Granted Patent B2

US 10,889,677 · App. 15/879,245 · Granted Jan 12, 2021

Abstract

Claims (45)

1. A resin solution of a phenolic resin, comprising one or more modified calixarene compounds, each calixarene compound comprising 4-20 units of formula (I′) and/or formula (II):

wherein:

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

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 q is independently an integer from 1 to 100;

each A 1 represents a direct covalent bond to an adjacent unit of formula (I′) or formula (II) such that there is one L group between adjacent units, whereby the total units in the calixarene compound form a ring; and

wherein units of formula (I′) make up from about 35% to 100% of the overall units present in the calixarene compound, and

wherein the phenolic resin is soluble in a hydrocarbon solvent having a concentration of about 50 wt % to about 75 wt %.

2. The resin solution of claim 1 , wherein each m is 0 or 1.

3. The resin solution 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 20 branched or unbranched alkyl substituted with one or more glycidyl ether units of the formula

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

5. The resin solution of claim 2 , wherein each R 1 is independently a C 4 to C 12 alkyl or C 24 to C 28 alkyl.

6. The resin solution of claim 2 , wherein the total number of units in the calixarene compounds is from 4 to 8.

7. The resin solution of claim 1 , wherein q is 1 in one or more units in the modified calixarene compounds.

8. The resin solution of claim 1 , wherein the one or more modified calixarene compounds have one or more units of formula (I′) represented by the structure of

wherein:

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

each L is independently selected from the group consisting of —CH 2 —, —C(O)—, —CH(R 3 )—, —(CH 2 ) n —O—(CH 2 ) n —, and —C(R 3 ) 2 —;

each R 3 is independently a C 1 -C 6 alkyl;

each n is independently an integer from 1 to 2; and

the total number of units in the calixarene compounds is from 4 to 8.

9. The resin solution of claim 8 , wherein each R 1 is independently tert-butyl, nonyl, or tert-octyl.

10. The resin solution of claim 1 , 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.

11. A resin with an increased solubility in a hydrocarbon solvent, comprising one or more modified calixarene compounds, each calixarene compound comprising 4-20 units of formula (I′) and/or formula (II):

wherein:

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

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 q is independently an integer from 1 to 100;

each A 1 represents a direct covalent bond to an adjacent unit of formula (I′) or formula (II) such that there is one L group between adjacent units, whereby the total units in the calixarene compound form a ring; and

wherein units of formula (I′) make up from about 35% to 100% of the overall units present in the calixarene compound, and

wherein the solubility of the resin is increased by at least 20% compared to a resin comprising calixarene compounds containing units of formula (II) but no units of formula (I′).

12. 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 the resin solution of claim 1 .

Assignments (7)