IP Library Granted Patent US 11,440,867
Granted Patent B2
US 11,440,867 · App. 16/389,694 · Granted Sep 13, 2022

Medical lubricant

Inventors: Alan Thomas Barker (Bloomington, IN); Thomas P. Clement (Bloomington, IN)
Assignee: KVI LLC
C07C55/22C07C53/00C07C55/02C07F9/062C10M105/32C10M137/04
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Quick Facts
Patent No.
US 11,440,867
App. No.
16/389,694
Granted
Sep 13, 2022
Kind
B2
Abstract

A medical lubricant may comprise a base oil. The medical lubricant can be used on a surgical device.

Claims (46)

1. A formulation for a lubricant comprising

a base oil comprising a compound of the formula I

wherein R 1 is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, or C 1 -C 6 alkynyl, wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, or C 1 -C 6 alkynyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 3 ;

R 2 is C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl, and wherein each hydrogen atom in C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 7 ; or a salt thereof;

a phospholipid; or a salt thereof; and

a salt of the formula

M 1 (R 8 )(R 9 )(calcium stearate)  (II)

wherein M 1 is a divalent cation, R 9 and R 8 are independently OC(O)C 10 -C 25 alkyl, − OC(O)C 10 -C 25 alkenyl, or—OC(O)C 10 -C 25 alkynyl, and wherein each hydrogen atom in C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 10 ,

wherein each of R 3 , R 7 , and R 10 is independently H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 10 -C 25 alkyl, C 10 -C 25 alkenyl, C 10 -C 25 alkynyl, —C(O)C 1 -C 6 alkyl, —C(O)C 1 -C 6 alkenyl, —C(O)C 1 -C 6 alkynyl, —C(O)C 10 -C 25 alkyl, —C(O)C 10 -C 25 alkenyl, —C(O)C 10 -C 25 alkynyl, wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 10 -C 25 alkyl, C 10 -C 25 alkenyl, C 10 -C 25 alkynyl, —C(O)C 1 -C 6 alkyl, —C(O)C 1 -C 6 alkenyl, —C(O)C 1 -C 6 alkynyl, —C(O)C 10 -C 25 alkyl, —C(O)C 10 -C 25 alkenyl, —C(O)C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, or amino, and further comprising a biocompatible fragrance that is at least 6 wt % of the formulation, the fragrance comprising an essential oil, hexyl acetate fructone ethyl methylphenylglycidate, or combinations thereof, wherein at least the base oil is at least 40% by weight of the formulation.

2. The formulation of claim 1 , wherein R 1 is H.

3. The formulation of claim 1 , wherein R 1 is C 1 -C 6 alkyl, and wherein each hydrogen atom in C 1 -C 6 alkyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 3 ; or a salt thereof.

4. The formulation of claim 1 , wherein R 1 is of the formula III

wherein each of R 14 and R 13 is independently C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl, wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 10 -C 25 alkyl, C 10 -C 25 alkenyl, and C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, or amino; and

* denotes a point of attachment.

5. The formulation of claim 1 , wherein R 7 is independently H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 10 -C 25 alkyl, C 10 -C 25 alkenyl, C 10 -C 25 alkynyl, and wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl, C 10 -C 25 alkyl, C 10 -C 25 alkenyl, and C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, or amino; or a salt thereof.

6. The formulation of claim 1 , wherein the base oil has a smoke point of at least 450° F., at least 475° F. at least 490° F. at least 500° F., or at least 510° F.

7. The formulation of claim 1 , wherein the fragrance is about 6% to about 25% by weight of the formulation.

8. The formulation of claim 1 , wherein compound of formula I is at least 20% by weight of the base oil.

9. The formulation of claim 1 , wherein the phospholipid has a structure according to formula II

wherein each of R 4 and R 5 is independently C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl, and wherein each hydrogen atom in C 10 -C 25 alkyl, C 10 -C 25 alkenyl, and C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 6 ;

wherein R 6 is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, or C 1 -C 6 alkynyl, and wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, and C 1 -C 6 alkynyl is independently optionally substituted with halo, hydroxy, or amino,

or a salt thereof.

10. The formulation of claim 1 , wherein the phospholipid or a salt thereof is at least 2% by weight of the formulation.

11. The formulation of claim 1 , wherein the salt of formula II is calcium stearate.

12. The formulation of claim 1 , further comprising a compound of formula V

wherein each of R 11 , R 12 , and R 13 is independently C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl, and wherein each hydrogen atom in C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 14 ;

wherein R 14 is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, or C 1 -C 6 alkynyl, wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, and C 1 -C 6 alkynyl is independently optionally substituted with a halo, hydroxy, or an amino, a long chain alcohol, a saturated fatty acid, a mixture thereof, or salts thereof.

13. A method of coating an electrocautery device with a formulation according to claim 1 , the method comprising

contacting a surface of an electrocautery device with the formulation according to claim 1 .

14. A method of preparing the formulation according claim 12 , comprising

heating a base oil,

mixing the base oil with a compound of formula V, and

mixing the base oil with a phospholipid.

15. The method of claim 14 , wherein the step of heating comprising heating the base oil to a temperature of about 120° F. to about 225° F.

16. The method of claim 14 , wherein the step of mixing the base oil with the compound of formula V occurs before the step of mixing the base oil with the phospholipid.

17. A kit comprising

a formulation for a lubricant according to claim 1 , and

a cautery probe.

18. A method of cauterization comprising

applying a formulation for a lubricant according to claim 1 to a cautery probe, and

cauterizing tissue with the cautery probe.

19. The formulation of claim 18 , wherein the triglyceride comprises a compound of formula V

wherein each of R 11 , R 12 , and R 13 is independently C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl, and wherein each hydrogen atom in C 10 -C 25 alkyl, C 10 -C 25 alkenyl, or C 10 -C 25 alkynyl is independently optionally substituted with halo, hydroxy, amino, oxo, or OR 14 ;

wherein R 14 is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, or C 1 -C 6 alkynyl, wherein each hydrogen atom in C 1 -C 6 alkyl, C 1 -C 6 alkenyl, and C 1 -C 6 alkynyl is independently optionally substituted with a halo, hydroxy, or an amino,

or a salt thereof.

20. The formulation of claim 19 , wherein the base oil is a vegetable oil.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2019
From: BARKER, ALAN THOMAS; CLEMENT, THOMAS P.
To: KVI LLC
Reel/Frame 048942/0275 →
Continuity (2)
Provisional Application 62667778 · May 7, 2018
Related Publication 20190337878A1 · Nov 7, 2019