JPH02269715A - Cationic emulsion - Google Patents
Cationic emulsionInfo
- Publication number
- JPH02269715A JPH02269715A JP1092244A JP9224489A JPH02269715A JP H02269715 A JPH02269715 A JP H02269715A JP 1092244 A JP1092244 A JP 1092244A JP 9224489 A JP9224489 A JP 9224489A JP H02269715 A JPH02269715 A JP H02269715A
- Authority
- JP
- Japan
- Prior art keywords
- emulsion
- acrylate
- monomer
- acid
- polymerization
- 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.)
- Pending
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 27
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 28
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 15
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000003839 salts Chemical group 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 15
- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract description 3
- 239000003505 polymerization initiator Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 description 17
- 238000011156 evaluation Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- -1 di-n-butylamino Chemical group 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000003093 cationic surfactant Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- GSOOPMVLNGQEPJ-UHFFFAOYSA-N 2-methylidenepentanamide;n-methylmethanamine Chemical compound CNC.CCCC(=C)C(N)=O GSOOPMVLNGQEPJ-UHFFFAOYSA-N 0.000 description 2
- HDWNKEWYEDOKIZ-UHFFFAOYSA-N 5-(diethylamino)-2-methylidenepentanamide Chemical compound CCN(CC)CCCC(=C)C(N)=O HDWNKEWYEDOKIZ-UHFFFAOYSA-N 0.000 description 2
- GXWNNGGUTQVSAR-UHFFFAOYSA-N 5-(dipropylamino)-2-methylidenepentanamide Chemical compound CCCN(CCC)CCCC(=C)C(N)=O GXWNNGGUTQVSAR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- UOZJCRSVUOQDNJ-UHFFFAOYSA-N 2-(dibutylamino)ethyl prop-2-enoate Chemical compound CCCCN(CCCC)CCOC(=O)C=C UOZJCRSVUOQDNJ-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- HPGIOSOCXHTQGW-UHFFFAOYSA-N 2-(dipropylamino)ethyl prop-2-enoate Chemical compound CCCN(CCC)CCOC(=O)C=C HPGIOSOCXHTQGW-UHFFFAOYSA-N 0.000 description 1
- YICILWNDMQTUIY-UHFFFAOYSA-N 2-methylidenepentanamide Chemical compound CCCC(=C)C(N)=O YICILWNDMQTUIY-UHFFFAOYSA-N 0.000 description 1
- NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-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
- SYRNSZXGMVNJOL-UHFFFAOYSA-N 3-(dibutylamino)propyl prop-2-enoate Chemical compound CCCCN(CCCC)CCCOC(=O)C=C SYRNSZXGMVNJOL-UHFFFAOYSA-N 0.000 description 1
- XUYDVDHTTIQNMB-UHFFFAOYSA-N 3-(diethylamino)propyl prop-2-enoate Chemical compound CCN(CC)CCCOC(=O)C=C XUYDVDHTTIQNMB-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- CPQWVOLUENESHH-UHFFFAOYSA-N 3-(dipropylamino)propyl prop-2-enoate Chemical compound CCCN(CCC)CCCOC(=O)C=C CPQWVOLUENESHH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GOGZPUCPMSMANS-UHFFFAOYSA-N 4-(dibutylamino)butyl prop-2-enoate Chemical compound CCCCN(CCCC)CCCCOC(=O)C=C GOGZPUCPMSMANS-UHFFFAOYSA-N 0.000 description 1
- WZISPVCKWGNITO-UHFFFAOYSA-N 4-(diethylamino)-2-methylidenebutanamide Chemical compound CCN(CC)CCC(=C)C(N)=O WZISPVCKWGNITO-UHFFFAOYSA-N 0.000 description 1
- MWAOKSKBAQCZDC-UHFFFAOYSA-N 4-(dipropylamino)-2-methylidenebutanamide Chemical compound CCCN(CCC)CCC(=C)C(N)=O MWAOKSKBAQCZDC-UHFFFAOYSA-N 0.000 description 1
- XLMXVBKNBILMBW-UHFFFAOYSA-N 4-(dipropylamino)butyl prop-2-enoate Chemical compound CCCN(CCC)CCCCOC(=O)C=C XLMXVBKNBILMBW-UHFFFAOYSA-N 0.000 description 1
- PZMZEVXHRBCILK-UHFFFAOYSA-N 5-(dibutylamino)-2-methylidenepentanamide Chemical compound CCCCN(CCCC)CCCC(=C)C(N)=O PZMZEVXHRBCILK-UHFFFAOYSA-N 0.000 description 1
- ALXUOLQRSSGTMU-UHFFFAOYSA-N 6-(diethylamino)-2-methylhex-2-enamide Chemical compound CCN(CC)CCCC=C(C)C(N)=O ALXUOLQRSSGTMU-UHFFFAOYSA-N 0.000 description 1
- YSGKXVQMKMMRLQ-UHFFFAOYSA-N 6-(diethylamino)-2-methylidenehexanamide Chemical compound CCN(CC)CCCCC(=C)C(N)=O YSGKXVQMKMMRLQ-UHFFFAOYSA-N 0.000 description 1
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 1
- LPNVATKBHBASAJ-UHFFFAOYSA-N 6-(dimethylamino)-2-methylidenehexanamide Chemical compound CN(C)CCCCC(=C)C(N)=O LPNVATKBHBASAJ-UHFFFAOYSA-N 0.000 description 1
- XSCXUWYMDKKWSO-UHFFFAOYSA-N 6-(dipropylamino)-2-methylidenehexanamide Chemical compound CCCN(CCC)CCCCC(=C)C(N)=O XSCXUWYMDKKWSO-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- DMZPELDMAQDBBC-UHFFFAOYSA-N C(CCC)N(CCCC)CCCCC(C(=O)N)=C Chemical compound C(CCC)N(CCCC)CCCCC(C(=O)N)=C DMZPELDMAQDBBC-UHFFFAOYSA-N 0.000 description 1
- SODMSESDHVJJRB-UHFFFAOYSA-N CCCCN(CCCC)CCC(=C)C(N)=O Chemical compound CCCCN(CCCC)CCC(=C)C(N)=O SODMSESDHVJJRB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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 1
- 235000009565 drink mixer Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- OCMFIRSRLNISHF-UHFFFAOYSA-N n-[4-(dimethylamino)-2-methylbutan-2-yl]prop-2-enamide Chemical compound CN(C)CCC(C)(C)NC(=O)C=C OCMFIRSRLNISHF-UHFFFAOYSA-N 0.000 description 1
- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 description 1
- BVOJAXMUGDFZDX-UHFFFAOYSA-N n-ethylethanamine;ethyl prop-2-enoate Chemical compound CCNCC.CCOC(=O)C=C BVOJAXMUGDFZDX-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 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 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000000733 zeta-potential measurement Methods 0.000 description 1
Classifications
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Compositions Of Macromolecular Compounds (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〉
本発明はカチオン性エマルジョンに関する。更ニ詳シ＜
はビニルモノマー単位を２５〜９８重量％、一般式〔Ｉ
〕
〔式中、Ｒ＋はＨ又はＣＨ，、Ｒ２およびＲ３は同−又
は相異なり、炭素数１ないし４のアルキル基を表わし、
ｎは２ないし５の整数を表わす。〕
で示される１種または２種以上のジアルキルアミノアル
キルアクリルアミド系モノマー単位を２〜７５重量％を
含有する共重合体エマルジョンに関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to cationic emulsions. Further details<
contains 25 to 98% by weight of vinyl monomer units, and has the general formula [I
[In the formula, R+ is H or CH, R2 and R3 are the same or different and represent an alkyl group having 1 to 4 carbon atoms,
n represents an integer from 2 to 5. ] A copolymer emulsion containing 2 to 75% by weight of one or more dialkylaminoalkylacrylamide monomer units represented by the following.
〈従来の技術〉
従来、カチオン性エマルジョンの製造方法としては、カ
チオン性、界面活性剤の存在下にビニル系モノマーを重
合して得る方法が一般的であるが、重合経時における安
定性が欠如しており、多量の凝固物の発生を伴いやすい
とか、得られたエマルジョンのカチオン性が弱く、アニ
オン性、物質への吸着能が充分でないという問題点があ
った。<Prior art> Conventionally, the common method for producing cationic emulsions is to polymerize vinyl monomers in the presence of cationic surfactants, but this method lacks stability over time during polymerization. However, there have been problems in that the resulting emulsion tends to generate a large amount of coagulum, and the resulting emulsion has weak cationic properties, anionic properties, and insufficient ability to adsorb onto substances.
〈発明が解決しようとする課題〉
かかる現状に鑑み、本発明は、安定性があり、負に帯電
した物質への吸着能に優れた＋４５ｍＶ以上のゼータ電
位を有するカチオン性エマルジョンを提供することを目
的とするものである。<Problems to be Solved by the Invention> In view of the current situation, the present invention aims to provide a cationic emulsion that is stable and has a zeta potential of +45 mV or more and has excellent adsorption ability to negatively charged substances. This is the purpose.
〈課題を解決するための手段〉
本発明は、ビニルモノマー単位を２５〜９８重量％、一
般式〔Ｉ〕
〔式中、Ｒ，はＨ又はＣＨ３、Ｒ２およびＲ３は同−又
は相異なる炭素数１ないし４のアルキル基を表わし、ｎ
は２ないし５の整数を表わす。〕
で示される１種または２種以上のアミン基含有ラジカル
重合性ビニルモノマー単位を２〜７５重量％を含有し、
かつ共重合体の側鎖アミ７基が酸により４級塩とされて
いる事を特徴とするカチオン性エマルジョンに関するも
のである。<Means for Solving the Problems> The present invention comprises a vinyl monomer unit containing 25 to 98% by weight of the general formula [I] [wherein R is H or CH3, and R2 and R3 have the same or different carbon numbers. Represents 1 to 4 alkyl groups, n
represents an integer from 2 to 5. ] Containing 2 to 75% by weight of one or more amine group-containing radically polymerizable vinyl monomer units represented by
The present invention also relates to a cationic emulsion characterized in that the side chain amide 7 group of the copolymer is converted into a quaternary salt by an acid.
本発明による共重合体の原料として用いられる一般式Ｃ
Ｉ）で示されるジアルキルアミノアルキルアクリルアミ
ド系モノマーの好ましい具体例としては、例えばジメチ
ルアミノエチルアクリルアミド、ジメチルアミノプロピ
ルアクリルアミド、ジメチルアミノブチルアクリルアミ
ド、ジエチルアミノエチルアクリルアミド、ジエチルア
ミノプロピルアクリルアミド、ジエチルアミノブチルア
クリルアミド、ジ−ｎ−プロピルアミノエチルアクリル
アミド、ジ−ｎ−プロピルアミノプロピルアクリルアミ
ド、ジ−ｎ−プロピルアミノブチルアクリルアミド、ジ
−ｎ−ブチルアミノエチルアクリルアミド、ジ−ｎ−ブ
チルアミ／プロピルアクリルアミド、ジ−ｎ−ブチルア
ミノブチルアクリルアミド、Ｎ−（１，１−ジメチル−
３−ジメチルアミノプロピル）アクリルアミド、Ｎ−（
２−メチル−３−ジメチルアミノプロピル）アクリルア
ミドなど、およびこれらに対応するメタクリルアミド誘
導体があげられる。General formula C used as a raw material for the copolymer according to the present invention
Preferred specific examples of dialkylaminoalkylacrylamide monomers represented by I) include dimethylaminoethyl acrylamide, dimethylaminopropylacrylamide, dimethylaminobutylacrylamide, diethylaminoethyl acrylamide, diethylaminopropylacrylamide, diethylaminobutylacrylamide, di-n- Propylaminoethylacrylamide, di-n-propylaminopropylacrylamide, di-n-propylaminobutylacrylamide, di-n-butylaminoethylacrylamide, di-n-butylamino/propylacrylamide, di-n-butylaminobutylacrylamide, N-(1,1-dimethyl-
3-dimethylaminopropyl)acrylamide, N-(
Examples include 2-methyl-3-dimethylaminopropyl) acrylamide, and methacrylamide derivatives corresponding thereto.
特に好ましい該コモノマーとしては、ジメチルアミノプ
ロピルアクリルアミド、ジメチルアミノプロピルメタク
リルアミド、ジエチルアミンプロピルアクリルアミド、
ジエチルアミノプロピルメタクリルアミド、ジ−ｎ−プ
ロピルアミノプロピルアクリルアミド、ジ−ｎ−ブチル
アミノプロピルアクリルアミドがあげられる。Particularly preferred comonomers include dimethylaminopropylacrylamide, dimethylaminopropylmethacrylamide, diethylaminepropylacrylamide,
Examples include diethylaminopropylmethacrylamide, di-n-propylaminopropylacrylamide, and di-n-butylaminopropylacrylamide.
また、ジアルキルアミノアルキルアクリルアミド系モノ
マーとジアルキルアミノアルキル（メタ）アクリレート
系モノマーを併用してもよい。Furthermore, a dialkylaminoalkyl acrylamide monomer and a dialkylaminoalkyl (meth)acrylate monomer may be used in combination.
ジアルキルアミノアルキル（メタ）アクリレート系モノ
マーとしては、ジメチルアミノエチルアクリレート、ジ
メチルアミノプロピルアクリレート、ジメチルアミンブ
チルアクリレート、ジエチルアミンエチルアクリレート
、ジエチルアミノプロピルアクリレート、ジエチルアミ
ンブチルアクリレート、ジ−ｎ−プロピルアミノエチル
アクリレート、ジ−ｎ−プロピルアミノプロピルアクリ
レート、ジ−ｎ−プロピルアミノブチルアクリレート、
ジ−ｎ−ブチルアミノエチルアクリレート、ジ−ｎ−ブ
チルアミノプロピルアクリレート、ジ−ｎ−ブチルアミ
ノブチルアクリレート Ｎ−（１，１−ジメチル−３−
ジメチルアミンプロピル）アクリレート、Ｎ−（２−メ
チル−３−ジメチルアミノプロピル）アクリレートなど
、およびこれらに対応するメタクリレート誘導体があげ
られる。Examples of dialkylaminoalkyl (meth)acrylate monomers include dimethylaminoethyl acrylate, dimethylaminopropyl acrylate, dimethylamine butyl acrylate, diethylamine ethyl acrylate, diethylaminopropyl acrylate, diethylamine butyl acrylate, di-n-propylaminoethyl acrylate, di- n-propylaminopropyl acrylate, di-n-propylaminobutyl acrylate,
Di-n-butylaminoethyl acrylate, di-n-butylaminopropyl acrylate, di-n-butylaminobutylacrylate N-(1,1-dimethyl-3-
Examples include dimethylaminepropyl)acrylate, N-(2-methyl-3-dimethylaminopropyl)acrylate, and methacrylate derivatives corresponding to these.
本発明において使用される前記〔■〕モノマーと共重合
するビニルモノマーは特に限定されるものではないが、
共重合性等より次の様なモノマーが適している。例えば
、スチレン、ビニルトルエン、α−メチルスチレン、ブ
タジェン、イソプレン、エチレン、塩化ビニル、臭気ビ
ニノヘ塩化ビニリデンなどの如きハロゲン化ビニル、酢
酸ビニノペブロピオン酸ビニル、酪酸ビニ／ｌｚ、ピバ
リン酸ビニノペラウリル酸ビニル、バーサチック酸ビニ
ルなどの如きビニルエステル： （メタ）アクリル酸メ
チル、（メタ）アクリル酸エチノヘ（メタ）アクリル酸
ブチル、（メタ）アクリル酸２−エチルヘキシノヘ（メ
タ）アクリル酸ラウリル、（メタ）アクリル酸ステアリ
ルの如き（メタ）アクリル酸と炭素数１〜１８のアルキ
ルアルコールとエステル化合物、マレイン酸ジブチル等
のマレイン酸エステル＝ （メタ）アクリロニトリルな
どを挙げることができ、これらの内の１種又は２種以上
の混合物を使用することができる。又アミド基、水酸基
、カルボン酸基、メトキシ基等を含有する官能性ビニル
モノマー及び２個以上の重合性α、β−不飽和結合を有
するモノマーを必要に応じて共重合することが可能であ
る。例えば、エチレングリコールジ（メタ）アクリレー
ト、テトラエチレングリコールジ（メタ）アクリノート
、ブチレングリコールジ（メタ）アクリレート、ネオペ
ンチルグリコールジ（メタ）アクリレート、トリメチロ
ールプロパントリ （メタ）アクリレート、ペンタエリ
スリトールトリ （メタ）アクリレート等のポリ （メ
タ）アフリレート、ジビニルベンゼン、ジアリルアジペ
ート、ジアリルマレエート、ジアリルアジペート、アリ
ルメタアクリレート、トリアリルシアヌレート、トリア
リルシアヌレート、メチレンビスアクリルアミド等をあ
げることができる。The vinyl monomer copolymerized with the monomer [■] used in the present invention is not particularly limited, but
The following monomers are suitable in terms of copolymerizability, etc. For example, styrene, vinyltoluene, α-methylstyrene, butadiene, isoprene, ethylene, vinyl chloride, vinyl halides such as odoriferous vinylidene chloride, vinyl acetate, vinylpebropionate, vinyl/lz butyrate, vinyl pivalate, vinylidene chloride, etc. Vinyl esters such as vinyl, vinyl versatate, etc.: methyl (meth)acrylate, ethino (meth)acrylate, butyl (meth)acrylate, 2-ethylhexino (meth)acrylate, lauryl (meth)acrylate, (meth)acrylate Ester compounds of (meth)acrylic acid such as stearyl acid and alkyl alcohol having 1 to 18 carbon atoms, maleic acid esters such as dibutyl maleate = (meth)acrylonitrile, etc., and one or two of these Mixtures of more than one species can be used. Furthermore, it is possible to copolymerize a functional vinyl monomer containing an amide group, a hydroxyl group, a carboxylic acid group, a methoxy group, etc., and a monomer having two or more polymerizable α, β-unsaturated bonds, if necessary. . For example, ethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrynote, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri( Examples include poly(meth)afrylate such as meth)acrylate, divinylbenzene, diallyl adipate, diallyl maleate, diallyl adipate, allyl methacrylate, triallyl cyanurate, triallyl cyanurate, methylene bisacrylamide, and the like.
本発明による共重合体のアミノ基含有ラジカル重合性ビ
ニルモノマーの重合単位は２〜７５重量％、好ましくは
３〜６０重量％である。The amount of polymerized units of the amino group-containing radically polymerizable vinyl monomer in the copolymer according to the invention is from 2 to 75% by weight, preferably from 3 to 60% by weight.
ジアルキルアミノアルキルアクリルアミド系モノマーは
、酸によって中和し側鎖アミノ基を４級塩としてエマル
ジョン重合に供される。The dialkylaminoalkylacrylamide monomer is neutralized with an acid and subjected to emulsion polymerization with the side chain amino group converted into a quaternary salt.
用いる酸の種類は特に制限はないが、通常、ギ酸、酢酸
、醋酸、塩酸、リン酸、硝酸、硫酸等が好ましい。中和
反応に用いられる酸の使用量は共重合体を構成する（１
）成分の１０〜１５０モル％である。The type of acid used is not particularly limited, but formic acid, acetic acid, acetic acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, etc. are usually preferred. The amount of acid used in the neutralization reaction constitutes the copolymer (1
) is 10 to 150 mol% of the component.
重合において使用する重合開始剤としてはフリーラジカ
ルを発生する化合物であればいずれも使用することが可
能であり、例えば２，２″−アゾビス（２−アミジノプ
ロパン）塩酸塩、アゾビスイソブチロニトリル、ベンゾ
イルパーオキサイド、キュメンハイドロパーオキサイド
やｔ−ブチルハイドロパーオキサイドあるいはこれらと
還元剤との組み合わせが好ましく用いられる。また過硫
酸アンモニウム等のアニオン性の重合開始剤も使用可能
である。重合開始剤の使用量は特に制限はないが、製造
されるエマルジョンに出来るだけ残存するモノマーを少
量、にすることが好ましく、モノマーに対して０．０５
〜５重量％が適当である。As the polymerization initiator used in the polymerization, any compound that generates free radicals can be used, such as 2,2''-azobis(2-amidinopropane) hydrochloride, azobisisobutyronitrile. , benzoyl peroxide, cumene hydroperoxide, t-butyl hydroperoxide, or a combination of these and a reducing agent are preferably used.Anionic polymerization initiators such as ammonium persulfate can also be used. There is no particular restriction on the amount used, but it is preferable that the amount of monomer remaining in the emulsion produced is as small as possible, and 0.05% of the monomer is used.
~5% by weight is suitable.
重合を行う場合の界面活性剤としては、通常用いられて
いる、水溶性高分子、カチオンまたはノニオン性界面活
性剤が用いられるが、界面活性剤を用いないソープフリ
ー重合でも安定なカチオン性ポリマーの水分散体が得ら
れる。As surfactants for polymerization, commonly used water-soluble polymers, cationic or nonionic surfactants are used, but cationic polymers that are stable even in soap-free polymerization without using surfactants are used. An aqueous dispersion is obtained.
重合温度は特に制限はないが、適当な重合温度は３０〜
１００℃、好ましくは４０〜８０℃である。３０℃より
低い温度では、モノマーの重合率が低下する傾向にあり
好ましくない。There is no particular restriction on the polymerization temperature, but a suitable polymerization temperature is 30~
The temperature is 100°C, preferably 40-80°C. A temperature lower than 30°C is undesirable because the polymerization rate of the monomer tends to decrease.
又、モノマーの添加方法についても特に制限はなく、そ
の全量を最初に添加して重合してもよいし、分割添加、
連続添加して重合してもよい。Furthermore, there is no particular restriction on the method of adding the monomer; the entire amount may be added at the beginning for polymerization, or the monomer may be added in portions,
Polymerization may be carried out by continuous addition.
本発明におけるカチオン性エマルジョンは、重合経時の
安定性、及び機械安定性、放置安定性に優れ、かつゼー
タ電位が４５ｍＶ以上を示すので、負に帯電した物質へ
の接着性、吸着性において著しく優れている。さらに導
電性、抗菌性を有するものである。The cationic emulsion of the present invention has excellent stability over time during polymerization, mechanical stability, and storage stability, and has a zeta potential of 45 mV or more, so it has excellent adhesion and adsorption to negatively charged substances. ing. Furthermore, it has electrical conductivity and antibacterial properties.
そして、本発明で得られるカチオン性エマルジョンは、
繊維、紙加工、ガラス繊維加工、帯電防止加工、静電記
録紙コーティング、紙のビータ−添加、セメント混和等
の用途に特に有用である。The cationic emulsion obtained by the present invention is
It is particularly useful in applications such as fiber, paper processing, glass fiber processing, antistatic processing, electrostatic recording paper coating, paper beater addition, and cement mixing.
〈実施例〉
以下に実施例をもって、本発明の詳細な説明するが、こ
れらはいずれも例示的なものであって、本発明の内容を
限定するものではない。<Examples> The present invention will be described in detail with reference to Examples below, but these are merely illustrative and do not limit the content of the present invention.
尚、分析方法は次の通りである。The analysis method is as follows.
（１） 固形分 ＪＩＳ Ｋ６８３９の４．２に準拠した。(1) Solid content Compliant with JIS K6839 4.2.
アルミニウム箔の皿にエマルジョンを正確に秤り採り１
０５℃に保った乾燥型中で３時間乾燥後デシケータ−中
で放冷した。その質量を秤り、次式により固形分（ｗｔ
％）を求めた。Accurately weigh the emulsion onto an aluminum foil plate 1
After drying for 3 hours in a drying mold kept at 05°C, it was allowed to cool in a desiccator. Weigh the mass, and calculate the solid content (wt
%) was calculated.
Ｄ 固形分（ｗｔ％）＝−Ｘ１００ Ｄ：乾燥後の試料の質量（ｇ） Ｓ：エマルジョンの質量（ｇ） （２）粘度 ＪＩＳ Ｘ６８３８の４に準拠した。D Solid content (wt%) = -X100 D: Mass of sample after drying (g) S: mass of emulsion (g) (2) Viscosity Compliant with JIS X6838-4.
エマルジョンを容器に採りエマルジョン温度が２５±０
．５℃になるまで恒温槽に入れて調節し、Ｂｌ、型回転
粘度計（東京計器製造所側製）にて測定した。Pour the emulsion into a container and make the emulsion temperature 25±0.
．． The mixture was kept in a constant temperature bath until the temperature reached 5°C, and measured using a Bl type rotational viscometer (manufactured by Tokyo Keiki Seisakusho).
粘度計の回転数は６０回転／ｍｉｎとし、１分間回転後
の指示計の示す目盛を読み規定の換算乗数を乗じて粘度
を算出した。The rotational speed of the viscometer was 60 rotations/min, and the viscosity was calculated by reading the scale shown on the indicator after rotating for 1 minute and multiplying by a specified conversion multiplier.
（３）粒径（μ）
エマルジョンに水を加えて濃度０．０１％に調製した後
、ＵＶ分光光度計（日立■製）にて、濁度法により粒子
径を求めた。(3) Particle size (μ) After adding water to the emulsion to adjust the concentration to 0.01%, the particle size was determined by the turbidity method using a UV spectrophotometer (manufactured by Hitachi ■).
（４）ゼータ電位
エマルジョンに水を加えて濃度０．０１％に調製した後
、コロイド粒子ゼータ電位測定装置！Ｊｏｄｅ１５ＱＩ
Ｌａｚｅｒ Ｚｅｅ Ｍｅｔｅｒ （米国ＰＥＮ Ｋ
ＥＮ Ｑ＠製）にてゼータ電位を求めた。(4) Zeta potential After adding water to the emulsion and adjusting the concentration to 0.01%, a colloidal particle zeta potential measurement device! Jode15QI
Lazer Zee Meter (USA PEN K
Zeta potential was determined using EN Q@).
（５）安定性
エマルジョン２５０ｇをハミルトンビーチドリンクミキ
サー（米国）１ａｍｉｌｔｏｎ Ｂｅａｃｈ（ｍ製）に
て、１５、０００ｒｐｍで３０分攪拌し、攪拌後の粘度
及び濾過残渣を求めた。(5) Stability 250 g of the emulsion was stirred at 15,000 rpm for 30 minutes using a Hamilton Beach Drink Mixer (USA), manufactured by M, and the viscosity after stirring and the filtration residue were determined.
攪拌により、著しい増粘が認められず、濾過残渣が０．
１％以下のものを安定性が良好であるとした。As a result of stirring, no significant increase in viscosity was observed, and the filtration residue was 0.
Stability was considered to be good if it was 1% or less.
尚、濾過残渣は、エマルジョンを１００メツシユステン
レス銅を通過させて生じる濾過残渣の乾燥重量を秤量し
、エマルジョン重量に対する濾過残渣重量の比率を求め
た。As for the filtration residue, the dry weight of the filtration residue produced by passing the emulsion through 100 mesh stainless copper was weighed, and the ratio of the weight of the filtration residue to the weight of the emulsion was determined.
実施例−１
還流冷却器、温度計、撹拌機を備えた２１のセパラブル
フラスコに水６００ｇ、ジメチルアミンプロピルアクリ
ルアミド８０ｇと３６％塩酸５２ｇ （共重合体のアミ
ン基に対し、モル比で１．０に相当する塩酸）、スチレ
ン１６０ｇ、アクリル酸ブチル１６０ｇを攪拌下に仕込
み、６０℃に昇温した後、反応系内を窒素ガスで置換し
た。Example-1 In 21 separable flasks equipped with a reflux condenser, a thermometer, and a stirrer, 600 g of water, 80 g of dimethylamine propylacrylamide, and 52 g of 36% hydrochloric acid (mole ratio of 1.0 g to the amine group of the copolymer) were added. 0 hydrochloric acid), 160 g of styrene, and 160 g of butyl acrylate were charged with stirring, and after raising the temperature to 60° C., the inside of the reaction system was purged with nitrogen gas.
次に５％２．２′−アゾビス（２−アミジノプロパン）
塩酸塩水溶液を４時間一定速度で反応系内に供給して反
応させた。４時間後さらに８０℃昇温し、２時間反応さ
せ残留モノマーが０．５％以下に減少したところで重合
を終了した。Then 5% 2.2'-azobis(2-amidinopropane)
The aqueous hydrochloride solution was fed into the reaction system at a constant rate for 4 hours to react. After 4 hours, the temperature was further raised to 80°C, and the reaction was continued for 2 hours, and the polymerization was terminated when the residual monomer decreased to 0.5% or less.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
実施例−２
実施例−１と同様に操作し、ただし実施例−１のスチレ
ン１６０ｇ、アクリル酸ブチル１６０ｇの代わりにスチ
レン３２０ｇを用いて重合した。Example 2 Polymerization was carried out in the same manner as in Example 1, except that 320 g of styrene was used instead of 160 g of styrene and 160 g of butyl acrylate in Example 1.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
実施例−３
実施例−２と同様に操作し、ただし実施例−２のジメチ
ルアミノプロピルアクリルアミド８０ｇ１スチレン３２
０ｇの代わりにジメチルアミンプロピルアクリルアミド
１２０ｇ、スチレン８０ｇを用いて重合した。Example-3 Operate in the same manner as in Example-2, except that 80 g of dimethylaminopropylacrylamide of Example-2 and 32 g of styrene were used.
Polymerization was carried out using 120 g of dimethylamine propylacrylamide and 80 g of styrene instead of 0 g.
実施例−４
実施例−１と同様に操作し、ただし実施例−１のスチレ
ン１６０ｇの代わりにメタクリル酸メチル１６０ｇを用
いて重合した。Example 4 Polymerization was carried out in the same manner as in Example 1, except that 160 g of methyl methacrylate was used in place of 160 g of styrene in Example 1.
実施例−５
実施例−１と同様に操作し、ただし実施例−１のジメチ
ルアミノプロピルアクリルアミド８０ｇの代わりにジエ
チルアミノプロピルアクリルアミド８０ｇを用いて重合
した。Example 5 Polymerization was carried out in the same manner as in Example 1, except that 80 g of diethylaminopropylacrylamide was used in place of 80 g of dimethylaminopropylacrylamide in Example 1.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
実施例−６
実施例−１と同様に操作し、ただし実施例−１のジメチ
ルアミノプロピルアクリルアミド８０ｇの代わりジブチ
ルアミノプロピルアクリルアミド８θｇを用い、さらに
カチオン性界面活性剤、２７％コータミン２４Ｐ（花王
■製）３０ｇを添加して重合した。Example-6 The same procedure as in Example-1 was carried out, except that 80 g of dibutylaminopropylacrylamide was used instead of 80 g of dimethylaminopropylacrylamide in Example-1, and a cationic surfactant, 27% Cortamine 24P (manufactured by Kao ■) was used. ) was added and polymerized.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
実施例−７
実施例−１と同様に操作し、ただし実施例−１のジメチ
ルアミノプロピルアクリルアミド８０ｇ１スチレン１６
０ｇ、アクリル酸ブチル１６０ｇの代わりに、ジメチル
アミノプロピルアクリルアミド３０ｇ１スチレン２８５
ｇ、アクリル酸ブチル２８５ｇを用い、さらにカチオン
性界面活性剤、２７％コータミン２４Ｐ（花王■製）４
４ｇを添加して重合した。Example-7 Operate in the same manner as in Example-1, except that 80 g of dimethylaminopropylacrylamide of Example-1 1 16 styrene
0 g, butyl acrylate 160 g, dimethylaminopropylacrylamide 30 g 1 styrene 285
g, 285 g of butyl acrylate, and a cationic surfactant, 27% Cortamine 24P (manufactured by Kao ■) 4
4g was added and polymerized.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
実施例−８
実施例−１と同様に操作し、ただし３６％塩酸５２ｇの
代わりにリン酸５０ｇ（共重合体のアミン基に対し、モ
ル比で１．０に相当する塩酸）を用いて重合した。Example-8 Polymerization was carried out in the same manner as in Example-1, except that 50 g of phosphoric acid (hydrochloric acid corresponding to a molar ratio of 1.0 to the amine group of the copolymer) was used instead of 52 g of 36% hydrochloric acid. did.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
比較例−１
実施例−６と同様に操作し、ただしジメチルアミノプロ
ピルアクリルアミド３０ｇと３６％塩酸２０ｇを用いず
に重合した。Comparative Example 1 Polymerization was carried out in the same manner as in Example 6, except that 30 g of dimethylaminopropylacrylamide and 20 g of 36% hydrochloric acid were not used.
評価結果は第１表の通りである。The evaluation results are shown in Table 1.
〈発明の効果〉
本発明によるカチオン性エマルジョンは安定性に優れ、
高いカチオン性を有しており、繊維・紙加工、ガラス繊
維加工、帯電防止加工、静電記録紙コーティング、紙の
ビータ−添加、セメント混和等の用途に用いることがで
きる。<Effects of the invention> The cationic emulsion according to the invention has excellent stability,
It has high cationic properties and can be used for applications such as fiber/paper processing, glass fiber processing, antistatic processing, electrostatic recording paper coating, paper beater addition, and cement mixing.
＼ ＼ ＼ ＼ ＼ ＼ ＼ ＼ ＼ ＼\ \ \ \ \ \ \ \ \ \
Claims (3)
〔 I 〕 ▲数式、化学式、表等があります▼〔 I 〕 〔式中、Ｒ＿１はＨ又はＣＨ＿３、Ｒ＿２およびＲ＿３
は同一又は相異なる炭素数１ないし４のアルキル基を表
わし、ｎは２ないし５の整数を表わす。〕 で示される１種又は２種以上のジアルキルアミノアルキ
ルアクリルアミド系モノマー単位を２〜７５重量％を含
有し、かつ共重合体の側鎖アミノ基が酸により４級塩と
されている事を特徴とするカチオン性エマルジョン。(1) 25 to 98% by weight of vinyl monomer units, general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] [In the formula, R_1 is H or CH_3, R_2 and R_3
represent the same or different alkyl groups having 1 to 4 carbon atoms, and n represents an integer of 2 to 5. ] The copolymer is characterized by containing 2 to 75% by weight of one or more dialkylaminoalkylacrylamide monomer units represented by the formula, and in which the side chain amino group of the copolymer is made into a quaternary salt with an acid. Cationic emulsion.
ル酸エステル類から成る群より選ばれる１種又は２種以
上である請求項１記載のカチオン性エマルジョン。(2) The cationic emulsion according to claim 1, wherein the vinyl monomer is one or more selected from the group consisting of styrene or (meth)acrylic acid esters.
のカチオン性エマルジョン。(3) The cationic emulsion according to claim 1, which has a zeta potential of 45 mV or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1092244A JPH02269715A (en) | 1989-04-11 | 1989-04-11 | Cationic emulsion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1092244A JPH02269715A (en) | 1989-04-11 | 1989-04-11 | Cationic emulsion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02269715A true JPH02269715A (en) | 1990-11-05 |
Family
ID=14049018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1092244A Pending JPH02269715A (en) | 1989-04-11 | 1989-04-11 | Cationic emulsion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02269715A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002322218A (en) * | 2001-04-25 | 2002-11-08 | Chuo Rika Kogyo Corp | Acrylic resin emulsion and method of producing the same |
| JP2008120880A (en) * | 2006-11-09 | 2008-05-29 | Kao Corp | Method for producing polymer |
| WO2014156709A1 (en) * | 2013-03-28 | 2014-10-02 | 松本油脂製薬株式会社 | Antistatic treatment agent for fibers and method for producing antistatically treated fibers |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5924708A (en) * | 1982-08-02 | 1984-02-08 | Kohjin Co Ltd | Production of cationic acrylamide polymer |
| JPS5927903A (en) * | 1982-08-10 | 1984-02-14 | Mitsui Saianamitsudo Kk | Water-soluble polymer, its production and its use |
| JPS59193911A (en) * | 1983-04-18 | 1984-11-02 | Kohjin Co Ltd | Polymeric substance having high absorptivity |
| JPS61241308A (en) * | 1985-04-17 | 1986-10-27 | Chuo Rika Kogyo Kk | Production of cationic emulsion |
| JPS63251409A (en) * | 1987-04-09 | 1988-10-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | Cationic oligomer |
| JPS63267408A (en) * | 1987-04-27 | 1988-11-04 | Dai Ichi Kogyo Seiyaku Co Ltd | Cationic high polymer flocculating agent |
-
1989
- 1989-04-11 JP JP1092244A patent/JPH02269715A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5924708A (en) * | 1982-08-02 | 1984-02-08 | Kohjin Co Ltd | Production of cationic acrylamide polymer |
| JPS5927903A (en) * | 1982-08-10 | 1984-02-14 | Mitsui Saianamitsudo Kk | Water-soluble polymer, its production and its use |
| JPS59193911A (en) * | 1983-04-18 | 1984-11-02 | Kohjin Co Ltd | Polymeric substance having high absorptivity |
| JPS61241308A (en) * | 1985-04-17 | 1986-10-27 | Chuo Rika Kogyo Kk | Production of cationic emulsion |
| JPS63251409A (en) * | 1987-04-09 | 1988-10-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | Cationic oligomer |
| JPS63267408A (en) * | 1987-04-27 | 1988-11-04 | Dai Ichi Kogyo Seiyaku Co Ltd | Cationic high polymer flocculating agent |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002322218A (en) * | 2001-04-25 | 2002-11-08 | Chuo Rika Kogyo Corp | Acrylic resin emulsion and method of producing the same |
| JP2008120880A (en) * | 2006-11-09 | 2008-05-29 | Kao Corp | Method for producing polymer |
| WO2014156709A1 (en) * | 2013-03-28 | 2014-10-02 | 松本油脂製薬株式会社 | Antistatic treatment agent for fibers and method for producing antistatically treated fibers |
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