CN102516891A - Single-component anaerobic adhesive with high filing gap and preparation method thereof - Google Patents
Single-component anaerobic adhesive with high filing gap and preparation method thereof Download PDFInfo
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- CN102516891A CN102516891A CN2011104169848A CN201110416984A CN102516891A CN 102516891 A CN102516891 A CN 102516891A CN 2011104169848 A CN2011104169848 A CN 2011104169848A CN 201110416984 A CN201110416984 A CN 201110416984A CN 102516891 A CN102516891 A CN 102516891A
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Abstract
The invention relates to a single-component anaerobic adhesive with high filing gap and a preparation method thereof, and belongs to the technical field of anaerobic adhesives. Due to the great influence of gap on the curing of a present anaerobic adhesive, its curing effect is very poor when the gap exceeds 0.5mm and even the present anaerobic adhesive can not be cured. The above problem of the present anaerobic adhesive is solved in the invention. The anaerobic adhesive provided by the invention is mainly characterized by comprising: (A) 50-98 wt% of a terminated unsaturated monomer containing at least one vinyl with the molecular weight being less than 600; (B) 0-30 wt% of a plasticizer; (C) 0-20 wt% of a powder; (D) 0.02-1 wt% of a polymerization inhibitor; (E) 1-3 wt% of N-acetylphenylhydrazine; (F) 0.5-5 wt% of benzoyl sulfonic imide; (G) 0.01-0.1% of a metal ion chelating agent; (H) 0.1-5% of a peroxide initiator; and (I) 0-20% of fumed silica. The filling gap in the invention can reach more than 5mm. The anaerobic adhesive has excellent storage stability. Failure moment and average dismounting moment can be adjusted within 0.1-30N.m. sealing performance can reach 1MPa (air pressure) without leakage. Static shearing strength can reach more than 25 MPa. The invention mainly provides the single-component anaerobic adhesive with high filing gap and the preparation method thereof.
Description
Technical field
The invention belongs to the anaerobic glue technical field, be specifically related to the high gap anaerobic glue of filling of a kind of single-component, anaerobically curable is widely used in thread locking, pipe thread seal, flat seal, the part fixing of industries such as automobile, engineering machinery, electronic apparatus.
Background technology
As everyone knows, the curing of anaerobic glue receives the influence in gap very big, if generally speaking the gap surpasses 0.5mm, the solidification effect of anaerobic glue is very poor, even can't solidify at all, and also this shortcoming makes the application of anaerobic glue receive very big restriction just.Use anaerobic glue to lock or when sealing, its effect is often relatively poor like the bigger coarse thread bolt of diameter or pipe-thread, it is locking to use other fastening means to carry out; Some flange, head side have deep trouth and cause the gap to surpass 1mm, and the anaerobism flat sealant can't solidify, and can't form sealing effectively, have to select for use rubber sheet gasket; Though also can improve this problem sometimes through the primary coat of spary anaerobic glue promotor, be to use primary coat both to increase operation, also increased cost, can't embody the advantage of anaerobic glue.
In sum, it is very necessary to develop the high gap anaerobic glue of filling of a kind of single-component.
Summary of the invention
The purpose that the present invention relates to is exactly the high gap anaerobic glue of filling of a kind of single-component that proposes to anaerobic glue weak point set forth above.
Further purpose of the present invention provides a kind of high method of filling the gap anaerobic glue of above-mentioned single-component for preparing.
The technical solution of single-component anaerobic structure glue of the present invention is: the high gap anaerobic glue of filling of a kind of single-component, and it is characterized in that: its composition comprises:
(A) 50 ~ 98%Wt molecular weight is less than 600 the unsaturated monomer that contains 1 ethenyl blocking at least, and described molecular weight is a molecular weight less than 600 mono acrylic ester monomer, molecular weight less than 600 monomethacrylates monomer, molecular weight less than 600 dimethacrylate monomer, molecular weight less than the end capped polyurethane oligomer of 600 methacrylate monomers or its mixture less than 600 the unsaturated monomer that contains 1 ethenyl blocking at least;
(B) 0 ~ 30%Wt softening agent, described softening agent are Viscotrol C, oleic acid, bialkyl ortho phthalate, phenyl alkylsulfonate, paraffin, polyoxyethylene glycol 2-ethylhexoate, polyethylene glycol (PEG) oleate, polyoxyethylene glycol lauryl, adipate polyester or its mixture;
(C) 0 ~ 20% Wt powder, described powder are Vilaterm powder, polypropylene powder, SE powder, polytetrafluoroethylene powder, polyvinyl butyral powder, castor oil derivative, SEPIGEL 305 powder, Paris white, mica powder, zeyssatite, organobentonite, white titanium pigment or its mixture;
(D) 0.02% ~ 1%Wt stopper;
(E) 1 ~ 3%Wt N-pyrodin;
(F) 0.5 ~ 5%Wt benzoic sulfimide;
(G) 0.01% ~ 0.1% metal ion chelation agent;
(H) 0.1 ~ 5% peroxide initiator;
(I) 0 ~ 20% aerosil.
Said N-pyrodin and benzoic sulfimide are promotor in the technical solution of the present invention; The two must just might be able to reach high purpose of filling the gap with described ratio coupling; Use any one all not reach this purpose separately, being replaced with other promotor also not necessarily has this effect.
Said stopper is 1 in the technical solution of the present invention, 4-naphthoquinones, Resorcinol, MEHQ or its mixture.
Said metal ion chelation agent is EDTA and EDTA sodium salt or its mixture in the technical solution of the present invention.
Said peroxide initiator is organic hydroperoxide class, peroxo-ketone, dialkyl peroxide class, peracid ester class and acyl peroxide in the technical solution of the present invention.
The said high method of filling the gap anaerobic glue of single-component for preparing in the technical solution of the present invention is characterized in that may further comprise the steps:
1) (A) 50 ~ 98%Wt molecular weight is added the glue container respectively less than the unsaturated monomer that contains 1 ethenyl blocking at least, (B) 0 ~ 30%Wt softening agent, (D) 0.02% ~ 1%Wt stopper, (E) 1 ~ 3%Wt N-pyrodin, (F) benzoic sulfimide of 600; Stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) in the glue container, add (C) 0 ~ 20% Wt powder, (G) 0.01% ~ 0.1% metal ion chelation agent, stir 30mim ~ 90min down, be uniformly dispersed to powder at 5 ℃～35 ℃;
3) in the glue container, add (H) 0.1 ~ 5% peroxide initiator, (I) 0 ~ 20% aerosil, stir 20mim ~ 30min down at 5 ℃～35 ℃, to being uniformly dispersed;
4) if the more vacuum-pumping 5min of bubble removes the middle bubble that removes photoresist, vacuum pressure is controlled at-0.09 ~-0.07MPa between;
5) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Adopting the high filling of the single-component gap anaerobic glue of the inventive method preparation is a kind of viscous liquid or paste; Be stored in the dark vinyon bottle (pipe); Before using, this anaerobic structure glue do not need allotment; Versatility is good, can be used for thread locking, pipe thread seal, flat seal and part fixing etc. in the industry product assembling process such as automobile, electrical equipment, machinery.
The high gap anaerobic glue of filling of single-component of the present invention, wherein the first step churning time is controlled at 30～60min among the preparation technology, after stirring, can carry out the operation of second step, and temperature is controlled at 5 ℃～25 ℃.After stirring, discharging, glue is kept in the dark vinyon bottle (pipe) for use.
The high gap anaerobic glue of filling of single-component of the present invention under the room temperature condition, is in a liquid state or paste; Just the time fills the gap and can reach more than the 5mm about 10min admittedly, package stability excellent (80 ℃ * 2h is gel not); In the vinyon bottle (pipe) of dark color, can preserve more than 2 years under the normal temperature; Wracking moment can be as required respectively in 0.1 ~ 30N.m adjustment with average dismounting force moment, and it is air tight that sealing property can reach 1MPa (air pressure), and quiet shearing resistance can reach more than 25 MPa.
The present invention mainly provides the high gap anaerobic glue and preparation method thereof of filling of a kind of single-component.
Description of drawings
Fig. 1 is that the present invention fills clearance test instrument synoptic diagram.
Embodiment
The following example and comparative example will be introduced the present invention more in detail, but the present invention is not limited to this.
Embodiment 1:
Proportioning
Macrogol 200 dimethacrylate (molecular weight 336) 96.26%Wt
1,4-naphthoquinones 0.02%Wt
N-pyrodin 1.7%Wt
Benzoic sulfimide 0.5%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.5%Wt
The preparation method:
1) in container, add polyoxyethylene glycol 200 dimethacrylates, 1,4-naphthoquinones, N-pyrodin, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add the EDTA tetra-na salt, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide and stir 20mim ~ 30min down to even at 5 ℃～35 ℃;
4) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test:
1, stability: single-component anaerobic structure glue is put into 80 ℃ of baking ovens heat, measure the time that gel occurs.
2, curing speed: test according to HB5325-85.
3, wracking moment and average dismounting force moment: test according to GB/T 18747.1-2002.
4, quiet shearing resistance: test according to HB5314-85.
5, thread seal performance: test according to HB5315-85.
6, viscosity: test according to GB/T 2794-1995.
7, fill gap d: use carbon steel sheet 2,3 by preparation wedge shape testing tool shown in Figure 1; Other sides seal with plastic plate; Anaerobic glue is filled between the anaerobic glue fill area 1 from a side, leave standstill the maximum cured thickness of test anaerobic glue behind the 24h, be the maximum gap d max that fills.
Test result is seen table 1.
Embodiment 2:
Proportioning:
PEG 400 dimethacrylate (molecular weight 536) 91.43%Wt
1,4-naphthoquinones 0.05%Wt
N-pyrodin 1.50%Wt
Benzoic sulfimide 3.00%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 2.00%Wt
Aerosil 2.00%Wt
The preparation method:
1) in container, add polyoxyethylene glycol 400 dimethacrylates, 1,4-naphthoquinones, N-pyrodin, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add the EDTA tetra-na salt, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide, aerosil and under 5 ℃～35 ℃, stir 20mim ~ 30min to even;
4) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Embodiment 3:
Proportioning:
Tri Ethyleneglycol dimethacrylate (molecular weight 286) 80.45%Wt
Rocryl 400 15%Wt
1,4-naphthoquinones 0.03%Wt
N-pyrodin 1.00%Wt
Benzoic sulfimide 2.00%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.50%Wt
The preparation method:
1) in container, add Tri Ethyleneglycol dimethacrylate, Rocryl 400,1,4-naphthoquinones, N-pyrodin, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add the EDTA tetra-na salt, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide and stir 20mim ~ 30min down to even at 5 ℃～35 ℃;
4) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Embodiment 4:
Proportioning:
Macrogol 200 dimethacrylate (molecular weight 336) 82.45%Wt
Polytetrafluoroethylene powder 4.00%Wt
Polyvinyl butyral acetal 4.00%Wt
1,4-naphthoquinones 0.03%Wt
N-pyrodin 1.00%Wt
Benzoic sulfimide 3.00%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.50%Wt
Aerosil 4.00%Wt
The preparation method:
1) in container, add Tri Ethyleneglycol dimethacrylate, Rocryl 400,1,4-naphthoquinones, N-pyrodin, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add EDTA tetra-na salt, polytetrafluoroethylene powder, polyvinyl butyral acetal, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide, aerosil and under 5 ℃～35 ℃, stir 20mim ~ 30min to even;
4) vacuumize the 5min deaeration, vacuum pressure is controlled at-0.09 ~-0.07MPa between;
5) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Embodiment 5:
Proportioning:
Rocryl 400 (molecular weight 130) 77.25%Wt
Vilaterm powder 10.00%Wt
1,4-naphthoquinones 0.03%Wt
N-pyrodin 1.70%Wt
Benzoic sulfimide 1.00%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.50%Wt
Aerosil 7.00%Wt
The preparation method:
1) methylate Hydroxyethyl acrylate, 1 in container, 4-naphthoquinones, N-pyrodin, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add EDTA tetra-na salt, Vilaterm powder, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide, aerosil and under 5 ℃～35 ℃, stir 20mim ~ 30min to even;
4) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Embodiment 6:
Proportioning:
Macrogol 200 dimethacrylate (molecular weight 336) 50.00%Wt
The two 2-ethylhexoate 25.65%Wt of Macrogol 200
Vilaterm powder 8.50%Wt
Polyvinyl butyral acetal 6.20%Wt
1,4-naphthoquinones 0.03%Wt
N-pyrodin 1.20%Wt
Benzoic sulfimide 2.80%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 2.00%Wt
Aerosil 3.60%Wt
The preparation method:
1) in container, add the two 2-ethylhexoates, 1 of Tri Ethyleneglycol dimethacrylate, Macrogol 200,4-naphthoquinones, N-pyrodin, benzoic sulfimide stir 30mim ~ 90min down at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add EDTA tetra-na salt, Vilaterm powder, polyvinyl butyral acetal, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide, aerosil and under 5 ℃～35 ℃, stir 20mim ~ 30min to even;
4) vacuumize the 5min deaeration, vacuum pressure is controlled at-0.09 ~-0.07MPa between;
5) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Comparative example 1
Proportioning
Macrogol 200 dimethacrylate 94.46%Wt
1,4-naphthoquinones 0.02%Wt
Benzoic sulfimide 4.00%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.50%Wt
The preparation method:
1) in container, add polyoxyethylene glycol 200 dimethacrylates, 1,4-naphthoquinones, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add the EDTA tetra-na salt, stir 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide and stir 20mim ~ 30min down to even at 5 ℃～35 ℃;
4) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Comparative example 2
Proportioning
Macrogol 200 dimethacrylate 94.46%Wt
1,4-naphthoquinones 0.02%Wt
Benzoic sulfimide 4.00%Wt
N, N-dimethyl-Ortho Toluidine 1.00%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.50%Wt
The preparation method:
1) in container, add polyoxyethylene glycol 200 dimethacrylates, 1,4-naphthoquinones, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add EDTA tetra-na salt, N, N-dimethyl-Ortho Toluidine stirs 30mim ~ 90min down to even at 5 ℃～35 ℃;
3) add isopropyl benzene hydroperoxide and stir 20mim ~ 30min down to even at 5 ℃～35 ℃;
4) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Comparative example 3
Proportioning:
Ethoxyquin (10) bisphenol a dimethacrylate (molecular weight 804) 85.56%Wt
Vilaterm powder 3.50%Wt
Polyvinyl butyral acetal 4.20%Wt
1,4-naphthoquinones 0.03%Wt
N-pyrodin 1.20%Wt
Benzoic sulfimide 0.80%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.00%Wt
Aerosil 3.60%Wt
The preparation method:
1) in container, add ethoxyquin (10) bisphenol a dimethacrylate, 1,4-naphthoquinones, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add EDTA tetra-na salt, Vilaterm powder, polyvinyl butyral acetal and under 5 ℃～35 ℃, stir 30mim ~ 90min to even;
3) add isopropyl benzene hydroperoxide, aerosil and under 5 ℃～35 ℃, stir 20mim ~ 30min to even;
4) vacuumize the 5min deaeration, vacuum pressure is controlled at-0.09 ~-0.07MPa between;
5) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Test result is seen table 1.
Comparative example 4
Proportioning:
The end capped polyurethane oligomer of methacrylate monomers (molecular weight about 4000) 96.25%Wt
1,4-naphthoquinones 0.03%Wt
N-pyrodin 1.20%Wt
Benzoic sulfimide 1.50%Wt
EDTA tetra-na salt 0.02%Wt
Isopropyl benzene hydroperoxide 1.00%Wt
The preparation method:
1) the end capped polyurethane oligomer of methylate acrylate monomer, 1 in container, 4-naphthoquinones, benzoic sulfimide stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) add EDTA tetra-na salt, Vilaterm powder, polyvinyl butyral acetal and under 5 ℃～35 ℃, stir 30mim ~ 90min to even;
3) add isopropyl benzene hydroperoxide, aerosil and under 5 ℃～35 ℃, stir 20mim ~ 30min to even;
4) vacuumize the 5min deaeration, vacuum pressure is controlled at-0.09 ~-0.07MPa between;
5) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
Performance test is with embodiment 1.
Claims (5)
1. a single-component height is filled the gap anaerobic glue, it is characterized in that its composition comprises:
(A) 50 ~ 98%Wt molecular weight is less than 600 the unsaturated monomer that contains 1 ethenyl blocking at least, and described molecular weight is a molecular weight less than 600 mono acrylic ester monomer, molecular weight less than 600 monomethacrylates monomer, molecular weight less than 600 dimethacrylate monomer, molecular weight less than the end capped polyurethane oligomer of 600 methacrylate monomers or its mixture less than 600 the unsaturated monomer that contains 1 ethenyl blocking at least;
(B) 0 ~ 30%Wt softening agent, described softening agent are Viscotrol C, oleic acid, bialkyl ortho phthalate, phenyl alkylsulfonate, paraffin, polyoxyethylene glycol 2-ethylhexoate, polyethylene glycol (PEG) oleate, polyoxyethylene glycol lauryl, adipate polyester or its mixture;
(C) 0 ~ 20% Wt powder, described powder are Vilaterm powder, polypropylene powder, SE powder, polytetrafluoroethylene powder, polyvinyl butyral powder, castor oil derivative, SEPIGEL 305 powder, Paris white, mica powder, zeyssatite, organobentonite, white titanium pigment or its mixture;
(D) 0.02% ~ 1%Wt stopper;
(E) 1 ~ 3%Wt N-pyrodin;
(F) 0.5 ~ 5%Wt benzoic sulfimide;
(G) 0.01% ~ 0.1% metal ion chelation agent;
(H) 0.1 ~ 5% peroxide initiator;
(I) 0 ~ 20% aerosil.
2. the high gap anaerobic glue of filling of single-component according to claim 1, it is characterized in that: described stopper is 1,4-naphthoquinones, Resorcinol, MEHQ or its mixture.
3. the high gap anaerobic glue of filling of single-component according to claim 1, it is characterized in that: described metal ion chelation agent is EDTA and EDTA sodium salt or its mixture.
4. the high gap anaerobic glue of filling of single-component according to claim 1, it is characterized in that: described peroxide initiator is organic hydroperoxide class, peroxo-ketone, dialkyl peroxide class, peracid ester class and acyl peroxide.
5. one kind prepares the high preparation method who fills the gap anaerobic glue of the described single-component of claim 1, it is characterized in that may further comprise the steps:
1) (A) 50 ~ 98%Wt molecular weight is added the glue container respectively less than the unsaturated monomer that contains 1 ethenyl blocking at least, (B) 0 ~ 30%Wt softening agent, (D) 0.02% ~ 1%Wt stopper, (E) 1 ~ 3%Wt N-pyrodin, (F) benzoic sulfimide of 600; Stir down 30mim ~ 90min at 5 ℃～35 ℃, dissolve fully evenly to solid materials;
2) in the glue container, add (C) 0 ~ 20% Wt powder, (G) 0.01% ~ 0.1% metal ion chelation agent, stir 30mim ~ 90min down, be uniformly dispersed to powder at 5 ℃～35 ℃;
3) in the glue container, add (H) 0.1 ~ 5% peroxide initiator, (I) 0 ~ 20% aerosil, stir 20mim ~ 30min down at 5 ℃～35 ℃, to being uniformly dispersed;
4) vacuumize and remove the middle bubble that removes photoresist, vacuum pressure is controlled at-0.09 ~-0.07MPa between;
5) discharging, can is kept in Dark Place in new LDPE (film grade) material packing, and is for use.
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| WO2014151358A2 (en) * | 2013-03-15 | 2014-09-25 | Henkel US IP LLC | Anaerobic curable compositions |
| CN104119805A (en) * | 2013-04-24 | 2014-10-29 | 烟台海泰化工科技有限公司 | Anaerobic adhesive for screw thread locking or pipe thread sealing |
| CN104327751A (en) * | 2014-11-19 | 2015-02-04 | 南京艾布纳密封技术有限公司 | Anaerobic adhesive with high oil resistance and preparation method of anaerobic adhesive |
| CN104694049A (en) * | 2013-12-04 | 2015-06-10 | 湖北回天新材料股份有限公司 | Flame-retardant water-resistant adhesive agent for cold-proof material and preparation method thereof |
| CN105255373A (en) * | 2015-11-17 | 2016-01-20 | 湖北回天新材料股份有限公司 | Lubrication-type pre-coating thread fastening sealant and preparing method thereof |
| CN105295747A (en) * | 2015-11-17 | 2016-02-03 | 湖北回天新材料股份有限公司 | Lubricating type threaded locking sealing anaerobic adhesive and preparation method |
| CN105295810A (en) * | 2015-11-26 | 2016-02-03 | 北京天山新材料技术有限公司 | Anaerobic pipe thread sealant and preparation method thereof |
| CN106700987A (en) * | 2017-01-18 | 2017-05-24 | 杭州得力科技股份有限公司 | Preparation method and product of high-temperature anaerobic adhesive |
| CN106752991A (en) * | 2017-01-18 | 2017-05-31 | 杭州得力科技股份有限公司 | The preparation method and product of a kind of UV curable acrylate adhesive |
| CN109054690A (en) * | 2018-07-20 | 2018-12-21 | 成都玉龙化工有限公司 | A kind of novel wood plank bonding agent and preparation method thereof |
| GB2585003A (en) * | 2019-06-21 | 2020-12-30 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
| WO2024046703A1 (en) * | 2022-09-01 | 2024-03-07 | Henkel Ag & Co. Kgaa | Anaerobically curable compositions |
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