IP Library Granted Patent US 11,168,182
Granted Patent B2
US 11,168,182 · App. 16/914,056 · Granted Nov 9, 2021

Star macromolecules for personal and home care

Inventors: Wojciech Jakubowski (Sugar Land, TX); Patrick McCarthy (Pittsburgh, PA); Nicolay Tsarevsky (Dallas, TX); James Spanswick (Pittsburgh, PA)
Assignee: Pilot Polymer Technologies, Inc.
C08G83/003A61K8/72A61K8/8147A61K8/8152A61K8/90A61Q19/00C08F265/02C08F265/04C08F293/005C08F299/04C08F299/0492A61K2800/10A61K2800/48C08J2300/206
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Quick Facts
Patent No.
US 11,168,182
App. No.
16/914,056
Granted
Nov 9, 2021
Kind
B2
Abstract

A polymer composition comprising star macromolecules is provided. Each star macromolecule has a core and five or more arms, wherein the number of arms within a star macromolecule varies across the composition of star molecules. The arms on a star are covalently attached to the core of the star; each arm comprises one or more (co)polymer segments; and at least one arm and/or at least one segment exhibits a different solubility from at least one other arm or one other segment, respectively, in a reference liquid of interest.

Claims (39)

1. A star macromolecule represented by the Formula:

[( P 1) q 1-( P 2)2] t -Core-[( P 3)3] r   Formula

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;

q2 represents the number of repeat units in P2;

q3 represents the number of repeat units in P3;

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

one or more of the repeat units of monomeric residues of polymerized monomers within P1 and P3 comprise one or more of (meth)acrylic acid and 2-acrylamido-2-methyl-1-propanesulfonic acid; and

P1 and P2 are different.

2. The star macromolecule of claim 1 is an oil-soluble rheology-modifying star macromolecule.

3. The star macromolecule of claim 1 is a thickener for an oil-based system.

4. The star macromolecule of claim 1 controls rheology in an oil based system.

5. The star macromolecule of claim 1 wherein:

q1 has a value of between 10 and 1000;

q2 has as a value between 50 and 1000; and

q3 has a value between 20 and 500.

6. The star macromolecule of claim 1 wherein the molar ratio of r to t is in the range of between 40:1 and 1:40.

7. The star macromolecule of claim 1 , wherein the arms represented by [(P1) q1 -(P2) q2 ] t extend beyond the arms represented by [(P3) q3 ] r .

8. The star macromolecule of claim 1 , wherein the number of polymeric arms (r+t) is between 5 and 500.

9. The star macromolecule of claim 1 , wherein (r+t) is greater than 15.

10. The star macromolecule of claim 1 , wherein q2 is greater than q3.

11. The star macromolecule of claim 1 , wherein P2 represents a hydrophobic polymeric segment comprised of repeat units of monomeric residues of polymerized monomers.

12. The star macromolecule 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.

13. The star macromolecule 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.

14. The star macromolecule 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.

15. The star macromolecule 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.

16. The star macromolecule 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.

17. The star macromolecule 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) diacrylate (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.

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

19. The star macromolecule 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 star macromolecule 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.

Assignments (3)
SECURITY INTEREST Recorded Mar 2, 2023
From: PILOT CHEMICAL CORP.; PILOT POLYMER TECHNOLOGIES, INC.; LIQUID MINERALS GROUP LTD.
To: U.S. BANK NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 062859/0909 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2020
From: JAKUBOWSKI, WOJCIECH; MCCARTHY, PATRICK; TSAREVSKY, NICOLAY; SPANSWICK, JAMES
To: ATRP SOLUTIONS, INC.
Reel/Frame 053162/0710 →
CHANGE OF NAME Recorded Jul 9, 2020
From: ATRP SOLUTIONS, INC.
To: PILOT POLYMER TECHNOLOGIES, INC.
Reel/Frame 053185/0461 →
Continuity (8)
Continuation 16286267 · Feb 26, 2019
Continuation 15174727 · Jun 6, 2016
Continuation 14037031 · Sep 25, 2013
Continuation 13410700 · Mar 2, 2012
Continuation 12926143 · Oct 27, 2010
Continuation In Part 12799411 · Apr 23, 2010
Provisional Application 61214397 · Apr 23, 2009
Related Publication 20200325282A1 · Oct 15, 2020