Pentyl nonyl terephthalates

Patent metadata

Field	Value
Publication number	US-2016237243-A1
Application number	US-201615046242-A
Country	US
Kind code	A1
Filing date	Feb 17, 2016
Priority date	Feb 18, 2015
Publication date	Aug 18, 2016
Grant date	—

Abstract

Mixtures containing dipentyl terephthalate, dinonyl terephthalate and pentyl nonyl terephthalate can be prepared with a predetermined distribution of the individual esters in the mixture, and used as plasticizers.

First claim

1 . A mixture, comprising:
a terephthalic diester of each of the formulae I, II and III,

wherein
R 1 is an alkyl radical having 5 carbon atoms, and
R 2 is an alkyl radical having 9 carbon atoms.

2 . The mixture according to claim 1 , wherein in the formulae I, II and III, R 1 is selected from the group consisting of 2-methylbutyl, 3-methylbutyl, n-pentyl and isopentyl radicals and R 2 is selected from the group consisting of nonyl, n-nonyl and isononyl radicals.

3 . The mixture according to claim 1 , which comprises less than 80 mol % of the ester of formula II, based on the entirety of the esters I, II and III.

4 . The mixture according to claim 1 , which comprises less than 70 mol % of the ester of formula III, based on the entirety of the esters I, II and III.

5 . The mixture according to claim 1 , which comprises less than 60 mol % of the ester of formula III, based on the entirety of the esters I, II and III.

6 . The mixture according to claim 1 , which comprises less than 60 mol % of the ester of formula I, based on the entirety of the esters I, II and III.

7 . The mixture according to claim 1 , which comprises less than 50 mol % of the ester of formula I, based on the entirety of the esters I, II and III.

8 . The mixture according to claim 1 , which comprises less than 40 mol % of the ester of formula I, based on the entirety of the esters I, II and III.

9 . A polymer plasticizer, comprising:
the mixture according to claim 1 .

10 . The polymer plasticizer according to claim 9 , wherein said polymer is PVC.

11 . An adhesive, sealant, coating material, paint, ink, plastisol, foam, synthetic leather, floorcovering, roofing membrane, underbody protection, fabric coating, cable, wire insulation, hose, extruded article, film, automotive interior article, wallcovering, liquid ink, toy, contact sheet, food packaging or medical article, comprising:
the polymer plasticizer according to claim 9 .

12 . A composition, comprising:
a mixture according to claim 1 ; and one or more polymers selected from the group consisting of polyvinyl chloride, copolymers of vinyl chloride with vinyl acetate or with butyl acrylate, polyalkyl methacrylate (PAMA), polyvinyl butyral (PVB), polyurethane, polysulphides, polylactic acid (PLA), polyhydroxybutyral (PHB) and nitrocellulose.

13 . A process for preparing an ester mixture according to claim 1 , said process comprising:
esterifying terephthalic acid or a terephthalic acid derivative with a mixture comprising R 1 OH (R 1 =alkyl radical having 5 carbon atoms) and R 2 OH (R 2 =alkyl radical having 9 carbon atoms).

14 . A process for preparing an ester mixture according to claim 1 , said process comprising:
reacting the ester of formula I with less than 1 mole equivalent, based on the number of ester functions in the ester of formula I, of an alcohol or of two or more alcohols having 9 carbon atoms in a reaction mixture, while heating said reaction mixture.

15 . The process according to claim 14 , wherein the ester of formula I is reacted with an alcohol or with two or more alcohols having 9 carbon atoms in the presence of a catalyst;
wherein said reaction mixture is heated to boiling; wherein more than 80 mol % of a C 5 alcohol which forms in the course of the process is removed from the reaction vessel during the process.

16 . A process for preparing an ester mixture according to claim 1 , said process comprising:
reacting terephthalic acid with a derivative of terephthalic acid which contains no ester group COOR with a radical R whose alcohol ROH has a higher boiling point at a defined pressure than the alcohol R 1 OH of the radical R 1 at the same pressure, with an amount (m 1 +s 1 ) of R 1 OH and an amount m 2 of R 2 OH, the reaction mixture being heated at boiling, wherein m 1 and m 2 correspond to the mole equivalents of the alcohol radical OR 1 (C 5 alcohol radical) and OR 2 (C 9 alcohol radical) to be introduced into terephthalic acid or derivatives thereof, and s 1 is greater than 0.

17 . The process according to claim 16 , wherein the amount s 1 is less than (m 1 +m 2 ), and at the same time greater than 0.05·(m 1 +m 2 ).

18 . The process according to claim 16 , wherein at least 0.8 mole equivalents of alcohol R 2 OH used is introduced as OR 2 radical into the terephthalic acid or derivative thereof;
and/or wherein, in the process, a catalyst is used, and in the reaction mixture, the amount of C 5 alcohol has been lowered to less than 20 mol %, based on the excess amount s 1 of the C 5 alcohol, before the catalyst is destroyed.

19 . Process according to claim 16 , wherein R 1 is 2-methylbutyl, 3-methylbutyl, n-pentyl and/or isopentyl radicals and R 2 is an isononyl radical, the mixture comprising less than 80 mol % of the ester of formula II, based on the entirety of the esters I, II and II.

20 . The process according to claim 13 , comprising:
controlling the quantitative distribution of the esters in the ester mixture in order to set processing-relevant and/or application-relevant properties of the resulting ester mixture.

Assignees

• Woldt Benjamin
• Boeck Florian Sebastian
• Grass Michael
• Haeger Harald
• Evonik Degussa Gmbh

Inventors

• Woldt Benjamin
• Boeck Florian Sebastian
• Grass Michael
• Haeger Harald

Classifications

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C67/03

  by reacting an ester group with a hydroxy group · CPC title

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title

• C07C69/82 Primary

  Terephthalic acid esters · CPC title

• C08K5/101

  of monocarboxylic acids · CPC title