CN109553734A - A kind of emulsifiable organic fluorinated silicone epoxy resin - Google Patents
A kind of emulsifiable organic fluorinated silicone epoxy resin Download PDFInfo
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- CN109553734A CN109553734A CN201811430050.8A CN201811430050A CN109553734A CN 109553734 A CN109553734 A CN 109553734A CN 201811430050 A CN201811430050 A CN 201811430050A CN 109553734 A CN109553734 A CN 109553734A
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- epoxy resin
- vinyl
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
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Abstract
The present invention relates to a kind of emulsifiable organic fluorinated silicone epoxy resin, the present invention first passes through the polytetramethylene ether diol for preparing vinylsiloxane and vinyl epoxy reagent participates in radical polymerization and is combined into combed epoxy resin (present invention), wherein polytetramethylene ether diol is emulsifiable long-chain branch, and water resistance is preferable, alkali resistance is excellent, UV resistant performance is high；Using fluorochemical monomer and siliceous monomer modified, the hydrophobic effect after the present invention solidifies is preferable；Synthesis technology of the invention is simple, easy to operate, it is easy to accomplish industrialized production.
Description
Technical field
The present invention relates to a kind of epoxy resin, more particularly to a kind of emulsifiable organic fluorinated silicone epoxy resin, belong to and prevent again
Rotten technical field of coatings.
Background technique
Epoxy resin refers to the general name of the quasi polymer containing more than two epoxy groups in molecule.It is epoxy chloropropionate
The polycondensation product of alkane and polyalcohol.Due to the chemical activity of epoxy group, its open loop can be made with a variety of compounds containing active hydrogen,
Solidification crosslinking generates reticular structure, therefore it is a kind of thermosetting resin.Bisphenol A epoxide resin is exhausted because of its good corrosion resistance, electricity
Edge is good, cementability is high, cured product excellent in mechanical performance and be widely used in the fields such as electronics, machinery, but its solidify
Density is big after product crosslinking, toughness and humidity resistance are poor.Organosilicon material has excellent low-surface-energy, thermal stability, low temperature
Flexibility etc..Therefore, the introducing of organosilicon reduces the internal stress of bisphenol-A epoxy resin, improves its flexibility, is resistance to oxidation, resistance to
The performances such as damp and hot.
Modified epoxy includes modifying epoxy resin by organosilicon, acrylic resin modified epoxy, polyurethane at present
Modified epoxy, alkyd resin modified epoxy etc., the method for modified epoxy is divided into physical modification and chemical modification.
Cause the uniformity of product poor due to poor compatibility by the mixed and modified epoxy resin of churned mechanically method, mostly presentation phase
Isolated state.And by the method for chemical modification, it not only can solve toughness, thermal stability of resin etc., can also improve
The compatibility of the two.
Chinese patent CN201711211432.7 provides a kind of preparation method of fluorine-silicon modified epoxy resin.The invention is first
Fluorinated acrylate and γ-(methacryloxypropyl) propyl trimethoxy silicane are subjected to pre-polymerization, can adjust fluorine silicon ratio and
Branch lengths；The synthesis process of epoxy resin is divided into two steps, first fluorine silicon prepolymer is grafted, is then expanded again with bisphenol-A
Chain enables fluorine silicon structure to be uniformly distributed in epoxy molecule structure.The invention is powdered epoxy resin, using model
It encloses relatively narrow；In emulsifiable epoxy resin field, fluorinated silicone modified difficulty is larger.
Summary of the invention
It is in order to overcome the shortcomings of the prior art and insufficient, the present invention is intended to provide a kind of emulsifiable organic fluorinated silicone asphalt mixtures modified by epoxy resin
Rouge.
The present invention takes following technical scheme, a kind of emulsifiable organic fluorinated silicone epoxy resin, which is characterized in that by weight
Number meter, preparation method are as follows:
(1) it prepares the polytetramethylene ether diol containing vinylsiloxane: under logical condition of nitrogen gas, 20-40 being added in the reactor
Part polytetramethylene ether diol, 30-50 parts of organic solvents, are heated with stirring to 40-60 DEG C, are slowly added dropwise 5-10 parts dropwise thereto
Active organosilicon monomer, 1-2h is added dropwise rear 40-60 DEG C of heat preservation the reaction was continued 2-4h, is cooled to room temperature, obtains containing vinyl
The solution of the polytetramethylene ether diol of silicon group；
(2) under logical condition of nitrogen gas, it is single that the 40-60 parts of unsaturations containing hydroxyl the preparation of epoxidized monomers: are added in the reactor
Body, 1-2 parts of sulphonic acids catalyst, are heated to 50-70 DEG C, and 15-22 parts of epoxychloropropane, 0.5- are then slowly added dropwise thereto
1h is added dropwise, and is added dropwise and continues 50-70 DEG C of insulation reaction 1-2h, is cooled to room temperature, obtains vinyl epoxy reagent；
(3) preparation of emulsifiable organic fluorinated silicone epoxy resin: under logical nitrogen addition, by the platinum of the 5-10 parts of platinum containing 100-150ppm
(0) in the toluene solution of -1,3- divinyl tetramethyl disiloxane complex compound, 12-20 parts (1) silicon group containing vinyl it is poly-
The solution of tetramethylene ether glycol, 10-15 parts of vinyl epoxy reagents, 4-8 parts of fluorochemical monomers, 10-20 parts of organic solvents are added
Into reaction kettle, it is heated to 70-80 DEG C of reaction 2-4h under stirring condition, then adds 0.05-0.1 parts of initiators the reaction was continued 1-
2h, vacuum distillation remove organic solvent and unreacting substance, obtain emulsifiable organic fluorinated silicone epoxy resin.
The relative molecular mass of the polytetramethylene ether diol is 300-2000.
(1) and organic solvent described in (3) is acetone, methyl acetate, ethyl acetate, butyl acetate, two fourth of ethylene glycol
At least one of ether, glycol dimethyl ether, cyclohexanone, butanone, toluene cyclohexanone, Propylene Glycol Dimethyl Ether.
The active organosilicon monomer is vinyl diphenyl chlorosilane, diisopropyl dichlorosilane, dimethylvinylsiloxy
Base chlorosilane, 1 5- divinyl-hexam ethylcyclotrisiloxane, vinyl trichlorosilane, methylvinyldichlorosilane, methyl second
At least one of alkenyl phenyl chlorosilane；
The unsaturated monomer containing hydroxyl be 3- hydroxyl -1- propylene, 4- hydroxyl -1- propylene, 4- hydroxy butyl vinyl ether,
4-Vinyl phenol, 3- hydroxy styrenes, polyalkylene glycol acrylate ester, 2-hydroxypropyl acrylate, methacrylic acid -2- hydroxyl
At least one of base propyl ester, hydroxy-ethyl acrylate, hydroxyethyl methacrylate.
The sulphonic acids catalyst is p-methyl benzenesulfonic acid, p-methyl benzene sulfonic chloride, Lin Jiaji benzene sulfonic acid, o-methyl-benzene
At least one of sulfonic acid chloride.
The fluorochemical monomer is 1H, seven fluorine amylene of 1H, 2H-, the chloro- 4,5,5- trifluoro amylene of the bromo- 4- of 5-, methacrylic acid
At least one of trifluoro ethyl ester, Hexafluorobutyl mathacrylate, hexafluorobutyl acrylate, acrylic acid trifluoro ethyl ester.
The initiator is peroxidized t-butyl perbenzoate, cumyl peroxide, azo-bis-iso-dimethyl, idol
The different heptonitrile of nitrogen two, perbenzoic acid, benzoyl peroxide, azodiisobutyronitrile, in peroxidating 2- ethyl acid tert-pentyl ester
It is at least one.
Compared with prior art, the invention has the following advantages that passing through the polytetramethylene ether for preparing vinylsiloxane
Two pure and mild vinyl epoxy reagents participate in radical polymerization and are combined into combed epoxy resin (present invention), wherein polytetramethylene ether diol
For emulsifiable long-chain branch, water resistance is preferable, alkali resistance is excellent, UV resistant performance is high；Changed using fluorochemical monomer and siliceous monomer
Property, the hydrophobic effect after the present invention solidifies is preferable；Synthesis technology of the invention is simple, easy to operate, it is easy to accomplish industrial metaplasia
It produces.
Specific embodiment
It is further described below with reference to the embodiment organic fluorinated silicone epoxy resin emulsifiable to one kind of the invention.It can
With understanding, specific embodiment described herein is used only for explaining related invention, rather than the restriction to the invention.
Embodiment 1
A kind of emulsifiable organic fluorinated silicone epoxy resin X, which is characterized in that according to parts by weight, preparation method is as follows:
(1) it prepares the polytetramethylene ether diol containing vinylsiloxane: under logical condition of nitrogen gas, 20 parts being added in the reactor and gathers
Tetramethylene ether glycol, 30 parts of organic solvents, are heated with stirring to 60 DEG C, and 5 parts of active organosilicon is slowly added dropwise dropwise thereto
Monomer, 60 DEG C of heat preservation the reaction was continued 2h after 1h is added dropwise, is cooled to room temperature, obtains the polytetramethylene ether of the silicon group containing vinyl
The solution of glycol；
(2) under logical condition of nitrogen gas, 60 parts of unsaturated monomers containing hydroxyl, 2 preparation of epoxidized monomers: are added in the reactor
Part sulphonic acids catalyst, is heated to 50 DEG C, 22 parts of epoxychloropropane is then slowly added dropwise thereto, and 1h is added dropwise, and is added dropwise
It finishes and continues 50 DEG C of insulation reaction 2h, be cooled to room temperature, obtain vinyl epoxy reagent；
(3) preparation of emulsifiable organic fluorinated silicone epoxy resin: under logical nitrogen addition, by the platinum (0) -1 of 6 parts of platinum containing 120ppm,
The toluene solution of 3- divinyl tetramethyl disiloxane complex compound, in 17 parts (1) silicon group containing vinyl polytetramethylene
The solution of ether glycol, 12 parts of vinyl epoxy reagents, 6 parts of fluorochemical monomers, 14 parts of organic solvents are added in reaction kettle, stirring bar
Be heated to 73 DEG C of reaction 3h under part, then add 0.08 part of initiator the reaction was continued 1.5h, vacuum distillation remove organic solvent and
Unreacting substance obtains emulsifiable organic fluorinated silicone epoxy resin X.
Embodiment 2
A kind of emulsifiable organic fluorinated silicone epoxy resin Y, which is characterized in that according to parts by weight, preparation method is as follows:
(1) it prepares the polytetramethylene ether diol containing vinylsiloxane: under logical condition of nitrogen gas, 29 parts being added in the reactor and gathers
Tetramethylene ether glycol, 40 parts of organic solvents, are heated with stirring to 48 DEG C, and 7 parts of active organosilicon is slowly added dropwise dropwise thereto
Monomer, 48 DEG C of heat preservation the reaction was continued 3h after 1.5h is added dropwise, is cooled to room temperature, obtains the polytetramethylene of the silicon group containing vinyl
The solution of ether glycol；
(2) under logical condition of nitrogen gas, 40 parts of unsaturated monomers containing hydroxyl, 1 preparation of epoxidized monomers: are added in the reactor
Part sulphonic acids catalyst, is heated to 70 DEG C, 15 parts of epoxychloropropane is then slowly added dropwise thereto, and 0.5h is added dropwise, drop
70 DEG C of insulation reaction 1h of Bi Jixu are added, is cooled to room temperature, obtains vinyl epoxy reagent；
(3) preparation of emulsifiable organic fluorinated silicone epoxy resin: under logical nitrogen addition, by the platinum (0) -1 of 10 parts of platinum containing 150ppm,
The toluene solution of 3- divinyl tetramethyl disiloxane complex compound, in 20 parts (1) silicon group containing vinyl polytetramethylene
The solution of ether glycol, 15 parts of vinyl epoxy reagents, 8 parts of fluorochemical monomers, 20 parts of organic solvents are added in reaction kettle, stirring bar
It is heated to 70 DEG C of reaction 4h under part, then adds 0.1 part of initiator the reaction was continued 2h, vacuum distillation removes organic solvent and not instead
Substance is answered, emulsifiable organic fluorinated silicone epoxy resin Y is obtained.
Embodiment 3
A kind of emulsifiable organic fluorinated silicone epoxy resin Z, which is characterized in that according to parts by weight, preparation method is as follows:
(1) it prepares the polytetramethylene ether diol containing vinylsiloxane: under logical condition of nitrogen gas, 40 parts being added in the reactor and gathers
Tetramethylene ether glycol, 50 parts of organic solvents, are heated with stirring to 40 DEG C, and 10 parts of active organosilicon is slowly added dropwise dropwise thereto
Monomer, 40 DEG C of heat preservation the reaction was continued 4h after 2h is added dropwise, is cooled to room temperature, obtains the polytetramethylene ether of the silicon group containing vinyl
The solution of glycol；
(2) preparation of epoxidized monomers: under logical condition of nitrogen gas, be added in the reactor 45 parts of unsaturated monomers containing hydroxyl,
1.3 parts of sulphonic acids catalyst, are heated to 60 DEG C, and 18 parts of epoxychloropropane is then slowly added dropwise thereto, and 0.7h is added dropwise,
It is added dropwise and continues 60 DEG C of insulation reaction 1.5h, be cooled to room temperature, obtain vinyl epoxy reagent；
(3) preparation of emulsifiable organic fluorinated silicone epoxy resin: under logical nitrogen addition, by the platinum (0) -1 of 5 parts of platinum containing 100ppm,
The toluene solution of 3- divinyl tetramethyl disiloxane complex compound, in 12 parts (1) silicon group containing vinyl polytetramethylene
The solution of ether glycol, 10 parts of vinyl epoxy reagents, 4 parts of fluorochemical monomers, 10 parts of organic solvents are added in reaction kettle, stirring bar
It is heated to 80 DEG C of reaction 2h under part, then adds 0.05 part of initiator the reaction was continued 1h, vacuum distillation removes organic solvent and not
Reactive material obtains emulsifiable organic fluorinated silicone epoxy resin Z.
By " emulsifiable organic fluorinated silicone epoxy resin " described in 1-3 of the embodiment of the present invention: diethyl triamine: water=40:
Emulsification is mixed uniformly in 15:55, and brush is in cement matrix surface under the same terms, and after being fully cured, performance test is as follows:
Although the present invention has described it in detail and cited embodiments, but for those of ordinary skill in the art, it is clear that can
With various schemes, modification and the change made as specified above, should be construed as being included within the scope of the claims.
Claims (8)
1. a kind of emulsifiable organic fluorinated silicone epoxy resin, which is characterized in that according to parts by weight, described emulsifiable organic
Fluorine epoxy silicone the preparation method is as follows:
(1) it prepares the polytetramethylene ether diol containing vinylsiloxane: under logical condition of nitrogen gas, 20-40 being added in the reactor
Part polytetramethylene ether diol, 30-50 parts of organic solvents, are heated with stirring to 40-60 DEG C, are slowly added dropwise 5-10 parts dropwise thereto
Active organosilicon monomer, 1-2h is added dropwise rear 40-60 DEG C of heat preservation the reaction was continued 2-4h, is cooled to room temperature, obtains containing vinyl
The solution of the polytetramethylene ether diol of silicon group；
(2) under logical condition of nitrogen gas, it is single that the 40-60 parts of unsaturations containing hydroxyl the preparation of epoxidized monomers: are added in the reactor
Body, 1-2 parts of sulphonic acids catalyst, are heated to 50-70 DEG C, and 15-22 parts of epoxychloropropane, 0.5- are then slowly added dropwise thereto
1h is added dropwise, and is added dropwise and continues 50-70 DEG C of insulation reaction 1-2h, is cooled to room temperature, obtains vinyl epoxy reagent；
(3) preparation of emulsifiable organic fluorinated silicone epoxy resin: under logical nitrogen addition, by the platinum of the 5-10 parts of platinum containing 100-150ppm
(0) in the toluene solution of -1,3- divinyl tetramethyl disiloxane complex compound, 12-20 parts (1) silicon group containing vinyl it is poly-
The solution of tetramethylene ether glycol, 10-15 parts of vinyl epoxy reagents, 4-8 parts of fluorochemical monomers, 10-20 parts of organic solvents are added
Into reaction kettle, it is heated to 70-80 DEG C of reaction 2-4h under stirring condition, then adds 0.05-0.1 parts of initiators the reaction was continued 1-
2h, vacuum distillation remove organic solvent and unreacting substance, obtain emulsifiable organic fluorinated silicone epoxy resin.
2. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that the polytetramethylene
The relative molecular mass of ether glycol is 300-2000.
3. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that (1) and described in (3)
Organic solvent is acetone, methyl acetate, ethyl acetate, butyl acetate, butyl cellosolve, glycol dimethyl ether, cyclohexanone, fourth
At least one of ketone, toluene cyclohexanone, Propylene Glycol Dimethyl Ether.
4. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that the active organosilicon
Monomer is vinyl diphenyl chlorosilane, diisopropyl dichlorosilane, dimethyl vinyl chlorosilane, 1 5- divinyl-six
Methyl trisiloxanes, vinyl trichlorosilane, methylvinyldichlorosilane, at least one in methyl vinyl phenyl chlorosilane
Kind.
5. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that described containing hydroxyl
Unsaturated monomer is 3- hydroxyl -1- propylene, 4- hydroxyl -1- propylene, 4- hydroxy butyl vinyl ether, 4-Vinyl phenol, 3- hydroxyl
Styrene, polyalkylene glycol acrylate ester, 2-hydroxypropyl acrylate, methacrylic acid -2- hydroxy propyl ester, hydroxy-ethyl acrylate,
At least one of hydroxyethyl methacrylate.
6. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that the sulphonic acids catalysis
Agent is at least one of p-methyl benzenesulfonic acid, p-methyl benzene sulfonic chloride, Lin Jiaji benzene sulfonic acid, o-methyl-benzene sulfonic acid chloride.
7. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that the fluorochemical monomer is
Seven fluorine amylene of 1H, 1H, 2H-, the chloro- 4,5,5- trifluoro amylene of the bromo- 4- of 5-, trifluoroethyl methacrylate, methacrylic acid hexafluoro
At least one of butyl ester, hexafluorobutyl acrylate, acrylic acid trifluoro ethyl ester.
8. emulsifiable organic fluorinated silicone epoxy resin according to claim 1, which is characterized in that the initiator was
Aoxidize t-butyl perbenzoate, cumyl peroxide, azo-bis-iso-dimethyl, azobisisoheptonitrile, perbenzoic acid,
At least one of benzoyl peroxide, azodiisobutyronitrile, peroxidating 2- ethyl acid tert-pentyl ester.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811430050.8A CN109553734A (en) | 2018-11-28 | 2018-11-28 | A kind of emulsifiable organic fluorinated silicone epoxy resin |
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| CN201811430050.8A CN109553734A (en) | 2018-11-28 | 2018-11-28 | A kind of emulsifiable organic fluorinated silicone epoxy resin |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110511651A (en) * | 2019-08-31 | 2019-11-29 | 嘉兴菱凡贸易有限公司 | A kind of UV Absorption type is total to block epoxy resin water paint and its preparation method |
| CN113480235A (en) * | 2021-08-05 | 2021-10-08 | 常州华光建材科技有限公司 | High-strength epoxy resin repair mortar and preparation method thereof |
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