CN109180718A - A kind of preparation method of peroxidating silane coupling agent - Google Patents
A kind of preparation method of peroxidating silane coupling agent Download PDFInfo
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- CN109180718A CN109180718A CN201810990461.6A CN201810990461A CN109180718A CN 109180718 A CN109180718 A CN 109180718A CN 201810990461 A CN201810990461 A CN 201810990461A CN 109180718 A CN109180718 A CN 109180718A
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Abstract
The present invention provides a kind of preparation methods of peroxidating silane coupling agent, the preparation method is first by 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, tetramethoxy-silicane, titanium tetrachloride are mixed with non-protonic solvent, then under the conditions of 0~5 DEG C of temperature, diisopropylcarbodiimide is added, it is finished to diisopropylcarbodiimide addition, control reaction temperature is 25~50 DEG C, and silicyl oxide coupling agent is obtained.The adition process of diisopropylcarbodiimide is controlled between 0~5 DEG C of temperature, it can promote the intermediate and 1 of above-mentioned transition state, the reaction of 1- diperoxy tertiary butyl-4-hydroxy hexamethylene, the intermediate self-rearrangement for reducing transition state generates the probability of by-product, thus it can greatly reduce the progress of side reaction, it to be also beneficial to improve reaction yield, is computed, yield of the present invention is 90~96%.
Description
Technical field
The invention belongs to silane coupling agent preparation technical fields, and in particular to a kind of preparation of peroxidating silane coupling agent
Method.
Background technique
Coupling agent will be used wider and wider general as " bridge " that improves inorganic material and organic material interface.Its
Middle silane coupling agent is one kind that current dosage is maximum, kind is most.Silane coupling agent be in the molecule have it is two or more not
With the organic silicon monomer of reactive group, it can be chemically bonded with organic with inorganic material, increase the bonding of two kinds of materials
Property.The general structure of silane coupling agent is RSiX3, X represents the alkoxy that can be hydrolyzed in formula, such as halogen, alkoxy, acyl-oxygen
Base etc., R represents the active function groups for having affinity or respond with polymer molecule, such as oxygroup, sulfydryl, vinyl, epoxy
Base, amide groups, aminopropyl etc..In recent years, since silane coupling agent is in inoganic particle modified and graft polymers use in conjunction pair
The modification of polymeric matrix achieves good effect, thus becomes the hot spot of research and development.
In order in inorganic material surface graft polymerization high polymer, usually first with the coupling agent containing vinyl and epoxy group
Inorganic material is surface-treated, unsaturated carbon-carbon double bond or epoxy group is introduced, is then added and causes on this basis
Agent and then initiation polymerization high polymer.Using, in its surface scion grafting polymer, being greatly improved while coupling agent coated inorganic particle
The compatibility of inorganic particulate and polymeric matrix, while also improving its comprehensive performance.
For example, prior art discloses a kind of preparation method of peroxidating silane coupling agent, preparation method is specifically included
Following steps: 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene and tetramethoxy-silicane are mixed and added into reaction kettle,
Toluene, which is added, makees solvent simultaneously, is stirred to react 3~48h under conditions of temperature is -10 DEG C~50 DEG C, product is mentioned by separation
After pure, peroxy-silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane are obtained.Above-mentioned preparation
The coupling agent that method is prepared, one end are hydrolyzable methoxy group, and the other end is the peroxy-radical that can cause polymerization,
It can be used in the association response of surface modifying inorganic particle and graft polymers, but the silane coupling agent yield in above-mentioned technology
It needs to be further improved.In consideration of it, how to improve the preparation method of existing peroxidating silane coupling agent to mention
High reaction yield, this is a technical problem urgently to be resolved to those skilled in the art.
Summary of the invention
Technical problem to be solved by the present invention lies in overcome the preparation method of existing peroxidating silane coupling agent to be deposited
The low defect of yield, and then provide a kind of preparation method of peroxidating silane coupling agent.
The present invention solves the technical solution that above-mentioned technical problem uses are as follows:
The first aspect of the present invention provides a kind of preparation method of peroxidating silane coupling agent, includes the following steps:
(1) by 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, tetramethoxy-silicane, titanium tetrachloride and aprotic
Solvent mixing；
(2) diisopropylcarbodiimide is added into the mixture of (1) under conditions of 0~5 DEG C in control temperature；
(3) after the completion of the step (2), controlled at 25~50 DEG C, peroxidating silane coupling agent is made in filtering.
In the preparation method of above-mentioned peroxidating silane coupling agent, 1, the 1- diperoxy tertiary butyl-4-hydroxy hexamethylene
Molar ratio with the tetramethoxy-silicane, the titanium tetrachloride, the diisopropylcarbodiimide is 1:(0.2~5.0):
(0.01~0.05): (0.5~1), preferably 1:2.5:0.02:0.8.
The non-protonic solvent is CHCl3、CH2Cl2Or CCl4One of or it is a variety of.
The preparation method of above-mentioned peroxidating silane coupling agent further includes that diisopropyl carbon two is sub- in the step (2)
Amine is dissolved in the non-protonic solvent, under stirring, is added dropwise in the mixture of step (1).
In the step (1), the preparation method of 1, the 1- diperoxy tertiary butyl-4-hydroxy hexamethylene includes as follows
Step:
The hydrogen peroxide tert-butyl alcohol is mixed with 4- hydroxy-cyclohexanone, and temperature is controlled at -10~20 DEG C, while stirring
Be added the concentrated sulfuric acid, after being added dropwise, continue -10~20 DEG C at a temperature of be stirred to react 4~10h, preferably 5~8h, obtain
1,1- diperoxy tert-butyl -4- hydroxycyclohexan is made through washing, filtering, drying in product.
The molar ratio of the hydrogen peroxide tert-butyl alcohol and the 4- hydroxy-cyclohexanone is 1:(2~10), preferably 1:(5~
8)。
Preferably, the concentration of the concentrated sulfuric acid is 98wt%.The mass parts of the hydrogen peroxide tert-butyl alcohol and the dense sulphur
The ratio between parts by volume of acid is (10~20): 1, preferably (12~18): 1；The mass parts and the parts by volume relationship are g/mL.
The preparation method of above-mentioned peroxidating silane coupling agent further includes by peroxide SiClx obtained in the step (3)
Alkane coupling agent carries out the step of purification process comprising:
Peroxidating silane coupling agent obtained is washed with the non-protonic solvent, filter cake is then dissolved in acetone
Volume ratio with water is (1~3): the volume ratio of the in the mixed solvent of (1~2), preferably acetone and water is 2:1.5, cooling analysis
Crystalline substance, the peroxidating silane coupling agent for filtering to purify.
The second aspect of the present invention provides the peroxidating that the preparation method of above-mentioned peroxidating silane coupling agent is prepared
Silane coupling agent.
Above-mentioned technical proposal of the invention has the advantages that
1, the preparation method of peroxidating silane coupling agent of the present invention, the preparation method is first by 1,1- diperoxy
Change tertiary butyl-4-hydroxy hexamethylene, tetramethoxy-silicane, titanium tetrachloride to mix with non-protonic solvent, then at 0~5 DEG C
Under the conditions of temperature, diisopropylcarbodiimide is added, is finished to diisopropylcarbodiimide addition, control reaction temperature is 25
~50 DEG C, silicyl oxide coupling agent is obtained.It is different to be added two in the presence of 0~5 DEG C of temperature and titanium tetrachloride by the present invention
Propyl carbodiimide, thus diisopropylcarbodiimide can form the intermediate of transition state, the transition state with tetramethoxy-silicane
Intermediate reacted with 1, the 1- diperoxy tertiary butyl-4-hydroxy hexamethylene in system, obtain required peroxide
Change silane coupling agent, the adition process of diisopropylcarbodiimide is controlled between 0~5 DEG C of temperature, can promote above-mentioned mistake
The intermediate and 1 of state is crossed, the reaction of 1- diperoxy tertiary butyl-4-hydroxy hexamethylene reduces the intermediate itself of transition state
The probability for generating by-product is reset, the progress of side reaction thus can be greatly reduced, to be also beneficial to improve reaction yield, warp
It calculates, yield of the present invention is 90~96%.
2, the preparation method of peroxidating silane coupling agent of the present invention further includes that will react obtained peroxide SiClx
Alkane coupling agent carries out the step of purification process: the reaction solution obtained after the reaction was completed being filtered, filter cake is molten with the aprotic
Filter cake is dissolved in the volume ratio of acetone and water then as (1~3) by agent washing: the in the mixed solvent of (1~2), cooling crystallization,
The peroxidating silane coupling agent for filtering to purify, it is rapid by purifying, the purity of product peroxidating silane coupling agent can be improved.
Specific embodiment
Technical solution of the present invention will be clearly and completely described below, it is clear that described embodiment is this
Invention a part of the embodiment, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art
Every other embodiment obtained without making creative work, shall fall within the protection scope of the present invention.This
Outside, technical characteristic involved in invention described below different embodiments is as long as they do not conflict with each other
It can be combined with each other.
Embodiment 1
The preparation method of peroxidating silane coupling agent provided in this embodiment includes the following steps:
(1) preparation of 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene
It with 4- hydroxy-cyclohexanone is in molar ratio that 1:2 is mixed, and is put into reaction stirred tank by the 10g hydrogen peroxide tert-butyl alcohol
In, control reaction temperature is 20 DEG C, and the concentrated sulfuric acid 1mL that concentration is 98wt% is added while stirring, after being added dropwise, is continued
It is stirred to react 4h at a temperature of 20 DEG C, the tertiary fourth of 1,1- diperoxy is made through washing, filtering, vacuum drying in obtained product
Base -4- hydroxycyclohexan, H spectrogram are as follows:1H NMR(600MHz,CDCl3, TMS): δ 3.81 (t, 1H, COH), 2.14
(s, 1H, CH), 1.81 (m, 4H, CHCH2CH2), 1.67 (s, 4H, CHCH2CH2), 1.24 (t, 18H, CCH3)；
(2) preparation of peroxidating silane coupling agent
Take 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, 5mol tetramethoxy-silicane made from 1mol step (1)
It is mixed with 0.01mol titanium tetrachloride, 100mLCHCl is added3, reaction system is formed, is then by the temperature control of reaction system
0 DEG C, and 1mol diisopropylcarbodiimide is added at this temperature, after addition, reacted controlled at 50 DEG C
Peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane is made in 10h, filtering；Through
It calculates, the yield of the present embodiment is 90%；
(3) it refines
By peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy obtained above
Silane CHCl3Washing, the in the mixed solvent for being then 1:2 by the volume ratio that filter cake is dissolved in acetone and water, cooling crystallization,
The peroxidating silane coupling agent for filtering to purify.
It is detected through HPLC, 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the present embodiment
Purity be 96%.
The structural formula of 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the present embodiment is such as
Under:
Its H spectrogram is as follows:1H NMR(600MHz,CDCl3,TMS):δ3.58(t,9H,OCH3), 2. 13 (s, 1H, CH),
1.81(m,4H,CHCH2CH2), 1.67 (s, 4H, CHCH2CH2), 1.24 (t, 18H, C CH3)。
Embodiment 2
The preparation method of peroxidating silane coupling agent provided in this embodiment includes the following steps:
(1) preparation of 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene
It with 4- hydroxy-cyclohexanone is in molar ratio that 1:10 is mixed, and is put into reaction stirred tank by the 10g hydrogen peroxide tert-butyl alcohol
In, control reaction temperature is -10 DEG C, and the concentrated sulfuric acid 0.5mL that concentration is 98wt% is added while stirring, after being added dropwise, is continued
- 10 DEG C at a temperature of be stirred to react 10h, 1,1- diperoxy uncle is made through washing, filtering, vacuum drying in obtained product
Butyl -4- hydroxycyclohexan；
(2) preparation of peroxidating silane coupling agent
Take 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, 0.2mol tetramethoxy-silicane made from 1mol step (1)
Alkane is mixed with 0.05mol titanium tetrachloride, and 100mL CH is added2Cl2And CCl4Mixture, wherein CH2Cl2And CCl4Volume
It is then 5 DEG C by the temperature control of reaction system, and 0.5mol bis- is added at this temperature than forming reaction system for 1:1
Diisopropylcarbodiimide after addition, carries out reaction 8h controlled at 25 DEG C, and peroxidating silane coupling agent is made in filtering
1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane；It is computed, the yield of the present embodiment is 95%；
(3) it refines
By peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy obtained above
Silane CH2Cl2Washing, the in the mixed solvent for being then 3:1 by the volume ratio that filter cake is dissolved in acetone and water, cooling crystallization,
The peroxidating silane coupling agent for filtering to purify.
It is detected through HPLC, 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the present embodiment
Purity be 94%.
Embodiment 3
The preparation method of peroxidating silane coupling agent provided in this embodiment includes the following steps:
(1) preparation of 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene
It with 4- hydroxy-cyclohexanone is in molar ratio that 1:5 is mixed, and is put into reaction stirred tank by the 10g hydrogen peroxide tert-butyl alcohol
In, control reaction temperature is 0 DEG C, and the concentrated sulfuric acid 0.8mL that concentration is 98wt% is added while stirring, after being added dropwise, is continued
It is stirred to react 5h at a temperature of 0 DEG C, 1,1- diperoxy tert-butyl-is made through washing, filtering, vacuum drying in obtained product
4- hydroxycyclohexan；
(2) preparation of peroxidating silane coupling agent
Take 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, 2.5mol tetramethoxy-silicane made from 1mol step (1)
Alkane is mixed with 0.02mol titanium tetrachloride, and 100mL CH is added2Cl2Reaction system is formed, then controls the temperature of reaction system
It is 3 DEG C, and 0.8mol diisopropylcarbodiimide is added at this temperature, after addition, is carried out controlled at 30 DEG C anti-
9.5h is answered, is filtered, peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane is made；
It is computed, the yield of the present embodiment is 96%；
(3) it refines
By peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy obtained above
Silane CH2Cl2The volume ratio that filter cake is dissolved in acetone and water is then the in the mixed solvent of 2:1.5 by washing, cooling analysis
Crystalline substance, the peroxidating silane coupling agent for filtering to purify.
It is detected through HPLC, 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the present embodiment
Purity be 95%.
Embodiment 4
The preparation method of peroxidating silane coupling agent provided in this embodiment includes the following steps:
(1) preparation of 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene
It with 4- hydroxy-cyclohexanone is in molar ratio that 1:8 is mixed, and is put into reaction stirred tank by the 10g hydrogen peroxide tert-butyl alcohol
In, control reaction temperature is 5 DEG C, and the concentrated sulfuric acid 0.5mL that concentration is 98wt% is added while stirring, after being added dropwise, is continued
It is stirred to react 8h at a temperature of 5 DEG C, 1,1- diperoxy tert-butyl-is made through washing, filtering, vacuum drying in obtained product
4- hydroxycyclohexan；
(2) preparation of peroxidating silane coupling agent
Take 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, 0.9mol tetramethoxy-silicane made from 1mol step (1)
Alkane is mixed with 0.04mol titanium tetrachloride, and 100mL CH is added2Cl2Reaction system is formed, then controls the temperature of reaction system
It is 1 DEG C, and 0.6mol diisopropylcarbodiimide is added at this temperature, after addition, is carried out controlled at 40 DEG C anti-
9.5h is answered, is filtered, peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane is made；
It is computed, the yield of the present embodiment is 91%；
(3) it refines
By peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy obtained above
Silane CH2Cl2The volume ratio that filter cake is dissolved in acetone and water is then the in the mixed solvent of 1.5:1 by washing, cooling analysis
Crystalline substance, the peroxidating silane coupling agent for filtering to purify.
It is detected through HPLC, 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the present embodiment
Purity be 96%.
Embodiment 5
The preparation method of peroxidating silane coupling agent provided in this embodiment includes the following steps:
(1) preparation of 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene
It with 4- hydroxy-cyclohexanone is in molar ratio that 1:6 is mixed, and is put into reaction stirred tank by the 10g hydrogen peroxide tert-butyl alcohol
In, control reaction temperature is 15 DEG C, and the concentrated sulfuric acid 0.5mL that concentration is 98wt% is added while stirring, after being added dropwise, is continued
15 DEG C at a temperature of be stirred to react 7h, the tertiary fourth of 1,1- diperoxy is made through washing, filtering, vacuum drying in obtained product
Base -4- hydroxycyclohexan；
(2) preparation of peroxidating silane coupling agent
Take 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, 0.2mol tetramethoxy-silicane made from 1mol step (1)
Alkane is mixed with 0.01mol titanium tetrachloride, and 130mL CH is added2Cl2Reaction system is formed, then controls the temperature of reaction system
It is 1 DEG C, and 0.5mol diisopropylcarbodiimide is added at this temperature, after addition, is carried out controlled at 45 DEG C anti-
9.5h is answered, is filtered, peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane is made；
It is computed, the yield of the present embodiment is 92%；
(3) it refines
By peroxidating silane coupling agent 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy obtained above
Silane CH2Cl2Washing, the in the mixed solvent for being then 1:1 by the volume ratio that filter cake is dissolved in acetone and water, cooling crystallization,
The peroxidating silane coupling agent for filtering to purify.
It is detected through HPLC, 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the present embodiment
Purity be 96%.
Comparative example 1
It is in molar ratio that 1:1.2 is added instead by 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene and tetramethoxy-silicane
It answers in kettle, is stirred to react 10h under conditions of temperature is 10 DEG C, product obtains peroxy-silane coupling agent after separating-purifying
1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane.It is computed, peroxy-silane made from this comparative example is even
The yield for joining agent is 66%.
It is detected through HPLC, the purity of peroxy-silane coupling agent made from this comparative example is 79%.
Experimental example 1
By 1,1- diperoxy tertiary butyl-4-hydroxy cyclohexyl trimethoxy silane made from the embodiment of the present invention 1 with receive
Rice TiO2It is added in dimethyl sulfoxide for 1:20 in mass ratio, 10min is mixed, acrylonitrile is then added, is warming up to 70
DEG C stirring polymerization 6h, obtain modified-high polymer nano-TiO2.Grafting efficiency is 37%,.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.
For those of ordinary skill in the art, other various forms of changes can also be made on the basis of the above description
Change or changes.There is no necessity and possibility to exhaust all the enbodiments.And obvious change extended from this
Change or changes still within the protection scope of the invention.
Claims (10)
1. a kind of preparation method of peroxidating silane coupling agent, which comprises the steps of:
(1) by 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene, tetramethoxy-silicane, titanium tetrachloride and non-protonic solvent
Mixing；
(2) diisopropylcarbodiimide is added into the mixture of (1) under conditions of 0~5 DEG C in control temperature；
(3) after the completion of the step (2), controlled at 25~50 DEG C, peroxidating silane coupling agent is made in filtering.
2. the preparation method of peroxidating silane coupling agent according to claim 1, which is characterized in that 1, the 1- diperoxy
Change tertiary butyl-4-hydroxy hexamethylene and the tetramethoxy-silicane, the titanium tetrachloride, the diisopropylcarbodiimide are rubbed
You are than being 1:(0.2~5.0): (0.01~0.05): (0.5~1).
3. the preparation method of peroxidating silane coupling agent according to claim 1 or 2, which is characterized in that described non-proton
Property solvent be CHCl3、CH2Cl2Or CCl4One of or it is a variety of.
4. the preparation method of peroxidating silane coupling agent according to claim 1, which is characterized in that in the step (2),
Further include that diisopropylcarbodiimide is dissolved in the non-protonic solvent, under stirring, the mixed of step (1) is added dropwise
It closes in object.
5. the preparation method of peroxidating silane coupling agent according to claim 1, which is characterized in that in the step (1),
The preparation method of the 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene includes the following steps:
The hydrogen peroxide tert-butyl alcohol is mixed with 4- hydroxy-cyclohexanone, and temperature is controlled at -10~20 DEG C, is added while stirring dense
Sulfuric acid, after being added dropwise, continue -10~20 DEG C at a temperature of be stirred to react 4~10h, obtained product through washing, filtering,
It is dry, 1,1- diperoxy tertiary butyl-4-hydroxy hexamethylene is made.
6. the preparation method of peroxidating silane coupling agent according to claim 5, which is characterized in that the hydrogen peroxide uncle
The molar ratio of butanol and the 4- hydroxy-cyclohexanone is 1:(2~10).
7. the preparation method of peroxidating silane coupling agent according to claim 5 or 6, which is characterized in that the concentrated sulfuric acid
Concentration be 98wt%.
8. the preparation method of peroxidating silane coupling agent according to claim 7, which is characterized in that the hydrogen peroxide uncle
The ratio between the mass parts of butanol and the parts by volume of the concentrated sulfuric acid are (10~20): 1；
The mass parts and the parts by volume relationship are g/mL.
9. the preparation method of peroxidating silane coupling agent according to claim 1, which is characterized in that in the step (3),
Further include the steps that peroxidating silane coupling agent obtained carrying out purification process comprising:
Peroxidating silane coupling agent obtained is washed with the non-protonic solvent, filter cake is then dissolved in acetone and water
Volume ratio is (1~3): the in the mixed solvent of (1~2), cooling crystallization, the peroxidating silane coupling agent for filtering to purify.
10. a kind of peroxide that the preparation method by peroxidating silane coupling agent according to any one of claims 1 to 9 is prepared
Change silane coupling agent.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478920A (en) * | 2015-01-04 | 2015-04-01 | 齐齐哈尔大学 | Peroxy-silane coupling agents and preparation method thereof |
| WO2016181678A1 (en) * | 2015-05-14 | 2016-11-17 | Ｊｘエネルギー株式会社 | Silane coupling agent, sealing agent composition, adhesive composition, rubber composition and tire |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478920A (en) * | 2015-01-04 | 2015-04-01 | 齐齐哈尔大学 | Peroxy-silane coupling agents and preparation method thereof |
| WO2016181678A1 (en) * | 2015-05-14 | 2016-11-17 | Ｊｘエネルギー株式会社 | Silane coupling agent, sealing agent composition, adhesive composition, rubber composition and tire |
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