Process for stabilizing phenolic resins containing calixarenes

1. A process for stabilizing a phenolic resin containing a mixture of linear phenolic resins and calixarenes, comprising:

contacting, in a one-step process, 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, in a one-step process, 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, in a one-step process, 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% resin by weight.