IP Library Granted Patent US 10,071,034
Granted Patent B2
US 10,071,034 · App. 14/702,607 · Granted Sep 11, 2018

Solvent compositions

Inventors: Ross Keating Eppler (Emeryville, CA); Karl Fisher (Emeryville, CA); Roberto Vazquez (Emeryville, CA)
Assignee: AMYRIS, INC.
A61K8/31A61Q1/04A61Q5/00A61Q5/065A61Q19/00C11D3/184
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Quick Facts
Patent No.
US 10,071,034
App. No.
14/702,607
Granted
Sep 11, 2018
Kind
B2
Abstract

Provided herein are compositions comprising partially hydrogenated farnesene. In certain embodiments, the compositions are useful as solvents, degreasers, cleaning products, personal care products, and for other uses. Also provided herein are methods of making the compositions and methods of their use.

Claims (51)

1. A composition comprising about 78 wt. % to about 97 wt. % dihydrofarnesene and about 20 wt. % to about 2 wt. % tetrahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives in the composition, wherein the composition is substantially free of C 4 to C 10 volatile, organic oxygenated compounds, wherein the composition further comprises a stabilizer, which, when oxidized, does not form a quinone.

2. The composition of claim 1 that comprises about 83 wt. % to about 97 wt. % dihydrofarnesene and about 16 wt. % to about 2 wt. % tetrahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives in the composition.

3. The composition of claim 1 , wherein the composition comprises about 96 wt. % dihydrofarnesene compared to the total amount of farnesene and farnesene derivatives in the composition.

4. The composition of claim 1 , further comprising about 0.1 wt. % to about 2 wt. % hexahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives in the composition.

5. The composition of claim 1 , further comprising less than about 0.1 wt. % farnesane, compared to the total amount of farnesene and farnesene derivatives in the composition.

6. The composition of claim 1 , further comprising less than about 0.25 wt. % bisabolene, compared to the total amount of farnesene and farnesene derivatives in the composition.

7. The composition of claim 1 , wherein the farnesene and farnesene derivatives comprise, on average, about 1.0 to about 1.25 double bonds per molecule of the farnesene and farnesene derivatives in the composition.

8. The composition of claim 1 , wherein the farnesene and farnesene derivatives comprise, on average, about 1.1 to about 1.2 double bonds per molecule of the farnesene and farnesene derivatives in the composition.

9. The composition of claim 1 , which is formulated as a solvent, a degreaser, a cleaning product, or a personal care product.

10. A composition comprising about 78 wt. % to about 97 wt. % dihydrofarnesene and about 20 wt. % to about 2 wt. % tetrahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives in the composition, wherein the composition further comprises one or more additional components which are not reactants or reactant products produced by hydrogenation of farnesene; wherein the one or more additional components are selected from:

a co-solvent selected from the group consisting of limonene, benzene, high flash aromatic naphtha, soy methyl ester, ethyl lactate, paraffins, dibasic esters, propylene glycol, ethyl alcohol, and a mixture thereof,

a surfactant,

water in an amount greater than 5 wt. % compared to the total weight of the composition,

an emulsifier,

an emollient,

a thickener; and

a mixture thereof.

11. The composition of claim 10 that comprises about 83 wt. % to about 97 wt. % dihydrofarnesene and about 16 wt. % to about 2 wt. % tetrahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives in the composition.

12. The composition of claim 10 , wherein the composition comprises about 96 wt. % dihydrofarnesene compared to the total amount of farnesene and farnesene derivatives in the composition.

13. The composition of claim 10 , further comprising about 0.1 wt. % to about 2 wt. % hexahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives in the composition.

14. The composition of claim 10 , wherein the farnesene and farnesene derivatives comprise, on average, about 1.0 to about 1.25 double bonds per molecule of the farnesene and farnesene derivatives in the composition.

15. The composition of claim 10 , wherein the co-solvent is limonene.

16. The composition of claim 10 , wherein the one additional component is a surfactant.

17. The composition of claim 16 , wherein the surfactant is selected from the group consisting of sodium lauryl ether sulfate, ethoxylated alcohol surfactant, fatty acid diethanolamine, orange oil emulsifier, acrylate-based emulsion copolymer, polyoxyethers of lauryl alcohol, linear isopropylamine dodecylbenzene sulfonate, blended alcohol ethoxylate, alkoxylated alcohol, sodium iminodipropionate, nonionic alcohol ethoxylates, a palm kernel alcohol ethoxylated and propoxylated surfactant, sodium xylene sulfonate, and a mixture thereof.

18. The composition of claim 10 , wherein the one additional component is an emulsifier.

19. The composition of claim 18 , wherein the emulsifier is selected from the group consisting of lauryl alcohol, fatty acid diethanolamine, ammonium methyl sulfate and fatty alcohol ethoxylate, linear alcohol ethoxylate, sodium branched dodecyl benzene sulfonate, and a mixture thereof.

20. The composition of claim 10 , wherein the one additional component is an emollient.

21. The composition of claim 20 , wherein the emollient is selected from the group consisting of fatty acids, alkyl ethoxylates, fatty acid ester ethoxylates, fatty alcohols, polysiloxanes, mucopolysaccharides, polyols, polysaccharides, urea derivatives, PPG-3 benzyl ether myristate, hydrogenated polyisobutene, butyelen/ethylene/styrene copolymer, ethylene/propylene/styrene copolymer, bis-diglyceryl polyacyladipate-2, pentaerythrityl tetraisosterate, C 10 - 30 cholesterol/lanosterol esters, or a mixture thereof.

22. The composition of claim 10 , wherein the one additional component is a thickener.

23. The composition of claim 22 , wherein the thickener is selected from the group consisting of cellulosic thickeners, natural gums, acrylates, starches, stearates, fatty acid alcohols, clays, salts, candelilla wax, carnauba wax, beeswax, oils, linear alcohol ethoxylates, and a mixture thereof.

24. The composition of claim 10 , wherein the composition further comprises at least one additive selected from the group consisting of a buffering agent, pH control agent, fragrance, flavor, defoamer, dye, whitener, brightener, solubilizing material, stabilizer, thickener, corrosion inhibitors, lotions, mineral oils, enzymes, cloud point modifiers, preservative, ion exchanger, chelating agent, sudsing control agent, soil removal agent, softening agent, opacifier, inert diluent, graying inhibitor, polymer, abrasive, exfoliant, and a mixture thereof.

25. A method of cleaning or degreasing a substrate or an object, the method comprising the step of contacting the substrate or the object with the composition of claim 10 .

26. A method of producing a composition, the method comprising:

(a) reacting a composition comprising farnesene with hydrogen in the presence of a hydrogenation catalyst to produce a composition comprising about 60 wt. % to about 100 wt. % dihydrofarnesene, compared to the total amount of farnesene and farnesene derivatives; and

(b) filtering products of step (a) using an adsorbent to remove, volatile, organic oxygenated compounds; and

(c) adding a stabilizer, wherein the stabilizer, which, when oxidized, does not form a quinone.

27. The method of claim 26 , wherein the adsorbent comprises alumina, silica, or a mixture thereof.

28. A composition produced by a method comprising:

(a) reacting a composition comprising farnesene with hydrogen in the presence of a hydrogenation catalyst to produce a composition comprising about 60 wt. % to about 100 wt. % dihydrofarnesene, compared to the total amount of farnesene and farnesene derivatives;

(b) filtering products of step (a) using an adsorbent to remove volatile, organic oxygenated compounds; and

(c) adding a stabilizer, wherein the stabilizer, which, when oxidized, does not form a quinone.

29. The composition of claim 28 that comprises about78 wt. % to about 97 wt. % dihydrofarnesene and that further comprises about 20 wt. % to about 2 wt. % tetrahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives.

30. The composition of claim 28 that comprises about 83 wt. % to about 97 wt. % dihydrofarnesene and that further comprises about 16 wt. % to about 2 wt. % tetrahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives.

31. The composition of claim 28 , wherein the composition further comprises about 0.1 wt. % to 2 wt. % hexahydrofarnesene, compared to the total amount of farnesene and farnesene derivatives.

32. The composition of claim 28 , wherein the farnesene and farnesene derivatives comprise, on average, about 1.0 to about 1.25 double bonds per molecule of the farnesene and farnesene derivatives in the composition.

33. The composition of claim 28 , wherein the stabilizer is butylated hydroxytoluene.

34. The composition of claim 28 , wherein the stabilizer is present at a concentration of about 100 to 500 ppm.

35. The composition of claim 28 , wherein the composition is substantially free of C 4 to C 10 volatile, organic oxygenated compounds.

36. The composition of claim 28 , further comprising a co-solvent, surfactant, water, emulsifier, emollient, thickener, or a mixture thereof.

37. The composition of claim 10 , wherein the surfactant is present in an amount greater than 5 wt. % compared to the total weight of the composition.

38. The composition of claim 10 , wherein the co-solvent is present in an amount greater than 5 wt. % compared to the total weight of the composition.

Assignments (9)
SECURITY INTEREST Recorded May 24, 2024
From: AMYRIS, INC.
To: EUAGORE, LLC
Reel/Frame 067528/0467 →
SECURITY INTEREST Recorded Aug 17, 2023
From: AMYRIS, INC.; AMYRIS CLEAN BEAUTY, INC.; AMYRIS FUELS, LLC; AB TECHNOLOGIES LLC; APRINNOVA, LLC; AMYRIS-OLINKA, LLC; ONDA BEAUTY INC.; UPLAND 1 LLC; AMYRIS ECO-FAB LLC; CLEAN BEAUTY 4U HOLDINGS, LLC; AMYRIS CLEAN BEAUTY LATAM LTDA; INTERFACES INDUSTRIA E COMERCIA DE COSMETICOS LTDA; AMYRIS BIOTECHNOLOGIA DO BRASIL LTDA; AMYRIS EUROPE TRADING B.V. (NETHERLANDS); AMYRIS BIO PRODCUTS PORTUGAL, UNIPESSOAL, LDA; BEAUTY LABS INTERNATIONAL LIMITED; AMYRIS UK TRADING LIMITED
To: EUAGORE, LLC
Reel/Frame 064619/0778 →
SECURITY INTEREST Recorded Aug 3, 2023
From: AMYRIS CLEAN BEAUTY, INC.; AMYRIS FUELS, LLC; AB TECHNOLOGIES LLC; AMYRIS, INC.
To: MUIRISC, LLC
Reel/Frame 064492/0518 →
RELEASE OF SECURITY INTEREST Recorded Feb 14, 2023
From: SCHOTTENFELD OPPORTUNITIES FUND II, L.P.
To: AMYRIS, INC.
Reel/Frame 062760/0818 →
RELEASE OF SECURITY INTEREST Recorded Feb 14, 2023
From: NAXYRIS S.A.
To: AMYRIS, INC.
Reel/Frame 062760/0753 →
SECURITY INTEREST Recorded Oct 18, 2022
From: AMYRIS, INC.
To: FORIS VENTURES, LLC
Reel/Frame 061703/0499 →
GRANT OF PATENT SECURITY INTEREST Recorded Nov 20, 2019
From: AMYRIS, INC.
To: SCHOTTENFELD OPPORTUNITIES FUND II, L.P.
Reel/Frame 051072/0310 →
SECURITY INTEREST Recorded Aug 19, 2019
From: AMYRIS, INC.
To: NAXYRIS S.A.
Reel/Frame 050093/0067 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2015
From: EPPLER, ROSS KEATING; FISHER, KARL; VAZQUEZ, ROBERTO
To: AMYRIS, INC.
Reel/Frame 035899/0885 →
Continuity (4)
Provisional Application 61988053 · May 2, 2014
Provisional Application 61994389 · May 16, 2014
Provisional Application 62052397 · Sep 18, 2014
Related Publication 20150315520A1 · Nov 5, 2015