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Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride

A technology of alkyl methacrylate and maleic anhydride, which is applied in lubricating compositions, liquid carbon-containing fuels, fuel additives, etc., and can solve problems such as low reactivity and low conversion rate of copolymers

Active Publication Date: 2017-08-29
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the special case where the comonomer is maleic anhydride, the challenge is even higher since the comonomer maleic anhydride is known to have low reactivity and since the known solution polymerization process has the disadvantage of The conversion of maleic anhydride to the resulting copolymer is low, usually an excess of maleic anhydride in the reaction solution is used, as shown in CN1302031 C
However, the problem with using excess maleic anhydride is that once all the alkyl methacrylate monomer is consumed, polymer chain growth is prevented, and such methods require additional purification steps to remove unreacted maleic anhydride. Anhydride

Method used

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  • Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride
  • Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride
  • Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride

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Embodiment 1

[0053] Various copolymers of alkyl methacrylate and maleic anhydride were prepared using the process of the invention and using different alkyl methacrylates and different comonomer molar ratios according to the following general procedure.

[0054]The solvent (MIBK), maleic anhydride, and a portion of the free radical initiator (tert-butyl peroxy-2-ethylhexanoate) were added to the reaction vessel. The mixture was heated to a temperature of 90°C to dissolve the reactants. While stirring, a further portion of the feed solution of alkyl methacrylate and free radical initiator in MIBK was added to the reaction vessel over a period of 6 hours. Based on the total mass of the monomer and the solvent, the total amount of MIBK is 12.5% ​​by weight. Two hours after the feed solution had been added completely, an additional dose of initiator was added. The copolymerization mixture was stirred overnight before the reaction was stopped. The copolymerization mixture was then diluted wi...

Embodiment 2

[0073] Embodiment 2 (comparative example)

[0074] The following examples illustrate the method of solution polymerization according to US 5721201 A.

[0075] A solution of maleic anhydride in toluene was fed into the reaction vessel and heated to a reaction temperature of 80°C. When the maleic anhydride had dissolved, the free radical initiator (AIBN) in toluene was introduced into the reaction vessel. A solution of alkyl methacrylate or alkyl acrylate was added to the reaction vessel over a period of 4 hours.

[0076] Using this general procedure, Examples 1, 2 and 3 of US 5721201 A were reproduced to prepare eight different copolymers.

[0077] Copolymer 1 was prepared from 72.7% by weight DPMA and 27.3% by weight MSA, based on the total amount of monomers.

[0078] Copolymer 2 was prepared from 73.1% by weight DPA and 26.9% by weight MSA based on the total amount of monomers.

[0079] Copolymer 3 was prepared from 73.7% by weight DPMA and 26.3% by weight MSA based on t...

Embodiment 3

[0092] Embodiment 3 (comparative example)

[0093] In the following comparative example, a copolymer of methacrylate and maleic anhydride was prepared under the reaction conditions of the solution copolymerization method disclosed in CN 1302031 C.

[0094] A mixture of maleic anhydride in toluene was added to the reaction vessel and heated to a reaction temperature of 60°C. The reaction mixture was flushed with nitrogen for 30 minutes. When the maleic anhydride was completely dissolved, the alkyl methacrylate was added and the reaction was initiated by adding a free radical initiator. Instead of AIBN, the radical initiator 2,2'-azobis-(2-methylbutyronitrile) (AMBN) was used. Both initiators are azo compounds with similar half-lives.

[0095] Two different copolymers were prepared. Copolymer 1 was prepared from 53.3 wt. % LMA, 21.7 wt. % SMA and 26 wt. % MSA based on the total amount of monomers. Copolymer 2 was prepared from 56.9% by weight SMA, 21.1% by weight BeMA and 22%...

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Abstract

The present invention relates to a method for the preparation of a copolymer comprising at least one alkyl methacrylate and maleic anhydride having a number average molecular weight of 4000 to 18000 g / mol by solution polymerization in the presence of a radical initiator.

Description

technical field [0001] The invention relates to a process for the preparation of copolymers of alkyl methacrylates and maleic anhydride having a number-average molecular weight of 4000 to 18000 g / mol by solution polymerization in the presence of free-radical initiators. Background technique [0002] Alkyl (meth)acrylate / maleic anhydride copolymers are known to function as so-called flow improvers for hydrocarbon oils such as gas oil, diesel oil, fuel oil, lubricating oil and crude oil. These oils contain a large proportion of long chain n-paraffins which crystallize when cooled and lead to increased oil viscosity and reduced oil fluidity at low temperatures. Alkyl (meth)acrylate / maleic anhydride copolymers can inhibit the crystallization of long-chain n-paraffins and can thus improve the flow properties of hydrocarbon oils at low temperatures. [0003] Alkyl (meth)acrylate / maleic anhydride copolymers can be prepared by solution polymerization in the presence of free radical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/18C08F2/00C08F2/06
CPCC08F2/001C08F2/06C08F220/1818C08F220/1811C08F220/1812C08F222/06C10M145/16C10L1/1966C10L10/14C10M2209/086C10N2020/04C10N2030/02C10N2070/00C10M2209/084
Inventor R·格克哈尔S·姆林M·K·施蒂许尔卡K·施莫瑟克F-O·梅林
Owner EVONIK OPERATIONS GMBH
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