CN109810665A - A kind of one-component acrylic acid anaerobic adhesive and preparation method thereof - Google Patents
A kind of one-component acrylic acid anaerobic adhesive and preparation method thereof Download PDFInfo
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- CN109810665A CN109810665A CN201811496366.7A CN201811496366A CN109810665A CN 109810665 A CN109810665 A CN 109810665A CN 201811496366 A CN201811496366 A CN 201811496366A CN 109810665 A CN109810665 A CN 109810665A
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- anaerobic glue
- methacrylate
- diisocyanate
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Abstract
The invention discloses a kind of one-component anaerobic glue, be grouped as by the group of following weight percent content: methacrylate monomers 55-70%, polyurethane acrylate prepolymer 25-40%, initiator 1-2%, promotor 0.1-2%, stabilizer 0.05-2%, polyurethane acrylate prepolymer are polymerized by the component of following weight percent content: diisocyanate 50-60%, dihydric alcohol 30-40%, methacrylic acid hydroxy ester 5-10%.The present invention in the presence of air will not crosslinking curing, and viscosity is held essentially constant within storage period, in ring winding process, completely cut off air, that is, cross-linkable solidifying, viscosity is small, has good wetability to polarization maintaining optical fibre, operation curing performance fully meets optical fiber loop coiling demand;Cure shrinkage is small, thermal expansion coefficient is low, elastic modulus change amplitude is small in -40-60 DEG C of use temperature ranges, optical fiber loop cumulative stress is small and uniform, it can guarantee the consistency of the additional stress and modulus to optical fiber loop, to guarantee the precision i.e. stability in use of optical fibre gyro.
Description
Technical field
The invention belongs to field of adhesive technology, and in particular to a kind of one-component anaerobic glue and its preparation side
Method.
Background technique
Adhesive is that weight accounting is maximum in optical fiber loop system, therefore, performance (such as adhesive strength, bullet of adhesive
Property modulus, glass transition temperature, cure shrinkage etc.) performance of optical fiber loop is influenced it is particularly important.Winding optical fiber at present
The widely used adhesive glue of ring is mainly two class of thermohardening type and ultraviolet curing type.Wherein thermohardening type generally uses double groups
Part silicon rubber, first group are divided into hydroxyl-terminated injecting two methyl siloxane, and second group is divided into alkoxy silane (such as ethyl orthosilicate, alkoxy
Polymethyl hydrogen siloxane etc.), main problem existing for this kind of adhesive is that working life is shorter, and viscosity constantly increases in use
Greatly, the durability requirements of optical fiber winding operation are unable to satisfy.Ultraviolet curing type generally uses urethane acrylate, epoxy third
Olefin(e) acid ester is prepolymer, and the composition such as reactive diluent, photoinitiator is added, and this kind of adhesive is one-component, but due to by purple
The limitation of outer smooth penetration depth, cannot act as optical fiber loop adhesive, be currently only used for the fast packing of optical fiber pigtail.
Summary of the invention
The purpose of the present invention is to solve the technical problems existing in the prior art, a kind of cure shrinkage and heat are provided
The coefficient of expansion is lower and can guarantee the one-component anaerobic glue of optical fiber winding operational stability demand.
Another object of the present invention is to provide a kind of one-component anaerobic glue and preparation method thereof.
In order to achieve the above object, the invention adopts the following technical scheme: a kind of one-component anaerobic glue, by with
The group of lower weight percent content is grouped as: methacrylate monomers 55-70%, polyurethane acrylate prepolymer 25-40%,
Initiator 1-2%, promotor 0.1-2%, stabilizer 0.05-2%, the polyurethane acrylate prepolymer is by following weight percent
Component than content is polymerized: diisocyanate 50-60%, dihydric alcohol 30-40%, methacrylic acid hydroxy ester 5-10%.
Further, the methacrylate monomers are methyl methacrylate, butyl methacrylate, metering system
Acid -2- ethylhexyl, glycidyl methacrylate, phenoxyethyl methacrylate, hydroxy propyl methacrylate, first
Base acrylic acid, neopentylglycol dimethacrylate, 1,6-HD dimethylacrylate, two contracting propylene glycol dimethyl allenes
One of acid esters, tripropylene glycol dimethylacrylate, trimethylol-propane trimethacrylate are a variety of.
Further, the diisocyanate is isophorone diisocyanate, dicyclohexyl methyl hydride diisocyanate, first
One of phenylene diisocyanate, methyl diphenylene diisocyanate.
Further, the dihydric alcohol is one of polyethylene glycol, polypropylene glycol, polytetrahydrofuran ether glycol.
Further, the methacrylic acid hydroxy ester is hydroxyethyl methacrylate, in hydroxy propyl methacrylate
It is a kind of.
Further, the initiator is benzoyl peroxide, dicumyl peroxide, cumyl hydroperoxide, benzene first
One of the peroxotungstic acid tert-butyl ester, tert-butyl hydroperoxide.
Further, the promotor is triethylamine, n,N-Dimethylaniline, tetrahydroquinoline, phenylthiourea, acetylacetone,2,4-pentanedione
Tin, zinc acetate, isooctyl acid copper, cobalt naphthenate, benzoic sulfimide, phthalimide, two hydrazine of 1,5- diphenyl phosphinylidyne, three
One or more of Phenylphosphine.
Further, the stabilizer is p-hydroxyanisole, hydroquinone, 2,6- di-tert-butylphenol, oxalic acid, EDTA-
One or more of 2Na.
A kind of preparation method of one-component anaerobic glue, method includes the following steps:
A, diisocyanate is added in the reaction flask with agitating heater, starts and stirs and be slowly introducing nitrogen, heat up
It instills dihydric alcohol in 40 DEG C, 0.5 hour, insulation reaction 1 hour, is warming up to 60 DEG C the reaction was continued to NCO content up to 6.25%;
Then in 65 DEG C of instillation methacrylic acid hydroxy esters, continue insulation reaction to NCO%≤0.3%;Cool down to obtain urethane acrylate
Prepolymer;
B, polyurethane acrylate prepolymer, methacrylate monomers, initiator, promotor and stabilizer are uniformly mixed
To one-component anaerobic glue.
The present invention has the advantages that one-component anaerobic glue of the invention by methyl compared with the prior art
Acrylate monomer, polyurethane acrylate prepolymer, initiator, promotor, stabilizer composition, polyurethane acrylate prepolymer are poly-
Object is polymerized by diisocyanate, dihydric alcohol, methacrylic acid hydroxy ester, which will not be crosslinked solid in the presence of air
Change, and viscosity is held essentially constant within storage period, in ring winding process, completely cuts off air, that is, cross-linkable solidifying.The present invention
Anaerobic adhesive can be used as optical fiber loop bonding adhesive for bonding, overcome that traditional two-component adhesive working life is short and ultra-violet curing
Adhesive can not deep cure defect;Anaerobism adhesiveness of the invention is small (≤500mPas), has to polarization maintaining optical fibre good
Wetability, bonding positioning can be realized in 1-5min after starvation, and 2-4h completion of cure under the conditions of 60 DEG C operates curability
Optical fiber loop coiling demand can be fully met;Anaerobic adhesive cure shrinkage of the invention is small, thermal expansion coefficient is low, at -40-60 DEG C
Elastic modulus change amplitude is small in use temperature range, optical fiber loop cumulative stress is small and uniform.Thereby it is ensured that optical fiber
The additional stress of ring and the consistency of modulus, optical fiber loop quality level is high, stable and reliable for performance, to guarantee optical fibre gyro
Precision, that is, stability in use.
Specific embodiment
Embodiment 1
A kind of one-component anaerobic glue, is grouped as: methyl methacrylate by the group of following weight percent content
60%, polyurethane acrylate prepolymer 35.9%, benzoyl peroxide 2%, triethylamine 0.1%, hydroxyanisol 2%, the poly- ammonia
Ester acrylic ester prepolymer is polymerized by the component of following weight percent content: isophorone diisocyanate 50%, poly- second
Glycol 40%, hydroxyethyl methacrylate 10%.
The preparation method of the one-component anaerobic glue the following steps are included:
A, isophorone diisocyanate is added in the reaction flask with agitating heater, starts and stirs and be slowly introducing nitrogen
Gas is warming up to 40 DEG C, polyethylene glycol is instilled in 0.5 hour, insulation reaction 1 hour, being warming up to 60 DEG C, the reaction was continued to NCO content
Up to 6.25%;Then in 65 DEG C of instillation hydroxyethyl methacrylates, continue insulation reaction to NCO%≤0.3%;Cool down to obtain polyurethane
Acrylic ester prepolymer;
B, polyurethane acrylate prepolymer, methyl methacrylate, benzoyl peroxide, triethylamine and hydroxyanisol are mixed
It closes and uniformly obtains one-component anaerobic glue.
Test its performance: viscosity 470mPa.s, tensile strength 4.2MPa, elongation 86%, elasticity modulus 6.6MPa, glass
Change 40 DEG C of transition temperature, tensile shear strength (glass-glass) 14.9MPa, cure shrinkage 2.1%, thermal expansion coefficient 276.5
×10-6/K。
Embodiment 2
A kind of one-component anaerobic glue, is grouped as: butyl methacrylate by the group of following weight percent content
20%, methacrylic acid -2- ethylhexyl 20%, glycidyl methacrylate 30%, polyurethane acrylate prepolymer
26.95%, dicumyl peroxide 1%, N, accelerine 0.5%, tetrahydroquinoline 0.5%, phenylthiourea 1%, hydroquinone
0.05%, the polyurethane acrylate prepolymer is polymerized by the component of following weight percent content: dicyclohexyl methyl hydride
Diisocyanate 60%, polypropylene glycol 35%, hydroxy propyl methacrylate 5%.
The preparation method of the one-component anaerobic glue the following steps are included:
A, dicyclohexyl methyl hydride diisocyanate is added in the reaction flask with agitating heater, starts and stirs and slowly lead to
Enter nitrogen, be warming up to 40 DEG C, polypropylene glycol is instilled in 0.5 hour, insulation reaction 1 hour, being warming up to 60 DEG C, the reaction was continued to NCO
Content is up to 6.25%;Then in 65 DEG C of instillation hydroxy propyl methacrylates, continue insulation reaction to NCO%≤0.3%;Cool down poly-
Urethane acrylate prepolymer;
B, by polyurethane acrylate prepolymer, butyl methacrylate, methacrylic acid -2- ethylhexyl, methacrylic acid
Ethylene oxidic ester, dicumyl peroxide, N, accelerine, tetrahydroquinoline, phenylthiourea and hydroquinone are uniformly mixed
To one-component anaerobic glue.
Test its performance: viscosity 456mPa.s, tensile strength 4.6MPa, elongation 79%, elasticity modulus 6.3MPa, glass
Change 40 DEG C of transition temperature, tensile shear strength (glass-glass) 13.7MPa, cure shrinkage 2.5%, thermal expansion coefficient 301.3
×10-6/K。
Embodiment 3
A kind of one-component anaerobic glue, is grouped as by the group of following weight percent content: methacrylic acid phenoxy group
Ethyl ester 20%, hydroxy propyl methacrylate 20%, methacrylic acid 26.5%, polyurethane acrylate prepolymer 30%, peroxidating
Hydroxyl isopropylbenzene 1.5%, acetylacetone,2,4-pentanedione tin 0.3%, zinc acetate 0.3%, isooctyl acid copper 0.4%, 2,6- di-tert-butylphenol 1%, it is described poly-
Urethane acrylate prepolymer is polymerized by the component of following weight percent content: 55 % of toluene di-isocyanate(TDI), poly- four
Hydrogen furans ether glycol 37%, hydroxyethyl methacrylate 8%.
The preparation method of the one-component anaerobic glue the following steps are included:
A, toluene di-isocyanate(TDI) is added in the reaction flask with agitating heater, starts and stirs and be slowly introducing nitrogen,
40 DEG C are warming up to, instills polytetrahydrofuran ether glycol in 0.5 hour, insulation reaction 1 hour, is warming up to 60 DEG C the reaction was continued extremely
NCO content is up to 6.25%;Then in 65 DEG C of instillation hydroxyethyl methacrylates, continue insulation reaction to NCO%≤0.3%;Cool down
Polyurethane acrylate prepolymer;
B, by polyurethane acrylate prepolymer, phenoxyethyl methacrylate, hydroxy propyl methacrylate, metering system
Acid, cumyl hydroperoxide, acetylacetone,2,4-pentanedione tin, zinc acetate, isooctyl acid copper and 2,6- di-tert-butylphenol are uniformly mixed and obtain list
Component acrylic ester anaerobic adhesive.
Test its performance: viscosity 428mPa.s, tensile strength 5.1MPa, elongation 81%, elasticity modulus 6.5MPa, glass
Change 40 DEG C of transition temperature, tensile shear strength (glass-glass) 16.1MPa, cure shrinkage 2.9%, thermal expansion coefficient 288.9
×10-6/K。
Embodiment 4
A kind of one-component anaerobic glue, is grouped as by the group of following weight percent content: neopentyl glycol dimethyl propylene
Olefin(e) acid ester 23%, 1,6-HD dimethylacrylate 23%, two contracting dimethacrylates 23%, polyurethane propylene
Acid esters prepolymer 25%, benzoic acid t-butylperbenzoate 2%, cobalt naphthenate 0.5%, benzoic sulfimide 0.5%, phthalyl are sub-
Amine 1%, oxalic acid 2%, the polyurethane acrylate prepolymer are polymerized by the component of following weight percent content: diphenyl
Methane diisocyanate 60%, polyethylene glycol 30%, hydroxy propyl methacrylate 10%.
The preparation method of the one-component anaerobic glue the following steps are included:
A, methyl diphenylene diisocyanate is added in the reaction flask with agitating heater, starts and stirs and be slowly introducing
Nitrogen is warming up to 40 DEG C, instills polyethylene glycol in 0.5 hour, insulation reaction 1 hour, is warming up to 60 DEG C the reaction was continued to NCO and contain
It measures up to 6.25%;Then in 65 DEG C of instillation hydroxy propyl methacrylates, continue insulation reaction to NCO%≤0.3%;Cool down to obtain poly- ammonia
Ester acrylic ester prepolymer;
B, by polyurethane acrylate prepolymer, neopentylglycol dimethacrylate, 1,6-HD dimethylacrylate,
Two contracting dimethacrylates, benzoic acid t-butylperbenzoate, cobalt naphthenate, benzoic sulfimide, phthalyl
Imines and oxalic acid, which are uniformly mixed, obtains one-component anaerobic glue.
Test its performance: viscosity 453mPa.s, tensile strength 4.8MPa, elongation 77%, elasticity modulus 6.3MPa, glass
Change 40 DEG C of transition temperature, tensile shear strength (glass-glass) 14.6MPa, cure shrinkage 2.7%, thermal expansion coefficient 290.1
×10-6/K。
Embodiment 5
A kind of one-component anaerobic glue, is grouped as by the group of following weight percent content: tripropylene glycol dimethyl
Acrylate 25%, trimethylol-propane trimethacrylate 30%, polyurethane acrylate prepolymer 40%, t-butyl peroxy
Change hydrogen 1.5%, 1,5- diphenyl phosphinylidyne, two hydrazine 1%, triphenylphosphine 0.5%, 2,6- di-tert-butylphenol 1%, EDTA-2Na 1%, it is described
Polyurethane acrylate prepolymer is polymerized by the component of following weight percent content: dicyclohexyl methyl hydride diisocyanate
55 %, polypropylene glycol 35%, hydroxyethyl methacrylate 10%.
The preparation method of the one-component anaerobic glue the following steps are included:
A, dicyclohexyl methyl hydride diisocyanate is added in the reaction flask with agitating heater, starts and stirs and slowly lead to
Enter nitrogen, be warming up to 40 DEG C, polypropylene glycol is instilled in 0.5 hour, insulation reaction 1 hour, being warming up to 60 DEG C, the reaction was continued to NCO
Content is up to 6.25%;Then in 65 DEG C of instillation hydroxyethyl methacrylates, continue insulation reaction to NCO%≤0.3%;Cool down poly-
Urethane acrylate prepolymer;
B, by polyurethane acrylate prepolymer, tripropylene glycol dimethylacrylate, trimethylol propane trimethyl propylene
Acid esters, tert-butyl hydroperoxide, two hydrazine of 1,5- diphenyl phosphinylidyne, triphenylphosphine, 2,6- di-tert-butylphenol, EDTA-2Na mixing are equal
It is even to obtain one-component anaerobic glue.
Test its performance: viscosity 441mPa.s, tensile strength 5.0MPa, elongation 73%, elasticity modulus 6.4MPa, glass
Change 40 DEG C of transition temperature, tensile shear strength (glass-glass) 15.5MPa, cure shrinkage 2.4%, thermal expansion coefficient 281.7
×10-6/K。
Claims (9)
1. a kind of one-component anaerobic glue, it is characterised in that: be grouped as by the group of following weight percent content: methyl
Acrylate monomer 55-70%, polyurethane acrylate prepolymer 25-40%, initiator 1-2%, promotor 0.1-2%, stabilizer
0.05-2%, the polyurethane acrylate prepolymer are polymerized by the component of following weight percent content: diisocyanate
50-60%, dihydric alcohol 30-40%, methacrylic acid hydroxy ester 5-10%.
2. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the methacrylate
Monomer is methyl methacrylate, butyl methacrylate, methacrylic acid -2- ethylhexyl, methyl propenoic acid glycidyl
Ester, phenoxyethyl methacrylate, hydroxy propyl methacrylate, methacrylic acid, neopentylglycol dimethacrylate,
1,6-HD dimethylacrylate, two contracting dimethacrylates, tripropylene glycol dimethylacrylate, three
One of methylolpropane trimethacrylate is a variety of.
3. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the diisocyanate is
Isophorone diisocyanate, dicyclohexyl methyl hydride diisocyanate, toluene di-isocyanate(TDI), methyl diphenylene diisocyanate
One of.
4. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the dihydric alcohol is poly- second
One of glycol, polypropylene glycol, polytetrahydrofuran ether glycol.
5. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the hydroxyethyl methacrylate
Base ester is one of hydroxyethyl methacrylate, hydroxy propyl methacrylate.
6. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the initiator is peroxide
Change benzoyl, dicumyl peroxide, cumyl hydroperoxide, benzoic acid t-butylperbenzoate, in tert-butyl hydroperoxide
It is a kind of.
7. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the promotor is three second
Amine, N, accelerine, tetrahydroquinoline, phenylthiourea, acetylacetone,2,4-pentanedione tin, zinc acetate, isooctyl acid copper, cobalt naphthenate, adjacent sulphur
One or more of acyl benzoylimino, phthalimide, two hydrazine of 1,5- diphenyl phosphinylidyne, triphenylphosphine.
8. a kind of one-component anaerobic glue according to claim 1, it is characterised in that: the stabilizer is to hydroxyl
One or more of base methyl phenyl ethers anisole, hydroquinone, 2,6- di-tert-butylphenol, oxalic acid, EDTA-2Na.
9. a kind of preparation method of one-component anaerobic glue, it is characterised in that method includes the following steps:
A, diisocyanate is added in the reaction flask with agitating heater, starts and stirs and be slowly introducing nitrogen, heat up
It instills dihydric alcohol in 40 DEG C, 0.5 hour, insulation reaction 1 hour, is warming up to 60 DEG C the reaction was continued to NCO content up to 6.25%;
Then in 65 DEG C of instillation methacrylic acid hydroxy esters, continue insulation reaction to NCO%≤0.3%;Cool down to obtain urethane acrylate
Prepolymer;
B, polyurethane acrylate prepolymer, methacrylate monomers, initiator, promotor and stabilizer are uniformly mixed
To one-component anaerobic glue.
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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GB2582957A (en) * | 2019-04-11 | 2020-10-14 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
CN112175568A (en) * | 2020-09-21 | 2021-01-05 | 禹城市三星科技有限公司 | High-toughness and high-strength anaerobic adhesive and preparation method thereof |
CN112680171A (en) * | 2020-12-16 | 2021-04-20 | 湖南世纪特邦新材料有限公司 | Anaerobic adhesive and preparation method and application thereof |
CN113717681A (en) * | 2021-10-20 | 2021-11-30 | 山东智久新材料科技有限公司 | Adhesive for medical stainless steel needle |
CN113736424A (en) * | 2021-09-30 | 2021-12-03 | 烟台德邦科技股份有限公司 | Single-component thermosetting polyurethane structural adhesive and preparation method thereof |
CN117801726A (en) * | 2023-12-28 | 2024-04-02 | 浙江凯越新材料技术有限公司 | Bi-component acrylic ester adhesive and preparation method and application method thereof |
-
2018
- 2018-12-07 CN CN201811496366.7A patent/CN109810665A/en active Pending
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2582957A (en) * | 2019-04-11 | 2020-10-14 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
GB2582957B (en) * | 2019-04-11 | 2022-08-17 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
CN112175568A (en) * | 2020-09-21 | 2021-01-05 | 禹城市三星科技有限公司 | High-toughness and high-strength anaerobic adhesive and preparation method thereof |
CN112680171A (en) * | 2020-12-16 | 2021-04-20 | 湖南世纪特邦新材料有限公司 | Anaerobic adhesive and preparation method and application thereof |
CN113736424A (en) * | 2021-09-30 | 2021-12-03 | 烟台德邦科技股份有限公司 | Single-component thermosetting polyurethane structural adhesive and preparation method thereof |
CN113717681A (en) * | 2021-10-20 | 2021-11-30 | 山东智久新材料科技有限公司 | Adhesive for medical stainless steel needle |
CN117801726A (en) * | 2023-12-28 | 2024-04-02 | 浙江凯越新材料技术有限公司 | Bi-component acrylic ester adhesive and preparation method and application method thereof |
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Application publication date: 20190528 |