CN109233478A - A kind of fluorine-containing organic silicon stone protective agent and preparation method thereof - Google Patents
A kind of fluorine-containing organic silicon stone protective agent and preparation method thereof Download PDFInfo
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- CN109233478A CN109233478A CN201810842224.5A CN201810842224A CN109233478A CN 109233478 A CN109233478 A CN 109233478A CN 201810842224 A CN201810842224 A CN 201810842224A CN 109233478 A CN109233478 A CN 109233478A
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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
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
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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
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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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
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1675—Polyorganosiloxane-containing compositions
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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
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1687—Use of special additives
Abstract
A kind of fluorine-containing organic silicon stone protective agent and preparation method thereof, the protective agent is made of following component in parts by weight: 0.1~10 part of alkoxysilane mixture；1~20 part of fluorochemical；0.1~10 part of organopolysiloxane；0.1~30 part of silane coupling agent；0~1 part of catalyst；60~100 parts of solvent, first alkoxysilane mixture, fluorochemical, organopolysiloxane are added sequentially to be equipped in the reaction kettle of solvent when preparation, mixed liquor is obtained after stirring, silane coupling agent is added in mixed liquor again, stirring forms premix, catalyst is finally added in premix, aging reaction obtains protective agent after stirring.Fluorochemical is introduced into organosilicon protective agent by the present invention is applied to stone protector, has both kept the good waterproofness of stone material, weatherability, have the characteristics that good resistance to oil stains, and solution organosiloxane protective agent is intolerant to the defect of greasy dirt, and cost is reasonable.
Description
Technical field
The invention belongs to protective agent technical field, specifically a kind of fluorine-containing organic silicon stone protective agent and its preparation side
Method.
Background technique
Stone material is a kind of porosity mineral, inside there are a large amount of microgap and pore, be chronically exposed to natural environment
In, many liquid objects such as cement pulp-water when water, dust, greasy dirt, colored liquid and wet combining are constructed easily make stone product
It at pollution, destroys, causes a variety of lesions to generate, as water spots, rust staining spit Huang, surface corrosion, pigment pollution (including greasy dirt), dusting
Peel off etc., substantially reduce the decorative effect and service life of stone material.The effect of stone protectant is exactly to be effectively prevented from stone
Material generates lesion by these pollutions, it is ensured that it is permanent as new that stone material achievees the effect that, extends the service life of stone material.
It is traditional silane/siloxane class waterproofing agent of organosilicon that existing market, which is applied more,.Because of organic silicon water-proofing
Agent has good waterproof performance, effective that moisture is prevented to invade, while organosilicon material has excellent oxytolerant, ozone, purple
Outer light action.When organosilicon material is painted on silicate substrate surface, the siloxanes with reactivity can not only pass through work
Property group interaction form hydrophobic reticulated siloxane molecule film, moreover it is possible to in substrate hydroxyl occur condensation reaction formed
End has the silane chain of alkyl.This hydrophobic reticulated siloxane molecule film has very low surface tension, can uniformly divide
Cloth is on wall.Patent CN 102108220A describe it is a kind of by containing hydrogen silicone oil after series reaction under basic conditions with solvent
Mixing, waterproofing agent of organosilicon obtained have good waterproofness.Patent CN 1962805A provide a kind of solvent-type organosilicon
Waterproofing agent preparation method: active organosilicon alkane, active organosilicon oil, active organosilicon resin, catalyst, organic solvent etc. is mixed
The characteristics of closing and be made, good penetrability, good weatherability are had both on the basis of waterproof.But the shortcomings that this kind of organosilicon protective agent, is
Resistance to soiling is insufficient, cannot prevent greasy dirt.
Fluorochemical is introduced in waterproofing agent of organosilicon, then can assign waterproofing agent good oil-stain-preventing performance.Fluorine is member
The maximum element of electronegativity in plain periodic table, its atomic radius is only more slightly larger than hydrogen atom, has minimum polarizability.So containing
The chemical resistance of fluorine compounds is fabulous.Meanwhile fluorine atom checks its electron outside nucleus and the constraint of bonding electrons cloud is very strong, C-F key
Polarizability is low, and the intermolecular force containing C=F is lower, thus has special surface property, shows water resistance, oil resistivity preferably
And stain resistance.Patent CN 102815884A describes a kind of fluorine-containing organic silicon waterproof material for concrete, using containing
Perfluoroalkyl acrylate resin, polyacrylamide modified resin, polyvinyl alcohol modification resin, organosiloxane, silane coupling agent, Lewis
Acid adds silane coupling agent stirring certain time, is eventually adding Lewis first by 3 kinds of resins and organosiloxane hybrid reaction
Acid is stirred to react generation final products.The invention is primarily adapted for use in road surface, bridge, the tunnel water proofing field of coagulating cement soil matrix,
The original appearance of change occur since its film forming has residue for lithotome cannot be applicable in.Patent CN 103058528A
Disclose a kind of glass surface with preparations such as fluorine-containing organic silicon alkane, vinyltriethoxysilane, methyltriethoxysilane
Processing waterproofing agent of organosilicon, is mainly used for the glass surface of surface texture densification, answers on the stone surface of cellular structure
With again have any different.
Traditional silane/siloxane organosilicon protective agent, it will be apparent that defect is exactly resistance to oil stains difference.Using pure fluorine compounds
Stone material is protected since the price is very expensive for it, cost is excessively high, cannot replace widely used organosilicon in market completely
Protective agent.Fluorochemical is introduced into organosilicon protective agent on the basis of not increasing cost and is applied to stone protector, is
The development trend of stone protectant at present.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of fluorine-containing organic silicon stone protective agents and preparation method thereof, will contain
Fluorine compounds, which are introduced into organosilicon protective agent, is applied to stone protector, has both kept stone material good waterproofness, weatherability, more
Have the characteristics that good resistance to oil stains, solves organosiloxane protective agent intolerant to the defect of greasy dirt, and cost is reasonable.
In order to solve the above-mentioned technical problem, the present invention takes following technical scheme:
A kind of fluorine-containing organic silicon stone protective agent, the protective agent are made of following component in parts by weight: alkoxy
0.1~10 part of silane mixture；1~20 part of fluorochemical；0.1~10 part of organopolysiloxane；Silane coupling agent 0.1~30
Part；0~1 part of catalyst；60~100 parts of solvent.
The alkoxysilane mixture refers to that the silane/siloxane with reaction active groups of low molecular weight is oligomeric
Object.
The fluorochemical refers to the perfluoroalkoxy polymer long containing fluorocarbon chain.
The organopolysiloxane refers to hydrosilicon Functional siloxane.
The silane coupling agent is methyltriethoxysilane, methyltrimethoxysilane, ethyl triethoxysilane, second
Base trimethoxy silane, propyl-triethoxysilicane, propyl trimethoxy silicane, butyl triethoxysilane, butyl trimethoxy
Base silane, octyltri-ethoxysilane, octyl trimethoxy silane, dodecyltrimethoxysilane, dimethyl diethoxy
Silane, dimethyldimethoxysil,ne, r- methyl allyl acyloxypropyl trimethoxysilane, r- methacryloxypropyl (three
Methylsiloxane) silane, r- aminopropyl triethoxysilane and r- epoxy and one of bring disaster to propyl trimethoxy silicane or
Any two kinds and two or more combinations.
The catalyst is dibutyl tin dilaurate, dibutyl diester acid tin, tin octoate, stannous iso caprylate, dioctyl
Oxalic acid tin, maleic acid mono octyl ester dioctyl tin, Kunshun butene two acid mono-character ester dibutyl tin, dibutyl diethyl tin octoate or
Diethyl caproic acid stannous.
The solvent is one of chain alcohols material, Ester and chain hydrocarbon substance or two or three any,
Chain alcohols material be methanol, ethyl alcohol or isopropanol, Ester be ethyl acetate, butyl acetate, ethyl acetate or butyl acetate,
Chain hydrocarbon substance is aliphatic hydrocarbon, aromatic hydrocarbon or low smell isoparaffin.
A kind of preparation method of fluorine-containing organic silicon stone protective agent, comprising the following steps:
0.1~10 parts by weight alkoxysilane mixture, 1~20 parts by weight fluorochemical, 0.1~10 parts by weight are organic poly-
Siloxanes is added sequentially in the reaction kettle for being equipped with 60~100 parts by weight solvent, is stirred 5~30min, is obtained mixed liquor；
The silane coupling agent of 0.1~30 parts by weight is added in mixed liquor, 5~30min is stirred, forms premix；
The catalyst of 0~1 parts by weight is eventually adding in premix, 5~30min of stirring carries out aging reaction to get to containing
Fluorine organic silicon stone protective agent.
Fluorochemical is introduced into organosilicon protective agent by the present invention is applied to stone protector, has both kept stone material good
Waterproofness, weatherability, have the characteristics that good resistance to oil stains, solve organosiloxane protective agent intolerant to the defect of greasy dirt,
And cost is reasonable.The micropore of stone surface is penetrated under solvent drive, as the solvent evaporates, fluorine-silicon copolymer object is in substrate
It is precipitated on hole wall and forms the extremely low protective film of surface tension.Whole-fluoroalkyl chain segment in protective film is enriched under thermodynamics driving
It is in orientation structure in coating surface, assigns stone material excellent oil-stain-preventing and waterproofness.Meanwhile alkoxy silane, silane
In methoxy group hydrolyze to form silanol in water, and cross-linking reaction further has occurred with the hydroxyl of stone surface, is formed
The high silicon oxygen bond of bond energy, therefore the adhesion strength between fluorine-silicon copolymer object and substrate is increased, it can effectively protect for a long time
Stone material is protected, the durability of stone protector is improved.And the fluorochemical ratio that protective agent of the present invention is added is less, Bu Hui great
Width increases overall cost, and marketing is strong.
Specific embodiment
To further understand the features of the present invention, technological means and specific purposes achieved, function, lower mask
Present invention is further described in detail for body embodiment.
Embodiment 1
A kind of fluorine-containing organic silicon stone protective agent is made of: alkoxysilane mixture following component in parts by weight
0.1 part；1 part of fluorochemical；0.1 part of organopolysiloxane；0.1 part of silane coupling agent；0.1 part of catalyst；60 parts of solvent.
Wherein, alkoxysilane mixture is the silane low polymer with reaction active groups of low molecular weight.Containing fluorination
It closes object and refers to the perfluoroalkoxy polymer long containing fluorocarbon chain.Organopolysiloxane refers to hydrosilicon Functional siloxane.
Silane coupling agent is methyltriethoxysilane.Catalyst is dibutyl tin dilaurate.Solvent is chain alcohols material, for example is
Methanol, ethyl alcohol or isopropanol.
It is first that 0.1 parts by weight alkoxysilane mixture, 1 parts by weight fluorochemical, 0.1 parts by weight are organic when preparation
Polysiloxanes is added sequentially in the reaction kettle for being equipped with 60 parts by weight solvent, is stirred 5min, is obtained mixed liquor.
The methyltriethoxysilane of 0.1 parts by weight is added in mixed liquor again, stirs 5min, forms premix.
Finally the dibutyl tin dilaurate of 0.1 parts by weight is added in premix, stirring 5min carries out aging reaction,
Obtain fluorine-containing organic silicon stone protective agent.
Embodiment 2
A kind of fluorine-containing organic silicon stone protective agent is made of: alkoxysilane mixture following component in parts by weight
10 parts；20 parts of fluorochemical；10 parts of organopolysiloxane；30 parts of silane coupling agent；1 part of catalyst；100 parts of solvent.
Wherein, alkoxysilane mixture is the siloxane oligomer with reaction active groups of low molecular weight.It is fluorine-containing
Compound refers to the perfluoroalkoxy polymer long containing fluorocarbon chain.Organopolysiloxane refers to hydrosilicon functionality silicon oxygen
Alkane.Silane coupling agent is methyltrimethoxysilane.Catalyst is dibutyl diester acid tin.Solvent is Ester, for example is
Ethyl acetate, butyl acetate, ethyl acetate, butyl acetate.
It is first that 10 parts by weight alkoxysilane mixtures, 20 parts by weight fluorochemicals, 10 parts by weight are organic poly- when preparation
Siloxanes is added sequentially in the reaction kettle for being equipped with 100 parts by weight solvent, is stirred 30min, is obtained mixed liquor.
The methyltrimethoxysilane of 1 parts by weight is added in mixed liquor again, stirs 30min, forms premix.
Finally the dibutyl diester acid tin of 1 parts by weight is added in premix, stirring 30min carries out aging reaction, i.e.,
Obtain fluorine-containing organic silicon stone protective agent.
Implement 3
By 5 parts by weight alkoxysilane mixtures, 5 parts by weight fluorochemicals, 5 parts by weight organopolysiloxanes according to addition
Into the reaction kettle of 90 parts by weight solvent, 30min is stirred；The methyltriethoxysilane of 10 parts by weight is added to above-mentioned steps
In obtained mixed liquor, 15min is stirred, forms premixing；It is eventually adding the dibutyl tin dilaurate of 1 parts by weight, is stirred
15min obtains fluorine-containing organic silicon stone protective agent.
Example 4
By 0.1 parts by weight alkoxysilane mixture, 10 parts by weight fluorochemicals, 8 parts by weight organopolysiloxanes according to
It is added in the reaction kettle of 80 parts by weight solvent, stirs 15min；The ethyl trimethoxy silane of 20 parts by weight is added to above-mentioned
In the mixed liquor that step obtains, 10min is stirred, forms premixing；It is eventually adding the tin octoate of 0.5 parts by weight, 5min is stirred, obtains
To fluorine-containing organic silicon stone protective agent.
Example 5
By 5 parts by weight alkoxysilane mixtures, 10 parts by weight fluorochemicals, 0.1 parts by weight organopolysiloxane according to
It is added in the reaction kettle of 90 parts by weight solvent, stirs 15min.
The methyltrimethoxysilane of 15 parts by weight is added in the mixed liquor that above-mentioned steps obtain, stirs 10min, shape
At premixing；It is eventually adding the dibutyl diester acid tin of 0.5 parts by weight, 5min is stirred, obtains fluorine-containing organic silicon stone protective agent.
It should be noted that these are only the preferred embodiment of the present invention, it is not intended to restrict the invention, although ginseng
According to embodiment, invention is explained in detail, for those skilled in the art, still can be to aforementioned reality
Technical solution documented by example is applied to modify or equivalent replacement of some of the technical features, but it is all in this hair
Within bright spirit and principle, any modification, equivalent replacement, improvement and so on should be included in protection scope of the present invention
Within.
Claims (8)
1. a kind of fluorine-containing organic silicon stone protective agent, which is characterized in that the protective agent is by following group in parts by weight
Divide and constitute: 0.1~10 part of alkoxysilane mixture；1~20 part of fluorochemical；0.1~10 part of organopolysiloxane；Silane
0.1~30 part of coupling agent；0~1 part of catalyst；60~100 parts of solvent.
2. fluorine-containing organic silicon stone protective agent according to claim 1, which is characterized in that the alkoxysilane mixture
Refer to the silane/siloxane oligomer with reaction active groups of low molecular weight.
3. fluorine-containing organic silicon stone protective agent according to claim 1, which is characterized in that the fluorochemical, which refers to, to be contained
The perfluoroalkoxy polymer for having fluorocarbon chain long.
4. fluorine-containing organic silicon stone protective agent according to claim 1, which is characterized in that the organopolysiloxane refers to
Hydrosilicon Functional siloxane.
5. fluorine-containing organic silicon stone protective agent according to claim 1, which is characterized in that the silane coupling agent is methyl
Triethoxysilane, methyltrimethoxysilane, ethyl triethoxysilane, ethyl trimethoxy silane, propyl triethoxy
Silane, propyl trimethoxy silicane, butyl triethoxysilane, butyl trimethoxy silane, octyltri-ethoxysilane, octyl
Trimethoxy silane, dodecyltrimethoxysilane, dimethyl diethoxysilane, dimethyldimethoxysil,ne, r- first
Base acryloxypropyl trimethoxy silane, r- methacryloxypropyl (trimethicone) silane, three second of r- aminopropyl
Oxysilane and r- epoxy simultaneously one of bring disaster to propyl trimethoxy silicane or any two kinds and two or more combinations.
6. fluorine-containing organic silicon stone protective agent according to claim 1, which is characterized in that the catalyst is tin dilaurate
Dibutyl tin, dibutyl diester acid tin, tin octoate, stannous iso caprylate, dioctyl oxalic acid tin, maleic acid mono octyl ester two are pungent
Ji Xi, Kunshun butene two acid mono-character ester dibutyl tin, dibutyl diethyl tin octoate or diethyl caproic acid stannous.
7. fluorine-containing organic silicon stone protective agent according to claim 1, which is characterized in that the solvent is chain alcohols object
One of matter, Ester and chain hydrocarbon substance are two or three any, and chain alcohols material is methanol, ethyl alcohol or isopropyl
Alcohol, Ester be ethyl acetate, butyl acetate, ethyl acetate or butyl acetate, chain hydrocarbon substance be aliphatic hydrocarbon, aromatic hydrocarbon or
Low smell isoparaffin.
8. a kind of preparation method of fluorine-containing organic silicon stone protective agent, comprising the following steps:
0.1~10 parts by weight alkoxysilane mixture, 1~20 parts by weight fluorochemical, 0.1~10 parts by weight are organic poly-
Siloxanes is added sequentially in the reaction kettle for being equipped with 60~100 parts by weight solvent, is stirred 5~30min, is obtained mixed liquor；
The silane coupling agent of 0.1~30 parts by weight is added in mixed liquor, 5~30min is stirred, forms premix；
The catalyst of 0~1 parts by weight is eventually adding in premix, 5~30min of stirring carries out aging reaction to get to containing
Fluorine organic silicon stone protective agent.
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| CN110437734A (en) * | 2019-07-12 | 2019-11-12 | 厦门中思诺新材料有限公司 | A kind of nanometer perfluor stone protectant of novel oil-stain-preventing and preparation method thereof |
| CN110643251A (en) * | 2019-09-25 | 2020-01-03 | 华南理工大学 | Decorative stone protective agent based on fluorosilicone acrylic resin and preparation method thereof |
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