Oil and water repellent textile composition containing a fluorochemical polyurethane resin and a quaternary ammonium salt

• US 3,968,066 A
• Filed: 04/18/1974
• Issued: 07/06/1976
• Est. Priority Date: 04/18/1974
• Status: Expired due to Term

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Mueller, Karl Friedrich
• Primary Examiner(s): Rzucidlo, Eugene C.
• Application Number:
  US05/462,169
• Time in Patent Office: 810 Days
• Field of Search: 260/29.6 F, 260/29.2 TN, 260/DIG. 20, 260/29.6 MN, 260/77.5 AP, 117/139.5 A
• US Class Current: 524/236
• CPC Class Codes: C08G 18/3855 having sulfur

Abstract

The dry soil repellent properties of a fluorochemical textile resin useful to impart oil and water repellency to textiles can be improved by the presence of a quaternary ammonium salt containing a long hydrocarbon chain. The oil and water repellent properties are not adversely affected.

Claims

1. A composition comprising a fluorochemical polyurethane textile resin and from about 3 to about 100%, based on the weight of resin, of a quaternary ammonium salt containing at least one long hydrocarbon chain, wherein the fluorochemical polyurethane textile resin is of the formula ##EQU11## where R_f is perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms;

R¹ is straight or branched chain alkylene of 1 to 12 carbon atoms, or alkylenethioalkylene, alkyleneoxyalkylene of alkyleneiminoalkylene of 2 to 12 carbon atoms;

R" and R'"'"'" each independently is straight or branched chain alkylene of 1 to 12 carbon atoms or

space="preserve" listing-type="equation">C.sub.m H.sub.2m (OC.sub.k K.sub.2k).sub.r

where

m is 1 to 12,

k is 2 to 6,

r is 1 to 40, and

A is the divalent residue of an organic diisocyanate.

2. A composition according to claim 1 in which the quaternary ammonium salt has the formula ##EQU12## where R₁ is branched or straight chain alkyl of 8 to 21 carbon atoms;

phenylalkylene of 12 to 27 carbon atoms;

branched or straight chain alkenyl of 8 to 21;

or straight or branched chain alkadienyl of 8 to 21 carbon atoms;

R₂ is branched or straight chain alkyl of 1 to 21 carbon atoms;

phenylalkylene of 8 to 27 carbon atoms;

γ

-hydroxyalkyl of 2 to 4 carbon atoms;

branched or straight chain alkenyl or alkadienyl of 8 to 21 carbon atoms;

or the group of formula

space="preserve" listing-type="equation">(CH.sub.2 CH.sub.2 O).sub.x H

where

x is an integer from 1 to 25;

or

R₂ is alkylene of 1 to about 8 carbon atoms containing a quaternized nitrogen atom whose substituents are alkyl, phenylalkylene, γ

-hydroxyalkyl, alkenyl, alkadienyl or the group

space="preserve" listing-type="equation">(CH.sub.2 CH.sub.2 O).sub.n H

all as previously defined;

R₃ and R₄ are selected from the same group as R₂ with the further limitation that only one of R₂, R₃ and R₄ can be selected from the same group as R₁ ;

and

X^- is an anion ##SPC5##

where

R₁ and X^- are as defined above

a is an integer from 0 to 3

R is selected from hydrogen, alkyl of 1 to 4 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, halogen (Cl, Br, I, F) alkoxy of 1 to 4 carbon atoms, carboxyl, carbalkoxy of 2 to 4 carbon atoms, acetyl, benzyl, sulfo, carbamyl and cyano

and ##SPC6##

is pyridine, quinoline, isoquinoline, pyridazine or pyrimidine

or ##SPC7##

where

a, X^-, R, R₁ and R₃ are as previously defined and ##SPC8##

is imidazole, benzimidazole, morpholine, piperidine, pyrrolidine, pyrazine, indazole, pyrazole, indole and pyrrole.

3. A composition according to claim 2 in which the quaternary ammonium salt has the formula ##EQU13## where R₁ is branched or straight chain alkyl of 8 to 21 carbon atoms;

phenylalkylene of 12 to 27 carbon atoms;

branched or straight chain alkenyl of 8 to 21;

or straight or branched chain alkadienyl of 8 to 21 carbon atoms;

R₂, r₃ and R₄ are each independently alkyl of 1 to 4 carbon atoms, hydroxyalkyl of 2 to 4 carbon atoms or benzyl.

4. A composition according to claim 2 in which the quaternary ammonium salt has the formula ##EQU14## where R₁ is as defined

R₂ and R₃ are methyl and

R₄ is methyl or benzyl.

5. A composition according to claim 4 in which R₄ is methyl.

6. A composition of claim 1 further comprising water.