Fluroaliphatic dimer acid derivatives and use thereof

• US 6,171,983 B1
• Filed: 09/08/1999
• Issued: 01/09/2001
• Est. Priority Date: 11/12/1991
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Coppens, Dirk M., Grant, Richard J.
• Primary Examiner(s): Nakarani, D. S.
• Application Number:
  US09/391,540
• Time in Patent Office: 489 Days
• Field of Search: 106/2, 252/8.57, 252/8.62, 427/393.4, 428/151, 428/421, 428/422, 428/537.5, 428/540, 428/904, 442/79, 442/82, 442/88, 442/92
• US Class Current: 442/82
• CPC Class Codes: C04B 41/466 Halogenated compounds, e.g. perfluor-compounds
• CPC Class Codes: C04B 41/4842 Fluorine-containing polymers
• CPC Class Codes: C04B 41/4846 Perfluoro-compounds
• CPC Class Codes: C07C 311/09 the carbon skeleton being further substituted by at least two halogen atoms
• CPC Class Codes: C14C 9/00 Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
• CPC Class Codes: D21H 21/16 Sizing or water-repelling agents
• CPC Class Codes: Y10T 428/24438 Artificial wood or leather grain surface
• CPC Class Codes: Y10T 428/31993 Of paper
• CPC Class Codes: Y10T 428/4935 Impregnated naturally solid product [e.g., leather, stone, etc.]
• CPC Class Codes: Y10T 442/2164 Coating or impregnation specified as water repellent
• CPC Class Codes: Y10T 442/2189 Fluorocarbon containing
• CPC Class Codes: Y10T 442/2238 Fluorocarbon containing
• CPC Class Codes: Y10T 442/227 Fluorocarbon containing

Abstract

This invention relates to fluorochemical compositions, their preparation and their use as water- and oil-repellents, and substrates treated therewith. The fluorochemical composition comprises a mixture of fluorochemical compounds and/or polymers, each component having at least two fluoroaliphatic groups and a large hydrocarbon moiety such as derived from dimer acids, and the polymer having at least one fluoroaliphatic group and a plurality of said hydrocarbon moiety.

Claims

1. An article comprising a substrate having at least a portion of at least one surface thereof treated with a fluorochemical composition having an acid value of from 0 to about 20, comprising a mixture of normally solid compounds which are fluoroaliphatic esters of dimer acids and/or trimer acids, each of the compounds having at least two fluoroaliphatic groups and a hydrocarbon moiety of at least 30 carbon atoms or having at least one fluoroaliphatic group and a plurality of said hydrocarbon moiety;

to impart water and oil repellency thereto.

2. The article of claim 1 wherein said substrate is textile fabric, paper, carpet, leather or stone.

3. The article of claim 2 wherein said substrate is leather.

4. The article of claim 2 wherein said substrate is textile fabric.

5. The article of claim 1 wherein said hydrocarbon moiety comprises a monocycloaliphatic moiety with 6 ring carbon atoms or a bicycloaliphatic moiety with 10 ring carbon atoms.

6. The article of claim 1 wherein said mixture comprises said compounds which are fluoroaliphatic esters of dimer acids.

7. The article of claim 1 wherein said fluorochemical composition comprises a mixture of fluorochemicals represented by (R_f—

L—

P)_n—

A and/or {(R_f—

L—

P)_n—

A—

P}_m—

Z wherein

R_frepresents a fluoroaliphatic group;

L represents a covalent bond or an organic moiety that optionally contains oxygen-. nitrogen-, or sulfur-containing groups or a combination thereof;

A represents an aliphatic moiety with at least 30 carbon atoms;

P represents a carbonyloxy or oxycarbonyl moiety;

Z represents a mono- or multi-valent hydrocarbon or fluorocarbon moiety;

n represents an integer of about 2 to 10;

n′

represents an integer of about 1 to 10;

m represents an integer of about 1 to 5.

8. The article of claim 7 wherein A has 30 to 170 carbon atoms.

9. The articles of claim 7 wherein A has 51 carbon atoms.

10. The article of claim 7 wherein A has 34 carbon atoms.

11. The article of claim 7 wherein n is 3.

12. The article of claim 7 wherein R_fis a perfluorinated aliphatic group of formula C_xF₂₊₁ and x is at least 3.

13. The article of claim 7 wherein L is alkylene, sulfonamido or sulfonamidoalkylene.

14. The article of claim 7 wherein the aliphatic moiety A is derived from a polymerized fatty acid prepared from unsaturated fatty acids selected from the group consisting of palmitoleic acid, linoleic acid, linolenic acid, oleic acid, ricinoleic acid, gadoleic acid, erucic acid, or mixtures thereof.

15. The article of claim 7 wherein said mixture comprises a mixture of esters made from fully esterifying dimer acids with N-methyl-perfluorooctylsulfonamidoethyl alcohol.

16. A method for imparting water and oil repellency to a substrate comprising the step of treating at least a portion of at least one surface of said substrate with a fluorochemical composition having an acid value of from 0 to about 20, comprising a mixture of normally solid compounds which are fluoroaliphatic esters of dimer acids and/or trimer acids, each of the compounds having at least two fluoroaliphatic groups and a hydrocarbon moiety of at least 30 carbon atoms or having at least one fluoroaliphatic group and a plurality of said hydrocarbon moiety.

17. The method of claim 16 wherein said substrate is textile fabric, paper, carpet, leather, or stone.