IP Library Granted Patent US 10,246,573
Granted Patent B2
US 10,246,573 · App. 15/423,061 · Granted Apr 2, 2019

Anti-static compositions

Inventors: Bogdan-Catalin Serban (Bucharest, RO); Cornel P. Cobianu (Bucharest, RO); Octavian Buiu (Bucharest, RO); Mihai Brezeanu (Bucharest, RO); Alisa Stratulat (Bucharest, RO); Viorel Georgel Dumitru (Prahova, RO); Andrea Piesker (Hessen, DE); Christiane Saunier (Auten, FR); Eric Farin (Paris, FR)
Assignee: HONEYWELL INTERNATIONAL INC.
C08K5/42A41D19/0082B05D5/12B29C41/003B29C41/14B29C41/42B29D99/0067C08G73/0266C08L79/02C09K3/16H01B1/128H05F1/00A41D19/0058B29K2079/00B29K2105/0026B29K2105/0038B29L2031/4864C08K2201/001C08K2201/017
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Quick Facts
Patent No.
US 10,246,573
App. No.
15/423,061
Granted
Apr 2, 2019
Kind
B2
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 R 2 is chosen from substituted or unsubstituted (C 1 -C 10 )hydrocarbyl- and substituted or unsubstituted (C 1 -C 10 )hydrocarbyl-O—, L 1 is substituted or unsubstituted (C 1 -C 10 )hydrocarbylene, L 2 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 (71)

1. A doped polyaniline comprising a dopant that is:

a polymer comprising

a compound having the structure:

 or a salt thereof,

wherein

R 2 is chosen from substituted or unsubstituted (C 1 -C 10 )hydrocarbyl- and substituted or unsubstituted (C 1 -C 10 )hydrocarbyl-O—,

L 1 is substituted or unsubstituted (C 1 -C 10 )hydrocarbylene,

L 2 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.

2. 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.

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

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

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

6. 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 M n 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 R 1 is chosen from —H and —CH 3 ;

a cyclodextrin sulfate, or salts thereof;

or comprises combinations thereof.

7. 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.

8. 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.

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

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 R 2 is chosen from substituted or unsubstituted (C 1 -C 10 )hydrocarbyl- and substituted or unsubstituted (C 1 -C 10 )hydrocarbyl-O—, L 1 is substituted or unsubstituted (C 1 -C 10 )hydrocarbylene, L 2 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.

11. 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.

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

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

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

15. 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.

16. 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.

17. 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.

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

19. 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 M n 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 R 1 is chosen from —H and —CH 3 ;

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.

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 R 1 is chosen from —H and —CH 3 ;

a compound having the structure:

 or a salt thereof,

wherein

R 2 is chosen from substituted or unsubstituted (C 1 -C 10 )hydrocarbyl- and substituted or unsubstituted (C 1 -C 10 )hydrocarbyl-O—,

L 1 is substituted or unsubstituted (C 1 -C 10 )hydrocarbylene,

L 2 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.

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

22. 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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2025
From: HONEYWELL INTERNATIONAL INC.
To: HONEYWELL SAFETY PRODUCTS USA, INC.
Reel/Frame 070538/0643 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2017
From: SAUNIER, CHRISTIANE; FARIN, ERIC; PIESKER, ANDREA; SERBAN, BOGDAN-CATALIN; COBIANU, CORNEL P.; BUIU, OCTAVIAN; BREZEANU, MIHAI; STRATULAT, ALISA; DUMITRU, VIOREL GEORGEL
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 041160/0767 →
Priority Claims (1)
EP 16153979 · Feb 2, 2016 · regional
Continuity (1)
Related Publication 20170218179A1 · Aug 3, 2017