IP Library Granted Patent US 12,290,581
Granted Patent B2
US 12,290,581 · App. 17/531,156 · Granted May 6, 2025

Non-petrochemically derived cationic emulsifiers and related compositions

Inventor: Rocco Burgo (Mullica Hill, NJ)
Assignee: INOLEX INVESTMENT CORPORATION
A61K8/06A61K8/44A61Q5/00A61Q19/00C07C229/08A61K2800/10
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 12,290,581
App. No.
17/531,156
Granted
May 6, 2025
Kind
B2
Abstract

The invention includes a neutralized amino acid ester emulsifier, emulsions and compositions containing the emulsifier, and related methods. The emulsifier is a neutralized amino acid ester that is a reaction product of a neutral amino acid with a fatty alcohol and is represented by formula (I): wherein R 1 is an alkyl group that has 6 to 24 carbon atoms; R 2 is an alkyl group that has 6 to 36 carbon atoms; and the amine group of the amino acid is neutralized with an acid. The emulsifier is cationic. Also included are stable emulsions and compositions, preferably personal care compositions, that include the emulsifier and which may have pH levels of 5.5 or greater. Encompassed within the scope of the invention are methods of increasing the substantivity of a composition to a negatively charged substrate using the emulsifier, methods of emulsifying and methods of preparing a personal care composition using the emulsifier.

Claims (36)

1. An emulsifier for the preparation of a stable emulsion comprising a salt of a compound of Formula (I):

wherein R 1 is an unsubstituted, saturated, linear alkyl group having 10 to 12 carbon atoms;

R 2 is an unsubstituted, linear or branched, saturated or unsaturated, alkyl group having 12 to 24 carbon atoms; and

wherein the salt is formed by neutralization with an organic acid.

2. The emulsifier of claim 1 , wherein the carbon present in the compound of Formula (I) is obtained from vegetable matter.

3. A personal care formulation comprising the emulsifier of claim 1 .

4. A composition consisting of one or more fatty alcohols having 12 to 24 carbon atoms and a salt of a compound of Formula (I):

wherein R 1 is an unsubstituted, saturated, linear alkyl group having 10 to 12 carbon atoms;

R 2 is an unsubstituted, linear or branched, saturated or unsaturated, alkyl group having 12 to 24 carbon atoms;

wherein the salt is formed by neutralization with an organic acid;

and optionally one or more additives selected from the group consisting of amino acids, glycerine and derivatives thereof, water, pH balancing agents, and pH adjusters.

5. The composition of claim 4 , wherein the carbon present in the compound of Formula (I) is derived from vegetable matter.

6. The emulsifier of claim 1 , wherein the emulsifier further comprises a fatty alcohol having 12 to 24 carbon atoms.

7. The emulsifier of claim 6 , wherein the fatty alcohol is selected from the group consisting of lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, isostearyl alcohol, octyldodecyl alcohol, arachidyl alcohol, behenyl alcohol, Brassica alcohol, and combinations thereof.

8. The emulsifier of claim 7 , wherein R 2 is selected from the group consisting of lauryl, myristyl, palmityl, stearyl, oleyl, isostearyl, octyldodecyl, arachidyl, behenyl, brassicyl, and combinations thereof.

9. The emulsifier of claim 1 , wherein R 2 is selected from the group consisting of lauryl, myristyl, palmityl, stearyl, oleyl, isostearyl, octyldodecyl, arachidyl, behenyl, brassicyl, and combinations thereof.

10. The emulsifier of claim 1 , wherein R 2 is brassicyl or has 14 to 22 carbon atoms.

11. The emulsifier of claim 10 , wherein the emulsifier further comprises Brassica alcohol or a fatty alcohol having 14 to 22 carbon atoms.

12. The emulsifier of claim 1 , wherein the emulsifier is selected from octyldodecyl aminolaurate esylate, brassicyl aminolaurate esylate, isostearyl aminolaurate esylate, and mixtures thereof.

13. The emulsifier of claim 1 , wherein the organic acid is selected from citric acid, ethanesulfonic acid, acetic acid, formic acid, and oxalic acid.

14. The emulsifier of claim 13 , wherein the organic acid is ethanesulfonic acid.

15. The emulsifier of claim 2 , wherein R 2 is derived from rapeseed oil, palm oil, coconut oil, jojoba oil, or a mixture thereof.

16. The personal care formulation of claim 3 , wherein the personal care formulation further comprises water and has a pH of about 5.0 to about 9.3.

17. The personal care formulation of claim 16 having a pH of about 6.5 to about 8.5.

18. The personal care formulation of claim 3 , wherein the salt of a compound of Formula (I) is present in the formulation in a concentration of about 0.1% by weight to about 10% by weight.

19. The composition of claim 4 , wherein the one or more fatty alcohols are selected from the group consisting of lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, isostearyl alcohol, octyldodecyl alcohol, arachidyl alcohol, behenyl alcohol, Brassica alcohol, and combinations thereof; and wherein R 2 is selected from the group consisting of lauryl, myristyl, palmityl, stearyl, oleyl, isostearyl, octyldodecyl, arachidyl, behenyl, brassicyl, and combinations thereof.

20. The composition of claim 4 , wherein the one or more fatty alcohols is selected from Brassica alcohol or a fatty alcohol having 14 to 22 carbon atoms; and wherein R 2 is brassicyl or has 14 to 22 carbon atoms.

21. The composition of claim 4 , wherein the salt of a compound of Formula (I) is selected from octyldodecyl aminolaurate esylate, brassicyl aminolaurate esylate, isostearyl aminolaurate esylate, and mixtures thereof.

22. The composition of claim 4 , wherein the organic acid is selected from citric acid, ethanesulfonic acid, acetic acid, formic acid, and oxalic acid.

23. The composition of claim 22 , wherein the organic acid is ethanesulfonic acid.

24. The composition of claim 5 , wherein R 2 is derived from rapeseed oil, palm oil, coconut oil, jojoba oil, or a mixture thereof.

25. A personal care formulation comprising the composition of claim 4 .

26. The personal care formulation of claim 25 , wherein the formulation further comprises water and has a pH of about 5.0 to about 9.3.

27. The personal care formulation of claim 26 having a pH of about 6.5 to about 8.5.

28. The personal care formulation of claim 25 , wherein the salt of a compound of Formula (I) is present in the formulation in a concentration of about 0.1% by weight to about 10% by weight.

29. The composition of claim 4 , wherein the one or more additives is present.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2024
From: BURGO, ROCCO
To: INOLEX INVESTMENT CORPORATION
Reel/Frame 066177/0239 →
Continuity (4)
Division 15864887 · Jan 8, 2018
Continuation 14709344 · May 11, 2015
Provisional Application 61990983 · May 9, 2014
Related Publication 20220151885A1 · May 19, 2022
References Cited (29)
US 3937811A · Papantaniou et al. · 1976 [cited by applicant]
US 4216227A · Cook et al. · 1980 [cited by applicant]
US 4323694A · Scala, Jr. · 1982 [cited by applicant]
US 5560917A · Cohen et al. · 1996 [cited by applicant]
US 8039010B2 · Trogden et al. · 2011 [cited by applicant]
US 8105569B2 · Burgo · 2012 [cited by applicant]
US 8287844B2 · Burgo et al. · 2012 [cited by applicant]
US 20050013839A1 · Yamamoto et al. · 2005 [cited by applicant]
US 20110274641A1 · Burgo · 2011 [cited by applicant]
CN 102549138A · 2012 [cited by applicant]
EP 0847987A1 · 1998 [cited by applicant]
FR 2983403A1 · 2013 [cited by applicant]
JP 10168044H · 1998 [cited by applicant]
JP 2012532108A · 2012 [cited by applicant]
WO 2003105806A1 · 2003 [cited by applicant]
WO 2012172207A2 · 2012 [cited by applicant]
WO 2013150044A2 · 2013 [cited by applicant]
Cassiday, (Emulsions: making oil and water mix, Apr. 2014) (Year: 2014). [cited by examiner]
Vivian Y et al (J Drugs Dermatol. 2012;11(5):633-636 (Year: 2012). [cited by examiner]
Kanicky et al (Langmuir 2000, 16, 172-177) (Year: 2000). [cited by examiner]
Hrabalek et al (Pharmazie (1994), 49(5), 325-8: Pharat; ISSN: 0031-7144) (Year: 1994). [cited by examiner]
Duangjit et al (Int J Nanomedicine Apr. 29, 2014;9:2005-2017 (Year: 2017). [cited by examiner]
International Search Report, Intl. Publ. No. PCT/US2015/030215, dated Aug. 5, 2015, 4 pages. [cited by applicant]
International Preliminary Report or Patentability, Intl. Publ. No. PCT/US2015/030215, dated Nov. 15, 2016, 13 pages. [cited by applicant]
Decision to Grant a Patent from Japanese Patent Office for JP Application No. 2016-567018; mailing date of Apr. 21, 2021, 2 pages. [cited by applicant]
https://www.signaaldrich.com/life-science/metabolomics/learning-center/amino-acid-reference-chart.html by Millipore Sigma accessed on Nov. 5, 2020 (Year: 2020). [cited by applicant]
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4780292.htmhttps://www.chemicalbook.com/ChemicalProductProperty_EN_CB4780292.htm by Chemical Book, accessed on Nov. 5, 2020 (Year: 2020). [cited by applicant]
Kartashynska, Elena S., et al., “Relationship between the Bulk and Surface Basicity of Aliphatic Amines: A Quantum Chemical Approach”, ACS Omega 2020, 5, 32032-32039. [cited by applicant]
Vávrová, K., Hrabálek, A. (2015). Amino Acid-Based Transdermal Penetration Enhancers. In: Dragicevic, N., Maibach, H. (eds) Percutaneous Penetration Enhancers Chemical Methods in Penetration Enhancement. Springer, Berli… [cited by applicant]