CN111269580A - Environment-friendly high-temperature-resistant composite plasticizer and preparation method and application thereof - Google Patents
Environment-friendly high-temperature-resistant composite plasticizer and preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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Abstract
The invention relates to the technical field of plasticizers, and provides an environment-friendly high-temperature-resistant composite plasticizer which comprises the following components in parts by mass: 80-85 parts of methyl chloro-palm oil, 10-15 parts of epoxy vegetable oil, 0.1-1 part of epoxy resin active diluent, 0.1-3 parts of antioxidant and 0.1-2 parts of coupling agent. The main raw materials of the composite plasticizer provided by the invention are renewable natural oil, and the composite plasticizer does not contain heavy metal and o-benzene substances, is good in environmental protection, good in compatibility with PVC, excellent in flame retardance and high temperature resistance, and low in price. The composite plasticizer provided by the invention has better high temperature resistance than dioctyl phthalate, has lower price than dioctyl phthalate, can replace dioctyl phthalate in PVC industry, effectively solves the problems of product yellowing, roller sticking, paste material and the like in the use process of chlorinated palm oil methyl ester in PVC high-temperature industry, and breaks through the application limit of the PVC high-temperature industry to chlorinated palm oil methyl ester.
Description
Technical Field
The invention relates to the technical field of plasticizers, in particular to an environment-friendly high-temperature-resistant composite plasticizer and a preparation method and application thereof.
Background
The plasticizer is one of indispensable important raw materials for producing polyvinyl chloride (PVC) products, and the plasticizer mainly has the functions of weakening the secondary bond among resin molecules, plasticizing the mobility of resin molecular chains, reducing the crystallinity of the resin molecules, and increasing the plasticity of the resin molecules, so that the PVC products have the properties of flexibility, elasticity, low temperature resistance and the like. At present, phthalate plasticizers (DOP) are generally used as plasticizers, but because they contain aromatic rings, the plasticizer is difficult to biodegrade and has the possibility of carcinogenesis, and the use of the plasticizer in European Union countries is limited.
The chlorinated palm oil methyl ester is used as a novel environment-friendly plasticizer, the raw material of the product is reproducible natural oil, and the product does not contain heavy metal and o-benzene substances. The flame retardant PVC composite material is low in price, good in compatibility with PVC, and excellent in flame retardant and environment-friendly performance. Therefore, methyl chlorinated palm oil is one of the important plasticizers to replace DOP. But the high temperature resistance of the methyl chloro-palm oil is poorer, and the high temperature resistance is far lower than that of DOP. At present, the chlorinated palm oil methyl ester is mainly applied to replace the PVC industry with lower processing temperature, but for the PVC industry (such as films, artificial leather and the like) with higher processing temperature, the problems of product yellowing, roller sticking, paste sticking and the like are easy to occur in the use process, and the popularization and the use of the chlorinated palm oil methyl ester in the PVC high-temperature industry are limited to a great extent. Therefore, an environment-friendly high-temperature-resistant composite plasticizer is urgently needed to be developed to replace DOP, and the application limit of the PVC high-temperature industry to the chlorinated palm oil methyl ester is broken.
Disclosure of Invention
In view of the above, the invention provides an environment-friendly high-temperature-resistant composite plasticizer, and a preparation method and application thereof. The composite plasticizer provided by the invention has the advantages of good environmental protection property, good high temperature resistance and good compatibility with PVC.
In order to achieve the above object, the present invention provides the following technical solutions:
an environment-friendly high-temperature-resistant composite plasticizer comprises the following components in parts by mass: 80-85 parts of methyl chloro-palm oil, 10-15 parts of epoxy vegetable oil, 0.1-1 part of epoxy resin active diluent, 0.1-3 parts of antioxidant and 0.1-2 parts of coupling agent.
Preferably, the epoxy vegetable oil comprises one or more of epoxy rice bran oil, epoxy linseed oil and epoxy rapeseed oil.
Preferably, the epoxy resin reactive diluent comprises one or more of hexanediol diglycidyl ether, 1, 4-butanediol diglycidyl ether and polypropylene glycol diglycidyl ether.
Preferably, the antioxidant comprises pentaerythritol diisodecyl diphosphite and/or trialkyl phosphite.
Preferably, the coupling agent comprises a silane coupling agent.
Preferably, the silane coupling agent includes gamma-glycidoxypropyltrimethoxysilane and/or gamma-mercaptopropyltrimethoxysilane.
The invention provides a preparation method of the environment-friendly high-temperature-resistant composite plasticizer, which comprises the following steps:
heating the methyl chloro-palm oil, adding the epoxy vegetable oil, the epoxy resin active diluent, the antioxidant and the coupling agent, stirring, mixing and cooling to room temperature to obtain the environment-friendly high-temperature-resistant composite plasticizer.
Preferably, the heating temperature is 45-50 ℃.
Preferably, the stirring and mixing time is 0.5-1.0 h.
The invention provides application of the environment-friendly high-temperature-resistant composite plasticizer in a polyvinyl chloride product.
The invention provides an environment-friendly high-temperature-resistant composite plasticizer which comprises the following components in parts by mass: 80-85 parts of methyl chloro-palm oil, 10-15 parts of epoxy vegetable oil, 0.1-1 part of epoxy resin active diluent, 0.1-3 parts of antioxidant and 0.1-2 parts of coupling agent. The main raw materials of the composite plasticizer provided by the invention are renewable natural oil, the product does not contain heavy metal and o-benzene substances, and the composite plasticizer has the advantages of good environmental protection, good compatibility with PVC, excellent flame retardance and high temperature resistance, and low price. The composite plasticizer provided by the invention has better high temperature resistance than dioctyl phthalate, has lower price than dioctyl phthalate, can replace dioctyl phthalate in PVC industry, effectively solves the problems of product yellowing, roller sticking, paste material and the like in the use process of chlorinated palm oil methyl ester in PVC high-temperature industry, and breaks through the application limit of the PVC high-temperature industry to chlorinated palm oil methyl ester.
Detailed Description
The invention provides an environment-friendly high-temperature-resistant composite plasticizer which comprises the following components in parts by mass: 80-85 parts of methyl chloro-palm oil, 10-15 parts of epoxy vegetable oil, 0.1-1 part of epoxy resin active diluent, 0.1-3 parts of antioxidant and 0.1-2 parts of coupling agent.
Unless otherwise specified, each component described in the present invention is commercially available.
The composite plasticizer comprises, by mass, 80-85 parts of methyl chloropalmitolate, preferably 82-83 parts; the chlorine content of the chlorinated palm oil methyl ester is preferably 30 + -5%.
The composite plasticizer provided by the invention comprises 10-15 parts by mass of epoxy vegetable oil, and preferably 12-13 parts by mass of epoxy vegetable oil. In the invention, the epoxy vegetable oil preferably comprises one or more of epoxy rice bran oil, epoxy linseed oil and epoxy rapeseed oil; the epoxy vegetable oil plays a role of a stabilizer, can improve the high-temperature resistance of the composite plasticizer, and is non-toxic, harmless and good in environmental protection.
The composite plasticizer provided by the invention comprises 0.1-1 part by mass of epoxy resin active diluent, preferably 0.5-0.8 part by mass. In the present invention, the epoxy resin reactive diluent preferably includes one or more of hexanediol diglycidyl ether, 1, 4-butanediol diglycidyl ether, and polypropylene glycol diglycidyl ether.
The composite plasticizer provided by the invention comprises 0.1-3 parts by mass of an antioxidant, preferably 0.5-2.5 parts by mass, and further preferably 1-2 parts by mass. In the present invention, the antioxidant preferably includes pentaerythritol diisodecyl diphosphite and/or trialkyl phosphite.
The composite plasticizer provided by the invention comprises 0.1-2 parts by mass of a coupling agent, preferably 0.5-1.5 parts by mass. In the present invention, the coupling agent preferably includes gamma-glycidoxypropyltrimethoxysilane and/or gamma-mercaptopropyltrimethoxysilane.
According to the invention, the epoxy resin diluent, the antioxidant and the coupling agent are added, so that the high temperature resistance of the plasticizer can be improved, the popularization and the application in the PVC high temperature industry are facilitated, and the environment-friendly high temperature resistant composite plasticizer is obtained.
The invention provides a preparation method of the environment-friendly high-temperature-resistant composite plasticizer, which comprises the following steps:
heating the methyl chloro-palm oil, adding the epoxy vegetable oil, the epoxy resin active diluent, the antioxidant and the coupling agent, stirring, mixing and cooling to room temperature to obtain the environment-friendly high-temperature-resistant composite plasticizer.
In the invention, the container for preparing the environment-friendly high-temperature-resistant composite plasticizer is preferably a stainless steel reaction kettle; according to the invention, preferably, the methyl chloro-palm oil is added into a stainless steel reaction kettle, and after the methyl chloro-palm oil is heated to a required temperature, other components are added; the invention has no special requirements on the adding sequence of the epoxy vegetable oil, the epoxy resin active diluent, the antioxidant and the coupling agent, and can be added in any sequence.
In the invention, the heating temperature is preferably 45-50 ℃, and more preferably 46-48 ℃; the stirring and mixing time is preferably 0.5-1.0 h, and more preferably 0.6-0.8 h; the invention has no special requirement on the temperature reduction and can be naturally cooled to room temperature.
The invention also provides the application of the composite plasticizer in polyvinyl chloride products; the present invention has no special requirement on the specific method for the application, and the application is performed according to the method well known to those skilled in the art, in the specific embodiment of the present invention, polyvinyl chloride (PVC), the stabilizer and the compound plasticizer of the present invention are preferably mixed and milled on a mill, and the polyvinyl chloride product can be obtained; the stabilizer is preferably a barium-cadmium-zinc stabilizer; the mass ratio of the polyvinyl chloride to the composite plasticizer to the stabilizer is preferably 100:40: 3.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention.
Example 1
The preparation raw materials of the composite plasticizer comprise the following components: 85 parts by weight of methyl chloro-palm oil; 10 parts of epoxy rice bran oil; 1.0 part by weight of 1, 4-butanediol diglycidyl ether; 2.0 parts by weight of pentaerythritol diisodecyl diphosphite; 2.0 parts by weight of gamma-glycidyl ether oxypropyltrimethoxysilane;
the preparation method of the composite stabilizer comprises the following steps: adding the methyl chloro-palm oil into a stainless steel reaction kettle, heating to 45 ℃, adding other raw materials according to the formula amount, mixing and stirring for 0.5h, and cooling to normal temperature to obtain the composite plasticizer.
And (3) performance testing:
(1) high temperature resistance test
100 parts of PVC, 40 parts of composite plasticizer and 3 parts of barium, cadmium and zinc stabilizer are milled on a mill, and the high temperature resistance is tested, wherein the high temperature resistance is the time when the product begins to yellow and the time when the product begins to black in the milling process; the amount of dioctyl phthalate added in the control test was 40 parts, and the amounts of PVC and stabilizer added were the same as in the above protocol, with dioctyl phthalate as the reference.
TABLE 1 test results of high temperature resistance of composite plasticizer
| Plasticizer | The product begins to yellow (min) | The product begins to turn black (min) |
| Compound plasticizer | 12 | 17 |
| Dioctyl phthalate | 10 | 15 |
As can be seen from the data in Table 1, the compound plasticizer of the present invention has better high temperature resistance when both the yellowing and blackening times of the product are longer than when dioctyl phthalate is used as the plasticizer in the open mill process.
(2) Flame retardancy test
100 parts of PVC, 40 parts of composite plasticizer and 3 parts of barium, cadmium and zinc stabilizer are milled on a mill for 6min, the flame retardant property of the obtained product is tested according to GB/T18380-2008, and the result shows that the flame retardant property of the product is B1 grade.
Example 2
The preparation raw materials of the composite plasticizer comprise the following components: 83 parts by weight of methyl chloro-palm oil; 12 parts of epoxy rice bran oil; 0.5 part by weight of 1, 4-butanediol diglycidyl ether; 2.5 parts by weight of pentaerythritol diisodecyl diphosphite; 2.0 parts by weight of gamma-glycidyl ether oxypropyltrimethoxysilane;
the preparation method of the composite stabilizer comprises the following steps: adding the methyl chloro-palm oil into a stainless steel reaction kettle, heating to 50 ℃, adding other raw materials according to the formula components, mixing and stirring for 1.0h, and cooling to normal temperature to obtain the composite plasticizer.
And (3) performance testing:
(1) and (3) high temperature resistance test:
the high temperature resistance of the compounded plasticizer was measured according to the method of example 1, and the results are shown in Table 2.
Table 2 test results of high temperature resistance of composite plasticizer
| Plasticizer | The product begins to yellow (min) | The product begins to turn black (min) |
| Compound plasticizer | 12.5 | 18 |
| Dioctyl phthalate | 10 | 15 |
As can be seen from the data in Table 2, the composite plasticizer of the present invention has better high temperature resistance than dioctyl phthalate.
(2) Flame retardancy test
The flame retardancy test was carried out according to the method of example 1, and the flame retardancy grade of the obtained PVC product was B1.
Example 3
The preparation raw materials of the composite plasticizer comprise the following components: 80 parts by weight of methyl chloro-palm oil; 15 parts of epoxy rice bran oil; 0.5 part by weight of polypropylene glycol diglycidyl ether; 3.0 parts by weight of pentaerythritol diisodecyl diphosphite; 1.5 parts by weight of gamma-glycidyl ether oxypropyl trimethoxysilane;
the preparation method of the composite stabilizer comprises the following steps: adding the methyl chloro-palm oil into a stainless steel reaction kettle, heating to 50 ℃, adding other raw materials according to the formula components, mixing and stirring for 0.5h, and cooling to normal temperature to obtain the composite plasticizer.
And (3) performance testing:
(1) and (3) high temperature resistance test:
the high temperature resistance of the compounded plasticizer was measured according to the method of example 1, and the results are shown in Table 3.
TABLE 3 test results of high temperature resistance of composite plasticizer
| Plasticizer | The product begins to yellow (min) | The product begins to turn black (min) |
| Compound plasticizer | 15 | 19 |
| Dioctyl phthalate | 10 | 15 |
As can be seen from the data in Table 3, the composite plasticizer of the present invention has better high temperature resistance than dioctyl phthalate.
(2) Flame retardancy test
The flame retardancy test was carried out according to the method of example 1, and the flame retardancy grade of the obtained PVC product was B1.
Example 4
The preparation raw materials of the composite plasticizer comprise the following components: 82 parts by weight of methyl chloro-palm oil; 13 parts of epoxy rice bran oil; 0.8 part by weight of 1, 4-butanediol diglycidyl ether; 2.2 parts by weight of pentaerythritol diisodecyl diphosphite; 2.0 parts by weight of gamma-glycidyl ether oxypropyltrimethoxysilane;
the preparation method of the composite stabilizer comprises the following steps: adding the methyl chloro-palm oil into a stainless steel reaction kettle, heating to 50 ℃, adding other raw materials according to the formula components, mixing and stirring for 1.0h, and cooling to normal temperature to obtain the composite plasticizer.
And (3) performance testing:
(1) and (3) high temperature resistance test:
the high temperature resistance of the compounded plasticizer was measured according to the method of example 1, and the results are shown in Table 4.
TABLE 4 test results of high temperature resistance of composite plasticizer
| Plasticizer | The product begins to yellow (min) | The product begins to turn black (min) |
| Compound plasticizer | 13 | 17.5 |
| Dioctyl phthalate | 10 | 15 |
As can be seen from the data in Table 3, the composite plasticizer of the present invention has better high temperature resistance than dioctyl phthalate.
(2) Flame retardancy test
The flame retardancy test was carried out according to the method of example 1, and the flame retardancy grade of the obtained PVC product was B1.
The results of the above examples show that the heat resistance of the composite plasticizer provided by the invention is superior to that of dioctyl phthalate, and the composite plasticizer can replace dioctyl phthalate in PVC high-temperature industry, and the obtained product has high flame retardant grade, good environmental protection, good compatibility with PVC, low price and wide application prospect.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. The environment-friendly high-temperature-resistant composite plasticizer is characterized by comprising the following components in parts by mass: 80-85 parts of methyl chloro-palm oil, 10-15 parts of epoxy vegetable oil, 0.1-1 part of epoxy resin active diluent, 0.1-3 parts of antioxidant and 0.1-2 parts of coupling agent.
2. The environment-friendly high-temperature-resistant composite plasticizer according to claim 1, wherein the epoxy vegetable oil comprises one or more of epoxy rice bran oil, epoxy linseed oil and epoxy rapeseed oil.
3. The environment-friendly high-temperature-resistant composite plasticizer according to claim 1, wherein the epoxy resin reactive diluent comprises one or more of hexanediol diglycidyl ether, 1, 4-butanediol diglycidyl ether, and polypropylene glycol diglycidyl ether.
4. The environment-friendly high-temperature-resistant composite plasticizer according to claim 1, wherein the antioxidant comprises pentaerythritol diisodecyl diphosphite and/or trialkyl phosphite.
5. The environment-friendly high-temperature-resistant composite plasticizer according to claim 1, wherein the coupling agent comprises a silane coupling agent.
6. The environment-friendly high-temperature-resistant composite plasticizer according to claim 5, wherein the silane coupling agent comprises gamma-glycidoxypropyltrimethoxysilane and/or gamma-mercaptopropyltrimethoxysilane.
7. The preparation method of the environment-friendly high-temperature-resistant composite plasticizer according to any one of claims 1 to 6, characterized by comprising the following steps:
heating the methyl chloro-palm oil, adding the epoxy vegetable oil, the epoxy resin active diluent, the antioxidant and the coupling agent, stirring, mixing and cooling to room temperature to obtain the environment-friendly high-temperature-resistant composite plasticizer.
8. The method according to claim 7, wherein the heating temperature is 45 to 50 ℃.
9. The preparation method according to claim 7 or 8, wherein the stirring and mixing time is 0.5-1.0 h.
10. The use of the environment-friendly high-temperature-resistant composite plasticizer according to any one of claims 1 to 6 in polyvinyl chloride products.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111875902A (en) * | 2020-08-03 | 2020-11-03 | 宜兴市鸿韵塑料有限公司 | PVC cable material |
| CN113604057A (en) * | 2021-07-20 | 2021-11-05 | 安徽力天环保科技股份有限公司 | Preparation method of composite plasticizer |
| CN114277611A (en) * | 2021-12-31 | 2022-04-05 | 佛山荷韵特种材料有限公司 | Special explosion-proof flower cover oil for ceramic stained paper, production process of special explosion-proof flower cover oil and ceramic stained paper |
-
2020
- 2020-03-05 CN CN202010146553.3A patent/CN111269580A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111875902A (en) * | 2020-08-03 | 2020-11-03 | 宜兴市鸿韵塑料有限公司 | PVC cable material |
| CN113604057A (en) * | 2021-07-20 | 2021-11-05 | 安徽力天环保科技股份有限公司 | Preparation method of composite plasticizer |
| CN114277611A (en) * | 2021-12-31 | 2022-04-05 | 佛山荷韵特种材料有限公司 | Special explosion-proof flower cover oil for ceramic stained paper, production process of special explosion-proof flower cover oil and ceramic stained paper |
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Application publication date: 20200612 |