CN111187415A - Multifunctional chain extender for addition type liquid silicone rubber and preparation method thereof - Google Patents
Multifunctional chain extender for addition type liquid silicone rubber and preparation method thereof Download PDFInfo
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- CN111187415A CN111187415A CN201910503678.4A CN201910503678A CN111187415A CN 111187415 A CN111187415 A CN 111187415A CN 201910503678 A CN201910503678 A CN 201910503678A CN 111187415 A CN111187415 A CN 111187415A
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- chain extender
- type liquid
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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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
- C08G77/52—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
Abstract
The invention belongs to the technical field of addition type liquid silicone rubber, and relates to a multifunctional chain extender for addition type liquid silicone rubber and a preparation method thereof. In addition, the acrylate structure can form a carbonization layer during combustion degradation, thereby improving the flame retardant property.
Description
Technical Field
The invention belongs to the technical field of addition type liquid silicone rubber, and relates to a multifunctional chain extender for addition type liquid silicone rubber and a preparation method thereof.
Background
Compared with condensed liquid silicone rubber, the addition type liquid silicone rubber has the advantages of no by-product generated in the vulcanization process, extremely small shrinkage rate, capability of deep vulcanization, small catalyst consumption, high monomer conversion rate, easily controlled crosslinking density and vulcanization speed and excellent comprehensive performance. In addition, the addition type liquid silicone rubber also has the advantages of excellent electrical insulation performance, aging resistance, high mechanical strength, good elasticity, quick and convenient molding, no toxicity, no odor, wider use temperature, safety, sanitation, strong product extensibility and the like, and can be prepared into serialized and differentiated products with different forms and different purposes. The composite material is widely applied to the fields of electronic and electrical equipment element encapsulation or encapsulation, medical materials, impression materials, daily chemical industry, sports health care, automobile shock absorption and the like. Meanwhile, with the progress of science and technology, more and more new technologies, new products and new applications also put higher requirements on the performance of the silicon rubber.
Polysiloxane molecular chains of the addition type liquid silicone rubber are connected into macromolecules with a three-dimensional network structure through hydrosilylation reaction to form crosslinking. The main cross-linking agent is hydrogen-containing silicone oil, the structure of which determines the type and the cross-linking density of cross-linking bonds, and the cross-linking agent has a decisive influence on the performance of the silicone rubber product.
In order to further improve the performance of addition type liquid silicone rubber, the end hydrogen-containing silicone oil is introduced into a formula system, which can improve the toughness of the rubber, and improve the tensile strength, the elongation at break and the like. Chinese patent CN104448839B discloses an addition type liquid silicone rubber and a preparation method thereof, wherein hydrogen-containing silicone oil containing at least 3 Si-H in each molecule is used as a cross-linking agent, and terminal hydrogen-containing silicone oil is used as a chain extender, so that molecular chain growth and cross-linking are realized, and further the processing and application performance of products are improved. However, the chain extender end hydrogen-containing silicone oil only plays a role in improving crosslinking, mechanical properties and other aspects in a system, other functions such as heat resistance, adhesive property, flame retardant property and the like are not improved, and the multifunctional chain extender for the addition type liquid silicone rubber is not available in the market at present.
Disclosure of Invention
The invention aims to provide a multifunctional chain extender for addition type liquid silicone rubber, which can improve the heat resistance, the adhesive property and the flame retardant property, and a preparation method thereof, aiming at solving the defect that the heat resistance, the adhesive property and the flame retardant property of the existing addition type liquid silicone rubber are not improved.
In order to achieve the purpose, the invention adopts the following technical scheme:
a multifunctional chain extender for addition type liquid silicone rubber is disclosed, wherein the general structural formula of the chain extender is as follows:
satisfying a viscosity of 100-2000 mPa.s. In the technical scheme, phenyl and esterification are introduced into the chain extender molecule and are used for an addition type liquid silicone rubber system, the phenyl can improve the heat resistance, and the ester group can improve the adhesive property of the rubber to a base material. In addition, the acrylate structure can form a carbonization layer during combustion degradation, thereby improving the flame retardant property.
The heat resistance promotion principle is as follows: the silicone rubber has different main chain structures and different heat resistance. The high temperature degradation products of silicone rubber are mainly some cyclic oligomers, such as hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane. The introduction of the multifunctional chain extender is equivalent to the introduction of phenyl, phenyl and the like on the main chain of the silicon rubber, so that the cyclization degradation reaction can be inhibited, and the heat resistance of the silicon rubber is greatly improved.
The adhesive property is improved: the chain extender contains ester groups, and the ester groups are combined with the hydroxyl on the surface of the base material more tightly under the action of chemical bonds and hydrogen bonds, so that the adhesive property of the adhesive to the base material is improved.
The flame retardant property is improved: on one hand, the introduction of the phenyl can improve the oxygen index and the thermal decomposition temperature of the silicon rubber, and the increase of the content of the phenyl chain links is beneficial to improving the carbon forming amount of the silicon rubber in the combustion process, thereby improving the flame retardant property.
On the other hand, the acrylic ester structure can also form a carbonization layer during combustion degradation, and the flame retardant property is improved.
Preferably, the chain extender comprises the following raw materials in parts by weight: 10-15 parts of methyl phenyl dichlorosilane, 3-5 parts of methanol, 25-35 parts of acrylic glycol monomer, 0.2-0.5 part of titanate catalyst, 0.2-0.5 part of p-methoxyphenol, 200 parts of hydrogen-terminated silicone oil and 0.08-0.1 part of platinum catalyst.
Preferably, the acrylic glycol ester monomer is one or more of 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate.
Preferably, the titanate catalyst is one or more of tetraisopropyl titanate, tetraisobutyl titanate and titanium complex.
Preferably, the structural general formula of the terminal hydrogen-containing silicone oil is (HMe)2)Si(Me2SiO)nSi(Me2H) And the viscosity is 100-1000 mPa.s.
Preferably, the platinum catalyst is any one of chloroplatinic acid, chloroplatinic acid-isopropanol complex, chloroplatinic acid-divinyltetramethyldisiloxane complex or a combination thereof.
A preparation method of a multifunctional chain extender for addition type liquid silicone rubber comprises the following steps:
(1): reacting methyl phenyl dichlorosilane with methanol to remove chlorine to obtain methyl phenyl dimethoxysilane;
(2): adding the methyl phenyl dimethoxysilane, the acrylic acid glycol ester monomer, the titanate catalyst and p-methoxyphenol obtained in the step (1) into a flask, vacuumizing, stirring for reaction, and removing generated methanol;
(3): diluting the reaction product obtained in the step (2) with toluene; washing with tartaric acid solution twice, washing with sodium bicarbonate solution 3 times, washing with water, washing with saturated saline water, and removing water layer; the organic phase obtained is treated with Na2SO4Further drying to obtain a dried product, and finally removing the residual toluene by decompression;
(4): and (4) taking the product obtained in the step (3), hydrogen-containing silicone oil and a platinum catalyst, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
Preferably, the temperature at which the vacuum is drawn in step (2) is 30 to 50 ℃.
Preferably, the tartaric acid solution accounts for 3-5% by mass and the sodium bicarbonate solution accounts for 3-5% by mass in the step (3).
Compared with the existing chain extender with hydrogen-terminated end, the invention has the characteristics that phenyl and ester groups are introduced into the chain extender molecule and are used for an addition type liquid silicone rubber system, the phenyl can improve the heat resistance, and the ester group can improve the adhesive property of the rubber to a base material. In addition, the acrylate structure can form a carbonization layer during combustion degradation, thereby improving the flame retardant property.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
100g of methylphenyldichlorosilane are reacted with 40g of methanol, and hydrogen chloride and excess methanol are removed to obtain methylphenyldimethoxysilane for use.
Example 1
Adding 10g of methyl phenyl dimethoxy silane, 25g of dihydroxy ethyl acrylate, 0.3g of titanate tetraisopropyl ester and 0.25g of p-methoxyphenol into a 100mL flask, vacuumizing at 40 ℃, stirring for reaction, and removing generated methanol; diluting the reaction product with toluene; then, the mixture was washed twice with a 5% tartaric acid solution, 3 times with a 5% sodium bicarbonate solution, and finally washed with water and saturated brine, and the water layer was removed in each washing. The organic phase obtained is treated with Na2SO4Further drying to obtain a dried product, and finally removing the residual toluene under reduced pressure to obtain a yield of 78%.
Taking 15g of the reaction product, 100g of hydrogen-terminated silicone oil with the hydrogen content of 0.2 percent and 0.1g of chloroplatinic acid-divinyl tetramethyl disiloxane complex catalyst, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
Example 2
Adding 10g of methylphenyl dimethoxyAdding silane, 30g dihydroxypropyl acrylate, 0.35g titanate tetraisobutyl ester and 0.3g p-methoxyphenol into a 100mL flask, vacuumizing at 35 ℃, stirring for reaction, and removing generated methanol; diluting the reaction product with toluene; then washed twice with 3% tartaric acid solution, 3 times with 3% sodium bicarbonate solution, and finally washed with water and saturated brine, with the water layer removed each time. The organic phase obtained is treated with Na2SO4Further drying to obtain dried product, and removing residual toluene under reduced pressure. The yield thereof was found to be 75%.
Taking 15g of the reaction product, 200g of hydrogen-terminated silicone oil with the hydrogen content of 0.1 percent and 0.1g of chloroplatinic acid catalyst, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
Example 3
Adding 10g of methyl phenyl dimethoxy silane, 30g of dihydroxypropyl acrylate, 0.2g of titanate tetraisobutyl ester and 0.35g of p-methoxyphenol into a 100mL flask, vacuumizing at 50 ℃, stirring for reaction, and removing generated methanol; diluting the reaction product with toluene; then washed twice with 4% tartaric acid solution, 3 times with 4% sodium bicarbonate solution, and finally washed with water and saturated brine, with the water layer removed each time. The organic phase obtained is treated with Na2SO4Further drying to obtain a dried product, and finally removing the residual toluene under reduced pressure to obtain a yield of 70%.
Taking 15g of the reaction product, 200g of hydrogen-terminated silicone oil with the hydrogen content of 0.15 percent and 0.08g of chloroplatinic acid-isopropanol complex catalyst, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
Example 4
Adding 12g of methyl phenyl dimethoxy silane, 25g of dihydroxypropyl acrylate, 0.5g of titanate tetraisobutyl ester and 0.5g of p-methoxyphenol into a 100mL flask, vacuumizing at 50 ℃, stirring for reaction, and removing generated methanol; diluting the reaction product with toluene; then washed twice with 4% tartaric acid solution, 3 times with 4% sodium bicarbonate solution, and finally washed with water and saturated brine, with the water layer removed each time. The obtained organic matterNa for phase2SO4Further drying to obtain a dried product, and finally removing the residual toluene under reduced pressure to obtain a yield of 70%.
Taking 15g of the reaction product, 200g of hydrogen-terminated silicone oil with the hydrogen content of 0.15%, 0.04g of chloroplatinic acid-isopropanol complex and 0.04g of chloroplatinic acid-divinyl tetramethyl disiloxane complex as catalysts, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
Example 5
Adding 15g of methyl phenyl dimethoxy silane, 35g of dihydroxypropyl acrylate, 0.2g of titanate tetraisobutyl ester and 0.2g of p-methoxyphenol into a 100mL flask, vacuumizing at 30 ℃, stirring for reaction, and removing generated methanol; diluting the reaction product with toluene; then washed twice with 4% tartaric acid solution, 3 times with 4% sodium bicarbonate solution, and finally washed with water and saturated brine, with the water layer removed each time. The organic phase obtained is treated with Na2SO4Further drying to obtain a dried product, and finally removing the residual toluene under reduced pressure to obtain a yield of 70%.
Taking 15g of the reaction product, 150g of hydrogen-terminated silicone oil with the hydrogen content of 0.15%, 0.05g of chloroplatinic acid-isopropanol complex and 0.04g of chloroplatinic acid as catalysts, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
The above-described embodiments are intended to illustrate rather than to limit the invention, and any modifications and variations of the present invention are within the scope of the claims of the present invention.
Claims (9)
1. The multifunctional chain extender for the addition type liquid silicone rubber is characterized in that the general structural formula of the chain extender is as follows:
satisfying viscosity of 100-2000 mPas.
2. The multifunctional chain extender for the addition type liquid silicone rubber as claimed in claim 1, wherein the chain extender comprises the following raw materials in parts by weight: 10-15 parts of methyl phenyl dichlorosilane, 3-5 parts of methanol, 25-35 parts of acrylic glycol monomer, 0.2-0.5 part of titanate catalyst, 0.2-0.5 part of p-methoxyphenol, 200 parts of hydrogen-terminated silicone oil and 0.08-0.1 part of platinum catalyst.
3. The multifunctional chain extender for the addition type liquid silicone rubber according to claim 2, wherein the acrylic glycol ester monomer is one or more of 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate.
4. The multifunctional chain extender as claimed in claim 2, wherein the titanate catalyst is one or more selected from tetraisopropyl titanate, tetraisobutyl titanate and titanium complex.
5. The multifunctional chain extender for the addition type liquid silicone rubber as claimed in claim 2, wherein the general structural formula of the hydrogen-terminated silicone oil is (HMe)2)Si(Me2SiO)nSi(Me2H) And the viscosity is 100-1000 mPa.s.
6. The multifunctional chain extender for the addition type liquid silicone rubber as claimed in claim 2, wherein the platinum catalyst is any one or combination of chloroplatinic acid, chloroplatinic acid-isopropanol complex, chloroplatinic acid-divinyltetramethyldisiloxane complex.
7. A method for preparing the multifunctional chain extender for addition type liquid silicone rubber according to claim 1, wherein the method comprises the following steps:
(1): reacting methyl phenyl dichlorosilane with methanol to remove chlorine to obtain methyl phenyl dimethoxysilane;
(2): adding the methyl phenyl dimethoxysilane, the acrylic acid glycol ester monomer, the titanate catalyst and p-methoxyphenol obtained in the step (1) into a flask, vacuumizing, stirring for reaction, and removing generated methanol;
(3): diluting the reaction product obtained in the step (2) with toluene; washing with tartaric acid solution twice, washing with sodium bicarbonate solution 3 times, washing with water, washing with saturated saline water, and removing water layer; the organic phase obtained is treated with Na2SO4Further drying to obtain a dried product, and finally removing the residual toluene by decompression;
(4): and (4) taking the product obtained in the step (3), hydrogen-containing silicone oil and a platinum catalyst, and reacting to obtain the multifunctional chain extender product for the addition type liquid silicone rubber.
8. The method for preparing the multifunctional chain extender for the addition type liquid silicone rubber according to claim 7, wherein the temperature of the vacuum pumping in the step (2) is 30-50 ℃.
9. The method for preparing the multifunctional chain extender for the addition type liquid silicone rubber according to claim 7, wherein the mass fraction of the tartaric acid solution in the step (3) is 3-5%, and the mass fraction of the sodium bicarbonate solution is 3-5%.
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Address after: 324000 No. 20 Huayin North Road, Quzhou City, Zhejiang Province, China Applicant after: Zhejiang Zhongtian Dongfang fluorosilicone Material Co.,Ltd. Address before: 324000 No. 20, Huayin North Road, Quzhou high tech Industrial Park, Quzhou District, Zhejiang Province Applicant before: ZHONGTIAN DONGFANG FLUORINE SILICON MATERIAL Co.,Ltd. |
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Application publication date: 20200522 |