CN102604117A - Preparation method and application of polyether-modified epoxy polysiloxane resin - Google Patents
Preparation method and application of polyether-modified epoxy polysiloxane resin Download PDFInfo
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- CN102604117A CN102604117A CN201210060050XA CN201210060050A CN102604117A CN 102604117 A CN102604117 A CN 102604117A CN 201210060050X A CN201210060050X A CN 201210060050XA CN 201210060050 A CN201210060050 A CN 201210060050A CN 102604117 A CN102604117 A CN 102604117A
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- polyether modified
- polyorganosiloxane resin
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Abstract
The invention discloses a preparation method and application of a polyether-modified epoxy polysiloxane resin. The method comprises the step of reacting polyether amine with an epoxy polysiloxane resin to obtain the polyether-modified epoxy polysiloxane resin, wherein a polyether amine molecule contains at least one primary ammine or secondary amine group, the molecular weight of polyether amine is from 200 to 2000, and the amount of polyether amine is 5-40% mass of the epoxy polysiloxane resin; the end group or side group of the main chain of the epoxy polysiloxane resin contains at least one epoxy group, or the end group and side group of the main chain of the epoxy polysiloxane resin contain at least one epoxy group, and the molecular weight of the epoxy polysiloxane resin is from 400 to 5000; and the reaction temperature of polyether amine and the epoxy polysiloxane resin is 50-90 DEG C, and the reaction time is 1-5 hours. The method is simple in process and high in production efficiency, and no byproducts are generated. The invention also discloses an epoxy polysiloxane paint composition prepared by the polyether-modified epoxy polysiloxane resin. The shock resistance of the composition is obviously improved, and the flexibility of the composition is improved, thereby prolonging the service life of paint. The paint composition is suitable for the heavy-duty anticorrosive fields of oceans, bridges and the like.
Description
Technical field
The invention belongs to paint field, be specifically related to a kind of preparation method of polyether modified epoxy polyorganosiloxane resin and the application in coating.
Background technology
The heavy-duty coating life-span that is used for large-scale steel structures such as offshore platform, bridge, this just needed the better coating of performance such as erosion resistance, stability to aging to satisfy these harsh requirements often more than 10 years.
In the heavy duty system field,, be difficult to satisfy the environmental requirement of increasingly stringent though the fluorocarbon coating excellent performance because it contains isocyanic ester, has adverse influence to human body.And polysiloxane coating materials is not owing to contain isocyanic ester, and high solids content is littler to the HUMAN HEALTH infringement, has excellent each item performance simultaneously and has obtained increasing application.Patent US 5618860, US 5275645 etc. have told about the preparation method and the application of epoxy polysiloxane coating.
It is not good that but the shortcoming of epoxy polysiloxane coating is a snappiness, is prone to crisp.In long use,, significantly reduce the work-ing life of coating thus because the coating internal stress is crossed and may well be caused coming off of filming.Propose among the patent US 7125609 to do the snappiness that solidifying agent improves epoxy polysiloxane coating with polyetheramine.But the polyethex amine modification effect of lower molecular weight is limited, and under the condition of self-vulcanizing, amino in the solidifying agent and epoxide group may not react fully, thereby influences linking of ehter bond and resin, and has finally influenced the raising of coating correlated performance.
The present invention is through shifting to an earlier date graft reaction with polyetheramine and epoxy polysiloxane resin; Ehter bond directly is linked on the epoxy polysiloxane resin through chemical bond; Can more effectively improve the snappiness of epoxy polysiloxane coating like this, show that impact resistance obviously improves.Epoxy polysiloxane coating shock-resistance through the preparation of this patent method is excellent, and snappiness increases, and the fragility of coating reduces, longer service life.Can better meet the requirement of large-scale steel structure heavy corrosion finish paints such as offshore platform atmospheric zone, oil tank, wind power plant, bridge spanning the sea, boats and ships.
Summary of the invention
The object of the invention is, provides a kind of technology simple, the preparation method of the polyether modified epoxy polyorganosiloxane resin that production efficiency is high.
The object of the invention also is, provides a kind of impact resistance good epoxy polysiloxane coating.
For realizing above-mentioned purpose, technical scheme provided by the present invention is:
A kind of preparation method of polyether modified epoxy polyorganosiloxane resin and application may further comprise the steps:
In the epoxy polysiloxane resin, add a certain amount of polyetheramine, under heating condition, fully mix, the reaction of process certain hour obtains the polyether modified epoxy polyorganosiloxane resin.
The epoxy polysiloxane resin is meant and is all containing at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain that its molecular weight is between 400-5000.Include but not limited to the SILIKOPON EF of Tego, the KF-101 of Shin-Etsu etc.
The consumption of polyetheramine accounts for the 5-40% of epoxy polysiloxane resin quality, and consumption is lower than 5% and is difficult to play the effect that increases shock-resistance, and content surpasses 40% and causes resin too soft, and hardness is lower.The molecular weight of polyetheramine is between 200-2000, preferably between 500-1500.Each polyetheramine molecule contains a primary amine or secondary amine group at least, preferably contains the polyetheramine of primary amine group.Include but not limited to the JEFFAMINE series polyetheramine of HUNTSMAN, like D-230, D-2000 etc.
The temperature of reaction of epoxy polysiloxane resin and polyetheramine is between 50-90 ℃, and the reaction times is 1-5 hour.
The polyether modified epoxy polyorganosiloxane resin that makes according to present method can be used as the filmogen of epoxy polysiloxane coating compsn, and its content accounts for 20～60% (wt) of epoxy polysiloxane coating compsn.
This epoxy polysiloxane coating compsn can comprise a certain amount of filler, like one of white titanium pigment, talcum powder, Magnesium Silicate q-agent, gypsum, lime carbonate, tiff, zeyssatite, clay, mica, iron mica, glass flake etc. or mixture.
This epoxy polysiloxane coating compsn can comprise a certain amount of auxiliary agent, like one or more mixtures in dispersion agent, flow agent, anti-settling agent, UV stablizer, wetting agent, thixotropic agent, softening agent, the skimmer.
This epoxy polysiloxane coating compsn can comprise certain amount of organic solvent, like one or more mixtures in aromatic hydrocarbons, alcohol, ether, ester, ether alcohol, the ketone.Preferred aromatic hydrocarbons and esters solvent, like toluene, YLENE, ETHYLE ACETATE, butylacetate etc.
In some embodiments, epoxy polysiloxane coating compsn of the present invention can also comprise tinting material, like pigment, dyestuff and toning agent.Pigment comprises mineral dye and pigment dyestuff, like carbon black, and yellow oxide of iron, phthalein viridescent, phthalocyanine blue etc.
The solidifying agent of epoxy polysiloxane coating compsn of the present invention is an aminosilane.
The general formula of said aminosilane is Y-Si-(O-X)
3, wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR)
a, a is 1～6 integer, R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base.Include but not limited to: aminoethyl aminopropyl triethoxysilane, aminoethyl aminomethyl phenyl Trimethoxy silane, γ-An Bingjisanjiayangjiguiwan, γ-aminopropyl methyl dimethoxysilane etc.Like the Z6020 of DOW CORNING, Z-6436; The A1100 of GE, A2100 etc.
The consumption of aminosilane is that ratio between the epoxy equivalent (weight) that makes in amino equivalent and the polyether modified epoxy polyorganosiloxane resin is between 0.8-1.2.Be lower than 0.8 and will make curing reaction incomplete, reduce the final performance of coating; Might to make coatingsurface " turning white " etc. occur bad apparent and surpass 1.2.
The prepared epoxy polysiloxane coating compsn according to the present invention, its coating method can be selected one or more bonded modes in dip-coating, roller coat, curtain coating, spraying, the brushing, makes the surface of base material form layer of even and films.
The prepared epoxy polysiloxane coating compsn according to the present invention; Its condition of cure is a room temperature condition; Like temperature is that 5～50 ℃, relative humidity are under 10%～80% the condition; Film and automatically solidify attached on the base material, making and forming a layer thickness on the surface of this base material is 20～60 microns protective membrane.
Advantage of the present invention is: preparing method's ME provided by the invention is simple, and production efficiency is high, does not have by product; Coating provided by the invention has the excellent in impact resistance ability, has reduced the internal stress of coating, increases the service life greatly.And at normal temperatures just can film-forming, easy to use, be particularly suitable for the requirement for anticorrosion of large scale industry steelwork such as offshore platform atmospheric zone, oil tank, wind power plant, bridge spanning the sea, boats and ships.
Below in conjunction with several embodiments, further specify the present invention.
Embodiment
First embodiment: at first prepare the polyether modified epoxy polyorganosiloxane resin.
With the epoxy polysiloxane resin of 100 grams, its molecular weight all contains at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain between 400-5000, be example with SILIKOPON EF.Join in the 250ml round-bottomed flask, be warmed up to 75 ℃, turn on agitator; Slowly drip the polyetheramine of 20 grams; Its molecular weight is between 200-2000, and each molecule contains a primary amine or secondary amine group at least, is example with JEFFAMINE THF-100; Reaction is 4 hours under 75 ℃ of conditions, obtains transparent thick polyether modified epoxy polyorganosiloxane resin.
The host T-01 for preparing epoxy polysiloxane coating with the polyether modified epoxy polyorganosiloxane resin that makes:
Polyether modified epoxy polyorganosiloxane resin 40 grams, white titanium pigment 25 grams, talcum powder 15 grams, aerosil 1 gram, dispersion agent 1 gram, skimmer 0.5 gram, flow agent 0.5 gram, YLENE 7 grams, butylacetate 10 grams.
The raw material of above each amount is dropped into respectively in the ball mill, and being ground to fineness is 20 μ m, and discharging promptly makes the host T-01 of epoxy polysiloxane coating.
Used solidifying agent is an aminosilane, and the general formula of aminosilane is Y-Si-(O-X) 3, and wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR) a, and a is 1～6 integer, and R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base; Aminosilane adopts the AMEO of Degussa in the present embodiment, and the consumption of aminosilane is that to make the ratio of the epoxy equivalent (weight) in amino equivalent and the polyether modified epoxy polyorganosiloxane resin be 1:1.
First Comparative Examples is that each material rate and preparation process are the same with the epoxy polysiloxane resin SILIKOPON EF coatings formulated C-01 that does not have modification.
Second embodiment at first prepares the polyether modified epoxy polyorganosiloxane resin.
With the epoxy polysiloxane resin of 100 grams, its molecular weight all contains at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain between 400-5000, be example with SILIKOPON EF.Join in the 250ml round-bottomed flask, be warmed up to 80 ℃, turn on agitator, slowly drip 20 the gram polyetheramine, its molecular weight is between 200-2000, each molecule contains a primary amine or secondary amine group at least, is example with JEFFAMINE SD-2001.Reaction is 5 hours under 80 ℃ of conditions, obtains transparent polyether modified epoxy polyorganosiloxane resin.
The host T-02 for preparing epoxy polysiloxane coating with the polyether modified epoxy polyorganosiloxane resin that makes:
Polyether modified epoxy polyorganosiloxane resin 50 grams, white titanium pigment 25 grams, talcum powder 10 grams, aerosil 1 gram, dispersion agent 1 gram, skimmer 0.5 gram, flow agent 0.5 gram, YLENE 7 grams, butylacetate 5 grams.
The raw material of above each amount is dropped into respectively in the ball mill, and being ground to fineness is 20 μ m, and discharging promptly makes the host T-02 of epoxy polysiloxane coating.
Used solidifying agent is an aminosilane, and the general formula of aminosilane is Y-Si-(O-X) 3, and wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR) a, and a is 1～6 integer, and R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base; Aminosilane adopts the AMEO of Degussa in the present embodiment, and the consumption of aminosilane is that to make the ratio of the epoxy equivalent (weight) in amino equivalent and the polyether modified epoxy polyorganosiloxane resin be 1:1.
Second Comparative Examples is that each material rate and preparation process are the same with the epoxy polysiloxane resin SILIKOPON EF coatings formulated C-02 that does not have modification.
The 3rd embodiment at first prepares the polyether modified epoxy polyorganosiloxane resin:
With the epoxy polysiloxane resin of 100 grams, its molecular weight all contains at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain between 400-5000, be example with SILIKOPON EF.Join in the 250ml round-bottomed flask, be warmed up to 75 ℃, turn on agitator, slowly drip 20 the gram polyetheramine, its molecular weight is between 200-2000, each molecule contains a primary amine or secondary amine group at least, is example with JEFFAMINE D-2000.Reaction is 3.5 hours under 75 ℃ of conditions, obtains transparent thick polyether modified epoxy polyorganosiloxane resin.
The host T-03 for preparing epoxy polysiloxane coating with the polyether modified epoxy polyorganosiloxane resin that makes:
Polyether modified epoxy polyorganosiloxane resin 60 grams, white titanium pigment 15 grams, talcum powder 10 grams, aerosil 1 gram, dispersion agent 1 gram, skimmer 0.5 gram, flow agent 0.5 gram, YLENE 5 grams, butylacetate 7 grams.
The raw material of above each amount is dropped into respectively in the ball mill, and being ground to fineness is 20 μ m, and discharging promptly makes the host T-03 of epoxy polysiloxane coating.
Used solidifying agent is an aminosilane, and the general formula of aminosilane is Y-Si-(O-X) 3, and wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR) a, and a is 1～6 integer, and R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base; Aminosilane adopts the AMEO of Degussa in the present embodiment, and the consumption of aminosilane is that to make the ratio of the epoxy equivalent (weight) in amino equivalent and the polyether modified epoxy polyorganosiloxane resin be 1:1.
The 3rd Comparative Examples is that each material rate and preparation process are the same with the epoxy polysiloxane resin SILIKOPON EF coatings formulated C-03 that does not have modification.
The 4th embodiment at first prepares the polyether modified epoxy polyorganosiloxane resin:
With the epoxy polysiloxane resin of 100 grams, its molecular weight all contains at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain between 400-5000, be example with SILIKOPON EF.Join in the 250ml round-bottomed flask, be warmed up to 70 ℃, turn on agitator, slowly drip 30 the gram polyetheramine, its molecular weight is between 200-2000, each molecule contains a primary amine or secondary amine group at least, is example with JEFFAMINE D-230.Reaction is 3.5 hours under 70 ℃ of conditions, obtains transparent polyether modified epoxy polyorganosiloxane resin.
The host T-04 for preparing epoxy polysiloxane coating with the polyether modified epoxy polyorganosiloxane resin that makes:
Polyether modified epoxy polyorganosiloxane resin 45 grams, white titanium pigment 15 grams, talcum powder 15 grams, aerosil 1 gram, dispersion agent 1 gram, skimmer 0.5 gram, flow agent 0.5 gram, YLENE 10 grams, butylacetate 12 grams.
The raw material of above each amount is dropped into respectively in the ball mill, and being ground to fineness is 20 μ m, and discharging promptly makes the host T-04 of epoxy polysiloxane coating.
Used solidifying agent is an aminosilane, and the general formula of aminosilane is Y-Si-(O-X) 3, and wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR) a, and a is 1～6 integer, and R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base; Aminosilane adopts the AMEO of Degussa in the present embodiment, and the consumption of aminosilane is that to make the ratio of the epoxy equivalent (weight) in amino equivalent and the polyether modified epoxy polyorganosiloxane resin be 1:1.
The 4th Comparative Examples is that each material rate and preparation process are the same with the epoxy polysiloxane resin SILIKOPON EF coatings formulated C-04 that does not have modification.
The 5th embodiment at first prepares the polyether modified epoxy polyorganosiloxane resin:
With the epoxy polysiloxane resin of 100 grams, its molecular weight all contains at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain between 400-5000, be example with SILIKOPON EF.Join in the 250ml round-bottomed flask, be warmed up to 65 ℃, turn on agitator, slowly drip 30 the gram polyetheramine, its molecular weight is between 200-2000, each molecule contains a primary amine or secondary amine group at least, is example with JEFFAMINE T-403.Reaction is 4 hours under 65 ℃ of conditions, obtains transparent thick polyether modified epoxy polyorganosiloxane resin.
The host T-05 for preparing epoxy polysiloxane coating with the polyether modified epoxy polyorganosiloxane resin that makes:
Polyether modified epoxy polyorganosiloxane resin 45 grams, white titanium pigment 15 grams, talcum powder 15 grams, aerosil 1 gram, dispersion agent 1 gram, skimmer 0.5 gram, flow agent 0.5 gram, YLENE 10 grams, butylacetate 12 grams.
The raw material of above each amount is dropped into respectively in the ball mill, and being ground to fineness is 20 μ m, and discharging promptly makes the host T-05 of epoxy polysiloxane coating.
Used solidifying agent is an aminosilane, and the general formula of aminosilane is Y-Si-(O-X) 3, and wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR) a, and a is 1～6 integer, and R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base; Aminosilane adopts the AMEO of Degussa in the present embodiment, and the consumption of aminosilane is that to make the ratio of the epoxy equivalent (weight) in amino equivalent and the polyether modified epoxy polyorganosiloxane resin be 1:1.
The 5th Comparative Examples is that each material rate and preparation process are the same with the epoxy polysiloxane resin SILIKOPON EF coatings formulated C-05 that does not have modification.
Of the above embodiment of the present invention, adopt technical characterictic same or similar and other preparation method and the coating that obtain, all in protection domain of the present invention with it.
Below be the The performance test results that adopts the inventive method to obtain, the test ground is the sandblast steel plate, and priming paint is epoxy zinc rich primer; Build is 40-50 μ m, and finish paint is an epoxy polysiloxane coating, and build is at 40-50 μ m; Drying conditions is 25 ℃; 50% relative humidity, be 7 days time of drying, carries out performance test after 7 days.The result is as shown in table 1.
Table 1 epoxy polysiloxane coating performance
Claims (7)
1. the preparation method of polyether modified epoxy polyorganosiloxane resin is characterized in that this method technological process is following:
In the epoxy polysiloxane resin, add a certain amount of polyetheramine, under heating condition, fully stir the mixture, can obtain the polyether modified epoxy polyorganosiloxane resin through after the reaction of certain hour.
2. the preparation method of polyether modified epoxy polyorganosiloxane resin according to claim 1; It is characterized in that; Described epoxy polysiloxane resin is meant and is all containing at least one epoxide group on the end group of polyorganosiloxane resin main chain or the side chain or on end group and the side chain that its molecular weight is between 400-5000.
3. the preparation method of polyether modified epoxy polyorganosiloxane resin according to claim 1; It is characterized in that; The consumption of described polyetheramine accounts for the 5-40% of epoxy polysiloxane resin quality; The molecular weight of polyetheramine is between 200-2000, and each molecule contains a primary amine or secondary amine group at least.
4. polyether modified epoxy polyorganosiloxane resin preparation method according to claim 1 is characterized in that, described temperature of reaction is between 50-90 ℃, and the reaction times is 1-5 hour.
5. the application of polyether modified epoxy polyorganosiloxane resin in coating; It is characterized in that; The polyether modified epoxy polyorganosiloxane resin is used to prepare the heavy duty system of offshore oil platform, bridge, petroleum storage tank, offshore wind farm tower, ship superstructure large-scale steel as the filmogen of epoxy polysiloxane coating.
6. the application of polyether modified epoxy polyorganosiloxane resin according to claim 5 in coating is characterized in that the polyether modified epoxy polyorganosiloxane resin accounts for the 20-60wt% of epoxy polysiloxane coating total amount.
7. the application of polyether modified epoxy polyorganosiloxane resin according to claim 5 in coating; It is characterized in that; Solidifying agent by the epoxy polysiloxane coating of polyether modified epoxy polyorganosiloxane resin preparation is an aminosilane; The general formula of aminosilane is Y-Si-(O-X) 3, and wherein, X is alkyl, hydroxyalkyl, alkoxyalkyl or the hydroxy alkoxy alkyl that is not more than 6 carbon atoms; Y is H (HNR) a, and a is 1～6 integer, and R is the organic group that is selected from aryl, alkyl, di alkylaryl, alkoxyalkyl or naphthenic base; The consumption of aminosilane be make the epoxy equivalent (weight) in amino equivalent and the polyether modified epoxy polyorganosiloxane resin ratio between 0.8-1.2.
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| CN111607065A (en) * | 2020-06-09 | 2020-09-01 | 中国人民解放军海军勤务学院 | Amphiphilic polymer material for propeller antifouling and anticorrosion and preparation method thereof |
| CN112592657A (en) * | 2020-12-14 | 2021-04-02 | 三棵树(上海)新材料研究有限公司 | Polysiloxane modified waterborne epoxy resin emulsion and preparation method thereof |
| CN113336953A (en) * | 2021-06-21 | 2021-09-03 | 宁波润禾高新材料科技股份有限公司 | Modified polyether amine, and preparation method and application thereof |
| CN114716912A (en) * | 2022-05-20 | 2022-07-08 | 信和新材料（苏州）有限公司 | High-temperature-resistant heat-dissipation coating and preparation method and application thereof |
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| CN114716912B (en) * | 2022-05-20 | 2022-11-15 | 信和新材料（苏州）有限公司 | High-temperature-resistant heat-dissipation coating and preparation method and application thereof |
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Application publication date: 20120725 |