Repellent fluorochemical compositions

• US 7,056,846 B2
• Filed: 12/04/2001
• Issued: 06/06/2006
• Est. Priority Date: 12/04/2001
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Jariwala, Chetan P., Clark, John C., Burleigh, Malcolm B., Zai-Ming, Qiu
• Primary Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US10/004,847
• Publication Number:
  US 20030136938A1
• Time in Patent Office: 1,645 Days
• Field of Search: 528/70, 528/391, 442/93, 442/94, 560/157, 560/351, 564/80, 106/287.27, 106/287.28, 106/287.3, 106/287.32
• US Class Current: 442/94
• CPC Class Codes: C08G 18/2885 containing halogen atoms
• CPC Class Codes: Y10T 442/2279 Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
• CPC Class Codes: Y10T 442/2287 Fluorocarbon containing

Abstract

This invention provides compositions and methods for treating fibrous substrates to render those substrates durably repellent to water and oil and durably resistant to dry soil comprising a fluorochemical urethane formed by reacting a tri- or higher order isocyanate with a fluorochemical monofunctional compound; and optionally a non-fluorinated aliphatic monofunctional compound.

Claims

1. A urethane composition consisting essentially of the reaction product of:

a. An aliphatic polyisocyanate having three or more isocyanate groups; and

b. A fluorochemical of the formula R_f—

SO₂N(R¹)—

R²-Z;

wherein R_f a perfluoroalkyl or perfluoroheteroalkyl group having from 3 to about 6 carbon atoms,

R¹ is a lower alkyl group,

R² is an alkylene or heteroalkylene group, and

Z is an isocyanate-reactive functional group, and

c. an aliphatic monofunctional compound, wherein said fluorochemical is in an amount sufficient to react with at least about 50% of the available isocyanate groups.

2. The composition of claim 1 wherein said aliphatic monofunctional compound is of the formula R′

″

-Z, wherein R′

″

is an aliphatic group and Z is an isocyanate-reactive functional group.

3. The composition of claim 2 comprising compounds of the formula

(R_f*)_nA(NHCO-Z′

R′

″

)<sub>m−

n</sub>,

wherein R_f* is R_f—

SO₂N(R¹)—

R²-Z′

,

Z′

is the residue of Z,

A is the residue of said aliphatic isocyanate, having valency m,

R′

″

is an aliphatic radical, and

n (average) is at least 1.5.

4. The composition of claim 1 wherein

R_f a fluorinated carbon chain having from 3 to about 6 carbon atoms,

R¹ is a —

H or —

CH₃,

R² is an alkylene group having 1 to 3 carbon atoms, and

Z is —

OH.

5. The composition of claim 2 wherein the amount of aliphatic monofunctional compound is in an amount sufficient to react with the remaining available isocyanate groups.

6. The composition of claim 2 wherein the amount of aliphatic monofunctional compound is in an amount sufficient to react with 15% or less of the available isocyanate groups.

7. The composition of claim 1 wherein the amount of fluorochemical is in an amount sufficient to react with 75% or more of the available isocyanate groups.

8. The composition of claim 1 wherein R_f is a perfluorinated alkyl group.

9. The composition of claim 1 further comprising a hydrophilic anti-staining compound.

10. The fibrous substrate treatment composition comprising the urethane composition of claim 1 and a solvent.

11. The treatment composition of claim 10 comprising from about 0.05 to 10 weight percent of the urethane composition.

12. A method for imparting stain-release characteristics to a fibrous substrate comprising the steps of:

(a) applying a treatment composition of claim 11, and.

(b) allowing the treatment composition to cure.

13. The method of claim 12 wherein said treatment composition is applied in an amount sufficient to provide between 0.05% and 3% solids on fiber.

14. The method of claim 13 wherein said composition is cured at ambient temperature.

15. An article comprising:

a fibrous substrate having a cured coating derived from at least one solvent and a

chemical composition of claim 1.

16. The composition of claim 1 further comprising a surfactant.