JP5424631B2 - Cationic gemini surfactant - Google Patents
Cationic gemini surfactant Download PDFInfo
- Publication number
- JP5424631B2 JP5424631B2 JP2008322336A JP2008322336A JP5424631B2 JP 5424631 B2 JP5424631 B2 JP 5424631B2 JP 2008322336 A JP2008322336 A JP 2008322336A JP 2008322336 A JP2008322336 A JP 2008322336A JP 5424631 B2 JP5424631 B2 JP 5424631B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- diethylamino
- dimethylamino
- dimethyl
- 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.)
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- 239000004094 surface-active agent Substances 0.000 title claims description 29
- 125000002091 cationic group Chemical group 0.000 title claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- -1 tertiary amine compound Chemical class 0.000 description 121
- 150000001875 compounds Chemical class 0.000 description 31
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 150000004075 acetic anhydrides Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OXOWTLDONRGYOT-UHFFFAOYSA-M 4-(dimethylamino)butanoate Chemical compound CN(C)CCCC([O-])=O OXOWTLDONRGYOT-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- IOUUIFSIQMVYKP-UHFFFAOYSA-N Tetradecyl acetate Chemical compound CCCCCCCCCCCCCCOC(C)=O IOUUIFSIQMVYKP-UHFFFAOYSA-N 0.000 description 3
- RSSGSPAYFRXVKG-UHFFFAOYSA-N Tridecanamide Chemical compound CCCCCCCCCCCCC(N)=O RSSGSPAYFRXVKG-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- ZNAITCOKZPFZSA-UHFFFAOYSA-N decanamide Chemical compound CCCCCCCCCC(N)=O.CCCCCCCCCC(N)=O ZNAITCOKZPFZSA-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- REEPJBYQLCWOAR-UHFFFAOYSA-N heptadecanamide Chemical compound CCCCCCCCCCCCCCCCC(N)=O REEPJBYQLCWOAR-UHFFFAOYSA-N 0.000 description 3
- AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- GHLZUHZBBNDWHW-UHFFFAOYSA-N nonanamide Chemical compound CCCCCCCCC(N)=O GHLZUHZBBNDWHW-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 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 3
- 125000002958 pentadecyl 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])[H] 0.000 description 3
- 238000003408 phase transfer catalysis Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000012756 surface treatment agent Substances 0.000 description 3
- 125000002889 tridecyl 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])[H] 0.000 description 3
- FKVMWDZRDMCIAJ-UHFFFAOYSA-N undecanamide Chemical compound CCCCCCCCCCC(N)=O FKVMWDZRDMCIAJ-UHFFFAOYSA-N 0.000 description 3
- JMLUDYXDXUBOTH-UHFFFAOYSA-N 2-(dimethylamino)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCN(C)C JMLUDYXDXUBOTH-UHFFFAOYSA-N 0.000 description 2
- XSKSOLBYWOVVBN-UHFFFAOYSA-N 2-(dimethylamino)ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCN(C)C XSKSOLBYWOVVBN-UHFFFAOYSA-N 0.000 description 2
- UVIKOFDLWXHASA-UHFFFAOYSA-N 2-(dimethylamino)ethyl hexanoate Chemical compound CCCCCC(=O)OCCN(C)C UVIKOFDLWXHASA-UHFFFAOYSA-N 0.000 description 2
- SXIOLYXSOHUULZ-UHFFFAOYSA-N 2-(dimethylamino)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCN(C)C SXIOLYXSOHUULZ-UHFFFAOYSA-N 0.000 description 2
- PPRUSMUBWUQYRY-UHFFFAOYSA-N 2-chloroethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCl PPRUSMUBWUQYRY-UHFFFAOYSA-N 0.000 description 2
- DSNJGFLHEVDMHH-UHFFFAOYSA-N 2-dodecoxy-n,n-dimethylethanamine Chemical compound CCCCCCCCCCCCOCCN(C)C DSNJGFLHEVDMHH-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HPEOXVZDHZBRTC-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)NC(C(CC)N(CC)CC)=O Chemical compound C(CCCCCCCCCCCCCCC)NC(C(CC)N(CC)CC)=O HPEOXVZDHZBRTC-UHFFFAOYSA-N 0.000 description 2
- CJHMAONETFJYQU-UHFFFAOYSA-N CCCCCCCCCCCCNC(=O)C(C)N(C)C Chemical compound CCCCCCCCCCCCNC(=O)C(C)N(C)C CJHMAONETFJYQU-UHFFFAOYSA-N 0.000 description 2
- 239000005698 Dodecyl acetate Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- ZCZSIDMEHXZRLG-UHFFFAOYSA-N acetic acid heptyl ester Natural products CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 description 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N acetic acid n-dodecyl ester Natural products CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- GTNYVDGWECRBPG-UHFFFAOYSA-N dodecyl 3-(dimethylamino)propanoate Chemical compound CCCCCCCCCCCCOC(=O)CCN(C)C GTNYVDGWECRBPG-UHFFFAOYSA-N 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000002960 margaryl 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])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001421 myristyl 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])[H] 0.000 description 2
- RHHMQEKCJODHKZ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]undecanamide Chemical compound CCCCCCCCCCC(=O)NCCN(C)C RHHMQEKCJODHKZ-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- UBAOFCNBCAZEBL-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O.CCCCCCCC(N)=O UBAOFCNBCAZEBL-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- RQGCQWARLQDMCZ-UHFFFAOYSA-N pentadecanamide Chemical compound CCCCCCCCCCCCCCC(N)=O RQGCQWARLQDMCZ-UHFFFAOYSA-N 0.000 description 2
- HLEKYJVHEBHTMR-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O.CCCCC(N)=O HLEKYJVHEBHTMR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl 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])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- IJBSIWUUKRQZHJ-UHFFFAOYSA-N (dimethylamino)methyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCN(C)C IJBSIWUUKRQZHJ-UHFFFAOYSA-N 0.000 description 1
- LYBUJRHWCDOAOB-UHFFFAOYSA-N (dimethylamino)methyl hexanoate Chemical compound CCCCCC(=O)OCN(C)C LYBUJRHWCDOAOB-UHFFFAOYSA-N 0.000 description 1
- HUTGAOVNQCOKPI-UHFFFAOYSA-N (dimethylamino)methyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCN(C)C HUTGAOVNQCOKPI-UHFFFAOYSA-N 0.000 description 1
- HPUIQFXZXVKZBN-UHFFFAOYSA-N 1-butoxy-n,n-dimethylmethanamine Chemical compound CCCCOCN(C)C HPUIQFXZXVKZBN-UHFFFAOYSA-N 0.000 description 1
- IPRYDBGNTZFWNM-UHFFFAOYSA-N 2-(diethylamino)-N-heptylacetamide Chemical compound CCCCCCCNC(=O)CN(CC)CC IPRYDBGNTZFWNM-UHFFFAOYSA-N 0.000 description 1
- ICUZRKWAIRREGO-UHFFFAOYSA-N 2-(diethylamino)-N-pentylacetamide Chemical compound CCCCCNC(=O)CN(CC)CC ICUZRKWAIRREGO-UHFFFAOYSA-N 0.000 description 1
- ACTPGMUZGGCATJ-UHFFFAOYSA-N 2-(diethylamino)-n-dodecylacetamide Chemical compound CCCCCCCCCCCCNC(=O)CN(CC)CC ACTPGMUZGGCATJ-UHFFFAOYSA-N 0.000 description 1
- NVYGSHSLKVPSHW-UHFFFAOYSA-N 2-(diethylamino)-n-hexadecylacetamide Chemical compound CCCCCCCCCCCCCCCCNC(=O)CN(CC)CC NVYGSHSLKVPSHW-UHFFFAOYSA-N 0.000 description 1
- ZBCSMJSQXZLOKE-UHFFFAOYSA-N 2-(diethylamino)-n-tetradecylacetamide Chemical compound CCCCCCCCCCCCCCNC(=O)CN(CC)CC ZBCSMJSQXZLOKE-UHFFFAOYSA-N 0.000 description 1
- HTFJQCPNSUFMLF-UHFFFAOYSA-N 2-(diethylamino)ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCCN(CC)CC HTFJQCPNSUFMLF-UHFFFAOYSA-N 0.000 description 1
- UNWMSJSGBWRHNY-UHFFFAOYSA-N 2-(diethylamino)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCN(CC)CC UNWMSJSGBWRHNY-UHFFFAOYSA-N 0.000 description 1
- JATDCWGWIMIJBI-UHFFFAOYSA-N 2-(diethylamino)ethyl heptanoate Chemical compound CCCCCCC(=O)OCCN(CC)CC JATDCWGWIMIJBI-UHFFFAOYSA-N 0.000 description 1
- QZWCVMDOSCAEGE-UHFFFAOYSA-N 2-(diethylamino)ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCN(CC)CC QZWCVMDOSCAEGE-UHFFFAOYSA-N 0.000 description 1
- AEIJVYPRKAWFPN-UHFFFAOYSA-N 2-(diethylamino)ethyl hexanoate Chemical compound CCCCCC(=O)OCCN(CC)CC AEIJVYPRKAWFPN-UHFFFAOYSA-N 0.000 description 1
- SIGUPTYSXOYPCR-UHFFFAOYSA-N 2-(diethylamino)ethyl nonanoate Chemical compound CCCCCCCCC(=O)OCCN(CC)CC SIGUPTYSXOYPCR-UHFFFAOYSA-N 0.000 description 1
- QZJDYFVPLXBWTK-UHFFFAOYSA-N 2-(diethylamino)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCN(CC)CC QZJDYFVPLXBWTK-UHFFFAOYSA-N 0.000 description 1
- NIWZVGDDVLDDTA-UHFFFAOYSA-N 2-(diethylamino)ethyl octanoate Chemical compound CCCCCCCC(=O)OCCN(CC)CC NIWZVGDDVLDDTA-UHFFFAOYSA-N 0.000 description 1
- BQPODRBUZYXAQG-UHFFFAOYSA-N 2-(diethylamino)ethyl pentanoate Chemical compound CCCCC(=O)OCCN(CC)CC BQPODRBUZYXAQG-UHFFFAOYSA-N 0.000 description 1
- OBCVQBDNYJJTOU-UHFFFAOYSA-N 2-(diethylamino)ethyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCN(CC)CC OBCVQBDNYJJTOU-UHFFFAOYSA-N 0.000 description 1
- LLUXBFKIKKWXGG-UHFFFAOYSA-N 2-(diethylamino)ethyl undecanoate Chemical compound CCCCCCCCCCC(=O)OCCN(CC)CC LLUXBFKIKKWXGG-UHFFFAOYSA-N 0.000 description 1
- CSXXZKCDEBZKHH-UHFFFAOYSA-N 2-(dimethylamino)-N-dodecylbutanamide Chemical compound CCCCCCCCCCCCNC(=O)C(CC)N(C)C CSXXZKCDEBZKHH-UHFFFAOYSA-N 0.000 description 1
- LBFNINKSTWGFFC-UHFFFAOYSA-N 2-(dimethylamino)-N-octylacetamide Chemical compound CCCCCCCCNC(=O)CN(C)C LBFNINKSTWGFFC-UHFFFAOYSA-N 0.000 description 1
- FJJJJDTVUJYUAP-UHFFFAOYSA-N 2-(dimethylamino)-n-dodecylacetamide Chemical compound CCCCCCCCCCCCNC(=O)CN(C)C FJJJJDTVUJYUAP-UHFFFAOYSA-N 0.000 description 1
- FXOWCKKUKRPJAU-UHFFFAOYSA-N 2-(dimethylamino)-n-hexadecylacetamide Chemical compound CCCCCCCCCCCCCCCCNC(=O)CN(C)C FXOWCKKUKRPJAU-UHFFFAOYSA-N 0.000 description 1
- LXFIHGQBZFXNGG-UHFFFAOYSA-N 2-(dimethylamino)-n-hexylacetamide Chemical compound CCCCCCNC(=O)CN(C)C LXFIHGQBZFXNGG-UHFFFAOYSA-N 0.000 description 1
- NCISPHDFTJMZTI-UHFFFAOYSA-N 2-(dimethylamino)-n-hexylpropanamide Chemical compound CCCCCCNC(=O)C(C)N(C)C NCISPHDFTJMZTI-UHFFFAOYSA-N 0.000 description 1
- WJDBGWAIWRQAQM-UHFFFAOYSA-N 2-(dimethylamino)ethyl heptadecanoate Chemical compound CCCCCCCCCCCCCCCCC(=O)OCCN(C)C WJDBGWAIWRQAQM-UHFFFAOYSA-N 0.000 description 1
- SDHJNSJCOUWATD-UHFFFAOYSA-N 2-(dimethylamino)ethyl heptanoate Chemical compound CCCCCCC(=O)OCCN(C)C SDHJNSJCOUWATD-UHFFFAOYSA-N 0.000 description 1
- RBLJYVBVMVTWKL-UHFFFAOYSA-N 2-(dimethylamino)ethyl octanoate Chemical compound CCCCCCCC(=O)OCCN(C)C RBLJYVBVMVTWKL-UHFFFAOYSA-N 0.000 description 1
- YDAFEAGUDJFURU-UHFFFAOYSA-N 2-(dimethylamino)ethyl pentadecanoate Chemical compound CCCCCCCCCCCCCCC(=O)OCCN(C)C YDAFEAGUDJFURU-UHFFFAOYSA-N 0.000 description 1
- DPIKKTSTDVVXGM-UHFFFAOYSA-N 2-(dimethylamino)ethyl pentanoate Chemical compound CCCCC(=O)OCCN(C)C DPIKKTSTDVVXGM-UHFFFAOYSA-N 0.000 description 1
- WVTLMDGNANZSAT-UHFFFAOYSA-N 2-(dimethylamino)ethyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCN(C)C WVTLMDGNANZSAT-UHFFFAOYSA-N 0.000 description 1
- RGGHUXZJAONCIQ-UHFFFAOYSA-N 2-(dimethylamino)ethyl undecanoate Chemical compound CCCCCCCCCCC(=O)OCCN(C)C RGGHUXZJAONCIQ-UHFFFAOYSA-N 0.000 description 1
- GGZYGFBQOCOKAE-UHFFFAOYSA-N 2-butoxy-n,n-diethylethanamine Chemical compound CCCCOCCN(CC)CC GGZYGFBQOCOKAE-UHFFFAOYSA-N 0.000 description 1
- APUATYFVVUNQRY-UHFFFAOYSA-N 2-butoxy-n,n-dimethylethanamine Chemical compound CCCCOCCN(C)C APUATYFVVUNQRY-UHFFFAOYSA-N 0.000 description 1
- ZMJBAJXDOXQVME-UHFFFAOYSA-N 2-decoxy-n,n-dimethylethanamine Chemical compound CCCCCCCCCCOCCN(C)C ZMJBAJXDOXQVME-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- CEUPSWZDQFEYHG-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tridecanamide Chemical compound CCCCCCCCCCCCC(=O)NCCCN(C)C CEUPSWZDQFEYHG-UHFFFAOYSA-N 0.000 description 1
- XACXUAPFQNFHPD-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]undecanamide Chemical compound CCCCCCCCCCC(=O)NCCCN(C)C XACXUAPFQNFHPD-UHFFFAOYSA-N 0.000 description 1
- UDAGAWLBLDHGJV-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]decanamide Chemical compound CCCCCCCCCC(=O)NCCCCN(C)C UDAGAWLBLDHGJV-UHFFFAOYSA-N 0.000 description 1
- YLYBTZIQSIBWLI-UHFFFAOYSA-N n-octyl acetate Natural products CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- FDJSESZWPWMLEC-UHFFFAOYSA-N nonane Chemical compound CCCCCCCC[CH2+] FDJSESZWPWMLEC-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- FHSJASSJVNBPOX-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCCCC(N)=O FHSJASSJVNBPOX-UHFFFAOYSA-N 0.000 description 1
- YLDIXDYDANWKBW-UHFFFAOYSA-N octyl 2-(dimethylamino)acetate Chemical compound CCCCCCCCOC(=O)CN(C)C YLDIXDYDANWKBW-UHFFFAOYSA-N 0.000 description 1
- OUYCCOBIJYUMAK-UHFFFAOYSA-N octyl pentanoate Chemical compound CCCCCCCCOC(=O)CCCC OUYCCOBIJYUMAK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000015227 regulation of liquid surface tension Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ARZGWBJFLJBOTR-UHFFFAOYSA-N tetradecanamide Chemical compound CCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCC(N)=O ARZGWBJFLJBOTR-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- DCPOFLVKFCDPKI-UHFFFAOYSA-N undecyl 3-(dimethylamino)propanoate Chemical compound CCCCCCCCCCCOC(=O)CCN(C)C DCPOFLVKFCDPKI-UHFFFAOYSA-N 0.000 description 1
- DPMDQRRFSVRUMR-UHFFFAOYSA-N undecyl butanoate Chemical compound CCCCCCCCCCCOC(=O)CCC DPMDQRRFSVRUMR-UHFFFAOYSA-N 0.000 description 1
Description
本発明は、カチオン性ジェミニ型界面活性剤に関し、詳細には、2分子の第三級アミン化合物が、酸無水物の連結基で結合された構造を有するカチオン性ジェミニ型界面活性剤に関する。 The present invention relates to a cationic gemini-type surfactant, and in particular, to a cationic gemini-type surfactant having a structure in which two molecules of a tertiary amine compound are bound by an acid anhydride linking group.
アルキルトリメチルアンモニウム塩のような1鎖1親水基型の第4級アンモニウム化合物であるカチオン性界面活性剤は、洗剤、柔軟剤、乳化剤、分散剤、帯電防止剤、表面処理剤、抗菌剤、殺生物剤、染料、インクジェット記録用紙、スキンケアローション組成物、ヘアコンディショニング組成物、化粧品組成物、相関移動触媒反応などに用いられている。近年、1鎖1親水基含有界面活性剤を連結基で連結した構造を有するジェミニ型界面活性剤と呼ばれるカチオン性化合物が、優れた界面活性能のために低濃度の配合で済み、環境への負荷が低減化され、生分解性に優れることから、さまざまな用途や研究開発が進められている(非特許文献1、特許文献1)。 Cationic surfactants that are quaternary ammonium compounds of one chain and one hydrophilic group type such as alkyltrimethylammonium salts are detergents, softeners, emulsifiers, dispersants, antistatic agents, surface treatment agents, antibacterial agents, killing agents. It is used in biological agents, dyes, ink jet recording paper, skin care lotion compositions, hair conditioning compositions, cosmetic compositions, phase transfer catalysis and the like. In recent years, a cationic compound called a Gemini-type surfactant having a structure in which a one-chain, one hydrophilic group-containing surfactant is linked by a linking group has been formulated with a low concentration due to its excellent surface-active ability. Since the load is reduced and the biodegradability is excellent, various uses and research and development have been promoted (Non-patent Document 1, Patent Document 1).
しかしながら従来のカチオン性ジェミニ型界面活性剤は、その構造や鎖長に起因して、生分解性あるいは界面活性能が十分であるとは言い難かった。本発明者等は、かかる課題を解決すべく鋭意研究した結果、2分子の第三級アミン化合物を、酸無水物の連結基で結合した構造のカチオン性ジェミニ型界面活性剤が、生分解性、界面活性能に優れ、さまざまな用途に有用であることを見出し、本発明を完成するに至った。 However, it has been difficult to say that conventional cationic gemini surfactants have sufficient biodegradability or surface activity due to their structure and chain length. As a result of intensive studies to solve such problems, the present inventors have found that a cationic gemini-type surfactant having a structure in which two molecules of a tertiary amine compound are bonded with an acid anhydride linking group is biodegradable. The present inventors have found that it has excellent surface activity and is useful for various applications, and has completed the present invention.
即ち本発明は、下記一般式(1)で示されるカチオン性ジェミニ型界面活性剤である。 That is, the present invention is a cationic gemini-type surfactant represented by the following general formula (1).
但し、一般式(1)中の、Xはハロゲン原子を示し、m及びm’は1〜4の整数、R1及びR1’は炭素数3〜17のアルキル基、R2及びR2’はメチル基もしくはエチル基、A及びA’はエステル結合(COOあるいはOOC)、アミド結合(CONHあるいはNHCO)、エーテル結合(O)の群から選ばれた結合基を示し、mとm’、R1とR1’、R2とR2’、AとA’はそれぞれ同一である対称型構造であっても、異なる非対称型構造であってもよい。 However, in general formula (1), X represents a halogen atom, m and m ′ are integers of 1 to 4, R 1 and R 1 ′ are alkyl groups of 3 to 17 carbon atoms, R 2 and R 2 ′. Is a methyl group or an ethyl group, and A and A ′ are linking groups selected from the group consisting of an ester bond (COO or OOC), an amide bond (CONH or NHCO), and an ether bond (O), and m and m ′, R 1 and R 1 ′, R 2 and R 2 ′, and A and A ′ may be the same symmetric structure or different asymmetric structures.
本発明のカチオン性ジェミニ型界面活性剤は、優れた界面活性能のために低濃度の配合で済み、環境への負荷が低減化される。また低刺激性で、生分解性に優れる分子構造であり、洗剤、柔軟剤、乳化剤、分散剤、帯電防止剤、表面処理剤、抗菌剤、殺生物剤、染料、インクジェット記録用紙、スキンケアローション組成物、ヘアコンディショニング組成物、化粧品組成物、相関移動触媒反応などのさまざまな用途に有用である。 The cationic gemini surfactant of the present invention can be formulated at a low concentration because of its excellent surface activity, and the burden on the environment is reduced. In addition, it has a low irritation and excellent biodegradable molecular structure. Detergent, softener, emulsifier, dispersant, antistatic agent, surface treatment agent, antibacterial agent, biocide, dye, ink jet recording paper, skin care lotion composition It is useful for various applications such as products, hair conditioning compositions, cosmetic compositions, phase transfer catalysis.
本発明の一般式(1)で表されるカチオン性ジェミニ型界面活性剤は、一般式(2)で示される2分子の第三級アミン化合物と無水ハロゲン化酢酸とを4級化反応させて得ることができ、一般式(2)で示される2分子の第三級アミン化合物が、それぞれ同一である対称型構造でもあっても、異なる非対称型構造であってもよい。一般式(1)中、X−はフッ素イオン、塩素イオン、臭素イオン、ヨウ素イオン等のハロゲンイオンを示す。またm及びm’は一般式(2)で示される第三級アミン化合物に由来する1〜4の整数、R1及びR1’は炭素数3〜17のアルキル基であり、特に炭素数7〜12のアルキル基が界面活性能に優れるため好ましい。また、R2はメチル基もしくはエチル基、AはCOOあるいはOOCのエステル結合、CONHあるいはNHCOのアミド結合、Oのエーテル結合の群から選ばれた結合基であり、特にエステル結合が生分解性に優れるため好ましい。 The cationic gemini-type surfactant represented by the general formula (1) of the present invention is obtained by subjecting two molecules of a tertiary amine compound represented by the general formula (2) to quaternized reaction with halogenated acetic anhydride. The two molecules of the tertiary amine compound represented by the general formula (2) may have the same symmetric structure or different asymmetric structures. In the general formula (1), X − represents a halogen ion such as a fluorine ion, a chlorine ion, a bromine ion, or an iodine ion. M and m ′ are integers of 1 to 4 derived from the tertiary amine compound represented by the general formula (2), and R 1 and R 1 ′ are alkyl groups having 3 to 17 carbon atoms, particularly those having 7 carbon atoms. ˜12 alkyl groups are preferred because of their excellent surface activity. R 2 is a methyl group or an ethyl group, A is a linking group selected from the group consisting of a COO or OOC ester bond, a CONH or NHCO amide bond, and an O ether bond, and the ester bond is particularly biodegradable. It is preferable because it is excellent.
一般式(2)で表される第三級アミン化合物としては、COOのエステル結合基を有するアルカン酸−ジメチル(もしくはジエチル)アミノアルキルエステル、OOCのエステル結合基を有するジメチル(もしくはジエチル)アミノアルカン酸アルキル、CONHのアミド結合基を有するN−[(ジメチルアミノ)(もしくは(ジエチルアミノ))アルキル]アルカンアミド、NHCOのアミド結合基を有するジメチル(もしくはジエチル)アミノアルカン酸アルキルアミド、Oのエーテル結合基を有するN,N−ジメチル(もしくはジエチル)アルキルオキシアルカンアミンが挙げられる。 The tertiary amine compound represented by the general formula (2) includes alkanoic acid-dimethyl (or diethyl) aminoalkyl ester having a COO ester bond group, and dimethyl (or diethyl) aminoalkane having an OOC ester bond group. Alkyl acid, N-[(dimethylamino) (or (diethylamino)) alkyl] alkaneamide having an amide bond group of CONH, Dimethyl (or diethyl) aminoalkanoic acid alkylamide having an amide bond group of NHCO, O ether bond N, N-dimethyl (or diethyl) alkyloxyalkaneamine having a group.
一般式(2)で表される第三級アミン化合物のうち、COOのエステル結合基を有するアルカン酸−ジメチル(もしくはジエチル)アミノアルキルエステルとしては、炭素数4〜18の飽和脂肪酸または飽和脂肪酸ハロゲン化物と、炭素数1〜4のヒドロキシアルキル基を有するジメチル(もしくはジエチル)アミノアルカノールとの反応で得られるような、ペンタン酸1−ジメチルアミノメチルエステル、ヘキサン酸1−ジメチルアミノメチルエステル、ヘプタン酸1−ジメチルアミノメチルエステル、オクタン酸1−ジメチルアミノメチルエステル、ノナン酸1−ジメチルアミノメチルエステル、デカン酸1−ジメチルアミノメチルエステル、ウンデカン酸1−ジメチルアミノメチルエステル、ドデカン酸1−ジメチルアミノメチルエステル、トリデカン酸1−ジメチルアミノメチルエステル、テトラデカン酸1−ジメチルアミノメチルエステル、ペンタデカン酸1−ジメチルアミノメチルエステル、ヘキサデカン酸1−ジメチルアミノメチルエステル、ヘプタデカン酸1−ジメチルアミノメチルエステル、オクタデカン酸1−ジメチルアミノメチルエステル、ペンタン酸2−ジメチルアミノエチルエステル、ヘキサン酸2−ジメチルアミノエチルエステル、ヘプタン酸2−ジメチルアミノエチルエステル、オクタン酸2−ジメチルアミノエチルエステル、ノナン酸2−ジメチルアミノエチルエステル、デカン酸2−ジメチルアミノエチルエステル、ウンデカン酸2−ジメチルアミノエチルエステル、ドデカン酸2−ジメチルアミノエチルエステル、トリデカン酸2−ジメチルアミノエチルエステル、テトラデカン酸2−ジメチルアミノエチルエステル、ペンタデカン酸2−ジメチルアミノエチルエステル、ヘキサデカン酸2−ジメチルアミノエチルエステル、ヘプタデカン酸2−ジメチルアミノエチルエステル、オクタデカン酸2−ジメチルアミノエチルエステル、ペンタン酸3−ジメチルアミノプロピルエステル、ヘキサン酸3−ジメチルアミノプロピルエステル、ヘプタン酸3−ジメチルアミノプロピルエステル、オクタン酸3−ジメチルアミノプロピルエステル、ノナン酸3−ジメチルアミノプロピルエステル、デカン酸3−ジメチルアミノプロピルエステル、ウンデカン酸3−ジメチルアミノプロピルエステル、ドデカン酸3−ジメチルアミノプロピルエステル、トリデカン酸3−ジメチルアミノプロピルエステル、テトラデカン酸3−ジメチルアミノプロピルエステル、ペンタデカン酸3−ジメチルアミノプロピルエステル、ヘキサデカン酸3−ジメチルアミノプロピルエステル、ヘプタデカン酸3−ジメチルアミノプロピルエステル、オクタデカン酸3−ジメチルアミノプロピルエステル、ペンタン酸4−ジメチルアミノブチルエステル、ヘキサン酸4−ジメチルアミノブチルエステル、ヘプタン酸4−ジメチルアミノブチルエステル、オクタン酸4−ジメチルアミノブチルエステル、ノナン酸4−ジメチルアミノブチルエステル、デカン酸4−ジメチルアミノブチルエステル、ウンデカン酸4−ジメチルアミノブチルエステル、ドデカン酸4−ジメチルアミノブチルエステル、トリデカン酸4−ジメチルアミノブチルエステル、テトラデカン酸4−ジメチルアミノブチルエステル、ペンタデカン酸4−ジメチルアミノブチルエステル、ヘキサデカン酸4−ジメチルアミノブチルエステル、ヘプタデカン酸4−ジメチルアミノブチルエステル、オクタデカン酸4−ジメチルアミノブチルエステル、ペンタン酸1−ジエチルアミノメチルエステル、ヘキサン酸1−ジエチルアミノメチルエステル、ヘプタン酸1−ジエチルアミノメチルエステル、オクタン酸1−ジエチルアミノメチルエステル、ノナン酸1−ジエチルアミノメチルエステル、デカン酸1−ジエチルアミノメチルエステル、ウンデカン酸1−ジエチルアミノメチルエステル、ドデカン酸1−ジエチルアミノメチルエステル、トリデカン酸1−ジエチルアミノメチルエステル、テトラデカン酸1−ジエチルアミノメチルエステル、ペンタデカン酸1−ジエチルアミノメチルエステル、ヘキサデカン酸1−ジエチルアミノメチルエステル、ヘプタデカン酸1−ジエチルアミノメチルエステル、オクタデカン酸1−ジエチルアミノメチルエステル、ペンタン酸2−ジエチルアミノエチルエステル、ヘキサン酸2−ジエチルアミノエチルエステル、ヘプタン酸2−ジエチルアミノエチルエステル、オクタン酸2−ジエチルアミノエチルエステル、ノナン酸2−ジエチルアミノエチルエステル、デカン酸2−ジエチルアミノエチルエステル、ウンデカン酸2−ジエチルアミノエチルエステル、ドデカン酸2−ジエチルアミノエチルエステル、トリデカン酸2−ジエチルアミノエチルエステル、テトラデカン酸2−ジエチルアミノエチルエステル、ペンタデカン酸2−ジエチルアミノエチルエステル、ヘキサデカン酸2−ジエチルアミノエチルエステル、ヘプタデカン酸2−ジエチルアミノエチルエステル、オクタデカン酸2−ジエチルアミノエチルエステル、ペンタン酸3−ジエチルアミノプロピルエステル、ヘキサン酸3−ジエチルアミノプロピルエステル、ヘプタン酸3−ジエチルアミノプロピルエステル、オクタン酸3−ジエチルアミノプロピルエステル、ノナン酸3−ジエチルアミノプロピルエステル、デカン酸3−ジエチルアミノプロピルエステル、ウンデカン酸3−ジエチルアミノプロピルエステル、ドデカン酸3−ジエチルアミノプロピルエステル、トリデカン酸3−ジエチルアミノプロピルエステル、テトラデカン酸3−ジエチルアミノプロピルエステル、ペンタデカン酸3−ジエチルアミノプロピルエステル、ヘキサデカン酸3−ジエチルアミノプロピルエステル、ヘプタデカン酸3−ジエチルアミノプロピルエステル、オクタデカン酸3−ジエチルアミノプロピルエステル、ペンタン酸4−ジエチルアミノブチルエステル、ヘキサン酸4−ジエチルアミノブチルエステル、ヘプタン酸4−ジエチルアミノブチルエステル、オクタン酸4−ジエチルアミノブチルエステル、ノナン酸4−ジエチルアミノブチルエステル、デカン酸4−ジエチルアミノブチルエステル、ウンデカン酸4−ジエチルアミノブチルエステル、ドデカン酸4−ジエチルアミノブチルエステル、トリデカン酸4−ジエチルアミノブチルエステル、テトラデカン酸4−ジエチルアミノブチルエステル、ペンタデカン酸4−ジエチルアミノブチルエステル、ヘキサデカン酸4−ジエチルアミノブチルエステル、ヘプタデカン酸4−ジエチルアミノブチルエステル、オクタデカン酸4−ジエチルアミノブチルエステルなどが挙げられる。 Among the tertiary amine compounds represented by the general formula (2), the alkanoic acid-dimethyl (or diethyl) aminoalkyl ester having an ester bond group of COO is a saturated fatty acid or saturated fatty acid halogen having 4 to 18 carbon atoms. Pentanoic acid 1-dimethylaminomethyl ester, hexanoic acid 1-dimethylaminomethyl ester, heptanoic acid, which can be obtained by the reaction of a compound with dimethyl (or diethyl) aminoalkanol having a hydroxyalkyl group having 1 to 4 carbon atoms 1-dimethylaminomethyl ester, octanoic acid 1-dimethylaminomethyl ester, nonanoic acid 1-dimethylaminomethyl ester, decanoic acid 1-dimethylaminomethyl ester, undecanoic acid 1-dimethylaminomethyl ester, dodecanoic acid 1-dimethylaminomethyl S Tridecanoic acid 1-dimethylaminomethyl ester, tetradecanoic acid 1-dimethylaminomethyl ester, pentadecanoic acid 1-dimethylaminomethyl ester, hexadecanoic acid 1-dimethylaminomethyl ester, heptadecanoic acid 1-dimethylaminomethyl ester, octadecanoic acid 1 -Dimethylaminomethyl ester, pentanoic acid 2-dimethylaminoethyl ester, hexanoic acid 2-dimethylaminoethyl ester, heptanoic acid 2-dimethylaminoethyl ester, octanoic acid 2-dimethylaminoethyl ester, nonanoic acid 2-dimethylaminoethyl ester Decanoic acid 2-dimethylaminoethyl ester, undecanoic acid 2-dimethylaminoethyl ester, dodecanoic acid 2-dimethylaminoethyl ester, tridecanoic acid 2-dimethyl Minoethyl ester, tetradecanoic acid 2-dimethylaminoethyl ester, pentadecanoic acid 2-dimethylaminoethyl ester, hexadecanoic acid 2-dimethylaminoethyl ester, heptadecanoic acid 2-dimethylaminoethyl ester, octadecanoic acid 2-dimethylaminoethyl ester, pentane Acid 3-dimethylaminopropyl ester, hexanoic acid 3-dimethylaminopropyl ester, heptanoic acid 3-dimethylaminopropyl ester, octanoic acid 3-dimethylaminopropyl ester, nonanoic acid 3-dimethylaminopropyl ester, decanoic acid 3-dimethylamino Propyl ester, Undecanoic acid 3-dimethylaminopropyl ester, Dodecanoic acid 3-dimethylaminopropyl ester, Tridecanoic acid 3-dimethylaminopropyl ester Steal, tetradecanoic acid 3-dimethylaminopropyl ester, pentadecanoic acid 3-dimethylaminopropyl ester, hexadecanoic acid 3-dimethylaminopropyl ester, heptadecanoic acid 3-dimethylaminopropyl ester, octadecanoic acid 3-dimethylaminopropyl ester, pentanoic acid 4 -Dimethylaminobutyl ester, hexanoic acid 4-dimethylaminobutyl ester, heptanoic acid 4-dimethylaminobutyl ester, octanoic acid 4-dimethylaminobutyl ester, nonanoic acid 4-dimethylaminobutyl ester, decanoic acid 4-dimethylaminobutyl ester , Undecanoic acid 4-dimethylaminobutyl ester, dodecanoic acid 4-dimethylaminobutyl ester, tridecanoic acid 4-dimethylaminobutyl ester, tetradecane 4-dimethylaminobutyl ester, pentadecanoic acid 4-dimethylaminobutyl ester, hexadecanoic acid 4-dimethylaminobutyl ester, heptadecanoic acid 4-dimethylaminobutyl ester, octadecanoic acid 4-dimethylaminobutyl ester, pentanoic acid 1-diethylaminomethyl ester Hexanoic acid 1-diethylaminomethyl ester, heptanoic acid 1-diethylaminomethyl ester, octanoic acid 1-diethylaminomethyl ester, nonanoic acid 1-diethylaminomethyl ester, decanoic acid 1-diethylaminomethyl ester, undecanoic acid 1-diethylaminomethyl ester, dodecane Acid 1-diethylaminomethyl ester, tridecanoic acid 1-diethylaminomethyl ester, tetradecanoic acid 1-diethylaminomethyl ester Pentadecanoic acid 1-diethylaminomethyl ester, hexadecanoic acid 1-diethylaminomethyl ester, heptadecanoic acid 1-diethylaminomethyl ester, octadecanoic acid 1-diethylaminomethyl ester, pentanoic acid 2-diethylaminoethyl ester, hexanoic acid 2-diethylaminoethyl ester, Heptanoic acid 2-diethylaminoethyl ester, octanoic acid 2-diethylaminoethyl ester, nonanoic acid 2-diethylaminoethyl ester, decanoic acid 2-diethylaminoethyl ester, undecanoic acid 2-diethylaminoethyl ester, dodecanoic acid 2-diethylaminoethyl ester, tridecanoic acid 2-diethylaminoethyl ester, tetradecanoic acid 2-diethylaminoethyl ester, pentadecanoic acid 2-diethyl Aminoethyl ester, hexadecanoic acid 2-diethylaminoethyl ester, heptadecanoic acid 2-diethylaminoethyl ester, octadecanoic acid 2-diethylaminoethyl ester, pentanoic acid 3-diethylaminopropyl ester, hexanoic acid 3-diethylaminopropyl ester, heptanoic acid 3-diethylaminopropyl Ester, octanoic acid 3-diethylaminopropyl ester, nonanoic acid 3-diethylaminopropyl ester, decanoic acid 3-diethylaminopropyl ester, undecanoic acid 3-diethylaminopropyl ester, dodecanoic acid 3-diethylaminopropyl ester, tridecanoic acid 3-diethylaminopropyl ester, Tetradecanoic acid 3-diethylaminopropyl ester, pentadecanoic acid 3-diethylaminopropyl ester Ester, hexadecanoic acid 3-diethylaminopropyl ester, heptadecanoic acid 3-diethylaminopropyl ester, octadecanoic acid 3-diethylaminopropyl ester, pentanoic acid 4-diethylaminobutyl ester, hexanoic acid 4-diethylaminobutyl ester, heptanoic acid 4-diethylaminobutyl ester, Octanoic acid 4-diethylaminobutyl ester, nonanoic acid 4-diethylaminobutyl ester, decanoic acid 4-diethylaminobutyl ester, undecanoic acid 4-diethylaminobutyl ester, dodecanoic acid 4-diethylaminobutyl ester, tridecanoic acid 4-diethylaminobutyl ester, tetradecanoic acid 4-diethylaminobutyl ester, pentadecanoic acid 4-diethylaminobutyl ester, hexadeca Acid 4-diethylamino-butyl ester, heptadecanoic acid 4-diethylamino-butyl ester, and the like octadecanoic acid 4-diethylamino-butyl ester.
一般式(2)で表される第三級アミン化合物のうち、OOCのエステル結合基を有するジメチル(もしくはジエチル)アミノアルカン酸アルキルとしては、炭素数3〜17の飽和脂肪族アルコールと、炭素数2〜5のカルボキシアルキル基を有するジメチル(もしくはジエチル)アミノアルカン酸との反応で得られるような、2−(ジメチルアミノ)酢酸ブチル、2−(ジメチルアミノ)酢酸ペンチル、2−(ジメチルアミノ)酢酸ヘキシル、2−(ジメチルアミノ)酢酸ヘプチル、2−(ジメチルアミノ)酢酸オクチル、2−(ジメチルアミノ)酢酸ノニル、2−(ジメチルアミノ)酢酸デシル、2−(ジメチルアミノ)酢酸ウンデシル、2−(ジメチルアミノ)酢酸ドデシル、2−(ジメチルアミノ)酢酸トリデシル、2−(ジメチルアミノ)酢酸テトラデシル、2−(ジメチルアミノ)酢酸ペンタデシル、2−(ジメチルアミノ)酢酸ヘキサデシル、2−(ジメチルアミノ)酢酸ヘプタデシル、3−(ジメチルアミノ)プロパン酸ブチル、3−(ジメチルアミノ)プロパン酸ペンチル、3−(ジメチルアミノ)プロパン酸ヘキシル、3−(ジメチルアミノ)プロパン酸ヘプチル、3−(ジメチルアミノ)プロパン酸オクチル、3−(ジメチルアミノ)プロパン酸ノニル、3−(ジメチルアミノ)プロパン酸デシル、3−(ジメチルアミノ)プロパン酸ウンデシル、3−(ジメチルアミノ)プロパン酸ドデシル、3−(ジメチルアミノ)プロパン酸トリデシル、3−(ジメチルアミノ)プロパン酸テトラデシル、3−(ジメチルアミノ)プロパン酸ペンタデシル、3−(ジメチルアミノ)プロパン酸ヘキサデシル、3−(ジメチルアミノ)プロパン酸ヘプタデシル、4−(ジメチルアミノ)ブタン酸ブチル、4−(ジメチルアミノ)ブタン酸ペンチル、4−(ジメチルアミノ)ブタン酸ヘキシル、4−(ジメチルアミノ)ブタン酸ヘプチル、4−(ジメチルアミノ)ブタン酸オクチル、4−(ジメチルアミノ)ブタン酸ノニル、4−(ジメチルアミノ)ブタン酸デシル、4−(ジメチルアミノ)ブタン酸ウンデシル、4−(ジメチルアミノ)ブタン酸ドデシル、4−(ジメチルアミノ)ブタン酸トリデシル、4−(ジメチルアミノ)ブタン酸テトラデシル、4−(ジメチルアミノ)ブタン酸ペンタデシル、4−(ジメチルアミノ)ブタン酸ヘキサデシル、4−(ジメチルアミノ)ブタン酸ヘプタデシル、5−(ジメチルアミノ)ペンタン酸ブチル、5−(ジメチルアミノ)ペンタン酸ペンチル、5−(ジメチルアミノ)ペンタン酸ヘキシル、5−(ジメチルアミノ)ペンタン酸ヘプチル、5−(ジメチルアミノ)ペンタン酸オクチル、5−(ジメチルアミノ)ペンタン酸ノニル、5−(ジメチルアミノ)ペンタン酸デシル、5−(ジメチルアミノ)ペンタン酸ウンデシル、5−(ジメチルアミノ)ペンタン酸ドデシル、5−(ジメチルアミノ)ペンタン酸トリデシル、5−(ジメチルアミノ)ペンタン酸テトラデシル、5−(ジメチルアミノ)ペンタン酸ペンタデシル、5−(ジメチルアミノ)ペンタン酸ヘキサデシル、5−(ジメチルアミノ)ペンタン酸ヘプタデシル、2−(ジエチルアミノ)酢酸ブチル、2−(ジエチルアミノ)酢酸ペンチル、2−(ジエチルアミノ)酢酸ヘキシル、2−(ジエチルアミノ)酢酸ヘプチル、2−(ジエチルアミノ)酢酸オクチル、2−(ジエチルアミノ)酢酸ノニル、2−(ジエチルアミノ)酢酸デシル、2−(ジエチルアミノ)酢酸ウンデシル、2−(ジエチルアミノ)酢酸ドデシル、2−(ジエチルアミノ)酢酸トリデシル、2−(ジエチルアミノ)酢酸テトラデシル、2−(ジエチルアミノ)酢酸ペンタデシル、2−(ジエチルアミノ)酢酸ヘキサデシル、2−(ジエチルアミノ)酢酸ヘプタデシル、3−(ジエチルアミノ)プロパン酸ブチル、3−(ジエチルアミノ)プロパン酸ペンチル、3−(ジエチルアミノ)プロパン酸ヘキシル、3−(ジエチルアミノ)プロパン酸ヘプチル、3−(ジエチルアミノ)プロパン酸オクチル、3−(ジエチルアミノ)プロパン酸ノニル、3−(ジエチルアミノ)プロパン酸デシル、3−(ジエチルアミノ)プロパン酸ウンデシル、3−(ジエチルアミノ)プロパン酸ドデシル、3−(ジエチルアミノ)プロパン酸トリデシル、3−(ジエチルアミノ)プロパン酸テトラデシル、3−(ジエチルアミノ)プロパン酸ペンタデシル、3−(ジエチルアミノ)プロパン酸ヘキサデシル、3−(ジエチルアミノ)プロパン酸ヘプタデシル、4−(ジエチルアミノ)ブタン酸ブチル、4−(ジエチルアミノ)ブタン酸ペンチル、4−(ジエチルアミノ)ブタン酸ヘキシル、4−(ジエチルアミノ)ブタン酸ヘプチル、4−(ジエチルアミノ)ブタン酸オクチル、4−(ジエチルアミノ)ブタン酸ノニル、4−(ジエチルアミノ)ブタン酸デシル、4−(ジエチルアミノ)ブタン酸ウンデシル、4−(ジエチルアミノ)ブタン酸ドデシル、4−(ジエチルアミノ)ブタン酸トリデシル、4−(ジエチルアミノ)ブタン酸テトラデシル、4−(ジエチルアミノ)ブタン酸ペンタデシル、4−(ジエチルアミノ)ブタン酸ヘキサデシル、4−(ジエチルアミノ)ブタン酸ヘプタデシル、5−(ジエチルアミノ)ペンタン酸ブチル、5−(ジエチルアミノ)ペンタン酸ペンチル、5−(ジエチルアミノ)ペンタン酸ヘキシル、5−(ジエチルアミノ)ペンタン酸ヘプチル、5−(ジエチルアミノ)ペンタン酸オクチル、5−(ジエチルアミノ)ペンタン酸ノニル、5−(ジエチルアミノ)ペンタン酸デシル、5−(ジエチルアミノ)ペンタン酸ウンデシル、5−(ジエチルアミノ)ペンタン酸ドデシル、5−(ジエチルアミノ)ペンタン酸トリデシル、5−(ジエチルアミノ)ペンタン酸テトラデシル、5−(ジエチルアミノ)ペンタン酸ペンタデシル、5−(ジエチルアミノ)ペンタン酸ヘキサデシル、5−(ジエチルアミノ)ペンタン酸ヘプタデシルなどが挙げられる。 Among the tertiary amine compounds represented by the general formula (2), the dimethyl (or diethyl) aminoalkanoic acid alkyl having an OOC ester bond group includes a saturated aliphatic alcohol having 3 to 17 carbon atoms and a carbon number. 2- (dimethylamino) butyl acetate, 2- (dimethylamino) pentyl acetate, 2- (dimethylamino), as obtained by reaction with dimethyl (or diethyl) aminoalkanoic acid having 2 to 5 carboxyalkyl groups Hexyl acetate, 2- (dimethylamino) heptyl acetate, octyl 2- (dimethylamino) acetate, nonyl 2- (dimethylamino) acetate, decyl 2- (dimethylamino) acetate, undecyl 2- (dimethylamino) acetate, 2- (Dimethylamino) dodecyl acetate, 2- (dimethylamino) tridecyl acetate, 2- (dimethyl acetate) B) tetradecyl acetate, 2- (dimethylamino) pentadecyl acetate, 2- (dimethylamino) hexadecyl acetate, 2- (dimethylamino) heptadecyl acetate, butyl 3- (dimethylamino) propanoate, 3- (dimethylamino) propanoic acid Pentyl, hexyl 3- (dimethylamino) propanoate, heptyl 3- (dimethylamino) propanoate, octyl 3- (dimethylamino) propanoate, nonyl 3- (dimethylamino) propanoate, 3- (dimethylamino) propanoic acid Decyl, undecyl 3- (dimethylamino) propanoate, dodecyl 3- (dimethylamino) propanoate, tridecyl 3- (dimethylamino) propanoate, tetradecyl 3- (dimethylamino) propanoate, 3- (dimethylamino) propanoic acid Pentadecyl, 3- (dimethyl) Amino) hexadecyl propanoate, 3- (dimethylamino) heptadecyl propanoate, butyl 4- (dimethylamino) butanoate, pentyl 4- (dimethylamino) butanoate, hexyl 4- (dimethylamino) butanoate, 4- (dimethyl Amino) butanoate heptyl, 4- (dimethylamino) butanoate, 4- (dimethylamino) butanoate nonyl, 4- (dimethylamino) butanoate, 4- (dimethylamino) butanoate, 4- (dimethyl Amino) dodecyl butanoate, tridecyl 4- (dimethylamino) butanoate, tetradecyl 4- (dimethylamino) butanoate, pentadecyl 4- (dimethylamino) butanoate, hexadecyl 4- (dimethylamino) butanoate, 4- (dimethyl Amino) butadecyl butanoate, 5- (dimethyl) Butyl amino), pentyl 5- (dimethylamino) pentanoate, hexyl 5- (dimethylamino) pentanoate, heptyl 5- (dimethylamino) pentanoate, octyl 5- (dimethylamino) pentanoate, 5- (dimethyl Amino) nonyl pentanoate, decyl 5- (dimethylamino) pentanoate, undecyl 5- (dimethylamino) pentanoate, dodecyl 5- (dimethylamino) pentanoate, tridecyl 5- (dimethylamino) pentanoate, 5- (dimethyl Amino) tetradecylpentanoate, pentadecyl 5- (dimethylamino) pentanoate, hexadecyl 5- (dimethylamino) pentanoate, heptadecyl 5- (dimethylamino) pentanoate, butyl 2- (diethylamino) acetate, 2- (diethylamino) acetic acid Pentyl, 2- (di Tylamino) hexyl acetate, 2- (diethylamino) heptyl acetate, 2- (diethylamino) octyl acetate, 2- (diethylamino) acetic acid nonyl, 2- (diethylamino) acetic acid decyl, 2- (diethylamino) acetic acid undecyl, 2- (diethylamino) Dodecyl acetate, 2- (diethylamino) tridecyl acetate, 2- (diethylamino) tetradecyl acetate, 2- (diethylamino) pentadecyl acetate, hexadecyl 2- (diethylamino) acetate, 2- (diethylamino) heptadecyl acetate, 3- (diethylamino) propanoic acid Butyl, pentyl 3- (diethylamino) propanoate, hexyl 3- (diethylamino) propanoate, heptyl 3- (diethylamino) propanoate, octyl 3- (diethylamino) propanoate, 3- (diethylamino ) Nonyl propanoate, decyl 3- (diethylamino) propanoate, undecyl 3- (diethylamino) propanoate, dodecyl 3- (diethylamino) propanoate, tridecyl 3- (diethylamino) propanoate, tetradecyl 3- (diethylamino) propanoate, Pentadecyl 3- (diethylamino) propanoate, hexadecyl 3- (diethylamino) propanoate, heptadecyl 3- (diethylamino) propanoate, butyl 4- (diethylamino) butanoate, pentyl 4- (diethylamino) butanoate, 4- (diethylamino) Hexyl butanoate, heptyl 4- (diethylamino) butanoate, octyl 4- (diethylamino) butanoate, nonyl 4- (diethylamino) butanoate, decyl 4- (diethylamino) butanoate, 4- (diethylamino) B) undecyl butanoate, 4- (diethylamino) butanoyl butanoate, tridecyl 4- (diethylamino) butanoate, tetradecyl 4- (diethylamino) butanoate, pentadecyl 4- (diethylamino) butanoate, hexadecyl 4- (diethylamino) butanoate 4- (diethylamino) butanoic acid heptadecyl, 5- (diethylamino) pentanoic acid butyl, 5- (diethylamino) pentanoic acid pentyl, 5- (diethylamino) pentanoic acid hexyl, 5- (diethylamino) pentanoic acid heptyl, 5- (diethylamino) ) Octyl pentanoate, 5- (diethylamino) pentanoate nonyl, 5- (diethylamino) pentylate decyl, 5- (diethylamino) pentanoate undecyl, 5- (diethylamino) pentanoate dodecyl, 5- (die Arylamino) pentanoic acid tridecyl, 5- (diethylamino) pentanoic acid tetradecyl, 5- (diethylamino) pentanoic acid pentadecyl, 5- (diethylamino) pentanoic acid hexadecyl, etc. 5- (diethylamino) heptadecyl pentanoic acid.
一般式(2)で表される第三級アミン化合物のうち、CONHのアミド結合基を有するN−[(ジメチルアミノ)(もしくはジエチルアミノ)アルキル]アルカンアミドとしては、炭素数4〜18の飽和脂肪酸または飽和脂肪酸ハロゲン化物と、炭素数1〜4のアルキレン鎖を有するN,N‐ジメチル(もしくはジエチル)アルキレンジアミンとの反応で得られるような、N−[1−(ジメチルアミノ)メチル]ペンタンアミド、N−[1−(ジメチルアミノ)メチル]へキサンアミド、N−[1−(ジメチルアミノ)メチル]ヘプタンアミド、N−[1−(ジメチルアミノ)メチル]オクタンアミド、N−[1−(ジメチルアミノ)メチル]ノナンアミド、N−[1−(ジメチルアミノ)メチル]デカンアミド、N−[1−(ジメチルアミノ)メチル]ウンデカンアミド、N−[1−(ジメチルアミノ)メチル]ドデカンアミド、N−[1−(ジメチルアミノ)メチル]トリデカンアミド、N−[1−(ジメチルアミノ)メチル]テトラデカンアミド、N−[1−(ジメチルアミノ)メチル]ペンタデカンアミド、N−[1−(ジメチルアミノ)メチル]ヘキサデカンアミド、N−[1−(ジメチルアミノ)メチル]ヘプタデカンアミド、N−[1−(ジメチルアミノ)メチル]オクタデカンアミド、N−[2−(ジメチルアミノ)エチル]ペンタンアミド、N−[2−(ジメチルアミノ)エチル]へキサンアミド、N−[2−(ジメチルアミノ)エチル]ヘプタンアミド、N−[2−(ジメチルアミノ)エチル]オクタンアミド、N−[2−(ジメチルアミノ)エチル]ノナンアミド、N−[2−(ジメチルアミノ)エチル]デカンアミド、N−[2−(ジメチルアミノ)エチル]ウンデカンアミド、N−[2−(ジメチルアミノ)エチル]ドデカンアミド、N−[2−(ジメチルアミノ)エチル]トリデカンアミド、N−[2−(ジメチルアミノ)エチル]テトラデカンアミド、N−[2−(ジメチルアミノ)エチル]ペンタデカンアミド、N−[2−(ジメチルアミノ)エチル]ヘキサデカンアミド、N−[2−(ジメチルアミノ)エチル]ヘプタデカンアミド、N−[2−(ジメチルアミノ)エチル]オクタデカンアミド、N−[3−(ジメチルアミノ)プロピル]ペンタンアミド、N−[3−(ジメチルアミノ)プロピル]へキサンアミド、N−[3−(ジメチルアミノ)プロピル]ヘプタンアミド、N−[3−(ジメチルアミノ)プロピル]オクタンアミド、N−[3−(ジメチルアミノ)プロピル]ノナンアミド、N−[3−(ジメチルアミノ)プロピル]デカンアミド、N−[3−(ジメチルアミノ)プロピル]ウンデカンアミド、N−[3−(ジメチルアミノ)プロピル]ドデカンアミド、N−[3−(ジメチルアミノ)プロピル]トリデカンアミド、N−[3−(ジメチルアミノ)プロピル]テトラデカンアミド、N−[3−(ジメチルアミノ)プロピル]ペンタデカンアミド、N−[3−(ジメチルアミノ)プロピル]ヘキサデカンアミド、N−[3−(ジメチルアミノ)プロピル]ヘプタデカンアミド、N−[3−(ジメチルアミノ)プロピル]オクタデカンアミド、N−[4−(ジメチルアミノ)ブチル]ペンタンアミド、N−[4−(ジメチルアミノ)ブチル]へキサンアミド、N−[4−(ジメチルアミノ)ブチル]ヘプタンアミド、N−[4−(ジメチルアミノ)ブチル]オクタンアミド、N−[4−(ジメチルアミノ)ブチル]ノナンアミド、N−[4−(ジメチルアミノ)ブチル]デカンアミド、N−[4−(ジメチルアミノ)ブチル]ウンデカンアミド、N−[4−(ジメチルアミノ)ブチル]ドデカンアミド、N−[4−(ジメチルアミノ)ブチル]トリデカンアミド、N−[4−(ジメチルアミノ)ブチル]テトラデカンアミド、N−[4−(ジメチルアミノ)ブチル]ペンタデカンアミド、N−[4−(ジメチルアミノ)ブチル]ヘキサデカンアミド、N−[4−(ジメチルアミノ)ブチル]ヘプタデカンアミド、N−[4−(ジメチルアミノ)ブチル]オクタデカンアミド、N−[1−(ジエチルアミノ)メチル]ペンタンアミド、N−[1−(ジエチルアミノ)メチル]へキサンアミド、N−[1−(ジエチルアミノ)メチル]ヘプタンアミド、N−[1−(ジエチルアミノ)メチル]オクタンアミド、N−[1−(ジエチルアミノ)メチル]ノナンアミド、N−[1−(ジエチルアミノ)メチル]デカンアミド、N−[1−(ジエチルアミノ)メチル]ウンデカンアミド、N−[1−(ジエチルアミノ)メチル]ドデカンアミド、N−[1−(ジエチルアミノ)メチル]トリデカンアミド、N−[1−(ジエチルアミノ)メチル]テトラデカンアミド、N−[1−(ジエチルアミノ)メチル]ペンタデカンアミド、N−[1−(ジエチルアミノ)メチル]ヘキサデカンアミド、N−[1−(ジエチルアミノ)メチル]ヘプタデカンアミド、N−[1−(ジエチルアミノ)メチル]オクタデカンアミド、N−[2−(ジエチルアミノ)エチル]ペンタンアミド、N−[2−(ジエチルアミノ)エチル]へキサンアミド、N−[2−(ジエチルアミノ)エチル]ヘプタンアミド、N−[2−(ジエチルアミノ)エチル]オクタンアミド、N−[2−(ジエチルアミノ)エチル]ノナンアミド、N−[2−(ジエチルアミノ)エチル]デカンアミド、N−[2−(ジエチルアミノ)エチル]ウンデカンアミド、N−[2−(ジエチルアミノ)エチル]ドデカンアミド、N−[2−(ジエチルアミノ)エチル]トリデカンアミド、N−[2−(ジエチルアミノ)エチル]テトラデカンアミド、N−[2−(ジエチルアミノ)エチル]ペンタデカンアミド、N−[2−(ジエチルアミノ)エチル]ヘキサデカンアミド、N−[2−(ジエチルアミノ)エチル]ヘプタデカンアミド、N−[2−(ジエチルアミノ)エチル]オクタデカンアミド、N−[3−(ジエチルアミノ)プロピル]ペンタンアミド、N−[3−(ジエチルアミノ)プロピル]へキサンアミド、N−[3−(ジエチルアミノ)プロピル]ヘプタンアミド、N−[3−(ジエチルアミノ)プロピル]オクタンアミド、N−[3−(ジエチルアミノ)プロピル]ノナンアミド、N−[3−(ジエチルアミノ)プロピル]デカンアミド、N−[3−(ジエチルアミノ)プロピル]ウンデカンアミド、N−[3−(ジエチルアミノ)プロピル]ドデカンアミド、N−[3−(ジエチルアミノ)プロピル]トリデカンアミド、N−[3−(ジエチルアミノ)プロピル]テトラデカンアミド、N−[3−(ジエチルアミノ)プロピル]ペンタデカンアミド、N−[3−(ジエチルアミノ)プロピル]ヘキサデカンアミド、N−[3−(ジエチルアミノ)プロピル]ヘプタデカンアミド、N−[3−(ジエチルアミノ)プロピル]オクタデカンアミド、N−[4−(ジエチルアミノ)ブチル]ペンタンアミド、N−[4−(ジエチルアミノ)ブチル]へキサンアミド、N−[4−(ジエチルアミノ)ブチル]ヘプタンアミド、N−[4−(ジエチルアミノ)ブチル]オクタンアミド、N−[4−(ジエチルアミノ)ブチル]ノナンアミド、N−[4−(ジエチルアミノ)ブチル]デカンアミド、N−[4−(ジエチルアミノ)ブチル]ウンデカンアミド、N−[4−(ジエチルアミノ)ブチル]ドデカンアミド、N−[4−(ジエチルアミノ)ブチル]トリデカンアミド、N−[4−(ジエチルアミノ)ブチル]テトラデカンアミド、N−[4−(ジエチルアミノ)ブチル]ペンタデカンアミド、N−[4−(ジエチルアミノ)ブチル]ヘキサデカンアミド、N−[4−(ジエチルアミノ)ブチル]ヘプタデカンアミド、N−[4−(ジエチルアミノ)ブチル]オクタデカンアミドなどが挙げられる。 Among the tertiary amine compounds represented by the general formula (2), N-[(dimethylamino) (or diethylamino) alkyl] alkanamide having an amide bond group of CONH is a saturated fatty acid having 4 to 18 carbon atoms. Or N- [1- (dimethylamino) methyl] pentanamide obtained by reaction of a saturated fatty acid halide with N, N-dimethyl (or diethyl) alkylenediamine having an alkylene chain having 1 to 4 carbon atoms N- [1- (dimethylamino) methyl] hexanamide, N- [1- (dimethylamino) methyl] heptanamide, N- [1- (dimethylamino) methyl] octanamide, N- [1- (dimethyl) Amino) methyl] nonanamide, N- [1- (dimethylamino) methyl] decanamide, N- [1- (dimethylamino) ) Methyl] undecanamide, N- [1- (dimethylamino) methyl] dodecanamide, N- [1- (dimethylamino) methyl] tridecanamide, N- [1- (dimethylamino) methyl] tetradecanamide, N -[1- (dimethylamino) methyl] pentadecanamide, N- [1- (dimethylamino) methyl] hexadecanamide, N- [1- (dimethylamino) methyl] heptadecanamide, N- [1- (dimethylamino) ) Methyl] octadecanamide, N- [2- (dimethylamino) ethyl] pentanamide, N- [2- (dimethylamino) ethyl] hexanamide, N- [2- (dimethylamino) ethyl] heptanamide, N- [2- (Dimethylamino) ethyl] octanamide, N- [2- (dimethylamino) ethyl] nonane N- [2- (dimethylamino) ethyl] decanamide, N- [2- (dimethylamino) ethyl] undecanamide, N- [2- (dimethylamino) ethyl] dodecanamide, N- [2- (dimethyl) Amino) ethyl] tridecanamide, N- [2- (dimethylamino) ethyl] tetradecanamide, N- [2- (dimethylamino) ethyl] pentadecanamide, N- [2- (dimethylamino) ethyl] hexadecanamide, N- [2- (dimethylamino) ethyl] heptadecanamide, N- [2- (dimethylamino) ethyl] octadecanamide, N- [3- (dimethylamino) propyl] pentanamide, N- [3- (dimethyl Amino) propyl] hexanamide, N- [3- (dimethylamino) propyl] heptanamide, N- [3 -(Dimethylamino) propyl] octanamide, N- [3- (dimethylamino) propyl] nonanamide, N- [3- (dimethylamino) propyl] decanamide, N- [3- (dimethylamino) propyl] undecanamide, N- [3- (dimethylamino) propyl] dodecanamide, N- [3- (dimethylamino) propyl] tridecanamide, N- [3- (dimethylamino) propyl] tetradecanamide, N- [3- (dimethyl Amino) propyl] pentadecanamide, N- [3- (dimethylamino) propyl] hexadecanamide, N- [3- (dimethylamino) propyl] heptadecanamide, N- [3- (dimethylamino) propyl] octadecanamide, N- [4- (dimethylamino) butyl] pentanamide, N- [4 (Dimethylamino) butyl] hexanamide, N- [4- (dimethylamino) butyl] heptanamide, N- [4- (dimethylamino) butyl] octanamide, N- [4- (dimethylamino) butyl] nonanamide, N- [4- (dimethylamino) butyl] decanamide, N- [4- (dimethylamino) butyl] undecanamide, N- [4- (dimethylamino) butyl] dodecanamide, N- [4- (dimethylamino) Butyl] tridecanamide, N- [4- (dimethylamino) butyl] tetradecanamide, N- [4- (dimethylamino) butyl] pentadecanamide, N- [4- (dimethylamino) butyl] hexadecanamide, N- [4- (Dimethylamino) butyl] heptadecanamide, N- [4- (dimethylamino) butyl Octadecanamide, N- [1- (diethylamino) methyl] pentanamide, N- [1- (diethylamino) methyl] hexaneamide, N- [1- (diethylamino) methyl] heptanamide, N- [1- (diethylamino) Methyl] octanamide, N- [1- (diethylamino) methyl] nonanamide, N- [1- (diethylamino) methyl] decanamide, N- [1- (diethylamino) methyl] undecanamide, N- [1- (diethylamino) Methyl] dodecanamide, N- [1- (diethylamino) methyl] tridecanamide, N- [1- (diethylamino) methyl] tetradecanamide, N- [1- (diethylamino) methyl] pentadecanamide, N- [1- (Diethylamino) methyl] hexadecanamide, N- [1- (Diethylamino) methyl] heptadecanamide, N- [1- (diethylamino) methyl] octadecanamide, N- [2- (diethylamino) ethyl] pentanamide, N- [2- (diethylamino) ethyl] hexaneamide, N- [2- (diethylamino) ethyl] heptanamide, N- [2- (diethylamino) ethyl] octanamide, N- [2- (diethylamino) ethyl] nonanamide, N- [2- (diethylamino) ethyl] decanamide, N- [2- (Diethylamino) ethyl] undecanamide, N- [2- (diethylamino) ethyl] dodecanamide, N- [2- (diethylamino) ethyl] tridecanamide, N- [2- (diethylamino) ethyl] tetradecanamide N- [2- (Diethylamino) ethyl] pen Decanamide, N- [2- (diethylamino) ethyl] hexadecanamide, N- [2- (diethylamino) ethyl] heptadecanamide, N- [2- (diethylamino) ethyl] octadecanamide, N- [3- (diethylamino) Propyl] pentanamide, N- [3- (diethylamino) propyl] hexanamide, N- [3- (diethylamino) propyl] heptanamide, N- [3- (diethylamino) propyl] octaneamide, N- [3- ( Diethylamino) propyl] nonanamide, N- [3- (diethylamino) propyl] decanamide, N- [3- (diethylamino) propyl] undecanamide, N- [3- (diethylamino) propyl] dodecanamide, N- [3- ( Diethylamino) propyl] tridecanami N- [3- (diethylamino) propyl] tetradecanamide, N- [3- (diethylamino) propyl] pentadecanamide, N- [3- (diethylamino) propyl] hexadecanamide, N- [3- (diethylamino) propyl] Heptadecanamide, N- [3- (diethylamino) propyl] octadecanamide, N- [4- (diethylamino) butyl] pentanamide, N- [4- (diethylamino) butyl] hexaneamide, N- [4- (diethylamino) ) Butyl] heptanamide, N- [4- (diethylamino) butyl] octanamide, N- [4- (diethylamino) butyl] nonanamide, N- [4- (diethylamino) butyl] decanamide, N- [4- (diethylamino) ) Butyl] undecanamide, N- [4- ( Diethylamino) butyl] dodecanamide, N- [4- (diethylamino) butyl] tridecanamide, N- [4- (diethylamino) butyl] tetradecanamide, N- [4- (diethylamino) butyl] pentadecanamide, N- [ 4- (diethylamino) butyl] hexadecanamide, N- [4- (diethylamino) butyl] heptadecanamide, N- [4- (diethylamino) butyl] octadecanamide and the like can be mentioned.
一般式(2)で表される第三級アミン化合物のうち、NHCOのアミド結合基を有するジメチル(もしくはジエチル)アミノアルカン酸アルキルアミドとしては、炭素数3〜17の飽和脂肪族1級アミンと、炭素数2〜5のカルボキシアルキル基を有するジメチル(もしくはジエチル)アミノアルカン酸との反応で得られるような、ジメチルアミノ酢酸ブチルアミド、ジメチルアミノ酢酸ペンチルアミド、ジメチルアミノ酢酸ヘキシルアミド、ジメチルアミノ酢酸ヘプチルアミド、ジメチルアミノ酢酸オクチルアミド、ジメチルアミノ酢酸ノニルアミド、ジメチルアミノ酢酸デシルアミド、ジメチルアミノ酢酸ウンデシルアミド、ジメチルアミノ酢酸ドデシルアミド、ジメチルアミノ酢酸トリデシルアミド、ジメチルアミノ酢酸テトラデシルアミド、ジメチルアミノ酢酸ペンタデシルアミド、ジメチルアミノ酢酸ヘキサデシルアミド、ジメチルアミノ酢酸ヘプタデシルアミド、ジメチルアミノプロパン酸ブチルアミド、ジメチルアミノプロパン酸ペンチルアミド、ジメチルアミノプロパン酸ヘキシルアミド、ジメチルアミノプロパン酸ヘプチルアミド、ジメチルアミノプロパン酸オクチルアミド、ジメチルアミノプロパン酸ノニルアミド、ジメチルアミノプロパン酸デシルアミド、ジメチルアミノプロパン酸ウンデシルアミド、ジメチルアミノプロパン酸ドデシルアミド、ジメチルアミノプロパン酸トリデシルアミド、ジメチルアミノプロパン酸テトラデシルアミド、ジメチルアミノプロパン酸ペンタデシルアミド、ジメチルアミノプロパン酸ヘキサデシルアミド、ジメチルアミノプロパン酸ヘプタデシルアミド、ジメチルアミノブタン酸ブチルアミド、ジメチルアミノブタン酸ペンチルアミド、ジメチルアミノブタン酸ヘキシルアミド、ジメチルアミノブタン酸ヘプチルアミド、ジメチルアミノブタン酸オクチルアミド、ジメチルアミノブタン酸ノニルアミド、ジメチルアミノブタン酸デシルアミド、ジメチルアミノブタン酸ウンデシルアミド、ジメチルアミノブタン酸ドデシルアミド、ジメチルアミノブタン酸トリデシルアミド、ジメチルアミノブタン酸テトラデシルアミド、ジメチルアミノブタン酸ペンタデシルアミド、ジメチルアミノブタン酸ヘキサデシルアミド、ジメチルアミノブタン酸ヘプタデシルアミド、ジメチルアミノペンタン酸ブチルアミド、ジメチルアミノペンタン酸ペンチルアミド、ジメチルアミノペンタン酸ヘキシルアミド、ジメチルアミノペンタン酸ヘプチルアミド、ジメチルアミノペンタン酸オクチルアミド、ジメチルアミノペンタン酸ノニルアミド、ジメチルアミノペンタン酸デシルアミド、ジメチルアミノペンタン酸ウンデシルアミド、ジメチルアミノペンタン酸ドデシルアミド、ジメチルアミノペンタン酸トリデシルアミド、ジメチルアミノペンタン酸テトラデシルアミド、ジメチルアミノペンタン酸ペンタデシルアミド、ジメチルアミノペンタン酸ヘキサデシルアミド、ジメチルアミノペンタン酸ヘプタデシルアミド、ジエチルアミノ酢酸ブチルアミド、ジエチルアミノ酢酸ペンチルアミド、ジエチルアミノ酢酸ヘキシルアミド、ジエチルアミノ酢酸ヘプチルアミド、ジエチルアミノ酢酸オクチルアミド、ジエチルアミノ酢酸ノニルアミド、ジエチルアミノ酢酸デシルアミド、ジエチルアミノ酢酸ウンデシルアミド、ジエチルアミノ酢酸ドデシルアミド、ジエチルアミノ酢酸トリデシルアミド、ジエチルアミノ酢酸テトラデシルアミド、ジエチルアミノ酢酸ペンタデシルアミド、ジエチルアミノ酢酸ヘキサデシルアミド、ジエチルアミノ酢酸ヘプタデシルアミド、ジエチルアミノプロパン酸ブチルアミド、ジエチルアミノプロパン酸ペンチルアミド、ジエチルアミノプロパン酸ヘキシルアミド、ジエチルアミノプロパン酸ヘプチルアミド、ジエチルアミノプロパン酸オクチルアミド、ジエチルアミノプロパン酸ノニルアミド、ジエチルアミノプロパン酸デシルアミド、ジエチルアミノプロパン酸ウンデシルアミド、ジエチルアミノプロパン酸ドデシルアミド、ジエチルアミノプロパン酸トリデシルアミド、ジエチルアミノプロパン酸テトラデシルアミド、ジエチルアミノプロパン酸ペンタデシルアミド、ジエチルアミノプロパン酸ヘキサデシルアミド、ジエチルアミノプロパン酸ヘプタデシルアミド、ジエチルアミノブタン酸ブチルアミド、ジエチルアミノブタン酸ペンチルアミド、ジエチルアミノブタン酸ヘキシルアミド、ジエチルアミノブタン酸ヘプチルアミド、ジエチルアミノブタン酸オクチルアミド、ジエチルアミノブタン酸ノニルアミド、ジエチルアミノブタン酸デシルアミド、ジエチルアミノブタン酸ウンデシルアミド、ジエチルアミノブタン酸ドデシルアミド、ジエチルアミノブタン酸トリデシルアミド、ジエチルアミノブタン酸テトラデシルアミド、ジエチルアミノブタン酸ペンタデシルアミド、ジエチルアミノブタン酸ヘキサデシルアミド、ジエチルアミノブタン酸ヘプタデシルアミド、ジエチルアミノペンタン酸ブチルアミド、ジエチルアミノペンタン酸ペンチルアミド、ジエチルアミノペンタン酸ヘキシルアミド、ジエチルアミノペンタン酸ヘプチルアミド、ジエチルアミノペンタン酸オクチルアミド、ジエチルアミノペンタン酸ノニルアミド、ジエチルアミノペンタン酸デシルアミド、ジエチルアミノペンタン酸ウンデシルアミド、ジエチルアミノペンタン酸ドデシルアミド、ジエチルアミノペンタン酸トリデシルアミド、ジエチルアミノペンタン酸テトラデシルアミド、ジエチルアミノペンタン酸ペンタデシルアミド、ジエチルアミノペンタン酸ヘキサデシルアミド、ジエチルアミノペンタン酸ヘプタデシルアミドなどが挙げられる。 Among the tertiary amine compounds represented by the general formula (2), the dimethyl (or diethyl) aminoalkanoic acid alkylamide having an NHCO amide bond group includes a saturated aliphatic primary amine having 3 to 17 carbon atoms and Dimethylaminoacetic acid butyramide, dimethylaminoacetic acid pentylamide, dimethylaminoacetic acid hexylamide, dimethylaminoacetic acid heptyl, obtained by reaction with dimethyl (or diethyl) aminoalkanoic acid having a carboxyalkyl group having 2 to 5 carbon atoms Amides, dimethylaminoacetic acid octylamide, dimethylaminoacetic acid nonylamide, dimethylaminoacetic acid decylamide, dimethylaminoacetic acid undecylamide, dimethylaminoacetic acid dodecylamide, dimethylaminoacetic acid tridecylamide, dimethylaminoacetic acid tetradecylamide Dimethylaminoacetic acid pentadecylamide, dimethylaminoacetic acid hexadecylamide, dimethylaminoacetic acid heptadecylamide, dimethylaminopropanoic acid butyramide, dimethylaminopropanoic acid pentylamide, dimethylaminopropanoic acid hexylamide, dimethylaminopropanoic acid heptylamide, Dimethylaminopropanoic acid octylamide, dimethylaminopropanoic acid nonylamide, dimethylaminopropanoic acid decylamide, dimethylaminopropanoic acid undecylamide, dimethylaminopropanoic acid dodecylamide, dimethylaminopropanoic acid tridecylamide, dimethylaminopropanoic acid tetradecylamide, Dimethylaminopropanoic acid pentadecylamide, dimethylaminopropanoic acid hexadecylamide, dimethylamino Lopanic acid heptadecylamide, dimethylaminobutanoic acid butyramide, dimethylaminobutanoic acid pentylamide, dimethylaminobutanoic acid hexylamide, dimethylaminobutanoic acid heptylamide, dimethylaminobutanoic acid octylamide, dimethylaminobutanoic acid nonylamide, dimethylaminobutanoic acid Decylamide, dimethylaminobutanoic acid undecylamide, dimethylaminobutanoic acid dodecylamide, dimethylaminobutanoic acid tridecylamide, dimethylaminobutanoic acid tetradecylamide, dimethylaminobutanoic acid pentadecylamide, dimethylaminobutanoic acid hexadecylamide, dimethyl Aminobutanoic acid heptadecylamide, dimethylaminopentanoic acid butyramide, dimethylaminopentanoic acid pentylamide, dimethylamino Pentanoic acid hexylamide, dimethylaminopentanoic acid heptylamide, dimethylaminopentanoic acid octylamide, dimethylaminopentanoic acid nonylamide, dimethylaminopentanoic acid decylamide, dimethylaminopentanoic acid undecylamide, dimethylaminopentanoic acid dodecylamide, dimethylaminopentanoic acid Tridecylamide, dimethylaminopentanoic acid tetradecylamide, dimethylaminopentanoic acid pentadecylamide, dimethylaminopentanoic acid hexadecylamide, dimethylaminopentanoic acid heptadecylamide, diethylaminoacetic acid butyramide, diethylaminoacetic acid pentylamide, diethylaminoacetic acid hexylamide, Diethylaminoacetic acid heptylamide, diethylaminoacetic acid octylamide, diethylaminovinegar Nonylamide, diethylaminoacetic acid decylamide, diethylaminoacetic acid undecylamide, diethylaminoacetic acid dodecylamide, diethylaminoacetic acid tridecylamide, diethylaminoacetic acid tetradecylamide, diethylaminoacetic acid pentadecylamide, diethylaminoacetic acid hexadecylamide, diethylaminoacetic acid heptadecylamide, diethylaminopropanoic acid Butylamide, diethylaminopropanoic acid pentylamide, diethylaminopropanoic acid hexylamide, diethylaminopropanoic acid heptylamide, diethylaminopropanoic acid octylamide, diethylaminopropanoic acid nonylamide, diethylaminopropanoic acid decylamide, diethylaminopropanoic acid undecylamide, diethylaminopropanoic acid dodecylamide, die Ruaminopropanoic acid tridecylamide, diethylaminopropanoic acid tetradecylamide, diethylaminopropanoic acid pentadecylamide, diethylaminopropanoic acid hexadecylamide, diethylaminopropanoic acid heptadecylamide, diethylaminobutanoic acid butyramide, diethylaminobutanoic acid pentylamide, diethylaminobutanoic acid Hexylamide, diethylaminobutanoic acid heptylamide, diethylaminobutanoic acid octylamide, diethylaminobutanoic acid nonylamide, diethylaminobutanoic acid decylamide, diethylaminobutanoic acid undecylamide, diethylaminobutanoic acid dodecylamide, diethylaminobutanoic acid tridecylamide, diethylaminobutanoic acid tetradecylamide Amide, pentadecyl diethylaminobutanoate Amide, diethylaminobutanoic acid hexadecylamide, diethylaminobutanoic acid heptadecylamide, diethylaminopentanoic acid butyramide, diethylaminopentanoic acid pentylamide, diethylaminopentanoic acid hexylamide, diethylaminopentanoic acid heptylamide, diethylaminopentanoic acid octylamide, diethylaminopentanoic acid nonylamide, Diethylaminopentanoic acid decylamide, diethylaminopentanoic acid undecylamide, diethylaminopentanoic acid dodecylamide, diethylaminopentanoic acid tridecylamide, diethylaminopentanoic acid tetradecylamide, diethylaminopentanoic acid pentadecylamide, diethylaminopentanoic acid hexadecylamide, diethylaminopentanoic acid hepta Decylamide And the like.
一般式(2)で表される第三級アミン化合物のうち、Oのエーテル結合基を有するN,N−ジメチル(もしくはジエチル)アルキルオキシアルカンアミンとしては、炭素数3〜17のハロゲン化アルキルと、炭素数1〜4のヒドロキシアルキル基を有するジメチル(もしくはジエチル)アミノアルカノールとの反応で得られるような、N,N−ジメチルブトキシメタンアミン、N,N−ジメチルペンチルオキシメタンアミン、N,N−ジメチルヘキシルオキシメタンアミン、N,N−ジメチルヘプチルオキシメタンアミン、N,N−ジメチルオクチルオキシメタンアミン、N,N−ジメチルノニルオキシメタンアミン、N,N−ジメチルデシルオキシメタンアミン、N,N−ジメチルウンデシルオキシメタンアミン、N,N−ジメチルドデシルオキシメタンアミン、N,N−ジメチルトリデシルオキシメタンアミン、N,N−ジメチルテトラデシルオキシメタンアミン、N,N−ジメチルペンタデシルオキシメタンアミン、N,N−ジメチルヘキサデシルオキシメタンアミン、N,N−ジメチルヘプタデシルオキシメタンアミン、N,N−ジメチル−2−ブトキシエタンアミン、N,N−ジメチル−2−ペンチルオキシエタンアミン、N,N−ジメチル−2−ヘキシルオキシエタンアミン、N,N−ジメチル−2−ヘプチルオキシエタンアミン、N,N−ジメチル−2−オクチルオキシエタンアミン、N,N−ジメチル−2−ノニルオキシエタンアミン、N,N−ジメチル−2−デシルオキシエタンアミン、N,N−ジメチル−2−ウンデシルオキシエタンアミン、N,N−ジメチル−2−ドデシルオキシエタンアミン、N,N−ジメチル−2−トリデシルオキシエタンアミン、N,N−ジメチル−2−テトラデシルオキシエタンアミン、N,N−ジメチル−2−ペンタデシルオキシエタンアミン、N,N−ジメチル−2−ヘキサデシルオキシエタンアミン、N,N−ジメチル−2−ヘプタデシルオキシエタンアミン、N,N−ジメチル−3−ブトキシプロパン−1−アミン、N,N−ジメチル−3−ペンチルオキシプロパン−1−アミン、N,N−ジメチル−3−ヘキシルオキシプロパン−1−アミン、N,N−ジメチル−3−ヘプチルオキシプロパン−1−アミン、N,N−ジメチル−3−オクチルオキシプロパン−1−アミン、N,N−ジメチル−3−ノニルオキシプロパン−1−アミン、N,N−ジメチル−3−デシルオキシプロパン−1−アミン、N,N−ジメチル−3−ウンデシルオキシプロパン−1−アミン、N,N−ジメチル−3−ドデシルオキシプロパン−1−アミン、N,N−ジメチル−3−トリデシルオキシプロパン−1−アミン、N,N−ジメチル−3−テトラデシルオキシプロパン−1−アミン、N,N−ジメチル−3−ペンタデシルオキシプロパン−1−アミン、N,N−ジメチル−3−ヘキサデシルオキシプロパン−1−アミン、N,N−ジメチル−3−ヘプタデシルオキシプロパン−1−アミン、N,N−ジメチル−4−ブトキシブタン−1−アミン、N,N−ジメチル−4−ペンチルオキシブタン−1−アミン、N,N−ジメチル−4−ヘキシルオキシブタン−1−アミン、N,N−ジメチル−4−ヘプチルオキシブタン−1−アミン、N,N−ジメチル−4−オクチルオキシブタン−1−アミン、N,N−ジメチル−4−ノニルオキシブタン−1−アミン、N,N−ジメチル−4−デシルオキシブタン−1−アミン、N,N−ジメチル−4−ウンデシルオキシブタン−1−アミン、N,N−ジメチル−4−ドデシルオキシブタン−1−アミン、N,N−ジメチル−4−トリデシルオキシブタン−1−アミン、N,N−ジメチル−4−テトラデシルオキシブタン−1−アミン、N,N−ジメチル−4−ペンタデシルオキシブタン−1−アミン、N,N−ジメチル−4−ヘキサデシルオキシブタン−1−アミン、N,N−ジメチル−4−ヘプタデシルオキシブタン−1−アミン、N,N−ジエチルブトキシメタンアミン、N,N−ジエチルペンチルオキシメタンアミン、N,N−ジエチルヘキシルオキシメタンアミン、N,N−ジエチルヘプチルオキシメタンアミン、N,N−ジエチルオクチルオキシメタンアミン、N,N−ジエチルノニルオキシメタンアミン、N,N−ジエチルデシルオキシメタンアミン、N,N−ジエチルウンデシルオキシメタンアミン、N,N−ジエチルドデシルオキシメタンアミン、N,N−ジエチルトリデシルオキシメタンアミン、N,N−ジエチルテトラデシルオキシメタンアミン、N,N−ジエチルペンタデシルオキシメタンアミン、N,N−ジエチルヘキサデシルオキシメタンアミン、N,N−ジエチルヘプタデシルオキシメタンアミン、N,N−ジエチル−2−ブトキシエタンアミン、N,N−ジエチル−2−ペンチルオキシエタンアミン、N,N−ジエチル−2−ヘキシルオキシエタンアミン、N,N−ジエチル−2−ヘプチルオキシエタンアミン、N,N−ジエチル−2−オクチルオキシエタンアミン、N,N−ジエチル−2−ノニルオキシエタンアミン、N,N−ジエチル−2−デシルオキシエタンアミン、N,N−ジエチル−2−ウンデシルオキシエタンアミン、N,N−ジエチル−2−ドデシルオキシエタンアミン、N,N−ジエチル−2−トリデシルオキシエタンアミン、N,N−ジエチル−2−テトラデシルオキシエタンアミン、N,N−ジエチル−2−ペンタデシルオキシエタンアミン、N,N−ジエチル−2−ヘキサデシルオキシエタンアミン、N,N−ジエチル−2−ヘプタデシルオキシエタンアミン、N,N−ジエチル−3−ブトキシプロパン−1−アミン、N,N−ジエチル−3−ペンチルオキシプロパン−1−アミン、N,N−ジエチル−3−ヘキシルオキシプロパン−1−アミン、N,N−ジエチル−3−ヘプチルオキシプロパン−1−アミン、N,N−ジエチル−3−オクチルオキシプロパン−1−アミン、N,N−ジエチル−3−ノニルオキシプロパン−1−アミン、N,N−ジエチル−3−デシルオキシプロパン−1−アミン、N,N−ジエチル−3−ウンデシルオキシプロパン−1−アミン、N,N−ジエチル−3−ドデシルオキシプロパン−1−アミン、N,N−ジエチル−3−トリデシルオキシプロパン−1−アミン、N,N−ジエチル−3−テトラデシルオキシプロパン−1−アミン、N,N−ジエチル−3−ペンタデシルオキシプロパン−1−アミン、N,N−ジエチル−3−ヘキサデシルオキシプロパン−1−アミン、N,N−ジエチル−3−ヘプタデシルオキシプロパン−1−アミン、N,N−ジエチル−4−ブトキシブタン−1−アミン、N,N−ジエチル−4−ペンチルオキシブタン−1−アミン、N,N−ジエチル−4−ヘキシルオキシブタン−1−アミン、N,N−ジエチル−4−ヘプチルオキシブタン−1−アミン、N,N−ジエチル−4−オクチルオキシブタン−1−アミン、N,N−ジエチル−4−ノニルオキシブタン−1−アミン、N,N−ジエチル−4−デシルオキシブタン−1−アミン、N,N−ジエチル−4−ウンデシルオキシブタン−1−アミン、N,N−ジエチル−4−ドデシルオキシブタン−1−アミン、N,N−ジエチル−4−トリデシルオキシブタン−1−アミン、N,N−ジエチル−4−テトラデシルオキシブタン−1−アミン、N,N−ジエチル−4−ペンタデシルオキシブタン−1−アミン、N,N−ジエチル−4−ヘキサデシルオキシブタン−1−アミン、N,N−ジエチル−4−ヘプタデシルオキシブタン−1−アミンなどが挙げられる。 Among the tertiary amine compounds represented by the general formula (2), N, N-dimethyl (or diethyl) alkyloxyalkaneamines having an O ether bond group include alkyl halides having 3 to 17 carbon atoms and N, N-dimethylbutoxymethanamine, N, N-dimethylpentyloxymethanamine, N, N as obtained by reaction with dimethyl (or diethyl) aminoalkanol having a hydroxyalkyl group having 1 to 4 carbon atoms -Dimethylhexyloxymethanamine, N, N-dimethylheptyloxymethanamine, N, N-dimethyloctyloxymethanamine, N, N-dimethylnonyloxymethanamine, N, N-dimethyldecyloxymethanamine, N, N -Dimethylundecyloxymethanamine, N, N-dimethyldodecy Oxymethanamine, N, N-dimethyltridecyloxymethanamine, N, N-dimethyltetradecyloxymethanamine, N, N-dimethylpentadecyloxymethanamine, N, N-dimethylhexadecyloxymethanamine, N, N-dimethylheptadecyloxymethanamine, N, N-dimethyl-2-butoxyethanamine, N, N-dimethyl-2-pentyloxyethanamine, N, N-dimethyl-2-hexyloxyethanamine, N, N -Dimethyl-2-heptyloxyethanamine, N, N-dimethyl-2-octyloxyethanamine, N, N-dimethyl-2-nonyloxyethanamine, N, N-dimethyl-2-decyloxyethanamine, N , N-dimethyl-2-undecyloxyethanamine, N, N-dimethyl -2-dodecyloxyethanamine, N, N-dimethyl-2-tridecyloxyethanamine, N, N-dimethyl-2-tetradecyloxyethanamine, N, N-dimethyl-2-pentadecyloxyethanamine, N, N-dimethyl-2-hexadecyloxyethanamine, N, N-dimethyl-2-heptadecyloxyethanamine, N, N-dimethyl-3-butoxypropan-1-amine, N, N-dimethyl-3 -Pentyloxypropan-1-amine, N, N-dimethyl-3-hexyloxypropan-1-amine, N, N-dimethyl-3-heptyloxypropan-1-amine, N, N-dimethyl-3-octyl Oxypropan-1-amine, N, N-dimethyl-3-nonyloxypropan-1-amine, N, N-dimethyl-3-de Siloxypropan-1-amine, N, N-dimethyl-3-undecyloxypropan-1-amine, N, N-dimethyl-3-dodecyloxypropan-1-amine, N, N-dimethyl-3-tri Decyloxypropan-1-amine, N, N-dimethyl-3-tetradecyloxypropan-1-amine, N, N-dimethyl-3-pentadecyloxypropan-1-amine, N, N-dimethyl-3- Hexadecyloxypropan-1-amine, N, N-dimethyl-3-heptadecyloxypropan-1-amine, N, N-dimethyl-4-butoxybutan-1-amine, N, N-dimethyl-4-pentyl Oxybutane-1-amine, N, N-dimethyl-4-hexyloxybutane-1-amine, N, N-dimethyl-4-heptyloxybutane-1 Amines, N, N-dimethyl-4-octyloxybutan-1-amine, N, N-dimethyl-4-nonyloxybutan-1-amine, N, N-dimethyl-4-decyloxybutan-1-amine, N, N-dimethyl-4-undecyloxybutan-1-amine, N, N-dimethyl-4-dodecyloxybutan-1-amine, N, N-dimethyl-4-tridecyloxybutan-1-amine, N, N-dimethyl-4-tetradecyloxybutan-1-amine, N, N-dimethyl-4-pentadecyloxybutane-1-amine, N, N-dimethyl-4-hexadecyloxybutane-1-amine N, N-dimethyl-4-heptadecyloxybutan-1-amine, N, N-diethylbutoxymethanamine, N, N-diethylpentyloxymethanamine N, N-diethylhexyloxymethanamine, N, N-diethylheptyloxymethanamine, N, N-diethyloctyloxymethanamine, N, N-diethylnonyloxymethanamine, N, N-diethyldecyloxymethanamine, N, N-diethylundecyloxymethanamine, N, N-diethyldodecyloxymethanamine, N, N-diethyltridecyloxymethanamine, N, N-diethyltetradecyloxymethanamine, N, N-diethylpentadecyl Oxymethanamine, N, N-diethylhexadecyloxymethanamine, N, N-diethylheptadecyloxymethanamine, N, N-diethyl-2-butoxyethanamine, N, N-diethyl-2-pentyloxyethanamine N, N-diethyl-2-hexyl Ruoxyethanamine, N, N-diethyl-2-heptyloxyethanamine, N, N-diethyl-2-octyloxyethanamine, N, N-diethyl-2-nonyloxyethanamine, N, N-diethyl- 2-decyloxyethanamine, N, N-diethyl-2-undecyloxyethanamine, N, N-diethyl-2-dodecyloxyethanamine, N, N-diethyl-2-tridecyloxyethanamine, N, N-diethyl-2-tetradecyloxyethanamine, N, N-diethyl-2-pentadecyloxyethanamine, N, N-diethyl-2-hexadecyloxyethanamine, N, N-diethyl-2-heptadecyl Oxyethanamine, N, N-diethyl-3-butoxypropan-1-amine, N, N-diethyl-3-pen Ruoxypropan-1-amine, N, N-diethyl-3-hexyloxypropan-1-amine, N, N-diethyl-3-heptyloxypropan-1-amine, N, N-diethyl-3-octyloxy Propan-1-amine, N, N-diethyl-3-nonyloxypropan-1-amine, N, N-diethyl-3-decyloxypropan-1-amine, N, N-diethyl-3-undecyloxypropane -1-amine, N, N-diethyl-3-dodecyloxypropan-1-amine, N, N-diethyl-3-tridecyloxypropan-1-amine, N, N-diethyl-3-tetradecyloxypropane -1-amine, N, N-diethyl-3-pentadecyloxypropan-1-amine, N, N-diethyl-3-hexadecyloxypropa -1-amine, N, N-diethyl-3-heptadecyloxypropan-1-amine, N, N-diethyl-4-butoxybutan-1-amine, N, N-diethyl-4-pentyloxybutane-1 -Amine, N, N-diethyl-4-hexyloxybutane-1-amine, N, N-diethyl-4-heptyloxybutane-1-amine, N, N-diethyl-4-octyloxybutane-1-amine N, N-diethyl-4-nonyloxybutan-1-amine, N, N-diethyl-4-decyloxybutan-1-amine, N, N-diethyl-4-undecyloxybutan-1-amine, N, N-diethyl-4-dodecyloxybutan-1-amine, N, N-diethyl-4-tridecyloxybutan-1-amine, N, N-diethyl-4-tetradecylo Xibutan-1-amine, N, N-diethyl-4-pentadecyloxybutan-1-amine, N, N-diethyl-4-hexadecyloxybutan-1-amine, N, N-diethyl-4-heptadecyl And oxybutane-1-amine.
酸無水物のスペーサー基を形成させる無水ハロゲン化酢酸としてのハロゲン原子は、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられ、好ましくは塩素原子、臭素原子であり、具体的には無水クロロ酢酸、無水ブロモ酢酸などが挙げられる。 Examples of the halogen atom as the halogenated acetic anhydride that forms the spacer group of the acid anhydride include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a chlorine atom and a bromine atom, specifically, anhydrous chloro Examples include acetic acid and bromoacetic anhydride.
第三級アミン化合物と無水ハロゲン化酢酸との4級化反応は、アセトン、メチルエチルケトン、アセトニトリル、トルエン、プロピレングリコールなどのグリコール類、エチレングリコールジメチルエーテルなどの溶媒に、無水ハロゲン化酢酸あるいは第三級アミン化合物のいずれかを溶解し、窒素気流中25〜85℃において、第三級アミン化合物あるいは無水ハロゲン化酢酸の他方を含む同溶媒溶液を滴下し、滴下終了後2〜24時間程度撹拌しながら反応させ、反応後減圧下にて反応溶媒を留去し、得られた反応生成物を再結晶あるいはカラムクロマトグラフによって精製することにより、対称構造型のカチオン性ジェミニ型界面活性剤を得ることができる。第三級アミン化合物と無水ハロゲン化酢酸との反応モル比は、無水ハロゲン化酢酸に対して第三級アミン化合物2.0〜4.0倍モル、特に2.0〜2.2倍モルが好ましい。一方、非対称型のカチオン性ジェミニ型界面活性剤を得るには、前記溶媒に無水ハロゲン化酢酸を溶解し、窒素気流中、前記温度において、無水ハロゲン化酢酸に対して0.8〜1.0倍モル、好ましくは0.9〜1.0倍モルの第三級アミン化合物を含む溶媒溶液を滴下し、滴下終了後2〜24時間程度撹拌しながら反応させ、反応後減圧下にて反応溶媒を留去し、得られた反応生成物を再結晶あるいはカラムクロマトグラフによって精製することにより、まず無水ハロゲン化酢酸と1分子の第三級アミン化合物が連結した中間化合物を得る。次いで前記溶媒に連結させた第三級化合物とは異なる第三級アミン化合物あるいは前記中間化合物のいずれかを溶解し、窒素気流中、前記温度において、前記中間化合物あるいは異なる第三級アミン化合物の他方を、中間化合物に対して、異なる第三級アミン化合物1.0〜1.5倍モル、好ましくは1.0〜1.2倍モルとなる量を含む溶媒溶液を滴下し、滴下終了後2〜24時間程度撹拌しながら反応させ、反応後減圧下にて反応溶媒を留去し、得られた反応生成物を再結晶あるいはカラムクロマトグラフによって精製することにより得ることができる。 The quaternization reaction between a tertiary amine compound and halogenated acetic anhydride is carried out by using a glycol such as acetone, methyl ethyl ketone, acetonitrile, toluene, propylene glycol, a solvent such as ethylene glycol dimethyl ether, an anhydrous halogenated acetic acid or a tertiary amine. Dissolve any of the compounds, drop the same solvent solution containing the other of the tertiary amine compound or halogenated acetic anhydride at 25-85 ° C. in a nitrogen stream, and react with stirring for about 2-24 hours after completion of the dropwise addition. After the reaction, the reaction solvent is distilled off under reduced pressure, and the resulting reaction product is purified by recrystallization or column chromatography to obtain a symmetric structure type cationic gemini surfactant. . The reaction molar ratio of the tertiary amine compound and the halogenated acetic anhydride is 2.0 to 4.0 times mol, particularly 2.0 to 2.2 times mol of the tertiary amine compound relative to the halogenated acetic anhydride. preferable. On the other hand, in order to obtain an asymmetric cationic gemini-type surfactant, halogenated acetic anhydride is dissolved in the solvent, and 0.8 to 1.0 with respect to the anhydrous halogenated acetic acid at a temperature in a nitrogen stream. A solvent solution containing a tertiary amine compound, preferably 0.9 to 1.0 moles, of a tertiary amine compound is dropped, and the reaction is allowed to proceed with stirring for about 2 to 24 hours after completion of the dropwise addition. Is distilled off, and the resulting reaction product is purified by recrystallization or column chromatography to first obtain an intermediate compound in which halogenated acetic anhydride and one molecule of a tertiary amine compound are linked. Next, either the tertiary amine compound different from the tertiary compound linked to the solvent or the intermediate compound is dissolved, and the other of the intermediate compound or the different tertiary amine compound is dissolved in a nitrogen stream at the temperature. Is added dropwise with a solvent solution containing 1.0 to 1.5 times mol, preferably 1.0 to 1.2 times mol of a different tertiary amine compound with respect to the intermediate compound. The reaction can be carried out with stirring for about 24 hours, the reaction solvent is distilled off under reduced pressure after the reaction, and the resulting reaction product can be purified by recrystallization or column chromatography.
本発明のカチオン性ジェミニ型界面活性剤は、ドデシルトリメチルアンモニウムクロリドのような1鎖1親水基型の第4級アンモニウム化合物と比較して、臨界ミセル濃度(cmc)が10分の1〜100分の1程度である。cmcは、界面活性剤の有効性を決定するために使用される測定値であり、cmc値が低ければ低いほど、界面活性能は有用である。本発明のカチオン性ジェミニ型界面活性剤は、対称型構造及び/又は非対称型構造の単独であっても、組合わせであっても、さらに1鎖1親水基型の第4級アンモニウム化合物や他の界面活性剤と組合せても使用することができ、添加量は1鎖1親水基型の4級アンモニウム化合物と比較して10分の1〜1000分の1程度の少量でよい。一方、生分解性については官能基により、酸無水物結合>エステル結合>アミド結合>エーテル結合>アルキル基の順に優れる。本発明のカチオン性ジェミニ型界面活性剤は洗剤、柔軟剤、乳化剤、分散剤、帯電防止剤、表面処理剤、抗菌剤、殺生物剤、染料、インクジェット記録用紙、スキンケアローション組成物、ヘアコンディショニング組成物、化粧品組成物、相関移動触媒反応などの用途に有用である。 The cationic gemini-type surfactant of the present invention has a critical micelle concentration (cmc) of 1/10 to 100 minutes as compared with a 1-chain 1-hydrophilic quaternary ammonium compound such as dodecyltrimethylammonium chloride. It is about 1 of. cmc is a measurement used to determine the effectiveness of a surfactant, and the lower the cmc value, the more useful the surfactant activity. The cationic gemini-type surfactant of the present invention may be a symmetric structure and / or an asymmetric structure, alone or in combination, and further a quaternary ammonium compound having a single chain and one hydrophilic group type, and the like. The amount of addition may be as small as about 1/10 to 1/1000 compared with a 1-chain 1-hydrophilic quaternary ammonium compound. On the other hand, the biodegradability is excellent in the order of acid anhydride bond> ester bond> amide bond> ether bond> alkyl group depending on the functional group. The cationic gemini surfactant of the present invention is a detergent, softener, emulsifier, dispersant, antistatic agent, surface treatment agent, antibacterial agent, biocide, dye, ink jet recording paper, skin care lotion composition, hair conditioning composition. It is useful for applications such as products, cosmetic compositions, phase transfer catalysis.
次に実施例を挙げて本発明を更に詳細に説明するが、本発明はこれら実施例のみに限定されるものではない。 EXAMPLES Next, although an Example is given and this invention is demonstrated still in detail, this invention is not limited only to these Examples.
実施例1
アセトン溶媒80mlに、無水クロロ酢酸17.1g(0.1モル)を溶解し、窒素気流中25℃において、ドデカン酸2−ジメチルアミノエチルエステル59.9g(0.21モル)をアセトン溶媒120mlに溶解した溶液を30分間で滴下し、その後50℃で3時間反応した後、溶媒を減圧下留去し、得られた反応粗生成物を再結晶を3回繰り返すことにより精製し白色結晶16.0gを得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 1
Dissolve 17.1 g (0.1 mol) of chloroacetic anhydride in 80 ml of acetone solvent and add 59.9 g (0.21 mol) of dodecanoic acid 2-dimethylaminoethyl ester to 120 ml of acetone solvent in a nitrogen stream at 25 ° C. The dissolved solution was added dropwise over 30 minutes, and after reacting at 50 ° C. for 3 hours, the solvent was distilled off under reduced pressure, and the resulting reaction crude product was purified by repeating recrystallization three times to obtain white crystals 16. 0 g was obtained. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例2
実施例1と同様の方法で、無水クロロ酢酸とヘキサン酸2−ジメチルアミノエチルエステルとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 2
Obtained from chloroacetic anhydride and hexanoic acid 2-dimethylaminoethyl ester in the same manner as in Example 1. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例3
実施例1と同様の方法で、無水クロロ酢酸とオクタデカン酸2−ジメチルアミノエチルエステルとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 3
Obtained from chloroacetic anhydride and octadecanoic acid 2-dimethylaminoethyl ester in the same manner as in Example 1. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例4
実施例1と同様の方法で、無水クロロ酢酸と3−(ジメチルアミノ)プロパン酸ドデシルとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 4
In the same manner as in Example 1, it was obtained from chloroacetic anhydride and dodecyl 3- (dimethylamino) propanoate. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例5
実施例1と同様の方法で、無水クロロ酢酸とN−[2−(ジメチルアミノ)エチル]ウンデカンアミドとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 5
Obtained in the same manner as in Example 1 from chloroacetic anhydride and N- [2- (dimethylamino) ethyl] undecanamide. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例6
実施例1と同様の方法で、無水クロロ酢酸とジメチルアミノプロパン酸ドデシルアミドとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 6
Obtained in the same manner as in Example 1 from chloroacetic anhydride and dimethylaminopropanoic acid dodecylamide. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例7
実施例1と同様の方法で、無水クロロ酢酸とN,N−ジメチル−2−ドデシルオキシエタンアミンとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 7
In the same manner as in Example 1, it was obtained from chloroacetic anhydride and N, N-dimethyl-2-dodecyloxyethanamine. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
実施例8
アセトニトリル溶媒80mlに、無水ブロモ酢酸23.2g(0.1モル)を溶解し、窒素気流中25℃において、オクタン酸2−ジメチルアミノプロピルエステル21.8g(0.095モル)をアセトン溶媒60mlに溶解した溶液を30分間で滴下し、その後50℃で3時間反応した後、溶媒を減圧下留去し、得られた反応粗生成物を再結晶を3回繰り返すことにより精製し目的物である無水ブロモ酢酸とオクタン酸2−ジメチルアミノプロピルエステルが1分子結合した中間化合物15.2g(0.033モル)を得た。
アセトニトリル溶媒50mlに、上記中間化合物13.8g(0.03モル)を溶解し、窒素気流中25℃において、ヘキサデカン酸2−ジメチルアミノエチルエステル10.8g(0.033モル)をアセトン溶媒50mlに溶解した溶液を30分間で滴下し、その後50℃で6時間反応した後、溶媒を減圧下留去し、得られた反応粗生成物を再結晶を3回繰り返すことにより精製した。得られた化合物は、元素分析、1H−NMRによって、非対称の疎水基を持つ本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 8
Dissolve 23.2 g (0.1 mol) of bromoacetic anhydride in 80 ml of acetonitrile solvent, and add 21.8 g (0.095 mol) of octanoic acid 2-dimethylaminopropyl ester to 60 ml of acetone solvent in a nitrogen stream at 25 ° C. The dissolved solution is added dropwise over 30 minutes, and after reacting at 50 ° C. for 3 hours, the solvent is distilled off under reduced pressure, and the resulting reaction crude product is purified by repeating recrystallization three times to be the desired product. 15.2 g (0.033 mol) of an intermediate compound in which one molecule of bromoacetic anhydride and 2-dimethylaminopropyl ester of octanoic acid was bonded was obtained.
13.8 g (0.03 mol) of the above intermediate compound is dissolved in 50 ml of acetonitrile solvent, and 10.8 g (0.033 mol) of hexadecanoic acid 2-dimethylaminoethyl ester is added to 50 ml of acetone solvent at 25 ° C. in a nitrogen stream. The dissolved solution was added dropwise over 30 minutes and then reacted at 50 ° C. for 6 hours. Then, the solvent was distilled off under reduced pressure, and the resulting reaction crude product was purified by repeating recrystallization three times. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention having an asymmetric hydrophobic group by elemental analysis and 1 H-NMR.
実施例9
実施例8と同様の方法で、無水ブロモ酢酸とドデカン酸1−ジメチルアミノメチルエステルとから得た中間化合物とN−[4−(ジエチルアミノ)ブチル]ウンデカンアミドとから得た。得られた化合物は、元素分析、1H−NMRによって構造を確認した。
Example 9
Obtained in the same manner as in Example 8 from an intermediate compound obtained from bromoacetic anhydride and 1-dimethylaminomethyl ester of dodecanoic acid and N- [4- (diethylamino) butyl] undecanamide. The structure of the obtained compound was confirmed by elemental analysis and 1 H-NMR.
実施例10
実施例8と同様の方法で、無水ブロモ酢酸と3−(ジエチルアミノ)プロパン酸ペンチルとから得た中間化合物とジエチルアミノブタン酸ヘキサデシルアミドとから得た。得られた化合物は、元素分析、1H−NMRによって本発明のカチオン性ジェミニ型界面活性剤であることを確認した。
Example 10
In the same manner as in Example 8, it was obtained from an intermediate compound obtained from bromoacetic anhydride and pentyl 3- (diethylamino) propanoate and diethylaminobutanoic acid hexadecylamide. The obtained compound was confirmed to be the cationic gemini surfactant of the present invention by elemental analysis and 1 H-NMR.
比較例1
実施例1と同様の方法で、無水クロロ酢酸とテトラドコサン酸2−ジメチルアミノエチルエステルとから得た。得られた化合物は、元素分析、1H−NMRによって下記化3に示す化合物であることを確認した。
Comparative Example 1
Obtained in the same manner as in Example 1 from chloroacetic anhydride and 2-dimethylaminoethyl tetradocosanoate. The obtained compound was confirmed to be a compound represented by the following chemical formula 3 by elemental analysis and 1 H-NMR.
比較例2
比較例2として、1鎖1極性基型のドデシルトリメチルアンモニウムクロリドを併せて表1に示した。
Comparative Example 2
As Comparative Example 2, the 1-chain 1-polar group type dodecyltrimethylammonium chloride is also shown in Table 1.
比較例3
トルエン溶媒300mLにアジピン酸14.6g(0.1モル)とジメチルエタノールアミン19.6g(0.22モル)、触媒としてp−トルエンスルホン酸0.5gを溶解し、撹拌しながら加熱還流させ、22時間反応した後、溶媒を減圧下留去し、目的物である中間化合物を27.1g得た。モノグライム溶媒300mLに上記中間化合物51.7g(0.2モル)を溶解させ、窒素雰囲気下、ドデカン酸−2−クロロエチルエステル105.1g(0.4モル)を添加しその後85℃で73時間反応した後、再結晶により精製し目的物122.3gを得た。得られた化合物は、元素分析、1H−NMRによって、下記化4に示す化合物であることを確認した。
Comparative Example 3
14.6 g (0.1 mol) of adipic acid, 19.6 g (0.22 mol) of dimethylethanolamine and 0.5 g of p-toluenesulfonic acid as a catalyst were dissolved in 300 mL of toluene solvent, and the mixture was heated to reflux with stirring. After the reaction for 22 hours, the solvent was distilled off under reduced pressure to obtain 27.1 g of the target intermediate compound. 51.7 g (0.2 mol) of the above intermediate compound was dissolved in 300 mL of monoglyme solvent, and 105.1 g (0.4 mol) of dodecanoic acid-2-chloroethyl ester was added under a nitrogen atmosphere, and then at 85 ° C. for 73 hours. After the reaction, purification by recrystallization gave 122.3 g of the desired product. The obtained compound was confirmed to be a compound represented by the following chemical formula 4 by elemental analysis and 1 H-NMR.
比較例4
トルエン溶媒300mLにアジピン酸14.6g(0.1モル)とN,N−ジメチルエチレンジアミン12.8g(0.22モル)を溶解し、撹拌しながら加熱還流させ、22時間反応した後、溶媒を減圧下留去し、目的物である中間化合物を18.6g得た。モノグライム溶媒300mLに上記中間化合物51.1g(0.2モル)を溶解させ、窒素雰囲気下ドデカン酸−2−クロロエチルエステル105.1g(0.4モル)を添加しその後85℃で73時間反応した後、再結晶により精製し目的物112.5gを得た。得られた化合物は、元素分析、1H−NMRによって下記化5に示す化合物であることを確認した。
Comparative Example 4
14.6 g (0.1 mol) of adipic acid and 12.8 g (0.22 mol) of N, N-dimethylethylenediamine were dissolved in 300 mL of toluene solvent, heated under reflux with stirring and reacted for 22 hours. The solvent was distilled off under reduced pressure to obtain 18.6 g of the target intermediate compound. 51.1 g (0.2 mol) of the above intermediate compound was dissolved in 300 mL of monoglyme solvent, 105.1 g (0.4 mol) of dodecanoic acid-2-chloroethyl ester was added under a nitrogen atmosphere, and then reacted at 85 ° C. for 73 hours. And purified by recrystallization to obtain 112.5 g of the desired product. The obtained compound was confirmed to be a compound represented by the following chemical formula 5 by elemental analysis and 1 H-NMR.
実施例1〜10で得られた本発明のカチオン性ジェミニ界面活性剤と、比較例1〜4のカチオン性界面活性剤について臨界ミセル濃度(cmc)測定及び、溶解性試験を行った。結果を表1に示す。試験方法は以下の通りである。 A critical micelle concentration (cmc) measurement and a solubility test were performed on the cationic gemini surfactants of the present invention obtained in Examples 1 to 10 and the cationic surfactants of Comparative Examples 1 to 4. The results are shown in Table 1. The test method is as follows.
臨界ミセル濃度(cmc)
種々の濃度の界面活性剤水溶液(精製水を使用)を調製し、25℃における表面張力をウィルヘルミー型表面張力計にて白金プレート法により求め、表面張力/濃度・関係図を作成し、その屈曲点より臨界ミセル濃度(cmc)を求めた。
Critical micelle concentration (cmc)
Prepare surfactant aqueous solutions of various concentrations (using purified water), determine the surface tension at 25 ° C by the platinum plate method with a Wilhelmy surface tension meter, create surface tension / concentration / relationship diagrams, and bend them The critical micelle concentration (cmc) was determined from the point.
溶解性試験
各界面活性剤1gをイオン交換水10g中に入れ、攪拌したのち室温で24時間静置して沈殿が出るかどうか調べた。判定の基準を次の様に設定した。
○:濁りなし。
△:濁りあり。
×:沈殿物あり。
Solubility test 1 g of each surfactant was put into 10 g of ion-exchanged water, stirred, and then allowed to stand at room temperature for 24 hours to examine whether precipitation occurred. Judgment criteria were set as follows.
○: No turbidity.
Δ: Turbid.
X: There is a precipitate.
(表1)
(Table 1)
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