JP2010144031A - カチオン性ジェミニ型界面活性剤 - Google Patents
カチオン性ジェミニ型界面活性剤 Download PDFInfo
- Publication number
- JP2010144031A JP2010144031A JP2008322336A JP2008322336A JP2010144031A JP 2010144031 A JP2010144031 A JP 2010144031A JP 2008322336 A JP2008322336 A JP 2008322336A JP 2008322336 A JP2008322336 A JP 2008322336A JP 2010144031 A JP2010144031 A JP 2010144031A
- 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.)
- Granted
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 32
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 27
- 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
- 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 abstract description 122
- 230000000694 effects Effects 0.000 abstract description 5
- 125000005647 linker group Chemical group 0.000 abstract description 3
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 2
- 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
- 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
- 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
- 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 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
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- IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 1
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- 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
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- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
【解決手段】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特定なカチオン性ジェミニ型界面活性剤。
【選択図】なし
Description
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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JP2012062246A (ja) * | 2010-09-14 | 2012-03-29 | Miyoshi Oil & Fat Co Ltd | 抗菌性カチオン界面活性剤 |
CN102671576A (zh) * | 2012-05-08 | 2012-09-19 | 中国石油化工股份有限公司 | 一种季铵盐型阳离子表面活性剂及其合成方法 |
JP2013023642A (ja) * | 2011-07-25 | 2013-02-04 | Dainippon Jochugiku Co Ltd | 硬質表面用洗浄剤のすすぎ促進剤 |
JP2014129302A (ja) * | 2012-12-28 | 2014-07-10 | Miyoshi Oil & Fat Co Ltd | 新規ジェミニ型化合物とその製造方法およびそれを用いたカチオン性界面活性剤、分散剤 |
JP2016508287A (ja) * | 2012-12-14 | 2016-03-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 50nm以下のライン間寸法を有するパターン化材料を処理する際におけるアンチパターン崩壊を回避するための、界面活性剤及び疎水剤を含む組成物の使用 |
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JP2012062246A (ja) * | 2010-09-14 | 2012-03-29 | Miyoshi Oil & Fat Co Ltd | 抗菌性カチオン界面活性剤 |
JP2013023642A (ja) * | 2011-07-25 | 2013-02-04 | Dainippon Jochugiku Co Ltd | 硬質表面用洗浄剤のすすぎ促進剤 |
CN102671576A (zh) * | 2012-05-08 | 2012-09-19 | 中国石油化工股份有限公司 | 一种季铵盐型阳离子表面活性剂及其合成方法 |
JP2016508287A (ja) * | 2012-12-14 | 2016-03-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 50nm以下のライン間寸法を有するパターン化材料を処理する際におけるアンチパターン崩壊を回避するための、界面活性剤及び疎水剤を含む組成物の使用 |
JP2014129302A (ja) * | 2012-12-28 | 2014-07-10 | Miyoshi Oil & Fat Co Ltd | 新規ジェミニ型化合物とその製造方法およびそれを用いたカチオン性界面活性剤、分散剤 |
CN111039818A (zh) * | 2019-12-26 | 2020-04-21 | 江南大学 | 一种表面活性剂及其在染发中的应用 |
CN111039818B (zh) * | 2019-12-26 | 2022-07-22 | 江南大学 | 一种表面活性剂及其在染发中的应用 |
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