Antioxidants for producing low-emission pur systems

Patent metadata

Field	Value
Publication number	US-2016264757-A1
Application number	US-201615016503-A
Country	US
Kind code	A1
Filing date	Feb 5, 2016
Priority date	Mar 10, 2015
Publication date	Sep 15, 2016
Grant date	—

Abstract

A compound of the formula (I)

in which
R is CH 2 —CH(R I ), CH(R II )—CH(R II ), CH 2 —C(R II ) 2 , C(R II ) 2 —C(R II ) 2 ,

CH 2 —CH—CH 2 —R IV , C 6 H 6 —CH—CH 2 , C 6 H 6 —C(CH 3 )—CH 2 , where

R I is C 2 to C 24 alkyl radical or alkene radical,
R II is C 2 to C 24 alkyl radical or alkene radical,
R III is C 3 to C 6 alkyl radical, which is arranged linearly, and
R IV is OH, Cl, OCH 3 , OCH 2 —CH 3 , O—CH 2 —CH═CH 2 , O—CH═CH 2 molecule residue of epoxidized fats or oils,
R 1 and R 2 independently of one another are C 1 -C 8 alkyl, cyclopentyl or cyclohexyl, especially tert-butyl,
R 3 is an n-valent radical of C 1 -C 30 -alkyl,
R 4 is hydrogen, an n-valent radical of C 1 -C 30 alkyl, which is optionally interrupted by one or more groups —NR 5 — or (where n=1-12) is an n-valent radical of C 5 -C 12 cycloalkyl,
R 5 independently at each occurrence is hydrogen or methyl or —C q H 2q .

First claim

What is claimed is:

1 . A compound of the formula (I)

in which
R is CH 2 —CH(R I ), CH(R II )—CH(R II ), CH 2 —C(R II ) 2 , C(R II ) 2 —C(R II ) 2 ,

CH 2 —CH—CH 2 —R IV , C 6 H 6 —CH—CH 2 , or C 6 H 6 —C(CH 3 )—CH 2 , where

R I is C 2 to C 24 alkyl radical or alkene radical, which may be linear or branched
R II is C 2 to C 24 alkyl radical or alkene radical, which may be linear or branched
R III is C 3 to C 6 alkyl radical, which is arranged linearly, and
R IV is OH, Cl, OCH 3 , OCH 2 —CH 3 , O—CH 2 —CH═CH 2 , O—CH═CH 2 , molecule residue of singly or multiply epoxidized fats or oils as mono-, di-, and triglycerides, or molecule residue of singly or multiply epoxidized fatty acids or their C 1 -C 24 alkyl esters,
R 1 and R 2 independently of one another are straight-chain or branched C 1 -C 8 alkyl, cyclopentyl or cyclohexyl, especially tert-butyl,
q is 1, 2 or 3,
n is an integer from 1 to 30,
R 3 is an n-valent radical of linear or branched C 1 -C 30 -alkyl, interrupted in each case optionally by one or more oxygen atoms, or (especially where n=1-12) is an n-valent radical of C 5 -C 12 cycloalkyl, or a radical R 4 [NR 5 —C q H 2q —] p ,
R 4 is hydrogen, an n-valent radical of linear or branched C 1 -C 30 alkyl, which is optionally interrupted by one or more groups —NR 5 — or (where n=1-12) is an n-valent radical of C 5 -C 12 cycloalkyl,
R 5 independently at each occurrence is hydrogen or methyl or —C q H 2q , and
p corresponds to the number of —[NR 5 —C q H 2q —] groups that produces n radicals —C q H 2q — per molecule,
k is an integer between 0 and 50,
m is an integer between 0 and 50, and
o is an integer between 0 and 50,
where (k+m+o)>10.

2 . An antioxidant mixture comprising at least one compound of the formula (I) and a further antioxidant.

3 . An antioxidant mixture according to claim 2 , comprising as further antioxidant:
at least one benzofuranone derivative of the formula (II)

in which
n is an integer between 0 and 7,
R 6 and R 7 independently of one another are H or C 1 -C 8 alkyl,

R 8 is H or an aromatic radical where
R 9 and R 10 independently of one another are H or C 1 -C 6 alkyl, with not both being a C 1 -C 6 alkyl,
R 11 and R 12 independently of one another are H or C 1 -C 6 alkyl, with not both being a C 1 -C 6 alkyl,
R 13 is H or OH.

4 . The antioxidant mixture according to claim 3 , characterized in that the compound of the formula (I) is present in an amount of 75 to 99 wt % and the compound of the formula (II) is present in an amount of 1 to 25 wt %, wt % being based on the total weight of the compounds of the formulae (I) and (II) used.

5 . The antioxidant mixture according to claim 3 , further comprising a phosphite of the formula (III),

in which
R 14 , R 15 and R 16 independently of one another are an aromatic or aliphatic, linear or branched radical of C 1 -C 30 alkyl or C 2 -C 30 alkylene, interrupted in each case optionally by one or more oxygen atoms,
the phosphite being present preferably in amounts of 0.1 to 20 wt %, wt % being based on the total weight of the compounds of the formulae (I), (II) and phosphite used.

6 . A process for producing polyurethane systems by reaction of at least one polyol component with at least one isocyanate component in the presence of one or more catalysts which catalyse the isocyanate-polyol and/or isocyanate-water reactions and/or the isocyanate trimerization, characterized in that the reaction is carried out in the presence of one or more compounds of the formula (I) or in the presence of an antioxidant mixture according to claim 3 .

Assignees

• Evonik Degussa Gmbh

Inventors

• Krebs Michael
• Hubel Roland

Classifications

• C08G18/244

  tin salts of carboxylic acids · CPC title

• C08K5/1535

  Five-membered rings · CPC title

• C08K5/526

  with hydroxyaryl compounds · CPC title

• C08J9/0023

  containing oxygen · CPC title

• C08G65/3326 Primary

  aromatic · CPC title