Process for stabilizing phenolic resins containing calixarenes

Patent metadata

Field	Value
Publication number	US-2016108231-A1
Application number	US-201514919509-A
Country	US
Kind code	A1
Filing date	Oct 21, 2015
Priority date	Oct 21, 2014
Publication date	Apr 21, 2016
Grant date	—

Abstract

This invention relates to a process for stabilizing a phenolic resin containing a mixture of linear phenolic resins and calixarenes and a demulsifier composition comprising the stabilized phenolic resins prepared from the process. The process comprises contacting the phenolic resin with an alkylene carbonate, in the presence of a base catalyst, to at least partially alkoxylate the phenolic hydroxyl groups of the calixarenes. This process forms a stabilized phenolic resin with an increased solubility in a hydrocarbon solvent.

First claim

We claim:

1 . A process for stabilizing a phenolic resin containing a mixture of linear phenolic resins and calixarenes, comprising:
contacting the phenolic resin with an alkylene carbonate, in the presence of a base catalyst, to at least partially alkoxylate the phenolic hydroxyl groups of the calixarenes, thereby forming a stabilized phenolic resin mixture, wherein about 0.2 to 1 mole of alkylene carbonate reacts with the phenolic hydroxyl groups for each mole of the phenolic resin.

2 . The process of claim 1 , wherein the phenolic hydroxyl groups of the linear phenolic resins are also at least partially alkoxylated.

3 . The process of claim 1 , wherein the base catalyst is potassium carbonate.

4 . The process of claim 1 , wherein the alkylene carbonate is propylene carbonate, ethylene carbonate, or butylene carbonate.

5 . The process of claim 4 , wherein the alkylene carbonate is propylene carbonate.

6 . The process of claim 1 , wherein the benzene ring of the linear phenolic resins and calixarenes is independently substituted by H, C 1 to C 30 alkyl, phenyl, or arylalkyl.

7 . The process of claim 1 , wherein the linear phenolic resins and calixarenes independently contain a C 1 to C 7 alkyl substituent on the benzene ring.

8 . The process of claim 1 , further comprising:
reacting one or more phenolic compound with an aldehyde, in the presence of a base catalyst, to form the phenolic resin containing a mixture of linear phenolic resins and calixarenes.

9 . The process of claim 8 , wherein the benzene ring of the phenolic compound is substituted by H, C 1 to C 30 alkyl, phenyl, or arylalkyl.

10 . The process of claim 8 , wherein at least one phenolic compound has a C 1 to C 7 alkyl substituent on the benzene ring.

11 . The process of claim 1 , wherein the phenolic resin contains about 20% to about 75% calixarenes.

12 . A process for stabilizing a phenolic resin containing a mixture of linear phenolic resins and calixarenes, comprising:
contacting the phenolic resin with an alkylene carbonate, in the presence of a base catalyst and a hydrocarbon solvent, to at least partially alkoxylate the phenolic hydroxyl groups of the calixarenes, thereby forming a stabilized phenolic resin mixture, wherein less than 10% of the calixarenes precipitate out of the solvent after 24 hours.

13 . The process of claim 12 , wherein less than 5% of the calixarenes precipitate out of the solvent after 24 hours.

14 . The process of claim 12 , wherein the formed stabilized phenolic resin mixture is substantially free of undissolved solid components, without adding additional solvents.

15 . The process of claim 12 , wherein the hydrocarbon solvent is an aromatic hydrocarbon.

16 . A process for increasing the solubility of a linear phenolic resin/calixarene mixture, comprising:
contacting a phenolic resin containing a mixture of linear phenolic resins and calixarenes with an alkylene carbonate, in the presence of a base catalyst, to at least partially alkoxylate the phenolic hydroxyl groups of the calixarenes, wherein the solubility of the linear phenolic resin/calixarene mixture in a hydrocarbon solvent is increased by at least 50%.

17 . The process of claim 16 , wherein the solubility of the linear phenolic resin/calixarene in a hydrocarbon solvent is increased by at least 60%.

18 . The process of claim 16 , wherein the hydrocarbon solvent is an aromatic hydrocarbon.

19 . A demulsifier composition comprising the stabilized phenolic resin mixture prepared by the process of claim 1 .

20 . The demulsifier composition of claim 19 , wherein the stabilized phenolic resin mixture is a resin solution having a concentration of 50% to 75% by weight.

Assignees

• Si Group Inc

Inventors

• Aube Todd
• Barbiero Gennaro
• Biittig Ricky
• Baxter Jr James M

Classifications

• C08L2205/025

  containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure · CPC title

• C08L65/02 Primary

  Polyphenylenes · CPC title

• C08G8/28

  Chemically modified polycondensates · CPC title

• C08L61/14 Primary

  Modified phenol-aldehyde condensates · CPC title

• C08G8/36 Primary

  by etherifying · CPC title