Preparation and use of cyclododecatriene trialdehyde and related compounds

Patent metadata

Field	Value
Publication number	US-9598339-B2
Application number	US-201615078655-A
Country	US
Kind code	B2
Filing date	Mar 23, 2016
Priority date	Feb 24, 2012
Publication date	Mar 21, 2017
Grant date	Mar 21, 2017

Abstract

Disclosed herein are compositions and methods related to the hydroformylation of cyclododecatriene to form cyclododecatriene trialdehyde, and the conversion of the trialdehyde to the polyphenols of Formula 1:

where R, m p and Q are as defined herein. Curable compositions comprising compounds of Formula 1, including powder coating compositions, and methods of curing the compositions are also disclosed.

First claim

What is claimed is:

1. Methods of making compounds of the formula:

wherein each m independently has a value of 1 to 3,
p has a value of zero to 20;
each R is independently halogen, nitrile, nitro; C 1 -C 6 alkyl or C 1 -C 6 alkoxy, wherein the alkyl and alkoxy groups are optionally substituted with one or more halogen atoms, C 2 -C 6 alkenyl or C 2 -C 6 alkenyloxy groups; and each Q is independently hydrogen or C 1 -C 6 alkyl; or the R group may be a C 3 -C 4 alkylene group that optionally contains one or two double bonds and is bonded to two adjacent carbons on the ring to which it is attached;
the methods comprising
subjecting the trialdehyde of cyclododecane to conditions sufficient to convert the aldehyde groups to the diphenolmethyl groups.

2. Methods according to claim 1 , wherein the trialdehyde is reacted with an optionally substituted phenol in the presence of a catalyst.

3. Methods according to claim 1 , wherein the conditions comprise a reaction temperature of 50° C. to 80° C. and a reaction time of 10 hours to 24 hours and the catalyst is acidic.

4. Methods according to claim 2 , wherein the catalyst is 3-mercapto-1-propane sulfonic acid.

Assignees

• Dow Global Technologies Llc

Inventors

• Molitor Erich J
• Hefner Jr Robert E

Classifications

• C07C39/17

  containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol} · CPC title

• C07C2601/20

  the ring being twelve-membered · CPC title

• C09D161/06

  of aldehydes with phenols · CPC title

• C08L61/06

  of aldehydes with phenols · CPC title

• C07C37/20 Primary

  using aldehydes or ketones · CPC title