# US 10,767,010 B2 · Purified poly(phenylene ether), and poly(phenylene ether) composition and article > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,010 B2 - Document ID: US10767010B2 - Status: Granted - Kind: B2 - Application number: 16/355,044 - Filed: 2019-03-15 - Published: 2019-09-26 - Granted: 2020-09-08 - Earliest claimed: 2018-03-22 - Assignees: Sabic Global Technologies B.V. - Applicants: SABIC Global Technologies B.V. - Inventors: Gurunath CS; Arun Kumar; Kalsang Tharpa; Jinto Jose - Web page: https://patentgrep.com/patent/US10767010B2 ## CPC - C08G 65/46: Post-polymerisation treatment, e.g. recovery, purification, drying - B01J 20/12: Naturally occurring clays or bleaching earth - B01J 20/28061: {being in the range 100-500 m2/g} - C08G 65/38: derived from phenols - C08K 3/346: {Clay} - C08K 5/09: Carboxylic acids; Metal salts thereof; Anhydrides thereof - C08K 5/17: Amines; Quaternary ammonium compounds - C08L 71/123: {not modified by chemical after-treatment} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Purification of a poly(phenylene ether) includes contacting a liquid feed solution with a hydrated acidic clay adsorbent under conditions effective to provide a liquid effluent solution. The liquid feed solution includes a poly(phenylene ether), an organic acid impurity, and an amine impurity. The weight average molecular weight of the poly(phenylene ether) of the liquid effluent solution is within 1 percent of the weight average molecular weight of the poly(phenylene ether) of the feed solution, and the concentration of the amine impurity and the organic acid impurity of the liquid effluent solution is reduced by at least 40 percent relative to the concentration of the each impurity in the feed solution. Compositions and articles comprising a purified poly(phenylene ether) are also described. ## Claims ### Claim 1 A process for purification of a poly(phenylene ether), the process comprising contacting a liquid feed solution comprising the poly(phenylene ether), an organic acid impurity, and an amine impurity with a hydrated acidic clay adsorbent under contacting conditions effective to provide a liquid effluent solution, in which the weight average molecular weight of the poly(phenylene ether) is within 1 percent, of the weight average molecular weight of the poly(phenylene ether) in the feed solution, and a concentration of the amine impurity and the organic acid impurity in parts per million by weight is each reduced by at least 40 percent relative to the concentration of each in the feed solution. ### Claim 2 (depends on 1) The process of claim 1, wherein said contacting conditions comprise a temperature of −10 to 200° C., a pressure of 1 to 5 bar; and 0.5 to 10 volume feed per volume hydrated acidic clay per hour. ### Claim 3 (depends on 1) The process of claim 1, wherein the liquid feed solution further comprises an organic acid anhydride impurity, and a concentration of the organic acid anhydride impurity in parts per million by weight is reduced at least 10 percent relative to its concentration in the feed solution. ### Claim 4 (depends on 1) The process of claim 1, wherein the poly(phenylene ether) comprises a poly(2,6-dimethyl-1,4-phenylene ether); and the feed solution comprises 1 to 25 weight percent, based on the total weight of the feed solution. ### Claim 5 (depends on 1) The process of claim 1, wherein the organic acid impurity comprises an acrylic acid or methacrylic acid, and wherein the liquid feed solution comprises 10 to 5,000 parts per million by weight of the organic acid impurity, based on the total weight of the poly(phenylene ether). ### Claim 6 (depends on 1) The process of claim 1, wherein the amine impurity comprises a C1-36 organic amine, an oligomeric amine, a polymeric amine, or a combination thereof, and wherein the feed solution comprises 10 to 5,000 parts per million by weight of the organic amine impurity, based on the total weight of the poly(phenylene ether). ### Claim 7 (depends on 1) The process of claim 1, wherein the organic amine comprises di-n-butylamine, dimethylbutylamine, N,N,N′,N′-tetramethyl-1,3-diaminopropane, N,N′-di-t-butylethylenediamine, triethanolamine, N-phenyl-ethanolamine, or a combination thereof. ### Claim 8 (depends on 6) The process of claim 6, wherein the polymeric amine or oligomeric amine comprise a polyphenylene ether comprising repeating structural units having the formula wherein each occurrence of Z1 is independently halogen, unsubstituted or substituted C1-C12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C1-C12 hydrocarbylthio, C1-C12 hydrocarbyloxy, or C2-C12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms, provided that at least one occurrence of Z1 is an aminoalkyl-containing group; and each occurrence of Z2 is independently hydrogen, halogen, unsubstituted or substituted C1-C12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C1-C12 hydrocarbylthio, C1-C12 hydrocarbyloxy, or C2-C12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms. ### Claim 9 (depends on 1) The process of claim 1, wherein the hydrated acidic clay comprises an illite chloride clay, a kaolinite clay, a smectite clay, a vermiculite clay, or a combination comprising at least one of the foregoing, and wherein the hydrated acidic clay adsorbent contains 0.01 to 0.2 kilo of water per kilo of dry clay; has an acidity of 5 to 400 milligram of potassium hydroxide per gram clay at phenolphthalein end point, has a particle size of 100 to 2000 micrometers, and has a BET/dinitrogen surface area of 200 to 500 square meters per gram. ### Claim 10 A poly(phenylene ether) composition comprising a bifunctional phenylene ether oligomer having the structure wherein Q1 and Q2 are each independently halogen, unsubstituted or substituted C1-C12 primary or secondary hydrocarbyl, C1-C12 hydrocarbylthio, C1-C12 hydrocarbyloxy, and C2-C12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q3 and Q4 is independently hydrogen, halogen, unsubstituted or substituted C1-C12 primary or secondary hydrocarbyl, C1-C12 hydrocarbylthio, C1-C12 hydrocarbyloxy, and C2-C12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; x and y are independently 0 to 30; Z is hydrogen, methacrylate, or acrylate; L has the structure wherein each occurrence of R3 and R4 and R5 and R6 is independently hydrogen, halogen, unsubstituted or substituted C1-C12 primary or secondary hydrocarbyl, C1-C12 hydrocarbylthio, C1-C12 hydrocarbyloxy, and C2-C12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; z is 0 or 1; and Y has a structure comprising wherein each occurrence of R7 is independently hydrogen and C1-C12 hydrocarbyl, and each occurrence of R8 and R9 is independently comprises hydrogen, C1-C12 hydrocarbyl, and C1-C6 hydrocarbylene wherein R8 and R9 collectively form a C4-C12 cycloalkylene group, less than 150 ppm of an organic acid impurity, less than 50 ppm of an amine impurity comprising a C1-36 organic amine, and less than 200 ppm of an amine impurity comprising a polymeric amine. ### Claim 11 (depends on 10) The poly(phenylene ether) composition of claim 10, further comprising a polymer different than the poly(phenylene ether). ### Claim 12 (depends on 10) An article comprising the poly(phenylene ether) of claim 10, wherein the article is a component of a printed circuit board, or a food-contacting article. ### Claim 13 (depends on 1) The process of claim 1, wherein the hydrated acidic clay comprises amesite, attapulgite, beidillite, chryotile, dickite, illite chloride, lizardite, halloysite, hectorite, kaolinite, montmorillonite, nacrite, nontronite, saponite, sepiolite, smectite, vermiculite, or a combination comprising at least one of the foregoing. ### Claim 14 (depends on 1) The process of claim 1, wherein said contacting conditions comprise a temperature of 21 to 65° C.; a pressure of 1 to 5 bar; and 1 to 8 volume feed per volume hydrated acidic clay per hour. ### Claim 15 (depends on 1) The process of claim 1, wherein the poly(phenylene ether) comprises a poly(2,6-dimethyl-1,4-phenylene ether); and the feed solution comprises 10 to 20 weight percent of the poly(phenylene ether), based on the total weight of the feed solution. ### Claim 16 (depends on 1) The process of claim 1, wherein the weight average molecular weight of the poly(phenylene ether) is within 0.5 percent, more preferably within 0.05 percent, of the weight average molecular weight of the poly(phenylene ether) in the feed solution. ### Claim 17 (depends on 8) The process of claim 8, wherein Z1 is a di-n-butylamine group. ### Claim 18 (depends on 1) The process of claim 1, wherein the poly(phenylene ether) comprises a poly(2,6-dimethyl-1,4-phenylene ether); and the feed solution comprises 10 to 20 weight percent of the poly(phenylene ether), based on the total weight of the feed solution.