# US 11,111,376 B2 · Flame-retarded styrene-containing formulations > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,111,376 B2 - Document ID: US11111376B2 - Status: Granted - Kind: B2 - Application number: 16/497,790 - Filed: 2018-03-28 - Published: 2020-01-23 - Granted: 2021-09-07 - Earliest claimed: 2017-03-30 - Applicants: Bromine Compounds LTD. - Inventors: Yaniv Hirschsohn; Eyal Eden - Web page: https://patentgrep.com/patent/US11111376B2 ## CPC - C08L 51/04: grafted on to rubbers - C08L 55/02: ABS [Acrylonitrile-Butadiene-Styrene] polymers - C08K 5/0066: {Flame-proofing or flame-retarding additives} - C08L 27/18: Homopolymers or copolymers or tetrafluoroethene - C08K 3/32: Phosphorus-containing compounds - C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters - C08K 5/136: Phenols containing halogens - C08K 5/3492: Triazines - C08K 5/521: Esters of phosphoric acids, e.g. of H3PO4 - C08K 2201/019: the composition being defined by the absence of a certain additive - C08L 2201/02: Flame or fire retardant/resistant - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A composition comprising: an impact modified styrene-containing polymer; at least one bromine-containing flame retardant; at least one dialkyl phosphinic acid metal salt M1n+(R1R2PO2)n wherein M1 is a metal cation with valence n and R1, R2 are alkyl groups which may be the same or different; at least one anti-dripping agent, wherein the total concentration of the bromine-containing flame retardant and the dialkyl phosphinic acid metal salt is less than 28% by weight based on the sum of all components in the composition, wherein said composition is free of antimony and meets UL-94 V-1/1.6 mm or UL-94 V-0/1.6 mm test requirements. ## Claims ### Claim 1 A composition comprising: an impact modified styrene-containing polymer; wherein the impact modified styrene-containing polymer is selected from the group consisting of acrylonitrile-butadiene-styrene (ABS) and high impact polystyrene (HIPS); at least one bromine-containing flame retardant; at least one metal hypophosphite salt Mq+(H2PO2)q, wherein M indicates a metal cation with valence q; and at least one anti-dripping agent, wherein the total concentration of the bromine-containing flame retardant and the metal hypophosphite is less than 28% by weight based on the sum of all components in the composition, wherein the bromine concentration of the composition is from 9.5 to 15.5% by weight based on the total weight of the composition, wherein the composition is antimony-free and meets UL-94 V-1/1.6 mm or UL-94 V-0/1.6 mm test requirements. ### Claim 2 (depends on 1) A composition according to claim 1, wherein the total concentration of the bromine-containing flame retardant and the metal hypophosphite is from 18 to 26% by weight. ### Claim 3 (depends on 1) A composition according to claim 1, wherein the concentration of the metal hypophosphite is from 2 to 9% by weight based on the total weight of the composition. ### Claim 4 (depends on 1) A composition according to claim 1, wherein the bromine-containing flame retardant has bromine content of 50% to 70% by weight and its bromine atoms are either all aromatically-bound or all aliphatically-bound and the metal hypophosphite is aluminum hypophosphite, calcium hypophosphite or a mixture thereof. ### Claim 5 (depends on 4) A composition according to claim 4, wherein the bromine-containing flame retardant is selected from the group consisting of: (i) Tris(2,4,6-tribromophenoxy)-s-triazine represented by the following formula: (ii) Tris(tribromoneopentyl) phosphate represented by the following formula: iii) Tetrabromobisphenol A represented by the following formula: iv) brominated epoxy resins and end-capped derivatives thereof, represented by the formula: wherein m indicates degree of polymerization, R1 and R2 are independently selected from the group consisting of: ### Claim 6 (depends on 5) A composition according to claim 5, wherein the bromine-containing flame retardant is tris(2,4,6-tribromophenoxy)-s-triazine. ### Claim 7 (depends on 6) A composition according to claim 6, comprising from 60 to 80% by weight of ABS or HIPS, from 15 to 20% by weight of tris(2,4,6-tribromophenoxy)-s-triazine, from 3 to 9% by weight of Al(H2PO2)3, Ca(H2PO2)2 or a mixture thereof and from 0.1 to 0.5% by weight of polytetrafluoroethylene, based on the total weight of the composition. ### Claim 8 (depends on 5) A composition according to claim 5, wherein the bromine-containing flame retardant is tris(tribromoneopentyl) phosphate. ### Claim 9 (depends on 8) A composition according to claim 8, comprising from 60 to 80% by weight of ABS, from 15 to 20% by weight of tris(tribromoneopentyl) phosphate, from 3 to 9% by weight of Al(H2PO2)3, Ca(H2PO2)2 or a mixture thereof and from 0.1 to 0.5% by weight of polytetrafluoroethylene based on the total weight of the composition. ### Claim 10 (depends on 5) A composition according to claim 5, wherein the bromine-containing flame retardant is tetrabromobisphenol A. ### Claim 11 (depends on 10) A composition according to claim 10, comprising from 60 to 80% by weight of ABS, from 18 to 23% by weight of tetrabromobisphenol A, from 3 to 9% by weight of Al(H2PO2)3, Ca(H2PO2)2 or a mixture thereof and from 0.1 to 0.5% by weight of polytetrafluoroethylene based on the total weight of the composition. ### Claim 12 (depends on 5) A composition according to claim 5, wherein the bromine-containing flame retardant is tribromophenol end-capped low-molecular weight resin represented by the following Formula (IVa) and mixtures thereof: wherein m is an integer in the range between 0 and 5 with number-average molecular weight from 1300 to 2500. ### Claim 13 (depends on 12) A composition according to claim 12, comprising from 60 to 80% by weight of ABS, from 18 to 23% by weight of tribromophenol end-capped low-molecular weight epoxy resin of Formula IVa, from 3 to 9% by weight of Al(H2PO2)3, Ca(H2PO2)2 or a mixture thereof and from 0.1 to 0.5% by weight of polytetrafluoroethylene based on the total weight of the composition. ### Claim 14 (depends on 13) A composition according to claim 13, wherein the composition further comprises an additive selected from the group consisting of aryl phosphate ester of hydroquinone, polydimethylsiloxane and novolac epoxy resins. ### Claim 15 (depends on 14) A composition according to claim 14, wherein the bromine concentration of the composition is from 10 to 15% by weight and the bromine/metal hypophosphite(s) weight ratio is greater than 2:1. ### Claim 16 (depends on 15) A composition according to claim 15, wherein the bromine/metal hypophosphite(s) weight ratio is from 3:1 to 7:1. ### Claim 17 (depends on 14) A composition according to claim 14, comprising from 60 to 80% by weight of ABS, from 15 to 20% by weight of tris(2,4,6-tribromophenoxy)-s-triazine, from 3 to 6% by weight of Al (H2PO2)3, Ca(H2PO2)2 or a mixture thereof, from 1 to 10% by weight of a combination consisting of aryl phosphate ester of hydroquinone and at least one of polydimethylsiloxane and novolac epoxy resins, and from 0.1 to 0.5% by weight of polytetrafluoroethylene based on the total weight of the composition. ### Claim 18 (depends on 14) A composition according to claim 14, comprising ABS, 10 to 15% by weight bromine supplied by the bromine-containing flame retardant, Ca(H2P02)2 and polydimethylsiloxane wherein the weight ratio bromine: Ca(H2PO2)2 is greater than 2:1 and the weight ratio Ca(H2PO2)2: polydimethylsiloxane is from 7:1 to 1:2. ### Claim 19 (depends on 18) A composition according to claim 18, wherein the total concentration of the Ca(H2PO2)2 +polydimethylsiloxane mixture is from 4 to 7% by weight based on the total weight of the composition. ### Claim 20 (depends on 19) A composition according to claim 19, comprising from 70 to 80% ABS, from 15 to 22.5% by weight of tris(2,4,6-tribromophenoxy)-s-triazine, from 2.0 to 5.0% by weight of Ca(H2PO2)2, from 0.5 to 4.0% polydimethylsiloxane and from 0.1 to 0.5% by weight of polytetrafluoroethylene based on the total weight of the composition. ### Claim 21 (depends on 13) A composition according to claim 13, further comprising from 0.5 to 3% by weight of talc based on the total weight of the composition. ### Claim 22 (depends on 21) A composition according to claim 21, comprising from 60 to 80% by weight of ABS, from 13 to 18% by weight of tris(2,4,6-tribromophenoxy)-s-triazine, from 4 to 8% by weight of Al(H2PO2)3, Ca(H2PO2)2 or a mixture thereof, from 0.5 to 3% by weight of talc and from 0.1 to 0.5% by weight of polytetrafluoroethylene based on the total weight of the composition. ### Claim 23 (depends on 1) A molded article comprising the composition of claim 1.