CN107602861A - A kind of waterborne flame retardant fluorine containing silicone oil and preparation method thereof - Google Patents
A kind of waterborne flame retardant fluorine containing silicone oil and preparation method thereof Download PDFInfo
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- CN107602861A CN107602861A CN201710751849.6A CN201710751849A CN107602861A CN 107602861 A CN107602861 A CN 107602861A CN 201710751849 A CN201710751849 A CN 201710751849A CN 107602861 A CN107602861 A CN 107602861A
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Abstract
The invention discloses kind of a waterborne flame retardant fluorine containing silicone oil, has following chemical constitution：Each R1It is independently each alkyl or aryl；R is the perfluoroalkyl with 4~8 carbon atoms, and Q is the alkylidene at least containing 2 carbon atoms；R2ForR3For polyoxyethylene poly-oxygen propylene aether chain；R4For aryl；R5For alkyl.Obtained by the material copolymerization including following parts by weight：20~82 parts of phenyl ring siloxane, 20~90 parts of vinylcyclosiloxanes, 23~66 parts of alkyl-cyclosiloxanes, 40~200 parts of methyl dimethoxysilane, 40~80 parts of Fluorine containing olefine, 20~56 parts of pi-allyl phosphate, 200~800 parts of the polyoxyethylene poly-oxygen propylene aether of monoallyl end-blocking, 1~10 part of end-capping reagent.The waterborne flame retardant fluorine containing silicone oil does not need organic solvent, green, while has good flame retardant effect and preferable release effect, can apply more multi-field.
Description
Technical field
The invention belongs to fluorine containing silicone oil field, more particularly to a kind of waterborne flame retardant fluorine containing silicone oil and preparation method thereof.
Background technology
Fluoropolymer has relatively low surface free energy, superpower weatherability, outstanding salt fog resistance, has some resistants
The features such as property, 20th century the eighties, fluorine element is introduced into organosilicon first.Fluorine containing silicone oil is with poly- containing fluoroalkyl side chains
Siloxanes, its unique molecular structure impart the superior high and low temperature resistance of fluorine containing silicone oil, excellent oxidation resistent susceptibility and resistance to
Time property etc..
Fluorine containing silicone oil is first hydrolyzed by using the chlorosilane containing fluoroalkyl, then is carried out ring-opening polymerisation and be made.In this mistake
Cheng Zhonghui largely uses organic solvent, and organic solvent is unfavorable for environment, does not meet green requirement.The water-based fluorine silicon developed
Polymer typically all using fluoroolefins containing reactive double bond, organic silicon monomer and acrylicacidandesters, is gathered by free-atom aqueous solution
Close, i.e., fluorine-containing polymer is first synthesized in organic solvent medium, then make the fluoropolymer of dissolving under emulsifying agent effect
Prepare aqueous dispersion or its aqueous dispersion is directly prepared by free-radical emulsion polymerization, this method is still related in building-up process
To organic solvent.
The fire retardant kind of current practice has a lot, can be divided into halogen system, organophosphor system, phosphorus-nitrogen system (halogen-free expansible
Fire retardant), silicon-type and it is inorganic system etc..With the hair of electrical equipment, electronics, machinery, automobile, ship, Aeronautics and Astronautics and chemical industry
Exhibition, it is also more and more high to the flame-retardancy requirements of product material, it is therefore desirable to prepare a fluorine silicon having compared with low surface free energy
Oil has preferable anti-flaming function.
The content of the invention
The technical problem to be solved in the present invention is the defects of overcoming existing silane-modified resin, there is provided a kind of silane-modified
Polymer and preparation method thereof.
In order to solve the above-mentioned technical problem, the invention provides following technical scheme：
A kind of waterborne flame retardant fluorine containing silicone oil, there is following chemical constitution：
Wherein, x=1~4000, y=1~4000, z=1~4000, w=1~4000, v=1~4000, u=1~
4000；
Each R1It is independently each alkyl or aryl；
R is the perfluoroalkyl with 4~8 carbon atoms, and Q is the alkylidene at least containing 2 carbon atoms；
R2For
R3For-CH2CH2CH2O(C2H4O)m(C3H6O)nCH3Or-CH2CH2CH2O(C2H4O)m(C3H6O)nH, wherein m=0~
100, n=0~100, and m+n >=30；
R4For aryl；R5For alkyl, preferably described alkyl is the alkyl of 1~18 carbon number, the aryl be phenyl (Ph),
P-methylphenyl, o-methyl-phenyl, 1- naphthyls, 2- naphthyls etc..
A kind of waterborne flame retardant fluorine containing silicone oil, is obtained by the material copolymerization including following parts by weight：
Preferably, the phenyl ring siloxane isWherein, a=3~6, such as 2,4,6- trimethyls -2,4,6-
Triphenyl cyclotrisiloxane, 2,4,6,8- tetramethyl -2,4,6,8- tetraphenyl cyclotetrasiloxanes.
Preferably, described vinylcyclosiloxanes areWherein, b=3~6, such as 2,4,6- triethylenes
Base -2,4,6- trimethyls cyclotrisiloxane, t etram-ethyltetravinylcyclotetrasiloxane, the vinyl D5 of pentamethyl five,
The siloxanes of six ethene basic ring of hexamethyl six.
Preferably, described alkyl-cyclosiloxanes areWherein, c=3~6, R ' be 1~18 carbon number alkane
Base, specific alkyl-cyclosiloxanes such as hexamethyl cyclotrisiloxane, octamethylcy-clotetrasiloxane, decamethylcyclopentaandoxane, ten
The siloxanes of diformazan basic ring six.
Preferably, it is characterised in that：Described Fluorine containing olefine is R (CH2)dCH=CH2, R is with 4~8 carbon atoms
Perfluoroalkyl, d=0~18.
Preferably, described pi-allyl phosphate is pi-allyl dimethyl phosphate or pi-allyl diethyl phosphate.
Preferably, the polyoxyethylene poly-oxygen propylene aether of monoallyl end-blocking is CH2=CHCH2O(C2H4O)m(C3H6O)nCH3
Or CH2=CHCH2O(C2H4O)m(C3H6O)nH, wherein m=0~100, n=0~100, and m+n >=30.
Preferably, the end-capping reagent is HMDO.
The preparation method of above-mentioned waterborne flame retardant fluorine containing silicone oil, comprises the following steps：
(1) pi-allyl phosphate, Fluorine containing olefine and methyl dimethoxysilane are mixed, heats and issued in catalyst action
Raw hydrosilylation, obtains product A；
(2) polyoxyethylene poly-oxygen propylene aether that monoallyl blocks is mixed with methyl dimethoxysilane, heats and urging
Agent effect is lower to occur hydrosilylation, obtains product B；
(3) product A and product B is mixed, adds water to be hydrolyzed；
(4) by the hydrolysate of step (3) and phenyl ring siloxane, vinylcyclosiloxanes, alkyl-cyclosiloxanes, end-blocking
Agent mixes, and heating, copolyreaction obtains described waterborne flame retardant fluorine containing silicone oil.
The hydrosilylation of step (1) and step (2) can add the platinum group catalyst of catalytic amount, such as anti-poisoning
Karstedt catalyst, Speier catalyst etc., the temperature control of hydrosilylation at 60~80 DEG C, preferably adopt by catalyst
With the more preferable Karstedt catalyst of anti-poisoning effect.
The copolyreaction of step (4) can add the base catalyst of catalytic amount, as potassium hydroxide, TMAH,
Six pyrrolidines diphosphine nitrile hydroxide etc., the temperature control of copolyreaction is at 60~80 DEG C.
The waterborne flame retardant fluorine containing silicone oil of the present invention does not need organic solvent, water-soluble, and without making in building-up process
It is green with organic solvent, while there is good flame retardant effect and preferable release effect, widen fluorine containing silicone oil and applied
The application in material field.
Brief description of the drawings
Accompanying drawing is used for providing a further understanding of the present invention, and a part for constitution instruction, the reality with the present invention
Apply example to be used to explain the present invention together, be not construed as limiting the invention.In the accompanying drawings：
Fig. 1 is the infrared spectrum of fluorine containing silicone oil prepared by the embodiment of the present invention 1.
Embodiment
The preferred embodiments of the present invention are illustrated below in conjunction with accompanying drawing, it will be appreciated that described herein preferred real
Apply example to be merely to illustrate and explain the present invention, be not intended to limit the present invention.
Embodiment 1
After 50g pi-allyls diethyl phosphate, 40g perfluorobutyl ethylenes, 0.5g karstedt catalyst are mixed, it is added dropwise
Into 100g methyl dimethoxysilanes, 70 DEG C are heated to, stirring reaction 5 hours.
The polyoxyethylene poly-oxygen propylene aether that 200g monoallyls are blocked (moistens the limited public affairs of standing grain new high-tech material science and technology share in Ningbo
Take charge of RHTJ-002M), 0.5g karstedt catalyst mixing after, be added drop-wise in 40g methyl dimethoxysilanes, be heated to 60
DEG C, stirring reaction 8 hours.
The product of above-mentioned two step is mixed, deionized water is added and is stirred at room temperature 3 hours, is filtered unreacted in removing product
Small molecule and moisture.
The product that above-mentioned hydrolysis is obtained and 55g 2,4,6,8- tetramethyl -2,4,6,8- tetraphenyls cyclotetrasiloxane, 89g
The vinyl D5 of pentamethyl five, 33g octamethylcy-clotetrasiloxanes, the mixing of 2g HMDOs, add 1.8g hydrogen
Potassium oxide reacts 8 hours at 70 DEG C, and cooling adds sodium acid carbonate and mixed with diatomite, is filtered after stirring, filtrate
For target product.
Embodiment 2
After 50g pi-allyls dimethyl phosphate, 40g perfluorobutyl ethylenes, 0.5g karstedt catalyst are mixed, it is added dropwise
Into 100g methyl dimethoxysilanes, heating, 70 DEG C of stirring reactions 5 hours.
The polyoxyethylene poly-oxygen propylene aether that 200g monoallyls are blocked (moistens the limited public affairs of standing grain new high-tech material science and technology share in Ningbo
Take charge of RHTJ-002M), 0.5g karstedt catalyst mixing after, be added drop-wise in 40g methyl dimethoxysilanes, heat, 60 DEG C
Stirring reaction 8 hours.
The product of above-mentioned two step is mixed, deionized water is added and is stirred at room temperature 3 hours, is filtered unreacted in removing product
Small molecule and remaining moisture.
The product that above-mentioned hydrolysis is obtained and the vinyl D5 of 72g pentamethyls five, the silica of 82g prestoxs ring four
Alkane, 20g 2,4,6,8- tetramethyl -2,4,6,8- tetraphenyls cyclotetrasiloxane, the mixing of 2g HMDOs add 1.5g hydrogen
Potassium oxide reacts 8 hours at 70 DEG C.Cooling adds sodium acid carbonate and mixed with diatomite, is filtered after stirring, filtrate
For target product.
Embodiment 3
After 62g pi-allyls diethyl phosphate, 35g perfluorooctyl ethylenes, 0.5g, karstedt catalyst are mixed, it is added dropwise
Into 87g methyl dimethoxysilanes, heating, 70 DEG C of stirring reactions 5 hours.
The polyoxyethylene poly-oxygen propylene aether that 352g monoallyls are blocked (moistens the limited public affairs of standing grain new high-tech material science and technology share in Ningbo
Take charge of RHTJ-002M), 0.5g karstedt catalyst mixing after, be added drop-wise in 66g methyl dimethoxysilanes, heat, 60 DEG C
Stirring reaction 8 hours.
The product of above-mentioned two step is mixed, deionized water is added and is stirred at room temperature 3 hours, is filtered unreacted in removing product
Small molecule and moisture.
Obtained product and 55g 2,4,6,8- tetramethyl -2,4,6,8- tetraphenyls cyclotetrasiloxane, the first of 89g five will be hydrolyzed
The vinyl D5 of base five, 33g octamethylcy-clotetrasiloxanes, the mixing of 2g HMDOs, add 1.2g hydroxides
Potassium reacts 8 hours at 70 DEG C.Cooling adds sodium acid carbonate and mixed with diatomite, is filtered after stirring, filtrate is mesh
Mark product.
Karstedt catalyst used in the various embodiments described above is 1,3- divinyl -1,1,3,3- tetramethyl disiloxanes
The xylene solution of platinum (0), Pt contents 2wt%.
The various embodiments described above prepare waterborne flame retardant fluorine containing silicone oil it is water-soluble in.
By the various embodiments described above prepare waterborne flame retardant fluorine containing silicone oil with7560,297,4000 press 1000：32：6：4 mass ratio mixing, is applied to substrate surface, curing oven 90 seconds at 145 DEG C,
Obtain fluorine silicon mould release membrance.
Testing standard：Flame-retardant test criteria：UL94；Adhesive force testing standard：GB/T1720-79(89)；Impact resistance is tested
Standard：GB/T 14485-1993；Salt spray resistance testing standard GB10125-1997.
Test result is as follows：
Finally it should be noted that：The preferred embodiments of the present invention are the foregoing is only, are not intended to limit the invention,
Although the present invention is described in detail with reference to the foregoing embodiments, for those skilled in the art, it still may be used
To be modified to the technical scheme described in foregoing embodiments, or equivalent substitution is carried out to which part technical characteristic.
Within the spirit and principles of the invention, any modification, equivalent substitution and improvements made etc., it should be included in the present invention's
Within protection domain.
Claims (10)
1. a kind of waterborne flame retardant fluorine containing silicone oil, there is following chemical constitution：
Wherein, x=1~4000, y=1~4000, z=1~4000, w=1~4000, v=1~4000, u=1~4000；
Each R1It is independently each alkyl or aryl；
R is the perfluoroalkyl with 4~8 carbon atoms, and Q is the alkylidene at least containing 2 carbon atoms；
R2For
R3For-CH2CH2CH2O(C2H4O)m(C3H6O)nCH3Or-CH2CH2CH2O(C2H4O)m(C3H6O)nH, wherein m=0~100, n
=0~100, and m+n >=30；
R4For aryl；R5For alkyl.
2. a kind of waterborne flame retardant fluorine containing silicone oil, is obtained by the material copolymerization including following parts by weight：
3. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：The phenyl ring siloxane isWherein, a=3~6, such as 2,4,6- trimethyls -2,4,6- triphenyls cyclotrisiloxane, 2,4,6,8- tetramethyls -
2,4,6,8- tetraphenyl cyclotetrasiloxanes.
4. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：Described vinylcyclosiloxanes areWherein, b=3~6, such as 2,4,6- trivinyls -2,4,6- trimethyls cyclotrisiloxane, the ethene of tetramethyl four
Basic ring tetrasiloxane, the vinyl D5 of pentamethyl five, the siloxanes of six ethene basic ring of hexamethyl six.
5. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：Described alkyl-cyclosiloxanes areWherein, c=3~6, R ' be 1~18 carbon number alkyl, the specific alkyl-cyclosiloxanes such as silicon of pregnancy basic ring three
Oxygen alkane, octamethylcy-clotetrasiloxane, decamethylcyclopentaandoxane, the siloxanes of ten diformazan basic ring six.
6. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：Described Fluorine containing olefine is R (CH2)dCH
=CH2, R is the perfluoroalkyl with 4~8 carbon atoms, d=0~18.
7. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：Described pi-allyl phosphate is allyl
Base dimethyl phosphate or pi-allyl diethyl phosphate.
8. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：The polyoxyethylene of monoallyl end-blocking gathers
Oxypropylene ether is CH2=CHCH2O(C2H4O)m(C3H6O)nCH3Or CH2=CHCH2O(C2H4O)m(C3H6O)nH, wherein m=0~
100, n=0~100, and m+n >=30.
9. waterborne flame retardant fluorine containing silicone oil according to claim 2, it is characterised in that：The end-capping reagent is the silica of hexamethyl two
Alkane.
10. the preparation method of the waterborne flame retardant fluorine containing silicone oil of claim 1 or 2, comprises the following steps：
(1) pi-allyl phosphate, Fluorine containing olefine and methyl dimethoxysilane are mixed, heats and silicon occurs under catalyst action
Addition reaction of hydrogen, obtain product A；
(2) polyoxyethylene poly-oxygen propylene aether that monoallyl blocks is mixed with methyl dimethoxysilane, heated in catalyst
Effect is lower to occur hydrosilylation, obtains product B；
(3) product A and product B is mixed, adds water to be hydrolyzed；
(4) hydrolysate of step (3) is mixed with phenyl ring siloxane, vinylcyclosiloxanes, alkyl-cyclosiloxanes, end-capping reagent
Close, heating, copolyreaction obtains described waterborne flame retardant fluorine containing silicone oil；
Preferably, the catalyst of the hydrosilylation of step (1) and step (2) is platinum group catalyst, more preferably
Karstedt catalyst, the temperature control of hydrosilylation is at 60~80 DEG C；
Preferably, the copolyreaction of step (4) can add the base catalyst of catalytic amount, and the temperature control of copolyreaction is 60
~80 DEG C.
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Cited By (7)
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| CN108676134A (en) * | 2018-04-02 | 2018-10-19 | 哈尔滨工业大学无锡新材料研究院 | The cross-linking fire-retardant fluorine containing silicone oil of one kind, preparation method and fire-retardant release coating |
| CN109836581A (en) * | 2019-03-22 | 2019-06-04 | 上海杰视医疗科技有限公司 | A kind of preparation method of fluorosilicon 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 |
| CN112898574A (en) * | 2021-04-01 | 2021-06-04 | 成都思立可科技有限公司 | Preparation method of organic silicon resin |
| CN113024810A (en) * | 2021-03-23 | 2021-06-25 | 南昌大学 | Single-component self-crosslinkable fluorosilicone release agent and preparation method thereof |
| CN113583446A (en) * | 2021-07-20 | 2021-11-02 | 江苏皇冠新材料科技有限公司 | Antistatic silica gel protective film and preparation method thereof |
| CN115141671A (en) * | 2022-07-25 | 2022-10-04 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108676134A (en) * | 2018-04-02 | 2018-10-19 | 哈尔滨工业大学无锡新材料研究院 | The cross-linking fire-retardant fluorine containing silicone oil of one kind, preparation method and fire-retardant release coating |
| CN108676134B (en) * | 2018-04-02 | 2020-10-09 | 哈尔滨工业大学无锡新材料研究院 | Crosslinkable flame-retardant fluorine-containing silicone oil, preparation method thereof and flame-retardant release coating |
| CN109836581A (en) * | 2019-03-22 | 2019-06-04 | 上海杰视医疗科技有限公司 | A kind of preparation method of fluorosilicon 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 |
| CN112898574A (en) * | 2021-04-01 | 2021-06-04 | 成都思立可科技有限公司 | Preparation method of organic silicon resin |
| CN113583446A (en) * | 2021-07-20 | 2021-11-02 | 江苏皇冠新材料科技有限公司 | Antistatic silica gel protective film and preparation method thereof |
| CN115141671A (en) * | 2022-07-25 | 2022-10-04 | 深圳市润仕达润滑材料有限公司 | Alkyl modified silicone oil insulating lubricating grease |
| 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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