IP Library Granted Patent US 9,339,446
Granted Patent B2
US 9,339,446 · App. 12/801,535 · Granted May 17, 2016

Gel composition

Inventors: Lin Lu Healy (Houston, TX); Jack C. Cunningham, Jr. (Houston, TX); David S. Morrison (The Woodlands, TX); Wei Song (Houston, TX); Gina Butuc (Houston, TX)
Assignee: Calumet Penreco, LLC
A61K8/042A61K8/37A61K8/90A61Q1/00A61Q15/00A61Q19/00A61Q19/04C08K5/10
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Quick Facts
Patent No.
US 9,339,446
App. No.
12/801,535
Granted
May 17, 2016
Kind
B2
Abstract

A gel, comprising: an ester and a polymer having at least one of the following rigid block groups; polystyrene, polyethylene, polyvinyl chloride, and phenolics as well as one elastic block that is a member of the group consisting of ethylene/butadiene copolymers, polyisoprene, polybutadiene, ethylene/propylene copolymers, or ethylene-propylene/diene copolymers, wherein the polymer is either triblock copolymers, star polymers, radial polymers, multi-block copolymers, or combinations thereof, wherein the composition is substantially free of mineral oils; wherein the ester's chemical formula is: Wherein n=1, 2, 3, and 4, and R 1 represents a member of the group consisting of: hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, and substituted phenyl; R 2 represents a member of the group consisting of: hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, substituted phenyl, alkylene, phenylene, substituted alkylene, and substituted phenylene, and R 3 represents a member of the group consisting of: alkylene, phenylene, substituted alkylene, or substituted phenylene, and wherein R 4 , R 5 , R 6 all represent a member of the group consisting of: alkylene, phenylene, substituted alkylene, or substituted phenylene, and R 7 , R 8 , R 9 all represent a member of the group consisting of: hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, and substituted phenyl.

Claims (32)

1. A gel composition, comprising:

an ester compound;

a diblock copolymer comprising at least one rigid block selected from the group consisting of polystyrene, polyethylene, polyvinylchloride, and phenolics, and one elastic block selected from the group consisting of ethylene/butadiene copolymers, polyisoprene, polybutadiene, ethylene/propylene copolymers, and ethylene-propylene/diene copolymers, wherein the diblock polymer has a polystyrene content between about 28% and about 40%; and

one or more polymers selected from the group consisting of a triblock copolymer, a star polymer, a radial polymer, a multi-block copolymer, and combinations thereof, wherein the triblock copolymer, star polymer, radial polymer, and multi-block copolymer have a polystyrene content between about 7% and about 30%;

wherein the gel composition is substantially free of mineral oils,

wherein the ester is represented by one of the following formulas:

wherein n=1, 2, 3, or 4, and

R 1 is hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, or substituted phenyl, R 2 is hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, substituted phenyl, alkylene, phenylene, substituted alkylene, or substituted phenylene, and R 3 is alkylene, phenylene, substituted alkylene, or substituted phenylene, and

wherein R 4 , R 5 and R 6 individually are alkylene, phenylene, substituted alkylene, or substituted phenylene, R 7 , R 8 and R 9 individually are hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, or substituted phenyl,

and wherein the diblock copolymer is present in the amount of about 5% to about 20% by weight of the gel, the one or more polymers is present in the amount of about 0.1% to about 5% by weight of the gel, and the ester compound is present in the amount of about 80% to about 92% by weight of the gel.

2. The gel composition of claim 1 , wherein the ester is selected from the group consisting of isopropyl myristate, isopropyl palmitate, C 12 to C 15 alkyl benzoate, octyl methoxycinnamate, octyl dodecyl neopentanoate, propylene glycol dicaprylate/caprate, jojoba oil, and isostearyl neopentanoate.

3. The gel composition of claim 1 , wherein the diblock copolymer is selected from the group consisting of styrene-ethylene/propylene copolymers, styrene-ethylene/butadiene copolymers, styrene-isoprene copolymers, and styrene-butadiene copolymers.

4. The gel composition of claim 1 , wherein the one or more polymers is a triblock copolymer selected from the group consisting of styrene-ethylene/propylene-styrene copolymers, styrene-ethylene/butadiene-styrene copolymers, styrene-isoprene-styrene copolymers, and styrene-butadiene-styrene copolymers.

5. The gel composition of claim 1 , wherein the diblock copolymer is hydrogenated.

6. The gel composition of claim 1 , wherein the one or more polymers is a hydrogenated triblock copolymer.

7. The gel composition of claim 1 , wherein the triblock copolymer includes a grafted functional group.

8. The gel composition of claim 1 , further comprising a suspended component.

9. The gel composition of claim 8 , wherein the suspended component is a solid selected from the group consisting of organic materials, inorganic materials, organometallic materials, phosphorescent materials, and fluorescent materials.

10. The gel composition of claim 8 , wherein the suspended component is a solid selected from the group consisting of zinc oxide, coated zinc oxide, surface-treated zinc oxide, titanium dioxide, surface-treated titanium dioxide, graphite, explosives, air-sensitive chemicals, moisture-sensitive chemicals, boron nitride, iron oxides, talc, mica, plastics, polymers, silica, silicon dioxide, aluminum oxide, metal particles, antibacterials, antibiotics, anesthetics, glass, clays, gums, capsules containing an active ingredient, starch, modified starch, other encapsulated materials, and combinations thereof.

11. The gel composition of claim 8 , wherein the suspended component is a liquid selected from the group consisting of water, water containing a water-soluble material, glycerin, propylene glycol, butylene glycol, alcohols, acids, surfactants, emulsifiers, polyglycerols, ethers, polar esters, fluorinated compounds, perfluoropolyethers, silicones, silicon-containing compounds, and combinations thereof.

12. The gel composition of claim 1 , further comprising an active ingredient.

13. The gel composition of claim 12 , wherein the active ingredient is selected from the group consisting of sunscreens, antiperspirants, deodorants, perfumes, cosmetics, emollients, insect repellants, pesticides, herbicides, fungicides, plasticizers, insecticides, and medicaments.

14. A method of making a gel composition, comprising:

mixing an ester compound with a diblock copolymer compound having at least one rigid block selected from the group consisting of polystyrene, polyethylene, polyvinylchloride, and phenolics, and one elastic block selected from the group consisting of ethylene/butadiene copolymers, polyisoprene, polybutadiene, ethylene/propylene copolymers, and ethylenepropylene/diene copolymers, wherein the diblock polymer has a polystyrene content between about 28% to about 40%, and one or more polymers selected from the group consisting of a triblock copolymer, a star polymer, a radial polymer, a multi-block copolymer, and combinations thereof, wherein the triblock copolymer, star polymer, radial polymer, and multi-block copolymer have a polystyrene content between about 7% and about 30%;

heating the mixture;

agitating the mixture until the mixture becomes homogeneous; and

cooling the mixture,

wherein the gel composition is substantially free of mineral oils,

wherein the ester is represented by one of the following formulas:

wherein n=1, 2, 3, or 4, and

R 1 is hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, or substituted phenyl, R 2 is hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, substituted phenyl, alkylene, phenylene, substituted alkylene, or substituted phenylene, R 3 is alkylene, phenylene, substituted alkylene, or substituted phenylene, R 4 , R 5 and R 6 individually are alkylene, phenylene, substituted alkylene, or substituted phenylene, R 7 , R 8 and R 9 individually are hydrogen, hydrocarbyl, phenyl, methoxyphenyl, alkylphenyl, substituted alkyl, or substituted phenyl,

and wherein the polymer compound is present in the amount of about 5% to about 20% by weight of the gel and the ester compound is present in the amount of about 80% to about 92% by weight of the gel.

Assignments (14)
SECURITY INTEREST Recorded Nov 7, 2017
From: CALUMET REFINING, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 044051/0035 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2017
From: CALUMET KARNS CITY REFINING, LLC
To: CALUMET REFINING, LLC
Reel/Frame 043714/0120 →
CHANGE OF NAME Recorded Sep 26, 2017
From: CALUMET PENRECO, LLC
To: CALUMET KARNS CITY REFINING, LLC
Reel/Frame 044014/0498 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 26, 2017
From: PENRECO
To: CALUMET PENRECO, LLC
Reel/Frame 043704/0341 →
RELEASE OF SECURITY INTEREST Recorded Apr 20, 2016
From: BANK OF AMERICA, N.A. AS ADMINISTRATIVE AGENT
To: CALUMET PENRECO, LLC
Reel/Frame 038331/0566 →
SECURITY INTEREST Recorded Apr 20, 2016
From: CALUMET PENRECO, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 038331/0839 →
RELEASE OF SECURITY INTEREST Recorded Apr 20, 2016
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: CALUMET PENRECO, LLC
Reel/Frame 038332/0414 →
RELEASE OF SECURITY INTEREST Recorded Apr 20, 2016
From: BANK OF AMERICA, N.A.
To: CALUMET PENRECO, LLC
Reel/Frame 038332/0522 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2015
From: M.E. ZUKERMAN SPECIALTY OIL CORPORATION
To: CALUMET PENRECO, LLC
Reel/Frame 034946/0590 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2015
From: CONOCOPHILLIPS COMPANY
To: CALUMET PENRECO, LLC
Reel/Frame 034946/0600 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2015
From: HEALY, LIN LU; CUNNINGHAM, JACK C., JR.; MORRISON, DAVID S.; SON, WEI; BUTUC, GINA
To: PENRECO
Reel/Frame 034946/0582 →
AMENDED AND RESTATED SECURITY INTEREST Recorded Apr 21, 2011
From: CALUMET PENRECO, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 026165/0647 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Mar 8, 2011
From: CALUMET PENRECO, LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 025917/0889 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Mar 8, 2011
From: CALUMET PENRECO, LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 025918/0001 →
Continuity (5)
Continuation 12319751 · Jan 12, 2009
Continuation 10665943 · Sep 19, 2003
Continuation 09419571 · Oct 18, 1999
Provisional Application 60106094 · Oct 29, 1998
Related Publication 20110045983A1 · Feb 24, 2011