CN107602861B - Water-based flame-retardant fluorine-containing silicone oil and preparation method thereof - Google Patents
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Abstract
The invention discloses water-based flame-retardant fluorine-containing silicone oil, which has the following chemical structure:
each R1Each independently is alkyl or aryl; r is a perfluoroalkyl group having 4 to 8 carbon atoms, and Q is an alkylene group having at least 2 carbon atoms; r2Is composed of
R3Is polyoxyethylene polyoxypropylene ether chain; r4Is aryl; r5Is an alkyl group. The material is obtained by copolymerizing the following raw materials in parts by weight: 20-82 parts of phenylcyclosiloxane, 20-90 parts of vinyl cyclosiloxane, 23-66 parts of alkyl cyclosiloxane, 40-200 parts of methyldimethoxysilane, 40-80 parts of fluoroolefin and 20-56 parts of allyl phosphate200-800 parts of monoallyl end-capped polyoxyethylene polyoxypropylene ether and 1-10 parts of end-capping agent. The water-based flame-retardant fluorine-containing silicone oil does not need an organic solvent, is green and environment-friendly, has a good flame-retardant effect and a good release effect, and can be applied to more fields.
Description
Technical Field
The invention belongs to the field of fluorine-containing silicone oil, and particularly relates to water-based flame-retardant fluorine-containing silicone oil and a preparation method thereof.
Background
The fluorine-containing polymer has the characteristics of lower surface free energy, super-strong weather resistance, excellent salt mist resistance, little pollution resistance and the like, and fluorine is introduced into organic silicon for the first time in the eighty years of the 20 th century. The fluorine-containing silicone oil is polysiloxane with a fluorine-containing alkyl side chain, and the unique molecular structure of the fluorine-containing silicone oil endows the fluorine-containing silicone oil with excellent high and low temperature resistance, excellent oxidation resistance, weather resistance and the like.
The fluorine-containing silicone oil is prepared by hydrolyzing chlorosilane containing fluoroalkyl and then carrying out ring-opening polymerization. In the process, a large amount of organic solvent is used, and the organic solvent is not beneficial to the environment and does not meet the requirement of green environmental protection. The developed water-based fluorine-silicon polymer generally adopts fluorine-containing olefin containing reactive double bond, organosilicon monomer, acrylic acid and ester thereof, and is polymerized by free radical solution, namely, firstly, fluorine-containing polymer is synthesized in organic solvent medium, and then the dissolved fluorine-containing polymer is made into water dispersion under the action of emulsifier or the water dispersion is directly prepared by free radical emulsion polymerization.
Currently, there are many types of flame retardants in practical use, and they can be classified into halogen-based, organic phosphorus-based, phosphorus-nitrogen-based (halogen-free intumescent flame retardants), organosilicon-based, and inorganic flame retardants. With the development of electrical appliances, electronics, machinery, automobiles, ships, aviation, aerospace and chemical engineering, the flame retardant requirement on product materials is higher and higher, so that the fluorine-containing silicone oil with lower surface free energy needs to be prepared and has a better flame retardant function.
Disclosure of Invention
The invention aims to overcome the defects of the existing silane modified resin and provides a silane modified polymer and a preparation method thereof.
In order to solve the technical problems, the invention provides the following technical scheme:
the water-based flame-retardant fluorine-containing silicone oil has the following chemical structure:
wherein x is 1-4000, y is 1-4000, z is 1-4000, w is 1-4000, v is 1-4000, and u is 1-4000;
each R1Each independently is alkyl or aryl;
r is a perfluoroalkyl group having 4 to 8 carbon atoms, and Q is an alkylene group having at least 2 carbon atoms;
R2is composed of
R3is-CH2CH2CH2O(C2H4O)m(C3H6O)nCH3or-CH2CH2CH2O(C2H4O)m(C3H6O)nH, wherein m is 0-100, n is 0-100, and m + n is more than or equal to 30;
R4is aryl; r5The alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, and the aryl group is a phenyl group (Ph), a p-methylphenyl group, an o-methylphenyl group, a 1-naphthyl group, a 2-naphthyl group or the like.
The water-based flame-retardant fluorine-containing silicone oil is prepared by copolymerizing the following raw materials in parts by weight:
preferably, the phenylcyclosiloxane is
Wherein a is 3-6, such as 2,4, 6-trimethyl-2, 4, 6-triphenylcyclotrisiloxane and 2,4,6, 8-tetramethyl-2, 4,6, 8-tetraphenylcyclotetrasiloxane.
Preferably, the vinyl cyclosiloxane is
Wherein b is 3 to 6, such as 2,4, 6-trivinyl-2, 4, 6-trimethylcyclotrisiloxane, tetramethyltetravinylcyclotetrasiloxane, pentamethylpentavinylcyclopentasiloxane, and hexamethylhexavinylcyclohexane hexasiloxane.
Preferably, the alkyl cyclosiloxane is
Wherein c is 3 to 6, R' is an alkyl group having 1 to 18 carbon atoms, and specific alkylcyclosiloxanes are hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
Preferably, it is characterized in that: the fluorine-containing olefin is R (CH)2)dCH＝CH2R is a perfluoroalkyl group having 4 to 8 carbon atoms, and d is 0 to 18.
Preferably, the allyl phosphate is dimethyl allyl phosphate or diethyl allyl phosphate.
Preferably, the monoallyl-terminated polyoxyethylene polyoxypropylene ether is CH2＝CHCH2O(C2H4O)m(C3H6O)nCH3Or CH2＝CHCH2O(C2H4O)m(C3H6O)nH, wherein m is 0-100, n is 0-100, and m + n is not less than 30.
Preferably, the end-capping agent is hexamethyldisiloxane.
The preparation method of the water-based flame-retardant fluorine-containing silicone oil comprises the following steps:
(1) mixing allyl phosphate, fluorine-containing olefin and methyldimethoxysilane, heating, and carrying out hydrosilylation reaction under the action of a catalyst to obtain a product A;
(2) mixing monoallyl-terminated polyoxyethylene polyoxypropylene ether with methyldimethoxysilane, heating, and carrying out hydrosilylation reaction under the action of a catalyst to obtain a product B;
(3) mixing the product A and the product B, and adding water for hydrolysis;
(4) and (3) mixing the hydrolysate obtained in the step (3) with phenyl cyclosiloxane, vinyl cyclosiloxane, alkyl cyclosiloxane and end-capping reagent, heating and carrying out copolymerization reaction to obtain the water-based flame-retardant fluorine-containing silicone oil.
The hydrosilylation reaction of the step (1) and the step (2) can be added with a catalytic amount of platinum catalyst, such as anti-poisoning Karstedt catalyst, Speier catalyst and the like, the temperature of the hydrosilylation reaction can be controlled to be 60-80 ℃, and the Karstedt catalyst with better anti-poisoning effect is preferably adopted as the catalyst.
A catalytic amount of an alkaline catalyst, such as potassium hydroxide, tetramethylammonium hydroxide, hexapyrrolidine diphosphonitril hydroxide and the like, can be added in the copolymerization reaction in the step (4), and the temperature of the copolymerization reaction can be controlled to be 60-80 ℃.
The water-based flame-retardant fluorine-containing silicone oil disclosed by the invention does not need an organic solvent, is soluble in water, does not need an organic solvent in a synthesis process, is green and environment-friendly, has a good flame-retardant effect and a good release effect, and widens the application of the fluorine-containing silicone oil in the field of coatings.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
FIG. 1 is an infrared spectrum of fluorosilicone oil prepared in example 1 of the present invention.
Detailed Description
The preferred embodiments of the present invention will be described in conjunction with the accompanying drawings, and it will be understood that they are described herein for the purpose of illustration and explanation and not limitation.
Example 1
50g of diethyl allylphosphate, 40g of perfluorobutylethylene and 0.5g of karstedt's catalyst were mixed, added dropwise to 100g of methyldimethoxysilane, heated to 70 ℃ and reacted for 5 hours with stirring.
200g of monoallyl-terminated polyoxyethylene polyoxypropylene ether (RHTJ-002M, Ningbo Runza Highestan materials science and technology Co., Ltd.) and 0.5g of karstedt catalyst were mixed, and added dropwise to 40g of methyldimethoxysilane, heated to 60 ℃ and stirred for 8 hours.
And mixing the products of the two steps, adding deionized water, stirring at room temperature for 3 hours, and filtering to remove unreacted micromolecules and water in the products.
The product obtained by the hydrolysis is mixed with 55g of 2,4,6, 8-tetramethyl-2, 4,6, 8-tetraphenylcyclotetrasiloxane, 89g of pentamethylpentavinylcyclopentasiloxane, 33g of octamethylcyclotetrasiloxane and 2g of hexamethyldisiloxane, 1.8g of potassium hydroxide is added to react for 8 hours at 70 ℃, the mixture is cooled, sodium bicarbonate and diatomite are added to be mixed, the mixture is stirred uniformly and then is filtered, and the filtrate is the target product.
Example 2
50g of dimethyl allylphosphate, 40g of perfluorobutylethylene and 0.5g of karstedt's catalyst were mixed, added dropwise to 100g of methyldimethoxysilane, heated, and reacted at 70 ℃ with stirring for 5 hours.
200g of monoallyl-terminated polyoxyethylene polyoxypropylene ether (RHTJ-002M, Ningbo Runza Highestan materials science and technology Co., Ltd.) and 0.5g of karstedt catalyst were mixed, added dropwise to 40g of methyldimethoxysilane, heated, and reacted at 60 ℃ for 8 hours with stirring.
And mixing the products of the two steps, adding deionized water, stirring at room temperature for 3 hours, and filtering to remove unreacted micromolecules and residual moisture in the products.
The product obtained by the above hydrolysis was mixed with 72g of pentamethylpentavinylcyclopentasiloxane, 82g of octamethylcyclotetrasiloxane, 20g of 2,4,6, 8-tetramethyl-2, 4,6, 8-tetraphenylcyclotetrasiloxane and 2g of hexamethyldisiloxane, and 1.5g of potassium hydroxide was added thereto to react at 70 ℃ for 8 hours. Cooling, adding sodium bicarbonate and diatomite, mixing, stirring uniformly, and performing suction filtration to obtain a filtrate as a target product.
Example 3
62g of diethyl allylphosphate, 35g of perfluorooctylethylene, 0.5g of the mixture and a Karstedt catalyst were mixed, and the mixture was added dropwise to 87g of methyldimethoxysilane, heated, and reacted at 70 ℃ for 5 hours with stirring.
352g of monoallyl-terminated polyoxyethylene polyoxypropylene ether (RHTJ-002M, Ningbo Runza Highestan materials science and technology Co., Ltd.) and 0.5g of karstedt catalyst were mixed, added dropwise to 66g of methyldimethoxysilane, heated, and reacted at 60 ℃ for 8 hours with stirring.
And mixing the products of the two steps, adding deionized water, stirring at room temperature for 3 hours, and filtering to remove unreacted micromolecules and water in the products.
The product obtained by hydrolysis was mixed with 55g of 2,4,6, 8-tetramethyl-2, 4,6, 8-tetraphenylcyclotetrasiloxane, 89g of pentamethylpentavinylcyclopentasiloxane, 33g of octamethylcyclotetrasiloxane and 2g of hexamethyldisiloxane, and 1.2g of potassium hydroxide was added to react at 70 ℃ for 8 hours. Cooling, adding sodium bicarbonate and diatomite, mixing, stirring uniformly, and performing suction filtration to obtain a filtrate as a target product.
The karstedt catalyst used in each of the above examples was a xylene solution of 1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane platinum (0) with a Pt content of 2 wt%.
The water-based flame-retardant fluorine-containing silicone oil prepared in each example is soluble in water.
The water-based flame-retardant fluorine-containing silicone oil prepared in each embodiment is mixed with
7560，
297，
4000 parts by weight of 1000: 32: 6: 4, coating the mixture on the surface of the base material, and curing the mixture in an oven at 145 ℃ for 90 seconds to obtain the fluorosilicone release film.
And (4) testing standard: flame retardant test standard: UL 94; adhesion test standard: GB/T1720-79 (89); impact resistance test standard: GB/T14485-1993; standard for salt spray resistance testing, GB 10125-1997.
The test results were as follows:
finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (13)
1. A preparation method of water-based flame-retardant fluorine-containing silicone oil comprises the following steps:
(1) mixing allyl phosphate, fluorine-containing olefin and methyldimethoxysilane, heating, and carrying out hydrosilylation reaction under the action of a catalyst to obtain a product A;
(2) mixing monoallyl-terminated polyoxyethylene polyoxypropylene ether with methyldimethoxysilane, heating, and carrying out hydrosilylation reaction under the action of a catalyst to obtain a product B;
(3) mixing the product A and the product B, and adding water for hydrolysis;
(4) mixing the hydrolysate obtained in the step (3) with phenyl cyclosiloxane, vinyl cyclosiloxane, alkyl cyclosiloxane and end-capping reagent, heating and carrying out copolymerization reaction to obtain the water-based flame-retardant fluorine-containing silicone oil;
the catalyst of the hydrosilylation reaction in the step (1) and the step (2) is Karstedt catalyst, and the temperature of the hydrosilylation reaction is controlled at 60-80 ℃;
and (4) adding a catalytic amount of an alkaline catalyst into the copolymerization reaction in the step (4), and controlling the temperature of the copolymerization reaction to be 60-80 ℃.
2. The preparation method of the water-based flame-retardant fluorine-containing silicone oil according to claim 1, characterized by having the following chemical structure:
wherein x = 1-4000, y = 1-4000, z = 1-4000, w = 1-4000, v = 1-4000, and u = 1-4000;
each R1Each independently is alkyl or aryl;
r is a perfluoroalkyl group having 4 to 8 carbon atoms, and Q is an alkylene group having at least 2 carbon atoms;
R2is composed of
Or
；
R3is-CH2CH2CH2O(C2H4O)m(C3H6O)nCH3or-CH2CH2CH2O(C2H4O)m(C3H6O)nH, wherein m = 0-100, n = 0-100, and m + n is more than or equal to 30;
R4is aryl; r5Is an alkyl group.
3. The preparation method of the water-based flame-retardant fluorine-containing silicone oil according to claim 2, wherein the fluorine-containing silicone oil is obtained by copolymerizing the following raw materials in parts by weight:
20-82 parts of phenyl cyclosiloxane,
20-90 parts of vinyl cyclosiloxane,
23-82 parts of alkyl cyclosiloxane,
40-200 parts of methyl dimethoxy silane,
35-80 parts of fluorine-containing olefin,
20-62 parts of allyl phosphate ester,
200-800 parts of monoallyl-terminated polyoxyethylene polyoxypropylene ether,
1-10 parts of an end-capping agent.
4. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the phenylcyclosiloxane is
Wherein a =3 ~ 6.
5. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 4, characterized in that: the phenyl cyclosiloxane is 2,4, 6-trimethyl-2, 4, 6-triphenyl cyclotrisiloxane or 2,4,6, 8-tetramethyl-2, 4,6, 8-tetraphenyl cyclotetrasiloxane.
6. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the vinyl cyclosiloxane is
Wherein b =3 ~ 6.
7. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 6, characterized in that: the vinyl cyclosiloxane is 2,4, 6-trivinyl-2, 4, 6-trimethyl cyclotrisiloxane, tetramethyl tetravinyl cyclotetrasiloxane, pentamethyl pentavinyl cyclopentasiloxane and hexamethyl hexavinyl cyclohexasiloxane.
8. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the alkyl cyclosiloxane is
Wherein c = 3-6, and R' is an alkyl group having 1-18 carbon atoms.
9. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 8, characterized in that: the alkyl cyclosiloxane is hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
10. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the fluorine-containing olefin is R (CH)2)dCH=CH2R is a perfluoroalkyl group having 4 to 8 carbon atoms, and d =0 to 18.
11. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the allyl phosphate is dimethyl allyl phosphate or diethyl allyl phosphate.
12. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the monoallyl-terminated polyoxyethylene polyoxypropylene ether is CH2=CHCH2O(C2H4O)m(C3H6O)nCH3Or CH2=CHCH2O(C2H4O)m(C3H6O)nH, wherein m = 0-100, n = 0-100, and m + n is not less than 30.
13. The preparation method of the water-based flame-retardant fluorosilicone oil according to claim 3, characterized in that: the end-capping agent is hexamethyldisiloxane.
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| CN109836581B (en) * | 2019-03-22 | 2020-10-30 | 上海杰视医疗科技有限公司 | Preparation method of fluorosilicone oil |
| CN112608477A (en) * | 2020-12-17 | 2021-04-06 | 山东东岳高分子材料有限公司 | Linear organic fluorine-containing polysiloxane and preparation method and application thereof |
| CN113024810A (en) * | 2021-03-23 | 2021-06-25 | 南昌大学 | Single-component self-crosslinkable fluorosilicone release agent and preparation method thereof |
| CN112898574B (en) * | 2021-04-01 | 2023-05-12 | 成都思立可科技有限公司 | Preparation method of organic silicon resin |
| CN113583446B (en) * | 2021-07-20 | 2023-07-14 | 江苏皇冠新材料科技有限公司 | Antistatic silica gel protective film and preparation method thereof |
| CN115141671B (en) * | 2022-07-25 | 2023-04-07 | 深圳市润仕达润滑材料有限公司 | Alkyl modified silicone oil insulating lubricating grease |
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Effective date of registration: 20230619 Address after: 246000 101, Building 13, Phoenix Science Park, No. 8, Huangguan Road, High tech Zone, Anqing City, Anhui Province Patentee after: Anqing Longchi Fluorosilicon New Materials Co.,Ltd. Address before: 214000 63 East Ring Road, Yuqi street, Huishan District, Wuxi, Jiangsu Patentee before: HARBIN INSTITUTE OF TECHNOLOGY WUXI Research Institute OF NEW MATERIALS Patentee before: WUXI LONGCHI FLUORINE SILICON NEW MATERIAL CO.,LTD. |