# US 10,118,887 B2 · Alkyl alpha-hydroxymethyl acrylates as reactive surfactants in emulsion polymerization > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,118,887 B2 - Document ID: US10118887B2 - Status: Granted - Kind: B2 - Application number: 14/832,459 - Filed: 2015-08-21 - Published: 2016-02-25 - Granted: 2018-11-06 - Earliest claimed: 2014-08-21 - Assignees: The University of Akron - Applicants: Abraham Joy; Chao Peng - Inventors: Abraham Joy; Chao Peng - Web page: https://patentgrep.com/patent/US10118887B2 ## CPC - C07C 69/732: of unsaturated hydroxy carboxylic acids - C08F 220/20: of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} - C08F 220/1804: {C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate} - C08L 33/06: of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Polymers including α-hydroxymethylacrylate units and methods of preparing polymers from α-hydroxymethylacrylates are provided. Advantageously, α-hydroxymethylacrylates may be used in an emulsion polymerization and function as a polymerizable surfactant. The ability of the α-hydroxymethylacrylates to be used as a polymerizable surfactant allows for emulsion polymerization systems to be prepared without other surfactants. ## Claims ### Claim 1 A method of preparing a polymer comprising: an emulsion polymerization that employs at least one α-hydroxymethylacrylate as a reactive surfactant and does not employ an additional surfactant other than the at least one α-hydroxymethylacrylate, where the at least one α-hydroxymethylacrylate is defined by the formula: where R2 is a hydrocarbon group with at least 3 carbon atoms. ### Claim 2 (depends on 1) The method of claim 1, wherein the α-hydroxymethylacrylate is defined by the formula where R2 is a hydrocarbon group selected from the group consisting of n-propyl, n-butyl, t-butyl, n-pentyl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and benzyl. ### Claim 3 (depends on 1) The method of claim 1, where the polymerization is initiated with water-soluble free radical initiator. ### Claim 4 (depends on 1) The method of claim 1, where the polymerization is mediated with a Reversible Addition-Fragmentation chain Transfer agent. ### Claim 5 (depends on 1) The method of claim 1, where the polymerization further includes a monomer selected from the group consisting of acrylonitrile, alkyl acrylates, alkyl methacrylates, acrylic acid, methacrylic acid, styrene, and combinations thereof. ### Claim 6 (depends on 1) The method of claim 1, where the emulsion polymerization produces a polymer with an α-hydroxymethylacrylate unit that includes a hydroxyl group defined by the following formula where R2 is a hydrocarbon group with at least 3 carbon atoms. ### Claim 7 (depends on 6) The method of claim 6, where the hydroxyl group is reacted with compound selected from esters, carboxylic acid anhydrides, halogen phosphonates, lactones, cyclic carbonates, and lactides. ### Claim 8 (depends on 1) The method of claim 1, where the α-hydroxymethylacrylate has a critical micelle concentration, and the emulsion polymerization takes place in an emulsion polymerization system that includes an amount of the α-hydroxymethylacrylate above the critical micelle concentration of the α-hydroxymethylacrylate. ### Claim 9 (depends on 1) The method of claim 1, where the emulsion polymerization takes place in an emulsion polymerization system that includes a molar percentage based on the total monomer content of the α-hydroxymethylacrylate that is greater 1%. ### Claim 10 A latex comprising: a polymer with units derived from the emulsion polymerization of at least one α-hydroxymethylacrylate employed as a reactive surfactant, where no additional surfactant other than the at least one α-hydroxymethylacrylate is employed; where the at least one α-hydroxymethylacrylate is defined by the formula: where R2 is a hydrocarbon group with at least 3 carbon atoms. ### Claim 11 (depends on 10) The latex of claim 10, where at least 5% of the polymer units are derived from the polymerization of α-hydroxymethylacrylate. ### Claim 12 (depends on 10) The latex of claim 10, where the polymer further includes units derived from the polymerization of a monomer selected from the group consisting of acrylonitrile, alkyl acrylates, alkyl methacrylates, acrylic acid, methacrylic acid, styrene, and combinations thereof. ### Claim 13 (depends on 10) The latex of claim 10, where the polymer is defined by the formula where each R2 is individually a hydrocarbon group with at least 3 carbon atoms and n is about 100 to about 2000 units. ### Claim 14 (depends on 10) The latex of claim 10, where the polymer is a copolymer defined by the formula where each R2 is individually a hydrocarbon group with at least 3 carbon atoms, each R3 is individually the side chain of a acrylonitrile, alkyl acrylates, alkyl methacrylates, acrylic acid, methacrylic acid, styrene, each R4 is individually a hydrogen atom or a hydrocarbon group, and n is about 100 to about 5000 units, and o is about 100 to about 10000 units. ### Claim 15 (depends on 10) The latex of claim 10, where the polymer is prepared using a RAFT agent and the polymer is defined by the formula where each R2 is individually a hydrocarbon group with at least 3 carbon atoms, n is about 50 to about 1000 units, and Z is a segment of a RAFT agent. ### Claim 16 (depends on 10) The latex of claim 10, where the polymer is a copolymer prepared using a RAFT agent and the polymer is defined by the formula where each R2 is individually a hydrocarbon group with at least 3 carbon atoms, each R3 is individually the side chain of a acrylonitrile, alkyl acrylates, alkyl methacrylates, acrylic acid, methacrylic acid, or styrene monomer, each R4 is individually a hydrogen atom or a hydrocarbon group, n is about 50 to about 1000 units, o is about 50 to about 1000 units, and Z is a segment of a RAFT agent.