CN113968927A - Method for synthesizing low molecular weight styrene-maleic anhydride resin by tubular reactor - Google Patents
Method for synthesizing low molecular weight styrene-maleic anhydride resin by tubular reactor Download PDFInfo
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Abstract
The invention provides a method for synthesizing a low molecular weight styrene-maleic anhydride copolymer by a tubular reactor, which comprises the following steps: dissolving styrene and maleic anhydride in a solvent to divide the solution into two groups to obtain two reaction solutions; and mixing the two reaction liquids through different feeding pipelines according to a certain flow rate ratio, so that the styrene, the maleic anhydride and the initiator react in a tubular reactor in a specific ratio all the time, and the low-molecular-weight styrene-maleic anhydride alternating copolymer is prepared. The method has the advantages of simple process, stable heat release in the reaction process, easy reaction control, economy, environmental protection and the like.
Description
Technical Field
The invention belongs to the field of polymer synthesis, and particularly relates to a method for synthesizing low molecular weight styrene-maleic anhydride resin by using a tubular reactor.
Background
The styrene-maleic anhydride resin with low molecular weight and narrow molecular weight distribution is a polymer with wide application, and can be respectively used as a paper surface sizing agent, an organic pigment dispersant, an emulsion polymerization protective colloid and the like in industries such as papermaking, spinning, printing and dyeing, coating, chemical engineering and the like.
At present, the preparation methods of styrene-maleic anhydride copolymers are mainly solution polymerization, small amount of bulk polymerization, bulk-suspension polymerization and precipitation polymerization. However, these methods are difficult to obtain a polymer having a low molecular weight and a narrow molecular weight distribution.
Atom Transfer Radical Polymerization (ATRP) and Reversible Addition-Fragmentation Chain Transfer Polymerization (RAFT) are commonly used to synthesize low molecular weight and narrow molecular weight distribution styrene-maleic anhydride resins. However, there are disadvantages that the operation process is complicated and the RAFT agent is expensive, which limits industrial application.
Tubular reactors, also known as plug flow reactors, have been developed since 1940. The tubular reactor is tubular, has large length-diameter ratio and belongs to a continuous operation reactor. The method can be divided into 3 types of intermittent, continuous and semi-continuous modes according to different operation modes. Although stirred tank reactors are the most widely used in industry, stirred tank reactors are not suitable for rapid reactions requiring very short residence times and high intensity local mixing. Therefore, other intensive mixing reactors are successively considered in place of stirred tank reactors. The tubular reactor has the advantages of short feeding residence time, capability of realizing local mixing with certain strength, simple structure, convenient processing, large heat transfer area, high heat transfer coefficient, high pressure resistance, safety, high efficiency and the like.
The invention aims to overcome the defects of the prior art and provide a method for synthesizing a low-molecular-weight (the number average molecular weight is controlled within the range of 4000-9000) narrow-distribution (PDI is less than 2.20) styrene-maleic anhydride resin by using a tubular reactor.
Disclosure of Invention
The invention utilizes a tubular reactor to synthesize a low molecular weight styrene-maleic anhydride resin product, which is characterized in that: the method comprises the following steps of (1),
(1) adding an initiator and styrene into a solvent under stirring to serve as a reaction material A, adding the initiator and maleic anhydride into the solvent to serve as a reaction material B, and reducing the content of oxygen dissolved in the reaction materials A and B to be below 2ppm through a nitrogen system respectively;
(2) respectively introducing the materials A and B into the tubular reactor through a metering pump for mixing and reacting, controlling the set temperature by an external heat exchanger, taking heat transfer oil as a heat exchange medium, and changing the retention time through flow control;
(3) and after the reaction is finished, drying the reaction liquid in the receiving tank to obtain a styrene-maleic anhydride resin product, wherein the total yield of the product is 92-97%, the number average molecular weight is controlled within the range of 4000-9000, and the molecular weight distribution is less than 2.20.
Wherein the initiator in the step (1) is one or more of azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide and di-tert-butyl peroxide.
Wherein the solvent in the step (1) comprises one or more selected from butanone, methyl acetone, 2-pentanone, 3-methyl-2-butanone, 2-hexanone, 3-hexanone, 2-methyl-3-pentanone, 3-dimethyl-2-butanone, 4-methyl-2-pentanone, 2-heptanone, 3-heptanone, 4-heptanone, 2, 4-dimethyl-3-pentanone, 2-octanone, 2, 6-dimethyl-4-heptanone, cyclopentanone, cyclohexanone or cycloheptanone.
The mass of the initiator in the step (1) is 1-5% of the total mass of the styrene and the maleic anhydride, the molar ratio of the maleic anhydride to the styrene is 1: 1-5, and the mass ratio of the total mass of the styrene, the maleic anhydride and the initiator to the solvent is 1: 1-3.
Wherein the flow rate of the reaction material A in the step (2) is 20mL/min to 40mL/min, and the flow rate of the reaction material B is 5mL/min to 25 mL/min.
Wherein the reaction residence time of the materials in the tubular reactor in the step (2) is preferably 400-700 s, the reaction temperature is 70-100 ℃, and the pressure is 1.5-3 MPa.
The tubular reactor used in the invention comprises a batching tank, a raw material pump, a pressure gauge, a straight tubular reactor, an oil bath pot, a cooling coil, a back pressure valve and a product collecting tank. The thermocouple is arranged in the heat-conducting medium and can be used for measuring the actual temperature of the external heat-conducting medium. The module is made of monocrystalline silicon, special glass, ceramics, stainless steel or metal alloy coated with a corrosion-resistant coating, polytetrafluoroethylene and the like. The reaction system can resist corrosion and pressure, and the pressure resistance is different according to different materials. The diameter of the tubular reactor is 5 mm-15 mm.
The number average molecular weight of the styrene-maleic anhydride resin obtained by the method is controlled within the range of 4000-9000, and the molecular weight distribution is less than 2.20.
Compared with the prior art, the invention has the following main characteristics:
1. the invention adopts a tubular continuous flow reactor of continuous flow, the reaction time is shortened from a traditional plurality of hours to a plurality of minutes to more than ten minutes, and the reaction efficiency is obviously improved.
2. Because the raw materials are mixed well in the tubular passage, the temperature is controlled accurately, the amount of the initiator can be greatly reduced in the reaction process, the generation of impurities is reduced, and the molecular weight distribution of the product is obviously narrowed.
3. The tubular reactor used in the invention is made of stainless steel, the metering pump is made of polytetrafluoroethylene and titanium, the corrosion resistance is excellent, and the problem of serious equipment corrosion in the conventional reactor is avoided.
4. In the tubular reactor, the whole process of feeding, mixing and reaction is continuous flow reaction, so that the phenomenon that the device needs to be additionally configured and the leakage occurs in the transfer in the conventional intermittent reaction is avoided, the environment is protected, the safety is realized, and the production efficiency is high.
Drawings
FIG. 1 is a process flow diagram for synthesizing styrene-maleic anhydride resin products according to the present invention: 1-a first batching tank, 2-a second batching tank, 3-a first raw material pump, 4-a second raw material pump, 5-a first pressure gauge, 6-a second pressure gauge, 7-a tubular reactor, 8-an oil bath pot, 9-a cooling coil, 10-a back pressure valve and 11-a product collecting tank.
Detailed Description
The invention is further illustrated by the accompanying drawings and detailed description, but the invention is not limited thereto.
The invention utilizes a tubular reactor to synthesize a low molecular weight styrene-maleic anhydride resin product, which is characterized in that: the method comprises the following steps of (1),
(1) adding an initiator and styrene into a solvent under stirring to serve as a reaction material A, adding the initiator and maleic anhydride into the solvent to serve as a reaction material B, and reducing the content of oxygen dissolved in the reaction materials A and B to be below 2ppm through a nitrogen system respectively;
(2) respectively introducing the materials A and B into the tubular reactor through a metering pump for mixing and reacting, controlling the set temperature by an external heat exchanger, taking heat transfer oil as a heat exchange medium, and changing the retention time through flow control;
(3) and after the reaction is finished, drying the reaction liquid in the receiving tank to obtain a styrene-maleic anhydride resin product, wherein the total yield of the product is 92-97%, the number average molecular weight is controlled within the range of 4000-9000, and the molecular weight distribution is less than 2.20.
Wherein the initiator in the step (1) is one or more of azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide and di-tert-butyl peroxide.
Wherein the solvent in the step (1) comprises one or more selected from butanone, methyl acetone, 2-pentanone, 3-methyl-2-butanone, 2-hexanone, 3-hexanone, 2-methyl-3-pentanone, 3-dimethyl-2-butanone, 4-methyl-2-pentanone, 2-heptanone, 3-heptanone, 4-heptanone, 2, 4-dimethyl-3-pentanone, 2-octanone, 2, 6-dimethyl-4-heptanone, cyclopentanone, cyclohexanone or cycloheptanone.
The mass of the initiator in the step (1) is 1-5% of the total mass of the styrene and the maleic anhydride, the molar ratio of the maleic anhydride to the styrene is 1: 1-5, and the mass ratio of the total mass of the styrene, the maleic anhydride and the initiator to the solvent is 1: 1-3.
Wherein the flow rate of the reaction material A in the step (2) is 20mL/min to 40mL/min, and the flow rate of the reaction material B is 5mL/min to 25 mL/min.
Wherein the reaction residence time of the materials in the tubular reactor in the step (2) is preferably 400-700 s, the reaction temperature is 70-100 ℃, and the pressure is 1.5-3 MPa.
Referring to fig. 1, the process flow of the present invention comprises the following steps: (1) respectively introducing nitrogen into a first preparation tank 1 and a second preparation tank 2 filled with a monomer solution and an initiator for 40min, and reducing the oxygen content dissolved in the solution to be below 2 ppm; (2) respectively opening a first raw material pump 3 and a second raw material pump 4 to enable the solutions in a first batching tank 1 and a second batching tank 2 to pass through a tubular reactor 7 at a certain flow rate for reaction, controlling the temperature through an oil bath pot 8, monitoring the system pressure through a first pressure gauge 5 and a second pressure gauge 6 in the whole process, and adjusting the pipeline pressure through a back pressure valve 10; (3) after the reaction liquid is cooled by a cooling coil 9, a styrene-maleic anhydride resin product is obtained after the reaction liquid is collected and dried by a product collecting tank 11, and the molecular weight and the distribution of the product are tested by using GPC.
Example 1
77.6g of maleic anhydride, 6.3g of azobisisobutyronitrile and 120g of butanone are added into a first preparation tank 1 to prepare a reaction liquid A; 82.3g of styrene, 1.7g of azobisisobutyronitrile and 120g of butanone are added into a second batching tank 2 to prepare reaction liquid B; the polymerization monomer mixed solution was maintained at 10 ℃. And respectively introducing nitrogen into the first preparation tank 1 and the second preparation tank 2 for 40min, removing oxygen mixed in the monomer mixed solution, and controlling the oxygen mass in the monomer mixed solution to be less than 2 ppm. The materials are respectively sent into a tubular reactor 7 through a first raw material pump 3 and a second raw material pump 4 at the speed of 22mL/min, the system pressure is monitored through a first pressure gauge 5 and a second pressure gauge 6 in the whole process, and the pipeline pressure is adjusted to be 2MPa through a backpressure valve 10. The polymerization temperature in the tubular reactor 7 was controlled to 80 ℃ by means of an oil bath 8 and the reaction residence time was 545 s. And the reaction product flows out of the reactor in a continuous flow state after passing through the cooling coil 9 in ice-water bath, and the reaction liquid is collected and dried by the product collecting tank 11 to obtain the colorless transparent polymer. The overall yield of the product was found to be about 96.5%, the number average molecular weight was 4345, and the molecular weight distribution PDI was 1.91.
Example 2
Adding 51.7g of maleic anhydride, 2.67g of azobisisobutyronitrile and 80g of butanone into a first preparation tank 1 to prepare a reaction liquid A; 109.8g of styrene, 5.33g of azobisisobutyronitrile and 160g of butanone are added into a second batching tank 2 to prepare reaction liquid B; the polymerization monomer mixed solution was maintained at 10 ℃. And respectively introducing nitrogen into the first dosing tank 1 and the second dosing tank 2 for 40min, and controlling the oxygen mass in the nitrogen to be reduced to below 2 ppm. The reaction solution A and the reaction solution B were fed into the tubular reactor 7 at 14.5mL/min and 29mL/min by the first raw material pump 3 and the second raw material pump 4, respectively, the system pressure was monitored by the first pressure gauge 5 and the second pressure gauge 6 in the whole process, and the line pressure was adjusted to 2.2MPa by the back pressure valve 10. The polymerization temperature in the tubular reactor 7 was controlled to 80 ℃ by means of an oil bath pot 8, and the reaction residence time was 537 s. And the reaction product flows out of the reactor in a continuous flow state after passing through the cooling coil 9 in ice-water bath, and the reaction liquid is collected and dried by the product collecting tank 11 to obtain the colorless transparent polymer. The overall yield of the product was found to be about 95.3%, the number average molecular weight was 5927, and the molecular weight distribution PDI was 1.83.
Example 3
Adding 38.8g of maleic anhydride, 2g of azobisisobutyronitrile and 60g of butanone into a first batching tank 1 to prepare a reaction solution A; 123.6g of styrene, 6g of azodiisobutyronitrile and 180g of butanone are added into the second batching tank 2 to prepare reaction liquid B; the polymerization monomer mixed solution was maintained at 10 ℃. And respectively introducing nitrogen into the first preparation tank 1 and the second preparation tank 2 for 40min, removing oxygen mixed in the monomer mixed solution, and controlling the oxygen mass in the monomer mixed solution to be less than 2 ppm. The reaction liquid A and the reaction liquid B were fed into the tubular reactor 7 at speeds of 11.1mL/min and 33.2mL/min by the first raw material pump 3 and the second raw material pump 4, respectively, the system pressure was monitored by the first pressure gauge 5 and the second pressure gauge 6 in the whole process, and the line pressure was adjusted to 2.3MPa by the back pressure valve 10. The polymerization temperature in the tubular reactor 7 was controlled to 80 ℃ by means of an oil bath 8 and the reaction residence time was 528 s. And the reaction product flows out of the reactor in a continuous flow state after passing through the cooling coil 9 in ice-water bath, and the reaction liquid is collected and dried by the product collecting tank 11 to obtain the colorless transparent polymer. The overall yield of the product was found to be about 94.7%, the number average molecular weight was 6713, and the molecular weight distribution PDI was 2.07.
Example 4
31.1g of maleic anhydride, 1.6g of azobisisobutyronitrile and 48g of butanone are added into a first batching tank 1 to prepare a reaction liquid A; 132g of styrene, 6.4g of azobisisobutyronitrile and 192g of butanone are added into a second batching tank 2 to prepare reaction liquid B; the polymerization monomer mixed solution was maintained at 10 ℃. And respectively introducing nitrogen into the first dosing tank 1 and the second dosing tank 2 for 40min, and controlling the oxygen mass in the nitrogen to be reduced to below 2 ppm. The reaction liquid A and the reaction liquid B were fed into the tubular reactor 7 at speeds of 8.7mL/min and 35.6mL/min by the first raw material pump 3 and the second raw material pump 4, respectively, the system pressure was monitored by the first pressure gauge 5 and the second pressure gauge 6 in the whole process, and the line pressure was adjusted to 2.5MPa by the back pressure valve 10. The polymerization temperature in the tubular reactor 7 was controlled to 80 ℃ by means of an oil bath 8 and the reaction residence time was 521 s. And the reaction product flows out of the reactor in a continuous flow state after passing through the cooling coil 9 in ice-water bath, and the reaction liquid is collected and dried by the product collecting tank 11 to obtain the colorless transparent polymer. The overall yield of the product was found to be about 94.1%, the number average molecular weight was 7850, and the molecular weight distribution PDI was 1.95.
Example 5
Adding 25.9g of maleic anhydride, 1.33g of azobisisobutyronitrile and 40g of butanone into a first preparation tank 1 to prepare a reaction liquid A; adding 137.5g of styrene, 6.67g of azodiisobutyronitrile and 200g of butanone into the second batching tank 2 to prepare reaction liquid B; the polymerization monomer mixed solution was maintained at 10 ℃. And respectively introducing nitrogen into the first dosing tank 1 and the second dosing tank 2 for 40min, and controlling the oxygen mass in the nitrogen to be reduced to below 2 ppm. The reaction liquid A and the reaction liquid B were fed into the tubular reactor 7 at speeds of 7.3mL/min and 37.1mL/min by the first raw material pump 3 and the second raw material pump 4, respectively, the system pressure was monitored by the first pressure gauge 5 and the second pressure gauge 6 in the whole process, and the line pressure was adjusted to 2.7MPa by the back pressure valve 10. The polymerization temperature in the tubular reactor 7 was controlled to 80 ℃ by means of an oil bath 8, the reaction residence time was 519 s. And the reaction product flows out of the reactor in a continuous flow state after passing through the cooling coil 9 in ice-water bath, and the reaction liquid is collected and dried by the product collecting tank 11 to obtain the colorless transparent polymer. The overall yield of the product was found to be about 93.6%, the number average molecular weight was 8732, and the molecular weight distribution PDI was 2.11.
Comparative example 1
The same procedure as in example 1 was used. Except that the tubular reactor was changed to a complete mixing tank reactor with jacket and stirring. 120g of butanone is taken and put into a reaction kettle, nitrogen gas replacement is started, stirring is started, the temperature is increased to 80 ℃, nitrogen gas is introduced, and the pressure is increased to 0.1 MPa. Mixing 77.7g of maleic anhydride, 82.3g of styrene, 8g of azobisisobutyronitrile and 120g of butanone, dropwise adding into the reaction kettle at the speed of 3g/min, preserving heat for 2h after dropwise adding is finished, cooling to 40 ℃, and discharging. The reaction solution was dried to obtain a colorless transparent polymer, and the total yield of the product was found to be 94.5%, the number average molecular weight was 3621, and the molecular weight distribution PDI was found to be 5.04. In the complete mixing kettle type reactor, the viscosity of the system is obviously increased after 6 hours of polymerization. Analysis suggests that the molecular weight distribution of the resulting polymer is broadened due to local overheating of the system caused by unfavorable heat and mass transfer.
TABLE 1 Table of Property parameters for styrene-maleic anhydride products provided in the examples of the invention
| Examples | St:MAH | Mn | Mw | PDI | Yield (%) |
| 1 | 1:1 | 4345 | 8290 | 1.91 | 96.5 |
| 2 | 1:2 | 5927 | 10846 | 1.83 | 95.3 |
| 3 | 1:3 | 6713 | 13895 | 2.07 | 94.7 |
| 4 | 1:4 | 7850 | 15307 | 1.95 | 94.1 |
| 5 | 1:5 | 8732 | 18424 | 2.11 | 93.6 |
In the table: st represents styrene, MAH represents maleic anhydride, Mn represents the number average molecular weight, Mw represents the weight average molecular weight, and PDI represents the molecular weight distribution.
As can be seen from Table 1, the production process provided by the invention can be used for producing the styrene-maleic anhydride resin product with the molar ratio of maleic anhydride to styrene being 1: 1-5, the number average molecular weight of the product being 4000-9000 g/mol and the molecular weight distribution being less than 2.20. Under the same conditions, comparative example 1, which synthesized a styrene-maleic anhydride resin using a tank reactor, had a number average molecular weight Mn of 3621, a weight average molecular weight Mw of 18250, and a molecular weight distribution PDI as high as 5.04.
Therefore, the use of the tubular reactor enables the synthesis of low molecular weight, narrowly distributed styrene-maleic anhydride resin, compared to the tank reactor, thus illustrating the technical advancement of the present invention. And the final yield of the synthesis mode is over 93 percent, so the method is very suitable for the standard of industrial production, has simple production process, and is an economic, rapid and efficient synthesis production mode.
Claims (6)
1. A process for the synthesis of low molecular weight styrene-maleic anhydride resin in a tubular reactor, characterized in that: comprises the following steps of (a) carrying out,
(1) adding an initiator and styrene into a solvent under stirring to serve as a reaction material A, adding the initiator and maleic anhydride into the solvent to serve as a reaction material B, and reducing the content of oxygen dissolved in the reaction materials A and B to be below 2ppm through a nitrogen system respectively;
(2) respectively introducing the materials A and B into the tubular reactor through a metering pump for mixing and reacting, controlling the set temperature by an external heat exchanger, taking heat transfer oil as a heat exchange medium, and changing the retention time through flow control;
(3) and after the reaction is finished, drying the reaction liquid in the receiving tank to obtain a styrene-maleic anhydride resin product, wherein the total yield of the product is 92-97%, the number average molecular weight is controlled within the range of 4000-9000, and the molecular weight distribution is less than 2.20.
2. The tubular reactor synthesis process of low molecular weight styrene-maleic anhydride resin of claim 1, characterized in that: the initiator is one or more of azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide and di-tert-butyl peroxide.
3. The tubular reactor synthesis process of low molecular weight styrene-maleic anhydride resin of claim 1, characterized in that: the solvent comprises one or more of butanone, methyl acetone, 2-pentanone, 3-methyl-2-butanone, 2-hexanone, 3-hexanone, 2-methyl-3-pentanone, 3-dimethyl-2-butanone, 4-methyl-2-pentanone, 2-heptanone, 3-heptanone, 4-heptanone, 2, 4-dimethyl-3-pentanone, 2-octanone, 2, 6-dimethyl-4-heptanone, cyclopentanone, cyclohexanone or cycloheptanone.
4. The tubular reactor synthesis process of low molecular weight styrene-maleic anhydride resin of claim 1, characterized in that: the mass of the initiator is 1-5% of the total mass of the styrene and the maleic anhydride, the molar ratio of the maleic anhydride to the styrene is 1: 1-5, and the total mass of the styrene, the maleic anhydride and the initiator is 1: 1-3 of the mass of the solvent.
5. The tubular reactor synthesis process of low molecular weight styrene-maleic anhydride resin of claim 1, characterized in that: the flow rate of the reaction material A is 20 mL/min-40 mL/min, and the flow rate of the reaction material B is 5 mL/min-25 mL/min.
6. The tubular reactor synthesis process of low molecular weight styrene-maleic anhydride resin of claim 1, characterized in that: the reaction residence time of the materials in the tubular reactor is 400-700 s, the reaction temperature is 70-100 ℃, and the pressure is 1.5-3 MPa.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115353834A (en) * | 2022-09-05 | 2022-11-18 | 上海昶法新材料有限公司 | Preparation method of carpet adhesive |
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| JPS59115315A (en) * | 1982-12-21 | 1984-07-03 | Idemitsu Kosan Co Ltd | Production of copolymer |
| CN1142509A (en) * | 1995-07-03 | 1997-02-12 | Basf公司 | Continuous preparation of polyumers and apparatus for this purpose |
| US20050192414A1 (en) * | 2001-12-19 | 2005-09-01 | Donck Jan C. | Tubular polymerization reactors and polymers made therein |
| WO2009071999A2 (en) * | 2007-09-21 | 2009-06-11 | Exotech Bio Solutions Ltd. | Preparations of poly(styrene-co-maleic anhydride/acid) |
| CN103923247A (en) * | 2013-01-11 | 2014-07-16 | 上海飞凯光电材料股份有限公司 | Styrene-maleic anhydride copolymer production process |
| CN111234081A (en) * | 2020-03-06 | 2020-06-05 | 长春工业大学 | Low-molecular-weight narrow-distribution styrene-maleic anhydride copolymer and preparation method thereof |
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2021
- 2021-12-09 CN CN202111495859.0A patent/CN113968927A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59115315A (en) * | 1982-12-21 | 1984-07-03 | Idemitsu Kosan Co Ltd | Production of copolymer |
| CN1142509A (en) * | 1995-07-03 | 1997-02-12 | Basf公司 | Continuous preparation of polyumers and apparatus for this purpose |
| US20050192414A1 (en) * | 2001-12-19 | 2005-09-01 | Donck Jan C. | Tubular polymerization reactors and polymers made therein |
| WO2009071999A2 (en) * | 2007-09-21 | 2009-06-11 | Exotech Bio Solutions Ltd. | Preparations of poly(styrene-co-maleic anhydride/acid) |
| CN103923247A (en) * | 2013-01-11 | 2014-07-16 | 上海飞凯光电材料股份有限公司 | Styrene-maleic anhydride copolymer production process |
| CN111234081A (en) * | 2020-03-06 | 2020-06-05 | 长春工业大学 | Low-molecular-weight narrow-distribution styrene-maleic anhydride copolymer and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115353834A (en) * | 2022-09-05 | 2022-11-18 | 上海昶法新材料有限公司 | Preparation method of carpet adhesive |
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