KR20160110052A - A dimethylolpropionic acid modified waterborne phenolic resin - Google Patents
A dimethylolpropionic acid modified waterborne phenolic resin Download PDFInfo
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- KR20160110052A KR20160110052A KR1020150162012A KR20150162012A KR20160110052A KR 20160110052 A KR20160110052 A KR 20160110052A KR 1020150162012 A KR1020150162012 A KR 1020150162012A KR 20150162012 A KR20150162012 A KR 20150162012A KR 20160110052 A KR20160110052 A KR 20160110052A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/32—Chemically modified polycondensates by organic acids or derivatives thereof, e.g. fatty oils
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- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
Description
The present invention relates to the field of chemical coatings and, more particularly, to dimethylolpropionic acid-modified water-soluble phenolic resin for making a water-borne coating and a method of making the same.
Phenol resin is a resin which is generally produced through high-temperature polymerization of petroleum oil, petroleum phthalate, glycerol, pentaerythritol and 200 # solvent petrol, and is characterized by excellent weatherability , Which has many VOC emissions and low safety factors during use and transportation, has flammability and explosion during use and transportation and belongs to toxic chemicals with large environmental pollution and is designated as a domestic exclusion product.
SUMMARY OF THE INVENTION The object of the present invention is to solve the problems of the prior art, and to provide a modified water-soluble phenolic resin and a method for producing the same.
In the first embodiment, by weight ratio,
Flaxseed oil 70 to 90
Maleic anhydride 10-30
Dongyu 30 ~ 40
Polyol 10-20
Potassium hydroxide 0.005 to 0.01
Phthalic anhydride 20-30
Dimethylol propionic acid 8-15
Benzoic acid 5 to 10
Butyl ether 30 to 50
there is provided a dimethylolpropionic acid-modified water-soluble phenolic resin containing 5 to 15 n-butanol.
According to one embodiment of the present invention, the polyol is pentaerythritol and / or glycerol.
According to an embodiment of the present invention, the dimethylolpropionic acid-modified water-soluble phenolic resin may contain, as a weight ratio, flaxseed oil 80, maleic anhydride 20, ternary oil 33, pentaerythritol 13, potassium hydroxide 0.008, phthalic anhydride 25, Dimethylol propionic acid 12, benzoic acid 7, butyl ether 40, and n-butanol 10.
According to an embodiment of the present invention, the dimethylolpropionic acid-modified water-soluble phenolic resin may be selected from the group consisting of flaxseed oil 70, maleic anhydride 10, toughener 30, glycerol 10, potassium hydroxide 0.005, phthalic anhydride 20, dimethylol Propionic acid 8, benzoic acid 5, butyl ether 30, and n-butanol 15.
According to an embodiment of the present invention, the dimethylolpropionic acid-modified water-soluble phenolic resin may contain, as a weight ratio, flaxseed oil 80, maleic anhydride 20, ternary oil 33, glycerol 13, potassium hydroxide 0.008, phthalic anhydride 25, Propionic acid 12, benzoic acid 7, butyl ether 40, and n-butanol 10.
According to an embodiment of the present invention, the dimethylolpropionic acid-modified water-soluble phenolic resin may contain, as a weight ratio, flaxseed oil 90, maleic anhydride 30, toughened oil 40, glycerol 20, potassium hydroxide 0.001, phthalic anhydride 30, dimethylol Propionic acid 15, benzoic acid 10, butyl ether 50, and n-butanol 5.
According to one embodiment of the present invention, the dimethylolpropionic acid-modified water-soluble phenolic resin is prepared by the following method:
Step 1: Mixing flaxseed oil and maleic anhydride at room temperature, heating to 240 to 250 ° C and obtaining a first product by cooling for 7 to 9 hours;
Step 2: mixing the oil, the polyol and the potassium hydroxide, heating to 240 to 250 캜, and allowing to stand for 1 to 1.5 hours;
Step 3: The product obtained from Step 2 is cooled to 170 to 190 占 폚, phthalic anhydride, dimethylolpropionic acid and benzoic acid are added, heated to 170 to 190 占 폚, and refluxed with xylene for 0.5 to 1.5 hours, Heating to 200 ° C to 210 ° C and standing for 6 to 8 hours to obtain a second product;
Step 4: To obtain a water-soluble phenolic resin, the first product is mixed with butyl ether, n-butanol, the second product is added, and the pH of the mixture is adjusted to 8.5 - 9 < / RTI >
The water-soluble phenolic resin of the present invention does not contain benzene, reduces VOC emissions, has a high safety factor during transportation and use; It not only meets the technical requirements of oleoresin, but also has improved safety and environmental friendliness, and thus is substantially safe and environmentally friendly.
Various other advantages and benefits of the present invention will become apparent to those skilled in the art upon a reading of the following detailed description of the preferred embodiments.
The accompanying drawings are used to show only preferred embodiments, but are not meant to be limiting;
BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 shows a flow chart of a process for producing dimethylolpropionic acid-modified water-soluble phenolic resin in the present invention.
The present invention provides several applicable creative concepts that can be implemented substantially in context.
The following specific examples set forth herein are illustrative and not intended to be limiting.
Hereinafter, the present invention will be described in more detail with reference to the accompanying drawings and embodiments.
In the first embodiment, the dimethylol propionic acid-modified water-soluble phenol resin is used in a weight ratio,
Flaxseed oil 70 to 90
Maleic anhydride 10-30
Dongyu 30 ~ 40
Polyol 10-20
Potassium hydroxide 0.005 to 0.01
Phthalic anhydride 20-30
Dimethylol propionic acid 8-15
Benzoic acid 5 to 10
Butyl ether 30 to 50
butanol 5-15.
Here, the polyol used in the present invention may be a triol and / or a tetraol such as pentaerythritol, glycerol or a mixture thereof.
According to a second embodiment, a method for producing a water-soluble phenolic resin is provided, and Fig. 1 shows a flow chart of a method for producing a water-soluble phenolic resin in the present invention. As shown in Fig. 1, the manufacturing method comprises:
Step 1: 70 to 90 parts by weight of flaxseed oil at room temperature and 10 to 30 parts by weight of maleic anhydride are mixed, heated to 240 to 250 DEG C, and allowed to stand for 7 to 9 hours to obtain a first product;
Step 2: mixing 30 to 40 parts by weight of the oil, 10 to 20 parts by weight of the polyol, and 0.005 to 0.01 part by weight of potassium hydroxide, heating to 240 to 250 占 폚 and standing for 1 to 1.5 hours;
Step 3: The product obtained from Step 2 is cooled to 170 to 190 DEG C, 20 to 30 parts by weight of phthalic anhydride, 8 to 15 parts by weight of dimethylolpropionic acid and 5 to 10 parts by weight of benzoic acid are added, Heating and refluxing the xylene over a period of 0.5 to 1.5 hours, heating to 200 ° C to 210 ° C and standing for 6 to 8 hours to obtain a second product;
Step 4: To obtain a water-soluble phenol resin, 30 to 50 parts by weight of butyl ether and 5 to 15 parts by weight of n-butanol are mixed with the first product, the second product is added, and the temperature is reduced to 95 to 105 DEG C , Adding an amine neutralizing agent so that the pH of the mixture becomes 8.5-9.
In the above step 2, the alcoholysis reaction is carried out at 240 ° C to 250 ° C.
The ethanol antioxidant determination method can be adapted to determine the end point of the alcoholysis reaction, and certain operations are as follows: take the reaction product in step 2, mix with 95% ethanol at a volume ratio of 1: 5 at 25 캜, Is transparent indicates that the end point of the alcohol reaction is reached.
In step 4, the amine neutralizing agent is added so that the pH of the final product is 8.5-9 to adjust the pH of the resin.
The amine neutralizer applied may be a product such as triethylamine or MPA-95, and the amount of the amine neutralizer added is 5 to 10 parts by weight.
Here, the chemical name of AMP-95 is 2-amino-2-methyl-1-propanol which is a polyfunctional amine additive and can adjust the pH of the emulsion adhesive to reach a steady state, Dispersive effect, which is advantageous at each stage of the entire service life cycle of the coating, including manufacturing, storage, transportation, use and final shots.
The process according to the invention also comprises a step 5 of adding water to dilute the water-soluble phenolic resin obtained,
Adding water to dilute the water-soluble phenolic resin, wherein the total amount of water added can be adjusted according to the resin solids required for production.
The dilution process makes ready prepared water-soluble phenolic resin easier to store and subsequent use.
Based on the water-soluble phenolic resin of the present invention and a method for producing the same, various configurations can be selected, and various embodiments can be designed. Accordingly, the specific embodiments disclosed herein are by way of example and not of limitation. For the detailed description of the present invention, the following examples are selected and described.
Example 1
In this embodiment, the water-soluble phenol resin is selected from the group consisting of flaxseed oil 70, maleic anhydride 10, toughener 30, pentaerythritol 10, potassium hydroxide 0.005, phthalic anhydride 20, dimethylolpropionic acid 8, benzoic acid 5, Ether 30, and n-butanol 15.
In this example, the process for preparing a phenolic resin comprises:
Step 1: Mixing flaxseed oil and maleic anhydride at room temperature, heating to 240 占 폚 and standing for 7 hours to obtain a first product;
Step 2: In order to carry out the alcoholysis reaction, the steps of mixing the oil, pentaerythritol and potassium hydroxide, heating to 240 DEG C and allowing to stand for 1 hour;
Step 3: The alcohol decomposition product obtained from Step 2 was cooled to 170 DEG C, phthalic anhydride, dimethylolpropionic acid and benzoic acid were added, heated to 170 DEG C and kept at rest for 0.5 hour while being refluxed in xylene, Lt; / RTI > to obtain a second product;
Step 4: To obtain a water-soluble phenolic resin, the first product is mixed with butyl ether, n-butanol, the second product is added, and the pH of the mixture is adjusted to 8.5 to 9 when the temperature is reduced to 95 ° C. , And 8 parts by weight of triethylamine;
Step 5: In order to obtain the resin solids required for production, an appropriate amount of tap water is added to the water-soluble phenolic resin, and barreling is carried out.
Example 2
In the present embodiment, the phenol resin in the weight ratio is selected from the group consisting of flaxseed oil 90, maleic anhydride 30, tung oil 40, pentaerythritol 20, potassium hydroxide 0.01, phthalic anhydride 30, dimethylol propionic acid 15, benzoic acid 10, butyl ether 50, It contains n-butanol 5.
In this example, the manufacturing method of the phenolic resin is the same as that of the first embodiment.
Example 3
In this embodiment, the phenolic resin is selected from the group consisting of flaxseed oil 80, maleic acid 20, ternary oil 33, pentaerythritol 13, potassium hydroxide 0.008, anhydrous phthalic acid 25, dimethylolpropionic acid 12, benzoic acid 7, - butanol 10.
In this example, the manufacturing method of the phenol resin is the same as that of the first embodiment.
Example 4
In the present embodiment, the phenol resin is used in a weight ratio of: flaxseed oil 70, maleic acid 10, tung oil 30, glycerol 10, potassium hydroxide 0.005, anhydrous phthalic acid 20, dimethylolpropionic acid 8, benzoic acid 5, butyl ether 30, n- 15 < / RTI >
In this example, the process for preparing a phenolic resin comprises:
Step 1: Mixing flaxseed oil and maleic anhydride at room temperature, heating to 250 占 폚 and standing for 8 hours to obtain a first product;
Step 2: mixing the oil, glycerol and potassium hydroxide to effect the alcoholysis reaction, heating to 245 DEG C and allowing to stand for 1.5 hours;
Step 3: The alcohol decomposition product obtained from Step 2 was cooled to 180 占 폚, phthalic anhydride, dimethylolpropionic acid and benzoic acid were added, heated to 180 占 폚 and left to stand for 1 hour while being refluxed in xylene, Lt; / RTI > to obtain a second product;
Step 4: To obtain a water-soluble phenolic resin, the first product is mixed with butyl ether, n-butanol, the second product is added, and the pH of the mixture is adjusted to 8.5 to 9 , And 10 parts by weight of triethylamine;
Step 5: In order to obtain the resin solid content necessary for production, it includes the step of adding an appropriate amount of tap water to the water-soluble phenol resin and barreling.
Example 5
In this embodiment, phenol resin is used in a weight ratio of: flaxseed oil 80, maleic anhydride 20, ternary oil 33, glycerol 13, potassium hydroxide 0.008, anhydrous phthalic acid 25, dimethylolpropionic acid 12, benzoic acid 7, butyl ether 40, n- Butanol 10.
In this example, the production method of the phenol resin is the same as that of the fourth embodiment.
Example 6
In this embodiment, the phenolic resin is selected from the group consisting of flaxseed oil 90, maleic anhydride 30, toughened oil 40, glycerol 20, potassium hydroxide 0.01, anhydrous phthalic acid 30, dimethylolpropionic acid 15, benzoic acid 10, butyl ether 50, n- Contains butanol 5.
In this example, the production method of the phenol resin is the same as that of the fourth embodiment.
Example 7
In this embodiment, phenol resin is used in a weight ratio of: flaxseed oil 80, maleic anhydride 20, ternary oil 33, glycerol and pentaerythritol mixture 13, potassium hydroxide 0.008, phthalic anhydride 25, dimethylolpropionic acid 12, benzoic acid 7, butyl ether 40 , n-butanol 10.
In this example, the process for preparing a phenolic resin comprises:
Step 1: Mixing flaxseed oil and maleic anhydride at room temperature, heating to 245 占 폚 and standing for 9 hours to obtain a first product;
Step 2: Mixing the oil, glycerol and pentaerythritol and potassium hydroxide to effect the alcoholysis reaction, heating to 245 DEG C and allowing to stand for 1 hour;
Step 3: The alcohololysis product obtained from Step 2 was cooled to 190 DEG C, phthalic anhydride, dimethylolpropionic acid and benzoic acid were added, heated to 190 DEG C and refluxed with xylene while standing for 1.5 hours, heated to 205 DEG C and heated for 8 hours Lt; / RTI > to obtain a second product;
Step 4: The first product is mixed with butyl ether, n-butanol, the second product is added, and when the temperature is reduced to 105 ° C, 5 parts by weight of triethylamine are added and the mixture is brought to a pH of 8.5 to 9 To obtain a water-soluble phenolic resin;
Step 5: In order to obtain the resin solid content necessary for production, it includes the step of adding an appropriate amount of tap water to the water-soluble phenol resin and barreling.
Example 8
In this embodiment, the phenolic resin is selected from the group consisting of flaxseed oil 90, maleic anhydride 30, toughened oil 40, glycerol and pentaerythritol mixture 20, potassium hydroxide 0.01, phthalic anhydride 30, dimethylolpropionic acid 15, benzoic acid 10, butyl ether 50, and n-butanol 5.
In this example, the manufacturing method of the phenol resin is the same as that of the Embodiment 7.
Example 9
In the present embodiment, the phenol resin in the weight ratio is selected from the group consisting of flaxseed oil 70, maleic anhydride 10, toughened oil 30, glycerol and pentaerythritol mixture 10, potassium hydroxide 0.05, phthalic anhydride 20, dimethylolpropionic acid 8, benzoic acid 5, Ether 30, and n-butanol 15.
In this example, the manufacturing method of the phenol resin is the same as that of the Embodiment 7.
The applicant senses the appearance, color, gloss, and acid value index of the water-soluble phenolic resin produced in Example 1, and the specific indices and actual detected values are shown in Table 1:
(Fe-Co method) / water
From the measurement data it can be seen that the water-soluble phenolic resin of the present invention has good quality and is superior in performance of oleoresin.
The measurement results of the other embodiments are similar to those of Table 1, and a description thereof will be omitted.
It should be noted that the embodiments described herein are presented by way of example only and are not meant to be limiting.
Those skilled in the art will recognize that many other alternative embodiments may be devised without departing from the spirit and scope of the appended claims.
The brackets, terms, descriptions, and numerical references between the numerical values used herein are merely exemplary in nature and are not meant to be limiting.
The word " comprising "does not exclude the presence of other elements or steps not listed in the claims.
Words such as " first, "" second," or " third, "
Claims (7)
Linseed oil 70-90
Maleic anhydride 10-30
Tung oil 30 ~ 40
Polyol 10 to 20
Potassium hydroxide 0.005 to 0.01
Phthalic anhydride 20-30
Dimethylolpropionic acid 8-15
Benzoic acid 5 to 10
Butyl ether 30 to 50
dimethylolpropionic acid modified waterborne phenolic resin characterized in that it contains n-butanol 5-15.
Wherein the polyol is pentaerythritol and / or glycerol. ≪ RTI ID = 0.0 > 11. < / RTI >
As a weight ratio, a mixture of flaxseed oil 80, maleic anhydride 20, ternary oil 33, pentaerythritol 13, potassium hydroxide 0.008, anhydrous phthalic acid 25, dimethylolpropionic acid 12, benzoic acid 7, butyl ether 40, Soluble phenol resin. ≪ RTI ID = 0.0 > 11. < / RTI >
As the weight ratio, there were used those containing flaxseed oil 70, maleic anhydride 10, tung oil 30, glycerol 10, potassium hydroxide 0.005, phthalic anhydride 20, dimethylol propionic acid 8, benzoic acid 5, butyl ether 30 and n-butanol 15 Dimethylol propionic acid-modified water-soluble phenolic resin.
As the weight ratio, there were used those containing flaxseed oil 80, maleic anhydride 20, ternary oil 33, glycerol 13, potassium hydroxide 0.008, phthalic anhydride 25, dimethylolpropionic acid 12, benzoic acid 7, butyl ether 40 and n-butanol 10 Dimethylol propionic acid-modified water-soluble phenolic resin.
As the weight ratio, those containing flaxseed oil 90, maleic anhydride 30, tung oil 40, glycerol 20, potassium hydroxide 0.001, phthalic anhydride 30, dimethylol propionic acid 15, benzoic acid 10, butyl ether 50 and n-butanol 5 Dimethylol propionic acid-modified water-soluble phenolic resin.
Step 2: mixing the oil, the polyol and the potassium hydroxide, heating to 240 to 250 캜, and allowing to stand for 1 to 1.5 hours;
Step 3: The product obtained in Step 2 is cooled to 170 to 190 DEG C, phthalic anhydride, dimethylolpropionic acid and benzoic acid are added, heated to 170 to 190 DEG C and refluxed with xylene for 0.5 to 1.5 hours, Heating to 210 DEG C and standing for 6 to 8 hours to obtain a second product;
Step 4: To obtain a water-soluble phenolic resin, the first product is mixed with butyl ether, n-butanol, the second product is added, the amine neutralizing agent is added when the temperature is reduced to 95 to 105 캜, Wherein the pH of the dimethylol propionic acid-modified water-soluble phenolic resin is 8.5 to 9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510100707.4A CN104629024A (en) | 2015-03-09 | 2015-03-09 | Dimethylolpropionic acid modified waterborne phenolic resin and preparation method thereof |
| CN201510100707.4 | 2015-03-09 |
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| Publication Number | Publication Date |
|---|---|
| KR20160110052A true KR20160110052A (en) | 2016-09-21 |
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| KR1020150157598A KR20160110050A (en) | 2015-03-09 | 2015-11-10 | A preparation method of dimethylolpropionic acid modified waterborne phenolic resin |
| KR1020150162012A KR20160110052A (en) | 2015-03-09 | 2015-11-18 | A dimethylolpropionic acid modified waterborne phenolic resin |
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| KR1020150157598A KR20160110050A (en) | 2015-03-09 | 2015-11-10 | A preparation method of dimethylolpropionic acid modified waterborne phenolic resin |
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| KR (2) | KR20160110050A (en) |
| CN (1) | CN104629024A (en) |
| DE (2) | DE102016103142A1 (en) |
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| CN105061707A (en) * | 2015-08-18 | 2015-11-18 | 湖州长盛化工有限公司 | Preparation method for dimethylolpropionic acid modified water-based phenolic resin |
| CN110041865A (en) * | 2019-04-12 | 2019-07-23 | 太尔化工（南京）有限公司 | A kind of agricultural cotton environmentally-friephenolic phenolic resin adhesive |
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| CN103319700A (en) * | 2013-07-12 | 2013-09-25 | 王芳贵 | Maleic anhydride oil modified aqueous alkyd resin, and environmentally-friendly paint prepared through using it |
| CN104086761B (en) * | 2014-06-05 | 2016-03-02 | 华南理工大学 | A kind of waterborne organic silicon modified alkyd resin and preparation method thereof |
| CN104262595A (en) * | 2014-09-16 | 2015-01-07 | 田清峰 | Water-based alkyd resin synthesis technique |
-
2015
- 2015-03-09 CN CN201510100707.4A patent/CN104629024A/en active Pending
- 2015-11-10 KR KR1020150157598A patent/KR20160110050A/en not_active Application Discontinuation
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2016
- 2016-02-23 DE DE102016103142.9A patent/DE102016103142A1/en not_active Withdrawn
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| CN104629024A (en) | 2015-05-20 |
| DE102016103139A1 (en) | 2016-09-15 |
| KR20160110050A (en) | 2016-09-21 |
| DE102016103142A1 (en) | 2016-09-15 |
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