CN110760022A - Thermal-stable vinyl chloride polymerization terminator, and preparation method and application thereof - Google Patents
Thermal-stable vinyl chloride polymerization terminator, and preparation method and application thereof Download PDFInfo
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- CN110760022A CN110760022A CN201810823056.5A CN201810823056A CN110760022A CN 110760022 A CN110760022 A CN 110760022A CN 201810823056 A CN201810823056 A CN 201810823056A CN 110760022 A CN110760022 A CN 110760022A
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- 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
- C08F114/00—Homopolymers 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
- C08F114/02—Monomers containing chlorine
- C08F114/04—Monomers containing two carbon atoms
- C08F114/06—Vinyl chloride
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
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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
- C08K5/49—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
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention belongs to the field of resin synthesis, and particularly relates to a thermal-stable vinyl chloride polymerization terminator, and a preparation method and application thereof. The method comprises the following raw materials: n-isopropylhydroxylamine, hydrotalcite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, deionized water, a dispersant and an emulsifier; wherein: the hydrotalcite is: MgO/Al2O33.0 to 4.0, an average particle diameter of 10 to 20nm, and a specific surface area of 15 to 20m2(ii) in terms of/g. The terminator of the invention has good vinyl chloride polymerization termination effect, effectively reduces the damage of residual initiator to the thermal stability of PVC resin,the invention can improve the thermal stability of PVC resin, prolong the thermal stability time of the resin, and does not influence the transparency of PVC products.
Description
Technical Field
The invention belongs to the field of resin synthesis, and particularly relates to a thermal-stable vinyl chloride polymerization terminator, and a preparation method and application thereof.
Background
The terminating agent stops or significantly reduces the reaction rate by combining with residual initiator reactive radicals and residual initiator to form inactive compounds, which effectively protects the polymer from damage by thermal oxygen aging during stripping and subsequent processing. The terminator is added when the polymerization reaction reaches a set end point, and commonly used terminators are bisphenol A, thiosemicarbazone, BHT, and the like. A single terminator often cannot meet the requirements of efficiently terminating the polymerization reaction and improving the thermal stability of the resin at the same time, and the terminator is developing towards the functional compound direction of both chain termination and improving the thermal stability of PVC.
CN201110380532 discloses a preparation method and a use method of a polyvinyl chloride resin terminator, wherein the terminator is an oil-soluble composite liquid terminator and is mainly compounded by HKY-10, a benzofuranone antioxidant and a phosphite antioxidant. Wherein HKY-10 is a liquid antioxidant prepared by dissolving 2, 6-di-tert-butyl-4- (1-phenylethyl) phenol in an organic solvent. The aging whiteness of the PVC resin product can be improved by using the terminator. The formulation used in this patent is different from the present patent. The terminator of the invention introduces an organic solvent, and can potentially influence the production and polymerization of PVC.
CN102617765B discloses a method for producing chlorinated polyvinyl chloride with excellent thermal stability, which is realized by adding a thermal stabilizer dispersion to chlorinated polyvinyl chloride resin at the later stage of the chlorination process, wherein the thermal stabilizer dispersion is prepared from an organic tin stabilizer and a dialkyl substituted hydroxylamine terminator. The effect of the heat stabilizer dispersion liquid on improving the heat stability of the CPVC resin in an aqueous phase suspension method is better than that of the single use of antioxidants such as alkyl substituted hydroxylamine terminators or hindered phenol and the like. The auxiliary agent used in the patent is different from the invention patent, and the phenolic antioxidant used in the invention is toxic.
CN201610153540 discloses a PVC oil-soluble terminator and a preparation method thereof, which comprises the following raw materials in parts by weight: epoxidized soybean oil: 5-50 parts of an antioxidant: 10-30 parts of bisphenol A: 10-40 parts of a solid terminator: 1-20 parts of a stabilizer: 5-40 parts of a plasticizer: 1-40 parts of styrene: 5-45 parts of solvent oil: 5-25 parts of methanol solution: 5-40 parts. The PVC resin oil-soluble terminator obtained by the invention has good termination effect and long thermal stability time, and the solid material is added into the reaction vessel at one time during preparation, so that the reaction time is greatly shortened, the reaction temperature is lower, the energy consumption is reduced, and the production capacity of a production device is improved. The formula and the process used by the invention are different from the patent of the invention, and the oil-soluble terminator contains bisphenol A with higher toxicity, which runs counter to the development direction of green environmental protection of the terminator.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a thermal stable type vinyl chloride polymerization terminator, which has a good vinyl chloride polymerization termination effect, can effectively reduce the damage of residual initiator to the thermal stability of PVC resin, can improve the thermal stability of the PVC resin, prolongs the thermal stability time of the resin, and does not influence the transparency of PVC products, and also provides a preparation method and application thereof.
The thermal stable vinyl chloride polymerization terminator provided by the invention comprises N-isopropylhydroxylamine, hydrotalcite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, deionized water, a dispersant and an emulsifier; wherein: the hydrotalcite is: MgO/Al2O33.0 to 4.0, an average particle diameter of 10 to 20nm, and a specific surface area of 15 to 20m2/g。
The average particle diameter is preferably 20nm,the specific surface area is preferably 16m2/g。
The dispersing agent is a hydroxypropyl methyl cellulose aqueous solution with the methoxyl content of 28-30%, the hydroxypropyl content of 7.5-12% and the concentration of 2-3%.
The emulsifier is one or more of polyoxyethylene polyol alkyl ester, sodium dodecyl benzene sulfonate, sodium dodecyl sulfate, polyoxyethylene sorbitan monooleate, sorbitan trioleate or polyoxyethylene sorbitan monolaurate, and preferably polyoxyethylene polyol alkyl ester.
The thermal stable vinyl chloride polymerization terminator disclosed by the invention preferably comprises the following raw materials in parts by weight: 20-30 parts of N-isopropylhydroxylamine; 30-40 parts of hydrotalcite; 20-30 parts of bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite; 60-70 parts of deionized water; 1-3 parts of a dispersing agent and 0.1-0.5 part of an emulsifying agent.
The preparation method of the thermal stable vinyl chloride polymerization terminator comprises the following steps: the method comprises the following steps: mixing and stirring hydrotalcite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite and deionized water for 10-20 min, sequentially adding a dispersing agent, an emulsifier and N-isopropylhydroxylamine, uniformly stirring, and pouring into a high-speed shearing emulsifying machine to emulsify at the rotating speed of 1500-3000 r/min for 20-30 min to obtain the thermal stable vinyl chloride polymerization terminator.
The application of the thermal stable type vinyl chloride polymerization terminator comprises the steps of adding desalted water, a polyvinyl alcohol PVA70 aqueous solution with the concentration of 5%, a hydroxypropyl methyl cellulose E50 aqueous solution with the concentration of 3%, tert-butyl peroxyneodecanoate and tert-amyl peroxypivalate into a reaction kettle, pumping the pressure in the kettle to be lower than-0.09 MPa, adding vinyl chloride monomer, starting stirring, stirring and mixing at normal temperature, heating, reacting, and filling the thermal stable type vinyl chloride polymerization terminator into the kettle when the pressure in the kettle is reduced by 0.25-0.35 MPa.
Preferably, the reaction kettle is a 5L stainless steel pressure reaction kettle provided with two layers of double-blade flat pulp.
Preferably, vinyl chloride monomer is added, stirring is started, the rotating speed is controlled to be 450-480 rpm, stirring and mixing are carried out for 10-15 min at normal temperature, then the temperature is raised to 58.0 +/-0.2 ℃, the reaction is started for timing after the temperature is stabilized, and the thermal stable vinyl chloride polymerization terminator is added into the kettle when the pressure in the kettle is reduced by 0.25-0.35 MPa.
As a preferable technical scheme, the application of the thermal stable vinyl chloride polymerization terminator provided by the invention comprises the steps of adding 1.8-2.4 kg of desalted water, 8-10 g of 5% polyvinyl alcohol PVA80 aqueous solution, 6.3-6.5 g of 3% hydroxypropyl methyl cellulose E50 aqueous solution, 0.255-0.267 g of 75% tert-butyl peroxyneodecanoate and 0.500-0.533 g of 75% tert-amyl peroxypivalate into a reaction kettle, pumping the pressure in the kettle to be lower than-0.09 MPa, adding 1kg of vinyl chloride monomer, starting stirring, controlling the rotation speed to be 440-470 rpm, stirring and mixing for 10-15 min at normal temperature, raising the temperature of the kettle to 58.0 +/-0.2 ℃, starting reaction after the temperature is stable, and injecting the thermal stable vinyl chloride polymerization terminator into the kettle when the pressure in the kettle is reduced by 0.25-0.35 MPa.
The addition amount of the thermal stable type vinyl chloride polymerization terminator is 400-700 ppm based on the weight of vinyl chloride.
Compared with the prior art, the invention has the following advantages:
(1) the invention adopts N-isopropyl hydroxylamine and hydrotalcite (MgO/Al)2O33.0 to 4.0, an average particle diameter of about 20nm, and a specific surface area of 16m2The/g) and bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, dispersant and emulsifier form a composite terminator, and the components have a synergistic effect. The hydrotalcite has small particle size and large specific surface area, can carry a certain amount of N-isopropylhydroxylamine terminator and bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite to enter the interior of resin particles through pores among PVC resin sub-particles, improves the concentration of N-isopropylhydroxylamine and bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite in the resin particles, can rapidly terminate the polymerization reaction in the resin particles and react with residual initiator in the resin particles, has good vinyl chloride polymerization termination effect, and effectively reduces the thermal stability of the residual initiator to PVC resinAnd (4) destructive destruction. Meanwhile, hydrotalcite and bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite staying among pores of the resin can improve the thermal stability of the PVC resin, prolong the thermal stability time of the resin, and do not affect the transparency of PVC products.
(2) The thermal-stable vinyl chloride polymerization terminator not only can play a good vinyl chloride polymerization terminating effect and improve the thermal stability of the resin, but also does not influence the transparency of the resin.
Detailed Description
The present invention will be further described with reference to the following examples.
Examples 1 to 5
A thermally stable terminator for vinyl chloride polymerization having the components and contents shown in Table 1 in examples 1 to 5.
The material components were weighed according to the ratios in table 1. Putting 30-40 g of hydrotalcite, 20-30 g of bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, 0.1-0.5 g of polyoxyethylene polyol alkyl ester, and 60-70 g of deionized water into a glass beaker, stirring for 10 minutes, sequentially adding 1-3 g of hydroxypropyl methyl cellulose and 20-30 g N-isopropyl hydroxylamine, stirring uniformly, pouring into a high-speed shearing emulsifying machine, and emulsifying for 50 minutes at the rotation speed of 4000r/min to obtain the thermal stable vinyl chloride composite terminator with each component uniformly and stably existing in the emulsion.
TABLE 1
Note: MgO/Al of hydrotalcite used in examples2O33.5, average particle diameter of about 20nm, specific surface area of 16m2/g。
The heat-stable type terminating agent for vinyl chloride polymerization prepared in examples 1 to 5 was used to terminate vinyl chloride polymerization.
The method is implemented according to the following processes and conditions: 2.2kg of desalted water, 8g of a 5% aqueous polyvinyl alcohol PVA70 solution, 6.7g of a 3% aqueous hydroxypropyl methylcellulose E50 solution, 0.260g of tert-butyl peroxyneodecanoate having a content of 75% and 0.530g of tert-amyl peroxypivalate having a content of 75% were placed in a 5L stainless steel autoclave equipped with two layers of bilobalt pulp. Pumping the pressure in the kettle to be lower than-0.09 MPa, adding 1kg of vinyl chloride monomer, starting stirring, controlling the rotating speed at 470rpm, stirring and mixing for 10-15 min at normal temperature, raising the temperature of the kettle to 58.0 +/-0.2 ℃, and starting reaction timing after the temperature is stable. When the pressure in the autoclave had dropped by 0.30MPa, 1g of a terminator was charged into the autoclave. The temperature of the polymerization kettle is continuously controlled to be 58 +/-0.5 ℃, and the pressure drop in the polymerization kettle within 60min is observed and recorded to represent the terminating efficiency of the terminating agent (the smaller the pressure drop is, the higher the terminating efficiency of the terminating agent is, and the lower the terminating efficiency is, the reverse is). And recovering unreacted vinyl chloride monomer in the polymerization kettle, centrifugally dewatering the obtained slurry, and drying in a 60 ℃ circulating air drying oven for 6 hours to obtain PVC resin powder. The prepared PVC resin powder is subjected to Congo red thermal stability time test according to GB/T2917.1-2002.
Comparative examples 1 to 5:
the components of the materials are weighed according to the mixture ratio shown in the table 2, and the terminating agent is emulsified and compounded according to the process conditions of the embodiments 1 to 5.
TABLE 2 COMPARATIVE EXAMPLES 1 TO 6 (in parts by mass)
Note: MgO/Al of general hydrotalcite employed2O32, an average particle diameter of 100nm and a specific surface area of 7m2/g。
The methods and conditions for evaluating the terminators prepared in comparative examples 1 to 6 are the same as in examples, i.e., the terminators prepared in comparative examples 1 to 6 are used for terminating the polymerization of vinyl chloride. The amount of the terminator added was also 1 g. The test method of the thermal stability of the PVC resin congo red is the same as that of the example.
The termination efficiency of the terminators obtained in examples and comparative examples, and the Congo red heat-stable time of the resin are shown in Table 3.
TABLE 3 termination efficiency of the terminator, Congo Red thermal stability time of the resin
As can be seen from the examples, N-isopropylhydroxylamine, hydrotalcite (MgO/Al) were used2O33.0 to 4.0, an average particle diameter of about 20nm, and a specific surface area of 16m2The composite terminator composed of the bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite has a synergistic effect, and can not only achieve a good vinyl chloride polymerization terminating effect, but also effectively improve the thermal stability time of the resin. As can be seen from the comparative examples, the use of either or both of N-isopropylhydroxylamine, bis (2, 4-di-t-butylphenyl) pentaerythritol diphosphite and hydrotalcite alone does not provide both high termination efficiency and resin thermal stability. The use of N-isopropylhydroxylamine, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite and general-purpose hydrotalcite did not have a synergistic effect.
Claims (10)
1. A thermally stable vinyl chloride polymerization terminator characterized in that: the method comprises the following raw materials: n-isopropylhydroxylamine, hydrotalcite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, deionized water, a dispersant and an emulsifier; wherein: the hydrotalcite is: MgO/Al2O33.0 to 4.0, an average particle diameter of 10 to 20nm, and a specific surface area of 15 to 20m2/g。
2. A thermally stable vinyl chloride polymerization terminator according to claim 1, characterized in that: the dispersing agent is a hydroxypropyl methyl cellulose aqueous solution with the methoxyl content of 28-30%, the hydroxypropyl content of 7.5-12% and the concentration of 2-3%.
3. A thermally stable vinyl chloride polymerization terminator according to claim 1, characterized in that: the emulsifier is one or more of polyoxyethylene polyol alkyl ester, sodium dodecyl benzene sulfonate, sodium dodecyl sulfate, polyoxyethylene sorbitan monooleate, sorbitan trioleate or polyoxyethylene sorbitan monolaurate.
4. A thermally stable vinyl chloride polymerization terminator according to claim 1, characterized in that: the composite material comprises the following raw materials in parts by weight: 20-30 parts of N-isopropylhydroxylamine; 30-40 parts of hydrotalcite; 20-30 parts of bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite; 60-70 parts of deionized water; 1-3 parts of a dispersing agent and 0.1-0.5 part of an emulsifying agent.
5. A method for preparing a heat-stable vinyl chloride polymerization terminator as set forth in any one of claims 1 to 4, characterized in that: the method comprises the following steps: mixing and stirring hydrotalcite, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite and deionized water for 10-20 min, sequentially adding a dispersing agent, an emulsifier and N-isopropylhydroxylamine, uniformly stirring, and pouring into a high-speed shearing emulsifying machine to emulsify at the rotating speed of 1500-3000 r/min for 20-30 min to obtain the thermal stable vinyl chloride polymerization terminator.
6. Use of a thermally stable vinyl chloride polymerization terminator as claimed in any one of claims 1 to 4, characterized in that: adding desalted water, a polyvinyl alcohol PVA70 aqueous solution, a hydroxypropyl methyl cellulose E50 aqueous solution, tert-butyl peroxyneodecanoate and tert-amyl peroxypivalate into a reaction kettle, pumping the pressure in the kettle to be lower than-0.09 MPa, adding a vinyl chloride monomer, starting stirring, stirring and mixing at normal temperature, heating, reacting, and when the pressure in the kettle is reduced by 0.25-0.35 MPa, adding the thermal stable vinyl chloride polymerization terminator into the kettle.
7. Use according to claim 6, characterized in that: the reaction kettle is a 5L stainless steel pressure reaction kettle provided with two layers of double-blade flat slurry.
8. Use according to claim 6, characterized in that: adding vinyl chloride monomer, starting stirring, controlling the rotating speed at 450-480 rpm, stirring and mixing for 10-15 min at normal temperature, then heating to 58.0 +/-0.2 ℃, starting reaction timing after the temperature is stable, and filling the thermal stable vinyl chloride polymerization terminator into the kettle when the pressure in the kettle is reduced by 0.25-0.35 MPa.
9. Use according to claim 3, characterized in that: adding 1.8-2.4 kg of desalted water, 8-10 g of 5% polyvinyl alcohol PVA80 aqueous solution, 6.3-6.5 g of 3% hydroxypropyl methyl cellulose E50 aqueous solution, 0.255-0.267 g of 75% tert-butyl peroxyneodecanoate and 0.500-0.533 g of 75% tert-amyl peroxypivalate into a reaction kettle, pumping the pressure in the kettle to be lower than-0.09 MPa, adding 1kg of vinyl chloride monomer, starting stirring at the rotating speed of 440-470 rpm, stirring and mixing for 10-15 min at normal temperature, raising the temperature of the kettle to 58.0 +/-0.2 ℃, starting reaction after the temperature is stabilized, and injecting the thermal stable vinyl chloride polymerization terminator into the kettle when the pressure in the kettle is reduced by 0.25-0.35 MPa.
10. Use according to claim 9, characterized in that: the addition amount of the thermal stable type vinyl chloride polymerization terminator is 400-700 ppm based on the weight of vinyl chloride.
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