JPS62201914A - Production of liquid product containing cationic polymer - Google Patents
Production of liquid product containing cationic polymerInfo
- Publication number
- JPS62201914A JPS62201914A JP4509986A JP4509986A JPS62201914A JP S62201914 A JPS62201914 A JP S62201914A JP 4509986 A JP4509986 A JP 4509986A JP 4509986 A JP4509986 A JP 4509986A JP S62201914 A JPS62201914 A JP S62201914A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- water
- formula
- alkyl group
- meth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920006317 cationic polymer Polymers 0.000 title claims abstract description 10
- 239000012263 liquid product Substances 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 15
- 239000002280 amphoteric surfactant Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000001450 anions Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229960003237 betaine Drugs 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 4
- 125000001033 ether group Chemical group 0.000 claims 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- -1 Inorganic acid salts Chemical class 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000011344 liquid material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000001768 cations Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- JWNWCEAWZGLYTE-UHFFFAOYSA-N 2-(trimethylazaniumyl)butanoate Chemical compound CCC(C([O-])=O)[N+](C)(C)C JWNWCEAWZGLYTE-UHFFFAOYSA-N 0.000 description 1
- HVYJSOSGTDINLW-UHFFFAOYSA-N 2-[dimethyl(octadecyl)azaniumyl]acetate Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC([O-])=O HVYJSOSGTDINLW-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000013054 paper strength agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は水溶性または水分散性のカチオン性ポリマー含
有液状物の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing a water-soluble or water-dispersible cationic polymer-containing liquid product.
従来、水溶性または水分散性のカチオン性ポリマー含有
液状物の製法としては水溶性のカチオン性ビニル単量体
を水溶液重合する方法が最も一般的である。Conventionally, the most common method for producing a water-soluble or water-dispersible cationic polymer-containing liquid product is to carry out aqueous solution polymerization of a water-soluble cationic vinyl monomer.
また２１；の方法としては、水溶性のカチオン性ビニル
単量体の水溶液を非水溶媒（ヘキサン等）の中に乳化さ
せて重合する逆相乳化重合法が公知である。As method 21;, a reverse phase emulsion polymerization method is known, in which an aqueous solution of a water-soluble cationic vinyl monomer is emulsified in a non-aqueous solvent (hexane, etc.) and polymerized.
しかしながら従来の技術で水溶液重合を行った場合、得
られる液状物の粘度が高く、取り扱いが困殖であった。However, when aqueous solution polymerization is carried out using conventional techniques, the resulting liquid product has a high viscosity and is difficult to handle.
殊に水溶性のカチオンポリマーとして高分子量物を製造
しようとする場合には粘度が著しく高いものになってし
まい容器からの数円し時や、他の薬剤との混合、溶解、
塗工などの１実用時に支障をきたすことが多かつｊこ
。In particular, when trying to produce a high molecular weight product as a water-soluble cationic polymer, the viscosity becomes extremely high, making it difficult to remove it from the container, mix it with other drugs, dissolve it, etc.
This often causes problems during practical applications such as coating.
.
また逆相乳化重合法では、非水系の有機溶媒が使用され
、これが？（Ｉられる液状物中に含まれるため性能上不
都合な場合が多く、また価賂的にも水溶液重合品に較べ
て高価になり実用１ｉ１１ｉ （ｉ（ｉが小さい。Also, in the reverse phase emulsion polymerization method, a non-aqueous organic solvent is used. (It is often inconvenient in terms of performance because it is contained in the liquid material containing I, and it is also more expensive than aqueous solution polymerized products.
不発明者らは有機溶媒を用いず高分子弗″でかつ取り扱
い性のすぐれｔコ低粘度で水溶性または水分散性のカチ
オン性ポリマー含有液状物の製造法について検討した結
果本発明に到達した。The present inventors have arrived at the present invention as a result of studying a method for producing a cationic polymer-containing liquid product that does not use an organic solvent, has a high molecular weight, is easy to handle, has a low viscosity, and is water-soluble or water-dispersible. .
すなわち本発明は一般式
（式中、Ｒ１は水素原子まｔ、＝はメチル基：Ｒ２は−
Ｃ１，ＣＨ，−または＝Ｃｌ−１，−ＣＨ−ＣＩ、 −
； Ｉｔ、およびＨ
几、はメチル基またはエチル基；Ｒ９は水素原子、炭素
数１〜４のアルキル基またはベンジル基；Ｘは塩を形成
する陰イオンである。）で示される単量体および、水に
不溶のスチレン類および／または（メタ）アクリレート
類を４級アンモニウム型カチオン界面活性剤または両性
界面活Ｙ１：剤の存在下重合させることを特徴とする水
溶性または水分散性のカチオン性ポリマー含有液状物（
以下本発明の液状物と略記）の製造法である。That is, the present invention is based on the general formula (wherein R1 is a hydrogen atom, = is a methyl group, and R2 is -
C1,CH,- or =Cl-1,-CH-CI, -
; It and H 几 are methyl or ethyl groups; R9 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a benzyl group; X is an anion that forms a salt; ) and water-insoluble styrenes and/or (meth)acrylates are polymerized in the presence of a quaternary ammonium type cationic surfactant or an amphoteric surfactant Y1: or water-dispersible cationic polymer-containing liquid (
This is a manufacturing method of the liquid material of the present invention).
一般式（１）においてＲ，における炭素数１〜４のアル
キル基としてはメチル、エチル、ｎ−または１ｓｕ−プ
ロピル、ローまたは１ｓｕ−ブチル基などがあげられる
。Ｒｓのうち好ましいのは水素原子およびメチル基であ
る。In general formula (1), examples of the alkyl group having 1 to 4 carbon atoms in R include methyl, ethyl, n- or 1su-propyl, rho- or 1su-butyl group, and the like. Preferred among Rs are a hydrogen atom and a methyl group.
Ｘ の塩を形成する陰イオンとしては、ノ）ロゲンイオ
ン（Ｃ１！、Ｂ＋ など）、ＣＨ，０８０３、Ｃ，Ｉ
−１，Ｏ２０，、ｔｌｓＯ，、Ｈ，ＰＯ，、Ｃ１，ＣＯ
，、ＨＣＯ，。Examples of anions that form salts of
-1,O20,,tlsO,,H,PO,,C1,CO
,,HCO,.
Ｃｌ−１，Ｃ，Ｈ，、ＳＯ，、ＮＯ，−などがあげられ
る。Ｘ のうち好ましいものは、ノ１０ゲンイオン、ｃ
ｒｉ、ｏｓｏ、。Examples include Cl-1, C, H, SO, NO, -, and the like. Among X, preferable ones are genion, c
ri, oso,.
および！−ＩＳＯ，である。and! -ISO.
一般式（１”ｌで示されるＩ（Ｌ （７ｉ体の具体的な
例としては、ジアルキルアミノアルキル（メタ）アクリ
レート類〔ジメチルアミノエチル（メタ）アジリレート
、ジエチルアミノエチル（メタ）アクリレート、３−ジ
メチルアミノ−２−ヒドロキシプロピル（メタ）アクリ
レートなど１の無機酸塩（塩酸塩、硫酸塩、硝酸塩など
）、有機酸塩（酢酸塩、蟻酸塩など）または４級化剤（
塩化メチル、ジメチル硫酸、塩化ベンジルなど）による
第四級アンモニウム塩があげられる。I(L represented by the general formula (1"l) Inorganic acid salts (hydrochloride, sulfate, nitrate, etc.), organic acid salts (acetate, formate, etc.) or quaternizing agents (such as amino-2-hydroxypropyl (meth)acrylate)
Quaternary ammonium salts include methyl chloride, dimethyl sulfate, benzyl chloride, etc.).
これらの中で好ましいものは、本発明における共重合体
の品質上から、ジアルキルアミノアルキル（メタ）アク
リレート類の第４級アンモニウム塩である。Among these, quaternary ammonium salts of dialkylaminoalkyl (meth)acrylates are preferred from the viewpoint of the quality of the copolymer in the present invention.
水に不溶のスチレン類としては一般式
％式％（４）
（式中、ＲｏおよびＢ＋ａは水素原子またはメチル基で
ある）で示される単量体があげられる。Examples of water-insoluble styrenes include monomers represented by the general formula % (4) (wherein Ro and B+a are hydrogen atoms or methyl groups).
一般式（４）で示される単量体の具体的な例としては、
水に対する溶解度（２５℃）が水１． ＯＯ７に対して
２０７以下のモノビニルモノマー。Specific examples of the monomer represented by general formula (4) include:
Solubility in water (25°C) is 1. Monovinyl monomer of 207 or less relative to OO7.
例エバスチレン、σ−メチルスチレンおよびビニルトル
エンがあげられる。Examples include evastyrene, σ-methylstyrene and vinyltoluene.
これらの中で好ましいものは本発明における共重合体の
品７７ｊ上から、水に対する溶解度（２５℃）が水ｘｏ
（＋５１に対して０５ｙ以下のビニルモノマー例えばス
チレンである。Among these, preferable copolymers according to the present invention have a solubility in water (at 25° C.) of the copolymer product 77j.
(A vinyl monomer of 05y or less for +51, for example, styrene.
水に不溶の（メタ）アクリレート類としては一般式
％式％
（式中、Ｒ＋ ＋は水素原子またはメチル基； ＲＨは
炭素数１〜１８のアルキル基である。）で示される単量
体があげられる。Examples of water-insoluble (meth)acrylates include monomers represented by the general formula % (wherein R+ is a hydrogen atom or a methyl group; RH is an alkyl group having 1 to 18 carbon atoms). can give.
一般式（５）においてｎｅｔにおける炭素数１〜１８の
アルキル基としては、メチル、エチル、ｎ−または１ｓ
ｕ−プロピル、ローブチル、２−エチルヘキシル
ル基などがあげられる．Ｒ１，のうち好ましいのはメチ
ル、エチル、【］−ブチルおよび２−エチルヘキシル基
である９
一般式（５）で示される単量体の具体的な例としては水
に対する溶解度（２５℃）が水１ ０ ０ノに対して２
． ０ 、９以下のモノビニルモノマー、例えばアルキ
ル（メタ）アクリレート類〔メチル（メタ）アクリレー
ト、エチル（メタ）アクリレート、ブチル（メタ）アク
リレート、２−エチルヘキシル（メタ）アクリレートな
ど〕があげられる。In general formula (5), the alkyl group having 1 to 18 carbon atoms in net is methyl, ethyl, n- or 1s
Examples include u-propyl, lobethyl, and 2-ethylhexyl groups. Preferred among R1 are methyl, ethyl, []-butyl and 2-ethylhexyl groups.9 Specific examples of monomers represented by general formula (5) include water solubility (at 25°C). 2 for 1 0 0 no
．． Examples include monovinyl monomers having a molecular weight of 0.0, 9 or less, such as alkyl (meth)acrylates [methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, etc.].
これらの中で好ましいものは同じ理由で水に対する溶解
度（２５℃）が水ｉｏｏｙに対し、０、 ５ ｙ以下の
モノビニルモノマー例えばブチルメタクリレートおよび
２−エチルへキシルメタクリレートである。For the same reason, preferred among these are monovinyl monomers such as butyl methacrylate and 2-ethylhexyl methacrylate whose solubility in water (25° C.) is 0.5 y or less relative to water iooy.
本発明においては、一般式（１）で示される単量体、水
に不溶のスチレン類および，／まｔ：は（メタ）アクリ
レート類の４ｔ＋Ｊ％必要に応じて他の単量体を共重合
させることができる。In the present invention, 4t+J% of the monomer represented by general formula (1), water-insoluble styrenes, and/or (meth)acrylates are copolymerized with other monomers as necessary. can be done.
仙の単ｆｆｉ体としては、例えばアクリルアミド、酢醜
・ビニル、アクリロ；トリル、ビニルピロリドン、ヒド
ロキシエチル（メタ）アクリレ− トなどのノニオン性
ビニルモノマー；２−アクリルアミド−２．２−ジメチ
ルエタンスルホン酸ソーダ、ビニルスルホン酸ソーダ、
（メタ）アクリル酸ソーダなどのアニホン性ビニルモノ
マー；ビニルピリジン、ジアリルジメチルアンモニウム
クロライド、アリルアミン、スチリルトリメチルアンモ
ニウムクロライドなどのカチオン性ビニルモノマーなど
があげられる。Examples of monomers include acrylamide, vinyl, acrylo; nonionic vinyl monomers such as tolyl, vinylpyrrolidone, and hydroxyethyl (meth)acrylate; 2-acrylamide-2,2-dimethylethanesulfonic acid; soda, vinyl sulfonic acid soda,
Examples include aniphonic vinyl monomers such as sodium (meth)acrylate; cationic vinyl monomers such as vinylpyridine, diallyldimethylammonium chloride, allylamine, and styryltrimethylammonium chloride.
これらの中では、ｔｌ能面から、好ましいものはノニオ
ン性およびカチオン性ビニルモノマーである。Among these, preferred are nonionic and cationic vinyl monomers from the viewpoint of tl performance.
・１級アンモニウム型カチオン界面活性剤としては一般
式
（式中、ルは炭素数８〜１８のアルキル基、炭素数８〜
２４のアリール基または炭素数１２〜２ ｌｌのアミド
アルキル基；ｌは炭素数１〜１８のアルキル基である。・The primary ammonium type cationic surfactant has the general formula (in the formula, R is an alkyl group having 8 to 18 carbon atoms,
24 aryl group or amide alkyl group having 12 to 2 1 carbon atoms; 1 is an alkyl group having 1 to 18 carbon atoms.
）で示されるカチオン界面活性剤および／または一般式
（式中、Ｒ・は炭素数８〜１８のアルキル基、炭素数８
〜２４のアリール基または炭素数１２〜２４のアミドア
ルキル基；Ｌは炭素数１〜１８のアルキル基である．）
で示されるカチオン界面活性剤があげられる。) and/or a cationic surfactant represented by the general formula (wherein R. is an alkyl group having 8 to 18 carbon atoms;
~24 aryl group or amide alkyl group having 12 to 24 carbon atoms; L is an alkyl group having 1 to 18 carbon atoms. )
Examples include cationic surfactants shown in
一般式（２）および（３）においてＲ．およびＲ，にお
ける炭素数１２〜１８のアルキルジにとしては、ドデシ
ル（ラウリル）、セチル、ステアリル基などがあげられ
る。In general formulas (2) and (3), R. Examples of the alkyl di having 12 to 18 carbon atoms in and R include dodecyl (lauryl), cetyl, and stearyl groups.
炭素数８〜２４のアリール基としてはオクチルフェニル
、ドデシルフェニル、セチルフェニル、ステアリルフェ
ニル基などのアルカリール基；ラウリルベンジル基など
のアラルキル基などがあげられる．炭素数１２〜２・ｌ
のアミドアルキル基としてはステアラ°ミドメチル琴な
どがあげられる。Examples of the aryl group having 8 to 24 carbon atoms include alkaryl groups such as octylphenyl, dodecylphenyl, cetyl phenyl, and stearyl phenyl groups; and aralkyl groups such as laurylbenzyl group. Carbon number 12-2・l
Examples of the amidoalkyl group include stearamidomethylkoto.
■．およびＲ，のうち好ましいものはラウリル、セチル
、ステアリル、およびラウリルベンジル基である。■． and R, preferred are lauryl, cetyl, stearyl, and laurylbenzyl groups.
一般式（３＞においてんにおける炭素数１〜１８のアル
キル基としては、メチル、エチル、【１−または１ｓｕ
−プロピル、＋１−ブチル、デシル、ドデシル、ステア
リル基などがあげられる。In the general formula (3>, the alkyl group having 1 to 18 carbon atoms is methyl, ethyl, [1- or 1su
Examples include -propyl, +1-butyl, decyl, dodecyl, and stearyl groups.
Ｒ２８のうち好ましいものはメチルおよびステアリル基
である。Among R28, preferred are methyl and stearyl groups.
一般式（２）で示されるカチオン界面活１テ１：剤の具
体例としてはピリジン誘導体、例えばアルキルまたはア
ミドアルキルピリジニウムクロライド（ラウリルピリジ
ニウムクロライド、セチル、ピリジニウムクロライド、
ステアラミドメチルピリジニウムクロライドなど）があ
げられる５一般式（：））で示されるカチオン界面活性
剤の具体例としては長鎖アルキル基または長鎖アミドア
ルキル暴含有アンモニウムクロライド、例えばステアリ
ルトリメチルアンモニウムクロライド、ラウリルトリメ
チルアンモニウムクロライドおよびラウリルベンジルト
リメチルアンモニウムクロライドがあげられる。これら
のカチオン界面活性剤のうち好ましいものは、ラウリル
ピリジニウムクロライドおよびセチルヒリジニウムクロ
ライドである。Specific examples of the cationic surfactant represented by formula (2) include pyridine derivatives, such as alkyl or amidoalkylpyridinium chloride (laurylpyridinium chloride, cetyl, pyridinium chloride,
Examples of cationic surfactants represented by the general formula (:)) include ammonium chloride containing long-chain alkyl groups or long-chain amide alkyl groups, such as stearyltrimethylammonium chloride, lauryl trimethylammonium chloride, etc. Mention may be made of trimethylammonium chloride and laurylbenzyltrimethylammonium chloride. Preferred among these cationic surfactants are laurylpyridinium chloride and cetylhyridinium chloride.
両性界面活性剤としては、・を級アンモニウ／、塩型の
カチオン部分とカルホン酸塩型のアニオン部分とをもつ
ペタ１ノ型両性界而活１’ｊｌＥ剤があげられる。Examples of the amphoteric surfactant include amphoteric surfactants having a salt-type cation moiety and a carphonate-type anion moiety.
ベタイン型両性界面活ｆＬ剤としては、一般式（式中、
Ｒ９は炭素数１２〜１８のアルキル基、炭素数１２〜２
４のアリール基または炭素数１２〜２４のアミドアルキ
ル基； １１．、、は炭素数１〜４のアルキル基または
ベンジル基またはヒドロキシエチル基である。）で示さ
れる両Ｙ１！界面活性剤があげられる。As the betaine type amphoteric surfactant fL agent, the general formula (in the formula,
R9 is an alkyl group having 12 to 18 carbon atoms, and 12 to 2 carbon atoms.
4 aryl group or amide alkyl group having 12 to 24 carbon atoms; 11. , , is an alkyl group having 1 to 4 carbon atoms, a benzyl group, or a hydroxyethyl group. ) Both Y1! Examples include surfactants.
一般式（６）において心における炭素数１２〜１８のア
ルキル基としては、ドデシル（ラウリル）、セチル、ス
テアリルＪｌ（などがあげられる、炭素数１２〜２４の
アリール基としテハオクチルフェニル、トテンルフェニ
ル、セチルフェニル、ステアリルフェニル基などのアル
カリール基；ラウリルベンジル基などのア初５
フキル基などがあげられる。In general formula (6), the alkyl group having 12 to 18 carbon atoms at the core includes dodecyl (lauryl), cetyl, stearyl Jl (etc.), and the aryl group having 12 to 24 carbon atoms such as tehaoctylphenyl and totenulfenyl. , cetyl phenyl, stearyl phenyl, and other alkaryl groups; and laurylbenzyl and other 5-phyl groups.
炭素数１２〜２４のアミドアルキル基としてはステアラ
ミトメチル基およびラウリルアミドプロピル基などがあ
げられる。Examples of the amide alkyl group having 12 to 24 carbon atoms include a stearamitomethyl group and a laurylamide propyl group.
Ｒ９のうち好ましいものはラウリル、ステアリルおよび
ラウリルアミド１０ビル基である。Preferred among R9 are lauryl, stearyl and laurylamide 10vir groups.
一般式（６）において１１．ｌｏにおける炭素数１〜４
のアルキル基としては、メチル、エチル、ｎ−または１
ｓｕ−プロピル、 １１−ブチル基などがあげられる。In general formula (6), 11. carbon number 1-4 in lo
As the alkyl group, methyl, ethyl, n- or 1
Examples include su-propyl and 11-butyl groups.
亀４．のうち好ましいものはメチルおよびヒドロキシエ
チル基である。Turtle 4. Preferred among these are methyl and hydroxyethyl groups.
両ｔ５１＝界面活性剤の具体例としては、ラウリルジメ
チルベタイン、ステアリルジメチルベタイン、ドデシル
フェニルジメチルベタイン、ステアラミドメチルジメチ
ルベクイン、ラウリルアミドプロピルジメチルベタイン
、およびラウリルンヒドロキンエチルベタインがあけ゛
られる。Specific examples of surfactants include lauryl dimethyl betaine, stearyl dimethyl betaine, dodecylphenyl dimethyl betaine, stearamide methyl dimethyl betaine, laurylamide propyl dimethyl betaine, and lauryl hydroquine ethyl betaine.
これらの両性界面活性剤のうち好ましいものは、ラウリ
ルジメチルベタインおよびラウリルアミドプロピルジメ
チルベタインである。Preferred among these amphoteric surfactants are lauryl dimethyl betaine and laurylamidopropyl dimethyl betaine.
本発明を実施するに際し、一般式（］、 ）の単１１１
体の量は全単量体の合計モル数にｈ（づいて迫１常２０
〜９０％、好ましくは４０〜８０％である。When carrying out the present invention, the single 111 of the general formula (], )
The amount of monomers is calculated by adding h to the total number of moles of all monomers.
~90%, preferably 40-80%.
一般式（１）の単量体のモル％が、２０％未満では得ら
れる共重合体の水溶性が乏しくなる場合があり、目的と
する性能が得られないことがある。また、９０％を越え
ると、共重合体の粘度が急激に上昇し、取扱性が不良に
なる場合がある。If the mole % of the monomer of general formula (1) is less than 20%, the resulting copolymer may have poor water solubility, and the desired performance may not be obtained. Moreover, if it exceeds 90%, the viscosity of the copolymer may increase rapidly, resulting in poor handling properties.
スチレン類および／または（メタ）アクリレート類の量
は全１ｉ量体の合計モル数に基づいて通常１０〜８０％
、好ましくは２０〜６０％である。The amount of styrenes and/or (meth)acrylates is usually 10-80% based on the total number of moles of all 1i-mers.
, preferably 20 to 60%.
スチレン類および／または（メタ）アクリレート力１の
モル％が１ ｆＪ％未満では共重合体の粘度が高く取扱
性が不良になり、また８（）％を越えると共重合体の水
溶性が乏しくなる６他の単量体の量は全単量体の合計モ
ル数に基づいて５０％以下、好ましくは２（）％以下で
ある。５０％を越えると、本発明におけるンｆり状物が
経［１的に相分離したり、充分な性能が７ＩＩられない
場合が多い。If the mol% of styrene and/or (meth)acrylate force 1 is less than 1 fJ%, the viscosity of the copolymer will be high and handling will be poor, and if it exceeds 8%, the water solubility of the copolymer will be poor. The amount of the other monomers is 50% or less, preferably 2()% or less, based on the total number of moles of all monomers. If it exceeds 50%, the resin-like material used in the present invention often undergoes phase separation or fails to exhibit sufficient performance.
４級アンモニウム塩型カチオン界面活性剤および両ｔＩ
ｌ：界面活性剤の量は、得られる液状物のＰ１゛能、粘
度、経日安定性から全１１１量体の合計型Ｌ；に基づい
て通常０（）５〜２（）％、好ましくは０５〜１．０％
である。Quaternary ammonium salt type cationic surfactant and both tI
l: The amount of surfactant is usually 0 () 5 to 2 () %, preferably 0 () 5 to 2 () %, based on the total type L of all 111-mers from the P1 ability, viscosity, and stability over time of the obtained liquid product. 05-1.0%
It is.
本発明における液状物は水溶液重合によ−）で容易に得
られる。その実ａ＋法は、特に限定なく、公知の方法、
条件等をとり得る０例えば、所定の単量体、４級アンモ
ニウム塩型カチオン界面活性剤または両性界面活性剤お
よび水を重合器に入れて、系を窒素で置換した後、触媒
を加えて重合させればよい、この際、単Ｒ）・体や水の
一部の重合途中での添加、あるいは最初からｆ蛭媒を加
えておく等の変法を採月１してもよい。The liquid material in the present invention can be easily obtained by aqueous solution polymerization. The actual a+ method is not particularly limited, and is a known method,
For example, put a specified monomer, a quaternary ammonium salt type cationic surfactant or an amphoteric surfactant, and water into a polymerization vessel, replace the system with nitrogen, and then add a catalyst to polymerize. In this case, a modified method such as adding a part of the monomer R) or water during the polymerization, or adding a leech medium from the beginning may be used.
上記の触媒としては公知の重合触媒〔過硫酸塩たとえば
、過硫酸アンモニウム、過硫酸カリウム；有機過酸化物
たとえば、ベンゾイルパーオキシド、ｔ−プチルヒドロ
バーオギシド、クメンヒドロバ−オキシド：アゾ化合物
ｔことえは２．２′−アゾビス−（２〜アミジノプロパ
ン）ハイドロクロライド、アゾビスシアツウ゛アレリン
酸およびレドックス触媒たとえば過酸化物または過硫酸
塩（Ｈ，Ｑ、、過硫酸カリウムなど）と還元剤（重す；
）硫酸ソー タ、アヌコルビン酸など）との組合せ〕な
どがあげられる。これらの中で好ましいものはアゾ化合
物触媒およびレドックス触媒である。The above-mentioned catalysts include known polymerization catalysts [persulfates such as ammonium persulfate, potassium persulfate; organic peroxides such as benzoyl peroxide, t-butylhydroboroxide, cumene hydroperoxide; azo compounds; 2. 2'-Azobis-(2-amidinopropane) hydrochloride, azobiscyallelic acid and redox catalysts such as peroxides or persulfates (H, Q, potassium persulfate, etc.) and reducing agents (heavily vinegar;
) sulfuric acid sorter, anucorbic acid, etc.)). Among these, preferred are azo compound catalysts and redox catalysts.
触媒の量は金手Ｓ１体（純分）の重ｈ；に基づいて通常
ＯＯυ５〜５０％、好ましくは０（）１〜０５％である
。The amount of the catalyst is usually OOυ5 to 50%, preferably 0()1 to 05%, based on the weight h of the Kanade S1 body (pure content).
重合温度は通常２０〜１ｏ＋ｉ℃、好ましくは４０〜８
（）℃であり、重合時間は通常１〜１２時間、好ましく
は３〜１０時間である。Polymerization temperature is usually 20-1o+i℃, preferably 40-8℃
()°C, and the polymerization time is usually 1 to 12 hours, preferably 3 to 10 hours.
このようにして白濁１１．た外観の半乳化社の流動性あ
る本発明における液状物が得ら打る。In this way, cloudiness 11. A semi-emulsified liquid with a semi-emulsified appearance and a fluidity according to the present invention is obtained.
このようにして得られる本発明における液状物は一般に
そのまま使用に供することができるが、必要（こ応じて
希釈、濃縮、その他の二次操作を行ってもよい。The liquid product of the present invention obtained in this way can generally be used as is, but dilution, concentration, and other secondary operations may be performed as necessary.
不発明における共重合体の分子量は、本発明における液
状物の目的、用途によって任意に選ぶことができるが、
ｌＮＮａＮ０１中、３０℃で測定した固有粘度が通常０
２以」−２好ましくは１（）以−Ｌである。The molecular weight of the copolymer in the invention can be arbitrarily selected depending on the purpose and use of the liquid product in the invention, but
Intrinsic viscosity measured at 30°C in lNNaN01 is usually 0.
2 or more"-2, preferably 1() or more-L.
本発明（こおける液状物中シこ占める共重合体の濃度は
通常１０〜８０重量％、好ましくは３０〜７（）重量用
である。この範囲を上廻ると濃度が低くすぎて実用価値
が小さくなり、１廻ると液状物の粘７度が高くな−）で
取り扱いが難しくなる。The concentration of the copolymer in the liquid of the present invention is usually 10 to 80% by weight, preferably 30 to 7% by weight.If it exceeds this range, the concentration is too low to be of practical value. It becomes smaller and after one rotation, the viscosity of the liquid becomes high (7), making it difficult to handle.
本発明における液状物には必要に応じ、無機塩（ボウ硝
、硫安、リン酸ソーダ、硫酸アルミなど）、他の界面活
性剤（ポリオキシエチレンノニルフェニルエーテル、ヤ
シ油脂肪酸アルキロールアミド、ソルビタンモノラウレ
ート等）、他の水溶性ポリマー（カナオンデンプン、ポ
リ（、ｓ＋
〔実施例〕
以下実施例および比軸例により本発明をさらに説明する
が、本発明はこれに限定されるものではない。The liquid material used in the present invention may contain inorganic salts (sulfur salt, ammonium sulfate, sodium phosphate, aluminum sulfate, etc.), other surfactants (polyoxyethylene nonylphenyl ether, coconut oil fatty acid alkylolamide, sorbitan monomer, etc.) as necessary. laurate, etc.), other water-soluble polymers (Kanaon starch, poly(, s+ [Example]) The present invention will be further explained below with reference to Examples and ratio examples, but the present invention is not limited thereto. .
起施例１〜４、比較例１〜２
ライド（ＬＩ’ＣＪ）またはラウリルアミドプロピルジ
メチルベタイン（ＬＡＩ’Ｂ ）からなる混合液を表−
１に示す重量比にてｌｊ？のセパラブルフラスコに入れ
攪拌しなから６（＋’ｃにシ（温し、ついで窒素を液中
に１５分間吹きこみ後、２．２’−アゾビス（２−７ミ
ジノブロバン）塩酸塩をそれぞれ対モノマー純分あたり
０２重量％加え、１０時間攪拌を続けた。得られた本発
明および比較液状物の性状および粘度を表−１に示すが
比較例１．２では液状で取り扱いγ１゛のすぐれる水溶
性のカチオンポリマーは得られなかった。Examples 1 to 4, Comparative Examples 1 to 2 Mixed liquids consisting of LIDE (LI'CJ) or laurylamide propyl dimethyl betaine (LAI'B)
At the weight ratio shown in 1, lj? Pour into a separable flask and heat to 6°C while stirring. After blowing nitrogen into the liquid for 15 minutes, add 2,2'-azobis(2-7midinobroban) hydrochloride to each solution. 0.2% by weight based on the pure monomer content was added and stirring was continued for 10 hours.The properties and viscosity of the obtained liquids of the present invention and comparison are shown in Table 1. No water-soluble cationic polymer was obtained.
本発明により高濃度でしかも低粘度の水溶γにまたは水
分散性のカチオンＶ１：、ポリマー含イｊ液状物が得ら
れる。このものはＷ１０エマルシ３ン状のカチオンポリ
マー含有ｊ？ＩＩ成物の様に有機溶剤を含むことなく粉
末品の様に発塵性や吸湿性がない。かつ高濃度でありな
がら従来の水溶液状品１ζ比べ著しく低粘度であり作業
性、取り扱い性が容易である。According to the present invention, a high concentration and low viscosity water-soluble or water-dispersible cation V1:, polymer-containing liquid material can be obtained. This product contains W10 emulsion-like cationic polymer. Unlike II products, it does not contain organic solvents, and unlike powder products, it does not generate dust or absorb moisture. Although it has a high concentration, it has a significantly lower viscosity than the conventional aqueous solution 1ζ, making it easy to work with and handle.
上記効果を奏することから不発明における液状物は、紙
力増強剤、サイズ剤、抄紙有料の歩留り向上剤、帯電防
＋ｈ剤、導電剤および水処Ｉｌｌ剤として極めて良好な
性能を有するものである。Due to the above effects, the liquid material according to the invention has extremely good performance as a paper strength agent, sizing agent, retention improver for paper making, antistatic +H agent, conductive agent, and water treatment Ill agent. .
まｔコその他土頃改良剤、繊維用糊剤、増粘剤および種
子等の固着剤として有用であり工業的価値が高い。It is useful as a soil improver, fiber glue, thickener, and fixing agent for seeds, etc., and has high industrial value.
Claims (1)
Ｈ＿２ＣＨ＿２−または▲数式、化学式、表等がありま
す▼；Ｒ＿３およびＲ＿４はメチル基またはエテル基；
Ｒ＿５は水素原子、炭素数１〜４のアルキル基またはベ
ンジル基；Ｘは塩を形成する陰イオンである。）で示さ
れる単量体および、水に不溶のスチレン類および／また
は（メタ）アクリレート類を４級アンモニウム型カチオ
ン界面活性剤または両性界面活性剤の存在下重合させる
ことを特徴とする水溶性または水分散性のカチオン性ポ
リマー含有液状物の製造法。 ２、４級アンモニウム型カチオン界面活性剤が一般式 ▲数式、化学式、表等があります▼（２） （式中、Ｒ＿６は炭素数８〜１８のアルキル基、炭素数
８〜２４のアリール基または炭素数 １２〜２４のアミドアルキル基である。）で示されるカ
チオン界面活性剤および／または一般式 ▲数式、化学式、表等があります▼（３） （式中、Ｒ＿７は炭素数８〜１８のアルキル基、炭素数
８〜２４のアリール基または炭素数 １２〜２４のアミドアルキル基；Ｒ＿８は炭素数１〜１
８のアルキル基である。）で示されるカチオン界面活性
剤である特許請求の範囲第１項記載の製造法。 ３、両性界面活性剤がベタイン型両性界面活性剤である
特許請求の範囲第１項記載の製造法。[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the formula, R_1 is a hydrogen atom or a methyl group; R_2 is -C
H_2CH_2- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼; R_3 and R_4 are methyl or ether groups;
R_5 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a benzyl group; X is an anion that forms a salt. ) and water-insoluble styrenes and/or (meth)acrylates in the presence of a quaternary ammonium type cationic surfactant or an amphoteric surfactant. A method for producing a water-dispersible cationic polymer-containing liquid product. The general formula for secondary and quaternary ammonium type cationic surfactants is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) (In the formula, R_6 is an alkyl group having 8 to 18 carbon atoms, an aryl group having 8 to 24 carbon atoms, or Cationic surfactant and/or general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (3) (In the formula, R_7 is an amide alkyl group having 8 to 18 carbon atoms.) Alkyl group, aryl group having 8 to 24 carbon atoms, or amidoalkyl group having 12 to 24 carbon atoms; R_8 is 1 to 1 carbon atoms
8 alkyl group. ) The manufacturing method according to claim 1, wherein the cationic surfactant is a cationic surfactant represented by: 3. The manufacturing method according to claim 1, wherein the amphoteric surfactant is a betaine type amphoteric surfactant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61045099A JPH0649738B2 (en) | 1986-02-28 | 1986-02-28 | Method for producing liquid containing cationic polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61045099A JPH0649738B2 (en) | 1986-02-28 | 1986-02-28 | Method for producing liquid containing cationic polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62201914A true JPS62201914A (en) | 1987-09-05 |
| JPH0649738B2 JPH0649738B2 (en) | 1994-06-29 |
Family
ID=12709849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61045099A Expired - Fee Related JPH0649738B2 (en) | 1986-02-28 | 1986-02-28 | Method for producing liquid containing cationic polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0649738B2 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51148682A (en) * | 1975-06-16 | 1976-12-21 | Nitto Chem Ind Co Ltd | Process for prodaction of latex type flocculant |
| JPS5276392A (en) * | 1975-12-22 | 1977-06-27 | Mitsubishi Chem Ind Ltd | Preparation of water-soluble cationic polymers |
| JPS6096611A (en) * | 1983-10-05 | 1985-05-30 | ナシヨナル・スターチ・アンド・ケミカル・コーポレイシヨン | Polymer latex based on cationic vinyl ester, manufacture and use as formaldehyde-free binder |
-
1986
- 1986-02-28 JP JP61045099A patent/JPH0649738B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51148682A (en) * | 1975-06-16 | 1976-12-21 | Nitto Chem Ind Co Ltd | Process for prodaction of latex type flocculant |
| JPS5276392A (en) * | 1975-12-22 | 1977-06-27 | Mitsubishi Chem Ind Ltd | Preparation of water-soluble cationic polymers |
| JPS6096611A (en) * | 1983-10-05 | 1985-05-30 | ナシヨナル・スターチ・アンド・ケミカル・コーポレイシヨン | Polymer latex based on cationic vinyl ester, manufacture and use as formaldehyde-free binder |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0649738B2 (en) | 1994-06-29 |
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