Oil soluble rheology modifying star macromolecules

Inventors: Wojciech Jakubowski (Sugar Land, TX); Patrick McCarthy (Pittsburgh, PA); Nicolay Tsarevsky (Dallas, TX); James Spanswick (Pittsburgh, PA)

Assignee: Pilot Polymer Technologies, Inc.

C08G83/003 A61K8/72 A61K8/8147 A61K8/8152 A61K8/90 A61Q19/00 C08F265/04 C08F293/005 C08F299/04 C08F299/0492 A61K2800/10 A61K2800/48 C08J2300/206

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 10,221,285
App. No.: 15/174,727
Granted: Mar 5, 2019
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

Oil soluble rheology modifying star macromolecules having a core and five or more polymeric arms, and compositions comprising the same. The polymeric arms on a star are covalently attached to the core of the star; each polymeric arm comprises one or more (co)polymer segments; and at least one polymeric arm and/or at least one polymeric segment exhibits a different solubility from at least one other polymeric arm or one other polymeric segment, respectively, in a reference liquid of interest. The oil soluble rheology modifying star macromolecules and compositions comprising the same for use in oil based systems.

Claims (54)

1. An oil composition comprising at least one rheology-modifying star macromolecule represented by Formula A:

[(P1) q1 -(P2) q2 ] t -Core-[(P3) q3 ] r Formula A

wherein:

Core represents a crosslinked polymeric segment;

P1 represents a hydrophobic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers;

P2 represents a polymeric segment comprised of repeat units of monomeric residues of polymerized monomers;

P3 represents a hydrophobic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers;

q1 represents the number of repeat units in P1 and has a value between 10 and 1000;

q2 represents the number of repeat units in P2 and has a value between 50 and 1000;

q3 represents the number of repeat units in P3 and has a value between 20 and 500;

t represents the number of copolymeric arms covalently attached to the Core;

r represents the number of polymeric arms covalently attached to the Core; and

wherein:

i) the molar ratio of r to t is in the range of between 40:1 and 1:40;

ii) the arms represented by [(P1) q1 -(P2) q2 ] t extend beyond the arms represented by [(P3) q3 ] r ; and

wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, or P3 comprise a monomeric residue of a polymerized: N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate, N,N-dimethylaminoethyl acrylamide, quaternised N,N-dimethylaminoethyl acryl amide, N,N-dimethylaminoethyl methacrylamide, quaternised N,N-dimethylaminoethyl methacrylamide, N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate, quaternised N,N-dimethyl-aminoethyl acrylate, quaternised N,N-dimethylaminoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, 2-(dimethylamino)ethyl methacrylate, 2-(trimethylamino)ethyl methacrylate, methyl acrylate, ethyl acrylate, n-butyl acrylate, iso-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, decyl acylate, or octyl acrylate.

2. The oil composition of claim 1 , wherein the at least one rheology-modifying star macromolecule is an oil-soluble rheology-modifying star macromolecule.

3. The oil composition of claim 1 , wherein the at least one rheology-modifying star macromolecule is soluble in a reference liquid of interest comprising oil.

4. The oil composition of claim 1 , wherein the at least one rheology-modifying star macromolecule is a thickener for an oil-based system.

5. The oil composition of claim 1 , wherein the at least one rheology-modifying star macromolecule provides rheology control over viscosity in an oil based system.

6. The oil composition of claim 1 , wherein the number of polymeric arms (r+t) is between 5 and 500.

7. The oil composition of claim 1 , wherein (r+t) is greater than 15.

8. The oil composition of claim 1 , wherein q2 is greater than q3.

9. The oil composition of claim 1 , wherein P2 represents a hydrophobic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers.

10. The oil composition of claim 1 , wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, or P3 further comprise a monomeric residue of a polymerized alkyl(meth)acrylate.

11. The oil composition of claim 1 , wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, or P3 further comprise a monomeric residue of a polymerized methyl methacrylate.

12. The oil composition of claim 1 , wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, and P3 further comprise a monomeric residue of a polymerized methyl methacrylate.

13. The oil composition of claim 1 , wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, or P3 further comprise a monomeric residue of a polymerized styrene optionally substituted with one or more C1-C12 straight or branched chain alkyl groups.

14. The oil composition of claim 1 , wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, or P3 further comprise a monomeric residue of a polymerized: dodecyl acrylate, N-dodecyl methacrylamide, styrene or 2-ethylhexyl methacrylate.

15. The oil composition of claim 1 , wherein the repeat units of monomeric residues of polymerized monomers within P1, P2, or P3 further comprise a monomeric residue of a polymerized acrylamide.

16. The oil composition of claim 1 , wherein the Core comprises monomeric residues of polymerized monomers comprising: 1,2-divinylbenzene; 1,3-divinylbenzene; 1,4-divinylbenzene; 1,2-ethanediol di(meth)acrylate; 1,3-propanediol di(meth)acrylate; 1,4-butanediol di(meth)acrylate; 1,5-hexanediol di(meth)acrylate; divinylbenzene; ethyleneglycol di(meth)acrylate; di(ethylene glycol) di acrylate (DEGlyDA); propyleneglycol di(meth)acrylate; butyleneglycol di(meth)acrylate; triethyleneglycol di(meth)acrylate; polyethyleneglycol di(meth)acrylate; polypropyleneglycol di(meth)acrylate; polybutyleneglycol di(meth)acrylate; allyl(meth)acrylate; glycerol di(meth)acrylate; trimethylolpropane ti(meth)acrylate; pentaerythritol tetra(meth)acrylate; ally′ methacrylate; allyl acrylate, di(ethylene glycol) diacrylate (DEGlyDA), or divinylbenzene.

17. An oil based system additive, comprising the oil composition of claim 1 .

18. The oil composition of claim 1 , wherein the polymeric segments P1, P2, and/or P3 are random polymeric segments.

19. The oil composition of claim 1 , wherein the core comprises, by weight:

about 0.5%, or more, monomeric residues of polymerized monomers from P2 and P3, and

about 0.5%, or more, monomeric residues of polymerized monomers different from the monomeric residues of polymerized monomers from P1, P2, or P3.

20. The oil composition of claim 1 , wherein the Core is crosslinked by a crosslinker comprising ethyleneglycol di(meth)acrylate; trimethylolpropane tri(meth)acrylate; propyleneglycol di(meth)acrylate; di(ethylene glycol) diacrylate (DEGlyDA); triethyleneglycol di(meth)acrylate; polyethyleneglycol di(meth)acrylate; polypropyleneglycol di(meth)acrylate; 1,4-divinylbenzene; 1,2-divinylbenzene; 1,3-divinylbenzene; 1,2-ethanediol di(meth)acrylate; 1,3-propanediol di(meth)acrylate; 1,4-butanediol di(meth)acrylate; 1,5-hexanediol di(meth)acrylate; divinylbenzene; butyleneglycol di(meth)acrylate; polybutyleneglycol di(meth)acrylate; allyl(meth)acrylate; glycerol di(meth)acrylate; pentaerythritol tetra(meth)acrylate; allyl methacrylate; allyl acrylate; or divinylbenzene.

21. An oil composition comprising at least one rheology-modifying star macromolecule represented by Formula A: