# US 10,246,573 B2 · Anti-static compositions

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- Number: US 10,246,573 B2
- Document ID: US10246573B2
- Status: Granted
- Kind: B2
- Application number: 15/423,061
- Filed: 2017-02-02
- Published: 2017-08-03
- Granted: 2019-04-02
- Earliest claimed: 2016-02-02
- Assignees: Honeywell International Inc.
- Applicants: Honeywell International Inc.
- Inventors: Bogdan-Catalin Serban; Cornel P. Cobianu; Octavian Buiu; Mihai Brezeanu; Alisa Stratulat; Viorel Georgel Dumitru; Andrea Piesker; Christiane Saunier; Eric Farin
- Web page: https://patentgrep.com/patent/US10246573B2

## CPC

- C08K 5/42: Sulfonic acids; Derivatives thereof
- A41D 19/0082: {Details}
- B05D 5/12: to obtain a coating with specific electrical properties
- B29C 41/003: {characterised by the choice of material}
- B29C 41/14: Dipping a core {(B29C41/10 takes precedence)}
- B29C 41/42: Removing articles from moulds, cores or other substrates {(B29C33/444 and B29C37/0017 take precedence)}
- B29D 99/0067: {Gloves}
- C08G 73/0266: {Polyanilines or derivatives thereof}
- C08L 79/02: Polyamines
- C09K 3/16: Anti-static materials
- H01B 1/128: {comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes}
- H05F 1/00: Preventing the formation of electrostatic charges
- A41D 19/0058: {Three-dimensional gloves}
- B29K 2079/00: Use of polymers having nitrogen, with or without oxygen or carbon only, in the main chain {, not provided for in groups B29K2061/00 - B29K2077/00}, as moulding material
- B29K 2105/0026: {Flame proofing or flame retarding agents}
- B29K 2105/0038: {Plasticisers}
- B29L 2031/4864: {Gloves}
- C08K 2201/001: Conductive additives
- C08K 2201/017: Additives being an antistatic agent
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- A41D: OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})
- H05F: STATIC ELECTRICITY; NATURALLY-OCCURRING ELECTRICITY
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES

## Abstract

Various embodiments disclosed relate to anti-static compositions and gloves made from the same. In various embodiments, the present invention provides a doped polyaniline comprising a dopant that is a polyacrylic acid; a polymethacrylic acid; a sulfonatocalixarene; a cyclodextrin sulfate; a compound having the structure: wherein R2 is chosen from substituted or unsubstituted (C1-C10)hydrocarbyl- and substituted or unsubstituted (C1-C10)hydrocarbyl-O—, L1 is substituted or unsubstituted (C1-C10)hydrocarbylene, L2 is chosen from a bond, —O—, —O—C(O)—, and —NH—C(O)—, and n is about 1 to about 100,000; a salt thereof; or a combination thereof.

## Claims

### Claim 1

A doped polyaniline comprising a dopant that is:
a polymer comprising
a compound having the structure:
or a salt thereof,
wherein
R2 is chosen from substituted or unsubstituted (C1-C10)hydrocarbyl- and substituted or unsubstituted (C1-C10)hydrocarbyl-O—,
L1 is substituted or unsubstituted (C1-C10)hydrocarbylene,
L2 is chosen from a bond, —O—, —O—C(O)—, and —NH—C(O)—, and
n is about 1 to about 100,000;
p-sulfonatocalix[n]arene or a salt thereof, wherein n is an even integer that is from 10 to about 100;
or
a combination thereof.

### Claim 2 (depends on 1)

The doped polyaniline of claim 1, wherein the doped polyaniline comprises a repeating group having the structure:
wherein A− is the conjugate base of the dopant, the dopant having the structure A-H or a salt thereof.

### Claim 3 (depends on 1)

The doped polyaniline of claim 1, wherein the dopant is hygroscopic.

### Claim 4 (depends on 1)

The doped polyaniline of claim 1, wherein the doped polyaniline is conductive.

### Claim 5 (depends on 4)

The doped polyaniline of claim 4, wherein the doped polyaniline has a conductivity of about 10−10 S/cm to about 10 S/cm.

### Claim 6 (depends on 1)

The doped polyaniline of claim 1, wherein the dopant is the compound which comprises 2-[2-(2-methoxyethoxy)ethoxy]acetic acid, methoxypolyethylene glycol 5,000 acetic acid, methoxypolyethylene glycol 5,000 propionic acid, O-(2-carboxyethyl)-O′-methyl-undecaethylene glycol, O-methyl-O′-succinylpolyethylene glycol 2,000, O-methyl-O′-succinylpolyethylene glycol 5,000, O-[2-(3-succinylamino)ethyl]-O′-methyl-polyethylene glycol having an Mn of about 20,000;
or wherein the dopant further comprises a polymer comprising a repeating unit that has the structure:
or a salt thereof,
wherein R1 is chosen from —H and —CH3;
a cyclodextrin sulfate, or salts thereof;
or comprises combinations thereof.

### Claim 7 (depends on 1)

The doped polyaniline of claim 1, wherein the dopant further comprises p-sulfonatocalix[4]arene, p-sulfonatocalix[6]arene, p-sulfonatocalix[8]arene, a salt thereof, or a combination thereof.

### Claim 8 (depends on 1)

The doped polyaniline of claim 1, wherein the dopant further comprises alpha cyclodextrin sulfate, beta cyclodextrin sulfate, gamma cyclodextrin sulfate, a salt thereof, or comprises a combination thereof.

### Claim 9 (depends on 1)

The doped polyaniline of claim 1, wherein the dopant is about 40 wt % to about 60 wt % of the polyaniline.

### Claim 10

A vulcanized product comprising:
a composition comprising:
a doped polyaniline comprising a dopant that is:
a compound having the structure:
or a salt thereof
wherein R2 is chosen from substituted or unsubstituted (C1-C10)hydrocarbyl- and substituted or unsubstituted (C1-C10)hydrocarbyl-O—, L1 is substituted or unsubstituted (C1-C10)hydrocarbylene, L2 is chosen from a bond, —O—, —O—C(O)—, and —NH—C(O)—, and n is about 1 to about 100,000;
p-sulfonatocalix[n]arene or a salt thereof, wherein n is an even integer that is from 10 to about 100;
or
a combination thereof; and
a resin, wherein the composition is exposed to conditions sufficient to vulcanize the composition to form the vulcanized product.

### Claim 11 (depends on 10)

The vulcanized product of claim 10, wherein the doped polyaniline comprises a repeating group having the structure:
wherein A− is the conjugate base of the dopant, the dopant having the structure A-H or a salt thereof.

### Claim 12 (depends on 10)

The vulcanized product of claim 10, wherein the doped polyaniline is about 5 wt % to about 10 wt % of the composition.

### Claim 13 (depends on 10)

The vulcanized product of claim 10, wherein the resin is about 85 wt % to about 95 wt % of the composition.

### Claim 14 (depends on 10)

The vulcanized product of claim 10, wherein the resin is a natural rubber, a synthetic rubber, a polymer, or a combination thereof.

### Claim 15 (depends on 10)

The vulcanized product of claim 10, wherein the resin is polyvinyl chloride (PVC), chlorinated polyvinyl chloride (CPVC), polyvinyl alcohol, natural rubber, natural latex, a polyolefin, nitrile rubber, nitrile latex, chloroprene latex, butyl latex, fluoric latex, polyurethane, polychloroprene rubber, butyl rubber, fluorine rubber, a combination thereof, or a material curable to form any one of the foregoing.

### Claim 16 (depends on 10)

The vulcanized product of claim 10, wherein the composition further comprises a flame retardant, a plasticizer, a lubricant, an antimicrobial agent, or a combination thereof.

### Claim 17 (depends on 10)

The vulcanized product of claim 10, wherein the product is formed by dipping a hand-shaped former into the composition, prior to exposing the composition to conditions sufficient to vulcanize the composition.

### Claim 18 (depends on 10)

The product of claim 10, wherein the vulcanized product is a glove.

### Claim 19 (depends on 10)

The vulcanized product of claim 10, wherein the dopant is the compound which comprises 2-[2-(2-methoxyethoxy) ethoxy]acetic acid, methoxypolyethylene glycol 5,000 acetic acid, methocypolyethylene glycol 5,000 propionic acid, O-(2-carboxyethyl)-O′-methyl-undecaethylene glycol, O-methyl-O′-succinylpolyethylene glycol 2,000, O-methyl-O′-succinylpolyethylene glycol 5,000, O-[2-(3-succinylamino)ethyl]-O′-methyl-polyethylene glycol having an Mn of about 20,000;
or wherein the dopant further comprises a polymer comprising a repeating unit that has the structure:
or a salt thereof,
wherein R1 is chosen from —H and —CH3;
or wherein the dopant further comprises p-sulfonatocalix[4]arene, p-sulfonatocalix[6]arene, p-sulfonatocalix[8]arene, a cyclodextrin sulfate, or salts thereof;
or comprises combinations thereof.

### Claim 20

A method of making a glove, the method comprising:
making a doped polyaniline composition by doping an emeraldine free base with a dopant that is:
a polymer comprising a repeating unit that has the structure:
or a salt thereof,
wherein R1 is chosen from —H and —CH3;
a compound having the structure:
or a salt thereof,
wherein
R2 is chosen from substituted or unsubstituted (C1-C10)hydrocarbyl- and substituted or unsubstituted (C1-C10)hydrocarbyl-O—,
L1 is substituted or unsubstituted (C1-C10)hydrocarbylene,
L2 is chosen from a bond, —O—, —O—C(O)—, and —NH—C(O)—, and
n is about 1 to about 100,000;
a sulfonatocalixarene, or a salt thereof;
a cyclodextrin sulfate, or a salt thereof; or
a combination thereof; and
dipping a hand-shaped former into the doped polyaniline composition to form a coated hand-shaped former;
exposing the coated hand-shaped former to conditions sufficient to vulcanize the composition to form a glove; and
removing the glove from the hand-shaped former.

### Claim 21 (depends on 20)

The method of claim 20, wherein making a doped polyaniline composition includes adding a resin to the doped polyaniline.

### Claim 22 (depends on 20)

The method of claim 20, wherein making a doped polyaniline composition includes adding to the doped polyaniline at least one of a flame retardant, a plasticizer, a lubricant, or an antimicrobial agent.