IP Library Granted Patent US 9,382,370
Granted Patent B2
US 9,382,370 · App. 14/037,031 · Granted Jul 5, 2016

Star macromolecules for personal and home care

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Quick Facts
Patent No.
US 9,382,370
App. No.
14/037,031
Granted
Jul 5, 2016
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 (74)

1. A compound represented by Formula X:

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

wherein:

Core represents a crosslinked polymeric segment;

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

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

P3 represents a polymeric segment comprised of monomeric residues of polymerized hydrophilic monomers;

q1 represents the number of the monomeric residues in P1;

q2 represents the number of the monomeric residues in P2;

q3 represents the number of the monomeric residues in P3 of between 30 and 500;

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

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

wherein:

i) the ratio of r to t is in the range of between 20:1 and 2:1; and

ii) at least one polymeric arm has a number average molecular weight of greater than 10,000 g/mol.

2. The compound of claim 1 , wherein q2 is greater than q3.

3. The compound of claim 1 , wherein the number average molecular weight of the at least one polymeric arm is between 10,000 g/mol and 200,000 g/mol.

4. The compound of claim 1 , wherein:

i) the polymeric segment P1 has an HLB less than 8;

ii) the polymeric segment P2 has an HLB equal to or greater than 8; or

iii) the polymeric segment P3 has an HLB equal to or greater than 8.

5. The compound of claim 1 , wherein the arms represented by [(P1) q1 -(P2) q2 ] have an HLB value greater than 18.

6. The compound of claim 1 , wherein the polymeric segment P1 is a hydrophobic polymeric segment having an HLB value of less than 7.

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

8. The compound of claim 7 , wherein the polymeric segment P1 is a hydrophobic homopolymeric segment.

9. The compound of claim 1 , wherein the arms represented by [(P1) q1 -(P2) q2 ] have a hydrophilic segment at its proximal end and a hydrophobic segment at its distal end, relative to the crosslinked core.

10. The compound of claim 1 , wherein the crosslinked core comprises a hydrophobic crosslinked polymeric segment.

11. The compound of claim 1 , wherein the crosslinked core contains additional functionality and/or expanded free volume.

12. The compound of claim 1 , wherein at least one polymeric segment is prepared by living ionic polymerization.

13. The compound of claim 12 , wherein the living ionic polymerization is anionic polymerization.

14. The compound of claim 1 , wherein at least one polymeric segment is prepared by free radical polymerization.

15. The compound of claim 1 , wherein at least one polymeric segment is prepared by living/controlled radical polymerization (CRP).

16. The compound of claim 15 , wherein living/controlled radical polymerization is stable free radical polymerization (SFRP), degenerative chain transfer polymerization (DT), or atom transfer radical polymerization (ATRP).

17. The compound of claim 1 , wherein the compound has a molecular weight of greater than 100,000 g/mol and forms a clear, homogeneous gel when dissolved in water at a concentration of at least 0.2 wt. %;

wherein the gel has:

i) a dynamic viscosity of at least 20,000 cP;

ii) a salt-induced break value of at least 60%;

iii) a shear-thinning value of at least 10; and/or

iv) an emulsion value of greater than 12 hours.

18. The compound of claim 17 , wherein the gel has a viscosity of greater than 40,000 cP at a pH between 6 to 11.

19. The compound of claim 17 , wherein the gel has a viscosity of less than 5,000 cP at a shear rate of 4 sec-1.

20. The compound of claim 1 , wherein the compound is a rheology-modifying compound.

21. The compound of claim 1 , wherein the compound is an enhanced oil recovery additive.

22. A compound represented by Formula X:

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

wherein:

Core represents a crosslinked polymeric segment;

P1 represents a polymeric segment comprised of monomeric residues of polymerized water-insoluble monomers;

P2 represents a polymeric segment comprised of monomeric residues of polymerized water-soluble monomers;

P3 represents a polymeric segment comprised of monomeric residues of polymerized water-soluble monomers;

q1 represents the number of the monomeric residues in P1;

q2 represents the number of the monomeric residues in P2;

q3 represents the number of the monomeric residues in P3 of between 30 and 500;

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

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

wherein:

i) the ratio of r to t is in the range of between 20:1 and 2:1; and

ii) at least one polymeric arm has a number average molecular weight of greater than 10,000 g/mol.

23. A compound represented by Formula X:

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

wherein:

Core represents a crosslinked polymeric segment;

P1 represents a polymeric segment having an HLB less than 8 and comprised of monomeric residues of polymerized monomers;

P2 represents a polymeric segment having an HLB equal to or greater than 8 and comprised of monomeric residues of polymerized monomers;

P3 represents a polymeric segment having an HLB equal to or greater than 8 and comprised of monomeric residues of polymerized monomers;

q1 represents the number of the monomeric residues in P1;

q2 represents the number of the monomeric residues in P2;

q3 represents the number of the monomeric residues in P3 of between 30 and 500;

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

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

wherein:

i) the ratio of r to t is in the range of between 20:1 and 2:1; and

ii) at least one polymeric arm has a number average molecular weight of greater than 10,000 g/mol.

24. A composition, comprising the compound of claim 1 .

Assignments (5)
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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY PREVIOUSLY RECORDED AT REEL: 046986 FRAME: 0143. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jan 15, 2019
From: ATRP SOLUTIONS, INC.
To: PILOT POLYMER TECHNOLOGIES, INC.
Reel/Frame 048077/0454 →
SECURITY INTEREST Recorded Sep 5, 2018
From: PILOT POLYMER TECHNOLOGIES, INC.
To: U.S. BANK NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 046794/0322 →
CHANGE OF NAME Recorded Aug 30, 2018
From: ATRP SOLUTIONS, INC.
To: PILOT POLYMER TECHNOLGIES, INC.
Reel/Frame 046986/0143 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2014
From: JAKUBOWSKI, WOJCIECH; MCCARTHY, PATRICK; TSAREVSKY, NICOLAY; SPANSWICK, JAMES
To: ATRP SOLUTIONS, INC.
Reel/Frame 032063/0304 →