Method for the preparation of polyesters

Patent metadata

Field	Value
Publication number	US-9464164-B2
Application number	US-201013259163-A
Country	US
Kind code	B2
Filing date	Mar 18, 2010
Priority date	Mar 26, 2009
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

Disclosed is a method for preparing polyesters, comprising
reacting polyols with carboxylic acids and, optionally, a catalyst, wherein the polyols bear at least two hydroxyl groups, wherein, at least one of said hydroxyl group is bound to an aliphatic carbon atom and wherein the polyols comprise one or more compounds of the formula (I) or (II),

 where
 n is 1, 2, 3 or 4,
 m is 1, 2 or 3,
 p is 2,
 Q is sulphur or C 1 -C 4 -alkylene, and
 the radicals R 1 are each, independently of any other radicals R 1 present, C 1 -C 8 -alkyl or C i -C 8 -alkoxy,

where at least one ortho position of the two phenyl rings in the formula (II) or the phenyl ring in the formula (I) must be substituted by a secondary or tertiary radical.

First claim

What is claimed is:

1. A method for preparing polyester from stabilized polyols and polycarboxylic acid, the method comprising:
stabilizing one or more polyols selected from a group consisting of 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, octane-1,8-diol, decane-1,10-diol, trimethylolpropane, ditrimethyiolpropane, pentaerythritol, neopentyl glycol, ethylene glycol, diethylene triethylene glycol, tetraethylene glycol, 1,3-butylene glycol and 1,4-cyclohexanediol or mixtures thereof, by contacting the polyols with one or more compounds of the formula (I) or (Il) to produce a first mixture containing stabilized polyols,

where:
n is 1, 2, 3 or 4,
m is 1, 2 or 3,
p is 2,
Q is sulphur or methylene, and

the radicals R 1 are each, independently of any other radicals R 1 present, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy,
where at least one ortho position of the two phenyl rings in the formula (II) or the phenyl ring in the formula (I) must be substituted by a secondary or tertiary radical; and

subsequent to producing the first mixture of stabilized polyols, contacting one or more polycarboxylic adds with the first mixture of stabilized polyols to form a second mixture and produce polyesters from the stabilized polyols and the polycarboxylic acid.

2. Method according to claim 1 , wherein the one or more compounds of formula (I) or (II) comprise 2,6-bis[tert-butyl]-4-methylphenol] (BHT), 2,4,6-tri-t-butylphenol, 2- and 3-tert-butylhydroxyanisole and mixtures thereof (BHA), 2,2′-methylenebis[4-metnyl-6-(α-methylcyclohexyl)phenol], 2,2′-methylenebis[4-methyl -6-cyclohexyl)phenol] (ZKF), 2,2′-methylenebis(4-methyl-6-tert-butylphenol), 2,2′-methylenebis[6-tert-butyl-4-ethylphenel], 2,2′-methylenebis[6-tert-butyl-4-methyl -phenol] (BKF), 4,4′-methylenebis[2,6-di-tert-butylphenol], 4,4′-methylenebis[6-tert-butyl -2-methylphenol] or mixtures thereof.

3. The method according to claim 1 , wherein the polycarboxylic acid is adipic acid.

4. The method of claim 1 , wherein, based on the weight of the first mixture, the first mixture comprises:
at least 40 wt % of the one or more polyols: and
0.001 to 60 wt % of the one or more compounds of formula (I) or formula (II).

5. A method for preparing polyester from polycarboxylic acid and stabilized polyols, the method comprising:
contacting one or more aliphatic polyols with one or more compounds of the formula (I) or (II)

where:
n is 1, 2, 3 or 4,
m is 1, 2 or 3,
p is 2,
Q is sulphur or C 1 -C 4 alkylene,

the radicals R 1 are each, independently of any other radicals R 1 present, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy, and
where at least one ortho position of the two phenyl rings in the formula (II) or the phenyl ring in the formula (I) must be substituted by a secondary or tertiary radical,

 to stabilise the one or more polyols and produce stabilized polyols;
contacting arm or more poiycarboxylic acids and the stabilized polyols produce a reaction mixture, and esterifying the polycarboxylic acids and stabilized polyols to produce polyesters.

Assignees

• Heuer Lutz
• Lanxess Deutschland Gmbh

Inventors

• Heuer Lutz

Classifications

• C08G63/78

  Preparation processes · CPC title

• C07C29/94 Primary

  Use of additives, e.g. for stabilisation · CPC title

• C08G63/12 Primary

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• C08G63/20

  Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups · CPC title

• C07C35/14

  with more than one hydroxy group bound to the ring · CPC title