CN110628028B - Preparation and application of organic silicon modified cardanol polyglycidyl ether resin - Google Patents
Preparation and application of organic silicon modified cardanol polyglycidyl ether resin Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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 invention relates to an organic silicon modified cardanol polyglycidyl ether resin. The invention provides a high-temperature-resistant anticorrosive coating composition containing the organosilicon modified cardanol polyglycidyl ether. The cardanol is introduced into the main chain of the organic silicon resin, so that the cardanol has the heat resistance, weather resistance and flexibility of the organic silicon resin, and the properties of convenience in construction and the like caused by normal-temperature curing and high crosslinking, as well as the specific mechanical properties, chemical resistance and the like, are retained.
Description
Technical Field
The invention relates to cardanol polyglycidyl ether resin and a preparation method thereof.
The invention also relates to the organic silicon modified cardanol polyglycidyl ether resin and a preparation method thereof.
The invention also relates to a normal-temperature-cured high-temperature-resistant anticorrosive coating prepared from the organosilicon-modified cardanol polyglycidyl ether resin.
Background
Metal equipment operating at high temperature in marine or high-humidity environments is subject to thermal oxidation corrosion at high temperature, and is subject to corrosion prevention in liquid media, electrochemistry and the like at normal temperature when the equipment is stopped. Therefore, the coating needs to be protected from corrosion, and in a plurality of high-temperature-resistant corrosion prevention measures (new alloy, ion implantation, improved process, surface protection layer and the like), the organic coating has the functions of protection and decoration, and the coating process is simple and is a more common high-temperature-resistant corrosion prevention measure. CN200810023514.3 takes organosilicon modified polyurethane resin as a main film forming material, the surface of the film is dried at room temperature, and then the film is heated to 180-200 ℃ for post-curing treatment, the film is mainly used for heating equipment such as fireplaces, chimneys and the like, but the film has no corrosion prevention requirement on the coating, and has the functions of temperature resistance and decoration; CN200410014119.0 and CN201510944515.1 take organic silicon resin as a main film forming material, have high temperature resistance, and the curing method is self-drying at normal temperature, but the curing treatment is carried out after heating, and no surface corrosion resistance is introduced.
The high-temperature resistant protective coating is mostly required to be heated for secondary curing, the focus is on the problem of high-temperature resistant thermal oxidation, and the high-temperature resistant protective coating has various defects on the corrosion resistance.
Disclosure of Invention
The invention aims to provide an organosilicon modified cardanol polyglycidyl ether resin.
The invention also aims to provide a high-temperature-resistant anticorrosive coating composition containing the organosilicon modified cardanol polyglycidyl ether resin. The cardanol is introduced into the main chain of the organic silicon resin, so that the cardanol has the heat resistance, weather resistance and flexibility of the organic silicon resin, and the properties of convenience in construction and the like caused by normal-temperature curing and high crosslinking, as well as the specific mechanical properties, chemical resistance and the like, are retained.
The technical scheme of the invention is as follows
An organosilicon modified cardanol polyglycidyl ether epoxy phenolic resin has a structural formula shown as follows:
wherein n is an integer of 1 or more
The organic silicon modified cardanol polyglycidyl ether resin is synthesized by grafting cardanol polyglycidyl ether resin and organic silicon resin in the presence of a solvent and a catalyst.
The cardanol polyglycidyl ether resin is a resin with the following structure:
the preparation method of the cardanol polyglycidyl ether epoxy phenolic resin comprises the following steps:
mixing 50 parts of cardanol and 20 parts of formaldehyde under stirring, adding 1 part of benzyltriethylammonium chloride, reacting for 4-6 hours at 80-100 ℃, adding 40 parts of epichlorohydrin, mixing under stirring, heating to 60-80 ℃, dropwise adding 100 parts of 10% NaOH aqueous solution, reacting for 4-6 hours, washing to neutrality, filtering, heating, distilling water and excessive epichlorohydrin under reduced pressure, cooling to 40 ℃, discharging to obtain 100 parts of low-viscosity solution, namely the cardanol polyglycidyl ether resin.
The silicone resin is a silicone resin having the following structure:
wherein n is an integer of 1 or more and R is-CH3Or
The silicone resin of (4).
A method for preparing the organosilicon modified cardanol polyglycidyl ether resin with the epoxy resin comprises the following steps:
mixing cardanol polyglycidyl ether resin with an organic solvent under stirring to form liquid, and adding a catalyst and organic silicon resin. Reacting for 6-12 hours at 80-140 ℃, optimally 6-10 hours, cooling to 40 ℃, and discharging to obtain a low-viscosity solution, namely the organosilicon modified cardanol polyglycidyl ether resin.
The cardanol polyglycidyl ether resin and the organic silicon resin are in a weight ratio of 1: 3; accounting for 80 percent of the total feeding amount of the modified resin by weight.
The organic solvent may be ester, ketone or benzene solvent, such as ethyl acetate, butyl acetate, acetone, butanone, cyclohexanone, cyclopentanone, benzene, toluene or xylene. Most preferred is a solvent consisting of a mixture of xylene and cyclohexanone in a ratio of 4: 1. The amount used was 19% by weight of the total charge.
The catalyst is any one of dibutyltin dilaurate and stannous octoate, and the using amount is 1 weight percent of the total feeding amount.
The high-temperature-resistant anticorrosive coating composition consists of a primer and a finish, wherein the primer and the finish are composed of A, B bi-components, and is characterized by mainly comprising the organic silicon modified cardanol polyglycidyl ether resin, a curing agent, a pigment filler, an auxiliary agent and a proper amount of diluent. Based on 100 parts by weight of the modified organic silicon resin, the primer comprises the following components:
primer coating
The finish paint comprises the following components:
the modified curing agent is formed by mixing Wujiang resultant force WJ-1 curing agent and polyamide 115 curing agent in a ratio of 9: 1.
The dosage of the modified curing agent in the formula is controlled to be 4-8 parts by weight based on 100 parts by weight of the organosilicon modified cardanol polyglycidyl ether resin. The use amount is too high, and the curing agent part does not participate in the reaction, so that waste is caused, and the performance of the coating is influenced; too low a level, curing too slowly or not.
The coating of the invention is added with appropriate pigments and fillers according to specific application. The heat-resistant anticorrosive primer is prepared from anticorrosive pigments such as mica iron oxide, aluminum powder, aluminum tripolyphosphate and chromium oxide green, and fillers such as precipitated barium sulfate, glass flakes, mica powder and light calcium carbonate, wherein the pigments can be one or more than one. The total amount of the silicone resin is controlled to be 50 to 100 parts by weight based on 100 parts by weight of the silicone resin, depending on the physical and mechanical properties of the coating film. The heat-resistant anticorrosive finish paint is prepared from aluminum powder, graphite powder, carbon black and other pigments with shielding and heat-resistant functions, and precipitated barium sulfate, glass flakes, mica powder, light calcium carbonate and other fillers, and can be used in combination with one or more of the above. The total amount of the silicone resin is controlled to 40 to 80 parts by weight based on 100 parts by weight of the silicone resin, depending on the physical and mechanical properties of the coating film.
In order to prevent the paint from precipitating during transportation, storage and use, the thixotropic effect of the paint can be adjusted by adding organic bentonite or fumed silica, and the dosage of the primer is controlled to be 1-5 parts by weight based on 100 parts by weight.
The auxiliary agent is one or a mixture of more of defoaming agents; the defoaming agent is one or more of BYK-066N, BYK-028, AFCONA2720, AFCONA2723 and AFCONA2020, and the dosage is controlled to be 0.5-3 parts by weight based on 100 parts by weight of the organic silicon resin.
The solvent is xylene and cyclohexanone in a ratio of 4:1 part by weight of a mixed solvent
When the coating is used, the base coat and the finish coat are mixed according to the weight ratio of A to B (6-10) to 1, and the performance indexes of a coating film formed by brushing or spraying are as follows:
adhesion (grade): 1;
salt spray resistance: the coating does not foam, fall off or change color within 1000 hours;
high temperature resistance: the coating has no wrinkles, no bubbles and no falling after 240 hours at 500 ℃;
medium resistance: (seawater, saturated salt water, tap water, lubricating oil, engine oil and diesel oil) does not foam, fall off and rust after 3 months;
cold and heat alternation resistance: (500 ℃, 20 min; normal temperature sea water, 20min) for 20 cycles, and the paint film is unchanged.
The high-temperature-resistant anticorrosive coating can be applied to the fields of automobiles, ships, aviation, industrial equipment, chimneys, national defense and military industry and the like, and can be used as a high-temperature-resistant anticorrosive protection and decorative coating for high-temperature-resistant metal equipment in marine environment and high-humidity environment, such as engine parts, reaction kettle shells, chimneys, accessories or adjacent areas and the like.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope thereof
Example 1 preparation of Silicone-modified Cardanol polyglycidyl Ether resin
Mixing 60 parts of cardanol polyglycidyl ether resin and 15.2 parts of dimethylbenzene, adding 1 part of stannous octoate, 20 parts of organic silicon resin and 3.8 parts of cyclohexanone into the solution to stir and heat the solution, and reacting the solution for 8-10 hours at 80-100 ℃. 100 parts of transparent homogeneous viscous organosilicon modified cardanol polyglycidyl ether resin is obtained. Measured by infrared absorption spectroscopy at 1128cm-1、1095cm-1And 1022cm-1A characteristic absorption peak of silicon-oxygen bonds appears, and 3400cm-1And 1000cm-1The characteristic absorption peaks of the nearby carbon hydroxyl and silicon hydroxyl groups are weakened, and the corresponding target products are obtained through the synthesis reaction.
Example 2
100 parts of organosilicon modified cardanol polyglycidyl ether resin (example 1) and 100 parts of solvent are weighed, the mixture is put into a stainless steel tank and stirred by a high-speed stirrer, BYK066N0.5 parts of defoaming agent and 2.5 parts of organic bentonite as thixotropic agent are added, 40 parts of mica iron oxide, 15 parts of aluminum powder, 20 parts of aluminum tripolyphosphate, 15 parts of precipitated barium sulfate and 10 parts of light calcium carbonate are added after the mixture is uniformly stirred with the resin, the mixture is uniformly stirred, then the mixture is ground to standard fineness by a sand mill or a three-roll grinder, and the mixture is filtered and packaged to be a coating A component.
8.2 parts of WJ-1 curing agent, 0.8 part of polyamide 115 curing agent and 25 parts of solvent are weighed and uniformly stirred to obtain a component B of the coating.
When in use, A, B is prepared from two components according to the weight ratio of 9:1, spraying after uniformly mixing, and curing at normal temperature for seven days to obtain the high-temperature-resistant anticorrosive primer coating.
Example 3
100 parts of organosilicon modified cardanol polyglycidyl ether resin (example 1) and 50 parts of solvent are weighed, the mixture is put into a stainless steel tank and stirred by a high-speed stirrer, defoamer BYK 0281 parts and thixotropic agent 1 part of organic bentonite are added, the mixture is uniformly stirred with the resin, then 30 parts of chromium oxide green, 5 parts of aluminum powder, 5 parts of aluminum tripolyphosphate, 5 parts of precipitated barium sulfate and 5 parts of mica powder are added, the mixture is uniformly stirred, ground to a standard fineness by a sand mill or a three-roll grinder, and filtered and packaged into a coating A component.
3.6 parts of WJ-1 curing agent, 0.4 part of polyamide 115 curing agent and 20 parts of solvent are weighed and uniformly stirred to obtain a component B of the coating.
When in use, A, B is prepared from two components according to the weight ratio of 8: 1, spraying after uniformly mixing, and curing at normal temperature for seven days to obtain the high-temperature-resistant anticorrosive primer coating.
Example 4
100 parts of organosilicon modified cardanol polyglycidyl ether resin (example 1) and 75 parts of solvent by weight are weighed, the mixture is put into a stainless steel tank and stirred by a high-speed stirrer, defoamer AFCONA 27203 parts by weight and thixotropic agent 5 parts by weight of organobentonite are added, the mixture is uniformly stirred with the resin, 35 parts by weight of aluminum powder, 20 parts by weight of aluminum tripolyphosphate, 15 parts by weight of glass flakes and 10 parts by weight of mica powder are added, the mixture is uniformly stirred, then the mixture is ground to standard fineness by a sand mill or a three-roll mill, and the mixture is filtered and packaged to be a coating A component.
5.4 parts of WJ-1 curing agent, 0.6 part of polyamide 115 curing agent and 20 parts of solvent are weighed and uniformly stirred to obtain a component B of the coating.
When in use, the A, B components are mixed according to the weight ratio of 10: 1, spraying after uniformly mixing, and curing at normal temperature for seven days to obtain the high-temperature-resistant anticorrosive primer coating.
Example 5
100 parts of organosilicon modified cardanol polyglycidyl ether resin (example 1) and 40 parts of solvent are weighed, the mixture is put into a stainless steel tank and stirred by a high-speed stirrer, antifoaming agents AFCONA27231 and AFCONA 20200.5 are added, thixotropic agents are 2 parts by weight of fumed silica, the mixture is uniformly stirred with the resin, 25 parts by weight of graphite powder, 5 parts by weight of aluminum powder, 10 parts by weight of precipitated barium sulfate and 5 parts by weight of mica powder are added, the mixture is uniformly stirred, ground to a standard fineness by a sand mill or a three-roll grinder, and the mixture is filtered and packaged to be a coating A component.
5.4 parts of WJ-1 curing agent, 0.6 part of polyamide 115 curing agent and 25 parts of solvent are weighed and uniformly stirred to obtain a component B of the coating.
When in use, A, B is prepared from two components according to the weight ratio of 6: 1, uniformly mixing, spraying, and curing at normal temperature for seven days to obtain the high-temperature-resistant anticorrosive finish coat.
Example 6
100 parts of organosilicon modified cardanol polyglycidyl ether resin modified organosilicon resin (example 1) and 80 parts of solvent are put into a stainless steel tank and stirred by a high-speed stirrer, a defoaming agent BYK066N3 parts by weight and a thixotropic agent which is fumed silica are added, after the components are uniformly stirred with the resin, 20 parts of carbon black, 20 parts of aluminum powder, 13 parts of glass flakes, 14 parts of precipitated barium sulfate and 12 parts of light calcium carbonate are added and uniformly stirred, then a sand mill or a three-roll mill is used for grinding the components to a standard fineness, and the components are filtered and packaged to form a coating A component.
8.2 parts of WJ-1 curing agent, 0.8 part of polyamide 115 curing agent and 21 parts of solvent are weighed and uniformly stirred to obtain a component B of the coating.
When in use, A, B is prepared from two components according to the weight ratio of 9:1, uniformly mixing, spraying, and curing at normal temperature for seven days to obtain the high-temperature-resistant anticorrosive finish coat.
The anticorrosion temperature-resistant primer in the embodiment 1 is matched with the anticorrosion temperature-resistant finishing paint in the embodiment 5 to obtain an anticorrosion temperature-resistant composite coating 1 which can be applied to high-temperature-resistant anticorrosion protection of surfaces of a chimney and a high-temperature-resistant construction; the anticorrosion temperature-resistant primer in the embodiment 2 is matched with the anticorrosion temperature-resistant finish paint in the embodiment 5 to obtain an anticorrosion temperature-resistant composite coating 2 which can be applied to anticorrosion protection of a reaction kettle running in a high-temperature and high-humidity environment; the anticorrosion temperature-resistant primer in the embodiment 3 is matched with the anticorrosion temperature-resistant finish paint in the embodiment 4 to obtain the anticorrosion temperature-resistant composite coating 3, which can be applied to anticorrosion protection of the surface of an engine running in a marine environment, and the performance indexes are shown in the table I.
Comparative example 1 a silicone high temperature resistant anticorrosive coating prepared from silicone resin, curing agent, pigment and filler, auxiliary agent and solvent as described in patent CN200710144426.4 is compared with the examples, as shown in table one.
Comparative example 2 a silicone high temperature resistant coating prepared from silicone resin, pigment and filler and solvent as described in patent CN200410014119.0 was compared with the examples, as in table one.
Watch 1
As can be seen from the table I, the composite coating prepared from the composition of the organosilicon modified cardanol polyglycidyl ether resin, the anti-corrosion filler, the pigment filler, the auxiliary agent and the curing agent has excellent performances of high temperature resistance, corrosion resistance, medium resistance and the like.
As can be seen from the experiments of comparative examples 1 and 2, the high-temperature-resistant anticorrosive coating prepared from the organic silicon resin (modified organic silicon resin), the curing agent, the pigment, the filler, the auxiliary agent and the solvent has different performance indexes from the anticorrosive and temperature-resistant composite performance of the invention when tested under the same conditions.
Claims (12)
1. A preparation method of organosilicon modified cardanol polyglycidyl ether resin is characterized by comprising the following steps: mixing cardanol polyglycidyl ether resin with an organic solvent under stirring, adding a catalyst and organic silicon resin, reacting for 6-12 hours at 80-140 ℃, cooling to 40 ℃, discharging to obtain a low-viscosity solution, namely organic silicon modified cardanol polyglycidyl ether resin, wherein the cardanol polyglycidyl ether resin is prepared by the following method: mixing 50 parts of cardanol and 20 parts of formaldehyde under stirring, adding 1 part of benzyltriethylammonium chloride, reacting for 4-6 hours at 80-100 ℃, adding 40 parts of epoxy chloropropane, mixing under stirring, heating to 60-80 ℃, dropwise adding 100 parts of 10% NaOH aqueous solution, reacting for 4-6 hours, washing to neutrality, filtering, heating and distilling under reduced pressure to obtain water and excessive epoxy chloropropane, cooling to 40 ℃, discharging to obtain a low-viscosity solution, namely cardanol polyglycidyl ether resin, and organic silicon modified cardanol polyglycidyl ether epoxy phenolic resin, wherein the structural formula of the cardanol polyglycidyl ether epoxy phenolic resin is as follows:
wherein n is an integer equal to or greater than 1; r is-CH3Or
The cardanol polyglycidyl ether resin is a resin with the following structure:
2. the preparation method of the organosilicon modified cardanol polyglycidyl ether resin according to claim 1, wherein a catalyst is added to react with the organosilicon resin for 6-10 hours.
3. The method for preparing the silicone modified cardanol polyglycidyl ether resin according to claim 1, wherein the proportion of the cardanol polyglycidyl ether resin to the silicone resin is 1:3 by weight; the cardanol polyglycidyl ether resin and the organic silicon resin account for 80 wt% of the total feeding amount.
4. The method for preparing the organosilicon modified cardanol polyglycidyl ether resin according to claim 1, wherein the organic solvent is an ester, ketone or benzene solvent, and the amount of the organic solvent is 19 wt% of the total amount of the added cardanol polyglycidyl ether resin.
5. The method for preparing the silicone-modified cardanol polyglycidyl ether resin according to claim 4, wherein the organic solvent is ethyl acetate, butyl acetate, acetone, butanone, cyclohexanone, cyclopentanone, or benzene, toluene, or xylene.
6. The method of claim 1, wherein the catalyst is selected from the group consisting of dibutyl tin dilaurate and stannous octoate, and the amount of the catalyst is 1 wt% of the total amount charged.
7. A high-temperature-resistant anticorrosive coating composition is characterized by comprising a primer and a finish, wherein the primer and the finish are composed of A, B bi-components, the composition comprises the organosilicon modified cardanol polyglycidyl ether resin as defined in claim 1, and the content of each component of the primer is as follows in parts by weight:
primer coating
B component
Modified curing agent 4-8
20-26 parts of solvent
The finish paint comprises the following components:
b component
Modified curing agent 4-8
20-26 parts of solvent.
8. The high-temperature-resistant anticorrosive coating composition according to claim 7, wherein the modified curing agent is a mixture of Wujiang Konjac WJ-1 curing agent and polyamide 115 curing agent in a ratio of 9: 1.
9. The high temperature resistant anticorrosive coating composition according to claim 7, wherein the solvent is a mixture of xylene and cyclohexanone in a ratio of 4: 1.
10. The high-temperature-resistant anticorrosive coating composition according to claim 7, wherein the primer is pigment selected from at least one of mica iron oxide, aluminum powder, aluminum tripolyphosphate and chromium oxide green, and filler selected from at least one of precipitated barium sulfate, glass flakes, mica powder and light calcium carbonate; the finish paint selects more than one of aluminum powder, graphite powder and carbon black as pigment, and more than one of precipitated barium sulfate, glass flake, mica powder and light calcium carbonate as filler.
11. The high temperature resistant anticorrosive coating composition according to claim 7, wherein the thixotropic agent is organobentonite or fumed silica.
12. An organosilicon modified cardanol polyglycidyl ether resin obtained by the method for preparing an organosilicon modified cardanol polyglycidyl ether resin according to claim 1.
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| CN102101964A (en) * | 2011-01-06 | 2011-06-22 | 杭州油漆有限公司 | Organic silicon modified epoxy heat-resistant and anti-corrosive coating and preparation method thereof |
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