Fluorocarbon dermal protective compositions

• US 4,035,506 A
• Filed: 07/26/1974
• Issued: 07/12/1977
• Est. Priority Date: 07/26/1974
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Lucas, Anthony James, Degen, Peter John
• Primary Examiner(s): Drezin, Norman A.
• Application Number:
  US05/492,200
• Time in Patent Office: 1,082 Days
• Field of Search: 424/312, 424/303, 424/313
• US Class Current: 514/562
• CPC Class Codes: A61K 8/70 containing perfluoro groups, e.g. perfluoroethers
• CPC Class Codes: A61Q 17/00 Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
• CPC Class Codes: C07C 309/76 containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton

Abstract

Dermal protective compositions are disclosed which comprise a pharmaceutical extending medium having incorporated therein a substantive, dermally non-irritating compound which is a polyfunctional organic molecule containing one or more fluorocarbon-containing groups joined by one or more polar linking groups to a polyvalent organic radical. When applied to skin, these compositions provide repellency against a wide variety of dermal irritants and are resistant to removal by mild abrasion and/or detergent solutions.

Claims

1. In a dermal protective composition comprising a pharmaceutical extending medium and a protective amount of a fluorocarbon-containing active ingredient, the improvement comprising employing as said active ingredient a substantive dermally non-irritating compound of the formula ##STR92## wherein A is a polyvalent saturated or unsaturated, aliphatic or cycloaliphatic organic radical containing 8 to 108 carbon atoms;

Z'"'"' is --NH-- or --O--;

X is --(W)_d R_f where W is a bridging group free of isocyanate or isocyanate reactive groups, d is a zero or one, and R_f is a fluorinated, saturated, monovalent, aliphatic radical containing 3 to 20 carbon atoms in which the carbon atoms of the chain are substituted only by fluorine, chlorine or hydrogen atoms with no more than one hydrogen or chlorine atom for every two carbon atoms and the terminal carbon atom is perfluorinated, and in which a divalent oxygen or trivalent nitrogen atom, bonded only to carbon atoms can be present in the skeletal chain;

Y is --H, M^e+, or R¹ where R¹ is an aliphatic, cycloaliphatic or aromatic radical containing 1 to 24 carbon atoms;

M^e+ is a pharmaceutically acceptable organic or inorganic cation and

e is one, two or three;

n is an integer from 1 to 10 designating the same or different ##STR93## n'"'"' is zero or an integer from 1 to 9 designating the same or different ##STR94## n+n'"'"' = 2- 10;

said compound containing from 1 to 60 percent by weight of fluorine.

2. A composition according to claim 1 wherein W is selected from the group consisting of:

##STR95## where R² is H or an alkyl radical containing 1 to 8 carbons;

R³ is H, --CH₃ or --C₂ H₅,

m is an integer from 1 to 12.

m'"'"' is an integer from 2 to 12.

m" is an integer from 1 to 24.

3. In a dermal protective composition comprising a pharmaceutical extending medium and a protective amount of a fluorocarbon-containing active ingredient, the improvement comprising employing as said active ingredient a substantive, dermally non-irritating compound of the formula ##STR96## where A is a polyvalent saturated or unsaturated, aliphatic or cycloaliphatic organic radical containing 34 to 108 carbon atoms;

Z'"'"' is --NH-- or --O--;

X is ##STR97## R_f is a fluorinated, saturated, monovalent aliphatic radical containing from 3 to 20 carbon atoms in which the carbon atoms of the chain are substituted only by fluorine, chlorine or hydrogen atoms with no more than one hydrogen or chlorine atom for every two carbon atoms and the terminal carbon atom is perfluorinated, and in which a divalent oxygen or trivalent nitrogen atom, bonded only to carbon atoms, can be present in the skeletal chain;

m is an integer from 1 to 12;

R² is H or an alkyl radical containing 1 to 8 carbon atoms;

n is an integer from 1 to 10 designating the same or different ##STR98## n'"'"' is zero or an integer from 1 to 9;

said compound containing from 1 to 60 percent by weight of fluorine.

4. A composition according to claim 3 wherein X is ##STR99## where R² is --CH₃, --C₂ H₅, or --C₄ H₉, and m is an integer from 1 to 12.

5. In a dermal protective composition comprising a pharmaceutical extending medium and a protective amount of a fluorocarbon-containing active ingredient, the improvement comprising employing as said active ingredient a substantive, dermally non-irritating compound of the formula ##STR100## where A contains 34 carbon atoms and is the aliphatic portion of polymerized 18-carbon fatty acids.

6. In a dermal protective composition comprising a pharmaceutical extending medium and a protective amount of a fluorocarbon-containing active ingredient, the improvement comprising employing as said active ingredient a substantive, dermally non-irritating compound of the formula ##STR101## where A contains 34 carbon atoms and is the aliphatic portion of polymerized 18-carbon fatty acids.

7. In a dermal protective composition comprising a pharmaceutical extending medium and a protective amount of a fluorocarbon-containing active ingredient, the improvement comprising employing as said active ingredient a substantive, dermally non-irritating compound of the formula ##STR102## where A contains 34, 51, 68, 85 or 102 carbon atoms and is the aliphatic portion of polymerized 18-carbon fatty acids, and n is an integer from 2 to 6.

8. In a dermal protective composition comprising a pharmaceutical extending medium and a protective amount of a fluorocarbon-containing active ingredient, the improvement comprising employing as said active ingredient a substantive, dermally non-irritating compound of the formula ##STR103## where A contains 34 carbon atoms and is the aliphatic portion of polymerized 18-carbon fatty acids.