobic glue and the ratio of dismounting force moment, makes it greater than 1, selects for use heat-resisting and to have the pressed powder or the liquid silicone oil effect of lubricating quality better.
Organo-peroxide is selected isopropyl benzene hydroperoxide, tertbutyl peroxide, benzoyl peroxide or methyl ethyl ketone peroxide for use.
Preparation method with low dismounting force moment fire resistant anaerobic adhesive of the present invention is realized by the following step: a, get the stablizer of 50～95 parts methacrylic acid diester monomer and 0.01～2 part earlier under 45～55 ℃ by weight, stirred 30～120 minutes with 100～600r/min speed, reactant is dissolved fully; The adjacent benzenesulfonimide of b, the promotor of adding 0.1～5 weight part in the mixture that step a obtains and 0.1～5 weight part is stirred to dissolving fully; The high temperature resistant torque adjusting agent of c, the heat-resisting additive that adds 10～40 weight parts in the mixture that step b obtains, 5～40 weight parts and the aerosil of 0.1～5 weight part after treating to dissolve fully, are cooled to room temperature; D, the organo-peroxide that adds 1～10 weight part again in the mixture that step c obtains stir, and promptly are prepared into the low dismounting force moment fire resistant anaerobic adhesive.
By the consumption and the kind of regulating high temperature resistant torque adjusting agent, the wracking moment of anaerobic glue and dismounting force moment are descended, less to the wracking moment influence, dismounting force moment reduces greatly, makes the ratio (T of wracking moment and dismounting force moment
b/ T
p) greater than 1, in producing, low intensive fire resistant anaerobic adhesive, and the thermotolerance of anaerobic glue there is not influence.
Low dismounting force moment fire resistant anaerobic adhesive of the present invention is easy to dismounting when parts for maintenance, intensity is adjustable, and this anaerobic glue does not have influence to heat resistance simultaneously, has guaranteed the high temperature breakdown torque of anaerobic glue.The present invention has overcome in the past the difficult dismounting of fire resistant anaerobic adhesive and detachable anaerobic adhesive high temperature breakdown torque is low, the shortcoming of temperature tolerance difference, and it is low also to have a cost, the characteristics of high efficiency.
Embodiment
Embodiment one: have the low dismounting force moment fire resistant anaerobic adhesive in the present embodiment and make for 1～10 part by 50～95 parts of methacrylic acid diester monomers, 10～40 parts of heat-resisting additives, 0.1～5 part of promotor, 0.1～5 part of adjacent benzenesulfonimide, 0.01～2 part of stablizer, 5～40 parts of high temperature resistant torque adjusting agent, 0.1～5 part of aerosil and organo-peroxide by weight.
Embodiment two: the low dismounting force moment fire resistant anaerobic adhesive is made for 2～8 parts by 60～80 parts of methacrylic acid diester monomers, 15～30 parts of heat-resisting additives, 2～4 parts of promotor, 1～3 part of adjacent benzenesulfonimide, 0.1～1 part of stablizer, 10～35 parts of high temperature resistant torque adjusting agent, 1～4 part of aerosil and organo-peroxide by weight in the present embodiment.
Embodiment three: the low dismounting force moment fire resistant anaerobic adhesive is made for 6 parts by 70 parts of methacrylic acid diester monomers, 20 parts of heat-resisting additives, 3 parts of promotor, 3 parts of adjacent benzenesulfonimides, 1 part of stablizer, 20 parts of high temperature resistant torque adjusting agent, 3 parts of aerosils and organo-peroxide by weight in the present embodiment.
Embodiment four: what present embodiment and embodiment one to three were different is that methacrylic acid diester monomer is a glycolmethacrylate, triethylene glycolbismethyl-acrylate, the tetraethylene-glycol dimethacrylate, polyethylene glycol dimethacrylate, ethoxyquin dihydroxyphenyl propane dimethyl allene acid diester, trimethylolpropane trimethacrylate, Rocryl 410, trishydroxymethyl phenol triacrylate, isocyanate terminated basic polyethylene glycol dimethacrylate, 4-allyloxy phenylethyl alcohol methacrylic ester, 4-allyloxy phenylcarbinol methacrylic ester or bisphenol-A epoxy diacrylate.Other is identical with embodiment one to three.
Embodiment five: what present embodiment and embodiment one to three were different is that heat-resisting additive is bismaleimides, triallyl isocyanide urea ester, cyanate resin, end ethynyl polyimide, phenylacetylene-capped polyimide or ethene end group polyimide.Other is identical with embodiment one to three.
Heat-resisting additive has the stable on heating effect of the anaerobic glue of raising in the present embodiment.
Embodiment six: promotor is pyrodin or benzoyl hydrazine in the present embodiment.Other is identical with embodiment one to three.
Embodiment seven: what present embodiment and embodiment one to three were different is that promotor is N, N-dimethyl-p-toluidine, N, N-diethyl-p-tlouidine or triethylamine.Other is identical with embodiment one to three.
Embodiment eight: what present embodiment and embodiment one to three were different is that stablizer is selected oxalic acid, ethylenediamine tetraacetic acid (EDTA), o-aminophenol or oxine for use.Other is identical with embodiment one to three.
Embodiment nine: what present embodiment and embodiment one to three were different is that stablizer is dihydroxy-benzene, benzoquinones, naphthoquinones or anthraquinone.Other is identical with embodiment one to three.
Embodiment ten: what present embodiment and embodiment one to three were different is that molybdenumdisulphide, graphite, talcum powder, end hydroxyl silicone oil, end epoxy group(ing) silicone oil, end hydroxypropyl silicone oil, end hydroxyethyl silicone oil or vinyl-terminated silicone fluid are selected in high temperature resistant torque adjusting agent for use.Other is identical with embodiment one to three.
High temperature resistant torque adjusting agent in the present embodiment is to be used for regulating the wracking moment of anaerobic glue and the ratio of dismounting force moment, makes it greater than 1, selects for use heat-resisting and to have the pressed powder or the liquid silicone oil effect of lubricating quality better.
Embodiment 11: what present embodiment and embodiment one to three were different is that organo-peroxide is selected isopropyl benzene hydroperoxide, tertbutyl peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, cumene peroxide or tert-butyl peroxide for use.Other is identical with embodiment one to three.
Embodiment 12: present embodiment provides a kind of preparation method with low dismounting force moment fire resistant anaerobic adhesive, this method is realized by the following step: a, get the stablizer of 50～95 parts methacrylic acid diester monomer and 0.01～2 part earlier under 45～55 ℃ by weight, stirred 30～120 minutes with 100～600r/min speed, reactant is dissolved fully; The adjacent benzenesulfonimide of b, the promotor of adding 0.1～5 weight part in step a and 0.1～5 weight part is stirred to dissolving fully; The high temperature resistant torque adjusting agent of c, the heat-resisting additive that adds 10～50 weight parts in step b, 5～40 weight parts and the aerosil of 0.1～5 weight part after treating to dissolve fully, are cooled to room temperature; D, the organo-peroxide that adds 1～10 weight part again in step c stir, and promptly are prepared into the low dismounting force moment fire resistant anaerobic adhesive.
Embodiment 13: preparation method's the step that present embodiment has the low dismounting force moment fire resistant anaerobic adhesive is as follows: get by weight in the ethoxyquin dihydroxyphenyl propane dimethyl allene acid diester that 0.02 part oxalic acid joins 60 parts and stir, be warming up to 45 ℃ and make its dissolving, adding 1 part pyrodin and 1.5 parts adjacent benzenesulfonimide again is stirred to molten entirely, and then add 10 parts N, N '-4,4 '-diphenyl methane dimaleimide and 10 parts high temperature resistant torque adjusting agent and 2 parts silicon-dioxide, make its postcooling that is uniformly dispersed to room temperature, the isopropyl benzene hydroperoxide that adds 5 parts at last again stirs; Obtain product.
Adopt the method for present embodiment, add different high temperature resistant torque adjusting agent and detect, draw to draw a conclusion by HB5315-93 and HB5319-93 standard:
Table 1
Table 2
Table 1 is a hot strength table of dosing the fire resistant anaerobic adhesive of the different torque adjusting agent of 10 weight parts, T in the table
bBe breakdown torque, T
pBe removal torque; Table 2 is above-mentioned anaerobic glue high temperature ageing intensity tables after 2 hours.
In fire resistant anaerobic adhesive, add 10 weight part powdered graphites, molybdenumdisulphide or end hydroxypropyl silicone oil as can be seen from Table 1 under the differing temps, its breakdown torque there is not too big influence, and removal torque reduces greatly, makes bonding test specimen both have bonding reliability, again dismounting easily; After dosing 10 parts of Viscotrol C, breakdown torque and removal torque all reduce, and removal torque is bigger than breakdown torque decline scope, makes T
b/ T
p1, but because T
bDescend, so reduced the reliability of bonding test specimen.Because after fixing takes place the heat-resisting additive in the fire resistant anaerobic adhesive at a certain temperature, so bonding strength can further raise, bonding test specimen is more difficult dismounting after heat as can be seen from Table 2.If in fire resistant anaerobic adhesive, add 10 weight part powdered graphites, molybdenumdisulphide or end hydroxypropyl silicone oil, its breakdown torque there is not too big influence and removal torque reduces greatly, bonding test specimen is dismantled easily; Change into and bonding strength is descended to some extent after dosing 10 parts of Viscotrol C, but T
b/ T
p＜1, still difficult dismounting.
Embodiment 14: preparation method's the step that present embodiment has the low dismounting force moment fire resistant anaerobic adhesive is as follows: get by weight in the ethoxyquin dihydroxyphenyl propane dimethyl allene acid diester that 0.02 part oxalic acid joins 80 parts and stir, be warming up to 50 ℃ and make its dissolving, adding 1.5 parts pyrodin and 2.0 parts adjacent benzenesulfonimide again is stirred to molten entirely, and then add 20 parts N, N '-4,4 '-diphenyl methane dimaleimide and 25 parts powdered graphite and 2 parts silicon-dioxide, make its postcooling that is uniformly dispersed to room temperature, the isopropyl benzene hydroperoxide that adds 8 parts at last again stirs; Obtain product.
Detect the product of present embodiment by HB5315-93 and HB5319-93 standard, draw to draw a conclusion:
Table 3
Table 4
Table 3 is hot strength tables of above-mentioned anaerobic glue and commercially available fire resistant anaerobic adhesive Loctite 272, T in the table
bBe breakdown torque, T
pBe removal torque; Table 4 is the intensity tables of above two kinds of anaerobic glue high temperature ageings after 2 hours.
Add the powdered graphite of 25 weight parts as can be seen from Table 3 under the differing temps in fire resistant anaerobic adhesive, can reduce the intensity of fire resistant anaerobic adhesive, breakdown torque descends less, and removal torque reduces greatly, T
b/ T
p1, and the resistance toheat of fire resistant anaerobic adhesive do not had influence, the high temperature breakdown torque in the time of 250 ℃ still is not less than 50% of room temperature breakdown torque.The anaerobic glue of producing in this way be in, the low strength fire resistant anaerobic adhesive.If in fire resistant anaerobic adhesive, add the powdered graphite of 25 weight parts, can reduce the bonding strength of fire resistant anaerobic adhesive, T as can be seen from Table 4
b/ T
p1, in producing, the low strength fire resistant anaerobic adhesive, bonding test specimen is dismantled easily.And dismounting intensity is higher behind the present commercially available fire resistant anaerobic adhesive Loctite272 high temperature ageing, is difficult to dismounting.
Claims (8)
1, a kind of have a low dismounting force moment fire resistant anaerobic adhesive, it is characterized in that it is made for 1～10 part by 50～95 parts of methacrylic acid diester monomers, 10～40 parts of heat-resisting additives, 0.1～5 part of promotor, 0.1～5 part of adjacent benzenesulfonimide, 0.01～2 part of stablizer, 5～40 parts of high temperature resistant torque adjusting agent, 0.1～5 part of aerosil and organo-peroxide by weight; Heat-resisting additive is bismaleimides, triallyl isocyanide urea ester, cyanate resin or polyimide, and molybdenumdisulphide, graphite, talcum powder, end epoxy group(ing) silicone oil, end hydroxypropyl silicone oil, end hydroxyethyl silicone oil or vinyl-terminated silicone fluid are selected in high temperature resistant torque adjusting agent for use.
2, a kind of low dismounting force moment fire resistant anaerobic adhesive that has according to claim 1 is characterized in that it is made for 2～8 parts by 60～80 parts of methacrylic acid diester monomers, 15～30 parts of heat-resisting additives, 2～4 parts of promotor, 1～3 part of adjacent benzenesulfonimide, 0.1～1 part of stablizer, 10～35 parts of high temperature resistant torque adjusting agent, 1～4 part of aerosil and organo-peroxide by weight.
3, a kind of low dismounting force moment fire resistant anaerobic adhesive that has according to claim 1 is characterized in that it is made for 6 parts by 70 parts of methacrylic acid diester monomers, 20 parts of heat-resisting additives, 3 parts of promotor, 3 parts of adjacent benzenesulfonimides, 1 part of stablizer, 20 parts of high temperature resistant torque adjusting agent, 3 parts of aerosils and organo-peroxide by weight.
4,, it is characterized in that methacrylic acid diester monomer is glycolmethacrylate, multicondensed ethylene glycol double methyl methacrylate, ethoxyquin dihydroxyphenyl propane dimethyl allene acid diester, the many acrylate of many hydroxymethyl phenols, polyurethane-type methacrylic ester or the methacrylic ester that contains allyloxy benzene according to claim 1,2 or 3 described a kind of low dismounting force moment fire resistant anaerobic adhesives that have.
5, according to claim 1,2 or 3 described a kind of low dismounting force moment fire resistant anaerobic adhesives that have, it is characterized in that promotor is pyrodin, benzoyl hydrazine, N, N-dimethyl-p-toluidine, N, N-diethyl-p-tlouidine or triethylamine.
6, according to claim 1,2 or 3 described a kind of low dismounting force moment fire resistant anaerobic adhesives that have, it is characterized in that stablizer is oxalic acid, ethylenediamine tetraacetic acid (EDTA), o-aminophenol, oxine, dihydroxy-benzene, benzoquinones, naphthoquinones or anthraquinone stopper.
7,, it is characterized in that organo-peroxide selects isopropyl benzene hydroperoxide, tertbutyl peroxide, benzoyl peroxide or methyl ethyl ketone peroxide for use according to claim 1,2 or 3 described a kind of low dismounting force moment fire resistant anaerobic adhesives that have.
8, a kind of preparation method as claimed in claim 1 with low dismounting force moment fire resistant anaerobic adhesive, it is characterized in that this method steps is as follows: a, get the stablizer of 50～95 parts methacrylic acid diester monomer and 0.01～2 part earlier under 45～55 ℃ by weight, stirred 30～120 minutes with 100～600r/min speed, reactant is dissolved fully; The adjacent benzenesulfonimide of b, the promotor of adding 0.1～5 weight part in the mixture that step a obtains and 0.1～5 weight part is stirred to dissolving fully; The high temperature resistant torque adjusting agent of c, the heat-resisting additive that adds 10～40 weight parts in the mixture that step b obtains, 5～40 weight parts and the aerosil of 0.1～5 weight part after treating to dissolve fully, are cooled to room temperature; D, the organo-peroxide that adds 1～10 weight part again in the mixture that step c obtains stir, and promptly are prepared into the low dismounting force moment fire resistant anaerobic adhesive.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101497769B (en) * | 2009-02-23 | 2010-11-24 | 黑龙江省科学院石油化学研究院 | Inorganic / organic hybridized high temperature resistant anaerobic type screw thread locking sealing adhesive and preparation thereof |
| RU2013156967A (en) | 2011-05-24 | 2015-06-27 | Эвоник Рем ГмбХ | REACTIVE RESINS FOR CABLE COMPOUNDS |
| CN102516891B (en) * | 2011-12-14 | 2014-01-08 | 湖北回天胶业股份有限公司 | Single-component anaerobic adhesive with high filing gap and preparation method thereof |
| CN102876264A (en) * | 2012-09-25 | 2013-01-16 | 苏州汾湖电梯有限公司 | Anaerobic adhesive with high breakaway torque |
| CN103614084B (en) * | 2013-10-28 | 2015-12-09 | 北京天山新材料技术有限公司 | A kind of high temperature resistant precoating type anaerobic glue and preparation method thereof |
| CN104650745A (en) * | 2014-06-12 | 2015-05-27 | 徐饶春 | Anaerobic adhesive and preparation method thereof |
| CN104152086B (en) * | 2014-08-08 | 2017-01-18 | 黑龙江省科学院石油化学研究院 | Modified acrylate high temperature-resistant anaerobic adhesive and preparation method thereof |
| CN104356963A (en) * | 2014-11-19 | 2015-02-18 | 南京艾布纳密封技术有限公司 | High-temperature resistant thread-locking anaerobic adhesive and preparation method thereof |
| CN105176420B (en) * | 2015-10-13 | 2018-07-20 | 广东三和化工科技有限公司 | A kind of flat sealing anaerbic adhesive and preparation method thereof |
| GB2543756B (en) * | 2015-10-22 | 2017-10-18 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
| CN105713542B (en) * | 2016-04-29 | 2017-09-15 | 黑龙江省科学院石油化学研究院 | A kind of Acrylic Adhesive Modified with Silicone and preparation method thereof |
| CN105885706B (en) * | 2016-06-24 | 2019-01-15 | 黑龙江省科学院石油化学研究院 | Silicon oil modified silicon hybridization anaerobic adhesive and preparation method thereof |
| GB2567242B (en) * | 2017-10-09 | 2021-08-11 | Henkel IP & Holding GmbH | Anaerobically curable compositions comprising 1, 2, 3, 4-tetrahydro benzo(h)quinolin-3-ol or derivatives thereof |
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