# US 4,397,941 A · Dry nonelectroscopic toners for toning tacky image surfaces > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,397,941 A - Document ID: US4397941A - Status: Granted - Kind: A - Application number: 06/335,509 - Filed: 1981-12-29 - Granted: 1983-08-09 - Earliest claimed: 1980-11-07 - Assignees: E. I. Du Pont de Nemours and Company - Inventors: Michael G. Fickes - Web page: https://patentgrep.com/patent/US4397941A ## CPC - G03F 7/28: for obtaining powder images (G03F3/10 takes precedence) - Y10S 430/166: Toner containing - G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract Dry nonelectroscopic toners comprising pigmented organic resin particles having a size distribution of 0.2 to 30 micrometers, not more than 50 percent of the particles being less than 1 micrometer surface treated with a combination of at least 1% by weight of an antistatic agent and at least 0.5% of a slip agent as described. The preparation of the toners is described. The toners are useful in color developing positive and negative-working photosensitive elements particularly in an automatic toning machine. Improved clean-up and low stain propensity are achieved. ## Claims ### Claim 1 A dry nonelectroscopic toner comprising pigmented organic resin particles having a size distribution within the range of 0.2 to 30 micrometers and not more than 50 percent of the particles being less than 1 micrometer particle size, the improvement whereby the pigmented particles are surface coated with at least 1% by weight of an antistatic agent in combination with at least 0.5% by weight of slip agent selected from the class consisting of silicone oil having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 200 to 10,000; and fluorocarbon compounds having a weight average molecular weight of 500 to 500,000. ### Claim 2 (depends on 1) A toner according to claim 1 wherein the slip agent is polydimethylsiloxane or polymethyl(X)siloxane where X is an alkyl chain with 2 to 12 carbon atoms. ### Claim 3 (depends on 1) A toner according to claim 1 wherein the antistatic agent is an anionic antistatic agent. ### Claim 4 A dry nonelectroscopic toner comprising pigmented organic resin particles having a size distribution within the range of 0.2 to 30 micrometers and not more than 50 percent of the particles being less than 1 micrometer particle size, the improvement whereby the pigmented particles are surface coated with at least 1% by weight of an anionic antistatic agent which is a member taken from the group consisting of: (a) sodium alkyl benzene sulfonate wherein alkyl is an alkyl chain with 8 to 18 carbon atoms; (b) sodium alkyl sulfonate wherein alkyl is an alkyl chain with 10 to 20 carbon atoms; (c) secondary alkyl sulfate wherein one or both alkyl groups are substituted with functional groups taken from the group consisting of ester, ether, and alcohol, the alkyl being an alkyl chain of 1 to 18 carbon atoms; (d) phosphorous-containing compound of the formula (RO).sub.m P(O(OX).sub.n wherein R is an alkyl chain with 4 to 18 carbon atoms, X is an cation taken from the group consisting of H, K, Na, NH.sub.4, m is 1 or 2 and n is 2 or 1; and (e) amine salt of alkyl sulfate wherein alkyl is an alkyl chain of 8 to 18 carbon atoms and amine is taken from the group consisting of ammonia, diethyanolamine, triethanolamine and diethylcyclohexyl amine in combination with at least 0.5% by weight of slip agent selected from the class consisting of silicone oil having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 200 to 10,000; and fluorocarbon compounds having a weight average molecular weight of 500 to 500,000. ### Claim 5 (depends on 1) A toner according to claim 1 wherein the antistatic agent is a cationic antistatic agent. ### Claim 6 A dry nonelectroscopic toner comprising pigmented organic resin particles having a size distribution within the range of 0.2 to 30 micrometers and not more than 50 percent of the particles being less than 1 micrometer particle size, the improvement whereby the pigmented particles are surface coated with at least 1% by weight of a cationic antistatic agent which is a member taken from the group consisting of (a) alkyl trimethyl ammonium bromide wherein alkyl is an alkyl chain with 1 to 18 carbon atoms; and (b) Quaternary ammonium compounds of the formula: ##STR6## wherein R and R.sub.1 may be a saturated or unsaturated alkyl chain with 1 to 24 carbon atoms or mixtures thereof, R.sub.2 may be an alkyl chain of 1 to 24 carbon atoms or R.sub.3 wherein R.sub.3 is a polyether substituent of the formula --(CH.sub.2 CH.sub.2 O).sub.m --[CH.sub.2 CH(CH.sub.3)O].sub.n --H wherein m and n may be 0 to 20, the total of m and n being at least 1, and X is an anion taken from the group consisting of CH.sub.3 SO.sub.4, C.sub.2 H.sub.5 SO.sub.4, (CH.sub.3).sub.2 PO.sub.4, (C.sub.2 H.sub.5).sub.2 PO.sub.4 ; the total number of carbon atoms in R,R.sub.1 and R.sub.2 should not exceed 38 in combination with at least 0.5% by weight of slip agent selected from the class consisting of silicone oil having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 200 to 10,000; and fluorocarbon compounds having a weight average molecular weight of 500 to 500,000. ### Claim 7 (depends on 1) A toner according to claim 1 wherein the antistatic agent is an amphoteric antistatic agent. ### Claim 8 A dry nonelectroscopic toner comprising pigmented organic resin particles having a size distribution within the range of 0.2 to 30 micrometers and not more than 50 percent of the particles being less than 1 micrometer particle size, the improvement whereby the pigmented particles are surface coated with at least 1% by weight of an amphoteric antistatic agent which is taken from the class consisting of alkyl bis(polyethanoxy)-gamma-sulfopropyl betaine and alkyl bis(hydroxyethyl)-gamma-sulfopropyl betaine wherein alkyl is an alkyl chain with 12 to 24 carbon atoms and in the former the number of polyether units is 1 to 4 in combination with at least 0.5% by weight of slip agent selected from the class consisting of silicone oil having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 200 to 10,000; and fluorocarbon compounds having a weight average molecular weight of 500 to 500,000. ### Claim 9 (depends on 1) A toner according to claim 1 wherein the antistatic agent is a nonionic antistatic agent. ### Claim 10 A dry nonelectroscopic toner comprising pigmented organic resin particles having a size distribution within the range of 0.2 to 30 micrometers and not more than 50 percent of the particles being less than 1 micrometer particle size, the improvement whereby the pigmented particles are surface coated with at least 1% by weight of a nonionic antistatic agent which is a member taken from the group consisting of a compound of the formula: (a) R(OCH.sub.2 CH.sub.2).sub.n --OH wherein R is a saturated or unsaturated alkyl chain with 12 to 18 carbon atoms or CH.sub.3 (CH.sub.2).sub.7 --CH.dbd.CH(CH.sub.2).sub.8 --, and n is 2 to 10; (b) R(OCH.sub.2 CH.sub.2).sub.m [OCH.sub.2 CH(CH.sub.3)].sub.n --OH wherein R is an alkyl chain with 12 to 18 carbon atoms, m is 0 to 10 and n is 1 to 10; and (c) mono and diglycerides of carboxylic acids having an alkyl chain of 12 to 18 carbon atoms in combination with at least 0.5% by weight of slip agent selected from the class consisting of silicone oil having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 200 to 10,000; and fluorocarbon compounds having a weight average molecular weight of 500 to 500,000. ### Claim 11 (depends on 1) A toner according to claim 1 wherein the pigmented resin particles are comprised of cellulose acetate particles having pigment particles embedded in their surfaces. ### Claim 12 A process of preparing dry, nonelectroscopic surface coated toners from pigmented organic resin particles having a size distribution within the range of 0.2 to 30 micrometers and not more than 50 percent of the particles being less than 1 micrometer particle size which comprises adding in either order or simultaneously to the pigmented resin particles an antistatic agent and a slip agent selected from the class consisting of silicone oil having a weight average molecular weight of about 230 to 50,000; saturated hydrocarbons having a weight average molecular weight of about 200 to 10,000; and fluorocarbon compounds having a weight average molecular weight of about 500 to 500,000. ### Claim 13 (depends on 12) A process according to claim 12 wherein the antistatic agent is of the formula: R(OCH.sub.2 CH.sub.2)--OH wherein R is an alkyl chain with 12 to 18 carbon atoms or CH.sub.3 (CH.sub.2).sub.7 --CH.dbd.CH(CH.sub.2).sub.8 --, and n is 2 to 10. ### Claim 14 (depends on 12) A process according to claim 12 wherein the slip agent is polydimethylsiloxane or polymethyl(X)siloxane where X is an alkyl chain with 2 to 12 carbon atoms. ### Claim 15 (depends on 12) A process according to claim 12 wherein the pigmented resin particle are comprised of cellulose acetate particles having pigment particles embedded in their surfaces.