CN116874741A - Terpolymer and preparation method and application thereof - Google Patents
Terpolymer and preparation method and application thereof Download PDFInfo
- Publication number
- CN116874741A CN116874741A CN202310756112.9A CN202310756112A CN116874741A CN 116874741 A CN116874741 A CN 116874741A CN 202310756112 A CN202310756112 A CN 202310756112A CN 116874741 A CN116874741 A CN 116874741A
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- CN
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- Prior art keywords
- terpolymer
- epoxy resin
- linoleic acid
- acrylic acid
- raw materials
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229920001897 terpolymer Polymers 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000003822 epoxy resin Substances 0.000 claims abstract description 24
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 24
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims abstract description 15
- 235000020778 linoleic acid Nutrition 0.000 claims abstract description 15
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims abstract description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 239000000839 emulsion Substances 0.000 claims description 16
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 4
- QDLGKFNCVHBEOQ-UHFFFAOYSA-N 2-chloro-4-(6-methoxy-3,4-dihydro-2H-quinolin-1-yl)pyrido[3,2-d]pyrimidine Chemical compound COc1ccc2N(CCCc2c1)c1nc(Cl)nc2cccnc12 QDLGKFNCVHBEOQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical group CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 238000007142 ring opening reaction Methods 0.000 abstract description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 abstract description 2
- 239000004925 Acrylic resin Substances 0.000 abstract description 2
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1466—Acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
- C08F283/105—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule on to unsaturated polymers containing more than one epoxy radical per molecule
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1472—Fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a terpolymer, which comprises the following raw materials in percentage by mass: epoxy resin E4455.3%, linoleic acid 34%, acrylic acid 9.2%, polymerization inhibitor 0.5% and catalyst 1%. According to the invention, linoleic acid, acrylic acid and epoxy resin E44 are subjected to ring-opening reaction to synthesize a novel terpolymer, and long-chain linoleic acid molecules and acrylic acid molecules are connected into the molecules of the epoxy resin to obtain a macromolecular structure with a main chain having a rigid structure of the epoxy resin, a long carbon chain with linoleic acid flexibility and a side group suspending carboxyl hydrophilic functional group; so that the terpolymer has excellent toughness and impact resistance on the basis of the bonding strength, corrosion resistance and mechanical property of the epoxy resin. The invention has low price of the raw materials, short reaction completion time and no use of organic solvent, thereby greatly saving the production cost and reducing the pollution of the production to the environment.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a terpolymer and a preparation method and application thereof.
Background
In recent years, with the rapid development of the coating industry, styrene-acrylic emulsion has become one of the hot spots for research in the coating industry with its excellent performance, but the performance of the current styrene-acrylic emulsion still has a large improvement space. The focus of research is on modifying styrene-acrylic emulsion by chemical and physical methods, but modifying with silicone, organofluorine, epoxy resins is more common. However, the existing modified styrene-acrylic emulsion still has the defects in performance, such as long surface drying time, poor mechanical properties and the like.
Disclosure of Invention
The invention aims to solve the problems of long surface drying time and poor mechanical property of styrene-acrylic emulsion in the prior art, and provides a terpolymer and a preparation method and application thereof.
In order to solve the technical problems, the invention adopts the following technical scheme: the terpolymer comprises the following raw materials in percentage by mass: epoxy resin E4455.3%, linoleic acid 34%, acrylic acid 9.2%, polymerization inhibitor 0.5% and catalyst 1%.
Preferably, the polymerization inhibitor is para-hydroxyanisole.
Preferably, the catalyst is N, N-dimethylbenzylamine.
Preferably, the preparation method of the terpolymer comprises the following steps: weighing the raw materials according to the proportion; and heating the epoxy resin E44 to reduce the viscosity, adding the epoxy resin E44, acrylic acid, linoleic acid and a polymerization inhibitor into a four-neck flask provided with a thermometer, a stirring device and a condensation reflux device, slowly heating while stirring under the protection of nitrogen, adding a catalyst when the temperature is stabilized at a set temperature, and reacting to obtain the terpolymer after the reaction is finished.
Preferably, the set temperature is 90 ℃.
The invention also provides application of the terpolymer in preparation of styrene-acrylic emulsion.
The invention has the beneficial effects that:
according to the invention, linoleic acid, acrylic acid and epoxy resin E44 are subjected to ring opening reaction to synthesize a novel terpolymer, and long-chain linoleic acid molecules and acrylic acid molecules are connected into the molecules of the epoxy resin to obtain a macromolecular structure with a main chain having a rigid structure of the epoxy resin, a long carbon chain with linoleic acid flexibility and a side group suspending carboxyl hydrophilic functional group; so that the terpolymer has excellent toughness and impact resistance on the basis of the bonding strength, corrosion resistance and mechanical property of the epoxy resin.
And secondly, the linoleic acid and the acrylic acid used in the invention are low-cost raw materials, and the epoxy group has high activity and very rapid ring-opening reaction with carboxyl, so that the reaction completion time is short, the production cost is greatly saved, and the production efficiency is improved.
And thirdly, in the whole preparation process of the terpolymer, no organic solvent is used, so that the pollution of production to the environment is reduced.
Fourthly, the terpolymer (AEL) is used as a polymerization unit body to modify the styrene-acrylic emulsion to prepare the room temperature self-crosslinking epoxy linoleic acid grafted styrene-acrylic emulsion, and as the long carbon chain structural unit of the linoleic acid is introduced into the terpolymer (AEL), the emulsion can be subjected to a curing reaction with oxygen in the air at room temperature, so that the room temperature self-crosslinking is realized, and the surface drying and curing time of the emulsion are obviously shortened; meanwhile, a rigid E44 structural unit is introduced, so that the mechanical strength of the coating film can be greatly improved.
Drawings
FIG. 1 is a graph showing the IR spectrum of a terpolymer prepared in example 1 of the present invention and an epoxy resin.
Detailed Description
The invention will be further described with reference to the drawings and the specific examples.
Example 1
The viscosity of the epoxy resin E44 is reduced by heating, 70g of the epoxy resin E44, 11.64g of acrylic acid, 43g of linoleic acid and 0.63g of polymerization inhibitor are added into a four-neck flask provided with a thermometer, a stirring device and a condensing reflux device, the temperature is slowly increased to 90 ℃ under the protection of nitrogen under stirring, after the temperature is stable, 1.25g of catalyst is added for reaction, and the terpolymer product is obtained after the reaction is finished.
The infrared spectra of the terpolymer and the epoxy resin prepared in the example are shown in figure 1.
Example 2
The viscosity of the epoxy resin E44 is reduced by heating, 140g of the epoxy resin E44, 23.28g of acrylic acid, 86g of linoleic acid and 1.26g of polymerization inhibitor are added into a four-neck flask provided with a thermometer, a stirring device and a condensing reflux device, the temperature is slowly increased to 90 ℃ under the protection of nitrogen under stirring, after the temperature is stable, 2.5g of catalyst is added for reaction, and a terpolymer product is obtained after the reaction is finished.
Example 3
The viscosity of the epoxy resin E44 is reduced by heating, 105g of the epoxy resin E44, 17.46g of acrylic acid, 64.5g of linoleic acid and 0.95 of polymerization inhibitor are added into a four-neck flask provided with a thermometer, a stirring device and a condensing reflux device, the temperature is slowly increased to 90 ℃ under the protection of nitrogen under stirring, after the temperature is stable, 1.88g of catalyst is added for reaction, and the terpolymer product is obtained after the reaction is finished.
Example 4 use of terpolymer in modification of styrene-acrylic emulsion
The raw materials are as follows in mass percent in table 1: styrene, butyl acrylate, methyl methacrylate and the terpolymer (AEL) prepared in example 1 are placed in a beaker, fully stirred and dissolved for standby, and then initiator ammonium persulfate is dissolved in deionized water to prepare an initiator solution for standby. 60wt% of water and 20wt% of mixture raw materials are added into a four-neck flask provided with a condenser, a stirrer and a thermometer, and meanwhile, an emulsifier and a buffer are added, and the mixture is stirred at a high speed for 20min to perform pre-emulsification. Then the rotation speed is reduced, the temperature is increased to 80 ℃, 10wt% of initiator solution is added, after the reaction is carried out for 30min, the rest mixture raw materials are dripped, and the dripping time is 4h (1/10 of initiator solution is supplemented every 30 min). After the mixture raw materials are added dropwise, the temperature is raised to 85 ℃, the rest initiator solution is added, and the reaction is carried out for 30min under the heat preservation. Then cooling to 30 ℃, adding ammonia water to adjust the pH value to be neutral, adding a drier and an anti-flash rust agent, and stirring at a high speed for 10min to obtain the room temperature self-crosslinking epoxy linolenic acid grafted styrene-acrylic emulsion containing AEL, wherein the performance indexes are shown in Table 2.
TABLE 1 raw material ratios of styrene-acrylic emulsion prepared in this example
TABLE 2 Performance index of the styrene-acrylic emulsion prepared in this example
As shown in Table 2, the self-crosslinking at room temperature can be realized by utilizing the terpolymer to prepare the styrene-acrylic emulsion, and compared with other similar products in the prior art, the surface drying and curing time at room temperature are obviously shortened; and the mechanical performance indexes such as hardness, adhesive force and tensile strength are also obviously improved.
The specification and figures are to be regarded in an illustrative rather than a restrictive sense, and one skilled in the art, in light of the teachings of this invention, may make various substitutions and alterations to some of its features without the need for inventive faculty, all being within the scope of this invention.
Claims (6)
1. The terpolymer is characterized by comprising the following raw materials in percentage by mass: epoxy resin E4455.3%, linoleic acid 34%, acrylic acid 9.2%, polymerization inhibitor 0.5% and catalyst 1%.
2. The terpolymer according to claim 1 wherein the inhibitor is para-hydroxyanisole.
3. The terpolymer according to claim 1 wherein the catalyst is N, N-dimethylbenzylamine.
4. A terpolymer according to claim 1, wherein the terpolymer is prepared by a process comprising: weighing the raw materials according to the proportion; and heating the epoxy resin E44 to reduce the viscosity, adding the epoxy resin E44, acrylic acid, linoleic acid and a polymerization inhibitor into a four-neck flask provided with a thermometer, a stirring device and a condensation reflux device, slowly heating while stirring under the protection of nitrogen, adding a catalyst when the temperature is stabilized at a set temperature, and reacting to obtain the terpolymer after the reaction is finished.
5. A terpolymer according to claim 4, wherein the set temperature is 90 ℃.
6. Use of a terpolymer according to any one of claims 1-5 in the preparation of a styrene-acrylic emulsion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310756112.9A CN116874741A (en) | 2023-06-26 | 2023-06-26 | Terpolymer and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310756112.9A CN116874741A (en) | 2023-06-26 | 2023-06-26 | Terpolymer and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116874741A true CN116874741A (en) | 2023-10-13 |
Family
ID=88253938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310756112.9A Pending CN116874741A (en) | 2023-06-26 | 2023-06-26 | Terpolymer and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116874741A (en) |
-
2023
- 2023-06-26 CN CN202310756112.9A patent/CN116874741A/en active Pending
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