WO2019031454A1 - 高純度の両親媒性アリールスルホン酸アミン塩ビニルモノマーとその(共)重合物 - Google Patents
高純度の両親媒性アリールスルホン酸アミン塩ビニルモノマーとその(共)重合物 Download PDFInfo
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- WO2019031454A1 WO2019031454A1 PCT/JP2018/029428 JP2018029428W WO2019031454A1 WO 2019031454 A1 WO2019031454 A1 WO 2019031454A1 JP 2018029428 W JP2018029428 W JP 2018029428W WO 2019031454 A1 WO2019031454 A1 WO 2019031454A1
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- 239000012071 phase Substances 0.000 description 1
- FURYAADUZGZUGQ-UHFFFAOYSA-N phenoxybenzene;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 FURYAADUZGZUGQ-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- IKVLFMBTPLXNGO-UHFFFAOYSA-M sodium 2,3-bis(ethenyl)benzenesulfonate Chemical compound [Na+].C(=C)C=1C(=C(C=CC=1)S(=O)(=O)[O-])C=C IKVLFMBTPLXNGO-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- XJAJNAQBHCNNBM-UHFFFAOYSA-N sulfo hydrogen sulfate dihydrate Chemical compound O.O.OS(=O)(=O)OS(O)(=O)=O XJAJNAQBHCNNBM-UHFFFAOYSA-N 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/08—Monoamines containing alkyl groups having a different number of carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
- B01J41/14—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/26—Nitrogen
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/30—Sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention provides a highly pure amphiphilic aryl sulfonic acid amine salt vinyl monomer excellent in storage stability, and a highly pure aryl sulfonic acid amine salt polymer obtained by using the aryl sulfonic acid amine salt vinyl monomer as a raw material About.
- Styrene sulfonates represented by sodium styrene sulfonate are functional monomers having surface activity and cation exchange ability, and besides reactive emulsifiers for emulsion polymerization, water-based rheology control agents, water-based dispersions, water-based cleaning agents It is used in a wide range of fields as an aqueous antistatic agent, a conductive polymer aqueous colloid dopant, and a raw material monomer for producing an ion exchange membrane.
- Patent Document 1 discloses a polymeric substance internal antistatic agent. However, most examples are those that are insoluble or poorly soluble in water or hot water, and depending on the structure of the neutralized amine, it can be made water dispersible or water soluble, but any specific amine structure is described There is no
- cationic polymers and nonionic polymers are generally used, cationic polymers have poor heat resistance and contain a large amount of halogen, making them difficult to apply to electronic component applications, and nonionic polymers are antistatic. There was a problem that Noh and heat resistance were poor.
- the above-mentioned styrene sulfonate has poor oil solubility or contains metal components, so its use is limited.
- the addition amount thereof is 5 wt% (wt%) with respect to an oil-soluble monomer such as methacrylic acid ester and styrene as a base of the emulsion. ) was the upper limit.
- styrene sulfonate in order to further improve the stability of the emulsion or to increase the concentration of sulfonic acid on the surface of the emulsion particles, for example, when the addition amount of styrene sulfonate is increased to about 10 wt%, violent aggregation occurs during polymerization, which is stable It was difficult to obtain emulsion particles. Most of the styrene sulfonate is present in the aqueous phase, which is considered to be the formation of a styrene sulfonate-based polymer in the aqueous phase.
- the stability of the emulsion is improved by the addition of styrene sulfonic acid alkali metal salts, but the alkali metal causes nails etc.
- the addition amount is greatly limited because the metal member is easily corroded.
- cation exchange fibers and membranes are produced by a method of graft polymerizing radically polymerizable monomers on the surface of a substrate such as fibers, membranes, and nonwoven fabrics.
- a polyolefin is mainly used as a base material because of its excellent durability to acid and alkali.
- the efficiency of graft polymerization is extremely low because the styrene sulfonate can not contact the polyolefin at the molecular level.
- Non-Patent Document 1 a method of graft-polymerizing styrene sulfonate to hydrophilic nylon or graft-polymerizing oil-soluble glycidyl methacrylate onto polyolefin and then introducing a sulfonic acid group has been done.
- the cation exchange fiber or membrane obtained using the nylon substrate and glycidyl methacrylate both have a hydrolyzable amide group and an ester group, so there is a problem in the durability to acid and alkali.
- styrene sulfonic acid amine salt using a long-chain alkylamine such as trioctylamine described in Non-Patent Document 2 or Non-Patent Document 3 is soluble in an aromatic hydrocarbon such as toluene.
- polystyrene sulfonic acid amine salts have also been reported instead of styrene sulfonic acid amine salts.
- Patent Document 1 polystyrene sulfonate amine salt obtained by sulfonation of polystyrene followed by neutralization with an amine having 8 or more carbon atoms has improved compatibility with the resin and is useful as an antistatic agent. It is stated that it is.
- Patent Document 5 a composition comprising a polystyrene sulfonic acid trilaurylamine salt obtained by sulfonation of polystyrene in the same manner as Patent Document 1 and then neutralizing with trilaurylamine and trilaurylamine sulfate is a conventional composition. It is stated that the problem is to improve the antistatic property at low humidity.
- polystyrene sulfonic acid is neutralized with an organic amine, dissolved in an alcohol solvent, and then dried to obtain a polymeric styrene sulfonic acid organic amine salt useful as an antistatic agent.
- JP-A-48-65237 Unexamined-Japanese-Patent No. 2014-32952 U.S. Patent No. 8093342 Japanese Patent Application Publication No. 2003-34676 Japanese Patent Application Publication No. 08-104787 JP 2000-273119 A
- an emulsion for paints and adhesives can be produced using trioctylamine styrene sulfonate instead of an alkali metal salt of styrene sulfonate, it can be expected that an emulsion having high metal stability without metal corrosion can be produced.
- trioctylamine styrene sulfonate is poor in water solubility.
- the present invention has been made in view of the above background and problems, and the object thereof is industrially extremely useful having excellent storage stability and amphiphilic property soluble in both water and an organic solvent.
- a highly pure aryl sulfonic acid amine salt vinyl monomer which is an aryl sulfonic acid vinyl monomer, a simple and practical method for producing the same, and a high purity polyaryl sulfonic acid amine salt which is a polymer thereof and a method for producing the same is there.
- the present inventors are represented by the arylstyrene compound represented by parastyrene sulfonic acid compound or specific Formula (1), and specific Formula (2)
- aryl sulfonates of aryl sulfone imide compounds excellent storage stability, good dissolution in organic solvents and water by using an aryl sulfonate amine salt of a tertiary amine represented by a specific formula (3)
- the inventors have found that they exhibit unique properties such as sex, and have completed the present invention.
- the present invention provides the following formula (1) (In formula (1), R 1 is hydrogen or ethenyl group.) Or the following formula (2) (In the formula (2), R 2 represents an ethenyl group, a 4-ethenylphenyl group, a fluorine, a linear or branched alkyl group having 1 to 10 carbon atoms having any number of substituents, 2 to 10 carbon atoms And the arylsulfonic acid represented by the following alkenyl group, an alkynyl group having 2 to 10 carbon atoms, or a cyclic alkyl group having 3 to 10 carbon atoms.
- R 3 , R 4 and R 5 are all different, or any two structures of R 3 , R 4 and R 5 are the same, R 3 , R 4 and R 5 each independently represent a linear or branched or cyclic saturated hydrocarbon group having 1 to 7 carbon atoms, an aryl group having 1 to 7 carbon atoms, or 1 carbon atom To 7 hydroxyalkyl groups, At least one of R 3 , R 4 and R 5 has a tertiary carbon or quaternary carbon or has a ring structure,
- the ring structure is an aryl group, a 5- or 6-membered cycloalkyl group, a 5- or 6-membered ring in which any two of R 3 , R 4 and R 5 are bonded to each other, or R 3 , Any two of R 4 and R 5 are a 5- or 6-membered ring bonded to each other via an oxygen atom.
- tertiary amines represented by Related to aryl sulfonyl sulf
- R 3 , R 4 and R 5 are all different, or any two structures of R 3 , R 4 and R 5 are the same, R 3 , R 4 and R 5 each independently represent a linear or branched or cyclic saturated hydrocarbon group having 1 to 7 carbon atoms, an aryl group having 1 to 7 carbon atoms, or 1 carbon atom To 7 hydroxyalkyl groups, At least one of R 3 , R 4 and R 5 has a ring structure, The ring structure is an aryl group, a 5- or 6-membered cycloalkyl group, a 5- or 6-membered ring in which any two of R 3 , R 4 and R 5 are bonded to each other, or R 3 , The above-mentioned arylsulfonic acid amine salt, wherein any two of R 4 and R 5 are a 5- or 6-membered ring bonded to each other via an oxygen atom.
- R 3 , R 4 and R 5 each independently represent a linear or branched or cyclic
- R 1 is hydrogen or ethenyl group
- R 2 relates to the above-mentioned arylsulfonic acid amine salt which is an ethenyl group, a 4-ethenylphenyl group or a trifluoromethyl group.
- the present invention also relates to the above-mentioned arylsulfonic acid amine salt, which is a salt of parastyrene sulfonic acid and N, N-dimethylcyclohexylamine.
- this invention is a following formula (4) (A mineral acid is added while cooling a tertiary amine represented by Formula (4), wherein R 3 , R 4 and R 5 are the same as in Formula (3) above) to obtain a salt, Following formula (5) (In the formula (5), R 1 is the same as the formula (1), and M represents hydrogen, an alkali metal ion or an alkaline earth metal ion).
- R 2 is the same as the above formula (2) and M represents hydrogen, an alkali metal ion or an alkaline earth metal ion) or an arylsulfonic acid represented by a salt thereof is added
- M represents hydrogen, an alkali metal ion or an alkaline earth metal ion
- an arylsulfonic acid represented by a salt thereof is added
- the present invention relates to a method for producing an arylsulfonic acid amine salt, which is to be reacted.
- the present invention also relates to a polymer of an arylsulfonic acid amine salt obtained by polymerizing the above-mentioned arylsulfonic acid amine salt.
- the above arylsulfonic acid amine salt is dissolved in an arbitrary solvent, and an emulsifier and a molecular weight modifier are added and dissolved as necessary, and then a radical polymerization initiator is added under a nitrogen atmosphere, and heating and stirring are carried out.
- the present invention relates to a method for producing a polymer of an arylsulfonic acid amine salt, which is then reacted.
- the aryl sulfonic acid amine salt monomer of the present invention is an aryl sulfonic acid compound having high purity, high storage stability, and amphiphilic property, and conventional aryl sulfone compounds such as resin and rubber antistatic, graft polymerization to polyolefin, etc. Not only applications requiring lipophilicity that were difficult with acid salt monomers, but also applications requiring a certain degree of water solubility difficult with conventional aryl sulfonic acid amine salt monomers, such as reactive emulsifiers for emulsion polymerization It becomes.
- P-styrenesulfonic acid N obtained in Example 1 shows the proton NMR spectrum of N- dimethylcyclohexylamine salt (CHASS abbreviated), proton H A in FIG, H B, H C, H D, H F, H G , H H , H I , H J, H K , H L , H M , and H N are protons H A , H B , H C , H D, H F , H G , and H H of FIG. 2, respectively. , H I, H J, H K, H L, H M, corresponds to H N.
- CHSS abbreviated N- dimethylcyclohexylamine salt
- Example 1 The structural formula identified from the proton NMR spectrum of the para-styrenesulfonic acid N, N- dimethylcyclohexylamine salt obtained in Example 1 is shown.
- the proton NMR spectrum of parastyrene sulfonic acid N, N-diisopropylethylamine salt (abbreviated as DIPEASS) obtained in Example 3 is shown, and protons H 2 O 2 , H 2 P 4 , H 2 Q 4 , H 2 R, H 2 S , H 2 in the figure.
- DIPEASS N-diisopropylethylamine salt
- H U , H V , H W, H X are protons H O , H P , H Q , H R, H S , H T , H U , H V , H W, H X in FIG. 4 respectively. It corresponds.
- the structural formula identified from the proton NMR spectrum of the parastyrene sulfonic acid N, N- diisopropyl ethylamine salt obtained in Example 3 is shown.
- the present invention relates to a specific formula related to a parastyrene sulfonic acid compound or an aryl sulfonic acid compound such as an aryl sulfonic acid compound represented by a specific formula (1) and an aryl sulfone imide compound represented by a specific formula (2) It relates to an arylsulfonic acid amine salt of a tertiary amine represented by (3) and a polymer thereof.
- the present embodiment modes for carrying out the present invention (hereinafter, referred to as “the present embodiment”) will be described in detail.
- the present invention is not limited to the following embodiment.
- the present invention can be appropriately modified and implemented within the scope of the gist of the present invention.
- the arylsulfonic acid amine salt vinyl monomer of the present embodiment is a salt of an arylsulfonic acid represented by the following formula (1) or the following formula (2) and a tertiary amine represented by the following formula (3) And arylsulfonic acid amine salts, as well as polymers thereof.
- R 1 represents hydrogen or an ethenyl group.
- R 2 represents an ethenyl group, a 4-ethenylphenyl group, a fluorine, a linear or branched alkyl group having 1 to 10 carbon atoms having any number of substituents, 2 to 10 carbon atoms Alkenyl group, alkynyl group having 2 to 10 carbon atoms, or cyclic alkyl having 3 to 10 carbon atoms.
- R 3 , R 4 and R 5 are each independently a linear or branched saturated hydrocarbon group having 1 to 7 carbon atoms, an aryl group or a hydroxyalkyl group, At least one of R 3 , R 4 and R 5 has a tertiary carbon or quaternary carbon in the structure, or has a ring structure,
- the ring structure is an aryl group, a 5- or 6-membered cycloalkyl group, a 5- or 6-membered ring in which any two of R 3 , R 4 and R 5 are bonded to each other, or R 3 , R Any two of 4 and R 5 are a 5- or 6-membered ring bonded to each other via an oxygen atom. ).
- the method for producing the arylsulfonic acid amine salt vinyl monomer of the present embodiment is not particularly limited, but as an example, the arylsulfonic acid metal salt in a nitrogen atmosphere to a reactor equipped with a stirrer, a cooling pipe, and a dropping pipe.
- a solution of an inorganic acid salt of a tertiary amine is dropped into the solution, and the solution is subjected to salt exchange in a homogeneous system or a two-layer system.
- the tertiary amine inorganic acid solution may be charged into a reactor, and the aryl sulfonic acid metal salt solution may be dropped.
- the molar ratio of metal salt of aryl sulfonic acid / primary amine inorganic acid salt at the time of charging is not particularly limited, but is preferably 0.5 to 4.0, and from the viewpoint of removal of raw materials or by-products, 0.8 -1.5 is particularly preferred.
- the metal of the arylsulfonic acid metal salt for example, alkali metals or alkaline earth metals such as sodium, potassium, lithium, calcium and magnesium can be mentioned, and the viewpoint of availability and crystallization Especially, sodium is desirable.
- the inorganic acid in the tertiary amine inorganic acid salt is not particularly limited, but, for example, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, boric acid, hydrofluoric acid, hydrobromic acid, hydrocyanic acid, hexafluorophosphoric acid, etc. Its properties may be in the form of a gas, an aqueous solution, an organic solvent solution or the like without any property in any properties, and from the viewpoint of easy availability and easy handling, hydrochloric acid gas or aqueous hydrochloric acid solution is preferable.
- the reaction solvent to be charged into the reactor and the solvent (dropping solvent) used for the dropping solution are not particularly limited as long as the alkali metal arylsulfonate and the tertiary amine inorganic acid salt are dissolved, and the reaction solvent and the dropping solvent are the same. It may be or different.
- water such as water, acetone, tetrahydrofuran, dioxane, methanol, ethanol, n-propanol, isopropanol, methoxyethanol, ethoxyethanol, butanol, ethylene glycol, propylene glycol, glycerin, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone or the like
- Water-soluble solvents such as pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, cyclohexane, methylcyclohexane, benzene, toluene, o -Aromatic hydrocarbons such as pentane, hexane
- Water or a mixed solution of water and a water-soluble solvent is preferred as the solvent of the metal salt of aryl sulfonic acid, and the solvent of the amine inorganic acid salt differs depending on the nature of the amine, but water or water and water-soluble solvent, chloroform, Halogen solvents such as dichloromethane are preferable because the solubility of the amine inorganic salt is high and removal is easy.
- the concentration of the arylsulfonic acid amine salt is 5 wt% (wt%) to 79 wt% based on the total amount of the charge, and 10 wt% to 70 wt% is preferable from the viewpoint of reaction promotion and suppression of byproducts.
- the reaction temperature is preferably ⁇ 20 ° C. to 50 ° C., and more preferably 0 ° C. to 30 ° C. from the viewpoint of heat polymerization.
- the arylsulfonic acid amine salt vinyl monomer obtained by the exemplified method can be separated and purified from the reaction solution after completion of the reaction by ordinary methods such as filtration, extraction, crystallization and the like.
- the method of separation and purification mainly depends on the physical properties of the tertiary amine to be used, and, for example, when the target substance is isolated by extraction, the metal inorganic acid salt by-produced in the aqueous layer, unreacted arylsulfonic acid metal salt and Amine inorganic acid salts, aryl sulfonic acid amine salts often dissolve in the organic layer.
- an extraction solvent for example, aromatic hydrocarbon solvents such as toluene and xylene, halogen solvents such as chloroform, dichloromethane, 1,1,1-trichloroethane and 1,1,2-trichloroethane, hexane, cyclohexane and methylcyclohexane And aliphatic hydrocarbon solvents, ester solvents such as ethyl acetate and butyl acetate, and ether solvents such as diethyl ether, methyl ethyl ether, and cyclopentyl methyl ether; single or mixed solvents of organic solvents such as ether solvents.
- aromatic hydrocarbon solvents such as toluene and xylene
- halogen solvents such as chloroform, dichloromethane, 1,1,1-trichloroethane and 1,1,2-trichloroethane
- hexane cyclohexane and methylcyclohexane
- parastyrene sulfonate amine salt as an example, first, 4- (2-haloethyl) benzenesulfonic acid solution and radical polymerization inhibitor are charged into a reactor equipped with a stirrer and a condenser, and deoxygenated sufficiently. After raising the temperature to a temperature, a tertiary amine or a solution thereof is continuously added dropwise, and vinylation reaction (dehalogenation) can be carried out to produce a parastyrene sulfonic acid amine salt.
- a tertiary amine or a solution thereof and a polymerization inhibitor are charged into a reactor, deoxygenated sufficiently, and after raising the temperature to a predetermined temperature, the 4- (2-haloethyl) benzenesulfonic acid solution is continuously added dropwise. May react.
- a polymerization inhibitor and a tertiary amine or a part of a solution thereof are charged into a reactor, sufficiently deoxygenated, and after raising the temperature to a predetermined temperature, 4- (2-haloethyl) benzenesulfonic acid solution and the remaining amine solution
- the vinylation reaction may be carried out while continuously adding dropwise.
- the polymerization inhibitor which may be used in the production method of the present invention is not particularly limited. Examples thereof include alkali metal nitrites, hydroquinone, methoxyhydroquinone, anthraquinone sulfonate, ammonium nitrosophenylhydroxylamine, N -Nitrosophenylhydroxyamine aluminum salt, 2-t-butyl hydroquinone, 4-t-butyl catechol and the like.
- the addition amount of the polymerization inhibitor is preferably 10 ppm to 1 wt% with respect to the arylsulfonic acid amine salt.
- the reaction solvent to be charged into the reactor and the solvent used for the dropping solution are not particularly limited as long as they have a composition in which the haloethyl aryl sulfonic acid and the tertiary amine are dissolved and do not affect the reaction.
- Water, or water-soluble solvents such as tetrahydrofuran, dioxane, dimethylsulfoxide, dimethylformamide, N-methylpyrrolidone, etc., aromatic hydrocarbons such as benzene, toluene, o-xylene, m-xylene, p-xylene, etc., methylene chloride, Aliphatic halogen compounds such as chloroform, carbon tetrachloride and 1,2-dichloroethane, and from the viewpoint of ease of dehalogenation progress and solubility of the substrate, water, methylene chloride, chloroform, carbon tetrachloride, 1, 2-Dichloroethane is preferred.
- parastyrene sulfonic acid amine salt precipitates due to the vinylation reaction and cooling of the reaction solution.
- the crystals are separated by a method such as centrifugal filtration to obtain a hydrous salt of parastyrene sulfonate amine salt. Thereafter, the water content may be further reduced by solvent washing or vacuum drying.
- recrystallization and repulping may be performed using water, water and a water-soluble solvent mixed solvent, any organic solvent, etc. .
- the purification solution is not particularly limited, but the water-soluble solvent is methanol, ethanol, isopropanol, n-propanol, butanol, acetone, tetrahydrofuran, acetonitrile, etc., pentane, hexane, cyclohexane, methylcyclohexane, heptane, octane, etc.
- Linear aliphatic hydrocarbons such as nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane and octadecane, and aromatic carbonization such as benzene, toluene, o-xylene, m-xylene and p-xylene Examples thereof include hydrogens, and aliphatic halogen compounds such as methylene chloride, chloroform, carbon tetrachloride and 1,2-dichloroethane.
- a specific example of the aryl sulfonic acid used in the present embodiment is not particularly limited as long as it is a compound having one or two vinyl groups in the aromatic ring, but the parastyrene sulfonic acid represented by the general formula (1), ortho Styrene sulfonic acid, meta styrene sulfonic acid, ortho divinyl benzene sulfonic acid, meta di vinyl benzene sulfonic acid, para di vinyl benzene sulfonic acid, R 2 of the following formula (2) is specifically ethenyl group, 4- ethenyl phenyl group, Trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methylbutyl group, 2-
- parastyrene sulfonic acid paradivinyl benzene sulfonic acid, metadivinyl benzene sulfonic acid in general formula (1), ethenyl group, 4-ethenyl phenyl group, trifluoro in R 2 of general formula (2)
- a methyl group is preferable from the viewpoint of raw material availability.
- the tertiary amine of the general formula (3) used in this embodiment is as described above, but among them, at least one of R 3 , R 4 and R 5 is a 5- or 6-membered cycloalkyl group. Or any two of R 3 , R 4 and R 5 , such as R 3 and R 4 form a 5- or 6-membered ring bonded to each other, or R 3 , R 4 and R 5 Preferably, any two of them, for example, R 3 and R 4 form a 5- or 6-membered ring bonded to each other via an oxygen atom.
- the amine compound represented by the above formula (3) may contain two or more ring structures.
- amine compound represented by the general formula (3) include, but are not limited to, for example, N, N-dimethylbenzylamine, N, N-diethylbenzylamine, N, N-dibenzylmethylamine, N , N-dimethyl-4-methylbenzylamine, N, N-dimethylcyclohexylamine, N, N-diethylcyclohexylamine, N, N-dicyclohexylmethylamine, N, N-dicyclohexylethylamine, N-methylpyrrolidine, N-ethyl Pyrrolidine, N-propyl piperidine, N-butyl piperidine, N-methyl morpholine, N-ethyl morpholine, N-propyl morpholine, N-butyl morpholine, N-sec-butyl morpholine, N-tert-butyl morpholine, N-isobutyl morpholine , N, N-N-d
- the ratio of the molecular weight of the arylsulfonic acid / molecular weight of the tertiary amine compound is preferably 0.8 to 2.0, more preferably 1.3 to 2.0.
- the ratio of the molecular weight of arylsulfonic acid to the molecular weight of the tertiary amine compound is 0.8 or less, that is, the molecular weight of the tertiary amine is too large, the weight part of sulfo group per unit weight of arylsulfonic acid amine salt decreases. As a result of excessive oil solubility, amphiphilicity may be impaired.
- the ratio of the molecular weight of the arylsulfonic acid / molecular weight of the tertiary amine compound is 2.0 or more, that is, when the molecular weight of the tertiary amine is too small, the lack of oil solubility results in loss of amphiphilicity. is there.
- ⁇ Aryl sulfonic acid amine salt (co) polymer Although the manufacturing method of highly purified aryl sulfonic acid amine salt (co) polymer using the highly purified aryl sulfonic acid amine salt monomer shown in the present embodiment is not particularly limited, a general lump can be obtained. Synthesis is possible by a method by radical polymerization such as polymerization, solution polymerization, dispersion polymerization, suspension polymerization, emulsion polymerization and the like.
- the reaction vessel contains a homogeneous solution of an optional solvent and an amine salt of the arylsulfonic acid amine salt shown in this embodiment, and optionally an arylsulfonic acid amine salt and a radical copolymerizable with the arylsulfonic acid amine salt.
- each monomer is used as a polymerization initiator or a molecular weight regulator rather than first charging all monomer mixtures into the reaction vessel.
- the reaction solvent is not particularly limited, but the composition is not particularly limited as long as it is a composition in which the mixture of the arylsulfonic acid amine salt and the comonomer dissolves, and the composition of the solvent may be changed as necessary.
- water such as water, acetone, tetrahydrofuran, dioxane, methanol, ethanol, n-propanol, isopropanol, methoxyethanol, ethoxyethanol, butanol, ethylene glycol, propylene glycol, glycerin, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone or the like
- Water-soluble solvents linear aliphatic hydrocarbons such as pentane, hexane, cyclohexane, methylcyclohexane, heptane, octane, nonane, decane, undecane, dodecane, dodecane, tridecane, t
- the polymerization solvent may be appropriately selected depending on the application of the (co) polymer.
- water or alcohols alone or a mixed solvent is preferable, and the amount of use of the aqueous solvent as the reaction solvent is usually 150 parts by weight to 2,000 parts by weight with respect to 100 parts by weight of total monomer. It is preferable to
- the monomer other than the arylsulfonic acid amine salt used for the arylsulfonic acid amine salt (co) polymer of the present invention is not particularly limited as long as it can be radically copolymerized with the arylsulfonic acid amine salt.
- N-cyclohexyl maleimide N-methyl maleimide, N-ethyl maleimide, N-phenyl maleimide, N- (chlorophenyl) maleimide, N- (methylphenyl) maleimide, N- (isopropylphenyl) maleimide, N- (sulfo) Phenyl) maleimide, N-methylphenyl maleimide, N-bromophenyl maleimide, N-naphthyl maleimide, N-hydroxyphenyl maleimide, N-methoxyphenyl maleimide, N-carboxyphenyl maleimide, N- (nitrophenyl) maleimide, N-benzyl Maleimide, N- (4-acetoxy-1-naphthyl) maleimide, N- (4-oxy-1-naphthyl) maleimide, N- (3-fluoranthyl) maleimide, N- (5-fluoresceinyl
- styrenes, methacrylic acids, acrylic acids, acrylic esters, methacrylic esters, and N-substituted maleimides are preferable in consideration of the copolymerizability with the arylsulfonic acid amine salt, availability, and the like.
- the molecular weight modifier is not particularly limited, and, for example, diisopropylxanthogen disulfide, diethylxanthogen disulfide, diethylthiuram disulfide, 2,2'-dithiodipropionic acid, 3,3'-dithiodipropionic acid, 4,4 Disulfides such as' -dithiodibutanoic acid, 2,2'-dithiobisbenzoic acid, n-dodecyl mercaptan, octyl mercaptan, t-butyl mercaptan, thioglycolic acid, thiomalic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, Thiosalicylic acid, 3-mercaptobenzoic acid, 4-mercaptobenzoic acid, thiomalonic acid, dithiosuccinic acid, thiomaleic acid, thiomaleic anhydride,
- the amount of the molecular weight modifier used is usually 0.1 to 10 parts by weight with respect to 100 parts by weight of the total amount of monomers.
- radical polymerization initiators include di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, benzoyl peroxide, dilauryl peroxide, cumene hydroperoxide, t-butyl hydroperoxide, 1,1-bis (t-butylperoxy) -3,5,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) -cyclohexane, cyclohexanone peroxide, t-butylperoxybenzoate, t- Butyl peroxyisobutyrate, t-butyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxy isopropyl carbonate, cumyl peroxy octoate , Persulfate Peroxides such as lithium, ammonium persulfate and
- the amount of the radical polymerization initiator used is usually 0.1 to 10 parts by weight with respect to 100 parts by weight of the total amount of monomers.
- the above-described radically polymerizable monomer, the arylsulfonic acid amine salt or arylsulfonic acid amine salt of the present invention, and an aqueous solution containing an emulsifier are mixed and stirred or homogenized to emulsify.
- a monomer emulsion is prepared.
- the monomer emulsion may be charged into a reactor and degassed, and then polymerization may be performed at a predetermined temperature while adding a polymerization initiator.
- polymerization may be started by charging a part of the monomer emulsion into the reactor, and polymerization may be performed while continuously adding the remaining monomer emulsion.
- polymerization may be performed while continuously adding a radically polymerizable monomer to a solution containing an emulsifier.
- the radical polymerizable monomer, reaction solvent, radical polymerization initiator, and molecular weight modifier in emulsion radical polymerization are not particularly limited, and, for example, the same compounds as the examples in the solution radical polymerization described above can be used.
- the arylsulfonic acid amine salt of the present invention is a reactive emulsifier having high emulsifying power
- the emulsifier is not necessarily required, but the emulsion may be stabilized by additionally using an emulsifier separately. is there.
- the emulsifier used in this case is not particularly limited, and examples of the anionic emulsifier include rosin acid salt, fatty acid salt, alkenyl succinate, alkyl ether carboxylate, alkyl diphenyl ether disulfonate, alkane sulfonate, Alkyl succinate sulfonate, polyoxyethylene polycyclic phenyl ether sulfate, ⁇ -olefin sulfonate, alkyl benzene sulfonate, naphthalene sulfonate formalin condensate, taurine derivative, polystyrene sulfonate, polystyrene sulfonate styrene Copolymer, polystyrene sulfonic acid N-vinyl pyrrolide copolymer, polystyrene sulfonic acid N-substituted maleimide copolymer, polystyren
- emulsifier for example, polyoxyalkylene alkylamine, alkyl alkanolamide, amine oxide nonionic emulsifier, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyalkylene polycyclic phenyl ether, alkyl propenyl phenol polyethylene oxide addition , Allyl alkyl phenol polyethylene oxide adduct, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid Stel, sorbitan fatty acid ester, glycerin fatty acid ester, alkyl polyglucoxide, sucrose fatty acid ester, polyoxyethylene polyoxypropylene glycol, polyvinyl alcohol, carboxymethyl cellulose, polyvinyl pyrrolidone, hydroxyethyl cellulose, polyacrylamide, polymethacrylamide, polydimethylamino Ethyl methacrylate, polydimethylaminoethyl acrylate, polyacrylamide
- amphoteric emulsifiers include alkyl dimethylamino acetic acid betaines, alkyl dimethylamino sulfos. Betaine, alkyl sulfobetaine and the like can be mentioned.
- the polymer of the arylsulfonic acid amine salt formed by polymerizing the arylsulfonic acid amine salt according to the present invention has, for example, a molecular weight of 1 as a number average molecular weight measured by gel permeation chromatography (GPC). It will be about 5,000 to 5,000,000 daltons (Da).
- the polymer is prepared by dissolving the arylsulfonic acid amine salt in an optional solvent, adding an emulsifier and a molecular weight modifier as required, and then adding a radical polymerization initiator under a nitrogen atmosphere and heating and stirring. It is a polymer of arylsulfonic acid amine salt which is made to react. Detailed physical properties of this polymer, such as chemical structure, are difficult to measure, or it is more easily understood by showing the production method.
- various solvents such as water, an aqueous solvent, a solvent in which an arylsulfonic acid amine salt (monomer) can be dissolved, and the like can be used as a solvent used when dissolving and mixing an arylsulfonic acid amine salt, an emulsifier, a molecular weight modifier and a solvent. It can be used.
- sample A sample of about 0.7 mL of dimethylsulfoxide-d6 (99.5 wt%) or chloroform-d (99.5 wt%) containing about 0.05 wt% of tetramethylsilane as an internal standard substance Were dissolved to prepare a sample for NMR measurement.
- Example 1 [Synthesis Example of Para-Styrene Sulfonic Acid N, N-Dimethylcyclohexylamine Salt] 40.0 g of N, N-dimethylcyclohexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was charged into a 200 mL four-necked glass flask equipped with a reflux condenser, a nitrogen inlet, and a dropping funnel. The mixture was cooled to 0 ° C., and while continuing cooling, a mixed solution of 33.0 g of 35% hydrochloric acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 30.0 g of ion exchanged water was dropped. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour to obtain an aqueous solution of N, N-dimethylcyclohexylamine hydrochloride.
- reaction solution aqueous layer
- chloroform is distilled off with an evaporator, and 80.4 g of a white solid of parastyrene sulfonic acid N, N-dimethylcyclohexylamine salt (yield 82) %, Purity 99.8%).
- the target substance is identified by proton NMR ( 1 H-NMR), and for elemental analysis, carbon (C), hydrogen (H), nitrogen (N) using an elemental analyzer and sulfur (S) as an oxygen flask combustion method Then, after combustion and absorption treatment, SO 4 2 ⁇ ions were quantified by ion chromatography and converted to sulfur (S). Table 1 shows the results of elemental analysis.
- Example 2 [Synthesis Example of Para-Styrene Sulfonic Acid N, N-Dimethylcyclohexylamine Salt]
- a 70% aqueous solution of 4- (2-bromoethyl) benzenesulfonic acid manufactured by Tosoh Organic Chemical Co., Ltd.
- N, N -Charged with 12.5 g of dimethylcyclohexylamine and 27 mg of hydroquinone manufactured by Wako Pure Chemical Industries, Ltd. The mixture was heated to 90 ° C.
- the target was identified by proton NMR ( 1 H-NMR).
- Example 3 [Synthesis Example of Para-Styrene Sulfonic Acid N, N-Diisopropylethylamine Salt] 10.0 g of N, N-diisopropylethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was charged into a 100 mL four-necked glass flask equipped with a reflux condenser, a nitrogen inlet tube, and a dropping funnel. The mixture was cooled to 0 ° C., and while continuing cooling, a mixed solution of 7.5 g of 35% hydrochloric acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 10.0 g of ion exchange water was dropped. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour to obtain an aqueous solution of N, N-diisopropylethylamine hydrochloride.
- reaction solution aqueous layer
- chloroform is distilled off with an evaporator, and 16.2 g of a white solid of parastyrene sulfonic acid N, N-diisopropylethylamine salt (yield 65. 8%, 99.2%).
- the target was identified by proton NMR ( 1 H-NMR).
- Example 4 Synthesis Example of Poly (p-styrenesulfonic acid N, N-dimethylcyclohexylamine salt)]
- a 100 mL glass four-necked flask 1.5 g of parastyrene sulfonic acid N, N-dimethylcyclohexylamine salt obtained in Example 1 and 13.5 g of ion-exchanged water were charged, and stirred at room temperature to dissolve.
- This solution is sufficiently degassed by repeated aspirator decompression and nitrogen introduction, and 0.013 g of 2,2'-azobis (2-methylpropionamidine) dihydrochloride (manufactured by Wako Pure Chemical Industries, Ltd.), Was added while bubbling.
- This solution was heated and stirred at 60 ° C. for 6 hours to obtain a transparent uniform aqueous solution of poly (parastyrene sulfonate N, N-dimethylcyclohexylamine salt.
- the polymerization conversion ratio at the end of the reaction was 100%, and the number average molecular weight was 150. , 000.
- the measurement of the polymerization conversion rate and the number average molecular weight was calculated from the peak area ratio by gel permeation chromatography (GPC).
- Example 5 Example of emulsion polymerization of styrene using para-styrene sulfonic acid N, N-dimethylcyclohexylamine salt
- styrene manufactured by Wako Pure Chemical Industries, Ltd.
- dodecylbenzene sulfonic acid 0.25 g of sodium (manufactured by Wako Pure Chemical Industries, Ltd.) and 20.5 g of ion-exchanged water were charged, and the mixture was stirred and dissolved at room temperature.
- This solution is sufficiently degassed by repeated aspirator decompression and nitrogen introduction, and 0.025 g of 2,2'-azobis (2-methylpropionamidine) dihydrochloride (manufactured by Wako Pure Chemical Industries, Ltd.) Was added while bubbling.
- the solution was heated and stirred at 60 ° C. for 24 hours to obtain an emulsion polymerization solution of styrene.
- the polymerization conversion rate at the end of the reaction was 100%, and the number average molecular weight was 200,000.
- the measurement of the polymerization conversion was calculated from the residual amount of the monomer by GC, and the measurement of the number average molecular weight was calculated by gel permeation chromatography (GPC).
- Example 6 Synthesis Example of Divinylbenzenesulfonic Acid N, N-Dimethylcyclohexylamine Salt
- a 200 mL four-necked glass flask equipped with a reflux condenser, a nitrogen inlet tube, and a dropping funnel 40.0 g of N, N-dimethylcyclohexylamine was charged.
- the mixture was cooled to 0 ° C., and while continuing cooling, a mixed solution of 33.0 g of 35% hydrochloric acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 30.0 g of ion exchanged water was dropped. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour to obtain an aqueous solution of N, N-dimethylcyclohexylamine hydrochloride.
- reaction solution (aqueous layer) is extracted twice with 200 g of chloroform, chloroform is distilled off with an evaporator, and 7.3 g of a white solid of divinylbenzenesulfonic acid N, N-dimethylcyclohexylamine salt (yield 71) .5%, purity 98.0%).
- the target was identified by proton NMR ( 1 H-NMR).
- the target was identified by proton NMR ( 1 H-NMR).
- Comparative example 2 [Synthesis Example of para-styrenesulfonic acid n-monooctylamine salt] 12.9 g of n-monooctylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 70.5 g of ion-exchanged water were charged in a 200 mL four-necked glass flask equipped with a reflux condenser, a nitrogen inlet, and a dropping funnel. The solution was cooled to 0 ° C., and 10.4 g of 35% hydrochloric acid was added dropwise while cooling. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour to obtain an aqueous solution of n-monooctylamine hydrochloride.
- reaction solution is cooled to 5 ° C., and the precipitated crude crystals are filtered, rinsed with 100 g of toluene twice, and dried under reduced pressure to obtain a white solid of para-styrenesulfonic acid n-monooctylamine salt 7 .10 g (yield 70.5%, purity 96.4%) were obtained.
- the target was identified by proton NMR ( 1 H-NMR).
- the target was identified by proton NMR ( 1 H-NMR).
- Comparative example 4 Example of emulsion polymerization of styrene using para-styrene sulfonic acid n-trioctylamine salt
- styrene manufactured by Wako Pure Chemical Industries, Ltd.
- para-styrenesulfonic acid n-trioctylamine salt obtained in Example 1
- sodium dodecylbenzenesulfonate 0.25 g of Wako Pure Chemical Industries, Ltd. and 20.5 g of ion-exchanged water were charged, and the mixture was stirred and dissolved at room temperature.
- This solution was sufficiently degassed by repeated aspirator vacuum and nitrogen introduction, and 0.025 g of 2,2'-azobis (2-methylpropionamidine) dihydrochloride was added while blowing in nitrogen.
- This solution was heated and stirred at 60 ° C. for 24 hours to obtain an emulsion polymerization solution of styrene, but the polymerization conversion ratio at the end of the reaction was 30%, resulting in a large amount of monomer remaining. Moreover, the number average molecular weight was 50,000.
- the measurement of the polymerization conversion was calculated from the residual amount of the monomer by GC.
- the measurement of the number average molecular weight was calculated by gel permeation chromatography (GPC), but since the polymer is non-water-soluble, the polymer is obtained by using a 5-fold volume of a 48% aqueous solution of sodium hydroxide with respect to the reaction solution After converting it to a sodium salt, it was analyzed by GPC.
- parastyrene sulfonic acid N N-dimethylcyclohexylamine salt (CHASS)
- parastyrene sulfonic acid N N-diisopropylethylamine salt (DIPEASS)
- parastyrene sulfonic acid n-trioctylamine TOASS
- n-monooctylamine salt of parastyrene sulfonate MOASS
- DCHASS dicyclohexylamine salt of parastyrene sulfonate
- NaSS sodium salt of parastyrene sulfonate
- Comparative Example 2 which is a primary amine and Comparative Example 3 which is a secondary amine.
- Example 1 of a tertiary amine containing a cyclic skeleton and Example 2 of a tertiary amine containing a tertiary carbon have a carbon number of the amine skeleton which is one third that of Comparative Example 1, although the number of carbon atoms in the amine skeleton is one third.
- the pH was measured using a handy-type pH meter (manufactured by Mettler Toledo Co., Ltd.) as a CHASS, 5 wt% aqueous solution for DIPEASS, and a 5 wt% dimethyl sulfoxide solution for TOASS, MOASS.
- Comparative Example 1 became a yellow translucent plastic like on the first evaluation day, and it was clear that polymerization was proceeding.
- TOASS was dissolved in dimethylformamide, and GPC analysis was performed using 10 mmol / L lithium bromide dimethylformamide solution as an eluent.
- the aryl sulfonic acid amine salt vinyl monomer of the present invention is an aryl sulfonic acid compound having high purity, high storage stability, and amphiphilic property, and having an oleophilic property such as antistatic of resin and rubber, graft polymerization to polyolefin, etc. It becomes easy to apply aryl sulfonic acid to the required applications, and also in applications requiring a certain degree of water solubility, such as reactive emulsifiers for emulsion polymerization, compared with conventional water-soluble sulfonic acid monomers. As a result, it is possible to improve the production efficiency, so it is extremely useful industrially as a versatile or functional polymer raw material.
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Abstract
Description
または、下記式(2)
下記式(3)
R3、R4およびR5の構造が全て異なるか、又はR3、R4およびR5の内のいずれか2つの構造が同じであり、
R3、R4およびR5は、各々独立して、炭素原子数1~7の直鎖もしくは分岐鎖もしくは環式の飽和炭化水素基、炭素原子数1~7のアリール基または炭素原子数1~7のヒドロキシアルキル基であり、
R3、R4およびR5の内の少なくとも1つが三級炭素もしくは四級炭素を有するか、又は環構造を有し、
前記環構造は、アリール基、5員環もしくは6員環のシクロアルキル基、R3、R4およびR5の内のいずれか2つが互いに結合した5員環もしくは6員環、またはR3、R4およびR5の内のいずれか2つが酸素原子を介して互いに結合した5員環もしくは6員環である。)で表される3級アミンと、
の塩である、アリールスルホン酸アミン塩に係る。
R3、R4およびR5の構造が全て異なるか、又はR3、R4およびR5の内のいずれか2つの構造が同じであり、
R3、R4およびR5は、各々独立して、炭素原子数1~7の直鎖もしくは分岐鎖もしくは環式の飽和炭化水素基、炭素原子数1~7のアリール基または炭素原子数1~7のヒドロキシアルキル基であり、
R3、R4およびR5の内の少なくとも1つが環構造を有し、
前記環構造は、アリール基、5員環もしくは6員環のシクロアルキル基、R3、R4およびR5の内のいずれか2つが互いに結合した5員環もしくは6員環、またはR3、R4およびR5の内のいずれか2つが酸素原子を介して互いに結合した5員環もしくは6員環である、上記のアリールスルホン酸アミン塩に係る。ここで、R3、R4およびR5の内の少なくとも1つが環構造を有することがあるとは、環構造を有すること及び有しないことのいずれも含まれることを言う。
R1は、水素またはエテニル基であり、
R2は、エテニル基、4-エテニルフェニル基又はトリフルオロメチル基である、上記のアリールスルホン酸アミン塩に係る。
下記式(5)
または下記式(6)
または下記式(8)
下記式(9)
本実施形態のアリールスルホン酸アミン塩ビニルモノマーは、下記式(1)または、下記式(2)で表されるアリールスルホン酸と、下記式(3)で表される3級アミンと、の塩であるアリールスルホン酸アミン塩、並びにその重合物である。
R3、R4およびR5は、各々独立して、炭素原子数1~7の直鎖もしくは分岐鎖の飽和炭化水素基、アリール基またはヒドロキシアルキル基であり、
R3、R4およびR5の内の少なくとも1つが該構造中に三級炭素もしくは四級炭素を有するか、又は環構造を有し、
前記環構造は、アリール基、5員環もしくは6員のシクロアルキル基、R3、R4およびR5の内のいずれか2つが互いに結合した5員環もしくは6員環、またはR3、R4およびR5の内のいずれか2つが酸素原子を介して互いに結合した5員環もしくは6員環である。)。
本実施形態のアリールスルホン酸アミン塩ビニルモノマーの製造方法は、特に限定はされないが、その一例として、撹拌機、冷却管、滴下管を取り付けた反応器に、窒素雰囲気下、アリールスルホン酸金属塩の溶液を仕込み、ここに3級アミンの無機酸塩の溶液を滴下し、均一系または2層系にて塩交換を行う方法により製造できる。この際、3級アミン無機酸溶液を反応器に仕込み、アリールスルホン酸金属塩溶液を滴下しても良い。
本実施形態に用いるアリールスルホン酸の具体例としては、芳香環に一つまたは二つのビニル基を有する化合物であれば特に限定はされないが、一般式(1)に示されるパラスチレンスルホン酸、オルトスチレンスルホン酸、メタスチレンスルホン酸、オルトジビニルベンゼンスルホン酸、メタジビニルベンゼンスルホン酸、パラジビニルベンゼンスルホン酸、下記式(2)のR2は具体的に、エテニル基、4-エテニルフェニル基、トリフルオロメチル基、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、1-メチルブチル基、2-メチルブチル基、3-メチルブチル基、1-エチルプロピル基、1,1-ジメチルプロピル基、1,2-ジメチルプロピル基、2,2-ジメチルプロピル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、メチルシクロプロピル基、1-メチルシクロブチル基、2-メチルシクロブチル基、1-メチルシクロペンチル基、2-メチルシクロペンチル基、1-メチルシクロヘキシル基、2-メチルシクロヘキシル基、3-メチルシクロヘキシル基、1,1-ジメチルシクロプロピル基、1,2-ジメチルシクロプロピル基、1,1-ジメチルシクロブチル基、1,2-ジメチルシクロブチル基、1,3-ジメチルシクロブチル基、2,2-ジメチルシクロブチル基等が挙げられ、反応を阻害しない範囲で任意の位置に置換基を有していてもよい。中でも、一般式(1)においては、パラスチレンスルホン酸、パラジビニルベンゼンスルホン酸、メタジビニルベンゼンスルホン酸、一般式(2)のR2においては、エテニル基、4-エテニルフェニル基、トリフルオロメチル基が原料入手の観点から好ましい。
本実施形態に用いる一般式(3)の3級アミンは、前記の通りであるが、中でも、R3、R4およびR5のうち少なくとも一つが5員環または6員環のシクロアルキル基を含むか、R3、R4およびR5の内のいずれか2つ、例えばR3とR4とが互いに結合した5員環または6員環を形成するか、R3、R4およびR5の内のいずれか2つ、例えばR3とR4とが酸素原子を介して互いに結合した5員環または6員環を形成するのが好ましい。また、上記式(3)で表されるアミン化合物は、2つ以上の環構造を含んでいてもよい。
本実施形態で示される高純度アリールスルホン酸アミン塩の単量体を用いた、高純度アリールスルホン酸アミン塩(共)重合体の製造法は、特に限定するものではないが、一般的な塊状重合、溶液重合、分散重合、懸濁重合、乳化重合などのラジカル重合による方法により合成が可能である。
(1)試料の調製
内部標準物質として約0.05重量%のテトラメチルシランを含むジメチルスルホキシド-d6(99.5重量%)またはクロロホルム-d(99.5重量%)約0.7mLに試料を溶解し、NMR測定用サンプルを調製した。
機種=Bruker製AV-400M
積算回数=16
次式によって生成物の純度を算出した。
純度(wt%)=(B/Mb)×(a/aH)/(b/bH)×Ma/S×100
a:任意の目的物ピークの積分値
b:任意の内部標準物質の積分値
aH:aで選択した任意の生成物ピークの水素数
bH:bで選択した任意の生成物ピークの水素数
Ma:目的物の分子量
Mb:内部標準物質の分子量
B:内部標準の採取量(g)
S:試料の採取量(g)
東ソー株式会社製 HLC-8320を用いて重合物の定量(面積%)を行った。試料を水またはアセトニトリルまたはその混合溶媒に溶解し、0.1wt%溶液を調製し、以下の条件でGPC測定を行った。モノマー由来のピーク面積(a)と重合物由来のピーク面積(b)から、下式により重合物の含有量を算出した。
重合物の含有量(面積%)=100×a/(a+b)
カラム=TSK AW6000+AW3000+TSK ガードカラムAW-H
溶離液=硫酸ナトリウム水溶液(0.05mol/L)/アセトニトリル=65/35(Vol比)溶液
又は硫酸ナトリウム水溶液(0.05mol/L)/アセトニトリル=90/10(Vol比)溶液
又は臭化リチウムジメチルホルムアミド溶液(10mmol/L)
流速・注入量・カラム温度=0.6ml/min、注入量=10μl、カラム温度=40℃
検出器=UV検出器(波長230nm)
検量線=標準ポリスチレンスルホン酸ナトリウム(創和科学製)
重合転化率の分析において、GPCによる分析と併せて、株式会社島津製作所製 GC-14Aを用いたモノマーの残存量の定量を行った。分析は、マイクロシリンジでサンプル液を0.2μl注入し、以下の条件で行った。また、内部標準物質を用いて、内部標準物質量とピーク面積%からなる検量線を作成後、モノマー由来のピーク面積と内部標準物質由来のピーク面積から、モノマーの含有量を算出した。下記条件において、スチレンの場合、保持時間(rt)は、17.5minであった。
検出器=FID,キャリアガス:He
カラム=PEG20M Chromosorb WAW 15% 80-100mesh
検出器温度:190℃、INJ温度:200℃
カラム温度:60℃-190℃(5℃/min)
内部標準物質:n-BuOH(rt=13.2min)
〔パラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた200mLガラス製四つ口フラスコに、N、N―ジメチルシクロヘキシルアミン(東京化成工業株式会社製)40.0gを仕込んだ。これを0℃に冷却し、引き続き冷却しながら、35%塩酸(和光純薬工業株式会社製)33.0g、イオン交換水30.0gの混合液を滴下した。滴下終了後、室温で1時間撹拌し、N,N―ジメチルシクロヘキシルアミン塩酸塩の水溶液を得た。
1) 1H-NMR(400MHz、CDCl3):δ10.6(1H,s)、δ7.84(2H,d)、δ7.41(2H,d)、δ6.71(1H,dd)、δ5.78(1H, d)、δ5.29(1H,d)、δ3.06(1H,ddd)、δ2.80(6H,s)、δ2.12(2H,d)、δ1.91(2H,d)、δ1.70(1H,d)、δ1.44-1.25(4H,m)、δ1.19-1.08(1H,m)
〔パラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた100mL四つ口ガラス製フラスコに、4-(2-ブロモエチル)ベンゼンスルホン酸70%水溶液(東ソー有機化学株式会社製)10.0g、N、N―ジメチルシクロヘキシルアミン12.5g、ハイドロキノン(和光純薬工業株式会社製)27mgを仕込んだ。この混合液を90℃に加熱し、そのまま2時間撹拌した。反応終了後、反応液を室温まで冷却し、析出した粗結晶をろ過し、トルエン10g×2回リンスを行い、減圧乾燥することで、パラスチレンスルホン酸N、N―ジメチルシクロヘキシルアミン塩の白色固体6.04g(収率78.4%、純度98.2%)を得た。
〔パラスチレンスルホン酸 N、N―ジイソプロピルエチルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた100mLガラス製四つ口フラスコに、N、N―ジイソプロピルエチルアミン(東京化成工業株式会社製)10.0gを仕込んだ。これを0℃に冷却し、引き続き冷却しながら、35%塩酸(和光純薬工業株式会社製)7.5g、イオン交換水10.0gの混合液を滴下した。滴下終了後、室温で1時間撹拌し、N、N―ジイソプロピルエチルアミン塩酸塩の水溶液を得た。
1H-NMR(400MHz、CDCl3):δ9.52(1H,s)、δ7.78(2H,d)、δ7.33(2H,d)、δ6.64(1H,dd)、δ5.70(1H,d)、δ5.21(1H,d)、δ3.61(2H,m)、δ3.03(2H,q)、δ1.40-1.32(15H,m)
〔ポリ(パラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩)の合成例〕
100mLガラス製四つ口フラスコに、実施例1で得られたパラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩1.5g、イオン交換水13.5gを仕込み、室温で撹拌、溶解した。この溶液を、アスピレーター減圧と窒素導入を繰り返すことで十分に脱気し、2,2’-アゾビス(2-メチルプロピオンアミジン)二塩酸塩(和光純薬工業株式会社製)0.013gを、窒素を吹き込みながら添加した。この溶液を60℃で6時間加熱撹拌し、ポリ(パラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩の透明均一水溶液を得た。反応終了時の重合転化率は100%、数平均分子量は150,000であった。
〔パラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩を用いたスチレンの乳化重合例〕
100mLガラス製四つ口フラスコに、スチレン(和光純薬工業株式会社製)10.0g、実施例1で得られたパラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩0.31g、ドデシルベンゼンスルホン酸ナトリウム(和光純薬工業株式会社製)0.25g、イオン交換水20.5gを仕込み、室温で撹拌、溶解した。この溶液を、アスピレーター減圧と窒素導入を繰り返すことで十分に脱気し、2,2’-アゾビス(2-メチルプロピオンアミジン)二塩酸塩(和光純薬工業株式会社製)0.025gを、窒素を吹き込みながら添加した。この溶液を60℃で24時間加熱撹拌し、スチレンの乳化重合溶液を得た。反応終了時の重合転化率は100%、数平均分子量は200,000であった。
〔ジビニルベンゼンスルホン酸N、N―ジメチルシクロヘキシルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた200mLガラス製四つ口フラスコに、N、N―ジメチルシクロヘキシルアミン40.0gを仕込んだ。これを0℃に冷却し、引き続き冷却しながら、35%塩酸(和光純薬工業株式会社製)33.0g、イオン交換水30.0gの混合液を滴下した。滴下終了後、室温で1時間撹拌し、N,N―ジメチルシクロヘキシルアミン塩酸塩の水溶液を得た。
〔パラスチレンスルホン酸n-トリオクチルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた100mLガラス製四つ口フラスコに、n-トリオクチルアミン(東京化成工業株式会社製)10.0g、n-ヘキサン 40gを仕込み、撹拌、溶解した。この溶液を0℃に冷却し、引き続き冷却しながら、35%塩酸(和光純薬工業製)3.2gを滴下した。滴下終了後、室温で1時間撹拌した。反応終了後、析出したn-トリオクチルアミン塩酸塩をろ過し、減圧乾燥した。
1H-NMR(400MHz、DMSO-d6):δ8.96(1H,s)、δ7.59(1H,d)、δ7.42(2H,d)、δ6.72(1H,dd)、δ5.84(1H,d)、δ5.28(1H,d)、δ3.01(6H,t)、δ1.59-1.56(6H,m)、δ1.29-1.23(30H,m)、δ0.86(9H,t)
〔パラスチレンスルホン酸n-モノオクチルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた200mLガラス製四つ口フラスコに、n-モノオクチルアミン(東京化成工業株式会社製)12.9g、イオン交換水70.5gを仕込んだ。この溶液を0℃に冷却し、引き続き冷却しながら、35%塩酸10.4gを滴下した。滴下終了後、室温で1時間撹拌し、n-モノオクチルアミン塩酸塩の水溶液を得た。
1H-NMR(400MHz、DMSO-d6):δ7.68(2H,s)、δ7.58(2H,d)、δ7.45(2H,d)、δ6.73(1H,dd)、δ5.85(1H,d)、δ5.28(1H,d)、δ2.75(2H,t)、δ1.52-1.47(2H,m)、δ1.27-1.23(10H,m)、δ0.86(3H,t)
〔パラスチレンスルホン酸ジシクロヘキシルアミン塩の合成例〕
還流冷却管、窒素導入管、滴下ロートを取り付けた100mLガラス製四つ口フラスコに、ジシクロヘキシルアミン(東京化成工業株式会社製)10.0g、n-ヘキサン 40gを仕込み、撹拌、溶解した。この溶液を0℃に冷却し、引き続き冷却しながら、35%塩酸(和光純薬工業製)5.6gを滴下した。滴下終了後、室温で1時間撹拌した。反応終了後、析出したジシクロヘキシルアミン塩酸塩をろ過し、減圧乾燥した。
1H-NMR(400MHz、DMSO-d6):δ8.19(1H,s)、δ7.58(2H,d)、δ7.45(2H,d)、δ6.64(1H,dd)、δ5.85(1H,d)、δ5.28(1H,d)、δ3.09(2H,m)、δ1.98(4H,m)、δ1.73(4H,m)、δ1.62-1.59(2H,m)、δ1.28-1.23(8H,m)、δ1.10-1.06(2H,m)
〔パラスチレンスルホン酸n-トリオクチルアミン塩を用いたスチレンの乳化重合例〕
100mLガラス製四つ口フラスコに、スチレン(和光純薬工業株式会社製)10.0g、実施例1で得られたパラスチレンスルホン酸n-トリオクチルアミン塩0.54g、ドデシルベンゼンスルホン酸ナトリウム(和光純薬工業株式会社製)0.25g、イオン交換水20.5gを仕込み、室温で撹拌、溶解した。この溶液を、アスピレーター減圧と窒素導入を繰り返すことで十分に脱気し、2,2’-アゾビス(2-メチルプロピオンアミジン)二塩酸塩0.025gを、窒素を吹き込みながら添加した。この溶液を60℃で24時間加熱撹拌し、スチレンの乳化重合溶液を得たが、反応終了時の重合転化率は30%とモノマーが多く残存する結果となった。また、数平均分子量は50,000であった。
実施例1、3及び比較例1、2、3で得られたパラスチレンスルホン酸アミン塩、市販のパラスチレンスルホン酸ナトリウム塩(東ソー有機化学株式会社製)を加え、評価を以下の通りに行った。なお、下記評価において、パラスチレンスルホン酸 N、N―ジメチルシクロヘキシルアミン塩(CHASS)、パラスチレンスルホン酸 N、N―ジイソプロピルエチルアミン塩(DIPEASS)、パラスチレンスルホン酸n-トリオクチルアミン(TOASS)、パラスチレンスルホン酸n-モノオクチルアミン塩(MOASS)、パラスチレンスルホン酸ジシクロヘキシルアミン塩(DCHASS)、パラスチレンスルホン酸ナトリウム塩(NaSS)の略称を用いる場合がある。
ガラス製スクリュー管瓶に、水、テトラヒドロフラン(THF)、N-メチルピロリドン(NMP)、トルエンをそれぞれ2g加え、25℃でスチレンスルホン酸塩類を少しずつ添加し、手で振り混ぜながら溶解性を確認した。それぞれ、固体が残存した時点を飽和溶解度とし、下記式において溶解度を算出した。溶解性の結果は表2の通りとなった。
溶解度(wt%)= A/(S+A)×100
A:添加したアミンの重量(g)
S:溶媒の重量(g)
ガラス製スクリュー管瓶に、スチレンスルホン酸塩類の固体を2.0g添加し、栓をして密閉系とした後、60℃に設定した箱型乾燥機に設置し、重合安定性の加速試験を実施した。
Claims (8)
- 下記式(1)
または下記式(2)
下記式(3)
R3、R4およびR5の構造が全て異なるか、又はR3、R4およびR5の内のいずれか2つの構造が同じであり、
R3、R4およびR5は、各々独立して、炭素原子数1~7の直鎖もしくは分岐鎖もしくは環式の飽和炭化水素基、炭素原子数1~7のアリール基または炭素原子数1~7のヒドロキシアルキル基であり、
R3、R4およびR5の内の少なくとも1つが三級炭素もしくは四級炭素を有するか、又は環構造を有し、
前記環構造は、アリール基、5員環もしくは6員環のシクロアルキル基、R3、R4およびR5の内のいずれか2つが互いに結合した5員環もしくは6員環、またはR3、R4およびR5の内のいずれか2つが酸素原子を介して互いに結合した5員環もしくは6員環である。)で表される3級アミンと、
の塩である、アリールスルホン酸アミン塩。 - 前記式(3)中、
R3、R4およびR5の構造が全て異なるか、又はR3、R4およびR5の内のいずれか2つの構造が同じであり、
R3、R4およびR5は、各々独立して、炭素原子数1~7の直鎖もしくは分岐鎖もしくは環式の飽和炭化水素基、炭素原子数1~7のアリール基または炭素原子数1~7のヒドロキシアルキル基であり、
R3、R4およびR5の内の少なくとも1つが環構造を有し、
前記環構造は、アリール基、5員環もしくは6員環のシクロアルキル基、R3、R4およびR5の内のいずれか2つが互いに結合した5員環もしくは6員環、またはR3、R4およびR5の内のいずれか2つが酸素原子を介して互いに結合した5員環もしくは6員環である、請求項1に記載のアリールスルホン酸アミン塩。 - 前記式(1)又は(2)中、
R1は、水素またはエテニル基であり、
R2は、エテニル基、4-エテニルフェニル基又はトリフルオロメチル基である、
請求項1又は請求項2に記載のアリールスルホン酸アミン塩。 - パラスチレンスルホン酸とN,N―ジメチルシクロヘキシルアミンとの塩である、請求項1~3のいずれかに記載のアリールスルホン酸アミン塩。
- 請求項1~4のいずれかに記載のアリールスルホン酸アミン塩を重合してなるアリールスルホン酸アミン塩の重合物。
- 請求項1~4のいずれかに記載のアリールスルホン酸アミン塩と溶媒を混和後溶解させ、必要に応じて分子量調節剤や乳化剤を加え、窒素雰囲気下、ラジカル重合開始剤を加え、加熱撹拌して反応させる、アリールスルホン酸アミン塩の重合物の製造方法。
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