CN107057068A - A kind of end epoxy silicon oil and preparation method thereof and its as adhesion promoters purposes - Google Patents
A kind of end epoxy silicon oil and preparation method thereof and its as adhesion promoters purposes Download PDFInfo
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- CN107057068A CN107057068A CN201710099731.XA CN201710099731A CN107057068A CN 107057068 A CN107057068 A CN 107057068A CN 201710099731 A CN201710099731 A CN 201710099731A CN 107057068 A CN107057068 A CN 107057068A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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Abstract
Epoxide group is contained at the two ends of the end epoxy silicon oil of the present invention, and repeat unit side chain contains alkylene；The present invention end epoxy silicon oil can as add-on type liquid silicon rubber adhesion promoters, do not influence silicon rubber solidification after light transmittance；Bonding activity is high, can just realize that add-on type liquid silicon rubber is bonded to the body of the base materials such as glass, PC and PMMA at 60 DEG C, be subjected to after 1000h tropical deterioration, can also also keep preferable adhesive effect.The present invention also provides the preparation method of end epoxy silicon oil, including：By the oligomeric cyclosiloxane of olefin-containing base under acid catalysis with epoxy double-seal head agent ring-opening polymerisation, the preparation method technique is simple, and product stability is good.
Description
Technical field
The present invention relates to organosilicon macromolecule compound field, more particularly to a kind of silicone oil and preparation method thereof and its
The purposes of field of liquid silicone rubber.
Background technology
Add-on type liquid silicon rubber has fabulous weatherability and physical and mechanical properties, is widely used in the filling of electronics industry
The fields such as envelope, coating and sealing.Because silicone molecules are in nonpolar in itself, viscous force when in use between base material is not enough, difficult
To meet use requirement.At present, the method for improving add-on type liquid silicon rubber and substrate bonding mainly has three kinds：(1) bottom is used
Paint is handled substrate surface, the not only easy generation environment pollution problem of this method, also add production process and drop
Low production efficiency；(2) by changing silicone molecules structure, cementability is strengthened, but this method actual production process compares
Complexity, specific aim is not strong and cost is of a relatively high；(3) by adding adhesion promoters in liquid silastic, addition is improved
The adhesive property of type liquid silastic, this method is simple and easy to apply, and can realize quickly change according to the different of base material
And response.
The synthetic methods of liquid silastic adhesion promoters is a lot, and to the plastic basis materials such as PVC, PPA, glass, ceramics or
The cementability of metal is poor.Chinese patent CN102703023B discloses a kind of synthesis side of liquid silastic adhesion promoters
Method, synthesizes terminal hydroxy group methyl vinyl silicon oil first, then using the terminal hydroxy group methyl vinyl silicon oil of synthesis be reactant through piptonychia
Alcohol reaction obtains the addition-type silicon rubber adhesion promoters containing epoxide group, silicon methoxy group and vinyl group, can be used for
The cementability of the materials such as plastic basis material or metal such as caking property poor PVC, PPA is improved, but to PC and PET etc. cementability
Difference, and need by two-step reaction, side reaction is also easy to produce, the yield of final product is influenceed.Week is to pass through polymethyl hydrogen siloxane
With 1, the hydrosilylation between 6 one hexanediyl esters, synthesis contains acrylate-based organosilicon adhesion promoters,
Also have for bonding between addition-type silicon rubber and PET base material, but in course of reaction 1,6 one hexanediyl esters from
The side reactions such as the dehydrogenation reaction of poly- and polymethyl hydrogen siloxane occur, the more difficult control of process.Pan Kexue is closed by ether exchange reaction
Into (3 one glycidoxypropyl group) allyloxy dimethoxysilane, [2,2 a pair ofs (allyloxy methyl) butoxy] (3 one
Glycidoxypropyl group) dimethoxysilane and [[a pair of of 3- allyloxys 1 (allyloxy methyl) propoxyl group] (3 one rings
Oxygen propoxypropyl) silane compound adhesion promoters of three kinds of the dimethoxysilane containing vinyl and epoxy radicals, but bond
Activation temperature is high, and in ether exchange process, silane coupler presoma autohemagglutination excessive velocities are also easy to produce sediment and occur side reaction.
The content of the invention
To improve add-on type liquid silicon rubber to the adhesive property of glass, ceramics, metal and various high polymer materials, overcome
Conventional organosilicon adhesion promoters are poor to PC, PMMA etc. cementability in the prior art, and bonding activation temperature is high, and influence main body is matched somebody with somebody
Side is transparent, waits deficiency there is provided a kind of to the bonding of glass, ceramics, metal and various high polymer materials synthesis side reaction more,
And the end epoxy silicon oil good to PC and PMMA caking property and preparation method thereof, and it is used as the adhesion promoter of add-on type liquid silicon rubber
Agent.
The present invention provides a kind of end epoxy silicon oil, shown in the end epoxy silicon oil general structure such as formula (I)：
R in formula (I)1、R2、R3、R4For C1~C3 alkyl；R5For C2~C4 alkylene, R6Alkyl for C1~C3 or
Unsaturated aromatic hydrocarbon base；N is the integer between 5~20；
It is preferred that the R1、R2、R3、R4It is methyl；
It is preferred that the R5For vinyl or acrylic；Most preferably described R5For vinyl；
It is preferred that the R6For methyl or phenyl, most preferably described R6For methyl；
It is preferred that n is 5~10 integer；
The viscosity of the end epoxy silicon oil is 25~200mPas；
The contents of ethylene of the end epoxy silicon oil is 2~8% (mass fractions)；
The present invention also provides the preparation method of above-mentioned end epoxy silicon oil, comprises the following steps：
(1) pretreatment of raw material：By acid catalyst in being dried in vacuo 24h at 60~90 DEG C, fully to remove moisture, olefin-containing
In 1~2h of water removal under 80~120 DEG C of vacuum conditions in the oligomeric cyclosiloxane input reaction vessel of base；The oligomeric cyclosiloxane
For six, eight, ten or twelve-ring；
(2) ring-opening polymerization：High pure nitrogen is passed through into reaction vessel, and adds the agent of epoxy double-seal head and dried
Acid catalyst, is warming up to 60~90 DEG C, reacts 3~8h, you can obtain the end epoxy silicon oil of the present invention；The alkylene it is oligomeric
Cyclosiloxane, the mol ratio of epoxy double-seal head agent are 100~150：30~50；
The structural formula such as formula (II) of the oligomeric cyclosiloxane of olefin-containing base, formula (III), formula (IV) described in the step (1)
Or shown in formula (V),
In formula (II) formula (II), formula (III), formula (IV) and formula (V), the R5For C2~C4 alkylene, preferably second
Alkenyl or acrylic, more preferably vinyl, R6Alkyl or unsaturated aromatic hydrocarbon base for C1~C3, preferably R6For methyl or
Phenyl, further preferred R6For phenyl, n is the integer between the integer between 5~20, preferably 5~10；
Acid catalyst in the step (1) is strong protonic acid (such as Emathlite, trifluoromethanesulfonic acid) or acid cation
Resin, preferably acidic cationic resin；
It is preferred that catalyst is in 80 DEG C of dryings in the step (1)；
It is preferred that oligomeric cyclosiloxane is in 80 DEG C of dehydrations in the step (1)；
Epoxy double-seal head agent in the step (2) is the structure shown in formula (VI),
R in formula (II)1, R2, R3, R4For C1~C3 alkyl, methyl is preferably all；
Purified it is preferred that also including step (3) after the step (2)：The product of step (2) is cooled to room temperature, and vacuum
Suction filtration removes catalyst, obtains the liquid of clear；Rotary evaporation removes low-boiling-point substance under 120~150 DEG C of vacuum conditions,
It can obtain the end epoxy silicon oil of the present invention.
The vacuum of the vacuum condition is -0.098MPa；
It is preferred that the step (3) is in 150 DEG C of rotary evaporations；
The present invention end epoxy silicon oil can as add-on type liquid silicon rubber adhesion promoters application.
The end epoxy silicon oil clear of the present invention, enters after additional organosilicon system as adhesion promoters addition
Compatibility is fabulous, does not interfere with the light transmittance after silicon rubber solidification；Bond activity high, add-on type can be just realized at 60 DEG C
Liquid silastic breaks bonding to the body of the base materials such as glass, PC and PMMA；Not only ring is contained at two ends to the end epoxy silicon oil of the present invention
Oxygen groups, the structure that can be chemically crosslinked solidifies into organic silicon rubber system, also contains vinyl, can be with organic silicon rubber body
Hydrosilylation occurs for the reactive hydrogen in system, and with extraordinary stability and reliability, even being subjected to 1000h height
After the high deterioration with moisture of temperature, preferable adhesive effect can also be also kept.
The present invention realizes that the ring-opening polymerisation polymerization of t etram-ethyltetravinylcyclotetrasiloxane is anti-under acid catalyst effect
Should, side reaction is few, and technique is simple, mild condition, it is easy to accomplish industrialized production；Product colorless and odorless, storage stability are more existing
There is adhesive accelerant good, up to more than 12 months.
Embodiment
With reference to embodiment, the present invention and its advantage are described in further detail, but the implementation of the present invention
Mode not limited to this.
A is the oligomeric cyclosiloxane of olefin-containing, and structural formula is R5For
C2~C4 alkylene, R6Alkyl or unsaturated aromatic hydrocarbon base for C1~C3, wherein A-1 are the silica of trimethyl triethylene basic ring three
Alkane；A-2 is t etram-ethyltetravinylcyclotetrasiloxane；A-3 is the vinyl D5 of pentamethyl five；A-4 is hexamethyl six
The siloxanes of ethene basic ring six.
B is epoxy double-seal head agent, and wherein B-1 is 1,3- bis- (3- glycidylpropyls) -1, the silica of 1,3,3- tetramethyl two
Alkane, B-2 is the tetraethyl disiloxane of 1,3- bis- (3- glycidylpropyls) -1,1,3,3-.
C is acid catalyst, and C-1 is acidic cationic resin.
A ' -1 is octamethylcy-clotetrasiloxane, and A ' -2 is octaphenylcyclotetrasiloxane.
C ' -1 is TMAH (TMAH).
R in A5For acrylic, R6When can be for ethyl, propyl group or phenyl, the end epoxy silicon oil of the present invention can be also synthesized, is made
It is suitable with effect of the embodiment of the present invention for adhesion promoters Use Limitation fruit.Acidic catalyst can be also strong protonic acid (such as acidity
Carclazyte, trifluoromethanesulfonic acid).The agent of epoxy double-seal head can also be the silicon of 1,3- bis- (3- glycidylpropyls) -1,1,3,3- tetrapropyls two
Oxygen alkane.
End epoxy silicon oil method of testing prepared by embodiment is as follows, and test result is shown in Table 2：
(1) viscosity test is according to GB/T 2794-1995《The measure of adhesive viscosity》Perform；
(2) contents of ethylene：Titration test is carried out using iodimetric titration；
(3) smell：Sample bottle cap is opened, is smelt with one's nose；
(4) storage stability：It is put into PET bottle and stands at 25 DEG C；
(5) it is infrared：Using KBr pressed disc method sample preparations, tested on infrared spectrometric analyzer, scanning range 4000~
400cm-1, resolution ratio is 4cm-1, scanning times 32 times；
(6) hydrogen is composed：Sample CDCl3After dissolving, tested on Bruker AV300 NMRs, resolution ratio is
300MHz；
The method of testing that end epoxy silicon oil prepared by embodiment is used for after organosilicon systems：
The end epoxy silicon oil of the preparation of Example 1~10, comparative example 1, comparative example 1 ' and comparative example 2, by end ring oxygen silicon
Oil quality is well mixed, is poured onto smooth than being added to for 1.5 parts in 100 parts of add-on type liquid organic silicon rubber system
Cold curing is heating and curing after 20 minutes for 2 hours or 60 DEG C in mould, and sample a~j, control sample a, control sample is respectively prepared
A ' and control sample b ', each index is shown in Table 3.
(1) adhesive strength test is according to GB/T 7124-2008《Measure (the rigid material pair of adhesive tensile shear strength
Rigid material)》Perform.
(2) cubical contraction test is according to GB/T 24148.9-2014《Plastics unsaturated polyester resin (UP-R) the 9th
Point:Cumulative volume shrinkage determination》Perform.
(3) visible light transmissivity and mist degree test are according to ASTM D1003-61《Standard Test Methodfor
Haze and Luminous Transmittance of Transparent Plastics》(《Transparent plastic light transmittance and mist
Spend test method)》Perform.
(4) dielectric constant test is according to GB/T1693-2007《Vulcanize elastomeric dielectric constant and dielectric loss angle tangent
Assay method》Perform.
(5) heatproof moisture-proof reliability, thermal shock stability, high temperature and Low-Temperature Reliability test are according to GB/T2423.3-
2006《Electric and electronic product environmental test part 2 test method tests cab：Steady-state damp heat test》Perform.
Embodiment 1~10 and comparative example
(1) pretreatment of raw material：By catalyst in T124h is dried in vacuo at DEG C, fully to remove moisture, olefin-containing base it is low
In T in cyclo(poly)siloxane input reaction vessel2T is removed water under DEG C vacuum condition1h；
(2) ring-opening polymerization：High pure nitrogen is passed through into reaction vessel, and adds the agent of epoxy double-seal head and dried
Catalyst, is warming up to T3DEG C, react t2H, the oligomeric cyclosiloxane of olefin-containing base and the mol ratio of epoxy double-seal head agent be 100~
150：30~50；
(3) purify：The product of step (2) is cooled to room temperature, and is filtered by vacuum removing catalyst, clear is obtained
Liquid；Then at T4Rotary evaporation removing low-boiling-point substance under DEG C vacuum condition, you can obtain holding epoxy silicon oil.
Specific material proportion, reaction condition are shown in Table 1.
Embodiment (the unit of table 1：g)
The end epoxy silicon oil sample index of the embodiment of table 2 and comparative example
Note：+ refer to water white transparency；Zero refers to colorless and odorless, ● it is irritant smell.
The end epoxy silicon oil of Example 1 does infrared spectrum, (unlisted) analysis of spectrogram：788cm-1、1253cm-1、
1270cm-1Locate as Si-CH3Absworption peak；1087cm-1Locate the absworption peak for Si-O-Si；957cm-1、1408cm-1、1596cm-1
Locate as Si-CH=CH2Absworption peak；2945cm-1、2841cm-1Locate as CH2Absworption peak；841cm-1、1150cm-1、1339cm-1、1457cm-1Locate the absworption peak for epoxy radicals.
The end epoxy silicon oil of Example 1 does hydrogen spectrum, (unlisted) analysis of spectrogram：Chemical shift δ is at 5.8-5.9ppm
Characteristic peak be CH2=CH proton uptake peak, δ is the proton uptake peak that the characteristic peak at 5.9-6.1ppm is OH, and δ is
Characteristic peak at 2.6ppm, 2.8ppm and 3.1ppm is the proton uptake peak in epoxide group.
Composed with reference to hydrogen, the characteristic peak of infrared spectrum is analyzed, the end epoxy silicon oil structural formula of embodiment 1 is as follows：
The organic silicon rubber sample index of table 3
Note：+ refer to water white transparency；√ refers to place the corresponding time under corresponding conditionses and circulates what is measured after corresponding number of times
Qualified (the i.e. visible light transmissivity of performance indications>98%, the decline of adhesion strength is within 5%), × refer under corresponding conditionses
Place the performance indications measured after the corresponding time unqualified.
The present invention causes oligomeric cyclosiloxane open loop to be reacted with the agent of epoxy double-seal head by acid catalysis, has synthesized olefin-containing base
End epoxy silicon oil, for base catalyst, its colorless and odorless, storage stability is good.The end epoxy silicon oil clarification of the present invention is saturating
Bright, compatibility is fabulous after entering additional organosilicon system as adhesion promoters addition, does not interfere with silicon rubber and solidifies it
Light transmittance afterwards；Bond activity high, can just realize add-on type liquid silicon rubber to base materials such as glass, PC and PMMA at 60 DEG C
Body bonding, be subjected to after 1000h tropical deterioration, the decline of adhesion strength is within 5%.
Be not difficult to find out from table 3, sample a has used end epoxy silicon oil 1, its adhesion strength than control sample a and control sample a ' more preferably,
This is probably, due to holding oxygen-containing silicone oil 1 to contain vinyl, can occur hydrosilylation with the reactive hydrogen in organic silicon rubber system,
The end epoxy silicon oil that control sample a and control sample a ' are used does not contain vinyl, so poor to glass, PC and PMMA adhesive properties.
Claims (15)
1. a kind of end epoxy silicon oil, it is characterised in that shown in the end epoxy silicon oil general structure such as formula (I)：
R in formula (I)1、R2、R3、R4For C1~C3 alkyl；R5For C2~C4 alkylene, R6Alkyl or insatiable hunger for C1~C3
And aryl；N is the integer between 5~20.
2. epoxy silicon oil is held as claimed in claim 1, it is characterised in that the R1、R2、R3、R4It is methyl.
3. epoxy silicon oil is held as claimed in claim 1, it is characterised in that the R5For vinyl or acrylic.
4. epoxy silicon oil is held as claimed in claim 3, it is characterised in that the R5For vinyl.
5. end epoxy silicon oil as claimed in claim 4, it is characterised in that the vinyl mass content of the end epoxy silicon oil is
2~8%.
6. epoxy silicon oil is held as claimed in claim 1, it is characterised in that the R6For methyl or phenyl.
7. epoxy silicon oil is held as claimed in claim 1, it is characterised in that the n is 5~10 integer.
8. the end epoxy silicon oil as described in claim 1~7 Arbitrary Term, it is characterised in that the viscosity of the end epoxy silicon oil is
25~200mPas.
9. the preparation method of the end epoxy silicon oil described in claim 1, it is characterised in that comprise the following steps：
(1), pretreatment of raw material：By acid catalyst in being dried in vacuo at 60~90 DEG C, moisture is fully removed, by the low of olefin-containing base
Cyclo(poly)siloxane input reaction vessel under 80~120 DEG C of vacuum conditions remove water 1~3h, the oligomeric cyclosiloxane be six,
8th, ten or twelve-ring；
(2), ring-opening polymerization：Nitrogen is passed through into reaction vessel, and adds the agent of epoxy double-seal head and dried acid catalysis
Agent, is warming up to 60~90 DEG C, reacts 3~8h, you can obtain the end epoxy silicon oil of the present invention；The oligomeric cyclosiloxane, epoxy
The mol ratio of double-seal head agent is 100~150：30~50.
10. the preparation method of epoxy silicon oil is held as claimed in claim 9, it is characterised in that contain alkene described in the step (1)
The structural formula such as formula (II) of the oligomeric cyclosiloxane of alkyl, formula (III), shown in (IV) or formula (V),
In formula (II), (III), (IV) and (V), the R5For C2~C4 alkylene, R6Alkyl or unsaturated virtue for C1~C3
Alkyl, n is the integer between 5~20.
11. the preparation method of epoxy silicon oil is held as claimed in claim 10, it is characterised in that R5For vinyl.
12. the preparation method of epoxy silicon oil is held as claimed in claim 10, it is characterised in that the R6For methyl or phenyl.
13. the preparation method of epoxy silicon oil is held as claimed in claim 10, it is characterised in that the epoxy double-seal head agent structure
Shown in formula such as formula (VI),
。
14. the preparation method of epoxy silicon oil is held as claimed in claim 11, it is characterised in that also wrapped after the step (2)
Include step (3) purification：The product of step (2) is cooled to room temperature, and is filtered by vacuum removing catalyst, the liquid of clear is obtained
Body；Rotary evaporation removes low-boiling-point substance under 120~150 DEG C of vacuum conditions, obtains holding epoxy silicon oil.
15. the end epoxy silicon oil described in claim 1~9 Arbitrary Term is used as the adhesion promoters of add-on type liquid silicon rubber
On the way.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109486469A (en) * | 2018-10-31 | 2019-03-19 | 肇庆皓明有机硅材料有限公司 | Electric kettle seals organosilicon material and preparation method thereof with dual composition addition type |
| CN112940671A (en) * | 2021-03-03 | 2021-06-11 | 江苏科技大学 | Preparation method of organosilicon foam material with high flame retardant property |
| CN113861913A (en) * | 2021-09-27 | 2021-12-31 | 湖北晟特新材料有限公司 | High-thermal-conductivity eugenol modified epoxy resin pouring sealant and preparation method and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109486469A (en) * | 2018-10-31 | 2019-03-19 | 肇庆皓明有机硅材料有限公司 | Electric kettle seals organosilicon material and preparation method thereof with dual composition addition type |
| CN109486469B (en) * | 2018-10-31 | 2021-06-08 | 广东皓明有机硅材料有限公司 | Double-component addition type sealing organic silicon material for electric kettle and preparation method thereof |
| CN112940671A (en) * | 2021-03-03 | 2021-06-11 | 江苏科技大学 | Preparation method of organosilicon foam material with high flame retardant property |
| CN113861913A (en) * | 2021-09-27 | 2021-12-31 | 湖北晟特新材料有限公司 | High-thermal-conductivity eugenol modified epoxy resin pouring sealant and preparation method and application thereof |
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