IP Library Granted Patent US 11,345,846
Granted Patent B2
US 11,345,846 · App. 16/919,275 · Granted May 31, 2022

Alkylphenol copolymer

Inventor: Kelly S. Chichak (Halfmoon, NY)
Assignee: SI Group, Inc.
C09K8/524C08G8/10C08L65/02
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Quick Facts
Patent No.
US 11,345,846
App. No.
16/919,275
Granted
May 31, 2022
Kind
B2
Abstract

An alkylphenol copolymer, such as for use in a petroleum composition, is provided. The alkylphenol copolymer has at least the following repeating unit (I): wherein: A is a direct bond or an alkylene; X is —C(O)O—, —OC(O)—, —C(O)N(R 6 )—, —N(R 6 )C(O)—, —C(O)—, —N(R 6 )—, —O—, or —S—; R 6 is H or an alkyl; R 1 includes a C 1 -C 80 alkyl, a C 2 -C 20 alkenyl, a C 2 -C 20 alkynyl, a C 3 -C 12 aryl, or a polyether; and n is an integer from 1 to 200. The present invention also provides a method for forming the alkylphenol copolymer containing the aforementioned repeating unit (I) as well as a method for forming a monomer for forming repeating unit (I).

Claims (41)

1. An alkylphenol copolymer comprising the following repeating units (I) and (II):

wherein:

A is an alkylene;

X is —C(O)O—, —OC(O)—, —C(O)N(R 6 )—, —N(R 6 )C(O)—, —N(R 6 )—, or —S—;

R 6 is H or an alkyl;

R 1 includes a C 1 -C 80 alkyl, a C 2 -C 20 alkenyl, a C 2 -C 20 alkynyl, a C 3 -C 12 aryl, or a polyether;

R 2 is a C 1 -C 80 alkyl;

n is an integer from 1 to 200; and

m is an integer from 1 to 400.

2. The alkylphenol copolymer of claim 1 , wherein A is a C 1 -C 8 alkylene.

3. The alkylphenol copolymer of claim 1 , wherein X is —C(O)O—.

4. The alkylphenol copolymer of claim 1 , wherein R 1 includes a C 10 -C 80 alkyl.

5. The alkylphenol copolymer of claim 1 , wherein R 1 includes a C 20 -C 80 alkyl.

6. The alkylphenol copolymer of claim 1 , wherein R 1 includes a polyether.

7. The alkylphenol copolymer of claim 6 , wherein the polyether includes a polyethylene glycol.

8. The alkylphenol copolymer of claim 1 , wherein n is an integer from 1 to 100.

9. The alkylphenol copolymer of claim 1 , wherein the repeating unit (I) comprises from 0.1% to 75% of the repeating units of the alkylphenol copolymer.

10. The alkylphenol copolymer of claim 1 , wherein the repeating unit (II) comprises from 25% to 98% of the repeating units of the alkylphenol copolymer.

11. The alkylphenol copolymer of claim 1 , wherein the repeating unit (II) comprises a combination of repeating unit (III) and repeating unit (IV):

wherein:

R 3 is a C 1 -C 15 alkyl;

R 4 is a C 2 -C 80 alkyl, wherein R 3 and R 4 are different;

o is an integer from 1 to 200; and

p is an integer from 1 to 200.

12. The alkylphenol copolymer of claim 11 , wherein R 3 is a C 8 -C 14 alkyl.

13. The alkylphenol copolymer of claim 11 , wherein R 4 is a C 20 -C 80 alkyl.

14. The alkylphenol copolymer of claim 13 , wherein R 4 includes from 24 to 34 carbon atoms.

15. The alkylphenol copolymer of claim 11 , wherein the alkyl of R 4 contains 3 or more carbon atoms than the alkyl of R 3 .

16. The alkylphenol copolymer of claim 11 , wherein o and p are independently from 5 to 25.

17. The alkylphenol copolymer of claim 11 , wherein the ratio of the moles of the repeating unit (III) to the moles of the repeating unit (IV) is from about 0.2 to about 5.

18. A paraffin inhibitor composition comprising the alkylphenol copolymer of claim 1 .

19. An asphaltene dispersant composition comprising the alkylphenol copolymer of claim 1 .

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

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

22. A method for forming the alkylphenol copolymer of claim 1 , the method comprising polymerizing compound (VIII), compound (IX), and a formaldehyde source, wherein compound (VIII) and compound (IX) have the following structure:

wherein:

A is an alkylene;

X is —C(O)O—, —OC(O)—, —C(O)N(R 6 )—, —N(R 6 )C(O)—, —N(R 6 )—, or —S—;

R 6 is H or an alkyl;

R 1 includes a C 1 -C 80 alkyl, a C 2 -C 20 alkenyl, a C 2 -C 20 alkynyl, a C 3 -C 12 aryl, or a polyether; and

R 2 is a C 1 -C 80 alkyl.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2021
From: CHICHAK, KELLY
To: SI GROUP, INC.
Reel/Frame 055365/0835 →
Continuity (2)
Provisional Application 62870186 · Jul 3, 2019
Related Publication 20210002539A1 · Jan 7, 2021