Method of manufacturing polyelectrolyte

Abstract

A method of manufacturing a polyelectrolyte having the step of sulfonating polystyrene resin in a state where the polystyrene resin has been dissolved or dispersed in solvent composed of alicyclic compounds.

What is claimed is:  
     
         1 . A method of manufacturing a polyelectrolyte comprising the step of sulfonating polystyrene resin in a state where said polystyrene resin has been dissolved or dispersed in solvent composed of alicyclic compounds.  
     
     
         2 . A method of manufacturing a polyelectrolyte according to  claim 1 , wherein cycloparaffin is employed as said alicyclic compounds.  
     
     
         3 . A method of manufacturing a polyelectrolyte according to  claim 2 , wherein cyclohexane or its derivative is employed as said cycloparaffin.  
     
     
         4 . A method of manufacturing a polyelectrolyte according to  claim 1 , wherein the used solvent is recovered after said sulfonation has been performed.  
     
     
         5 . A method of manufacturing a polyelectrolyte according to  claim 4 , wherein the recovered solvent is again used when the sulfonation is performed.  
     
     
         6 . A polyelectrolyte comprising copolymers composed of styrene and conjugate diene to which ion groups have been introduced, wherein conjugate diene units in said copolymer are crosslinked and/or polymerized, said sulfonic acid having water solubility.  
     
     
         7 . A polyelectrolyte according to  claim 6 , wherein said ion group is at least a material selected from a group consisting of sulfonic acid, its salt, chloromathylated amine salt, carboxylic acid, its salt, PO(OH) 2 , its salt, CH 2 PO(OH) 2  and its salt.  
     
     
         8 . A polyelectrolyte according to  claim 6 , wherein said ion groups are introduced by 20 mol % or more with respect to all monomer units.  
     
     
         9 . A polyelectrolyte according to  claim 6 , wherein said copolymer contains the conjugate diene units by 0.05 mol % to 20 mol % with respect to all monomer units.  
     
     
         10 . A polyelectrolyte according to  claim 6 , wherein said copolymer contains the conjugate diene units by 0.1 mol % to 10 mol % with respect to all monomer units.  
     
     
         11 . A polyelectrolyte according to  claim 6 , wherein the molecular weight Mw of said polyelectrolyte is 600,000 or more.  
     
     
         12 . A polyelectrolyte according to  claim 11 , wherein said polyelectrolyte is used as polymer coagulant for disposing waste water.  
     
     
         13 . A method of manufacturing a polyelectrolyte comprising the steps of: 
 introducing ion groups into copolymer composed of styrene and conjugate diene; and    crosslinking and/or polymerizing conjugate diene units in said copolymer so that said polyelectrolyte is refined into a water soluble polyelectrolyte.    
     
     
         14 . A method of manufacturing a polyelectrolyte according to  claim 13 , wherein said ion group to be introduced is a material selected from a group consisting of sulfonic acid, its salt, chloromethylated amine salt, carboxylic acid, its salt, PO(OH) 2 , its salt, CH 2 PO(OH) 2  and its salt.  
     
     
         15 . A method of manufacturing a polyelectrolyte according to  claim 13 , wherein said ion groups are introduced by 20 mol % or more with respect to all monomer units.  
     
     
         16 . A method of manufacturing a polyelectrolyte according to  claim 13 , wherein said copolymer contains the conjugate diene units by 0.05 mol % to 20 mol % with respect to all monomer units.  
     
     
         17 . A method of manufacturing a polyelectrolyte according to  claim 13 , wherein said copolymer contains the conjugate diene units by 0.1 mol % to 10 mol % with respect to all monomer units.  
     
     
         18 . A method of manufacturing a polyelectrolyte according to  claim 13 , wherein said polyelectrolyte is refined in such a manner that the molecular weight Mw is made to be 600,000 or more.  
     
     
         19 . A method of manufacturing a polyelectrolyte according to  claim 18 , wherein said polyelectrolyte is refined so as to be used as polymer coagulant for disposing waste water.  
     
     
         20 . A method of sulfonating aromatic polymers, comprising the steps of: 
 adding aromatic polymers to solvent which is continuously supplied so that the aromatic polymers are dissolved;    supplying a sulfonating agent to said solvent to perform sulfonating reactions;    separating reactant solid materials generated during the sulfonating reactions and the solvent from each other; and    returning the separated solvent so as to be again used in said sulfonating reactions.    
     
     
         21 . A method of sulfonating aromatic polymers according to  claim 20 , wherein the separated reactant solid materials are as it is dried so that sulfonated substances of the aromatic polymers are obtained.  
     
     
         22 . A method of sulfonating aromatic polymers according to  claim 20 , wherein the separated reactant solid materials are dissolved in water or alkaline solution so that water solution of the aromatic polymers into which sulfonate has been introduced is obtained.  
     
     
         23 . A method of sulfonating aromatic polymers according to  claim 20 , wherein said solvent is alicyclic hydrocarbon.  
     
     
         24 . A method of disposing plastic containing halogen flame retardant, comprising the steps of: 
 processing plastic containing halogen flame retardant with acid in organic solvent to introduce ion groups into resin components to form water soluble polymers; and    separating the halogen flame retardant in said organic solvent.    
     
     
         25 . A method of disposing plastic containing halogen flame retardant according to  claim 24 , wherein said plastic containing the halogen flame retardant is waste plastic.  
     
     
         26 . A method of disposing plastic containing halogen flame retardant according to  claim 24 , wherein said halogen flame retardant is bromine flame retardant.  
     
     
         27 . A method of disposing plastic containing halogen flame retardant according to  claim 24 , wherein said resin component is a polymer having an aromatic ring.  
     
     
         28 . A method of disposing plastic containing halogen flame retardant according to  claim 27 , wherein said polymer having said aromatic ring is styrene polymer.  
     
     
         29 . A method of disposing plastic containing halogen flame retardant according to  claim 24 , wherein said ion group is at least one material selected from a group consisting of a sulfonate group, its salt, a carboxyl group, its salt, hydroxyl group, its salt, phosphate group or its salt.  
     
     
         30 . A method of disposing plastic containing halogen flame retardant according to  claim 24 , wherein said organic solvent is at least one material selected from a group consisting of alicyclic hydrocarbon solvent, aliphatic halogenated hydrocarbon solvent and nitrated solvent.  
     
     
         31 . A method of disposing plastic containing halogen flame retardant according to  claim 24 , wherein said water soluble polymers from which the halogen flame retardant has been separated and removed are recovered so as to be again used.  
     
     
         32 . A polyelectrolyte comprising copolymers composed of styrene and conjugate diene to which ion groups have been introduced, wherein said polyelectrolyte has water solubility.  
     
     
         33 . A polyelectrolyte according to  claim 32 , wherein said ion group is at least a material selected from a group consisting of sulfonic acid, sulfonate and chloromathylated amine salt.  
     
     
         34 . A polyelectrolyte according to  claim 33 , wherein said copolymers contain conjugate diene units by 0.1 mol % to 20 mol % with respect to all of monomer units.  
     
     
         35 . A polyelectrolyte according to  claim 33 , wherein said ion groups are introduced by 20 mol % or more with respect to all of monomer units.  
     
     
         36 . A polyelectrolyte according to  claim 32 , wherein said ion group is at least a material selected from a group consisting of sulfonic acid, its salt, chloromathylated amine salt, carboxylic acid, its salt, PO(OH) 2 , its salt, CH 2 PO(OH) 2  and its salt, said ion groups containing inorganic pigment.  
     
     
         37 . A polyelectrolyte according to  claim 36 , wherein said inorganic pigment is carbon black.  
     
     
         38 . A polyelectrolyte according to  claim 36 , wherein said copolymer containing conjugate diene units by 0.05 mol % to 60 mol % with respect to all of monomer units.  
     
     
         39 . A polyelectrolyte according to  claim 36 , wherein said ion groups are introduced by 20 mol % or more with respect to all of monomer units.  
     
     
         40 . A method of manufacturing a polyelectrolyte, comprising the step of introducing ion groups into copolymer of styrene and conjugate diene.  
     
     
         41 . A method of manufacturing a polyelectrolyte according to  claim 40 , wherein at least one material selected from a group consisting of sulfonic acid, sulfate and chloromethylated amine salt is introduced as said ion group.  
     
     
         42 . A method of manufacturing a polyelectrolyte according to  claim 41 , wherein a material containing conjugate diene units by 0.1 mol % to 20 mol % with respect to all of monomer units is employed as said copolymer.  
     
     
         43 . A method of manufacturing a polyelectrolyte according to  claim 41 , wherein said ion groups are introduced by 20 mol % or more with respect to all of monomer units.  
     
     
         44 . A method of manufacturing a polyelectrolyte according to  claim 40 , wherein at least a material selected from a group consisting of sulfonic acid, its salt, chloromathylated amine salt, carboxylic acid, its salt, PO(OH) 2 , its salt, CH 2 PO(OH) 2  and its salt is introduced as said ion groups in a state where inorganic pigment is allowed to exist in a reaction system.  
     
     
         45 . A method of manufacturing a polyelectrolyte according to  claim 44 , wherein carbon black is allowed to exist as said inorganic pigment.  
     
     
         46 . A method of manufacturing a polyelectrolyte according to  claim 44 , wherein the content of said inorganic pigment in said reaction system is 0.01 wt % to 20 wt % with respect to the copolymer components.  
     
     
         47 . A method of manufacturing a polyelectrolyte according to  claim 44 , wherein a material containing conjugate diene units by 0.05 mol % to 60 mol % with respect to all of monomer units is employed as said copolymer.  
     
     
         48 . A method of manufacturing a polyelectrolyte according to  claim 44 , wherein said ion groups are introduced by 20 mol % or more with respect to all of monomer units.  
     
     
         49 . A polyelectrolyte composition comprising: 
 water soluble polystyrene polyelectrolyte; and    stabilizer.    
     
     
         50 . A polyelectrolyte composition according to  claim 49 , wherein said stabilizer contains an oxidation preventive agent composed of at least one material selected from a group consisting of a phenol oxidation preventive agent, a sulfur oxidation preventive agent, a phosphor oxidation preventive agent, erysorbic acid, erysorbic acid soda and isopropyl citrate.  
     
     
         51 . A polyelectrolyte composition according to  claim 49 , wherein said stabilizer is a light stabilizer composed of at least one material selected from a group consisting of a benzophenol stabilizer, a benzotriazole stabilizer, a hindered amine stabilizer, a cyanoacrylate stabilizer, a salicylate stabilizer and oxalicacid anilide stabilizer.  
     
     
         52 . A polyelectrolyte composition according to  claim 49 , wherein said stabilizer contains an oxidation preventive agent and a light stabilizer.  
     
     
         53 . A polyelectrolyte composition according to  claim 49 , wherein said stabilizer is contained by 0.002 parts by weight to 10 parts by weight with respect to 100 parts by weight of said polystyrene polyelectrolyte.  
     
     
         54 . A polyelectrolyte composition according to  claim 49 , wherein at least one material selected from a group consisting of sulfonic acid, sulfonate, carboxylic acid, carboxylate, —PO(OH) 2 , —PO(OH) 2  salt, —CH 2 PO(OH) 2  and —CH 2 PO(OH) 2  salt is introduced into said polystyrene polyelectrolyte.  
     
     
         55 . A method of manufacturing a polyelectrolyte composition such that polystyrene polyelectrolyte and stabilizer are mixed so that said polyelectrolyte composition is manufactured, said method of manufacturing a polyelectrolyte composition comprising the step of: 
 adding said stabilizer when ion groups are introduced into styrene polymers or when water soluble styrene monomers are polymerized or copolymerized to refine said polystyrene polyelectrolyte.    
     
     
         56 . A sulfonation method comprising the step of allowing alicyclic unsaturated hydrocarbon to exist when resin containing styrene polymers is sulfonated in solvent.  
     
     
         57 . A sulfonation method according to  claim 56 , wherein said styrene polymers contain styrene units by 30 mol % or more of total units and said styrene polymers are contained by 20 wt % or more of the overall quantity of said resin.  
     
     
         58 . A sulfonation method according to  claim 56 , wherein said resin containing said styrene polymers is a waste.  
     
     
         59 . A sulfonation method according to  claim 56 , wherein said alicyclic unsaturated hydrocarbon is six membered ring alicyclic unsaturated hydrocarbon.  
     
     
         60 . A sulfonation method according to  claim 56 , wherein said alicyclic unsaturated hydrocarbon is allowed to exist by 0.01 wt % to 5 wt % with respect to said styrene polymers.  
     
     
         61 . A sulfonation method according to  claim 56 , wherein said resin containing said styrene polymers previously contains alicyclic unsaturated hydrocarbon.  
     
     
         62 . A sulfonation method according to  claim 61 , wherein said resin containing said styrene polymers is obtained by contracting foamable styrol with said alicyclic unsaturated hydrocarbon and recovering the contracted foamable styrol.  
     
     
         63 . A sulfonation method according to  claim 62 , wherein said alicyclic unsaturated hydrocarbon is limonene.  
     
     
         64 . A sulfonation method according to  claim 56 , wherein said resin containing said styrene polymers contains inorganic pigment.  
     
     
         65 . A sulfonation method according to  claim 63 , wherein said inorganic pigment is carbon black and/or titanium oxide.  
     
     
         66 . A sulfonation method according to  claim 63 , wherein said inorganic pigment is contained by 0.01 wt % to 10 wt % with respect to said resin containing said styrene polymers.