Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/02—Polycondensates containing more than one epoxy group per molecule
  • C08G59/025—Polycondensates containing more than one epoxy group per molecule characterised by the purification methods used
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/02—Polycondensates containing more than one epoxy group per molecule
  • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
  • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
  • C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/14—Polycondensates modified by chemical after-treatment
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

• the present disclosure relates to methods for reducing impurities in a solid epoxy resin (SER), and in particular for reducing ionic species in SER in discrete particulate form.
• SER solid epoxy resin
• Epoxy is a thermosetting polymer formed from the reaction of an epoxy "resin” with a polyamine “hardener.” Epoxy has a wide range of applications, including coatings, adhesives, fiber-reinforced plastic materials, composite materials, and electrical laminates. In general, epoxies are known for their adhesion, chemical and heat resistance, mechanical properties and electrical insulating properties.
• SER's have been prepared in a variety of ways, including the condensation of a bisphenol and epichlorohydrin in a water medium.
• Some drawbacks include additional steps needed to reduce impurities that were formed during the formation of the epoxy resin and to recover the epoxy resin after the impurity reduction.
• One previous method to reduce impurities includes repeating a high temperature water/steam wash.
• Another method involves completely dissolving the epoxy resin in an organic solvent, followed by a liquid-liquid extraction of impurities and further followed by solvent removal to separate the resin.
• the required high temperatures required to remove the solvent to sufficiently low levels, e.g. , 2500 parts per million (ppm) and the additional steps can be time-consuming and increase usage of energy and materials, which increases the cost of production.
• Solid epoxy resin refers to an epoxy resin whose physical form is in a solid state at ambient temperature within a range of from 23 degrees Celsius (°C) to 25 °C.
• Discrete particulate form refers to SER composed of distinct epoxy resin particulates, e.g. , a powder.
• Softening point temperature refers to the temperature at which a material is softened, such that the material yields under a definite stress, to flow or move a definite amount.
• the present disclosure provides methods for reducing impurities in
• PCT US09/547431 (PCT US09/547431), filed August 24, 2009, the entire content of which is incorporated herein by reference, provides methods of forming SER in discrete particulate form.
• PCT/US09/547431 reacts a bisphenol with a compound such as epichlorohydrin in the presence of aqueous caustic alkali and a dispersion promoting agent, e.g., cellulose ethers, to form the SER in discrete particulate form.
• a dispersion promoting agent e.g., cellulose ethers
• the methods include heating a heterogeneous mixture including the
• SER while maintaining the SER in discrete particulate form, and a solution to a predetermined temperature below the SER's softemng point temperature, agitating the heterogeneous mixture at the predetermined temperature for a predetermined time to extract ionic species, e.g. , chloride ions (Cf), from the SER into the solution, and separating the SER in discrete particulate form from the ionic species in solution.
• ionic species e.g. , chloride ions (Cf)
• the discrete particulate form of the SER increases the interfacial surface area between the SER and the solution as compared to SER that is not in discrete particulate form. This allows ionic species to be extracted from the SER into the solution thereby reducing the overall ionic species concentration in the SER in discrete particulate form.
• the solution is selected from a water miscible solvent, water and combinations thereof.
• the water miscible solvent is selected from water miscible alcohols and water miscible ethers that maintain the SER in discrete particulate form when in the solution.
• the water miscible solvent can be employed within a range of from zero (0) volume percent (vol%) to 100 vol%, preferably within a range of from 0 vol% to 60 vol%, more preferably within a range of from 10 vol% to 50 vol% and still more preferably within a range of from 20 vol% to 40 vol%, the volume percent based on the total volume of the solution.
• the total volume of the solution can be expressed in a weight ratio of the SER in discrete particulate form to the solution and is within a range of from 1 : 1 to 1 :30, preferably within a range of from 1 :3 to 1 : 10 and more preferably within a range of from 1 :3 to 1 :5.
• Examples of water miscible alcohols include C ⁇ to C 6 alcohols and isomers. For example, methanol, ethanol, n-propanol, 2-propanol, n-butanol, 2- butanol, t-butanol, 2-methyl-2-butuanol, 1-pentanol, 2-pentanoL 3-pentanol, 2- methyl-l-pentanol. 2-methyl-2-pentanol, 4-methyl-2-pentanol and mixtures thereof.
• Examples of water miscible ethers include 1 -methoxy-2-ethanol, l-ethoxy-2-ethanol, l-butoxy-2-ethanol, l-methoxy-2-propanol,.
• additional solvents examples include glycerin, propylene glycols, ethylene glycols, butylene glycols, polyethylene glycols, monomethoxypolyethylene glycols, ethylene oxides, propylene oxides, and combinations thereof.
• the water miscible solvents can be mixed together in combinations that allow for the extraction of the ionic species, e.g., CI " , while maintaining the discrete particulate form of the SER.
• the solution may contain one or more additional substances that differ from water and the water miscible solvent.
• additional substances include toluene, xylene, methylethyl ketone and methylisobutyl ketone. These substances can be employed within a range of from 0 vol% to 15 vol%, preferably within a range of from 0 vol°/o to 10 vol% and more preferably within a range of from 2 vol% to 8 vol%, the volume percent based on the total volume of the solution.
• the methods include adding the SER in discrete particulate form to the solution to form the heterogeneous mixture.
• the heterogeneous mixture is maintained at the predetermined temperature for a predetermined time.
• the predetermined time is within a range of from 5 minutes (min.) to 60 min., more preferably within a range of from 5 min. to 20 min.
• the predetermined temperature is within a range of from 20 °C to a temperature of 5 °C below the SER's softening point temperature. Maintaining the predetermined temperature maintains the integrity of the discrete particulate form of the SER.
• the methods are conducted at a pressure within a range of from 1 standard atmosphere (atm) (101.3 kilopascal) to 10 atm, preferably within a range of from 1 atm to 5 atm and more preferably within a range of from 1 atm to 2 atm.
• the agitating reduces the ionic species, e.g. , CI " , in the SER in discrete particulate form such that the concentration of CI " in the SER is less than the concentration of CI " in the solution.
• the mixer for agitating is selected from the type that gives sufficient mixing and heat transfer to extract the ionic species, e.g., CI " .
• Such mixers include reactors equipped with an overhung agitator, roto-stator mixers, high speed dispersers, colloid mills, static in-line mixers, and high shear in-line mixers.
• the range of agitation is within a range of from 10 revolutions per minute (rpm) to 20000 rpm, preferably within a range of from 500 rpm to 20000 rpm, more preferably within a range of from 1000 rpm to 10000 rpm and still more preferably within a range of from 1000 rpm to 6000 rpm.
• Separating the SER in discrete particulate form from the ionic species, e.g., CI " , in solution occurs by standard separation techniques such as centrifugation or filtration.
• the separated SER is in discrete particulate form and if desired undergoes drying. For example, the separated SER is dried in a vacuum at 20°C.
• the operating mode of the mixer can be either a batch process or a continuous process.
• extracting the ionic species e.g., CY
• the separation of the extracted SER particles and the drying of the extracted SER particles may be conducted in either a batch or continuous manner.
• the starting material for Ex 1 is the SER in discrete particulate form formed from the methods of PCT/US09/547431.
• the starting material has an initial CI " concentration of 7400 ppm, a mean particulate size of 420 micrometers (um), and a softening point temperature of 102 °C.
• the dried SER in discrete particulate form resulting from the repeat of Ex 1 has a CI " concentration of 1410 ppm and a mean particle size of 427 ⁇ .

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Processes Of Treating Macromolecular Substances (AREA)
• Epoxy Resins (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

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Citations (4)

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• 2010
  • 2010-10-05 BR BR112012007769A patent/BR112012007769A2/pt not_active IP Right Cessation
  • 2010-10-05 EP EP10766140A patent/EP2486075A1/en not_active Withdrawn
  • 2010-10-05 WO PCT/US2010/002684 patent/WO2011043803A1/en active Application Filing
  • 2010-10-05 KR KR1020127008976A patent/KR20120093204A/ko not_active Application Discontinuation
  • 2010-10-05 JP JP2012533133A patent/JP2013507482A/ja active Pending
  • 2010-10-05 CN CN2010800453270A patent/CN102574981A/zh active Pending
  • 2010-10-06 TW TW099134005A patent/TW201134844A/zh unknown

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