Composition and method for treating substrates to reduce electrostatic charge and resultant article

• US 5,478,486 A
• Filed: 11/18/1993
• Issued: 12/26/1995
• Est. Priority Date: 11/18/1993
• Status: Expired due to Fees

• Current Assignee: Cognis Corporation (BASF SE)
• Original Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Inventors: Incorvia, Michael J.
• Primary Examiner(s): GREEN, ANTHONY J
• Application Number:
  US08/154,665
• Time in Patent Office: 768 Days
• Field of Search: 252/8.6, 252/8.8, 252/500, 562/605, 570/134, 570/136, 564/291, 57/901, 524/910, 524/911
• US Class Current: 252/8.61
• CPC Class Codes: C07C 217/50 Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
• CPC Class Codes: C07C 53/18 containing fluorine
• CPC Class Codes: C07C 53/21 containing fluorine
• CPC Class Codes: C08J 2471/00 Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/044 Forming conductive coatings; Forming coatings having anti-static properties
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 2201/04 Antistatic
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C09K 3/16 Anti-static materials
• CPC Class Codes: D06M 13/17 Polyoxyalkyleneglycol ethers
• CPC Class Codes: D06M 13/236 containing halogen atoms
• CPC Class Codes: D06M 13/33 containing halogen atoms
• CPC Class Codes: D06M 13/463 derived from monoamines
• CPC Class Codes: D06M 2200/00 Functionality of the treatment composition and/or properties imparted to the textile material
• CPC Class Codes: H01B 1/122 Ionic conductors
• CPC Class Codes: Y10S 524/91 Antistatic compositions
• CPC Class Codes: Y10S 524/911 Composition to apply to a substrate to be destaticized
• CPC Class Codes: Y10S 57/901 Antistatic
• CPC Class Codes: Y10T 428/2967 Synthetic resin or polymer
• CPC Class Codes: Y10T 428/2969 : Polyamide, polyimide or polyester
• CPC Class Codes: Y10T 442/2459 : Nitrogen containing

Abstract

Antistatic agents and their use in processing textiles or formed plastic substrates. The antistatic agent comprises a compound having a fluorocarbon moiety and an ethoxylated quaternary ammonium moiety. The antistatic composition increases the electrolytic conductivity of treated textile or plastic materials, thereby increasing the rate of electrostatic charge dissipation thereof. The antistatic agents remain effective after exposure of the treated substrate to an aqueous environment.

Claims

1. An antistatic agent of the formula Q--L--(R--X)_d, wherein Q represent a normal or branched, saturated or unsaturated perfluoroaliphatic radical, L represents an ester or an ether linkage, R represents an alkylene-oxyalkylene or an alkylene-poly(oxyalkylene) group, and X represents at least one quaternary ammonium group of the formula ##STR8## and, optionally, a tertiary amine group of the formula ##STR9## wherein R₁ and R₄ independently represent --(C₂ H₄ O)_f --Z, Z being H, Q or ##STR10## wherein Q is as defined above, f being an integer from 1 to 50, R₂ represents a C₁ -C₄ alkyl group, R₃ and R₅ independently represent a normal or branched, saturated or unsaturated C₆ -C₂₂ aliphatic group, A represents an organic or inorganic anion and d is 1 or 2.

2. An antistatic agent as claimed in claim 1 comprising an ester having as its reactive components at least one saturated perfluoroaliphatic carboxylic acid and at least one quaternary ammonium compound of the formula ##STR11## wherein g and k may be the same or different and are each integers from 1 to 50, j is an integer from 1 to 4, R₆ represents a normal or branched, saturated or unsaturated C₆ -C₂₂ aliphatic group, and A is an organic or inorganic anion and, optionally, a tertiary amine of the formula ##STR12## wherein m and n may be the same or different and are each integers from 1 to 50 which may be the same or different, R₇ represents a normal or branched, saturated or unsaturated, C₆ -C₂₂ aliphatic group;

said agent also including any of said reactive components in unreacted form.

3. An antistatic agent as claimed in claim 2 comprising an ester having as its reactive components at least one acid of the formula (C_q F_2q+1)--COOH, wherein q represents an integer from 1-17, at least one quaternary ammonium compound of the formula ##STR13## wherein s and w may be the same or different and are each integers from 2-16;

t is 1 or 2;

R₈ represents a normal or branched, saturated or unsaturated C₆ -C₁₈ aliphatic group;

A represents an anion selected from the group consisting of halide and sulfate, and at least one tertiary amine of the formula ##STR14## wherein y and z may be the same or different and are nominally 8;

R₉ represents a normal or branched, saturated or unsaturated, C₆ -C₁₈ aliphatic group;

said agent also including any of said reactive components in unreacted form.

4. An antistatic agent as claimed in claim 2 comprising an ester having as its reactive components trifluoroacetic acid, at least one quaternary ammonium compound selected from the group consisting of bis(polyethoxy ethanol) tallow ammonium salt;

methyl bis(polyethoxy ethanol) coco ammonium salt and polyethoxy coco ether amine diethylsulfate ammonium salt and at least one tertiary amine selected from the group consisting of bis(polyethoxy ethanol) tallow amine and bis(polyethoxy ethanol) coco amine, said agent also including any of said reactive components in unreacted form.

5. An antistatic composition comprising the product of the reaction between at least one normal or branched, saturated perfluoroaliphatic carboxylic acid and at least one quaternary ammonium compound of the formula ##STR15## wherein g and k may be the same or different and are each integers from 1 to 50, which may be the same or different, j is an integer from 1 to 4, R₆ represents a normal or branched, saturated or unsaturated C₆ -C₂₂ aliphatic group, and A is an organic or inorganic anion, and, optionally, a tertiary amine of the formula ##STR16## wherein m and n may be the same or different and are each integers from 1 to 50 which may be the same or different, and R₇ represents a normal or branched, saturated or unsaturated, C₆ -C₂₂ aliphatic group;

and any of said acid, said quaternary ammonium compound, or said tertiary amine in unreacted form.

6. A composition as claimed in claim 5 which further includes a vehicle for incorporation of said reaction product into a static-prone substrate.

7. A composition as claimed in claim 5, wherein said acid is of the formula (C_q F_2q+1)--COOH, wherein q represents an integer from 1-17, said quaternary ammonium compound is of the formula ##STR17## wherein s and w may be the same or different and are each integers from 2-16;

t is 1 or 2;

R₈ represents a normal or branched, saturated or unsaturated C₆ -C₁₈ aliphatic group;

A represents an anion selected from the group consisting of halide and sulfate, and said tertiary amine is of the formula ##STR18## wherein y and z may be the same or different and are each integers from 2-16; and

R₉ represents a normal or branched, saturated or unsaturated, C₆ -C₁₈ aliphatic group.

8. A composition as claimed in claim 5, wherein said acid is trifluoroacetic acid, said quaternary ammonium compound is selected from the group consisting of bis(polyethoxy ethanol) tallow ammonium salt;

methyl bis(polyethoxy ethanol) coco ammonium salt; and

polyethoxy coco ether amine diethylsulfate ammonium salt, and said tertiary amine is selected from the group consisting of bis(polyethoxy ethanol) tallow amine and bis(polyethoxy ethanol) coco amine.