IP Library Granted Patent US 12,209,069
Granted Patent B2
US 12,209,069 · App. 17/746,626 · Granted Jan 28, 2025

Fatty acid terpene alcohol esters

Inventor: Patrick Foley (New Haven, CT)
Assignee: P2 SCIENCE, INC.
C07C67/08
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 12,209,069
App. No.
17/746,626
Granted
Jan 28, 2025
Kind
B2
Abstract

The present disclosure is directed to novel derivatives of terpenes, particularly derivatives of terpene alcohols, and methods of making them, compositions comprising them, and methods for using them.

Claims (28)

1. A composition comprising at least two compounds of a formula selected from the group consisting of:

wherein the composition is a cosmetic composition, or a personal care composition selected from a soap, skin cream or lotion, balm, shampoo, body wash, hydrating cream, deodorant, antiperspirant, after-shave lotion, cologne, perfume, or other hair care or skin care product; or a composition comprised in an air freshener, insect repellant, detergent, household cleaning product, room spray, pomander, candle, toilet water, talcum powder, shower gel, hair spray, sunscreen, or pet litter.

2. The composition according to claim 1 , wherein the composition further comprises one or more pharmaceutically acceptable, cosmetically acceptable, or industrially acceptable excipients or carriers, selected from the group consisting of solvents, oils, surfactants, emollients, diluents, glidants, abrasives, humectants, polymers, plasticizer, catalyst, antioxidant, coloring agent, flavoring agent, fragrance agent, antiperspirant agent, antibacterial agent, antifungal agent, hydrocarbon, stabilizer, and viscosity controlling agent.

3. The composition of claim 1 , wherein the composition is a cosmetic composition.

4. The composition of claim 1 , wherein the personal care composition is selected from a soap, shampoo, body wash, deodorant, or antiperspirant.

5. A product selected from a cosmetic, soap, skin cream or lotion, balm, shampoo, body wash, hydrating cream, deodorant, antiperspirant, after-shave lotion, cologne, perfume, or other hair care or skin care product, air freshener, insect repellant, detergent, household cleaning product, room spray, pomander, candle, toilet water, talcum powder, shower gel, hair spray, sunscreen, or pet litter, comprising at least two compounds of a formula selected from the group consisting of:

in admixture with one or more pharmaceutically acceptable, cosmetically acceptable, or industrially acceptable excipients or carriers, selected from the group consisting of solvents, oils, surfactants, emollients, diluents, glidants, abrasives, humectants, polymers, plasticizer, catalyst, antioxidant, coloring agent, flavoring agent, fragrance agent, antiperspirant agent, antibacterial agent, antifungal agent, hydrocarbon, stabilizer, and viscosity controlling agent.

6. The product of claim 5 , wherein the product is a cosmetic composition.

7. The product of claim 5 , wherein the product is selected from a soap, shampoo, body wash, deodorant, or antiperspirant.

8. The product of claim 6 , wherein the product is selected from the group consisting of nail polish, eye liner, mascara, lipstick, foundation, concealer, blush, bronzer, eye shadow, lip liner, lip balm, and dermocosmetic.

9. The composition of claim 1 , wherein the composition is a cologne or perfume.

10. The composition of claim 1 , wherein the composition is an air freshener or room spray.

11. The composition of claim 1 , wherein the composition comprises the compounds

and

or the compounds

and

12. The composition of claim 1 , wherein the composition comprises the compound

13. The composition of claim 1 , wherein the composition comprises the compound

and the compound

14. The product of claim 5 , wherein the product comprises the compounds

and

or the compounds

and

15. The product of claim 5 , wherein the product comprises the compound

16. The product of claim 5 , wherein the product comprises the compound

and the compound

17. The composition of claim 1 , wherein the composition does not comprise the compound

18. The product of claim 5 , wherein the product does not comprise the compound

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Feb 6, 2023
From: HG VENTURES LLC
To: P2 SCIENCE, INC.
Reel/Frame 062650/0301 →
SECURITY INTEREST Recorded Dec 3, 2022
From: P2 SCIENCE, INC.
To: HG VENTURES LLC
Reel/Frame 062050/0152 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2022
From: FOLEY, PATRICK
To: P2 SCIENCE, INC.
Reel/Frame 061826/0229 →
Continuity (2)
Provisional Application 63189544 · May 17, 2021
Related Publication 20220380291A1 · Dec 1, 2022
References Cited (87)
US 2020298A · Carothers et al. · 1935 [cited by applicant]
US 3035987A · Weitzel · 1962 [cited by examiner]
US 3335053A · Weitzel · 1967 [cited by applicant]
US 3829505A · Herold et al. · 1974 [cited by applicant]
US 3980697A · El-Chahawi et al. · 1976 [cited by applicant]
US 4021507A · Ford · 1977 [cited by applicant]
US 4070386A · Rossmy · 1978 [cited by applicant]
US 4218379A · Harris et al. · 1980 [cited by applicant]
US 4366270A · Rüter · 1982 [cited by applicant]
US 4381416A · Kyo et al. · 1983 [cited by applicant]
US 5030768A · Chen et al. · 1991 [cited by applicant]
US 5264547A · Yamaguchi et al. · 1993 [cited by applicant]
US 5292845A · Kawasaki · 1994 [cited by applicant]
US 5531910A · Severns et al. · 1996 [cited by applicant]
US 5545601A · Le-Khac · 1996 [cited by applicant]
US 5562847A · Waite et al. · 1996 [cited by applicant]
US 5616679A · Fies et al. · 1997 [cited by applicant]
US 6001789A · Trinh et al. · 1999 [cited by applicant]
US 6117521A · Yoshida et al. · 2000 [cited by applicant]
US 6348618B1 · Anderson et al. · 2002 [cited by applicant]
US 6355845B1 · Clement et al. · 2002 [cited by applicant]
US 6359101B1 · O'Connor et al. · 2002 [cited by applicant]
US 6369025B1 · Trinh et al. · 2002 [cited by applicant]
US 7355066B1 · Johnson et al. · 2008 [cited by applicant]
US 7445790B2 · Oguchi et al. · 2008 [cited by applicant]
US 9068091B2 · Hofstra et al. · 2015 [cited by applicant]
US 9200298B2 · Lee et al. · 2015 [cited by applicant]
US 9982073B2 · Ghandi et al. · 2018 [cited by applicant]
US 10059801B2 · Foley et al. · 2018 [cited by applicant]
US 10844169B2 · Foley et al. · 2020 [cited by applicant]
US 11008271B2 · Yang et al. · 2021 [cited by applicant]
US 11518850B2 · Foley et al. · 2022 [cited by applicant]
US 11827746B2 · Foley et al. · 2023 [cited by applicant]
US 11872300B2 · Foley et al. · 2024 [cited by applicant]
US 20040152830A1 · Kim et al. · 2004 [cited by applicant]
US 20040202689A1 · Subramanyan et al. · 2004 [cited by applicant]
US 20050256347A1 · Goebbel et al. · 2005 [cited by applicant]
US 20060018977A1 · Bruza et al. · 2006 [cited by applicant]
US 20080311066A1 · Samain et al. · 2008 [cited by applicant]
US 20090169652A1 · Osborne · 2009 [cited by examiner]
US 20120046244A1 · Rogers et al. · 2012 [cited by applicant]
US 20130202543A1 · Küper et al. · 2013 [cited by applicant]
US 20170057940A1 · Foley et al. · 2017 [cited by applicant]
US 20170088536A1 · Foley et al. · 2017 [cited by applicant]
US 20170283553A1 · Foley et al. · 2017 [cited by applicant]
US 20180071188A1 · Barhoum et al. · 2018 [cited by applicant]
US 20190184049A1 · Salaam-Zayid et al. · 2019 [cited by applicant]
US 20200179247A1 · Verdier et al. · 2020 [cited by applicant]
US 20200392287A1 · Foley et al. · 2020 [cited by applicant]
US 20220259524A1 · Struillou · 2022 [cited by examiner]
CN 104307428 · 2015 [cited by applicant]
DE 102005025739A1 · 2006 [cited by applicant]
EP 191828854 · 2019 [cited by examiner]
GB 841903 · 1960 [cited by applicant]
JP 2006273796A · 2006 [cited by applicant]
JP 2008050415A · 2008 [cited by applicant]
JP 2019005262A · 2019 [cited by applicant]
JP 6745563 · 2020 [cited by examiner]
JP 2020152663A · 2020 [cited by applicant]
WO WO2006057086 · 2006 [cited by applicant]
WO WO2016033437A2 · 2016 [cited by applicant]
WO WO2019028053A1 · 2019 [cited by applicant]
WO WO2019029808A1 · 2019 [cited by applicant]
WO WO2019059375 · 2019 [cited by applicant]
JP6745563 translated (Year: 2020). [cited by examiner]
Dictionary (p. 1, obtained from internet 2024) (Year: 2024). [cited by examiner]
Desaubry, et al., “Toward Higher Polyprenols Under ‘Prebiotic’ Conditions,” [cited by applicant]
Halbert, S., “Plant-derived compounds and extracts with potential as aphid repellents”, [cited by applicant]
Hanson, “Chiral Acylic Synthetic Intermediates from Readily Available Monoterpenoids,” [cited by applicant]
Marchal et al., “Lyotropic liquid crystal behaviour of azelate and succinate monoester surfactants based on fragrance alcohols”, [cited by applicant]
Nagai, “The Formation of Ethers from dl-Citronellol in the Presence of Boron Trifluoride Etherate,” [cited by applicant]
Nagai, et al., “The Formation of Ethers from Unsaturated Aliphatic Alcohols in the Presence of Boron Trifluoride Etherate,” [cited by applicant]
PubChem CID 13469549, 11 pages, (2007); retrieved on Sep. 10, 2018 from http://pubchem.ncbi.nlm.nih.gov/compound/013469549#section=Top>. [cited by applicant]
PubChem, OPEN Chemistry Database, PubChem CID 8892, pp. 4, (2004), 60 pages. [cited by applicant]
PubChem, OPEN Chemistry Database, PubChem SID 105168722, PubChem CID 112049, (2011), 7 pages. [cited by applicant]
PubChem, OPEN Chemistry Database, PubChem SID 355155508, PubChem CID 114416, (2018), 6 pages. [cited by applicant]
PubChem, OPEN Chemistry Database, PubChem CID 11172890, (2006), 10 pages. [cited by applicant]
PubChem, OPEN Chemistry Database, PubChem CID 23297377, (2007), 9 pages. [cited by applicant]
Takahashi, et al., “Cationic Polymerization Behavior of Alkoxyallenes,” [cited by applicant]
Wheeler et al. “2,3-Dihydrofarnesyl and citronellyl esters in the paracloacal gland secretions of the brown caiman ( [cited by applicant]
Worzakowska, “Synthesis, Characterization, and Thermal Properties of New Flavor Compounds,” [cited by applicant]
Worzakowska, “Thermal Properties of Neryl Long-Chain Esters Obtained Under Microwave Irradiation,” [cited by applicant]
Barrere, et al., “Polyester synthesis in aqueous miniemulsion,” [cited by applicant]
Paroul, et al., “Solvent-Free Production of Bioflavors by Enzymatic Esterification of Citronella ( [cited by applicant]
Rashid, A., et al., “Enzymatic Synthesis of Citronellyl Palmitate in Organic Media: Process Optimization and Kinetic Evaluation”, Asian Journal of Chemistry, 28(2):298-300 (2016). [cited by applicant]
Schlenk, W. Jr., “Asymmetric urea inclusion lattice. II. Configurational lattice coordination of the guest molecules,” [cited by applicant]
Swift, K., “Catalytic Transformations of the Major Terpene Feedstocks”, Topics in Catalysis, 27(1-4): 143-155 (2004). [cited by applicant]