CN109370507A - A kind of three proofings adhesive and preparation method thereof of low viscosity environmental protection UV/ moisture dual cure - Google Patents
A kind of three proofings adhesive and preparation method thereof of low viscosity environmental protection UV/ moisture dual cure Download PDFInfo
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- CN109370507A CN109370507A CN201811294787.1A CN201811294787A CN109370507A CN 109370507 A CN109370507 A CN 109370507A CN 201811294787 A CN201811294787 A CN 201811294787A CN 109370507 A CN109370507 A CN 109370507A
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- low viscosity
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
A kind of three proofings adhesive and preparation method thereof of low viscosity environmental protection UV/ moisture dual cure, it is made of the raw material of parts by weight once: moisture cured 30~50 parts of acrylate of self-control low viscosity, make 10~30 parts of low viscosity bifunctionality urethane acrylate by oneself, 30~50 parts of acrylic compounds reactive diluent, 3~8 parts of photoinitiator, 0.05~0.2 part of polymerization inhibitor agent, 1~3 part of silane coupling agent.The invention provides a kind of viscosity lower than 50mPa.s, easily sprays, levelling effect is good, toughness is good, adhere to the survey of hundred lattice and reach 5B, and be difficult in ultraviolet light the region irradiated, low viscosity environmental protection UV/ moisture dual cure three proofings adhesive of the invention has lower viscosity, without any solvent flashing, curing rate is fast, and surface drying is good, good toughness, bonding reliability is high, applied widely.
Description
Technical field
The invention belongs to photo-curing material fields, and in particular to the three of a kind of UV/ moisture dual cure of low viscosity environmental protection
Anti- adhesive and preparation method thereof.
Background technique
It is well known that ultraviolet cured adhesive sticks, agent is good with compatibility, curing rate is fast, and intensity height, environmental protection etc. are some aobvious
Work feature, therefore it is widely used in the fields such as optical field, electronic apparatus, optical digital disk.With UV-curing technology application
The continuous extension in field, ultraviolet cured adhesive all plays in the products such as mobile phone, television set, computer, navigator, Vehicular display device
Important role.As electronic product is increasingly turned to miniaturization, integrated, multifunction, Electronic Assemblies industry is also in the hair of high speed
Exhibition, the requirement to the security performance and reliability of completed knocked down products is also higher and higher, especially printed wiring board, due to electronic device
It is applied to daily life more and more widely, therefore consumer also increasingly pays close attention to the quality and reliability of product, " three proofings now
(moisture-proof, salt spray proof, antistatic) " is mentioned by more and more production firms and payes attention to.
However, most of in " the three proofings glue " used at present is all solvent based product, (it is less than its advantage is that viscosity is low
50mPa.s), glue spraying is convenient, applied widely.But the disadvantage is that operating environment is more severe, due to largely using toxic stupid class
Solvent, operator are influenced health, Long Term Contact and the easy induction occupational disease that works in the environment by solvent harm, and
And its inflammable and explosive feature, so that respectively putting into a large amount of fund manpower in fire-fighting and trouble free service using enterprise carries out pipe
Reason.It is big additionally, due to solvent volatilization, economically also waste very much.With the raising of environmental requirement, both at home and abroad to volatile solvent
Also stringent limitation has been started.Although having already appeared not solvent-laden environmentally friendly " three proofings glue " currently on the market, its viscosity is universal
Higher than 150mPa.s, product of the glue spraying thickness lower than 20um is required to be unable to satisfy requirement for some.Develop novel low viscosity ring
Guarantor's type solvent-free " three proofings glue " replaces current solvent based product as an urgent demand in market.
Summary of the invention
The invention is to solve the problems of the prior art, provides a kind of viscosity lower than 50mPa.s, easily sprays, levelling
Effect is good, and toughness is good, and attachment hundred lattice survey reaches 5B, and is difficult in ultraviolet light the region irradiated, and is solidified by moisture-crosslinking, thus
Implement the protective effect to various complicated type wiring boards.It is a further object of the present invention to provide this low viscosity environmental protection UV/ is wet
The preparation method of gas dual cure three proofings adhesive.The technical scheme to solve the above technical problems is that
A kind of low viscosity environmental protection UV/ moisture dual cure three proofings adhesive, is made of the raw material of parts by weight once: self-control is low viscous
30~50 parts of moisture cured acrylate is spent, makes 10~30 parts of low viscosity bifunctionality urethane acrylate, propylene by oneself
30~50 parts of acids reactive diluent, 3~8 parts of photoinitiator, 0.05~0.2 part of polymerization inhibitor agent, 1~3 part of silane coupling agent；
The moisture cured acrylate of the self-control low viscosity, is the hydroxy acrylate with HDI trimer, polymerization inhibitor and anti-
The acrylate containing NCO group of oxygen agent synthesis；
The self-control low viscosity bifunctionality urethane acrylate polyether Glycols and is urged with monoisocyanates monomer
The polyether-type acrylic resin of agent synthesis.
Further, the moisture cured acrylate molecule formula of the low viscosity is as follows:
Wherein: R1 and R2 respectively represents one kind of H or CH3.
Further, the moisture cured acrylate of the low viscosity refers to HDI trimer, hydroxyl third
Olefin(e) acid ester, the acrylate containing NCO group of polymerization inhibitor and antioxidant synthesis, the hydroxy acrylate are
One or more of hydroxy-ethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxy propyl methacrylate
Mixture；The polymerization inhibitor is p-hydroxyanisole, 1,4-benzoquinone, one or more of hydroquinone and naphthoquinones；Described is anti-
Oxygen agent is BHT(2,6- di-tert-butyl-4-methy phenol) and TPP(triphenyl phosphite) in it is one or two kinds of；Low viscosity is wettable
The synthetic method of curing acrylate is: by 1mol tripolymer, 50ppm polymerization inhibitor, 100ppm antioxidant, which is added to, to be had
In the three-necked flask of thermometer, heating stirring when temperature reaches 50 DEG C, is added hydroxy acrylate 1mol, is continuously heating to 70
~80 DEG C, 2~3h is reacted under the conditions of temperature is 70~80 DEG C, discharge the propylene moisture cured to get low viscosity after cooling
Acid esters.
Further, the low viscosity bifunctionality urethane acrylate molecular formula is as follows:
Wherein: R1 represents one kind of H or CH3, and R2 represents polyether Glycols.
Further, the low viscosity bifunctionality urethane acrylate refers to monoisocyanates monomer,
The polyether-type acrylic resin of polyether Glycols and catalyst synthesis, the monoisocyanates monomer include Japanese Showa electrician
MOI or AOI one or two kinds of mixing, the polyetherdiol includes polyethylene glycol, polypropylene glycol and polytetrahydrofuran
The mixing of the medium one or any of several of glycol, the molecular weight of polyether Glycols is 500~1500., the catalyst is organic
Two kinds of one of tin compound and dibutyl tin dilaurate or arbitrary proportion.Viscosity bifunctionality urethane acrylate
Synthetic method be: 2.2mol isocyanate-monomer is added in the three-necked flask with thermometer, heating stirring, temperature arrives
When up to 60 DEG C, 1mol polyetherdiol is added, 20ppm catalyst is added, is warming up to 70-75 DEG C, reacts 2~3h, uses infrared spectroscopy
Instrument analyzes the content of OH group, when the peak of OH completely disappears, stops that reaction is added, obtains low viscosity bifunctionality polyurethane third
Olefin(e) acid ester.
Further, the acrylic compounds reactive diluent includes (methyl) isobornyl acrylate, (methyl) acrylic acid
Different monooctyl ester and (methyl) acrylic acid tetrahydrofuran, trimethylolpropane formal acrylate, in tridecyl acrylate
It is one or more, and the combination of preferably (methyl) isobornyl acrylate and (methyl) acrylic acid tetrahydrofuran.
Further, the photoinitiator is selected from benzil ketals class, hydroxyl ketone, amido ketone, acylphosphanes peroxidating
One of Liquid photoinitiators LBC, LBP, LTM, MBF of species and RAHN company or a variety of, preferably 184(1- hydroxyl-
Phenylcyclohexyl ketone), the combination of TPO (2,4,6- trimethylbenzoy-dipheny phosphine oxide) and LTM.
Further, the polymerization inhibitor is p-hydroxyanisole, 1,4-benzoquinone, one or more of hydroquinone and naphthoquinones
Combination.
Further, the silane coupling agent, including KH551, KH172, KH560, one of KH570 or any are several
Combination.
It is described the invention also provides a kind of method for preparing low viscosity environmental protection UV/ moisture dual cure three proofings adhesive
Method successively comprises the steps of:
It makes the moisture cured acrylate of low viscosity by oneself, makes low viscosity bifunctionality urethane acrylate, acrylic compounds by oneself
Reactive diluent, polymerization inhibitor agent, silane coupling agent sequentially add in blender, temperature control at 20~30 DEG C, vacuum condition is-
0.1~-0.08MPa is stirred 0.5~1 hour in 500~1000 revs/min, until stirring evenly, nitrogen release；
Photoinitiator is added in blender, is protected from light, and at 20~30 DEG C, vacuum condition is -0.1~-0.08MPa for temperature control, in
500~1000 revs/min are stirred 0.5~1 hour, until stirring evenly, nitrogen release.
The beneficial effects of the present invention are:
Low viscosity environmental protection UV/ moisture dual cure three proofings adhesive prepared by the present invention, it is moisture cured by self-control low viscosity
Resin, viscosity 6000-8000mPa.s, NCO content reaches 12-15%, and common moisture-curable resin NCO content is 6-9%,
And then it can more rapidly be reacted under moist conditions；It is synthesized by the isocyanate-monomer of single NCO group with polyetherdiol low viscous
Spend bifunctionality urethane acrylate, viscosity 2000-4000mPa.s, well below common polyurethane acrylic resin, drop
The 20-30% of the usage amount of monomer, improves the toughness of product while product accomplishes low viscosity in low adhesive, and
Double bond in AOI/MOI has higher reactivity, can effectively overcome the oxygen inhibition in adhesive solidification process, protects
Demonstrate,prove the superiority of the surface drying when thin film coatings solidify.Low viscosity environmental protection UV/ moisture dual cure three proofings adhesive tool of the invention
There is lower viscosity, without any solvent flashing, curing rate is fast, and surface drying is good, good toughness, and bonding reliability is high, applied widely.
Specific embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1
The moisture cured acrylate of self-control low viscosity follows the steps below:
By 1molHDI tripolymer, 50ppm polymerization inhibitor, 100ppm antioxidant is added in the three-necked flask with thermometer, heating
Stirring when temperature reaches 50 DEG C, is added hydroxy acrylate 1mol, is continuously heating to 70~80 DEG C, is 70~80 DEG C in temperature
Under the conditions of react 2~3h, discharge the acrylate moisture cured to get low viscosity after cooling.
Embodiment 2
Self-control viscosity bifunctionality urethane acrylate follows the steps below:
2.2mol isocyanate-monomer is added in the three-necked flask with thermometer, heating stirring, when temperature reaches 60 DEG C,
1mol polyetherdiol is added, 20ppm catalyst is added, is warming up to 70-75 DEG C, reacts 2~3h, analyzes OH base with infrared spectrometer
The content of group stops that reaction is added, obtains low viscosity bifunctionality urethane acrylate when the peak of OH completely disappears.
Embodiment 3
The acrylate that the present invention selects self-control low viscosity moisture cured, makes low viscosity bifunctionality polyurethane acroleic acid by oneself
Ester, acrylic compounds reactive diluent, photoinitiator, polymerization inhibitor agent, silane coupling agent are prepared low viscous by suitable formula number
Spend environmental protection UV/ moisture dual cure three proofings adhesive.
It is the embodiment that inventor provides below, however, the present invention is not limited to these examples.
Table one
Preparation method:
Various raw materials are successively accurately weighed by with formula number in table 1, the moisture cured acrylate of low viscosity will be made by oneself, from
Low viscosity bifunctionality urethane acrylate processed, isobornyl acrylate, acrylic acid tetrahydrofuran, photoinitiator 184, light
Initiator TPO, photoinitiator LTM, polymerization inhibitor 1,4-benzoquinone, coupling agent KH570 are sequentially added in blender, temperature control 20~
30 DEG C, vacuum condition is -0.1~-0.08MPa, is stirred 0.5~1 hour in 500~1000 revs/min, until stir evenly,
Nitrogen release；
Photoinitiator is added in the blender after release, is protected from light, temperature control at 20~30 DEG C, vacuum condition is -0.1~-
0.08MPa is stirred 0.5~1 hour in 500~1000 revs/min, until stirring evenly, nitrogen release.
Pass through the above-mentioned low viscosity environmental protection UV/ moisture dual cure three being prepared such as the different ratio of 1 comparative example 1-7 of table
Anti- adhesive.
The performance test methods of each comparative example in table 1 are described in detail below:
Ultraviolet light solidifies: solidified by using the ultraviolet light in about 200nm~400nm wavelength, radiation energy 20~
50mJ/cm2。
Moisture-curable: the room of constant temperature and humidity (23 ± 2 DEG C, 50 ± 10%RH) is placed it in the case where being absolutely protected from light
Between stand.To guarantee to be protected from light, sample can be covered with aluminium-foil paper.Then solidification knot is checked according to the object time of design
Fruit.
The test condition of adhesive force, elongation at break and hardness is: ultraviolet light solidifies 1000mJ/cm2, then moisture-curable
48 hours.
Viscosity test: cone and plate viscometer acquires average value using 42# rotor 100r test three times.
It is as follows to the performance test methods result of each embodiment in table 1:
From the embodiment data in table it follows that
Low viscosity environmental protection UV/ moisture dual cure three proofings adhesive of the invention has lower viscosity, without any solvent flashing,
Curing rate is fast, and surface drying is good, good toughness, and bonding reliability is high, and the viscosity of the three proofings adhesive of different ratio is below
50mPa.s, attachment hundred lattice survey reach 5B.
The composition proportion that comparative example 1 can be obtained from comparative example can make low viscosity environmental protection UV/ moisture dual cure three proofings gluing
Agent is in curing rate, surface drying time, adhesive force, toughness, performance is more average in hardness and viscosity and relative good can be used as it is excellent
Apolegamy ratio.
Embodiment described above, only preferred embodiments of the invention, be not to limit practical range of the invention, therefore it is all according to
The equivalent change or modification that structure, feature and principle described in scope of the present invention patent is done should all include and the present invention
In patent claim.
Claims (10)
1. a kind of low viscosity environmental protection UV/ moisture dual cure three proofings adhesive, is made of the raw material of parts by weight once: self-control is low
Moisture cured 30~50 parts of acrylate of viscosity
Make 10~30 parts of low viscosity bifunctionality urethane acrylate by oneself
30~50 parts of acrylic compounds reactive diluent
3~8 parts of photoinitiator
0.05~0.2 part of polymerization inhibitor agent
1~3 part of silane coupling agent
The moisture cured acrylate of the self-control low viscosity, is the hydroxy acrylate with HDI trimer, polymerization inhibitor and anti-
The acrylate containing NCO group of oxygen agent synthesis；
The self-control low viscosity bifunctionality urethane acrylate polyether Glycols and is urged with monoisocyanates monomer
The polyether-type acrylic resin of agent synthesis.
2. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
Low viscosity it is moisture cured acrylate molecule formula it is as follows:
Wherein: R1 and R2 respectively represents one kind of H or CH3.
3. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
Hydroxy acrylate be hydroxy-ethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxy propyl methacrylate
One or more of mixture；
The polymerization inhibitor is p-hydroxyanisole, 1,4-benzoquinone, one or more of hydroquinone and naphthoquinones；
The antioxidant is BHT(2,6- di-tert-butyl-4-methy phenol) and TPP(triphenyl phosphite) in it is a kind of or two
Kind.
4. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
The synthetic method of the moisture cured acrylate of self-control low viscosity is: by 1molHDI tripolymer, 50ppm polymerization inhibitor, 100ppm
Antioxidant is added in the three-necked flask with thermometer, heating stirring, and when temperature reaches 50 DEG C, hydroxy acrylate is added
1mol is continuously heating to 70~80 DEG C, and 2~3h is reacted under the conditions of temperature is 70~80 DEG C, and discharging is after cooling to get low viscosity
Moisture cured acrylate.
5. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
Low viscosity bifunctionality urethane acrylate molecular formula it is as follows:
Wherein: R1 represents one kind of H or CH3, and R2 represents polyether Glycols.
6. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
Monoisocyanates monomer include Japanese Showa electrician MOI or AOI one or two kinds of mixing；
The polyetherdiol includes polyethylene glycol, polypropylene glycol and the medium one or any of several of polytetrahydrofuran diol it is mixed
It closes；
For the molecular weight of polyether Glycols 500~1500, the catalyst is organo-tin compound and dibutyl tin dilaurate
One of or two kinds of arbitrary proportion.
7. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
The synthetic method of self-control viscosity bifunctionality urethane acrylate is: 2.2mol isocyanate-monomer is added to temperature
In the three-necked flask of meter, when temperature reaches 60 DEG C, 1mol polyetherdiol is added in heating stirring, and 20ppm catalyst, heating is added
To 70-75 DEG C, 2~3h is reacted, stops being added when the peak of OH completely disappears with the content of infrared spectrometer analysis OH group
Reaction, obtains low viscosity bifunctionality urethane acrylate.
8. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
Acrylic compounds reactive diluent include (methyl) isobornyl acrylate, (methyl) Isooctyl acrylate monomer and (methyl) propylene
One of sour tetrahydrofuran, trimethylolpropane formal acrylate, tridecyl acrylate are a variety of, preferably
The combination of (methyl) isobornyl acrylate and (methyl) acrylic acid tetrahydrofuran.
9. low viscosity environmental protection UV/ moisture dual cure three proofings adhesive according to claim 1, which is characterized in that described
Photoinitiator be selected from benzil ketals class, hydroxyl ketone, amido ketone, acylphosphanes peroxide and RAHN company liquid
One of body photoinitiator LBC, LBP, LTM, MBF or a variety of, preferably 184(1- hydroxy-cyciohexyl Benzophenone), TPO (2,
4,6- trimethylbenzoy-dipheny phosphine oxides) and LTM combination, the polymerization inhibitor is p-hydroxyanisole, 1,4-benzoquinone,
The combination of one or more of hydroquinone and naphthoquinones, the silane coupling agent is KH551, KH172, KH560, KH570
One of or any several combinations.
10. a kind of preparation method of low viscosity environmental protection UV/ moisture dual cure three proofings adhesive, the method is successively by following step
Rapid composition:
The moisture cured acrylate of low viscosity will be made by oneself, make low viscosity bifunctionality urethane acrylate, acrylic acid by oneself
Class reactive diluent, polymerization inhibitor agent, silane coupling agent sequentially add in blender, and temperature control is at 20~30 DEG C, vacuum condition
It for -0.1~-0.08MPa, is stirred 0.5~1 hour in 500~1000 revs/min, until stirring evenly, nitrogen release；
Photoinitiator is added in the blender in step a after release, is protected from light, temperature control at 20~30 DEG C, vacuum condition is-
0.1~-0.08MPa is stirred 0.5~1 hour in 500~1000 revs/min, until stirring evenly, nitrogen release.
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| CN110128994A (en) * | 2019-04-09 | 2019-08-16 | 中海油常州涂料化工研究院有限公司 | A kind of anaerobic adhesive of moisture-curable and preparation method thereof |
| CN111040614A (en) * | 2019-12-06 | 2020-04-21 | 上海航天化工应用研究所 | UV/moisture dual-curing primer for special organosilicon heat-proof coating and preparation method thereof |
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