Granted Patent B2

US 10,875,953 · App. 15/879,270 · Granted Dec 29, 2020

Abstract

Claims (37)

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 .

Assignments (7)