JP2014131975A - 親水性室温イオン液体とその用途 - Google Patents
親水性室温イオン液体とその用途 Download PDFInfo
- Publication number
- JP2014131975A JP2014131975A JP2013205317A JP2013205317A JP2014131975A JP 2014131975 A JP2014131975 A JP 2014131975A JP 2013205317 A JP2013205317 A JP 2013205317A JP 2013205317 A JP2013205317 A JP 2013205317A JP 2014131975 A JP2014131975 A JP 2014131975A
- Authority
- JP
- Japan
- Prior art keywords
- coo
- ionic liquid
- room temperature
- anion
- stretching vibration
- 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
- 239000011829 room temperature ionic liquid solvent Substances 0.000 title claims abstract description 85
- -1 carboxylate anion Chemical class 0.000 claims abstract description 100
- 150000001450 anions Chemical class 0.000 claims abstract description 69
- 150000001768 cations Chemical class 0.000 claims abstract description 53
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 23
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 102000039446 nucleic acids Human genes 0.000 claims description 22
- 108020004707 nucleic acids Proteins 0.000 claims description 22
- 150000007523 nucleic acids Chemical class 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 230000030788 protein refolding Effects 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000001033 ether group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 abstract description 90
- 239000007788 liquid Substances 0.000 abstract description 38
- 235000018102 proteins Nutrition 0.000 description 68
- 102000004169 proteins and genes Human genes 0.000 description 68
- 108090000623 proteins and genes Proteins 0.000 description 68
- 230000000052 comparative effect Effects 0.000 description 67
- 150000001875 compounds Chemical class 0.000 description 65
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 62
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 61
- 238000005160 1H NMR spectroscopy Methods 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 102000018832 Cytochromes Human genes 0.000 description 35
- 108010052832 Cytochromes Proteins 0.000 description 35
- 238000004090 dissolution Methods 0.000 description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 108090000790 Enzymes Proteins 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 230000007613 environmental effect Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000012620 biological material Substances 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 12
- 238000005259 measurement Methods 0.000 description 12
- 238000005979 thermal decomposition reaction Methods 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910010272 inorganic material Inorganic materials 0.000 description 10
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 10
- 150000004676 glycans Chemical class 0.000 description 9
- 150000002484 inorganic compounds Chemical class 0.000 description 9
- 239000010687 lubricating oil Substances 0.000 description 9
- 229920001282 polysaccharide Polymers 0.000 description 9
- 239000005017 polysaccharide Substances 0.000 description 9
- 102000001554 Hemoglobins Human genes 0.000 description 8
- 108010054147 Hemoglobins Proteins 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 239000007810 chemical reaction solvent Substances 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000008363 phosphate buffer Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 108010088751 Albumins Proteins 0.000 description 6
- 102000009027 Albumins Human genes 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 6
- 102000004196 processed proteins & peptides Human genes 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 229910001928 zirconium oxide Inorganic materials 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000003398 denaturant Substances 0.000 description 5
- 238000007922 dissolution test Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 238000005338 heat storage Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 231100000209 biodegradability test Toxicity 0.000 description 4
- 239000012472 biological sample Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 108010076876 Keratins Proteins 0.000 description 3
- 102000011782 Keratins Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002528 anti-freeze Effects 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 229920001222 biopolymer Polymers 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000002001 electrolyte material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910001510 metal chloride Inorganic materials 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 3
- 230000007928 solubilization Effects 0.000 description 3
- 238000005063 solubilization Methods 0.000 description 3
- 238000012800 visualization Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- 101800000263 Acidic protein Proteins 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 108010007568 Protamines Proteins 0.000 description 2
- 102000007327 Protamines Human genes 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940048914 protamine Drugs 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JEPGPKGGSYXGKV-UHFFFAOYSA-N 2-ethoxybutanoic acid Chemical compound CCOC(CC)C(O)=O JEPGPKGGSYXGKV-UHFFFAOYSA-N 0.000 description 1
- IKAHFTWDTODWID-UHFFFAOYSA-N 2-hydroxyethylazanium;formate Chemical compound [O-]C=O.[NH3+]CCO IKAHFTWDTODWID-UHFFFAOYSA-N 0.000 description 1
- GVSTYPOYHNVKHY-UHFFFAOYSA-N 2-methoxybutanoic acid Chemical compound CCC(OC)C(O)=O GVSTYPOYHNVKHY-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 108010071619 Apolipoproteins Proteins 0.000 description 1
- 102000007592 Apolipoproteins Human genes 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 108090001008 Avidin Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 102000000905 Cadherin Human genes 0.000 description 1
- 108050007957 Cadherin Proteins 0.000 description 1
- 102000000584 Calmodulin Human genes 0.000 description 1
- 108010041952 Calmodulin Proteins 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- 102000011632 Caseins Human genes 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000011022 Chorionic Gonadotropin Human genes 0.000 description 1
- 108010062540 Chorionic Gonadotropin Proteins 0.000 description 1
- 108010004103 Chylomicrons Proteins 0.000 description 1
- 102000002585 Contractile Proteins Human genes 0.000 description 1
- 108010068426 Contractile Proteins Proteins 0.000 description 1
- 238000007400 DNA extraction Methods 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- 102000008857 Ferritin Human genes 0.000 description 1
- 108050000784 Ferritin Proteins 0.000 description 1
- 238000008416 Ferritin Methods 0.000 description 1
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 1
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108010017480 Hemosiderin Proteins 0.000 description 1
- 102100039869 Histone H2B type F-S Human genes 0.000 description 1
- 108010033040 Histones Proteins 0.000 description 1
- 101001035372 Homo sapiens Histone H2B type F-S Proteins 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 102000009151 Luteinizing Hormone Human genes 0.000 description 1
- 108010073521 Luteinizing Hormone Proteins 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 108010063954 Mucins Proteins 0.000 description 1
- 102000015728 Mucins Human genes 0.000 description 1
- 102000003505 Myosin Human genes 0.000 description 1
- 108060008487 Myosin Proteins 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- PPRJBCMIULPNEA-UHFFFAOYSA-N N.N.C(C)O.C(C)O Chemical compound N.N.C(C)O.C(C)O PPRJBCMIULPNEA-UHFFFAOYSA-N 0.000 description 1
- 102000011931 Nucleoproteins Human genes 0.000 description 1
- 108010061100 Nucleoproteins Proteins 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000007982 Phosphoproteins Human genes 0.000 description 1
- 108010089430 Phosphoproteins Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 108010017842 Telomerase Proteins 0.000 description 1
- 102000011923 Thyrotropin Human genes 0.000 description 1
- 108010061174 Thyrotropin Proteins 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- DSBUAQPRJNCZAU-UHFFFAOYSA-N azane;butan-1-ol Chemical compound N.CCCCO DSBUAQPRJNCZAU-UHFFFAOYSA-N 0.000 description 1
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- KQCYDPMUTLJQHT-UHFFFAOYSA-N azane;methanol Chemical compound N.OC.OC KQCYDPMUTLJQHT-UHFFFAOYSA-N 0.000 description 1
- OUETXNFESPZXBQ-UHFFFAOYSA-N azane;pentan-1-ol Chemical compound N.CCCCCO OUETXNFESPZXBQ-UHFFFAOYSA-N 0.000 description 1
- JMJRNNLOJLYQLM-UHFFFAOYSA-N azane;propan-1-ol Chemical compound N.CCCO JMJRNNLOJLYQLM-UHFFFAOYSA-N 0.000 description 1
- KQQCTWHSWXCZHB-UHFFFAOYSA-N azane;propan-2-ol Chemical compound N.CC(C)O KQQCTWHSWXCZHB-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229940075419 choline hydroxide Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 102000034240 fibrous proteins Human genes 0.000 description 1
- 108091005899 fibrous proteins Proteins 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229940028334 follicle stimulating hormone Drugs 0.000 description 1
- 102000034356 gene-regulatory proteins Human genes 0.000 description 1
- 108091006104 gene-regulatory proteins Proteins 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 102000034238 globular proteins Human genes 0.000 description 1
- 108091005896 globular proteins Proteins 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229940084986 human chorionic gonadotropin Drugs 0.000 description 1
- 210000003000 inclusion body Anatomy 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940040129 luteinizing hormone Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229940051875 mucins Drugs 0.000 description 1
- 230000001293 nucleolytic effect Effects 0.000 description 1
- 230000031787 nutrient reservoir activity Effects 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000001799 protein solubilization Methods 0.000 description 1
- 230000007925 protein solubilization Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Lubricants (AREA)
Abstract
【解決手段】カチオン及びアニオンを含む親水性室温イオン性液体であって、該カチオンが下記式(I)の第4級アンモニウムカチオンで、該アニオンがカルボン酸アニオンであることを特徴とする親水性室温イオン液体。
【化1】
(式中、Rは炭素数1〜5の直鎖状又は分岐鎖状のアルキレン基を示し、nは1〜3の整数を示す。)
【選択図】なし
Description
本発明の水素結合性材料に対する溶解又は分散用溶媒は、前記の親水性室温イオン液体を含む。
を示し、rは0〜7の整数を示す。)で表わされる不飽和脂肪族モノカルボン酸アニオンが好ましい。具体的には、例えば、アクリル酸、メタクリル酸、クロトン酸、オレイン酸等からプロトンが解離したアニオンが挙げられる。
<実施例1>
下記式で表される化合物を合成した。
FT−IR(KBr):3552cm-1:O−H伸縮振動 2960cm-1:C−H伸縮振動 1586cm-1:COO-伸縮振動
1H−NMR (D2O 400MHz): δ 3.05 (m, 2H, N+CH 2 CH2OH), δ 3.73 (m, 2H, N+CH2CH 2 OH), δ 8.38 (s, 1H, HCOO-).
13C−NMR (D2O 100MHz): δ 41.3 (N+ CH2CH2OH), δ 57.7 (N+CH2 CH2OH), δ 171.0 (HCOO-).
<実施例2〜61>
下記の表1、2〜7に示した実施例2〜61の化合物を、実施例1と同様の合成方法と、表2〜表7に記載した配合モル比にて合成した。物性値を下記に示す。
<実施例2>
1H−NMR (D2O 400MHz): δ 3.13 (m, 4H, N+CH 2 CH2OH), δ 3.76 (m, 4H, N+CH2CH 2 OH), δ 8.36 (s, 1H,HCOO-).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 171.0 (HCOO-).
<実施例3>
1H−NMR (D2O 400MHz): δ 1.82 (s, 3H, CH 3 COO-), δ 3.04 (m, 2H, N+CH 2 CH2OH), δ 3.77 (m, 2H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 23.3 (CH3COO-), δ 41.2 (N+ CH2CH2OH), δ 57.6 (N+CH2 CH2OH), δ 181.4 (CH3 COO-).
<実施例4>
1H−NMR (D2O 400MHz): δ 1.82 (s, 3H, CH 3 COO-), δ 3.13 (m, 4H, N+CH 2 CH2OH), δ 3.77 (m, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 23.3 (CH3COO-), δ 48.9 (N+ CH2CH2OH), δ 56.6 (N+CH2 CH2OH), δ 181.4 (CH3 COO-).
<実施例5>
1H−NMR (D2O 400MHz): δ 1.84 (s, 3H, CH 3 COO-), δ 3.31(t, 6H, N+CH 2 CH2OH), δ 3.85 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 23.3 (CH3COO-), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 181.4 (CH3 COO-).
<実施例6>
1H−NMR (D2O 400MHz): δ 0.80 (t, 3H, CH 3 CH2), δ 1.44 (m, 2H, CH3CH 2 ), δ 2.06 (t, 2H, CH 2 COO-), δ 3.05 (t, 2H, N+CH 2 CH2OH), δ 3.72 (t, 2H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.2 (CH3CH2), δ 19.3 (CH3 CH2), δ 39.6 (CH2COO-), δ 41.2 (N+ CH2CH2OH), δ 57.6 (N+CH2 CH2OH), δ 184.1 (CH2 COO-).
<実施例7>
1H−NMR (D2O 400MHz): δ 0.79 (t, 3H, CH 3 CH2), δ 1.43 (m, 2H, CH3CH 2 ), δ 2.06 (t, 2H, CH 2 COO-), δ 3.15 (t, 4H, N+CH 2 CH2OH), δ 3.77 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.2 (CH3CH2), δ 19.3 (CH3 CH2), δ 39.6 (CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 184.0 (CH2 COO-).
<実施例8>
1H−NMR (D2O 400MHz): δ 0.82 (t, 3H, CH 3 CH2), δ 1.46 (m, 2H, CH3CH 2 ), δ 2.08 (t, 2H, CH 2 COO-), δ 3.38 (t, 6H, N+CH 2 CH2OH), δ 3.88 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.3 (CH3CH2), δ 19.4 (CH3 CH2), δ 39.6 (CH2COO-), δ 55.2 (N+ CH2CH2OH), δ 55.4 (N+CH2 CH2OH), δ 184.0 (CH2 COO-).
<実施例9>
1H−NMR (D2O 400MHz): δ 0.80 (t, 3H, CH 3 CH2), δ 1.17 (m, 4H, CH3CH 2 CH 2 ), δ 1.44 (m, 2H, CH 2 CH2COO-), δ 2.10 (t, 2H, CH 2 COO-), δ 3.17 (t, 4H, N+CH 2 CH2OH), δ 3.80 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.3 (CH3CH2), δ 21.8 (CH3 CH2), δ 25.5 (CH3CH2 CH2), δ 31.0 (CH2CH2COO-), δ 37.5 (CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 184.2 (CH2 COO-).
<実施例10>
1H−NMR (D2O 400MHz): δ 0.80 (t, 3H, CH 3 CH2), δ 1.19 (m, 4H, CH3CH 2 CH 2 ), δ 1.48 (t, 2H, CH 2 CH2COO-), δ 2.10 (t, 2H, CH 2 COO-), δ 3.38 (t, 6H, N+CH 2 CH2OH), δ 3.88 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.3 (CH3CH2), δ 21.8 (CH3 CH2), δ 25.6 (CH3CH2 CH2), δ 31.0 (CH2CH2COO-), δ 37.6 (CH2COO-), δ 55.3 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 184.3 (CH2 COO-).
<実施例11>
1H−NMR (D2O 400MHz): δ 0.79 (t, 3H, CH 3 CH2), δ 1.21 (m, 8H, CH3(CH 2 )4), δ 1.48 (m, 2H, CH 2 CH2COO-), δ 2.09 (m, 2H, CH 2 COO-), δ 3.14 (t, 4H, N+CH 2 CH2OH), δ 3.78 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.4 (CH3CH2), δ 22.0 (CH3 CH2CH2), δ 25.9 (CH3CH2 CH2), δ 28.3 (CH3CH2CH2 CH2), δ 28.7 (CH2CH2CH2COO-), δ 31.0 (CH2CH2COO-), δ 37.7 (CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.7 (N+CH2 CH2OH), δ 184.3 (CH2 COO-).
<実施例12>
1H−NMR (D2O 400MHz): δ 0.79 (t, 3H, CH 3 CH2), δ 1.21 (m, 12H, CH3(CH 2 )6), δ 1.47 (m, 2H, CH 2 CH2COO-), δ 2.10 (t, 2H, CH 2 COO-), δ 3.15 (t, 4H, N+CH 2 CH2OH), δ 3.79 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 13.5 (CH3CH2), δ 22.2 (CH3 CH2CH2), δ 26.0 (CH3CH2 CH2), δ 28.7 (CH3CH2CH2 CH2), δ 28.8 (CH3CH2CH2CH2 CH2), δ 29.0 ((CH2)2CH2CH2COO-), δ 31.4 (CH2CH2COO-), δ 37.5 (CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.6 (N+CH2 CH2OH), δ 183.6 (CH2 COO-).
<実施例13>
1H−NMR (D2O 400MHz): δ 0.83 (m, 6H, CH 3 (CH2)8CH((CH2)6CH 3 )COO-), δ 1.25 (m, 28H, CH3(CH 2 )8CH((CH 2 )6CH3)COO-), δ 2.10 (m, 1H, CH3(CH2)8CH((CH2)6CH3)COO-), δ 3.01 (t, 2H, N+CH 2 CH2OH), δ 3.74 (t, 2H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 14.1 (CH3CH2), δ 22.7 (CH3 CH--2CH2), δ 26.5 (CH2CH2CHCOO-), δ 30.0 (CH3CH2CH2(CH2)4CH2CH2CH(CH2CH2(CH2)2CH2CH2CH3)COO-,CH2 CH2CHCOO-), δ 31.9 (CH3CH2 CH2), δ 37.9 (CH2 CH(CH2)COO-), δ 41.8 (N+ CH2CH2OH), δ 58.5 (N+CH2 CH2OH), δ 182.1 (COO-).
<実施例14>
1H−NMR (D2O 400MHz): δ 0.83 (m, 6H, CH 3 (CH2)8CH((CH2)6CH 3 )COO-), δ 1.09 (m, 28H, CH3(CH 2 )8CH((CH 2 )6CH3)COO-), δ 2.14 (m, 1H, CH3(CH2)8CH((CH2)6CH3)COO-), δ 3.06 (t, 4H, N+CH 2 CH2OH), δ 3.83 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 14.0 (CH3CH2), δ 22.6 (CH3 CH--2CH2), δ 26.3 (CH2CH2CHCOO-), δ 29.3 (CH3CH2CH2(CH2)4CH2CH2CH(CH2CH2(CH2)2CH2CH2CH3)COO-,CH2 CH2CHCOO-), δ 31.9 (CH3CH2 CH2), δ 37.7 (CH2 CH(CH2)COO-), δ 50.0 (N+ CH2CH2OH), δ 57.5 (N+CH2 CH2OH), δ 181.8 (COO-).
<実施例15>
1H−NMR (D2O 400MHz): δ 0.83 (m, 6H, CH 3 (CH2)8CH((CH2)6CH 3 )COO-), δ 1.26 (m, 28H, CH3(CH 2 )8CH((CH 2 )6CH3)COO-), δ 2.20 (m, 1H, CH3(CH2)8CH((CH2)6CH3)COO-), δ 2.99 (t, 6H, N+CH 2 CH2OH), δ 3.76 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 14.0 (CH3CH2), δ 22.6 (CH3 CH--2CH2), δ 25.7 (CH2CH2CHCOO-), δ 29.3 (CH3CH2CH2(CH2)4CH2CH2CH(CH2CH2(CH2)2CH2CH2CH3)COO-,CH2 CH2CHCOO-), δ 31.9 (CH3CH2 CH2), δ 37.1 (CH2 CH(CH2)COO-), δ 56.8 (N+ CH2CH2OH), δ 57.8 (N+CH2 CH2OH), δ 179.9 (COO-).
<実施例16>
1H−NMR (D2O 400MHz): δ 3.05 (t, 2H, N+CH 2 CH2OH), δ 3.72 (t, 2H, N+CH2CH 2 OH), δ 5.96, 6.22 (m, 2H, CH 2 =CH), δ 6.22 (m, 1H, CH2=CH).
13C−NMR (D2O 100MHz): δ 41.2 (N+ CH2CH2OH), δ 57.6 (N+CH2 CH2OH), δ 127.9 (CH2=CH), δ 133.1 (CH2=CH), δ 175.1 (COO-).
<実施例17>
1H−NMR (D2O 400MHz): δ 3.15 (t, 4H, N+CH 2 CH2OH), δ 3.79 (t, 4H, N+CH2CH 2 OH), δ 5.96, 6.22 (m, 2H, CH 2 =CH), δ 6.22 (m, 1H, CH2=CH).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.6 (N+CH2 CH2OH), δ 127.9 (CH2=CH), δ 133.1 (CH2=CH), δ 175.1 (COO-).
<実施例18>
1H−NMR (D2O 400MHz): δ 3.38 (t, 6H, N+CH 2 CH2OH), δ 3.88 (t, 6H, N+CH2CH 2 OH). δ 5.96, 6.22 (m, 2H, CH 2 =CH), δ 6.22 (m, 1H, CH2=CH).
13C−NMR (D2O 100MHz): δ 55.3 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 127.9 (CH2=CH), δ 133.1 (CH2=CH), δ 175.1 (COO-).
<実施例19>
1H−NMR (D2O 400MHz): δ 1.68 (t, 3H, CH 3 CH), δ 3.08 (t, 4H, N+CH 2 CH2OH), δ 3.73 (t, 4H, N+CH2CH 2 OH), δ 5.69 (m, 1H, CH=CHCOO-), δ 6.50 (m, 1H, CH=CHCOO-).
13C−NMR (D2O 100MHz): δ 16.9 (CH3CH), δ 48.9 (N+ CH2CH2OH), δ 56.7 (N+CH2 CH2OH), δ 127.4 (CH=CHCOO-), δ 141.1 (CH=CHCOO-), δ 175.9 (CHCOO-).
<実施例20>
1H−NMR (D2O 400MHz): δ 1.69 (m, 3H, CH 3 CH), δ 3.34 (t, 6H, N+CH 2 CH2OH), δ 3.84 (t, 6H, N+CH2CH 2 OH), δ 5.71 (m, 1H, N+ CH=CHCOO-), δ 6.50 (m, 1H, CH=CHCOO-).
13C−NMR (D2O 100MHz): δ 16.9 (CH3CH), δ 55.2 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 127.3 (CH=CHCOO-), δ 141.2 (CH=CHCOO-), δ 175.9 (CHCOO-).
<実施例21>
1H−NMR (D2O 400MHz): δ 0.89 (t, 3H, CH 3 CH2), δ 1.27 (m, 20H, CH3(CH 2 )6CH2, (CH 2 )4 CH2CH2COO-), δ 1.53 (m, 2H, CH 2 CH2COO-), δ 2.00 (m, 4H, CH 2 CH=CHCH 2 ), δ 2.14 (t, 2H, CH2CH 2 COO-), δ 2.99 (t, 2H, N+CH 2 CH2OH), δ 3.76 (t, 2H, N+CH2CH 2 OH), δ 5.32 (m, 2H, CH=CH).
13C−NMR (D2O 100MHz): δ 14.0 (CH3CH2), δ 22.6 (CH3 CH2), δ 26.4 (CH2CH2COO-), δ 27.2 (CH2CH=CHCH2), δ 29.3(CH3CH2CH2(CH2)4, (CH2)4CH2CH2COO-), δ 31.9 (CH3CH2 CH2), δ 37.8 (CH2CH2COO-), δ 41.9 (N+ CH2CH2OH), δ 58.6 (N+CH2 CH2OH), δ 129.7 (CH=CH), δ 181.7 (COO-).
<実施例22>
1H−NMR (D2O 400MHz): δ 0.88 (t, 3H, CH 3 CH2), δ 1.27(m, 20H, CH3(CH 2 )6CH2,(CH 2 )4CH2CH2COO-), δ 1.55 (m, 2H, CH 2 CH2COO-), δ 1.98 (m, 4H, CH 2 CH=CHCH 2 ), δ 2.16 (t, 2H, CH2CH 2 COO-), δ 3.05 (t, 4H, N+CH 2 CH2OH), δ 3.82 (t, 4H, N+CH2CH 2 OH), δ 5.32 (m, 2H, CH=CH).
13C−NMR (D2O 100MHz): δ 14.0 (CH3CH2), δ 22.6 (CH3 CH2), δ 26.3 (CH2CH2COO-), δ 27.1 (CH2CH=CHCH2), δ 29.2 (CH3CH2CH2(CH2)4, (CH2)4CH2CH2COO-), δ 31.8 (CH3CH2 CH2), δ 37.7 (CH2CH2COO-), δ 50.0 (N+ CH2CH2OH), δ 57.5 (N+CH2 CH2OH), δ 129.7 (CH=CH), δ 181.9 (COO-).
<実施例23>
1H−NMR (D2O 400MHz): δ 0.88 (t, 3H, CH 3 CH2), δ 1.27 (m, 20H, CH3(CH 2 )6CH2, (CH 2 )4 CH2CH2COO-), δ 1.56 (m, 2H, CH 2 CH2COO-), δ 1.96 (m, 4H, CH 2 CH=CHCH 2 ), δ 2.22 (t, 2H, CH2CH 2 COO-), δ 2.98 (t, 6H, N+CH 2 CH2OH), δ 3.76 (t, 6H, N+CH2CH 2 OH), δ 5.32 (m, 2H, CH=CH).
13C−NMR (D2O 100MHz): δ 14.1 (CH3CH2), δ 22.6 (CH3 CH2), δ 25.7 (CH2CH2COO-), δ 27.2 (CH2CHCHCH2), δ 29.2 (CH3CH2CH2(CH2)4, (CH2)4CH2CH2COO-), δ 31.8 (CH3CH2 CH2), δ 36.1 (CH2CH2COO-), δ 56.8 (N+ CH2CH2OH), δ 57.8 (N+CH2 CH2OH), δ 129.7 (CH=CH), δ 179.9(COO-).
<実施例24>
1H−NMR (D2O 400MHz): δ 0.89 (t, 3H, CH 3 CH2CH2), δ 1.25 (m, 14H, CH3(CH 2 )3CH2, (CH 2 )4CH2CH2COO-), δ 1.52 (s, 2H, CH 2 CH2COO-), δ 2.01 (m, 4H, CH2CH 2 CH), δ 2.14 (t, 2H, CH2CH 2 COO-), δ 2.76 (t, 2H, CHCH 2 CH), δ 2.99 (t, 2H, N+CH 2 CH2OH), δ 3.76 (t, 2H, N+CH2CH 2 OH). δ 5.29 (m, 4H, CH=CH).
13C−NMR (D2O 100MHz): δ 14.1 (CH3CH2CH2), δ 22.6 (CH3 CH2CH2), δ 25.6 (CHCH2CH), δ 26.3 (CH2CH2COO-), δ 27.3 (CH2 CH2CH), δ 29.3 (CH3CH2(CH2)2,(CH2)4CH2CH2COO-), δ 37.9 (CH2 CH2COO-), δ 42.0 (N+ CH2CH2OH), δ 58.9 (N+CH2 CH2OH), δ 127.9 (CH=CH), δ 181.8 (COO-).
<実施例25>
1H−NMR (D2O 400MHz): δ 0.91 (t, 3H, CH 3 CH2CH2), δ 1.27 (m, 14H, CH3(CH 2 )3CH2, (CH 2 )4CH2CH2COO-), δ 1.56 (s, 2H, CH 2 CH2COO-), δ 2.02 (m, 4H, CH2CH 2 CH), δ 2.19 (t, 2H, CH2CH 2 COO-), δ 2.77 (t, 2H, CHCH 2 CH), δ 3.06 (m, 4H, N+CH 2 CH2OH), δ 3.86 (m, 4H, N+CH2CH 2 OH), δ 5.31 (m, 4H, CH=CH).
13C−NMR (D2O 100MHz): δ 14.1 (CH3CH2CH2), δ 22.6 (CH3 CH2CH2), δ 25.6 (CHCH2CH), δ 26.3 (CH2CH2COO-), δ 27.2 (CH2 CH2CH), δ 29.3 (CH3CH2(CH2)2,(CH2)4CH2CH2COO-), δ 37.9 (CH2 CH2COO-), δ 50.3 (N+ CH2CH2OH), δ 57.7 (N+CH2 CH2OH), δ 127.9 (CH=CH), δ 181.8 (COO-).
<実施例26>
1H−NMR (D2O 400MHz): δ 0.89 (t, 3H, CH 3 CH2CH2), δ 1.25 (m, 14H, CH3(CH 2 )3CH2, (CH 2 )4CH2CH2COO-), δ 1.60 (s, 2H, CH 2 CH2COO-), δ 2.02 (m, 4H, CH2CH 2 CH), δ 2.29 (t, 2H, CH2CH 2 COO-), δ 2.75 (t, 2H, CHCH 2 CH), δ 2.85 (t, 6H, N+CH 2 CH2OH), δ 3.74 (t, 6H, N+CH2CH 2 OH), δ 5.31 (m, 4H, CH=CH).
13C−NMR (D2O 100MHz): δ 14.1 (CH3CH2CH2), δ 22.6 (CH3 CH2CH2), δ 25.6 (CHCH2CH), δ 26.3 (CH2CH2COO-), δ 27.3 (CH2 CH2CH), δ 29.3 (CH3CH2(CH2)2,(CH2)4CH2CH2COO-), δ 37.9 (CH2 CH2COO-), δ 57.3 (N+ CH2CH2OH), δ 58.5 (N+CH2 CH2OH), δ 127.9−130.2 (CH=CH), δ 181.8 (COO-).
<実施例27>
1H−NMR (D2O 400MHz): δ 1.13 (m, 6H, CHCH2(CH 2 )3), δ 1.55 (m, 4H, CHCH 2 ), δ 2.03 (m, 1H, CHCOO-), δ 3.19 (t, 4H, N+CH 2 CH2OH), δ 3.81 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 25.5 (CH2CH2CHCOO-), δ 25.7 (CH2CHCOO-), δ 29.9 (CH2CH2CH2CHCOO-), δ 47.1 (CHCOO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 186.8 (CHCOO-).
<実施例28>
1H−NMR (D2O 400MHz): δ 3.14 (t, 4H, N+CH 2 CH2OH), δ 3.78 (t, 4H, N+CH2CH 2 OH), δ 7.40−7.50 (m, 3H, CHCHCHCHCCOO-), δ 7.51−7.80 (m, 2H, CHCCOOH).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 128.3 (CHCHCHCCOO-), δ 128.8 (CHCHCCOO-), δ 131.2 (CCOO-), δ 136.3 (CHCHCHCCOO-), δ 175.7 (COO-).
<実施例29>
1H−NMR (D2O 400MHz): δ 3.05 (t, 2H, N+CH 2 CH2OH), δ 3.73 (t, 2H, N+CH2CH 2 OH), δ 3.85 (s, 2H, HOCH 2 COO-).
13C−NMR (D2O 100MHz): δ 41.2 (N+ CH2CH2OH), δ 57.6 (N+CH2 CH2OH), δ 61.2 (HOCH2COO-), δ 179.9 (HOCH2 COO-).
<実施例30>
1H−NMR (D2O 400MHz): δ 3.16 (t, 4H, N+CH 2 CH2OH), δ 3.81 (t, 4H, N+CH2CH 2 OH), δ 3.87 (s, 2H, HOCH 2 COO-).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.7 (N+CH2 CH2OH), δ 61.3 (HOCH2COO-), δ 179.9 (HOCH2 COO-).
<実施例31>
1H−NMR (D2O 400MHz): δ 3.43 (t, 6H, N+CH 2 CH2OH), δ 3.88 (s, 2H, HOCH 2 COO-), δ 3.90 (m, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 55.1 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 61.3 (HOCH2COO-), δ 179.8 (HOCH2 COO-).
<実施例32>
1H−NMR (D2O 400MHz): δ 1.24 (d, 3H, CH 3 CH), δ 3.01 (t, 2H, N+CH 2 CH2OH), δ 3.71 (t, 2H, N+CH2CH 2 OH), δ 4.00 (m, 1H, CH3CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH), δ 41.4 (N+ CH2CH2OH), δ 58.3 (N+CH2 CH2OH), δ 68.5 (CH3 CH(OH)COO-) , δ 182.5 (CH3CH(OH)COO-).
<実施例33>
1H−NMR (D2O 400MHz): δ 1.26 (d, 3H, CH 3 CH), δ 3.13 (t, 4H, N+CH 2 CH2OH), δ 3.79 (t, 4H, N+CH2CH 2 OH), δ 4.02 (m, 1H, CH3CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH), δ 49.0 (N+ CH2CH2OH), δ 56.9 (N+CH2 CH2OH), δ 68.5 (CH3 CH(OH)COO-) , δ 182.5 (CH3CH(OH)COO-).
<実施例34>
1H−NMR (D2O 400MHz): δ 1.25 (d, 3H, CH 3 CH), δ 3.32 (t, 6H, N+CH 2 CH2OH), δ 3.86 (t, 6H, N+CH2CH 2 OH), δ 4.01 (m, 1H, CH3CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 20.1 (CH3CH), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 68.5 (CH3 CH(OH)COO-) , δ 182.5 (CH3CH(OH)COO-).
<実施例35>
1H−NMR (D2O 400MHz): δ 2.53 (d, 3H, CH 3 ), δ 3.32 (t, 2H, N+CH 2 CH2OH), δ 3.86 (t, 2H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 25.5 (CH3), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 161.4 (COO-), δ 193.7 (CH3 C=O).
<実施例36>
1H−NMR (D2O 400MHz): δ 2.53 (d, 3H, CH 3 ), δ 3.32 (t, 4H, N+CH 2 CH2OH), δ 3.86 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 25.5 (CH3), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 161.4 (COO-), δ 193.7 (CH3 C=O).
<実施例37>
1H−NMR (D2O 400MHz): δ 2.53 (d, 3H, CH 3 ), δ 3.32 (t, 6H, N+CH 2 CH2OH), δ 3.86 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 25.5 (CH3), δ 55.4 (N+ CH2CH2OH), δ 55.6 (N+CH2 CH2OH), δ 161.4 (COO-), δ 193.7 (CH3 C=O).
<実施例38>
1H−NMR (D2O 400MHz): δ 3.04 (t, 2H, N+CH 2 CH2OH), δ 3.27 (s, 3H, CH 3 OCH2COO-), δ 3.71 (t, 2H, N+CH2CH 2 OH), δ 3.77 (s, 2H, CH3OCH 2 COO-).
13C−NMR (D2O 100MHz): δ 41.2 (N+ CH2CH2OH), δ 57.6 (CH3OCH2COO-), δ 58.1 (N+CH2 CH2OH), δ 71.2 (CH3OCH2COO-), δ 178.0 (CH3OCH2 COO-).
<実施例39>
1H−NMR (D2O 400MHz): δ 3.08 (t, 4H, N+CH 2 CH2OH), δ 3.20 (s, 3H, CH 3 OCH2COO-), δ 3.69 (m, 6H, CH3OCH 2 COO-,N+CH2CH 2 OH), δ 3.77 (s, 2H, CH3OCH 2 COO-).
13C−NMR (D2O 100MHz): δ 48.8 (N+ CH2CH2OH), δ 56.4 (N+CH2 CH2OH), δ 58.0 (CH3OCH2COO-), δ 71.1 (CH3OCH2COO-), δ 177.9 (CH3OCH2 COO-).
<実施例40>
1H−NMR (D2O 400MHz): δ 3.28 (t, 3H, CH 3 OCH2COO-), δ 3.39 (t, 6H, N+CH 2 CH2OH), δ 3.78 (s, 2H, CH3OCH 2 COO-), δ 3.87 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 55.1 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 58.1 (CH3OCH2COO-), δ 71.2 (CH3OCH2COO-), δ 178.0 (CH3OCH2 COO-).
<実施例41>
1H−NMR (D2O 400MHz): δ 3.15 (t, 4H, N+CH 2 CH2OH), δ 3.77 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 51.4 (N+ CH2CH2OH), δ 59.0 (N+CH2 CH2OH), δ 114.6 (CF3COO-), δ 165.1 (CF3 COO-).
<実施例42>
1H−NMR (D2O 400MHz): δ 3.41 (t, 6H, N+CH 2 CH2OH), δ 3.88 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 57.6 (N+ CH2CH2OH), δ 57.9 (N+CH2 CH2OH), δ 114.6 (CF3COO-), δ 165.0 (CF3 COO-).
<実施例43>
1H−NMR (D2O 400MHz): δ 3.13 (t, 4H, N+CH 2 CH2OH), δ 3.77 (t, 4H, N+CH2CH 2 OH), δ 6.85 (m, 2H, C(OH)CHCH, C(COO-)CHCHCH), δ 7.35 (m, 1H, CHCHC(OH)), δ 7.71 (m, 1H, C(COOH)CHCH).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 116.3 (C(OH)CHCH) , δ 118.0 (CHC(COO-)C(OH)) , δ 119.4 (C(COO-)CHCHCH) , δ 130.5 (C(COO-)CHCH) , δ 134.0 (CHCHC(OH)) , δ 159.6 (CC(OH)C), δ 175.5 (CCOO-).
<実施例44>
1H−NMR (D2O 400MHz): δ 3.35 (t, 6H, N+CH 2 CH2OH), δ 3.84 (t, 6H, N+CH2CH 2 OH), δ 6.85 (m, 2H, C(OH)CHCH, C(COO-)CHCHCH), δ 7.35 (m, 1H, CHCHC(OH)), δ 7.73 (m, 1H, C(COO-)CHCH).
13C−NMR (D2O 100MHz): δ 55.0 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 116.3 (C(OH)CHCH) , δ 118.1 (CHC(COO-)C(OH)) , δ 119.4 (C(COO-)CHCHCH) , δ 130.5 (C(COO-)CHCH) , δ 134.0 (CHCHC(OH)) , δ 159.7 (CC(OH)C), δ 175.4 (CCOO-).
<実施例45>
1H−NMR (D2O 400MHz): δ 3.15 (t, 4H, N+CH 2 CH2OH), δ 3.79 (t, 4H, N+CH2CH 2 OH), δ 6.83 (d, 2H, C(COO-)CHCH), δ 7.73 (d, 2H, C(OH)CHCH).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 114.9 (C(OH)CHCH) , δ 128.2 (C(COO-)) , δ 131.2 (C(COO-)CHCH) , δ 158.4 (C(OH)) , δ 175.3 (C(COO-)).
<実施例46>
1H−NMR (D2O 400MHz): δ 3.17 (t, 4H, N+CH 2 CH2OH), δ 3.80 (t, 4H, N+CH2CH 2 OH), δ 4.94 (s, 1H, CH(OH)(COO-)), δ 7.34 (m, 5H, (CH)5).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 75.0 (CH(OH)(COO-)) , δ 127.1 ((CH)2 CH(CH)2) , δ 128.2 (CHCHCCH(OH)(COO-)) , δ 128.8 (CHCCH(OH)(COO-)) , δ 140.6 (CCH(OH)(COO-)) , δ 179.4 (COO-).
<実施例47>
1H−NMR (D2O 400MHz): δ 3.42 (t, 6H, N+CH 2 CH2OH), δ 3.90 (t, 6H, N+CH2CH 2 OH), δ 4.96 (s, 1H, CH(OH)(COO-)), δ 7.35−7.40 (m, 5H, (CH)5).
13C−NMR (D2O 100MHz): δ 55.1 (N+ CH2CH2OH), δ 55.4 (N+CH2 CH2OH), δ 75.0 (CH(OH)(COO-)) , δ 127.1 ((CH)2 CH(CH)2) , δ 128.2 (CHCHCCH(OH)(COO-)) , δ 128.8 (CHCCH(OH)(COO-)) , δ 140.5 (CCH(OH)(COO-)) , δ 179.3 (COO-).
<実施例48>
1H−NMR (D2O 400MHz): δ 3.08 (t, 2H, N+CH 2 CH2OH), δ 3.60 (m, 2H, HOOCCH 2 COO-), δ 3.76 (t, 2H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 38.5 (HOOCCH2COO-), δ 41.3 (N+ CH2CH2OH), δ 57.6 (N+CH2 CH2OH), δ 174.6 (COOH, COO-).
<実施例49>
1H−NMR (D2O 400MHz): δ 3.21 (t, 4H, N+CH 2 CH2OH), δ 3.69 (s, 2H, HOOCCH 2 COO-), δ 3.83 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 52.6 (HOOCCH2COO-), δ 56.5 (N+CH2 CH2OH), δ 175.0 (COOH, COO-).
<実施例50>
1H−NMR (D2O 400MHz): δ 3.44 (t, 6H, N+CH 2 CH2OH), δ 3.69 (s, 2H, HOOCCH 2 COO-), δ 3.92 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 48.9 (HOOCCH2COO-), δ 55.1 (N+ CH2CH2OH), δ 55.4 (N+CH2 CH2OH), δ 174.9 (COOH, COO-).
<実施例51>
1H−NMR (D2O 400MHz): δ 2.51 (s, 4H, HOOCCH 2 CH 2 COO-), δ 3.22 (t, 4H, N+CH 2 CH2OH), δ 3.84 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 31.4 (HOOCCH2 CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 179.7 (COOH, COO-).
<実施例52>
1H−NMR (D2O 400MHz): δ 2.49 (s, 4H, HOOCCH 2 CH 2 COO-), δ 3.45 (t, 6H, N+CH 2 CH2OH), δ 3.93 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 31.5 (HOOCCH2 CH2COO-), δ 55.1 (N+ CH2CH2OH), δ 55.4 (N+CH2 CH2OH), δ 179.8 (COOH, COO-).
<実施例53>
1H−NMR (D2O 400MHz): δ 1.56 (t, 4H, HOOCCH2CH 2 CH 2 CH2COO-), δ 2.27 (t, 4H, HOOCCH 2 CH2CH2CH 2 COO-), δ 3.22 (t, 4H, N+CH 2 CH2OH), δ 3.84 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 24.8 (HOOCCH2 CH2 CH2CH2COO-), δ 35.5 (HOOCCH2CH2CH2 CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 181.3 (COOH, COO-).
<実施例54>
1H−NMR (D2O 400MHz): δ 2.55 (m, 2H, HOOCCH 2 CH(OH)COO-), δ 3.09 (t, 2H, N+CH 2 CH2OH), δ 3.76 (t, 2H, N+CH2CH 2 OH), δ 4.32 (m, 1H, HOOCCH2CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 40.2 (HOOCCH2CH(OH)COO-), δ 41.3 (N+ CH2CH2OH), δ 57.6 (N+CH2 CH2OH), δ 68.7 (HOOCCH2 CH(OH)COO-), δ 176.5 (CH2 COO-), δ 179.2 (C(OH)COO-).
<実施例55>
1H−NMR (D2O 400MHz): δ 2.52 (m, 2H, HOOCCH 2 CH(OH)COO-), δ 3.21 (t, 4H, N+CH 2 CH2OH), δ 3.83 (t, 4H, N+CH2CH 2 OH), δ 4.31 (m, 1H, HOOCCH2CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 40.5 (HOOCCH2CH(OH)COO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 68.9 (HOOCCH2 CH(OH)COO-), δ 176.9 (CH2 COO-), δ 179.5 (C(OH)COO-).
<実施例56>
1H−NMR (D2O 400MHz): δ 2.52 (m, 2H, HOOCCH 2 CH(OH)COO-), δ 3.41 (t, 6H, N+CH 2 CH2OH), δ 3.88 (t, 6H, N+CH2CH 2 OH), δ 4.29 (m, 1H, HOOCCH2CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 40.2 (HOOCCH2CH(OH)COO-), δ 55.0 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 68.7 (HOOCCH2 CH(OH)COO-), δ 176.5 (CH2 COO-), δ 179.2 (C(OH)COO-).
<実施例57>
1H−NMR (D2O 400MHz): δ 3.18 (t, 4H, N+CH 2 CH2OH), δ 3.80 (t, 4H, N+CH2CH 2 OH), δ 4.40 (s, 2H, HOOCCH(OH)CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 73.1 (HOOCCH(OH)CH(OH)COO-), δ 176.9 (COOH, COO-).
<実施例58>
1H−NMR (D2O 400MHz): δ 3.40 (t, 6H, N+CH 2 CH2OH), δ 3.87 (t, 6H, N+CH2CH 2 OH), δ 4.39 (s, 2H, HOOCCH(OH)CH(OH)COO-).
13C−NMR (D2O 100MHz): δ 55.0 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 73.0 (HOOCCH(OH)CH(OH)COO-), δ 176.7 (COOH, COO-).
<実施例59>
1H−NMR (D2O 400MHz): δ 2.65 (m, 4H, HOOCCH 2 C(OH)(COOH)CH 2 COO-), δ 3.16 (t, 4H, N+CH 2 CH2OH), δ 3.78 (t, 4H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 43.7 (HOOCCH2C(OH)(COOH)CH2COO-), δ 48.9 (N+ CH2CH2OH), δ 56.5 (N+CH2 CH2OH), δ 73.9 (HOOCCH2 C(OH)(COOH)CH2COO-), δ 174.8 (HOOCCH2C(OH)(COOH)CH2 COO-), δ 178.7 (HOOCCH2C(OH)(COOH)CH2COO-).
<実施例60>
1H−NMR (D2O 400MHz): δ 2.63 (m, 4H, HOOCCH 2 C(OH)(COO-)CH 2 COOH), δ 3.37 (t, 6H, N+CH 2 CH2OH), δ 3.84 (t, 6H, N+CH2CH 2 OH).
13C−NMR (D2O 100MHz): δ 43.7 (HOOCCH2C(OH)(COOH)CH2COO-), δ 55.0 (N+ CH2CH2OH), δ 55.3 (N+CH2 CH2OH), δ 73.8 (HOOCCH2 C(OH)(COOH)CH2COO-), δ 174.8 (HOOCCH2C(OH)(COOH)CH2 COO-), δ 178.7 (HOOCCH2C(OH)(COOH)CH2COO-).
<実施例61>
1H−NMR (D2O 400MHz): δ1.72−1.95 (m, 4H, CH 2 C(OH)(COO-)), δ3.29 (t, 6H, NH+(CH 2 CH2OH)3), δ3.41 (m, 1H, CH(OH)CH(OH)CH(OH)), δ3.81 (t, 6H, NH+(CH2CH 2 OH)3), δ3.86−4.02 (m, 2H, CH2CH(OH)CH(OH))
13C−NMR (D2O 100MHz): δ37.3 (CH2C(OH)(COO-)), δ40.6 (CH2C(OH)(COO-)), δ55.3 (NH+(CH2CH2OH)3), δ56.4 (NH+(CH2 CH2OH)3), δ67.0 (CH2 CH(OH)CH(OH)), δ70.4 (CH2 CH(OH)CH(OH)), δ75.2 (CH(OH)CH(OH)CH(OH)), δ76.9 (CH2 C(OH)(COO-)), δ181.3 (CH2C(OH)(COO-))
<比較例1〜28、39、40>
表1、8〜10に示す比較例1〜28、39、40の化合物を、実施例1と同様の合成方法と、表8〜10に記載した配合モル比にて合成した。
<比較例29>
表11に示した比較例29の化合物は和光純薬製の試薬を用いた。
<比較例30、31>
表11に示した比較例30、31化合物は特許文献4に記載の化合物を用いた。
<比較例32、33>
表12に示した比較例32、33の化合物は、ジメチルエタノールアミン又は水酸化コリンと、グリコール酸を用いて、実施例1と同様の合成方法で合成した。
<比較例34>
下記式で表される比較例34の化合物は、非特許文献(Chemical Communications, 2005, 4804−4806)に記載の方法に従って合成した(m.p.119℃)。
下記式で表される比較例35の化合物は、テトラブチルアンモニウムブロマイド水溶液を、アニオン交換樹脂を充填したカラムを通過させ、得られた水溶液に乳酸を加え、攪拌後、溶媒を減圧留去し、洗浄することで合成した(m.p.110℃)。
下記式で表される比較例36の化合物は、特許文献4に記載の方法に従って合成した。
下記式で表される比較例37の化合物は、トリエタノールアミンと臭化水素酸を、実施例1と同様の合成方法で合成した。
下記式で表される比較例38の化合物は、テトラブチルアンモニウムブロマイド水溶液を、アニオン交換樹脂を充填したカラムを通過させ、得られた水溶液に酒石酸を加え、攪拌後、溶媒を減圧留去し、洗浄することで合成した。
表14、表17に示した比較例49の化合物は、トリエタノールアミンとレブリン酸を用いて、実施例1と同様の合成方法で合成した(m.p.30℃)。
1.室温(25℃)での性状
実施例1〜61及び比較例1〜28、39、40の化合物について、スクリュー管に添加し減圧乾燥させ無水物として、室温(25℃)での液性を確認した。また、スクリュー管を傾けて、イオン液体の流動性を観察した。また、−5℃に設定した低温恒温器に、イオン液体を24時間放置し、次いで−10℃で24時間放置し、性状(液体、固形)を確認した。結果を表1〜10に示す。なお表1中の"liquid"は室温(25℃)で液体であることを示し、"solid"は室温(25℃)で固体であることを示し、表2〜7中に融点(mp(℃))を、−10℃未満(<−10)、−10℃以上−5℃未満(−10≦〜<−5で示す。表8〜10に示した比較例の化合物の融点は、試料を減圧乾燥させ無水物とした後に、示差走査熱量分析装置(DSC)で測定したピークトップ温度を融点とした。
2.水への溶解度
実施例1〜61、比較例29〜31の化合物について、水への溶解度を測定した。水への溶解度は次の方法で測定した。TG/DTAで測定した含水率を踏まえて、スクリュー管に所定の濃度となるようにイオン液体及び水を仕込み、その後、25℃で30分間攪拌した後、10分間静置し、溶解性を目視で確認し、25℃での水100gに溶解するイオン液体量(g)を溶解度(g/100g water)とした。その結果を表2〜表7及び表11に示す。
3.熱分解温度
示差熱熱重量同時測定装置(TG/DTA)で、実施例の化合物1〜61及び比較例28の化合物の熱分解温度を測定した。その結果を表1〜表7、10に示す。熱分解温度は、化合物に含まれる水分を除いた5%重量減少温度を示した。
表12に示す各実施例、比較例32、33の化合物について、生分解性試験を行った。生分解性試験は、OECDテストガイドライン301C法に準拠して行った。この試験には一般活性汚泥を微生物源として使用し、調製した標準試験培養液300mlに、微生物源30mg/l、被験物質100mg/lの濃度になるようにそれぞれ投入し、25±1℃、試験期間28日、標準物質にアニリンを使用して行った。アクタック製BODセンサーを使用して生化学的酸素要求量(BOD;biochemical oxygen demand)を測定し、算出した理論的酸素要求量の値から分解度(分解率)を算出した。結果を表12に示す。
[タンパク質(シトクロムC)溶解濃度]
表13と表14に示す各実施例、比較例34〜37および比較例49(室温(25℃)で固体、融点30℃)の化合物について、タンパク質溶解濃度を測定した。表13、14に示す実施例化合物に室温(25℃)でタンパク質(シトクロムC Horse Heart 分子量12384)を所定濃度添加し、混合後、タンパク質の溶解を目視にて判別した。各実施例におけるタンパク質の溶解試験は、イオン液体中の水分量を約7〜12%として行った。なお、比較例34、35、49の化合物は、室温では固体であったため、非特許文献(Chemical Communications, 2005, 4804−4806)のシトクロムCの溶解試験方法を参考に、シトクロムCに対して良溶媒である水で溶解して85%水溶液で評価した(表13、14タンパク(シトクロムC)溶解濃度(1))。実施例34、40、61及び比較例34〜37、比較例49については、水分率を一定にして(14%±0.5%)、同様にタンパク質の溶解性を再測定した。水分量はカールフィッシャー法により測定した(表13、14タンパク(シトクロムC)溶解濃度(2))。溶液が透明均一である完全溶解の状態を○、シトクロムCの残存が目視で確認できる状態を×と評価し、結果を表13と表14に示す。
[長期安定性]
実施例34、40、61、及び比較例34の化合物について、イオン液体中の水分率を一定(14%±0.5%)にした試料にシトクロムCを溶解して、次の方法でタンパク質のイオン液体中での構造変化(変性)を確認した。なお比較例41として、一般的なタンパク質の溶解溶媒であるpH=7.4の50mMリン酸バッファー(50mMリン酸2水素カリウム及び50mMリン酸水素2カリウムで調製)もタンパク質を溶解した直後の試料を用いて同様に確認を行った。
ランダムコイルに変性していた。次に、リン酸バッファー中のシトクロムC(比較例41)は変性せず(アミドI領域:1653cm-1、アミドII領域:1547cm-1)、α-へリックス構造であることを確認し、実施例34、40、61のイオン液体中のシトクロムCが、リン酸バッファーと同等の測定結果で(アミドI領域:1653-1655cm-1、アミドII領域:1545-1549cm-1)、いずれも、変性した構造ではなく、α-ヘリックス構造を維持していることを確認した。つまり、実施例34、40、61のイオン液体は、高濃度条件下でも、リフォールティングの効果を発現してシトクロムCを変性することなく溶解していることを示した。
タンパク質として、前記のシトクロムC(アルカリ性)に加えて、ヘモグロビン(中性)、アルブミン(酸性)に対するイオン液体の溶解性を確認した。実施例34、40、61、及び比較例34、35、37の化合物について、水分率を一定(14%±0.5%)にした試料にヘモグロビン、アルブミンを所定濃度溶解して、前記のシトクロムCと同様の方法でタンパク質溶解濃度を測定した。結果を表15と表16に示す。
[DNAの抽出方法]
中性洗剤(陰イオン界面活性剤)(1.5g)を水(200g)で溶解させ、鶏レバー(47g)と共にミキサーで2分間混合した。そこへ2mol/l のNaOH水溶液(250ml)を加え軽く撹拌し、100℃で5分間加熱した。加熱後、常温に戻し、遠心分離(3000rpm、15分)を行って、ろ液を回収した。
[DNA溶解濃度]
表17に示す実施例32〜34、40、58、60、及び比較例34、35、37、49の化合物について、DNA溶解濃度を測定した。各実施例のイオン液体は、カールフィッシャー法により水分量を測定し、水分量が14%±0.5%になるように調製した。なお、比較例35、49の化合物は、室温で固体であったため、非特許文献(ChemicalCommunications, 2005, 4804−4806)のシトクロムCの溶解試験方法を参考に、DNAの良溶媒である水で14%±0.5%になるように溶解して評価した。これらの化合物に、上記の方法で抽出したDNAを室温(25℃)で所定濃度添加し、混合後、DNAの溶解を目視にて判別した。溶液が透明均一である完全溶解の状態を○、DNAの残存が目視で確認できるの状態を×と評価した。結果を表17に示す。
表18に示す実施例34、58、比較例38の化合物について、各化合物0.5gにメチルエチルケトンを0.5g加え、マグネチックスターラーで10分間混合し、溶解状態を目視にて確認した。その結果を表18に示す。
表19〜表21に示す各実施例、比較例38の化合物について、各化合物0.5gと酸化ジルコニウム(IV)(和光純薬工業(株)、試薬特級、約5〜30μm)0.5gを自転公転ミキサーで2000rpm、1min×5回混合した後の分散状態を目視で確認した。酸化ジルコニウムが分散し、良好に分散した状態を○、分散せず沈降している状態を×で評価した。結果を表19〜表21に示す。
表22に示す実施例29〜34、40、47、60と比較例29、34〜37、42〜48の化合物について、比熱容量測定を行った。比熱容量測定試験はJIS K 7123に従って測定した。
Claims (16)
- カチオン及びアニオンを含む親水性室温イオン液体であって、該カチオンが下記式(I)の第4級アンモニウムカチオンで、該アニオンがカルボン酸アニオンであることを特徴とする親水性室温イオン液体。
- カルボン酸アニオンが、炭素数1〜20の飽和脂肪族モノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、炭素数3〜20の不飽和脂肪族モノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、炭素数6〜14の飽和脂環式モノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、炭素数6〜14の芳香族モノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、1〜2個の水酸基を含有する炭素数2〜10の飽和ヒドロキシモノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、1〜2個のエーテル基を含有する炭素数2〜20のアルキルエーテルカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、1〜2個のカルボニル基を含有する炭素数3〜10の飽和カルボニルモノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、1〜2個の水酸基を含有する炭素数6〜14のヒドロキシ芳香族モノカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、炭素数2〜10の飽和ジカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- カルボン酸アニオンが、1〜2個の水酸基を含有する炭素数4〜10の飽和ヒドロキシジ又はトリカルボン酸アニオンである請求項1に記載の親水性室温イオン液体。
- 請求項1から11のいずれかに記載の親水性室温イオン液体を含む、水素結合性材料に対する溶解又は分散用溶媒。
- 請求項1から11のいずれかに記載の親水性室温イオン液体を含む、タンパク質溶解溶媒。
- 請求項1から11のいずれかに記載の親水性室温イオン液体を含む、核酸溶解溶媒。
- 請求項1から11のいずれかに記載の親水性室温イオン液体を含む、タンパク質リフォールディング剤。
- 請求項1から11のいずれかに記載の親水性室温イオン液体を含む、熱媒体。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013205317A JP6559394B2 (ja) | 2012-12-05 | 2013-09-30 | 親水性室温イオン液体とその用途 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012266147 | 2012-12-05 | ||
JP2012266147 | 2012-12-05 | ||
JP2013205317A JP6559394B2 (ja) | 2012-12-05 | 2013-09-30 | 親水性室温イオン液体とその用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014131975A true JP2014131975A (ja) | 2014-07-17 |
JP6559394B2 JP6559394B2 (ja) | 2019-08-14 |
Family
ID=51411248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013205317A Active JP6559394B2 (ja) | 2012-12-05 | 2013-09-30 | 親水性室温イオン液体とその用途 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6559394B2 (ja) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015156398A1 (ja) * | 2014-04-10 | 2015-10-15 | ミヨシ油脂株式会社 | イオン液体を用いた生体触媒用溶媒、及びその溶媒と生体触媒を含む生体触媒溶液 |
JP2016077935A (ja) * | 2014-10-10 | 2016-05-16 | 国立研究開発法人産業技術総合研究所 | 酸性ガス吸収液及び酸性ガス分離回収方法 |
JP2016083623A (ja) * | 2014-10-27 | 2016-05-19 | 国立研究開発法人産業技術総合研究所 | 酸性ガス吸収液及び酸性ガス分離回収方法 |
JP2017502750A (ja) * | 2014-03-24 | 2017-01-26 | 金仕生物科技(常熟)有限公司 | 無細胞コラーゲン組織及び無細胞コラーゲン組織を含む人工弁膜の処理方法 |
WO2017141775A1 (ja) * | 2016-02-15 | 2017-08-24 | デクセリアルズ株式会社 | イオン液体、潤滑剤及び磁気記録媒体 |
JP2017179319A (ja) * | 2016-02-15 | 2017-10-05 | デクセリアルズ株式会社 | イオン液体、潤滑剤及び磁気記録媒体 |
JP2018513255A (ja) * | 2015-04-22 | 2018-05-24 | エス.シー. ジョンソン アンド サン、インコーポレイテッド | イオン液体の洗浄剤組成物 |
CN110105229A (zh) * | 2019-06-05 | 2019-08-09 | 中国科学院兰州化学物理研究所 | 一种离子液体及其制备方法和作为水基润滑添加剂的应用 |
WO2020166674A1 (ja) | 2019-02-13 | 2020-08-20 | ミヨシ油脂株式会社 | 有機アンモニウム塩を含む組成物 |
WO2020166678A1 (ja) | 2019-02-13 | 2020-08-20 | ミヨシ油脂株式会社 | 化粧料配合剤および化粧料並びにその製造方法 |
WO2021095398A1 (ja) | 2019-11-14 | 2021-05-20 | ミヨシ油脂株式会社 | 有機アンモニウム塩とそれを用いた水素結合性材料処理剤 |
WO2021256448A1 (ja) | 2020-06-16 | 2021-12-23 | ミヨシ油脂株式会社 | 潤滑性を付与する添加剤又は組成物 |
WO2022074740A1 (ja) | 2020-10-06 | 2022-04-14 | エンバイロ・ビジョン株式会社 | 廃水処理装置及び廃水処理方法 |
WO2022225046A1 (ja) * | 2021-04-23 | 2022-10-27 | ミヨシ油脂株式会社 | ゲルの形成又は増粘特性に適した組成物 |
WO2022225048A1 (ja) | 2021-04-23 | 2022-10-27 | ミヨシ油脂株式会社 | アミノ酸とカルボン酸を用いた配合物、有機塩並びにそれらを含む組成物とその用途 |
CN116199880A (zh) * | 2023-03-16 | 2023-06-02 | 烟台先进材料与绿色制造山东省实验室 | 一种氨基酸基离子液体及其制备方法和应用、水基润滑剂 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030209689A1 (en) * | 2002-05-08 | 2003-11-13 | Clearwater, Inc. | Heat exchange fluids |
JP2005515168A (ja) * | 2001-09-17 | 2005-05-26 | ソルベント イノベーション ゲーエムベーハー | イオン液体 |
JP2007515372A (ja) * | 2003-12-23 | 2007-06-14 | ビーエーエスエフ アクチェンゲゼルシャフト | 塩化水素を気相酸化することによる塩素の製造方法 |
JP2007532525A (ja) * | 2004-04-07 | 2007-11-15 | ザ ユニバーシティ オブ ヨーク | 液体 |
JP2008127410A (ja) * | 2006-11-17 | 2008-06-05 | Kb Seiren Ltd | ポリエステル樹脂の製造方法 |
JP2008184402A (ja) * | 2007-01-29 | 2008-08-14 | Medorekkusu:Kk | 外用剤用の低刺激性溶解助剤 |
WO2010040191A2 (en) * | 2008-04-24 | 2010-04-15 | The Academician Y.H. Mamedaliyev Institute Of Petrochemical Processes | Method of selective purification of alkyl-tert-alkyl ethers by ionic liquid |
WO2010109544A1 (ja) * | 2009-03-27 | 2010-09-30 | 株式会社メドレックス | 核酸を有効成分とする外用剤組成物 |
WO2011089322A1 (en) * | 2010-01-25 | 2011-07-28 | Oy Granula Ab Ltd | The use of a composition with low corrosive properties |
-
2013
- 2013-09-30 JP JP2013205317A patent/JP6559394B2/ja active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005515168A (ja) * | 2001-09-17 | 2005-05-26 | ソルベント イノベーション ゲーエムベーハー | イオン液体 |
US20030209689A1 (en) * | 2002-05-08 | 2003-11-13 | Clearwater, Inc. | Heat exchange fluids |
JP2007515372A (ja) * | 2003-12-23 | 2007-06-14 | ビーエーエスエフ アクチェンゲゼルシャフト | 塩化水素を気相酸化することによる塩素の製造方法 |
JP2007532525A (ja) * | 2004-04-07 | 2007-11-15 | ザ ユニバーシティ オブ ヨーク | 液体 |
JP2008127410A (ja) * | 2006-11-17 | 2008-06-05 | Kb Seiren Ltd | ポリエステル樹脂の製造方法 |
JP2008184402A (ja) * | 2007-01-29 | 2008-08-14 | Medorekkusu:Kk | 外用剤用の低刺激性溶解助剤 |
WO2010040191A2 (en) * | 2008-04-24 | 2010-04-15 | The Academician Y.H. Mamedaliyev Institute Of Petrochemical Processes | Method of selective purification of alkyl-tert-alkyl ethers by ionic liquid |
WO2010109544A1 (ja) * | 2009-03-27 | 2010-09-30 | 株式会社メドレックス | 核酸を有効成分とする外用剤組成物 |
WO2011089322A1 (en) * | 2010-01-25 | 2011-07-28 | Oy Granula Ab Ltd | The use of a composition with low corrosive properties |
Non-Patent Citations (6)
Title |
---|
ABDEL HADI, AHMED M.; ALI HAMMAM, OLFAT; NOH, ALAA: "Histopathological changes and DNA pattern in esophageal and gastric mucosa before and after treatmen", AUSTRALIAN JOURNAL OF BASIC AND APPLIED SCIENCES, vol. 2(3), JPN6017010211, 2008, pages 658 - 671, ISSN: 0003523944 * |
BICAK,NIYAZI, JOURNAL OF MOLECULAR LIQUIDS, vol. V116 N1, JPN5007005061, 2005, pages 15 - 18, ISSN: 0003523942 * |
CHEMICAL ENGINEERING JOURNAL, vol. 162, JPN6018012677, 2010, pages 802 - 808, ISSN: 0003773984 * |
FLUID PHASE EQUILIBRIA, vol. 299, JPN6018012674, 2010, pages 42 - 50, ISSN: 0003773982 * |
HEKMAT, DARIUSCH: "Advanced protein crystallization using water-soluble ionic liquids as crystallization additives", BIOTECHNOLOGY LETTERS, vol. 29(11), JPN6017010208, 2007, pages 1703 - 1711, ISSN: 0003523943 * |
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, vol. 49, JPN6018012676, 2010, pages 11809 - 11813, ISSN: 0003773983 * |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017502750A (ja) * | 2014-03-24 | 2017-01-26 | 金仕生物科技(常熟)有限公司 | 無細胞コラーゲン組織及び無細胞コラーゲン組織を含む人工弁膜の処理方法 |
WO2015156398A1 (ja) * | 2014-04-10 | 2015-10-15 | ミヨシ油脂株式会社 | イオン液体を用いた生体触媒用溶媒、及びその溶媒と生体触媒を含む生体触媒溶液 |
US10240141B2 (en) | 2014-04-10 | 2019-03-26 | Miyoshi Oil & Fat Co., Ltd. | Biocatalyst solvent using ionic liquid, and biocatalyst solution containing biocatalyst and said solvent |
JP2016077935A (ja) * | 2014-10-10 | 2016-05-16 | 国立研究開発法人産業技術総合研究所 | 酸性ガス吸収液及び酸性ガス分離回収方法 |
JP2016083623A (ja) * | 2014-10-27 | 2016-05-19 | 国立研究開発法人産業技術総合研究所 | 酸性ガス吸収液及び酸性ガス分離回収方法 |
JP2018513255A (ja) * | 2015-04-22 | 2018-05-24 | エス.シー. ジョンソン アンド サン、インコーポレイテッド | イオン液体の洗浄剤組成物 |
WO2017141775A1 (ja) * | 2016-02-15 | 2017-08-24 | デクセリアルズ株式会社 | イオン液体、潤滑剤及び磁気記録媒体 |
JP2017179319A (ja) * | 2016-02-15 | 2017-10-05 | デクセリアルズ株式会社 | イオン液体、潤滑剤及び磁気記録媒体 |
CN113423470A (zh) * | 2019-02-13 | 2021-09-21 | 三吉油脂株式会社 | 化妆品配合剂、化妆品及其制造方法 |
WO2020166678A1 (ja) | 2019-02-13 | 2020-08-20 | ミヨシ油脂株式会社 | 化粧料配合剤および化粧料並びにその製造方法 |
KR20210126551A (ko) | 2019-02-13 | 2021-10-20 | 미요시 유시 가부시끼가이샤 | 화장료 배합제 및 화장료, 및 그 제조 방법 |
JPWO2020166674A1 (ja) * | 2019-02-13 | 2021-12-09 | ミヨシ油脂株式会社 | 有機アンモニウム塩を含む組成物 |
JPWO2020166678A1 (ja) * | 2019-02-13 | 2021-12-16 | ミヨシ油脂株式会社 | 化粧料配合剤および化粧料並びにその製造方法 |
WO2020166674A1 (ja) | 2019-02-13 | 2020-08-20 | ミヨシ油脂株式会社 | 有機アンモニウム塩を含む組成物 |
JP7490581B2 (ja) | 2019-02-13 | 2024-05-27 | ミヨシ油脂株式会社 | 化粧料配合剤および化粧料並びにその製造方法 |
JP7490580B2 (ja) | 2019-02-13 | 2024-05-27 | ミヨシ油脂株式会社 | 有機アンモニウム塩を含む組成物 |
CN110105229A (zh) * | 2019-06-05 | 2019-08-09 | 中国科学院兰州化学物理研究所 | 一种离子液体及其制备方法和作为水基润滑添加剂的应用 |
WO2021095398A1 (ja) | 2019-11-14 | 2021-05-20 | ミヨシ油脂株式会社 | 有機アンモニウム塩とそれを用いた水素結合性材料処理剤 |
KR20230023628A (ko) | 2020-06-16 | 2023-02-17 | 미요시 유시 가부시끼가이샤 | 윤활성을 부여하는 첨가제 또는 조성물 |
WO2021256448A1 (ja) | 2020-06-16 | 2021-12-23 | ミヨシ油脂株式会社 | 潤滑性を付与する添加剤又は組成物 |
WO2022074740A1 (ja) | 2020-10-06 | 2022-04-14 | エンバイロ・ビジョン株式会社 | 廃水処理装置及び廃水処理方法 |
KR20230174751A (ko) | 2021-04-23 | 2023-12-28 | 미요시 유시 가부시끼가이샤 | 아미노산과 카르복실산을 사용한 배합물, 유기염 및 이들을 포함하는 조성물과 그 용도 |
WO2022225048A1 (ja) | 2021-04-23 | 2022-10-27 | ミヨシ油脂株式会社 | アミノ酸とカルボン酸を用いた配合物、有機塩並びにそれらを含む組成物とその用途 |
WO2022225046A1 (ja) * | 2021-04-23 | 2022-10-27 | ミヨシ油脂株式会社 | ゲルの形成又は増粘特性に適した組成物 |
CN116199880A (zh) * | 2023-03-16 | 2023-06-02 | 烟台先进材料与绿色制造山东省实验室 | 一种氨基酸基离子液体及其制备方法和应用、水基润滑剂 |
Also Published As
Publication number | Publication date |
---|---|
JP6559394B2 (ja) | 2019-08-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6559394B2 (ja) | 親水性室温イオン液体とその用途 | |
JP6378475B2 (ja) | 親水性室温イオン液体とその用途 | |
Takahashi et al. | AJIPHASE®: a highly efficient synthetic method for one‐pot peptide elongation in the solution phase by an Fmoc strategy | |
Li et al. | Design of environmentally friendly ionic liquid aqueous two-phase systems for the efficient and high activity extraction of proteins | |
US10207983B2 (en) | Amino and imino propionic acids, process of preparation and use | |
Soltanmohammadi et al. | New aspects of deep eutectic solvents: extraction, pharmaceutical applications, as catalyst and gas capture | |
Miao et al. | Amphiphilic nanostructure in choline carboxylate and amino acid ionic liquids and solutions | |
JP5887065B2 (ja) | 親水性イオン液体 | |
EP3732274B1 (en) | Composition useful as friction modifier | |
Carreira et al. | Amino-acid-based chiral ionic liquids characterization and application in aqueous biphasic systems | |
Vieira et al. | Fluorinated Ionic Liquids as Task-Specific Materials: An Overview of Current Research | |
CN109554203A (zh) | 一种抗乳化低硫柴油抗磨剂的制备方法 | |
He et al. | Krafft Temperature, Critical Micelle Concentration, and Rheology of “Pseudo‐Gemini” Surfactant Comprising Fatty Acid Soap and Bola‐Type Quaternary Ammonium Salt | |
CN102803453B (zh) | 液体脂肪胺羧酸盐组合物 | |
WO2021095398A1 (ja) | 有機アンモニウム塩とそれを用いた水素結合性材料処理剤 | |
RU2147627C1 (ru) | Состав ингибитора коррозии | |
MX2013002300A (es) | Disolvente de pintura de microemulsion. | |
JP7525254B2 (ja) | 有機アンモニウム塩とそれを用いた生体試料処理剤 | |
Pereira et al. | On the hunt for more benign and biocompatible ABS | |
JP5995306B2 (ja) | 低分子ゲル化剤及び該ゲル化剤を用いたヒドロゲル | |
Krasteva et al. | Mixed Stearoyl-r ac-glycerol/12-(Hydroxy) stearoyl-r ac-glycerol Monolayers on the Air/Water Interface: Brewster Angle Microscopy and Grazing Incidence X-ray Diffraction Investigation | |
US7314951B2 (en) | Process and composition for lower toxicity quaternary ammonium compounds | |
US10093883B2 (en) | Glucose gemini surfactant compound and method for preparation thereof | |
US3151123A (en) | Acid-soluble chlorophyllins and their production | |
Kundu et al. | Recent Advances in Bioionic Liquids and Biocompatible Ionic Liquid‐Based Microemulsions |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160620 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170223 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170328 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20170515 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170727 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20171212 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180309 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20180320 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180410 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180518 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20180601 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181227 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190717 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6559394 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |