Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates

• US 20040024262A1
• Filed: 04/17/2003
• Published: 02/05/2004
• Est. Priority Date: 05/11/1999
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Eggleston, James D, Yandrasits, Michael A, Coppens, Dirk M, Jariwala, Chetan P, Dams, Rudolf
• Granted Patent: US 7,049,379 B2
• Time in Patent Office: Days
• US Class Current: 568/677
• CPC Class Codes: C14C 9/00 Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
• CPC Class Codes: D06M 15/277 containing fluorine
• CPC Class Codes: D06M 2200/11 Oleophobic properties
• CPC Class Codes: D06M 2200/12 Hydrophobic properties

Abstract

This invention provides a method of treating fibrous substrates, such as leather, by contacting the substrate with a fluorochemical compound comprising: a fluorochemical oligomeric portion comprising an aliphatic backbone with a plurality of pendant fluoroaliphatic groups, each fluoroaliphatic group having a fully fluorinated terminal group and each independently linked to a carbon atom of the aliphatic backbone through an organic linking group; an aliphatic moiety; and a linking group which links the fluorochemical oligomeric portion to the aliphatic moiety. The fluorochemical compounds provide desirable oil, water and stain repellency to fibrous substrates.

Claims

1. A method of treating fibrous substrates comprising contacting the fibrous substrate with composition comprising an aikylated fluorochemical oligomeric compound comprising:

(i) at least one fluorochemical oligomeric portion comprising an aliphatic backbone with a plurality of fluoroaliphatic groups attached thereto, each fluoroaliphatic group having a fully fluoridated terminal group and each independently linked to a carbon atom of the aliphatic backbone through an organic linking group;

(ii) at least one aliphatic moiety; and

(iii) a linking group which links the fluorochemical oligomeric portion to the aliphatic moiety.

2. The method of claim 1 wherein said an alkylated fluorochemical oligomeric compound comprises:

(i) at least one oligomeric portion having both fluoroaliphatic and fluorine-free aliphatic pendent groups;

(ii) at least one aliphatic moiety; and

(iii) a linking group which links the oligomeric portion to the aliphatic moiety.

3. The method of claim 1 wherein said fluorochemical compounds are selected from the group consisting of:

[(A)_m−

L]_nR and (A)_m[L−

R]_n,

wherein m is 1 to 4 inclusive;

n is 1 to 4 inclusive;

each L independently comprises a linking group;

R is an organic aliphatic moiety; and

A is a fluorochemical oligomeric portion of the formula;

wherein

a is a number such that A is oligomeric and comprises a plurality of R_f groups;

each R₁ is independently hydrogen, halogen, or straight chain or branched chain alkyl containing 1 to about 4 carbon atoms;

each R₂ is independently hydrogen or straight chain or branched chain alkyl containing 1 to about 4 carbon atoms;

each Q is a covalent bond or an organic linking group;

R_f is a fluoroaliphatic group;

X is a hydrogen atom or a group derived from a free radical initiator.

4. The method of claim 2 wherein said fluorochemical compounds are selected from the group consisting of:

[(A)_m−

L]_nR and (A)_m[L−

R]_n,

wherein m is 1 to 4 inclusive;

n is 1 to 4 inclusive;

each L independently comprises a linking group;

R is an organic aliphatic moiety; and

A is a fluorochemical oligomeric portion of the formula

wherein the sum of a+b is a number such that A is oligomeric,

each R₁ independently is hydrogen, halogen, or straight chain or branched chain alkyl containing 1 to about 4 carbon atoms;

each R₂ is independently hydrogen or straight chain or branched chain alkyl containing 1 to about 4 carbon atoms;

Q and Q′

are each independently a covalent bond or an organic linking group,

R_f is a fluoroaliphatic group; and

R_h is a fluorine-free aliphatic group;

5. The method of claim 3 wherein a is 2 to 25.

6. The method of claim 4 wherein the sum of a+b is 2 to 25.

7. The method of claims 3 or 4 wherein R_f contains 3 to 20 carbon atoms.

8. The method according to any of claims 1 to 7 wherein said composition is in the form of an aqueous dispersion, an aqueous emulsion or a solution in an organic solvent

9. The method any of claims 1 to 8 wherein said substrate is leather.

10. The method according to claim 9 wherein said leather is contacted with said aqueous dispersion during wet-end processing.

11. The method according to claims 3 or 4 wherein at least one of said R and R_h groups has 8 or more carbon atoms.

12. A treated fibrous substrate prepared according to the method of any of claims 1-8.