CN116444747B - Synthesis method of resorcinol-itaconic acid-formaldehyde copolymer resin - Google Patents
Synthesis method of resorcinol-itaconic acid-formaldehyde copolymer resin Download PDFInfo
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- CN116444747B CN116444747B CN202310065459.9A CN202310065459A CN116444747B CN 116444747 B CN116444747 B CN 116444747B CN 202310065459 A CN202310065459 A CN 202310065459A CN 116444747 B CN116444747 B CN 116444747B
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- resorcinol
- itaconic acid
- formaldehyde
- copolymer resin
- reddish brown
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- -1 resorcinol-itaconic acid-formaldehyde Chemical compound 0.000 title claims abstract description 32
- 229920006026 co-polymeric resin Polymers 0.000 title claims abstract description 19
- 238000001308 synthesis method Methods 0.000 title claims abstract description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 68
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000011259 mixed solution Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000010438 heat treatment Methods 0.000 claims abstract description 19
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000000243 solution Substances 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 238000010992 reflux Methods 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 abstract description 21
- 239000000463 material Substances 0.000 abstract description 14
- 230000001070 adhesive effect Effects 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 6
- 239000002657 fibrous material Substances 0.000 abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 230000009257 reactivity Effects 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 239000000835 fiber Substances 0.000 description 14
- 239000008098 formaldehyde solution Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000010058 rubber compounding Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- STOSPPMGXZPHKP-UHFFFAOYSA-N tetrachlorohydroquinone Chemical compound OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl STOSPPMGXZPHKP-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Classifications
-
- 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 & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
The invention discloses a synthesis method of resorcinol-itaconic acid-formaldehyde copolymer resin, which comprises the following steps: firstly, itaconic acid is dissolved in formaldehyde aqueous solution to obtain mixed solution for standby; adding water and resorcinol into a four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, dropping the mixed solution obtained in the step 1 by using the dropping funnel for 0.5-1.5 h, heating for reaction, regulating the PH to 6.5-7.0 by using a NaOH solution, distilling under reduced pressure to remove water in the reaction system, obtaining reddish brown transparent viscous liquid, removing the reddish brown transparent resorcinol-itaconic acid-formaldehyde copolymer resin from the reactor while the reddish brown transparent viscous liquid is hot, and cooling. The molecular structure of the invention has phenolic hydroxyl and carboxyl, and has strong reactivity. Can effectively and accurately capture amine compounds, prevent the amine compounds from corroding polyester fiber materials, endow excellent chemical properties, and greatly improve the adhesive property of rubber and framework materials.
Description
Technical Field
The invention relates to a synthesis method of resorcinol-itaconic acid-formaldehyde copolymer resin.
Background
In recent years, the rapid development of cars, in particular electric cars, also brings unprecedented opportunities to the development of car tires. The car tyre is generally of a semisteel meridian structure, the main stream of skeleton materials is steel wires and polyester fiber cords, the polyester fiber is called PET fiber for short, and the chemical name is polyethylene terephthalate. The polyester cord has the advantages of excellent dimensional stability, high modulus, low shrinkage, good fatigue resistance, small creep, corrosion resistance, good heat resistance and the like, and is an excellent framework material of radial tires for cars. In the actual production of such tires, the bonding material of the rubber and the matrix material is generally a metaformaldehyde white system, specifically a composite bonding system of resorcinol donor, methylene donor and white carbon black. Resorcinol donors are mainly resorcinol, resorcinol pre-dispersion, resorcinol-formaldehyde resin, modified resorcinol-formaldehyde resin, and the like; as the methylene donor, hexamethylenetetramine, hexamethoxymethyl melamine, tetrachlorohydroquinone and the like are mainly used.
However, since the polyester fiber has smooth surface, poor hydrophilicity, lack of active groups, high ester bond content, one hydroxyl group and one carboxyl group at each end, inactive chemical activity, and difficult condensation reaction with a meta-alpha-formaldehyde bonding system, which is one of the important reasons for poor bonding strength between the polyester cord and the rubber, and the other important reasons for poor bonding strength between the polyester cord and the rubber are that amine compounds in the rubber cause aging of the polyester layer, the amine compounds are from vulcanization accelerators and antioxidants of rubber compounding agents, ester bonds of polymer molecules of the polyester fiber are easily hydrolyzed by the amine compounds, so that the polymer molecules are broken, the bonding state is broken, the surface of the impregnated polyester cord is wrapped by glue, but the amine compounds can still pass through the glue layer to swim to the surface of the polyester fiber for breaking reaction, so that the bonding strength is greatly reduced.
For these reasons, the application of polyester fiber as a tire framework material is limited, especially the framework material of high-speed heavy-duty tires and engineering tires with large load capacity is easy to generate heat, and the high heat accelerates the chemical reaction of amine compounds and polyester fiber molecular ester bonds, so that the framework material structure is damaged, the adhesive strength of the tire is reduced, the delamination shoulder space phenomenon occurs, and the service life of the tire is greatly shortened.
Disclosure of Invention
The invention aims to provide a synthesis method of resorcinol-itaconic acid-formaldehyde copolymer resin, which aims to solve the problems in the background art.
In order to achieve the above purpose, the present invention provides the following technical solutions: a method for synthesizing resorcinol-itaconic acid-formaldehyde copolymer resin comprises the following steps:
1) Firstly, itaconic acid is dissolved in formaldehyde aqueous solution to obtain mixed solution for standby;
2) Adding water and resorcinol into a four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to enable resorcinol to be completely dissolved, heating and keeping the temperature at 80-95 ℃, dropping the mixed solution obtained in the step 1 by using the dropping funnel for 0.5-1.5 h, reacting for 2-8 h at 90-98 ℃ after the dropping is completed, adjusting the PH to 6.5-7.0 by using NaOH solution, decompressing and distilling to remove water in a reaction system, obtaining reddish brown transparent viscous liquid, removing the reactor when the reddish brown transparent resorcinol-itaconic acid-formaldehyde copolymer resin is obtained after cooling.
Further, the mol ratio of the resorcinol to the itaconic acid to the formaldehyde is 1:0.05-0.4:0.5-1.6.
Compared with the prior art, the invention has the beneficial effects that: the resorcinol-itaconic acid-formaldehyde copolymer resin of the invention has phenolic hydroxyl and carboxyl groups and has strong reactivity. When the fiber-reinforced polyester fiber composite material is applied to tires and other rubber products which take polyester fiber cords as framework materials, amine compounds can be effectively and accurately captured, the corrosion of the amine compounds on the polyester fiber materials is prevented, excellent chemical properties can be endowed, and the adhesive property of rubber and the framework materials is greatly improved. The research shows that the resorcinol-itaconic acid-formaldehyde copolymer resin can be applied to the production process of tires and rubber products, in particular to the adhesive effect between the framework materials of polyester fiber and polyamide fiber materials and rubber is obvious, and the adhesive effect is obviously higher than that of the existing adhesive system.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
A method for synthesizing resorcinol-itaconic acid-formaldehyde copolymer resin comprises the following steps:
1) Firstly, itaconic acid is dissolved in formaldehyde aqueous solution to obtain mixed solution for standby;
2) Adding water and resorcinol into a four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to enable resorcinol to be completely dissolved, heating and keeping the temperature at 80-95 ℃, dropping the mixed solution obtained in the step 1 by using the dropping funnel for 0.5-1.5 h, reacting for 2-8 h at 90-98 ℃, adjusting the PH to 6.5-7.0 by using NaOH solution, decompressing and distilling to remove water in a reaction system, obtaining reddish brown transparent viscous liquid, removing the reactor when the reddish brown transparent resorcinol-itaconic acid-formaldehyde copolymer resin is obtained after cooling.
Further, the mol ratio of the resorcinol to the itaconic acid to the formaldehyde is 1:0.05-0.4:0.5-1.6.
Example 1
First, 5.2g of itaconic acid was dissolved in 16.3g of 37% aqueous formaldehyde solution to obtain a mixed solution for use. Adding 20ml of water and 44g of resorcinol into a 250ml four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to dissolve resorcinol completely, heating and keeping the temperature to 80-95 ℃, dropwise adding a mixed solution of itaconic acid and formaldehyde with the dropping funnel for 0.5-1.5 h, reacting for 5.5h at 90-98 ℃, adjusting the PH to 6.5-7.0 with NaOH solution, distilling under reduced pressure to remove water in the reaction system to obtain reddish brown transparent viscous liquid, removing the reactor when the reactor is still hot, and cooling to obtain reddish brown transparent solid. The softening point of the detected product was 96.5℃and the free resorcinol content was 1.12%.
Example 2
First, 5.2g of itaconic acid was dissolved in 26.0g of 37% aqueous formaldehyde solution to obtain a mixed solution for use. Adding 20ml of water and 44g of resorcinol into a 250ml four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to dissolve resorcinol completely, heating and keeping the temperature to 80-95 ℃, dropwise adding a mixed solution of itaconic acid and formaldehyde with the dropping funnel for 0.5-1.5 h, reacting for 6.5h at 90-98 ℃, adjusting the PH to 6.5-7.0 with NaOH solution, distilling under reduced pressure to remove water in the reaction system to obtain reddish brown transparent viscous liquid, removing the reactor when the reactor is still hot, and cooling to obtain reddish brown transparent solid. The softening point of the detected product was 99.3℃and the free resorcinol content was 0.46%.
Example 3
First, 10.5g of itaconic acid was dissolved in 16.3g of 37% aqueous formaldehyde solution to obtain a mixed solution for use. Adding 20ml of water and 44g of resorcinol into a 250ml four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to dissolve resorcinol completely, heating and keeping the temperature to 80-95 ℃, dropwise adding a mixed solution of itaconic acid and formaldehyde with the dropping funnel for 0.5-1.5 h, reacting for 5.5h at 90-98 ℃, adjusting the PH to 6.5-7.0 with NaOH solution, distilling under reduced pressure to remove water in the reaction system to obtain reddish brown transparent viscous liquid, removing the reactor when the reactor is still hot, and cooling to obtain reddish brown transparent solid. The softening point of the product was 88.4℃and the free resorcinol content was 0.82%.
Example 4
First, 10.5g of itaconic acid was dissolved in 26.0g of 37% aqueous formaldehyde solution to obtain a mixed solution for use. Adding 20ml of water and 44g of resorcinol into a 250ml four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to dissolve resorcinol completely, heating and keeping the temperature to 80-95 ℃, dropwise adding a mixed solution of itaconic acid and formaldehyde with the dropping funnel for 0.5-1.5 h, reacting for 6.5h at 90-98 ℃, adjusting the PH to 6.5-7.0 with NaOH solution, distilling under reduced pressure to remove water in the reaction system to obtain reddish brown transparent viscous liquid, removing the reactor when the reactor is still hot, and cooling to obtain reddish brown transparent solid. The softening point of the detected product was 95.7℃and the free resorcinol content was 0.40%.
Example 5
15.6g of itaconic acid was first dissolved in 29.2g of 37% aqueous formaldehyde solution to obtain a mixed solution for use. Adding 20ml of water and 44g of resorcinol into a 250ml four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to dissolve resorcinol completely, heating and keeping the temperature to 80-95 ℃, dropwise adding a mixed solution of itaconic acid and formaldehyde with the dropping funnel for 0.5-1.5 h, reacting for 5.0h at 90-98 ℃, adjusting the PH to 6.5-7.0 with NaOH solution, distilling under reduced pressure to remove water in the reaction system to obtain reddish brown transparent viscous liquid, removing the reactor when the reactor is still hot, and cooling to obtain reddish brown transparent solid. The softening point of the detected product was 80.5℃and the free resorcinol content was 0.42%.
Example 6
15.6g of itaconic acid was first dissolved in 39.0g of 37% aqueous formaldehyde solution to obtain a mixed solution for use. Adding 20ml of water and 44g of resorcinol into a 250ml four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to dissolve resorcinol completely, heating and keeping the temperature to 80-95 ℃, dropwise adding a mixed solution of itaconic acid and formaldehyde with the dropping funnel for 0.5-1.5 h, reacting for 6.0h at 90-98 ℃, adjusting the PH to 6.5-7.0 with NaOH solution, distilling under reduced pressure to remove water in the reaction system to obtain reddish brown transparent viscous liquid, removing the reactor while the reactor is still hot, and cooling to obtain reddish brown transparent solid. The softening point of the product was measured to be 87.2℃and the free resorcinol content was 0.25%.
The resorcinol-itaconic acid-formaldehyde copolymer resin structure has phenolic hydroxyl and carboxyl groups, has strong reactivity, can effectively and accurately capture amine compounds when being applied to tires and other rubber products taking polyester fiber cords as framework materials, and can prevent the amine compounds from corroding polyester fiber materials due to the fact that the amine compounds are derived from rubber compounding agent vulcanization accelerators and anti-aging agents, and can endow excellent chemical properties. The research shows that the resorcinol-itaconic acid-formaldehyde copolymer resin is applied to the production process of tires and rubber products, in particular to the adhesive effect between the framework materials of polyester fiber and polyamide fiber materials and rubber, which is obviously higher than that of the existing adhesive system.
The resorcinol-itaconic acid-formaldehyde copolymer resin of the example was used in the adhesion of rubber to polyester fiber cords and compared to similar substances commonly used today, the comparison being resorcinol pre-dispersion and resorcinol-formaldehyde resin, and the sizing test formulations were designed as described in Table 1, and the three sizes were mixed in the same process. The test compounds were tested for their vulcanization characteristics, physical properties of the vulcanizates and H extraction force of the vulcanizates, respectively, and the data of the tests are listed in the following tables, respectively. Experiments prove that the equal amount of resorcinol-itaconic acid-formaldehyde copolymer resin is used for replacing three sizing materials of resorcinol pre-dispersion and resorcinol-formaldehyde resin, the Mooney scorch time and t90 of the sizing materials are slightly prolonged, the physical properties and dynamic mechanical properties of vulcanized rubber are equivalent, and the adhesive property and the adhesive aging resistance are obviously improved.
Table 1 test recipe
TABLE 2 vulcanization Properties of compounds
TABLE 3 physical Properties of the vulcanizate
TABLE 4 test of H extraction force N of vulcanizates
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (2)
1. The synthesis method of the resorcinol-itaconic acid-formaldehyde copolymer resin is characterized by comprising the following steps:
1) Firstly, itaconic acid is dissolved in formaldehyde aqueous solution to obtain mixed solution for standby;
2) Adding water and resorcinol into a four-neck flask with a stirrer, a dropping funnel, a reflux device and a thermometer, starting stirring, heating and keeping the temperature at 78-82 ℃ to enable resorcinol to be completely dissolved, heating and keeping the temperature at 80-95 ℃, dropping the mixed solution obtained in the step 1 by using the dropping funnel for 0.5-1.5 h, reacting for 2-8 h at 90-98 ℃ after the dropping is completed, adjusting the PH to 6.5-7.0 by using NaOH solution, decompressing and distilling to remove water in a reaction system, obtaining reddish brown transparent viscous liquid, removing the reactor when the reddish brown transparent resorcinol-itaconic acid-formaldehyde copolymer resin is obtained after cooling.
2. The method for synthesizing resorcinol-itaconic acid-formaldehyde copolymer resin according to claim 1, wherein the molar ratio of resorcinol, itaconic acid and formaldehyde is 1:0.05-0.4:0.5-1.6.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004402A1 (en) * | 1978-03-18 | 1979-10-03 | Hoechst Aktiengesellschaft | Use of modified novolaks as a reinforcing resin for polymers, rubber or rubber based adhesives |
| CN1093724A (en) * | 1993-02-03 | 1994-10-19 | 住友化学工业株式会社 | Reinforcing rubber articles, its production method and suitable rubber combination |
| WO2000000691A1 (en) * | 1998-06-30 | 2000-01-06 | Peach State Labs, Inc. | Stain resistant polymers and compositions |
| CN101230122A (en) * | 2008-02-27 | 2008-07-30 | 深圳市容大电子材料有限公司 | Anhydride modified alkyd resin and photoresist composition obtained thereby |
| JP2016069526A (en) * | 2014-09-30 | 2016-05-09 | 東レ株式会社 | Adhesive for fiber and rubber, and producing method of adhesive for fiber and rubber |
| CN105793368A (en) * | 2013-10-25 | 2016-07-20 | Ppg工业俄亥俄公司 | Aqueous-based coating composition containing hydroxy-terminated polybutadiene |
-
2023
- 2023-02-06 CN CN202310065459.9A patent/CN116444747B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004402A1 (en) * | 1978-03-18 | 1979-10-03 | Hoechst Aktiengesellschaft | Use of modified novolaks as a reinforcing resin for polymers, rubber or rubber based adhesives |
| CN1093724A (en) * | 1993-02-03 | 1994-10-19 | 住友化学工业株式会社 | Reinforcing rubber articles, its production method and suitable rubber combination |
| WO2000000691A1 (en) * | 1998-06-30 | 2000-01-06 | Peach State Labs, Inc. | Stain resistant polymers and compositions |
| CN101230122A (en) * | 2008-02-27 | 2008-07-30 | 深圳市容大电子材料有限公司 | Anhydride modified alkyd resin and photoresist composition obtained thereby |
| CN105793368A (en) * | 2013-10-25 | 2016-07-20 | Ppg工业俄亥俄公司 | Aqueous-based coating composition containing hydroxy-terminated polybutadiene |
| JP2016069526A (en) * | 2014-09-30 | 2016-05-09 | 東レ株式会社 | Adhesive for fiber and rubber, and producing method of adhesive for fiber and rubber |
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