CN105017536A - Acyloxy containing hydroxyalkyl polysiloxane and preparation method - Google Patents
Acyloxy containing hydroxyalkyl polysiloxane and preparation method Download PDFInfo
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- CN105017536A CN105017536A CN201510518216.1A CN201510518216A CN105017536A CN 105017536 A CN105017536 A CN 105017536A CN 201510518216 A CN201510518216 A CN 201510518216A CN 105017536 A CN105017536 A CN 105017536A
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Abstract
The invention relate to acyloxy containing hydroxyalkyl polysiloxane and a preparation method. The preparation method comprises steps as follows: hydrogen containing polysiloxane and a hydroxyalkyl acrylate or hydroxyalkyl methacrylate compound are taken as raw materials, a polymerization inhibitor is added, and a target product of acyloxy containing hydroxyalkyl polysiloxane is generated through the hydrosilylation reaction of silicon-hydrogen bonds and unsaturated double bonds under the action of a platinum catalyst at the reaction temperature of 80-145 DEG C; after the reaction, the unreacted hydroxyalkyl acrylate or hydroxyalkyl methacrylate compound is washed and removed with water, water and a solvent are removed through reduced pressure distillation, the polymerization inhibitor is removed through filtering, and the target product of acyloxy containing hydroxyalkyl polysiloxane is obtained. Acyloxy containing hydroxyalkyl polysiloxane prepared with the method contains active terminated hydroxyalkyl, and when acyloxy containing hydroxyalkyl polysiloxane is applied to preparation of high polymer materials such as modified polyacrylate and the like, the functional performance of modified siloxane-acrylate copolymers is improved.
Description
Technical field
The present invention relates to organo-siloxane synthesis technical field, particularly, relate to a kind of containing acyloxy hydroxyalkyl polysiloxane and preparation method.
Background technology
Polysiloxane is the macromolecular material containing Si-O-Si key on its macromolecular main chain.The bond distance that Si-O-Si key is longer and larger bond angle make its macromolecular chain have excellent kindliness and ventilation property, and high bond energy and the partial ionization characteristic of Si-O key make it have good resistance to elevated temperatures, and the side Si-CH on macromolecular main chain
3structure make it have extremely low surface tension and excellent water resistance, these numerous excellent properties make polysiloxane to apply in fields such as weaving, leather, papermaking, daily use chemicals, automobile, building, the energy, electronics, medicine and aerospace as silicone oil, silicone resin and silicone rubber products separately, also can be used as the intermediate feed of the macromolecular materials such as modified polyurethane, epoxy resin, polycarbonate and polyester.
Such as, by the condensation reaction of the group such as carboxyl, hydroxyl in the silicone hydroxyl in hydroxy-terminated polysiloxane and polyacrylic ester or polyethers, modification is carried out to them, but reaction generates the Si-O-C key of facile hydrolysis, silicone hydroxyl is regenerated after hydrolysis, cause molecule chain break, have a strong impact on the use properties of modified polyacrylic acid and polyethers.Thus, this is just in the urgent need to developing a kind of reactive polysiloxanes of novel texture, avoids the Si-O-C key forming facile hydrolysis when modification, to improve polymer-modified use properties.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of polysiloxane containing acyloxy hydroxyalkyl, can be used for the modification of the macromolecular materials such as polyacrylic ester, polyethers, urethane, avoid the formation of the Si-O-C key of facile hydrolysis, to improve polymer-modified use properties.
In addition, the invention still further relates to the preparation method containing acyloxy hydroxyalkyl polysiloxane.
The present invention's adopted technical scheme that solves the problem is: containing acyloxy hydroxyalkyl polysiloxane, its structural formula is:
Wherein, R
1for
cH
3, C
2h
5, C
6h
5or
in at least one, R
2for
cH
3, C
2h
5, C
6h
5in at least one, R
1, R
2in at least one be
r
3for H, CH
3in at least one, R
4for CH
2, C
2h
4, C
3h
6in at least one.
Compared with existing hydroxy-terminated polysiloxane, form Si-C key but not facile hydrolysis Si-O-C key containing during the polymkeric substance such as the polysiloxane-modified polyacrylic ester of acyloxy hydroxyalkyl, polyethers, urethane.And, of the present invention containing in acyloxy hydroxyalkyl polysiloxane contains hydroxyalkyl, its adjacent group contains the electron-withdrawing group of polarity---acyloxy, its hydroxyl is made to have suitable activity, can be further used for carrying out condensation reaction with the monomer or intermediate that contain carboxylic acid, hydroxyl or isocyanic ester, prepare the macromolecular materials such as polysiloxane-modified polyacrylic ester, polyethers, urethane.
A kind of preparation method containing acyloxy hydroxyalkyl polysiloxane, with hydrogen containing siloxane, hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds for raw material, add stopper, catalyst made from platonic, temperature of reaction is 80 ~ 145 DEG C, by the addition reaction of silicon with hydrogen of si-h bond and unsaturated double-bond, generate containing acyloxy hydroxyalkyl polysiloxane crude product, after having reacted, the washing unreacted hydroxyalkyl acrylate of removing or hydroxyalkyl methacrylate compounds, underpressure distillation dewaters again, excessively filters stopper and namely obtains containing acyloxy hydroxyalkyl polysiloxane.
Hydrogen containing siloxane of the present invention, hydroxyalkyl acrylate compounds and hydroxyalkyl methacrylate compounds are existing material.Preparation method of the present invention is raw materials used to be conveniently easy to get, and synthesis condition gentleness is not harsh.
Addition reaction of silicon with hydrogen of the present invention refers to compound containing Si-H key or polymkeric substance and under platinum catalyst effect, addition reaction occurs containing the compound of unsaturated link(age) or polymkeric substance, generates the class chemical reaction containing Si-C-structure silicoorganic compound or macromolecular material, addition reaction of silicon with hydrogen of the present invention specifically refers to that the unsaturated double-bond in Si-H key in hydrogen polysiloxanes and hydroxyalkyl acrylate class or hydroxyalkyl methacrylate compounds, under catalyst made from platonic effect, addition reaction occurs, generate containing Si-C bond structure containing acyloxy hydroxyalkyl polysiloxane, described stopper can suppress the autohemagglutination containing unsaturated double-bond monomer, with routine containing compared with the esters of acrylic acid of unsaturated link(age) or methyl acrylic ester compound, hydroxyalkyl acrylate class selected by the present invention or hydroxyalkyl methacrylate compounds are containing activated hydroxyalkyl, hydroxyalkyl is connected with the acyloxy with electron attraction, the hydroxyalkyl that gained is contained in acyloxy hydroxyalkyl polysilane has suitable activity.
In above-mentioned preparation method, the concrete structure of described hydrogen containing siloxane is such as formula I:
Wherein, 10≤m≤1000,0≤n≤100, R
5for H, CH
3, C
2h
5, C
6h
5,
in at least one, R
6for H, CH
3, C
2h
5or C
6h
5in at least one, and R
5, R
6in at least one is H.
In above-mentioned preparation method, the structural formula of described hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds is shown below respectively:
Wherein, R is worked as
7during for H, structure above represents hydroxyalkyl acrylate compound; Work as R
7for CH
3time, structure above represents hydroxyalkyl methacrylate compounds.
Further, hydroxyalkyl acrylate compounds is at least one in Hydroxyethyl acrylate, Propylene glycol monoacrylate, hy-droxybutyl, described hydroxyalkyl methacrylate compounds is at least one in hydroxyethyl methylacrylate, Rocryl 410, methacrylate
Further, reaction raw materials adds solvent, and the consumption of described solvent is 0 ~ 100% of reaction raw materials total mass.Solvent adds for diluting reaction thing, if reagent flow better does not then need to add solvent, if reactant comparatively thickness then need to add solvent and dilute.
As preferably, solvent load is 0 ~ 50% of reaction raw materials.
Further, solvent is at least one in benzene,toluene,xylene, dioxane, Virahol.
Further, in hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds, in unsaturated double-bond and hydrogen containing siloxane, the mol ratio of si-h bond is 1.0 ~ 3.0:1.0.
As preferably, in hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds, in unsaturated double-bond and hydrogen containing siloxane, the mol ratio of si-h bond is 1.0 ~ 2.0:1.0.
Further, stopper is Resorcinol, para benzoquinone, toluhydroquinone, 2-Tert. Butyl Hydroquinone, 2, at least one in 5-di-tert-butyl hydroquinone.
Further, the consumption of stopper is 0.01 ~ 5.0% of hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds quality.
As preferably, stopper consumption is 0.05 ~ 1.0% of hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds quality.
Further, catalyst made from platonic is at least one in Platinic chloride-ethanolic soln, Platinic chloride-aqueous isopropanol, Platinic chloride-vinylsiloxane complex compound, platinum dioxide.
Further, the consumption of catalyst made from platonic is 10 ~ 1 × 10
3ppm.The consumption of catalyst made from platonic calculates with the effective content of platinum.
As preferably, the consumption of catalyst made from platonic is 15 ~ 5 × 10
2ppm.The consumption of catalyst made from platonic calculates with the effective content of platinum.
To sum up, the invention has the beneficial effects as follows:
1, hydroxyalkyl is contained of the present invention containing in acyloxy hydroxyalkyl polysiloxane, its adjacent group contains the electron-withdrawing group-acyloxy of polarity, the hydroxyalkyl that gained is contained in acyloxy hydroxyalkyl polysilane has suitable activity, can with the radical reactions such as carboxyl, hydroxyl and isocyanate group.
2, preparation method of the present invention is raw materials usedly conveniently easy to get, synthesis condition gentleness is not harsh, is conducive to the industrialization production containing acyloxy hydroxyalkyl polysiloxane and business promotion application.
3, by preparation method of the present invention prepare containing the polysiloxane-modified monomer containing carboxyl or hydroxyl of acyloxy hydroxyalkyl or intermediate time, to avoid the formation of the Si-O-C key of facile hydrolysis, improve stability and the use properties of polysiloxane-modified polymkeric substance.
Accompanying drawing explanation
Fig. 1 is the reactant of embodiment 1 and the infared spectrum of product end acyloxy hydroxyethyl polysiloxane;
Fig. 2 is the infared spectrum of the product end acyloxy hydroxyethyl polysiloxane of embodiment 2;
Fig. 3 is the infared spectrum of the product end acyloxy hydroxypropyl polysiloxane of embodiment 3;
Fig. 4 is the infared spectrum of the product end acyloxy hydroxyl butyl polysiloxane of embodiment 4;
Fig. 5 is the infared spectrum of the product end acyloxy hydroxyethyl polysiloxane of embodiment 5;
Fig. 6 is the infared spectrum of the product end acyloxy hydroxypropyl polysiloxane of embodiment 6;
Fig. 7 is the infared spectrum of the product side acyloxy hydroxyethyl polysiloxane of embodiment 7;
Fig. 8 is the infared spectrum of the product end acyloxy hydroxyethyl polysiloxane of embodiment 8.
Embodiment
Below in conjunction with embodiment and accompanying drawing, to the detailed description further of invention do, but embodiments of the present invention are not limited thereto.
A kind of preparation method containing acyloxy hydroxyalkyl polysiloxane, with hydrogen containing siloxane, hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds for raw material, add stopper, catalyst made from platonic, temperature of reaction is 80 ~ 145 DEG C, by the addition reaction of silicon with hydrogen of si-h bond and unsaturated double-bond, generate containing acyloxy hydroxyalkyl polysiloxane crude product, after having reacted, the washing unreacted hydroxyalkyl acrylate of removing or hydroxyalkyl methacrylate compounds, underpressure distillation dewaters again, excessively filters stopper and namely obtains containing acyloxy hydroxyalkyl polysiloxane.
Embodiment 1:
100g end hydrogen containing siloxane, 11.6g Hydroxyethyl acrylate (C=C:Si-H mol ratio 1.0:1.0), 111.6g toluene (100% of reaction raw materials total mass), 0.58g Resorcinol (0.05% of Hydroxyethyl acrylate) is added, logical N in the 500mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 90 DEG C gradually, the 1wt% Platinic chloride-ethanolic soln (378ppm) adding 11.2g makes catalyzer, system rapid temperature increases, after system temperature is stable, is warming up to 95 DEG C of reaction 3h gradually, after reaction terminates, is down to room temperature, wash and remove unreacted Hydroxyethyl acrylate three times, heat up after dividing water refluxing toluene band water, is warming up to 100 DEG C subsequently, removed under reduced pressure toluene under-0.090MPa vacuum, be down to room temperature, filter to obtain end acyloxy hydroxyethyl polysiloxane.The infared spectrum of end hydrogen containing siloxane, Hydroxyethyl acrylate and end acyloxy hydroxyethyl polysiloxane as shown in Figure 1.In Fig. 1 (a) 2127.48 and 912.33cm
-1for the charateristic avsorption band of Si-H key in end hydrogen containing siloxane, 1024.20 and 1091.71cm
-1for the charateristic avsorption band of Si-O-Si key, 1261.45,864.11 and 800.46cm
-1for the charateristic avsorption band of Si-CH3 key; 1637.56cm in Fig. 1 (b)
-1and 3427.51cm
-1be respectively unsaturated C=C key and-CH in Hydroxyethyl acrylate
2cH
2in OH-charateristic avsorption band of OH; Can find from Fig. 1 (c): 2127.48 and 912.33cm
-1the charateristic avsorption band of place Si-H key disappears, at 3487.30cm
-1the charateristic avsorption band of place appearance-OH, simultaneously at 1637.56cm
-1the charateristic avsorption band locating unsaturated C=C disappears, and these show successfully to synthesize end acyloxy hydroxyethyl polysiloxane by end hydrogen containing siloxane and the addition reaction of silicon with hydrogen of Hydroxyethyl acrylate under chlorine catalyst action.
Embodiment 2
100g end hydrogen containing siloxane, 26.0g Propylene glycol monoacrylate (C=C:Si-H mol ratio 2.0:1.0), 63g dimethylbenzene (50% of reaction raw materials total mass), 0.003g Resorcinol (0.01% of Hydroxyethyl acrylate) is added, logical N in the 250mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 90 DEG C gradually, add the 1wt% Platinic chloride-aqueous isopropanol (10ppm) of 0.334g, system rapid temperature increases, after system temperature is stable, is warming up to 145 DEG C of reaction 5h gradually, after reaction terminates, is down to room temperature, wash the Propylene glycol monoacrylate that three removings are excessive, heat up after dividing water and dewater, be warming up to 100 DEG C subsequently, removed under reduced pressure dimethylbenzene under-0.090MPa vacuum, be down to room temperature, filter to obtain end acyloxy hydroxyethyl polysiloxane.The infared spectrum of end acyloxy hydroxyethyl polysiloxane as shown in Figure 2.
Embodiment 3
100g end hydrogen containing siloxane, 26.0g Propylene glycol monoacrylate (C=C:Si-H mol ratio 2.0:1.0), 0.26g Resorcinol (1% of Propylene glycol monoacrylate) is added, logical N in the 250mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 90 DEG C gradually, add the 1wt% Platinic chloride-aqueous isopropanol (1000ppm) of 33.46g, system rapid temperature increases, after system temperature is stable, is warming up to 100 DEG C of reaction 3h gradually, after reaction terminates, is down to room temperature, wash the Propylene glycol monoacrylate that three removings are excessive, add appropriate toluene intensification after dividing water to dewater, be warming up to 100 DEG C subsequently, removed under reduced pressure toluene under-0.090MPa vacuum, be down to room temperature, filter to obtain end acyloxy hydroxypropyl polysiloxane.The infared spectrum of end acyloxy hydroxypropyl polysiloxane as shown in Figure 3.
Embodiment 4
100g end hydrogen containing siloxane, 15.8g hy-droxybutyl (C=C:Si-H mol ratio 1.1:1.0), 50g benzene (43.2% of reaction raw materials total mass), 0.79g toluhydroquinone (5% of Propylene glycol monoacrylate) is added, logical N in the 250mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 80 DEG C gradually, the 1wt% Platinic chloride-vinylsiloxane complex compound (500ppm) adding 15.37g makes catalyzer, system rapid temperature increases, after system temperature is stable, be warming up to 80 DEG C of back flow reaction 5h gradually, after reaction terminates, be down to room temperature, wash the hy-droxybutyl that three removings are excessive, heat up after dividing water and dewater, be warming up to 100 DEG C subsequently, removed under reduced pressure benzene under-0.090MPa vacuum, be down to room temperature, filter to obtain end acyloxy hydroxyl butyl polysiloxane.The infared spectrum of end acyloxy hydroxyl butyl polysiloxane as shown in Figure 4.
Embodiment 5
100g end hydrogen containing siloxane, 26.0g hydroxyethyl methylacrylate (C=C:Si-H mol ratio 2.0:1.0), 63g dimethylbenzene (50% of reaction raw materials total mass), 0.003g 2 is added in the 250mL there-necked flask of thermometer, agitator and prolong, 5-di-tert-butyl hydroquinone (0.01% of hydroxyethyl methylacrylate), logical N
2replace three times, be warming up to 90 DEG C gradually, the 1wt% Platinic chloride-aqueous isopropanol (15ppm) adding 0.50g makes catalyzer, system rapid temperature increases, after system temperature is stable, is warming up to 145 DEG C of reaction 5h gradually.Be down to room temperature after reaction terminates, wash the hydroxyethyl methylacrylate that three removings are excessive, heating up after point water dewaters, and is warming up to 100 DEG C subsequently, removed under reduced pressure dimethylbenzene under-0.090MPa vacuum.Be down to room temperature, filter to obtain end acyloxy hydroxyethyl polysiloxane.The infared spectrum of end acyloxy hydroxyethyl polysiloxane as shown in Figure 5.
Embodiment 6
100g end hydrogen containing siloxane, 15.8g Rocryl 410 (C=C:Si-H mol ratio 1.1:1.0), 50g toluene (43.2% of reaction raw materials total mass), 0.2g para benzoquinone (1.26% of Rocryl 410) is added, logical N in the 250mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 90 DEG C gradually, the 1wt% Platinic chloride-aqueous isopropanol (41ppm) of 1.26g makes catalyzer, system rapid temperature increases, after system temperature is stable, be warming up to 110 DEG C of back flow reaction 5h gradually, after reaction terminates, be down to room temperature, wash the Rocryl 410 that three removings are excessive, heat up after dividing water refluxing toluene band water, is warming up to 100 DEG C subsequently, removed under reduced pressure toluene under-0.090MPa vacuum, be down to room temperature, filter to obtain end acyloxy hydroxypropyl polysiloxane.The infared spectrum of end acyloxy hydroxypropyl polysiloxane as shown in Figure 6.
Embodiment 7
50g side hydrogen containing siloxane, 12.8g Hydroxyethyl acrylate (C=C:Si-H mol ratio 1.1:1.0), 50g toluene (79.6% of reaction raw materials total mass), 0.2g 2-Tert. Butyl Hydroquinone (1.56% of Hydroxyethyl acrylate) is added, logical N in the 250mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 90 DEG C gradually, the platinum dioxide (137ppm) adding 0.01g makes catalyzer, system rapid temperature increases, after system temperature is stable, is warming up to 95 DEG C of reaction 5h gradually.Be down to room temperature after reaction terminates, wash the Hydroxyethyl acrylate that three removings are excessive, heat up after point water refluxing toluene band water, and be warming up to 100 DEG C subsequently, under-0.090MPa vacuum, removed under reduced pressure toluene, is down to room temperature, filters to obtain side acyloxy hydroxyethyl polysiloxane.The infared spectrum of side acyloxy hydroxyethyl polysiloxane as shown in Figure 7.
Embodiment 8
100g end hydrogen containing siloxane, 34.8g Hydroxyethyl acrylate (C=C:Si-H mol ratio 3.0:1.0), 0.58g Resorcinol (0.05% of Hydroxyethyl acrylate) is added, logical N in the 500mL there-necked flask of thermometer, agitator and prolong
2replace three times, be warming up to 90 DEG C gradually, the 1wt% Platinic chloride-ethanolic soln (378ppm) adding 11.2g makes catalyzer, system rapid temperature increases, after system temperature is stable, is warming up to 95 DEG C of reaction 3h gradually, after reaction terminates, is down to room temperature, wash and remove unreacted Hydroxyethyl acrylate three times, heat up after dividing water refluxing toluene band water, is warming up to 100 DEG C subsequently, removed under reduced pressure toluene under-0.090MPa vacuum, be down to room temperature, filter to obtain end acyloxy hydroxyethyl polysiloxane.The infared spectrum of end acyloxy hydroxyethyl polysiloxane as shown in Figure 8.
As mentioned above, the present invention can be realized preferably.
Claims (10)
1., containing acyloxy hydroxyalkyl polysiloxane, it is characterized in that, its structural formula is:
Wherein, R
1for
cH
3, C
2h
5, C
6h
5or
in at least one, R
2for
cH
3, C
2h
5, C
6h
5in at least one, R
1, R
2in at least one be
r
3for H, CH
3in at least one, R
4for CH
2, C
2h
4, C
3h
6in at least one.
2. one kind contains the preparation method of acyloxy hydroxyalkyl polysiloxane as claimed in claim 1, it is characterized in that, with hydrogen containing siloxane, hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds are raw material, add stopper, catalyst made from platonic, temperature of reaction is 80 ~ 145 DEG C, by the addition reaction of silicon with hydrogen of si-h bond and unsaturated double-bond, generate containing acyloxy hydroxyalkyl polysiloxane crude product, after having reacted, the washing unreacted hydroxyalkyl acrylate of removing or hydroxyalkyl methacrylate compounds, underpressure distillation dewaters again, cross and filter stopper and namely obtain containing acyloxy hydroxyalkyl polysiloxane.
3. the preparation method containing acyloxy hydroxyalkyl polysiloxane according to claim 2, it is characterized in that, described hydroxyalkyl acrylate compounds is at least one in Hydroxyethyl acrylate, Propylene glycol monoacrylate, hy-droxybutyl, described hydroxyalkyl methacrylate compounds is at least one in hydroxyethyl methylacrylate, Rocryl 410, methacrylate
4. the preparation method containing acyloxy hydroxyalkyl polysiloxane according to claim 2, it is characterized in that, reaction raw materials adds solvent, and the consumption of described solvent is 0 ~ 100% of reaction raw materials total mass.
5. the preparation method containing acyloxy hydroxyalkyl polysiloxane according to claim 4, it is characterized in that, described solvent is at least one in benzene,toluene,xylene, dioxane, Virahol.
6. the preparation method containing acyloxy hydroxyalkyl polysiloxane according to claim 2, it is characterized in that, in described hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds, in unsaturated double-bond and hydrogen containing siloxane, the mol ratio of si-h bond is 1.0 ~ 3.0:1.0.
7. the preparation method containing acyloxy hydroxyalkyl polysiloxane according to claim 2, it is characterized in that, described stopper is Resorcinol, para benzoquinone, toluhydroquinone, 2-Tert. Butyl Hydroquinone, 2, at least one in 5-di-tert-butyl hydroquinone.
8., according to the arbitrary described preparation method containing acyloxy hydroxyalkyl polysiloxane of claim 2 to 7, it is characterized in that, the consumption of described stopper is 0.01 ~ 5.0% of hydroxyalkyl acrylate or hydroxyalkyl methacrylate compounds quality.
9. according to the arbitrary described preparation method containing acyloxy hydroxyalkyl polysiloxane of claim 2 to 7, it is characterized in that, described catalyst made from platonic is at least one in Platinic chloride-ethanolic soln, Platinic chloride-aqueous isopropanol, Platinic chloride-vinylsiloxane complex compound, platinum dioxide.
10., according to the arbitrary described preparation method containing acyloxy hydroxyalkyl polysiloxane of claim 2 to 7, it is characterized in that, the consumption of described catalyst made from platonic is 10 ~ 1 × 10
3ppm.
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| CN112979957A (en) * | 2021-01-28 | 2021-06-18 | 深圳市安品有机硅材料有限公司 | Method for synthesizing hydroxyl polysiloxane |
| CN113999396A (en) * | 2021-10-29 | 2022-02-01 | 山东东岳有机硅材料股份有限公司 | Preparation method of epoxy modified polysiloxane photosensitive polymer |
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