Citrate-based plasticizer and resin composition containing same

A technology of citric acid esters and resin compositions, applied in the direction of organic chemistry, can solve the problems of complex preparation process and difficult commercialization, and achieve the effects of excellent physical properties, excellent plasticizing efficiency, and excellent quality reproducibility

Active Publication Date: 2019-12-03
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In addition, citrate esters having alkyl groups with different carbon numbers can be used as a single plasticizer, but in this case, the preparation process is complicated, and it is difficult to commercialize due to economical reasons according to the increase in production cost

Method used

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  • Citrate-based plasticizer and resin composition containing same
  • Citrate-based plasticizer and resin composition containing same
  • Citrate-based plasticizer and resin composition containing same

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preparation example Construction

[0052] The preparation method of citrate plasticizer

[0053] According to one embodiment of the present invention, the citrate plasticizer may be obtained by direct esterification of citric acid and alcohol, or by transesterification of a compound represented by Formula 1 below with alcohol.

[0054] [Formula 1]

[0055]

[0056] In formula 1, R 1 to R 3 each independently is an alkyl group having 7 carbon atoms.

[0057] More specifically, in the case of preparing a citrate-based plasticizer comprising a compound of formula 1-1 or formula 1-2, direct esterification reaction can be applied, and can be carried out using citric acid and n-heptanol or 2-methanol The direct esterification reaction of hexanol. In other words, as a preparation method of non-mixed citrate, direct esterification reaction can be carried out, and in the case of preparing citrate plasticizers containing compounds of formula 1-1 and formula 1-2, separate preparation of and a way to mix them.

...

preparation Embodiment 1

[0091] Preparation Example 1: Preparation of Tris(n-heptyl) Citrate (THC)

[0092]Into a 3-liter four-neck reactor equipped with a cooler, water stripper, condenser, decanter, reflux pump, temperature controller and stirrer was charged 576 g of isolated 2-hydroxypropane-1,2,3 -tricarboxylic acid (citric acid), 1,566 g of n-heptanol (Aldrich) (molar ratio 1:4.5) and 1.44 g (0.25 parts by weight based on 100 parts by weight of citric acid) of titanium-based catalyst (TnBT , tetra-n-butyl titanate), and then slowly increase the temperature to about 170°C. At about 170°C, water started to be generated, and the esterification reaction was carried out for about 4.5 hours at a reaction temperature of about 220°C under atmospheric pressure while continuously feeding nitrogen. When the acid value reaches 0.1, the reaction ends.

[0093] After the reaction is over, distillation extraction is performed under reduced pressure for 0.5 hours to 4 hours to remove unreacted raw materials, t...

preparation Embodiment 2

[0094] Preparation Example 2: Preparation of Tris(2-methylhexyl) Citrate (TiHC)

[0095] Except that 2-methylhexanol was used instead of n-heptanol in Preparation Example 1, the same reaction method as in Preparation Example 1 was carried out to finally obtain 1,435 g (yield: 98%) of tris(2- Methylhexyl) ester (TiHC).

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Abstract

The present invention relates to a citrate-based plasticizer and a resin composition containing the same, wherein the citrate-based plasticizer comprises at least one citrate having an alkyl group having seven carbon atoms. The citrate-based plasticizer can solve problems of migration and heating loss, which are involved in an existing plasticizer, or problems due to process characteristics, suchas plasticizing efficiency and an absorption rate, and can achieve excellent reproducibility of product quality.

Description

technical field [0001] [Cross Reference to Related Application] [0002] This application claims priority and benefits based on Korean Patent Application No. 10-2017-0064749 filed on May 25, 2017, the entire contents of which are incorporated herein by reference. [technical field] [0003] The invention relates to a citrate plasticizer and a resin composition containing it. Background technique [0004] Typically, as plasticizers, alcohols react with polycarboxylic acids such as phthalic acid and adipic acid to form the corresponding esters. Commercially important examples include adipate esters of C8, C9 and C10 alcohols, for example, bis(2-ethylhexyl) adipate, diisononyl adipate and diisodecyl adipate; and C8 , phthalates of C9 and C10 alcohols, for example, bis(2-ethylhexyl) phthalate, diisononyl phthalate and diisodecyl phthalate. [0005] Specifically, bis(2-ethylhexyl)phthalate is used by plastisols and dry mixing for the manufacture of toys, films, shoes, paints,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/101C08L101/00C08K5/00
CPCC08K5/11C08K5/0016C08K2201/014C07C69/704C08L27/06C08K5/101C08L101/00
Inventor 金显圭赵允基金宙镐文正周
Owner LG CHEM LTD
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