Alkylphenol copolymer

Patent metadata

Field	Value
Publication number	US-10961476-B2
Application number	US-201916293808-A
Country	US
Kind code	B2
Filing date	Mar 6, 2019
Priority date	Mar 6, 2018
Publication date	Mar 30, 2021
Grant date	Mar 30, 2021

Abstract

An alkylphenol copolymer, such as for use in a petroleum composition, is provided. The alkylphenol copolymer has the following repeating units (A) and (B):

wherein,
x is an integer from 1 to 200; y is an integer from 2 to 200; R 1 is a straight or branched C 1 -C 15 alkyl; and R 2 is a straight or branched C 2 -C 40 alkyl, wherein R 2 is different than R 1 .

First claim

What is claimed is:

1. An alkylphenol copolymer having the following repeating units (A) and (B):

wherein,
x is an integer from 1 to 200;
y is an integer from 2 to 200;
R 1 is a straight or branched C 1 -C 15 alkyl; and
R 2 is a straight or branched C 2 -C 40 alkyl, wherein R 2 is different than R 1 .

2. The alkylphenol copolymer of claim 1 , wherein R 1 is C 8 -C 14 alkyl.

3. The alkylphenol copolymer of claim 1 , wherein R 2 is C 16 -C 40 alkyl.

4. The alkylphenol copolymer of claim 3 , wherein R 2 is C 24 -C 32 alkyl.

5. The alkylphenol copolymer of claim 1 , wherein the alkyl of R 2 contains 3 or more carbon atoms than the alkyl of R 1 .

6. The alkylphenol copolymer of claim 1 , wherein x and y are independently from 5 to 25.

7. The alkylphenol copolymer of claim 1 , where the ratio of the moles of repeating unit (A) to the moles of repeating unit (B) is from about 0.2 to about 3.

8. The alkylphenol copolymer of claim 1 , wherein the number average molecular weight of the alkylphenol copolymer is from about 4,000 to about 60,000 Daltons.

9. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer is a random copolymer.

10. The alkylphenol copolymer of claim 1 , wherein the alkylphenol copolymer is a block copolymer.

11. The alkylphenol copolymer of claim 10 , wherein the block copolymer is formed by a process that comprises:
reacting a phenol monomer used to form the repeating units (A) with a formaldehyde source in a first reaction vessel to form a first oligomer;
reacting a phenol monomer used to form the repeating units (B) with a formaldehyde source in a second reaction vessel to form a second oligomer; and
thereafter, reacting the first oligomer and the second oligomer with a formaldehyde source to form the block copolymer.

12. The alkylphenol copolymer of claim 11 , wherein the ratio of the total number of moles of the formaldehyde source added to the first reaction vessel to the total number of moles of the phenol monomers used to form the repeating units (A) is from about 0.5 to about 1.

13. The alkylphenol copolymer of claim 11 , wherein the ratio of the total number of moles of the formaldehyde source added to the second reaction vessel to the total number of moles of the phenol monomers used to form the repeating units (B) is from about 0.5 to about 1.

14. The alkylphenol copolymer of claim 11 , wherein the phenol monomer used to form the repeating units (A) includes dodecylphenol.

15. The alkylphenol copolymer of claim 11 , wherein the phenol monomer used to form the repeating units (B) includes butylphenol, nonylphenol, tetracosanylphenol, pentacosanylphenol, hexacosanylphenol, heptacosanylphenol, octacosanylphenol, or a combination thereof.

16. A method for modifying a petroleum source, the method comprising adding the alkylphenol copolymer of claim 1 to the petroleum source.

17. The method of claim 16 , wherein the copolymer is present in a concentration of from about 1 to about 2,000 ppm.

18. The method of claim 16 , wherein a copolymer composition is added to the petroleum source that comprises the alkylphenol copolymer and a petroleum-based solvent.

19. The method of claim 18 , wherein solvents constitute from about 30 wt. % to about 99 wt. % of the composition and alkylphenol copolymers constitute from about 1 wt. % to about 70 wt. % of the copolymer composition.

20. The method of claim 18 , wherein the copolymer composition further comprises a corrosion inhibitor, surfactant, neutralizer, stabilizer, plasticizer, biocide, preservative, or a combination thereof.

21. The method of claim 18 , wherein the copolymer composition is added in an amount of from about 10 ppm to about 5,000 ppm based on the combined weight of the copolymer composition and the petroleum source.

22. The method of claim 16 , wherein the alkylphenol copolymer exhibits:
an asphaltene dispersancy parameter of about 500 or less as determined at a non-volatile residue percentage of 15%;
a percent asphaltene inhibition of about 80% or more as determined at a non-volatile residue percentage of 15%;
a Cold Finger paraffinic wax inhibition of about 50% or more;
a no-flow point of about −20° C. or less as determined at a non-volatile residue concentration of 15%; and/or
a static time to gel of about 500 seconds or more as determined at a temperature of −15° C. and at a non-volatile residue concentration of 15%.

23. A petroleum composition comprising the alkylphenol copolymer of claim 1 and a petroleum source.

24. The petroleum composition of claim 23 , wherein the alkylphenol copolymer is present in a concentration of from about 1 to about 1,000 ppm.

25. The petroleum composition of claim 23 , wherein the alkylphenol copolymer exhibits:
an asphaltene dispersancy parameter of about 500 or less as determined at a non-volatile residue percentage of 15%;
a percent asphaltene inhibition of about 80% or more as determined at a non-volatile residue percentage of 15%;
a Cold Finger paraffinic wax inhibition of about 50% or more;
a no-flow point of about −20° C. or less as determined at a non-volatile residue concentration of 15%; and/or
a static time to gel of about 500 seconds or more as determined at a temperature of −15° C. and at a non-volatile residue concentration of 15%.

Assignees

• Si Group Inc

Inventors

• Chichak Kelly S
• Doane Joseph T
• Christofel Brian
• Shanklin Elliott W

Classifications

• C10G71/00 Primary

  Treatment by methods not otherwise provided for of hydrocarbon oils or fatty oils for lubricating purposes · CPC title

• C10G75/04

  by addition of antifouling agents · CPC title

• C10L10/16

  Pour-point depressants · CPC title

• C10L1/195

  obtained by reactions involving only carbon-to-carbon unsaturated bonds · CPC title

• C07C39/06

  Alkylated phenols · CPC title