CN106565950A - Synthesis method of nonylphenol polyoxyethylene ether carboxylic ester surfactant - Google Patents
Synthesis method of nonylphenol polyoxyethylene ether carboxylic ester surfactant Download PDFInfo
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- CN106565950A CN106565950A CN201610987435.9A CN201610987435A CN106565950A CN 106565950 A CN106565950 A CN 106565950A CN 201610987435 A CN201610987435 A CN 201610987435A CN 106565950 A CN106565950 A CN 106565950A
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- CN
- China
- Prior art keywords
- parts
- polyoxyethylene ether
- synthetic method
- acid
- nonylphenol polyoxyethylene
- Prior art date
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Classifications
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis method of a nonylphenol polyoxyethylene ether carboxylic ester surfactant. The method comprises the steps that 35-50 parts of nonylphenol polyoxyethylene ether, 2-5 parts of carboxylic acid, 0.005-0.015 part of polymerization inhibitor, 0.5-1.5 parts of catalyst and 50-60 parts of solvent are added into a flask provided with a stirrer, a temperature gauge and a condensation pipe, the flask is filled with nitrogen to be protected, stirring starts to be carried out, the temperature is stably increased to 110-116 DEG C, a heat-insulated reaction is carried out for 8 h at the temperature, and then the acid value starts to be tested till the acid value of the reactant is smaller than or equal to 6 mgKOH/g; and cooling, washing and distillation start to be carried out, and the final product is obtained. The nonylphenol polyoxyethylene ether carboxylic ester prepared through the synthesis method is good in biodegradability, and the harm to the environment and human body health is greatly reduced; and meanwhile, when the synthesized nonylphenol polyoxyethylene ether carboxylic ester is applied to an adhesive, foamability is obviously reduced under the condition that other properties are not changed.
Description
Technical field
The present invention relates to a kind of synthetic method of NPE carboxylate, belongs to synthesis chemical field.
Background technology
It is well known that NPE has good infiltration, emulsifying, dispersion, antiacid, alkali resistant, hard water resistance, anti-
Reduction, antioxidative ability, as surfactant and cleaning agent the fields such as textile industry are widely used in, but its foaming characteristic compared with
Height, and nonyl phenol can be rapidly decomposed into after being discharged in environment, nonyl phenol is larger to the hazard ratio of environment.In order to reduce foaming
Property, the discharge capacity of nonyl phenol is reduced, the pollution to environment is reduced, by carrying out NPE and carboxylic acid to be esterified instead
Should, the product for obtaining not only has those functions of NPE itself, and acid number is low, will not corrode workpiece；
Foaming characteristic is low, and technological operation performance is good；Biodegradability is good, and the hazardness to environment and health is substantially reduced.
The content of the invention
The present invention provides a kind of synthetic method of NPE carboxylate, polyoxyethylene nonyl phenyl prepared by the present invention
Ethylene ether carboxylate biodegradability is good, and the hazardness to environment and health is substantially reduced, meanwhile, the present invention is synthesized
NPE carboxylate when being applied in binding agent in the case where keeping other performances constant, foaming characteristic has
Substantially reduce.
Technical proposal that the invention solves the above-mentioned problems is as follows：A kind of synthesis side of NPE carboxylate
Method includes:In being furnished with the flask of agitator, thermometer, condensing tube, 35～50 parts of NPEs of addition, 2～5 parts
Carboxylic acid, 0.005～0.015 part of polymerization inhibitor, 0.5～1.5 part of catalyst, 50～60 parts of solvents, nitrogen charging gas shielded in bottle starts to stir
110 DEG C～116 DEG C are mixed and are warming up to steadily, at this temperature insulation reaction starts to survey acid number after 8 hours, to the acid number of reactant
≤6mgKOH/g；Then, start to lower the temperature, wash, distill, obtain final products.
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, the NPE model（U.S. DOW chemistry NP-12, Jiangsu Jia Feng chemistry share
The TX-12 of the producer such as company limited or Jiangsu Hai'an petrochemical plant）.
Further, the carboxylic acid is one or two mixture in fumaric acid, maleic anhydride.
Further, the polymerization inhibitor is hydroquinone, MEHQ, 2,6- toluene di-tert-butyl phenols, 2,5- bis-
One or more of mixture in methyl hydroquinone, 1,4-benzoquinone, it is preferable that the polymerization inhibitor is MEHQ.
Further, the catalyst is one or two mixture in p-methyl benzenesulfonic acid, sulfonic acid.
Further, the solvent is one or two mixture in toluene, dimethylbenzene, it is preferable that the solvent is first
Benzene.
Specific embodiment
The principle and feature of the present invention are described below, example is served only for explaining the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1
In being furnished with the flask of agitator, thermometer, condensing tube, 35 parts of NPE NP-12,2 parts of rich horses are added
Acid, 0.005 part of MEHQ, 0.5 part of p-methyl benzenesulfonic acid, 50 parts of toluene, nitrogen charging gas shielded in bottle starts stirring simultaneously steadily
114 DEG C are warming up to, at this temperature insulation reaction starts to survey acid number after 8 hours, to the acid number≤6mgKOH/g of reactant；So
Afterwards, start to lower the temperature, wash, distill, obtain final products.
Embodiment 2
In being furnished with the flask of agitator, thermometer, condensing tube, 50 parts of NPE TX-12,5 parts of rich horses are added
Acid, 0.015 part of MEHQ, 1.5 parts of p-methyl benzenesulfonic acid, 60 parts of toluene, nitrogen charging gas shielded in bottle starts stirring simultaneously
114 DEG C are warming up to steadily, and at this temperature insulation reaction starts to survey acid number after 8 hours, to the acid number≤6mgKOH/g of reactant；
Then, start to lower the temperature, wash, distill, obtain final products.
Embodiment 3
In being furnished with the flask of agitator, thermometer, condensing tube, 42 parts of NPE NP-12 are added, 3.5 parts suitable
Anhydride maleique, 0.01 part of MEHQ, 1 part of sulfonic acid, 55 parts of toluene, nitrogen charging gas shielded in bottle starts stirring simultaneously steadily
114 DEG C are warming up to, at this temperature insulation reaction starts to survey acid number after 8 hours, to the acid number≤6mgKOH/g of reactant；So
Afterwards, start to lower the temperature, wash, distill, obtain final products.
Embodiment 4
In being furnished with the flask of agitator, thermometer, condensing tube, 42 parts of NPE TX-12,2 parts of rich horses are added
Acid, 1 part of maleic anhydride, 0.01 part of MEHQ, 1 part of p-methyl benzenesulfonic acid, 55 parts of toluene, nitrogen charging gas shielded in bottle,
Start to stir and be warming up to 114 DEG C steadily, at this temperature insulation reaction starts to survey acid number after 8 hours, to the acid number of reactant
≤6mgKOH/g；Then, start to lower the temperature, wash, distill, obtain final products.
By the performance of the NPE carboxylate of the following experimental test present invention.
Test example 1
HLB value：Tested using gas chromatography.
Test example 2
Acid number：Tested according to GB/T2895-2008.
Test example 3
Foaming characteristic：Test condition：150g samples, the compressed air of 0.5MPa continues bubbling 1min.
Test example 4
Decomposition rate：Tested using liquid chromatography.
NPE and embodiment 1,2,3,4 are carried out into performance contrast test, test result is as follows：
From the experimental result of upper table can be seen that the present invention preparation NPE carboxylate have acid number it is low,
The low, advantage that nonyl phenol decomposition rate is slow of bubble property, it is little to be applied in industry adhesive the corrosivity to workpiece, the low increase of foaming characteristic
The operability of binding agent, while its biodegradation rate is slower, is conducive to environmental conservation.
The foregoing is only presently preferred embodiments of the present invention, not to limit the present invention, all spirit in the present invention and
Within principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.
Claims (6)
1. a kind of synthetic method of NPE carboxylate surfactants, it is characterised in that include:Stir being furnished with
In mixing the flask of device, thermometer, condensing tube, 35～50 parts of NPEs of addition, 2～5 parts of carboxylic acids, 0.005～
0.015 part of polymerization inhibitor, 0.5～1.5 part of catalyst, 50～60 parts of solvents, nitrogen charging gas shielded in bottle starts to stir and heat up steadily
To 110 DEG C～116 DEG C, at this temperature insulation reaction starts to survey acid number after 8 hours, to the acid number≤6mgKOH/g of reactant；
Then, start to lower the temperature, wash, distill, obtain final products.
2. synthetic method according to claim 1, it is characterised in that NPE model NP-12
Or TX-12.
3. synthetic method according to claim 1, it is characterised in that the carboxylic acid is in fumaric acid, maleic anhydride
One or two mixture.
4. synthetic method according to claim 1, it is characterised in that the polymerization inhibitor is hydroquinone, para hydroxybenzene first
One or more of mixture in ether, 2,6- toluene di-tert-butyl phenols, 2,5- dimethyl hydroquinone, 1,4-benzoquinone.
5. synthetic method according to claim 1, it is characterised in that the catalyst is in p-methyl benzenesulfonic acid, sulfonic acid
Kind or two kinds of mixture.
6. synthetic method according to claim 1, it is characterised in that the solvent is a kind of in toluene, dimethylbenzene or two
The mixture planted.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610987435.9A CN106565950A (en) | 2016-11-10 | 2016-11-10 | Synthesis method of nonylphenol polyoxyethylene ether carboxylic ester surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610987435.9A CN106565950A (en) | 2016-11-10 | 2016-11-10 | Synthesis method of nonylphenol polyoxyethylene ether carboxylic ester surfactant |
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| CN106565950A true CN106565950A (en) | 2017-04-19 |
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| CN201610987435.9A Pending CN106565950A (en) | 2016-11-10 | 2016-11-10 | Synthesis method of nonylphenol polyoxyethylene ether carboxylic ester surfactant |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114316249A (en) * | 2020-09-30 | 2022-04-12 | 上海飞凯材料科技股份有限公司 | Alkylphenol polyoxyethylene (methyl) acrylate, processing method thereof and coating |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1511859A (en) * | 2002-12-31 | 2004-07-14 | �й�ʯ�ͻ����ɷ�����˾��³�ֹ�˾ | Lissapol N(methyl) propenoic acid ester and its preparation and use |
| CN104193622A (en) * | 2013-09-29 | 2014-12-10 | 安庆飞凯高分子材料有限公司 | Preparing method of nonylphenol polyoxyethylene ether acrylate |
-
2016
- 2016-11-10 CN CN201610987435.9A patent/CN106565950A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1511859A (en) * | 2002-12-31 | 2004-07-14 | �й�ʯ�ͻ����ɷ�����˾��³�ֹ�˾ | Lissapol N(methyl) propenoic acid ester and its preparation and use |
| CN104193622A (en) * | 2013-09-29 | 2014-12-10 | 安庆飞凯高分子材料有限公司 | Preparing method of nonylphenol polyoxyethylene ether acrylate |
Non-Patent Citations (1)
| Title |
|---|
| 谢剑妹: ""新型表面活性剂的合成及其乳化性能的研究"", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114316249A (en) * | 2020-09-30 | 2022-04-12 | 上海飞凯材料科技股份有限公司 | Alkylphenol polyoxyethylene (methyl) acrylate, processing method thereof and coating |
| CN114316249B (en) * | 2020-09-30 | 2023-08-22 | 上海飞凯材料科技股份有限公司 | Alkylphenol polyoxyethylene (methyl) acrylate, treatment method thereof and coating |
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Application publication date: 20170419 |