# US 5,707,554 A · Electrically conductive surface release polymers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,707,554 A - Document ID: US5707554A - Status: Granted - Kind: A - Application number: 08/646,602 - Filed: 1996-05-08 - Granted: 1998-01-13 - Earliest claimed: 1996-05-08 - Assignees: Rexam Graphics Inc. - Inventors: Everett Wyman Bennett; Weitong Shi - Web page: https://patentgrep.com/patent/US5707554A ## CPC - C08F 246/00: Copolymers in which the nature of only the monomers in minority is defined - H01B 1/122: {Ionic conductors} - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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}) ## Abstract A polymeric material which is both electrically conductive, possesses surface release properties and can be formed into high-gloss, visually transparent coatings; is polymerized from a liquid mixture of three free radical, addition polymerizable materials by radiation induced polymerization. The liquid mixture contains: 1 to 80 weight parts of an ethylenically unsaturated, quaternary ammonium precursor; 0.1 to 10 weight parts of an ethylenically unsaturated, organo-silicone precursor; and, 5 to 95 weight parts of a multifunctional precursor containing at least two ethylenically unsaturated groups, which is a multifunctional monomeric material, an oligomeric material or a combination thereof. Optionally, the liquid mixture may contain up to 60 weight parts of an ethylenically unsaturated acidic precursor and up to 50 weight parts of one other monofunctional precursor containing one ethylenically unsaturated group. By adjusting concentrations of the three polymerizable components, surface conductivity can be varied over a wide range from an electrical resistance of 10.sup.5 ohm/.quadrature. to 10.sup.12 ohm/.quadrature., without adversely affecting surface release characteristics. Such tailored co-polymers may be used as coatings, fibers or other solid shapes and are useful as electrically conductive release coatings in electrographic and electrostatic imaging materials; and as antistatic coatings for sheet or fiber products which further require protective surface release for easy removal of laminate components, markings, stains, dirt and the like. ## Claims ### Claim 1 An electrically conductive polymeric release material comprising a polymer which comprises in polymerized form, A) 1 to 80 weight parts of a polymerizable, ethylenically unsaturated ammonium precursor; B) 0.1 to 10 weight parts of a polymerizable, ethylenically unsaturated, organo-silicone precursor; C) 5 to 95 weight parts of a multifunctional polymerizable precursor containing at least two polymerizable, ethylenically unsaturated functional groups, wherein the multifunctional polymerizable precursor is a multifunctional monomeric material, an oligomeric material or a combination thereof; D) 0 to 60 weight parts of a polymerizable, ethylenically unsaturated acidic precursor containing at least one carboxylic acid group; and E) 0 to 50 weight parts of an other monofunctional precursor containing one polymerizable, ethylenically unsaturated functional group; wherein the polymer has a surface having an electrical resistance between about 1.times.10.sup.5 ohm/.quadrature. and 1.times.10.sup.12 ohm/.quadrature.. ### Claim 2 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the ammonium precursor contains a cation selected from the group consisting of (3-(methacryloylamino)propyl)trimethylammonium, (2-(methacryloyloxy)-ethyl)trimethylammonium, (2-(acryloyloxy)-ethyl)trimethylammonium, (2-(methacryloyloxy)-ethyl)-methyldiethylammonium, 4-vinylbenzyltrimethylammonium, dimethyldiallylammonium and mixtures thereof. ### Claim 3 (depends on 2) The electrically conductive polymeric material of claim 2 wherein the ammonium precursor is 2-(acryloyloxy)ethyltrimethylammonium chloride. ### Claim 4 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the ammonium precursor has one of the structures: ##STR3## wherein R.sub.1 is H, methyl, or ethyl; Y is O or --NR.sub.3 wherein R.sub.3 is H or a C.sub.1 -C.sub.4 alkyl; m is an integer from 1 to 4, each R.sub.2 individually is a C.sub.1 -C.sub.4 alkyl group; and ›X!.sup.- is an anion. ### Claim 5 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the polymerizable, ethylenically unsaturated, organo-silicone precursor is an acrylated silicone. ### Claim 6 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the polymerizable, ethylenically unsaturated, organo-silicone precursor is an acrylated-oxyalkylene-silicone precursor wherein the alkylene is ethylene, propylene or a combination thereof. ### Claim 7 (depends on 6) The electrically conductive polymeric material of claim 6 wherein the polymerizable, ethylenically unsaturated, organo-silicone precursor additionally contains an acrylated-silicone precursor. ### Claim 8 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the multifunctional monomeric material is selected from the group consisting of trimethylolpropanetriacrylate, pentaerythritoltriacrylate, pentaerythritoltetraacrylate, pentaerythritoltetramethacrylate, ethoxylated trimethylolpropanetriacrylate, glycerol-propoxytriacrylate, ethyleneglycoldiacrylate, tripropylene-glycoldiacrylate, and tetraethyleneglycoldiacrylate. ### Claim 9 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the multifunctional oligomeric material is selected from the group consisting of acrylated urethanes, polyesters, and polyepoxides; and acrylics. ### Claim 10 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the acidic precursor has an acid number between about 100 and about 900. ### Claim 11 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the polymer contains about 10 weight parts or more of the acidic precursor, and wherein the acidic precursor is taken from the group consisting of acrylic acid, itaconic acid, .beta.-carboxyethylacrylate, 2-(acryloyloxy)ethyl-o-phthalate, 2-(acryloyloxy)ethylmaleate, 2-(acryloyloxy)ethylsuccinate, 2-(methacryloyloxy)ethylsuccinate, 2-(methacryloyloxy)ethylmaleate, and 2-(acryloyloxy)propylmaleate. ### Claim 12 (depends on 11) The electrically conductive polymeric material of claim 11 wherein the acidic precursor is .beta.-carboxyethylacrylate. ### Claim 13 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the polymer contains about 10 weight parts or more of the acidic precursor, and wherein the acidic precursor has the structure: ##STR4## wherein R.sub.1 is H, methyl, or ethyl; m is an integer from 1 to 4; ..A.. is a carbon-carbon double bond or single bond, wherein when ..A.. is a double bond n is 1 and when ..A.. is a single bond n is 2. ### Claim 14 (depends on 13) The electrically conductive polymeric material of claim 13 wherein the acidic precursor is 2-(acryloyloxy)ethylmaleate. ### Claim 15 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the polymer contains about 10 weight parts or more of the other monofunctional precursor, and wherein the other monofunctional precursor is selected from the group consisting of N-vinyl pyrrolidone, 2-hydroxyethylacrylate, tetrahydro-furfurylacrylate, 2-hydroxyethylmethacrylate, tetrahydro-furfurylmethacrylate, 2-hydroxypropylacrylate, 2-(2-ethoxy-ethoxy)ethylacrylate, 2-cyanoethylacrylate, and 2-hydroxy-propylmethacrylate. ### Claim 16 (depends on 1) The electrically conductive polymeric material of claim 1 wherein a layer of the polymer, having a thickness between about 10 microns and about 50 microns, coated on an insulating substrate has an electrical resistance between about 1.times.10.sup.8 ohm/.quadrature. and 1.times.10.sup.7 ohm/.quadrature.. ### Claim 17 (depends on 1) The electrically conductive polymeric material of claim 1 wherein an antistatic layer of the polymer coated on an insulating substrate has an electrical resistance between about 1.times.10.sup.8 ohm/.quadrature. and 1.times.10.sup.12 ohm/.quadrature.. ### Claim 18 (depends on 1) The electrically conductive polymeric material of claim 1 having an exposed surface wherein the exposed surface will not permanently adhere to a supported contact adhesive when applied thereto. ### Claim 19 (depends on 1) The electrically conductive polymeric material of claim 1 having a high-gloss surface wherein the high-gloss surface reflects about 70%, or more, of visible light incident on the surface at an angle of about 75.degree. or more. ### Claim 20 (depends on 1) The electrically conductive polymeric material of claim 1 wherein a layer of the polymeric material, having a thickness about 50 microns, or less, is visually transparent in at least one region within the visible spectral region. ### Claim 21 (depends on 1) The electrically conductive polymeric material of claim 1 additionally comprising a 1 to 20 weight parts of a matting agent, based on the total weight of the polymerizable materials. ### Claim 22 (depends on 21) The electrically conductive polymeric material of claim 21 wherein the matting agent comprises particles of average diameter of about 1 .mu.m to about 15 .mu.m. ### Claim 23 (depends on 21) The electrically conductive polymeric material of claim 21 wherein the matting agent is amorphous silica. ### Claim 24 (depends on 1) The electrically conductive polymeric material of claim 1 wherein the electrically conductive release layer comprises 60 to 80 weight parts of the ethylenically unsaturated ammonium precursor and 0.2 to 2 weight parts of the polymerizable, ethylenically unsaturated, organo-silicone precursor. ### Claim 25 (depends on 24) The electrically conductive polymeric material of claim 24 wherein the ethylenically unsaturated ammonium precursor is: ##STR5## in which R.sub.1 is H, methyl, or ethyl; Y is --O-- or --(NR.sub.3)--, wherein R.sub.3 is H or a C.sub.1 -C.sub.4 alkyl; m is an integer from 1 to 4, each R.sub.2 individually is a C.sub.1 -C.sub.4 alkyl group; and ›X!.sup.- is an anion.