Solubilized alkoxylated calixarene resins

Patent metadata

Field	Value
Publication number	US-10875953-B2
Application number	US-201815879270-A
Country	US
Kind code	B2
Filing date	Jan 24, 2018
Priority date	Jan 25, 2017
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

Abstract

This invention relates to an alkoxylated calixarene resin comprising one or more modified calixarene alkoxylate compounds. The invention also relates to a process for preparing a solubilized alkoxylated calixarene resin comprising reacting a phenolic resin mixture, comprising linear phenolic resins and calixarene compounds having phenolic hydroxyl groups, with one or more epoxide-containing compounds to alkoxylate one or more of the phenolic hydroxyl groups of the calixarene compounds to form a solubilized phenolic resin mixture, and reacting the solubilized phenolic resin mixture with one or more alkylene oxides.

First claim

We claim:

1. An alkoxylated calixarene resin comprising one or more modified calixarene alkoxylate compounds, each modified calixarene alkoxylate compound comprising 4-20 units of formula (IV), (V), and/or formula (VI):

wherein:
each X is independently the same or different moiety, each moiety having a structure of

each Z is independently the same or different moiety, each moiety having a structure of

each R′ and R″ are independently H, or C 1 to C 4 alkyl;
each R 1 is independently a H, C 1 to C 30 alkyl, phenyl, or arylalkyl;
each R 2 is independently a H, C 1 to C 20 branched or unbranched alkyl which may optionally be substituted with one or more glycidyl ether units of the formula

C 2 to C 10 alkenyl, or C 5 to C 10 aryl;
each L is independently selected from the group consisting of —CH 2 —, —C(O)—, —CH(R 3 )—, —(CH 2 ) n —O—(CH 2 ) n —, —C(R 3 ) 2 —, and —S—;
each R 3 is independently a C 1 -C 6 alkyl;
each m is independently an integer from 0 to 10; provided that when m is 0, each R 2 is independently a C 5 to C 10 aryl;
each n is independently an integer from 1 to 2;
each p is independently an integer from 1 to 150;
each q is independently an integer from 1 to 100; and
each A 1 represents a direct covalent bond to an adjacent unit of formula (IV), (V), or formula (VI) such that there is one L group between adjacent units, whereby the total units in the modified calixarene alkoxylate compound form a ring; and
wherein the units of formula (IV) make up from about 35% to 100% of the overall units present in the modified calixarene alkoxylate compounds.

2. The alkoxylated calixarene resin of claim 1 , wherein each m is 1.

3. The alkoxylated calixarene resin of claim 2 , wherein each R 2 is independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, allyl, ethylhexyl, octyl, nonyl, decyl, phenyl, nonylphenyl, and hexadecyl; or is independently a C 1 to C 8 branched or unbranched alkyl, substituted with one or more glycidyl ether units of the formula

4. The alkoxylated calixarene resin of claim 3 , wherein each R 2 is n-butyl or

5. The alkoxylated calixarene resin of claim 1 , wherein each Z is

or a combination thereof.

6. The alkoxylated calixarene resin of claim 1 , wherein each p is independently 1-20.

7. The alkoxylated calixarene resin of claim 1 , wherein each R 1 is independently a C 4 to C 12 alkyl or C 24 to C 28 alkyl.

8. The alkoxylated calixarene resin of claim 1 , wherein the total number of units in the calixarene compounds is from 4 to 8.

9. The alkoxylated calixarene resin of claim 1 , wherein one or more units in the modified calixarene alkoxylate compounds have the structure of

wherein:
each R 1 is independently a C 4 to C 12 alkyl;
each Z is

or a combination thereof;
each p is independently 1-20;
each L is independently —CH 2 —or —CH 2 —O—CH 2 —; and
the total units in the calixarene compounds is from 4 to 8.

10. The alkoxylated calixarene resin of claim 1 , wherein the alkoxylated calixarene resin has a solubility in a hydrocarbon solvent increased by at least 20% compared to a resin comprising calixarene compounds containing units of formula (V) and/or (VI), but no units of formula (IV).

11. A resin solution comprising the alkoxylated calixarene resin of claim 1 , wherein the alkoxylated calixarene resin is dissolved in a hydrocarbon solvent having a concentration of about 50 wt % to about 75 wt %.

12. The resin solution of claim 11 , wherein the hydrocarbon solvent is an aromatic hydrocarbon solvent selected from the group consisting of toluene, xylene, tetralin, a C 9 -C 10 aromatic hydrocarbon solvent, and a C 10 -C 12 aromatic hydrocarbon solvent.

13. A method of resolving a water-in-oil or oil-in-water emulsion, comprising:
adding to a water-in-oil or oil-in-water emulsion an effective demulsifying amount of one or more alkoxylated calixarene resins of claim 1 .

Assignees

• Si Group Inc

Inventors

• Meketa Matthew
• Haase Cornelius
• Cable Robert
• Biittig Ricky
• Staats Allyson

Classifications

• B01D17/047

  with separation aids · CPC title

• C08G8/36 Primary

  by etherifying · CPC title

• C10G2300/1033

  Oil well production fluids · CPC title

• C08G8/12

  with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol · CPC title

• C10G33/04

  with chemical means · CPC title