KR100585219B1 - Derivatives of Phosphate and the method for the preparation thereof - Google Patents
Derivatives of Phosphate and the method for the preparation thereof Download PDFInfo
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- KR100585219B1 KR100585219B1 KR1020040032231A KR20040032231A KR100585219B1 KR 100585219 B1 KR100585219 B1 KR 100585219B1 KR 1020040032231 A KR1020040032231 A KR 1020040032231A KR 20040032231 A KR20040032231 A KR 20040032231A KR 100585219 B1 KR100585219 B1 KR 100585219B1
- Authority
- KR
- South Korea
- Prior art keywords
- phosphate
- ethylene glycol
- hexadecanol
- mmol
- hexanediol
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 7
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 60
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 19
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000001177 diphosphate Substances 0.000 claims abstract description 7
- 235000011180 diphosphates Nutrition 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 235000021317 phosphate Nutrition 0.000 claims abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 256
- 239000010452 phosphate Substances 0.000 claims description 59
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 36
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 36
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 30
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 30
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000004973 liquid crystal related substance Substances 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 11
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 10
- -1 phosphate compound Chemical class 0.000 claims description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 8
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 claims description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 3
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 3
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 239000005792 Geraniol Substances 0.000 claims description 3
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- 235000012000 cholesterol Nutrition 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229940043259 farnesol Drugs 0.000 claims description 3
- 229930002886 farnesol Natural products 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 229940113087 geraniol Drugs 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 3
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004386 Erythritol Substances 0.000 claims description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
- INDXRDWMTVLQID-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO.OCCCCO INDXRDWMTVLQID-UHFFFAOYSA-N 0.000 claims description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- 229940009714 erythritol Drugs 0.000 claims description 2
- JEIPRNJORASSFQ-UHFFFAOYSA-N heptane-1,7-diol Chemical compound C(CCCCCCO)O.C(CCCCCCO)O JEIPRNJORASSFQ-UHFFFAOYSA-N 0.000 claims description 2
- HJJLDNAELNDBBL-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO.OCCCCCCO HJJLDNAELNDBBL-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- YSPXNJODCGZWPD-UHFFFAOYSA-N pentane-1,5-diol Chemical compound OCCCCCO.OCCCCCO YSPXNJODCGZWPD-UHFFFAOYSA-N 0.000 claims description 2
- YRVCHYUHISNKSG-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO.OCCCO YRVCHYUHISNKSG-UHFFFAOYSA-N 0.000 claims description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 claims 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 abstract description 8
- 150000003904 phospholipids Chemical class 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 235000019441 ethanol Nutrition 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 19
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 15
- 210000003491 skin Anatomy 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 210000000434 stratum corneum Anatomy 0.000 description 6
- 238000011084 recovery Methods 0.000 description 5
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010016807 Fluid retention Diseases 0.000 description 3
- 239000004909 Moisturizer Substances 0.000 description 3
- FSXFTQSEBVHREX-UHFFFAOYSA-N P(=O)(O)(O)OCCCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O Chemical compound P(=O)(O)(O)OCCCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O FSXFTQSEBVHREX-UHFFFAOYSA-N 0.000 description 3
- JCABFEJJYFYUDU-UHFFFAOYSA-N P(=O)(O)(O)OCCCCCCCCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O Chemical compound P(=O)(O)(O)OCCCCCCCCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O JCABFEJJYFYUDU-UHFFFAOYSA-N 0.000 description 3
- CVKCPUVQQCWSLK-UHFFFAOYSA-N P(=O)(O)(O)OCCO.C(CCC)(O)O.C(CCCCCCCCCCCCCCC)O Chemical compound P(=O)(O)(O)OCCO.C(CCC)(O)O.C(CCCCCCCCCCCCCCC)O CVKCPUVQQCWSLK-UHFFFAOYSA-N 0.000 description 3
- FCQJYQUHPPDQET-UHFFFAOYSA-N P(=O)(O)(O)OCCO.C(CCCCC)(O)O.C(C)C(CO)CCCC Chemical compound P(=O)(O)(O)OCCO.C(CCCCC)(O)O.C(C)C(CO)CCCC FCQJYQUHPPDQET-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MEKRMIBBBALEIX-UHFFFAOYSA-N butane-1,1-diol hexadecan-1-ol hexadecyl dihydrogen phosphate Chemical compound P(=O)(O)(O)OCCCCCCCCCCCCCCCC.C(CCC)(O)O.C(CCCCCCCCCCCCCCC)O MEKRMIBBBALEIX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BDQCFCGJMRINET-UHFFFAOYSA-N hexadecan-1-ol hexadecyl dihydrogen phosphate hexane-1,1-diol Chemical compound P(=O)(O)(O)OCCCCCCCCCCCCCCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O BDQCFCGJMRINET-UHFFFAOYSA-N 0.000 description 3
- VTDOZRZLLLAVJF-UHFFFAOYSA-N hexane-1,1-diol pentan-1-ol propyl dihydrogen phosphate Chemical compound P(=O)(O)(O)OCCC.C(CCCCC)(O)O.C(CCCC)O VTDOZRZLLLAVJF-UHFFFAOYSA-N 0.000 description 3
- 230000001333 moisturizer Effects 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000008591 skin barrier function Effects 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 2
- YFFDOPNXIFQZRC-UHFFFAOYSA-N P(=O)(O)(O)OCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O Chemical compound P(=O)(O)(O)OCCC.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O YFFDOPNXIFQZRC-UHFFFAOYSA-N 0.000 description 2
- PPYJPLYICCFQLJ-UHFFFAOYSA-N P(=O)(O)(O)OCCO.C(CCCCC)(O)O.C(CCCC)O Chemical compound P(=O)(O)(O)OCCO.C(CCCCC)(O)O.C(CCCC)O PPYJPLYICCFQLJ-UHFFFAOYSA-N 0.000 description 2
- JPDOWDFSCQDSKZ-UHFFFAOYSA-N P(=O)(O)(O)OCCO.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O Chemical compound P(=O)(O)(O)OCCO.C(CCCCC)(O)O.C(CCCCCCCCCCCCCCC)O JPDOWDFSCQDSKZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229940106189 ceramide Drugs 0.000 description 2
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000036572 transepidermal water loss Effects 0.000 description 2
- COKRBWXOLNTYOR-UHFFFAOYSA-N C(CCCCCCCO)O.C(CCCCCCCO)O Chemical compound C(CCCCCCCO)O.C(CCCCCCCO)O COKRBWXOLNTYOR-UHFFFAOYSA-N 0.000 description 1
- NTZVBWGCZVFPRT-UHFFFAOYSA-N OCCCCCCCCCO.OCCCCCCCCCO Chemical compound OCCCCCCCCCO.OCCCCCCCCCO NTZVBWGCZVFPRT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- GCSHATLPTFNXOS-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO.OCCCCCCCCCCO GCSHATLPTFNXOS-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- SFFVATKALSIZGN-UHFFFAOYSA-N hexadecan-7-ol Chemical compound CCCCCCCCCC(O)CCCCCC SFFVATKALSIZGN-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 230000036620 skin dryness Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Cosmetics (AREA)
Abstract
본 발명은 인체의 인지질과 유사한 포스페이트(Phosphate) 구조를 가짐으로써 피부 친화적이고 건조환경에서 우수한 수분 유지 능력을 가지며, 하기 화학식 1로 표시되는 포스페이트 유도체 및 이의 제조방법에 관한 것이다:The present invention relates to a phosphate derivative represented by the following Chemical Formula 1 and a method for preparing the same, having a phosphate structure similar to the phospholipid of the human body and having skin-friendly and excellent moisture retention ability in a dry environment.
[화학식 1][Formula 1]
상기 식 중에서, R은 서로 같거나 다른 수소 또는 히드록시기를 포함하거나 포함하지 않는 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이며;Wherein R is an alkyl group comprising a saturated, unsaturated and straight, branched chain having from 2 to 24 carbon atoms, which may or may not contain the same or different hydrogen or hydroxy groups;
A와 B는 서로 같거나 다른 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이다.A and B are alkyl groups containing the same or different saturated, unsaturated and straight chain, branched chain of 2-24 carbon atoms.
포스페이트, 포스포릴 클로라이드, 다이포스페이트, 알코올, 포스페이트 유도체Phosphates, phosphoryl chlorides, diphosphates, alcohols, phosphate derivatives
Description
도 1은 액정베이스의 액정 형성여부를 보여주는 편광현미경 사진이다.1 is a polarized light micrograph showing the liquid crystal formation of the liquid crystal base.
본 발명은 인체의 인지질과 유사한 포스페이트(Phosphate) 구조를 가짐으로써 피부 친화적이고 건조환경에서 우수한 수분 유지 능력을 가지며, 하기 화학식 1로 표시되는 포스페이트 유도체 및 이의 제조방법에 관한 것이다:The present invention relates to a phosphate derivative represented by the following Chemical Formula 1 and a method for preparing the same, having a phosphate structure similar to the phospholipid of the human body and having skin-friendly and excellent moisture retention ability in a dry environment.
[화학식 1][Formula 1]
상기 식 중에서, R은 서로 같거나 다른 수소 또는 히드록시기를 포함하거나 포함하지 않는 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이며;Wherein R is an alkyl group comprising a saturated, unsaturated and straight, branched chain having from 2 to 24 carbon atoms, which may or may not contain the same or different hydrogen or hydroxy groups;
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A와 B는 서로 같거나 다른 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이다.A and B are alkyl groups containing the same or different saturated, unsaturated and straight chain, branched chain of 2-24 carbon atoms.
인체의 피부는 노화가 진행되어 감에 따라서 피부 각질층의 기능이 저하되어 수분 유지 능력이 떨어지며 건조함을 느끼게 된다. 이런 이유로 피부 건조함을 개선하기 위한 보습제의 필요성은 더욱 높아가고 있다. 이전의 보습제들은 각질층에 수분을 제공하는 것을 목적으로 하고 있었으나, 보통 환경에서는 이러한 수분 보유 능력이 좋으나 건조환경에서는 그렇지 못한 특성을 나타내었다. 따라서, 건조환경에서 수분 흡수 능력과 수분 보유 능력이 뛰어난 보습제 개발의 필요성이 대두되었다.As the aging of the human body progresses, the function of the stratum corneum of the skin is lowered, and the ability to retain moisture decreases and feels dry. For this reason, the need for moisturizers to improve skin dryness is increasing. Previous moisturizers were intended to provide moisture to the stratum corneum, but these properties were good in normal environments but not in dry environments. Therefore, there is a need to develop a moisturizer having excellent moisture absorption ability and water retention ability in a dry environment.
또한 현재 시대적으로 친환경적이고 피부성분과 유사하며 각질층의 수분 보유력을 향상시킬 수 있는 물질을 요구하고 있다. 이러한 이유로 인체의 생체막의 주된 성분으로서 중요한 역할을 담당하는 인지질과 유사한 구조를 가지는 피부 보습 물질의 개발이 절실히 필요한 실정이다.In addition, there is a demand for a material that can be environmentally friendly and similar to the skin component of the current era and improve the moisture retention of the stratum corneum. For this reason, there is an urgent need for the development of skin moisturizing substances having a structure similar to phospholipids, which play an important role as main components of the human body's biofilm.
이에 본 발명자들은 인체의 인지질과 유사한 포스페이트(Phosphate) 구조를 가짐으로써 피부 친화적이고 건조환경에서 우수한 수분 유지 능력을 가지는 포스페 이트 유도체에 대하여 연구한 결과, 본 발명을 완성하게 되었다.따라서, 본 발명의 목적은 인체의 인지질과 유사한 구조를 가짐으로써 피부 친화적이고 건조환경에서 각질층의 우수한 수분 유지 능력을 향상시키는 포스페이트 유도체 및 이의 제조방법을 제공하는 것이다.
Accordingly, the present inventors have completed the present invention by studying a phosphate derivative having a phosphate structure similar to the phospholipid of the human body and having skin-friendly and excellent moisture retention ability in a dry environment. An object of the present invention is to provide a phosphate derivative and a method for preparing the same, which have a structure similar to a phospholipid of the human body and are skin-friendly and improve the excellent water retention ability of the stratum corneum in a dry environment.
본 발명에서는 하기 화학식 1로 표시되는 포스페이트 유도체들을 제공한다:The present invention provides phosphate derivatives represented by the following general formula (1):
상기 식 중에서, R은 서로 같거나 다른 수소 또는 히드록시기를 포함하거나 포함하지 않는 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이며;A와 B는 서로 같거나 다른 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기이다.Wherein R is an alkyl group containing from 2 to 24 carbon atoms, saturated and unsaturated, straight and branched, with or without hydrogen or a hydroxy group, wherein A and B are the same or different -24 saturated, unsaturated and linear, branched alkyl groups.
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또한 본 발명에서는 상기 화학식 1로 표시되는 포스페이트 유도체를 제조하는 방법을 제공한다.In another aspect, the present invention provides a method for preparing a phosphate derivative represented by the formula (1).
상기 화학식 1로 표시되는 포스페이트 유도체의 제조방법은, Method for producing a phosphate derivative represented by the formula (1),
(A) 포스포릴 클로라이드(Phosphoryl chloride)와 알코올을 염기 조건하에서 교반시켜 포스페이트 화합물을 만드는 단계; (A) stirring phosphoryl chloride and alcohol under basic conditions to form a phosphate compound;
(B) 포스페이트 화합물과 디올(diol) 계통의 화합물을 염기 조건하에서 반응시켜 다이포스페이트(diphosphate) 화합물을 만드는 단계; 및 (B) reacting a phosphate compound with a diol based compound under basic conditions to form a diphosphate compound; And
(C) 다이포스페이트와 물 또는 알코올류를 반응시켜 화합물을 만드는 단계;(C) reacting the diphosphate with water or alcohols to make a compound;
를 포함하며, 이를 하기 반응식 1로 나타낼 수 있다. It includes, it can be represented by the following scheme 1.
상기 식 중에서, R, A 및 B는 상기 화학식 1에서 정의된 바와 같다.
Wherein R, A and B are as defined in Formula 1 above.
본 발명에 따른 포스페이트 유도체의 제조방법을 보다 구체적으로 설명하면 다음과 같다:The preparation method of the phosphate derivative according to the present invention will be described in more detail as follows:
(A) 포스포릴 클로라이드와 알코올을 염기 조건하에서 반응시켜 포스페이트 화합물을 만드는 단계;(A) reacting phosphoryl chloride with alcohol under basic conditions to form a phosphate compound;
상기 (A)단계에서 사용할 수 있는 알코올로는 탄소개수 1-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하며 히드록시기를 1개 이상 포함하는 알코올로서, 그 예로는 프로판올, 부탄올, 펜탄올, 헥산올, 헵탄올, 펜탄올, 노난올, 데칸올, 도데칸올, 테트라데칸올, 헥사데칸올, 옥타데칸올, 2-에틸헥산올, 3,7-디메틸옥탄올, 2-헥실데칸올, 이소스테아일 알코올, 제라니올, 파네솔과 에틸렌글리콜, 매니톨, 소비톨, 글루코스 및 글리세롤과 같은 다가알코올에서 선택될 수 있으나 여기에 국한되는 것은 아니다. The alcohol that can be used in the step (A) is an alcohol containing 1-4 or more hydroxy groups including saturated, unsaturated and straight chain, branched chain having 1-2 carbon atoms, for example propanol, butanol, pentanol, hexane Ol, heptanol, pentanol, nonanol, decanol, dodecanol, tetradecanol, hexadecanol, octadecanol, 2-ethylhexanol, 3,7-dimethyloctanol, 2-hexyldecanol, iso Stearyl alcohol, geraniol, farnesol and polyhydric alcohols such as ethylene glycol, mannitol, sorbitol, glucose and glycerol may be selected, but not limited thereto.
또한 상기 단계에서 사용하는 유기용매로는 테트라히드로퓨란, 디클로로메탄과 같은 용매가 바람직하며, 이러한 용매와 초산에틸, 아세토니트릴, 클로로포름, 에틸에테르, 트리클로로 에틸렌, 디메틸포름아미드와 같은 용매와의 혼합 용매도 가능하다. In addition, the organic solvent used in the above step is preferably a solvent such as tetrahydrofuran and dichloromethane, and mixing such a solvent with a solvent such as ethyl acetate, acetonitrile, chloroform, ethyl ether, trichloroethylene, and dimethylformamide. Solvents are also possible.
상기 단계에서 사용하는 염기로는 트리에틸아민, 피리딘과 같은 유기염기 등이 가능하며 바람직하게는 트리에틸아민을 사용하는 것이다. 그리고 염기의 당량은 1 ~ 2 당량까지 가능하나 가장 적당한 사용량은 1.2 당량이 바람직하다.The base used in the step may be an organic base such as triethylamine, pyridine and the like, and preferably triethylamine. The base equivalent may be 1 to 2 equivalents, but the most suitable amount is preferably 1.2 equivalents.
(B) 포스페이트 화합물과 디올 계통의 화합물을 염기 조건하에서 반응시켜 다이포스페이트 화합물을 만드는 단계;(B) reacting a phosphate compound with a diol-based compound under basic conditions to form a diphosphate compound;
상기 (B)단계에서 사용할 수 있는 디올은 탄소 개수 2-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하는 알킬기로 이루어진 디올로서, 예로는 에틸렌 글리콜(Ethylene glycol), 1,3-프로판디올(1,3-Propanediol), 1,4-부탄디올(1,4- Butanediol), 1,5-펜탄디올(1,5-Pentanediol), 1,6-헥산디올(1,6-Hexanediol), 1,7-헵탄디올(1,7-Heptanediol), 1,8-옥탄디올(1,8-Octanediol), 1,9-노난디올(1,9-Nonanediol), 1,10-데칸디올(1,10-Decanediol), 에리트리톨(Erythritol), 디에틸렌 글리콜(Diethylene glycol), 트리에틸렌 글리콜(Triethylene glycol) 및 테트라에틸렌 글리콜(Tetraethylene glycol)에서 선택될 수 있으나 여기에 국한되는 것은 아니다. The diol which can be used in the step (B) is a diol consisting of an alkyl group containing a saturated, unsaturated and straight chain, branched chain of 2-24 carbon atoms, for example, ethylene glycol, 1,3-propanediol ( 1,3-Propanediol), 1,4-butanediol (1,4-Butanediol), 1,5-pentanediol (1,5-Pentanediol), 1,6-hexanediol (1,6-Hexanediol), 1, 7-heptanediol (1,7-Heptanediol), 1,8-octanediol (1,8-Octanediol), 1,9-nonanediol (1,9-Nonanediol), 1,10-decanediol (1,10 Decanediol), erythritol, diethylene glycol, diethylene glycol, triethylene glycol and tetraethylene glycol, but are not limited thereto.
이 단계에서 사용할 수 있는 유기용매로는 디클로로메탄, 테트라히드로퓨란, 초산에틸, 아세토니트릴, 클로로포름, 에틸에테르, 트리클로로 에틸렌, 벤젠, 톨루엔, 디메틸포름아미드, 디메틸술폭사이드 등과 같은 용매를 사용할 수 있다. The organic solvent used in this step may be a solvent such as dichloromethane, tetrahydrofuran, ethyl acetate, acetonitrile, chloroform, ethyl ether, trichloroethylene, benzene, toluene, dimethylformamide, dimethyl sulfoxide and the like. .
또한 상기 단계에서 사용하는 염기로는 피리딘, 트리에틸아민 등의 유기염기를 사용할 수 있으며, 바람직하게는 트리에틸아민을 사용하는 것이다.In addition, as the base used in the above step, an organic base such as pyridine and triethylamine may be used, and preferably triethylamine is used.
(C) 다이포스페이트와 물 또는 알코올류를 반응시켜 화합물을 만드는 단계;(C) reacting the diphosphate with water or alcohols to make a compound;
상기 (C) 단계에서 사용할 수 있는 알코올로는 탄소 개수 1-24개의 포화, 불포화 및 직쇄, 분지쇄를 포함하며 히드록시기를 1개 이상 포함하는 알코올로서, 그 예로는 프로판올, 부탄올, 펜탄올, 헥산올, 헵탄올, 펜탄올, 노난올, 데칸올, 도데칸올, 테트라데칸올, 헥사데칸올, 옥타데칸올, 2-에틸헥산올, 3,7-디메틸옥탄올, 2-헥실데칸올,이소스테아일 알코올, 제라니올, 파네솔과 에틸렌글리콜, 매니톨, 소비톨, 글루코스 및 글리세롤과 같은 다가알코올에서 선택될 수 있으나 여기에 국한되는 것은 아니다. Alcohols that may be used in the step (C) include saturated, unsaturated and straight chain, branched chain having 1-24 carbon atoms, and alcohol having one or more hydroxy groups, for example propanol, butanol, pentanol, hexane Ol, heptanol, pentanol, nonanol, decanol, dodecanol, tetradecanol, hexadecanol, octadecanol, 2-ethylhexanol, 3,7-dimethyloctanol, 2-hexyldecanol, iso Stearyl alcohol, geraniol, farnesol and polyhydric alcohols such as ethylene glycol, mannitol, sorbitol, glucose and glycerol may be selected, but not limited thereto.
상기 단계에서 사용하는 유기용매로는 테트라히드로퓨란, 디클로로메탄과 같은 용매가 바람직하며, 이러한 용매와 초산에틸, 아세토니트릴, 클로로포름, 에틸에테르, 트리클로로 에틸렌, 디메틸포름아미드와 같은 용매와의 혼합 용매도 가능하다. The organic solvent used in the step is preferably a solvent such as tetrahydrofuran or dichloromethane, and a mixed solvent of such a solvent with a solvent such as ethyl acetate, acetonitrile, chloroform, ethyl ether, trichloroethylene, and dimethylformamide. It is also possible.
또한 상기 단계에서 사용하는 염기로는 트리에틸아민, 피리딘과 같은 유기염기 등이 가능하며, 바람직하게는 트리에틸아민을 사용하는 것이다. 그리고 염기의 당량은 1∼2 당량까지 가능하나 가장 적당한 사용량은 1.2 당량이 바람직하다.In addition, the base used in the step may be an organic base such as triethylamine, pyridine, and the like, and preferably triethylamine is used. The base equivalent may be 1 to 2 equivalents, but the most suitable amount is preferably 1.2 equivalents.
또한 본 발명은 상기 포스페이트 유도체를 피부내에 존재하는 지방산, 콜레스테롤 등의 지질과 함께 사용하여 각각의 함량이 포스페이트 유도체 10∼70 중량%, 지방산 5∼50 중량% 및 콜레스테롤 10∼50 중량%가 되는 조성으로 혼합하여 만든 액정 베이스에 관한 것이다.In addition, the present invention is to use the phosphate derivatives together with lipids such as fatty acids, cholesterol, etc. present in the skin, each of which is 10 to 70% by weight of phosphate derivatives, 5 to 50% by weight of fatty acids and 10 to 50% by weight of cholesterol It relates to a liquid crystal base made by mixing.
이하, 실시예를 통하여 본 발명을 보다 더 구체적으로 설명하지만, 본 발명이 이들 실시예로만 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.
[실시예 1] 헥사데칸올-헥산디올-에틸렌 글리콜-포스페이트 (Hexadecanol-Hexanediol-Ethylene glycol-Phosphate)Example 1 Hexadecanol-Hexanediol-Ethylene glycol-Phosphate
헥사데칸올 121g(500mmol)과 트리에틸아민 84ml(600mmol)을 테트라히드로퓨란 600ml에 녹였다. 그런 다음 포스포릴 클로라이드 46ml(500mmol)를 테트라히드로 튜란에 교반시킨 후 4℃에서 녹인 용액을 천천히 적가한 다음 3시간 동안 교반하여 염을 생성하였다. 교반 반응이 종료되면 생성된 염을 필터하여 제거한 후 농축하였다. 준비된 농축물을 테트라히드로퓨란 400ml로 희석하여 4℃에서 교반시켜주고, 1,6-헥산디올 30g(250mmol)과 트리에틸아민 84ml(600mmol)을 테트라히드로퓨란 200ml에 녹인 후 천천히 적가하여 6시간 교반하였다. 염이 침전되어 반응이 종결되면 염을 제거하고 농축하였다.121 g (500 mmol) of hexadecanol and 84 ml (600 mmol) of triethylamine were dissolved in 600 ml of tetrahydrofuran. Then, 46 ml (500 mmol) of phosphoryl chloride was stirred in tetrahydroturan, and the solution dissolved at 4 ° C was slowly added dropwise, followed by stirring for 3 hours to form a salt. When the stirring reaction was completed, the resulting salt was filtered off and concentrated. The prepared concentrate was diluted with 400 ml of tetrahydrofuran and stirred at 4 ° C. After dissolving 30 g (250 mmol) of 1,6-hexanediol and 84 ml (600 mmol) of triethylamine in 200 ml of tetrahydrofuran, the mixture was slowly added dropwise and stirred for 6 hours. It was. When the salt precipitated out and the reaction was completed, the salt was removed and concentrated.
농축한 생성물을 테트라히드로퓨란 400ml에 희석하여 교반하고 여기에 에틸렌글리콜 68g(1100mmol)과 트리에틸아민 160ml(1100mmol)를 테트라히드로퓨란 200ml에 희석시킨 다음 적가하여 6시간 교반하여 침전되는 염을 필터로 제거한 후 농축하고 컬럼을 통하여 헥사데칸올-헥산디올-에틸렌 글리콜-포스페이트 171g을 얻었다.The concentrated product was diluted with 400 ml of tetrahydrofuran and stirred, and 68 g (1100 mmol) of ethylene glycol and 160 ml (1100 mmol) of triethylamine were diluted with 200 ml of tetrahydrofuran, and then added dropwise and stirred for 6 hours to precipitate a salt that was precipitated with a filter. After removal and concentration, 171 g of hexadecanol-hexanediol-ethylene glycol-phosphate was obtained through a column.
1H NMR (in CHCl3) : 4.06(6H, m), 3.9(2H, t), 2.0(1H, s), 1.68(4H, m), 1.25(28H, m), 0.89(3H, t). 1 H NMR (in CHCl 3 ): 4.06 (6H, m), 3.9 (2H, t), 2.0 (1H, s), 1.68 (4H, m), 1.25 (28H, m), 0.89 (3H, t) .
[실시예 2] 데칸올-헥산디올-에틸렌 글리콜-포스페이트 (Decanol-Hexanediol-Ethylene glycol-Phosphate)Example 2 Decanol-Hexanediol-Ethylene glycol-Phosphate
헥사데칸올 대신에 데칸올 79.2g(500mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-헥산디올-에틸렌 글리콜-포스페이트 121g을 얻었다.121.decanol-hexanediol-ethylene glycol-phosphate was obtained in the same manner as in Example 1, using 79.2 g (500 mmol) of decanol instead of hexadecanol.
1H NMR (in CHCl3) : 4.03(6H, m), 3.91(2H, t), 2.0(1H, s), 1.72(4H, m), 1.30(16H, m), 0.92(3H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, m), 3.91 (2H, t), 2.0 (1H, s), 1.72 (4H, m), 1.30 (16H, m), 0.92 (3H, t) .
[실시예 3] 도데칸올-헥산디올-에틸렌 글리콜-포스페이트 (Dodecanol-Hexanediol-Ethylene glycol-Phosphate)Example 3 Dodecanol-Hexanediol-Ethylene glycol-Phosphate
헥사데칸올 대신에 도데칸올 93.2g(500mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-헥산디올-에틸렌 글리콜-포스페이트 154g을 얻었다.154 g of dodecanol-hexanediol-ethylene glycol-phosphate was obtained in the same manner as in Example 1 using 93.2 g (500 mmol) of dodecanol instead of hexadecanol.
1H NMR (in CHCl3) : 4.03(6H, m), 3.93(2H, t), 2.0(1H, s), 1.61(4H, m), 1.31(20H, m), 0.83(3H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, m), 3.93 (2H, t), 2.0 (1H, s), 1.61 (4H, m), 1.31 (20H, m), 0.83 (3H, t) .
[실시예 4] 펜탄올-헥산디올-에틸렌 글리콜-포스페이트 (Pentanol-Hexanediol-Ethylene glycol-Phosphate)Example 4 Pentanol-Hexanediol-Ethylene glycol-Phosphate
헥사데칸올 대신에 펜탄올 44.1g(500mmol)을 사용하여 실시예 1과 같은 방법으로 펜탄올-헥산디올-에틸렌 글리콜 포스페이트 89g을 얻었다.Using pentanol 44.1 g (500 mmol) instead of hexadecanol, 89 g of pentanol-hexanediol-ethylene glycol phosphate was obtained in the same manner as in Example 1.
1H NMR (in CHCl3) : 4.10(6H, m), 3.86(2H, t), 2.0(1H, s), 1.68(4H, m), 1.25(12H, m), 0.92(3H, t). 1 H NMR (in CHCl 3 ): 4.10 (6H, m), 3.86 (2H, t), 2.0 (1H, s), 1.68 (4H, m), 1.25 (12H, m), 0.92 (3H, t) .
[실시예 5] 테트라데칸올-헥산디올-에틸렌 글리콜-포스페이트 (Tetradecanol-Hexanediol-Ethylene glycol-Phosphate)[Example 5] Tetradecanol-hexanediol-ethylene glycol-phosphate (Tetradecanol-Hexanediol-Ethylene glycol-Phosphate)
헥사데칸올 대신에 테트라데칸올 107.2g(500mmol)을 사용하여 실시예 1과 같은 방법으로 테트라데칸올-헥산디올-에틸렌 글리콜-포스페이트 135g을 얻었다.Instead of hexadecanol, tetradecanol (107.2 g (500 mmol)) was used to obtain 135 g of tetradecanol-hexanediol-ethylene glycol-phosphate in the same manner as in Example 1.
1H NMR (in CHCl3) : 4.02(6H, m), 3.9(2H, t), 2.02(1H, s), 1.68(4H, m), 1.25(24H, m), 0.89(3H, t). 1 H NMR (in CHCl 3 ): 4.02 (6H, m), 3.9 (2H, t), 2.02 (1H, s), 1.68 (4H, m), 1.25 (24H, m), 0.89 (3H, t) .
[실시예 6] 2-에틸헥산올-헥산디올-에틸렌 글리콜-포스페이트 (2-Ethylhexanol-Hexanediol-Ethylene glycol-Phosphate)Example 6 2-Ethylhexanol-hexanediol-ethylene glycol-phosphate (2-Ethylhexanol-Hexanediol-Ethylene glycol-Phosphate)
헥사데칸올 대신에 2-에틸헥산올 65.1g(500mmol)을 사용하여 실시예 1과 같은 방법으로 2-에틸헥산올-헥산디올-에틸렌 글리콜-포스페이트 124g을 얻었다.124 g of 2-ethylhexanol-hexanediol-ethylene glycol-phosphate was obtained in the same manner as in Example 1, using 65.1 g (500 mmol) of 2-ethylhexanol instead of hexadecanol.
1H NMR (in CHCl3) : 4.12(6H, m), 3.89(2H, t), 2.0(1H, s), 1.68(2H, m), 1.56(1H,S), 1.25(10H, m), 0.92(6H, t). 1 H NMR (in CHCl 3 ): 4.12 (6H, m), 3.89 (2H, t), 2.0 (1H, s), 1.68 (2H, m), 1.56 (1H, S), 1.25 (10H, m) , 0.92 (6H, t).
[실시예 7] 헥사데칸올-헥산디올-히드록시-포스페이트 (Hexadecanol-Hexanediol-Hydroxy-Phosphate)Example 7 Hexadecanol-hexanediol-hydroxy-phosphate (Hexadecanol-Hexanediol-Hydroxy-Phosphate)
에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-헥산디올-히드록시-포스페이트 85g을 얻었다.Instead of ethylene glycol, 19.8 g (1100 mmol) of water was used to obtain 85 g of hexadecanol-hexanediol-hydroxy-phosphate in the same manner as in Example 1.
1H NMR (in CHCl3) : 3.61(4H, t), 2.02(1H, s), 1.49(4H, m), 1.29(28H, m), 0.96(3H, t). 1 H NMR (in CHCl 3 ): 3.61 (4H, t), 2.02 (1H, s), 1.49 (4H, m), 1.29 (28H, m), 0.96 (3H, t).
[실시예 8] 헥사데칸올-헥산디올-프로판올-포스페이트 (Hexadecanol-Hexanediol-Propanol-Phosphate)Example 8 Hexadecanol-Hexanediol-Propanol-Phosphate
에틸렌 글리콜 대신에 프로판올 66.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-헥산디올-프로판올-포스페이트 104g을 얻었다.104 g of hexadecanol-hexanediol-propanol-phosphate was obtained in the same manner as in Example 1 using 66.1 g (1100 mmol) of propanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.06(6H, m), 1.68(6H, m), 1.28(34H, m), 0.90(6H, t). 1 H NMR (in CHCl 3 ): 4.06 (6H, m), 1.68 (6H, m), 1.28 (34H, m), 0.90 (6H, t).
[실시예 9] 헥사데칸올-헥산디올-펜탄올-포스페이트 (Hexadecanol-Hexanediol-Pentanol-Phosphate)Example 9 Hexadecaneol-hexanediol-pentanol-phosphate (Hexadecanol-Hexanediol-Pentanol-Phosphate)
에틸렌 글리콜 대신에 펜탄올 97.0g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-헥산디올-펜탄올-포스페이트 144g을 얻었다. 144 g of hexadecanol-hexanediol-pentanol-phosphate was obtained in the same manner as in Example 1 using 97.0 g (1100 mmol) of pentanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.03(6H, m), 1.68(6H, m), 1.30(28H, m), 0.92(6H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, m), 1.68 (6H, m), 1.30 (28H, m), 0.92 (6H, t).
[실시예 10] 헥사데칸올-헥산디올-데칸올-포스페이트 (Hexadecanol-Hexanediol-Decanol-Phosphate)Example 10 Hexadecanol-hexanediol-decanol-phosphate (Hexadecanol-Hexanediol-Decanol-Phosphate)
에틸렌 글리콜 대신에 데칸올 174.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-헥산디올-데칸올-포스페이트 211g을 얻었다.Instead of ethylene glycol, 174.1 g (1100 mmol) of decanol was used to obtain 211 g of hexadecanol-hexanediol-decanol-phosphate in the same manner as in Example 1.
1H NMR (in CHCl3) : 4.03(6H, m), 1.68(6H, m), 1.30(42H, m), 0.92(6H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, m), 1.68 (6H, m), 1.30 (42H, m), 0.92 (6H, t).
[실시예 11] 데칸올-헥산디올-히드록시-포스페이트 (Decanol-Hexanediol-Hydroxy-Phosphate)Example 11 Decanol-Hexanediol-Hydroxy-Phosphate
헥사데칸올 대신에 데칸올 79.2g(500mmol)과 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-헥산디올-히드록시-포스페이트 76g을 얻었다.76 g of decanol-hexanediol-hydroxy-phosphate was obtained in the same manner as in Example 1, using 79.2 g (500 mmol) of decanol instead of hexadecanol and 19.8 g (1100 mmol) of water instead of ethylene glycol.
1H NMR (in CHCl3) : 3.53(4H, t), 2.02(1H, s), 1.48(4H, m), 1.30(14H, m), 0.91(3H, t). 1 H NMR (in CHCl 3 ): 3.53 (4H, t), 2.02 (1H, s), 1.48 (4H, m), 1.30 (14H, m), 0.91 (3H, t).
[실시예 12] 데칸올-헥산디올-프로판올-포스페이트 (Decanol-Hexanediol-Propanol-Phosphate)Example 12 Decanol-Hexanediol-Propanol-Phosphate
헥사데칸올 대신에 데칸올 79.2g(500mmol)과 에틸렌 글리콜 대신에 프로판올 66.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-헥산디올-프로판올-포스페이트 112g을 얻었다Decanol-hexanediol-propanol-phosphate 112 g was obtained in the same manner as in Example 1 using 79.2 g (500 mmol) of decanol instead of hexadecanol and 66.1 g (1100 mmol) of propanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.11(6H, m), 1.70(6H, m), 1.25(16H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.11 (6H, m), 1.70 (6H, m), 1.25 (16H, m), 0.95 (6H, t).
[실시예 13] 데칸올-헥산디올-헵탄올-포스페이트 (Decanol-Hexanediol-Heptanol-Phosphate)Example 13 Decanol-Hexanediol-Heptanol-Phosphate
헥사데칸올 대신에 데칸올 79.2g(500mmol)과 에틸렌 글리콜 대신에 헵탄올 127.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-헥산디올-헵탄올-포스페이트 112g을 얻었다Decanol-hexanediol-heptanol-phosphate 112 g was obtained in the same manner as in Example 1 using 79.2 g (500 mmol) of decanol instead of hexadecanol and 127.8 g (1100 mmol) of heptanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.09 (6H, m), 1.69(6H, m), 1.20(26H, m), 0.91(6H, t). 1 H NMR (in CHCl 3 ): 4.09 (6H, m), 1.69 (6H, m), 1.20 (26H, m), 0.91 (6H, t).
[실시예 14] 데칸올-헥산디올-도데칸올-포스페이트 (Decanol-Hexanediol-dodecanol-Phosphate)Example 14 Decanol-Hexanediol-dodecanol-Phosphate
헥사데칸올 대신에 데칸올 79.2g(500mmol)과 에틸렌 글리콜 대신에 도데칸올 204.9g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-헥산디올-도데칸올-포스페이트 197g을 얻었다.197 g of decanol-hexanediol-dodecanol-phosphate was obtained in the same manner as in Example 1, using 79.2 g (500 mmol) of decanol instead of hexadecanol and 204.9 g (1100 mmol) of dodecanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.11 (6H, m), 1.71(6H, m), 1.22(32H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.11 (6H, m), 1.71 (6H, m), 1.22 (32H, m), 0.95 (6H, t).
[실시예 15] 도데칸올-헥산디올-히드록시-포스페이트 (Dodecanol-Hexanediol-Hydroxy-Phosphate)Example 15 Dodecanol-hexanediol-hydroxy-phosphate (Dodecanol-Hexanediol-Hydroxy-Phosphate)
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-헥산디올-히드록시-포스페이트 74g을 얻었다.74 g of dodecanol-hexanediol-hydroxy-phosphate was obtained in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol and 19.8 g (1100 mmol) of water instead of ethylene glycol.
1H NMR (in CHCl3) : 3.61(4H, t), 2.06(1H, s), 1.41(4H, m), 1.29(18H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 3.61 (4H, t), 2.06 (1H, s), 1.41 (4H, m), 1.29 (18H, m), 0.95 (3H, t).
[실시예 16] 도데칸올-헥산디올-프로판올-포스페이트 (Dodecanol-Hexanediol-Propanol-Phosphate)Example 16 Dodecanol-Hexanediol-Propanol-Phosphate
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 에틸렌 글리콜 대신에 프로판올 66.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-헥산디올-프로판올-포스페이트 126g을 얻었다.126 g of dodecanol-hexanediol-propanol-phosphate was obtained in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol and 66.1 g (1100 mmol) of propanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.09(6H, m), 1.74(2H, m), 1.68(4H, m), 1.28(18H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.09 (6H, m), 1.74 (2H, m), 1.68 (4H, m), 1.28 (18H, m), 0.96 (6H, t).
[실시예 17] 도데칸올-헥산디올-펜탄올-포스페이트 (Dodecanol-Hexanediol- Pentanol-Phosphate)Example 17 Dodecanol-Hexanediol-Pentanol-Phosphate
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 에틸렌 글리콜 대신에 펜탄올 97g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-헥산디올-펜탄올-포스페이트 138g을 얻었다.138 g of dodecanol-hexanediol-pentanol-phosphate was obtained in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol and 97 g (1100 mmol) of pentanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.07(6H, m), 1.69(6H, m), 1.20(30H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.07 (6H, m), 1.69 (6H, m), 1.20 (30H, m), 0.96 (6H, t).
[실시예 18] 도데칸올-헥산디올-헥실데칸올-포스페이트 (Dodecanol-Hexanediol-Hexyldecanol-Phosphate)Example 18 Dodecanol-Hexanediol-Hexyldecanol-Phosphate
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 에틸렌 글리콜 대신에 헥실데칸올 266.7g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-헥산디올-헥실데칸올-포스페이트 204g을 얻었다.204 g of dodecanol-hexanediol-hexyldecanol-phosphate was obtained in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol and 266.7 g (1100 mmol) of hexyldecanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.19(4H, m), 3.95(2H, d), 1.70(4H, m), 1.56(1H, d), 1.22(44H, m), 0.95(9H, t). 1 H NMR (in CHCl 3 ): 4.19 (4H, m), 3.95 (2H, d), 1.70 (4H, m), 1.56 (1H, d), 1.22 (44H, m), 0.95 (9H, t) .
[실시예 19] 펜탄올-헥산디올-히드록시-포스페이트 (Pentanol-Hexanediol-Hydroxy-Phosphate)Example 19 Pentanol-hexanediol-hydroxy-phosphate (Pentanol-Hexanediol-Hydroxy-Phosphate)
헥사데칸올 대신에 펜탄올 44.1g(500mmol)과 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 펜탄올-헥산디올-히드록시-포스페이트 65g을 얻었다.65 g of pentanol-hexanediol-hydroxy-phosphate was obtained in the same manner as in Example 1, using 44.1 g (500 mmol) of pentanol instead of hexadecanol and 19.8 g (1100 mmol) of water instead of ethylene glycol.
1H NMR (in CHCl3) : 3.53(4H, t), 2.05(1H, s), 1.47(4H, m), 1.25(12H, m), 0.96(3H, t). 1 H NMR (in CHCl 3 ): 3.53 (4H, t), 2.05 (1H, s), 1.47 (4H, m), 1.25 (12H, m), 0.96 (3H, t).
[실시예 20] 펜탄올-헥산디올-프로판올-포스페이트 (Pentanol-Hexanediol-Propanol-Phosphate)Example 20 Pentanol-hexanediol-propanol-phosphate (Pentanol-Hexanediol-Propanol-Phosphate)
헥사데칸올 대신에 펜탄올 44.1g(500mmol)과 에틸렌 글리콜 대신에 프로판올 66.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 펜탄올-헥산디올-프로판올-포스페이트 89g을 얻었다.Pentanol-hexanediol-propanol-phosphate 89g was obtained in the same manner as in Example 1, using 44.1 g (500 mmol) of pentanol instead of hexadecanol and 66.1 g (1100 mmol) of propanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.03(6H, t), 1.70(2H, m), 1.64(4H, m), 1.25(12H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, t), 1.70 (2H, m), 1.64 (4H, m), 1.25 (12H, m), 0.96 (6H, t).
[실시예 21] 헥사데칸올-부탄디올-에틸렌 글리콜-포스페이트 (Hexadecanol-Butanediol-Ethylene glycol-Phosphate)Example 21 Hexadecanol-Butanediol-Ethylene Glycol-Phosphate (Hexadecanol-Butanediol-Ethylene glycol-Phosphate)
헥산디올 대신에 부탄디올 22.53g(250mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-부탄디올-에틸렌 글리콜-포스페이트 116g을 얻었다.Butanediol 22.53 g (250 mmol) was used instead of hexanediol and 116 g of hexadecanol-butanediol-ethylene glycol-phosphate was obtained in the same manner as in Example 1.
1H NMR (in CHCl3) : 4.22(2H, t), 4.07(4H, t), 3.90(2H, m), 2.01(1H, s), 1.66(4H, m), 1.22(26H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 4.22 (2H, t), 4.07 (4H, t), 3.90 (2H, m), 2.01 (1H, s), 1.66 (4H, m), 1.22 (26H, m) , 0.95 (3H, t).
[실시예 22] 헥산데칸올-부탄디올-히드록시-포스페이트 (Hexadecanol-Butanediol-Hydroxy-Phosphate)Example 22 Hexadecanol-butanediol-hydroxy-phosphate (Hexadecanol-Butanediol-Hydroxy-Phosphate)
헥산디올 대신에 부탄디올 22.53g(250mmol)과 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥산데칸올-부탄디올-히드록시-포스페이트 58g을 얻었다.Instead of hexanediol, 22.53 g (250 mmol) of butanediol and 19.8 g (1100 mmol) of water instead of ethylene glycol were used to obtain 58 g of hexanedecanol-butanediol-hydroxy-phosphate in the same manner as in Example 1.
1H NMR (in CHCl3) : 3.53(4H, t), 2.0(1H, s), 1.48(4H, m), 1.22(26H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 3.53 (4H, t), 2.0 (1H, s), 1.48 (4H, m), 1.22 (26H, m), 0.95 (3H, t).
[실시예 23] 도데칸올-부탄디올-프로판올-포스페이트 (Dodecanol-Butanediol-Propanol-Phosphate)Example 23 Dodecanol-Butanediol-Propanol-Phosphate (Dodecanol-Butanediol-Propanol-Phosphate)
헥사데칸올 대신 도데칸올 93.17g(500mmol), 헥산디올 대신에 부탄디올 22.53g(250mmol), 에틸렌 글리콜 대신에 프로판올 60.11g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-부탄디올-프로판올-포스페이트 64g을 얻었다.Dodecanol-butanediol-propanol- 93.17 g (500 mmol) instead of hexadecanol, butanediol 22.53 g (250 mmol) instead of hexanediol, and 60.11 g (1100 mmol) propanol instead of ethylene glycol in the same manner as in Example 1 64 g of phosphate were obtained.
1H NMR (in CHCl3) : 4.07(4H, t), 1.70(6H, m), 1.22(18H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.07 (4H, t), 1.70 (6H, m), 1.22 (18H, m), 0.95 (6H, t).
[실시예 24] 데칸올-부탄디올-에틸렌 글리콜-포스페이트 (Decanol-Butanediol-Ethylene glycol-Phosphate)Example 24 Decanol-Butanediol-Ethylene glycol-Phosphate
헥사데칸올 대신 데칸올 79.14g(500mmol), 헥산디올 대신에 부탄디올 22.53g (250mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-부탄디올-에틸렌 글리콜-포스페이트 75g을 얻었다.75.decanol-butanediol-ethylene glycol-phosphate was obtained in the same manner as in Example 1, using 79.14 g (500 mmol) of decanol instead of hexadecanol and 22.53 g (250 mmol) of butanediol instead of hexanediol.
1H NMR (in CHCl3) : 4.24(2H, t), 4.04(4H, t), 3.91(2H, m), 2.00(1H, s), 1.67(4H, m), 1.22(14H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 4.24 (2H, t), 4.04 (4H, t), 3.91 (2H, m), 2.00 (1H, s), 1.67 (4H, m), 1.22 (14H, m) , 0.95 (3H, t).
[실시예 25] 헥산데칸올-다이(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 (Hexadecanol-Di(ethylene glycol)-Ethylene glycol-Phosphate)헥산디올 대신에 다이에틸렌 글리콜 26.5g(250mmol)을 사용하여 실시예 1과 같은 방법으로 헥산데칸올-다이(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 159g을 얻었다.[Example 25] Example of using diethylene glycol 26.5 g (250 mmol) instead of hexanedecanol-di (ethylene glycol) -ethylene glycol-phosphate (Hexadecanol-Di (ethylene glycol) -Ethylene glycol-Phosphate) hexanediol In the same manner as in 1, 159 g of hexanedecanol-di (ethylene glycol) -ethylene glycol-phosphate was obtained.
1H NMR (in CHCl3) : 4.23(4H, t), 4.05(2H, t), 3.90(2H, t), 2.0(1H, s), 1.70(2H, m), 1.25(26H, m), 0.91(3H, t). 1 H NMR (in CHCl 3 ): 4.23 (4H, t), 4.05 (2H, t), 3.90 (2H, t), 2.0 (1H, s), 1.70 (2H, m), 1.25 (26H, m) , 0.91 (3H, t).
[실시예 26] 헥산데칸올-다이(에틸렌 글리콜)-헵탄올-포스페이트 (Hexadecanol-Di(ethylene glycol)-Heptanol-Phosphate)Example 26 Hexadecanol-di (ethylene glycol) -heptanol-phosphate (Hexadecanol-Di (ethylene glycol) -Heptanol-Phosphate)
헥산디올 대신에 다이에틸렌 글리콜 26.5g(250mmol)과 에틸렌 글리콜 대신 헵탄올 127.82(1100mmol)을 사용하여 실시예 1과 같은 방법으로 204g을 헥산데칸올-다이(에틸렌 글리콜)-헵탄올-포스페이트 189g을 얻었다. 204 g of hexanedecanol-di (ethylene glycol) -heptanol-phosphate was added in the same manner as in Example 1, using 26.5 g (250 mmol) of diethylene glycol instead of hexanediol and 127.82 (1100 mmol) of heptanol instead of ethylene glycol. Got it.
1H NMR (in CHCl3) : 4.21(2H, t), 4.05(4H, t), 3.75(2H, t), 1.66(4H, m), 1.21(34H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.21 (2H, t), 4.05 (4H, t), 3.75 (2H, t), 1.66 (4H, m), 1.21 (34H, m), 0.95 (6H, t) .
[실시예 27] 데칸올-다이(에틸렌 글리콜)-히드록시-포스페이트 (Decanol-Di(ethylene glycol)-Hydroxy-Phosphate)Example 27 Decanol-Di (ethylene glycol) -Hydroxy-Phosphate
헥사데칸올 대신 데칸올 79.14g(500mmol), 헥산디올 대신에 다이에틸렌 글리콜 26.5g(250mmol), 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 데칸올-다이(에틸렌 글리콜)-히드록시-포스페이트 59g을 얻었다.Decanol-di (79.14 g (500 mmol) instead of hexadecanol, diethylene glycol 26.5 g (250 mmol) instead of hexanediol, 19.8 g (1100 mmol) water instead of ethylene glycol was used in the same manner as in Example 1 59 g of ethylene glycol) -hydroxy-phosphate was obtained.
1H NMR (in CHCl3) : 3.80(2H, t), 3.56(4H, t), 2.1(1H, s), 1.50(2H, m), 1.28(14H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 3.80 (2H, t), 3.56 (4H, t), 2.1 (1H, s), 1.50 (2H, m), 1.28 (14H, m), 0.95 (3H, t) .
[실시예 28] 도데칸올-다이(에틸렌 글리콜)-프로판올-포스페이트 (Dodecanol- Di(ethylene glycol)-Propanol-Phosphate)Example 28 Dodecanol-di (ethylene glycol) -propanol-phosphate (Dodecanol-Di (ethylene glycol) -Propanol-Phosphate)
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 헥산디올 대신에 다이에틸렌 글리콜 26.5g(250mmol), 에틸렌 글리콜 대신에 프로판올 66.11g (1100mmol)을 사 용하여 실시예 1과 같은 방법으로 도데칸올-다이(에틸렌 글리콜)-프로판올-포스페이트 126g을 얻었다.Dodecanol-die in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol, 26.5 g (250 mmol) of diethylene glycol instead of hexanediol, and 66.11 g (1100 mmol) of propanol instead of ethylene glycol 126 g of (ethylene glycol) -propanol-phosphate was obtained.
1H NMR (in CHCl3) : 4.20(2H, t), 4.01(4H, t), 3.70(2H, t), 1.70(4H, m), 1.21(18H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.01 (4H, t), 3.70 (2H, t), 1.70 (4H, m), 1.21 (18H, m), 0.95 (6H, t) .
[실시예 29] 도데칸올-트리(에틸렌 글리콜)-히드록시-포스페이트 (Dodecanol-Tri(ethylene glycol)-Hydroxy-Phosphate)Example 29 Dodecanol-tri (ethylene glycol) -hydroxy-phosphate (Dodecanol-Tri (ethylene glycol) -Hydroxy-Phosphate)
헥사데칸올 대신에 도데칸올 93.2g(500mmol), 헥산디올 대신에 트리에틸렌 글리콜 37.5g(250mmol), 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-트리(에틸렌 글리콜)-히드록시-포스페이트 87g을 얻었다.Dodecanol-Tree in the same manner as Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol, 37.5 g (250 mmol) of triethylene glycol instead of hexanediol, and 19.8 g (1100 mmol) of water instead of ethylene glycol 87 g of (ethylene glycol) -hydroxy-phosphate was obtained.
1H NMR (in CHCl3) : 3.71(2H, t), 3.54(4H, t), 2.0(1H, s), 1.49(2H, m), 1.20(18H, m), 0.97(3H, t). 1 H NMR (in CHCl 3 ): 3.71 (2H, t), 3.54 (4H, t), 2.0 (1H, s), 1.49 (2H, m), 1.20 (18H, m), 0.97 (3H, t) .
[실시예 30] 도데칸올-트리(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 (Decanol-Tri(ethylene glycol)-Ethylene glycol-Phosphate)Example 30 Dodecanol-tri (ethylene glycol) -ethylene glycol-phosphate
헥사데칸올 대신에 데칸올 79.1g(500mmol)과 헥산디올 대신에 트리에틸렌 글리콜 37.5g(250mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-트리(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 94g을 얻었다.94 g of dodecanol-tri (ethylene glycol) -ethylene glycol-phosphate was prepared in the same manner as in Example 1 using 79.1 g (500 mmol) of decanol instead of hexadecanol and 37.5 g (250 mmol) of triethylene glycol instead of hexanediol. Got it.
1H NMR (in CHCl3) : 4.23(4H, t), 4.05(2H, t), 3.91(2H, t), 3.75(2H, t) , 3.54 (2H, t), 2.0(1H, s), 1.70(2H, m), 1.22(14H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 4.23 (4H, t), 4.05 (2H, t), 3.91 (2H, t), 3.75 (2H, t), 3.54 (2H, t), 2.0 (1H, s) , 1.70 (2H, m), 1.22 (14H, m), 0.95 (3H, t).
[실시예 31] 도데칸올-트리(에틸렌 글리콜)-프로판올-포스페이트 (Dodecanol-Tri(ethylene glycol)-Propanol-Phosphate)Example 31 Dodecanol-tri (ethylene glycol) -propanol-phosphate (Dodecanol-Tri (ethylene glycol) -Propanol-Phosphate)
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 헥산디올 대신에 트리에 틸렌 글리콜 37.5g(250mmol), 에틸렌 글리콜 대신에 프로판올 66.1g(1100m mol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-트리(에틸렌 글리콜)-프로판올-포스페이트 115g을 얻었다.Dodecanol was used in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol, 37.5 g (250 mmol) of triethylene glycol instead of hexanediol, and 66.1 g (1100 mmol) of propanol instead of ethylene glycol. 115 g of -tri (ethylene glycol) -propanol-phosphate was obtained.
1H NMR (in CHCl3) : 4.20(2H, t), 4.01(4H, t), 3.74(2H, t), 3.56(2H, t), 1.70(4H, m), 1.20(18H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.01 (4H, t), 3.74 (2H, t), 3.56 (2H, t), 1.70 (4H, m), 1.20 (18H, m) , 0.96 (6H, t).
[실시예 32] 도데칸올-트리(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 (Dodecanol-Tri(ethylene glycol)-Ethylene glycol-Phosphate)Example 32 Dodecanol-tri (ethylene glycol) -ethylene glycol-phosphate (Dodecanol-Tri (ethylene glycol) -Ethylene glycol-Phosphate)
헥사데칸올 대신에 도데칸올 93.2g(500mmol)과 헥산디올 대신에 트리에 틸렌 글리콜 37.5g(250mmol)을 사용하여 실시예 1과 같은 방법으로 도데칸올-트리(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 109g을 얻었다.109 g dodecanol-tri (ethylene glycol) -ethylene glycol-phosphate in the same manner as in Example 1, using 93.2 g (500 mmol) of dodecanol instead of hexadecanol and 37.5 g (250 mmol) of triethylene glycol instead of hexanediol Got.
1H NMR (in CHCl3) : 4.22(4H, t), 4.03(2H, t), 3.90(2H, t), 3.73(2H, t) , 3.51(2H, t), 2.0(1H, s), 1.68(2H, m), 1.22(18H, m), 0.95(3H, t). 1 H NMR (in CHCl 3 ): 4.22 (4H, t), 4.03 (2H, t), 3.90 (2H, t), 3.73 (2H, t), 3.51 (2H, t), 2.0 (1H, s) , 1.68 (2H, m), 1.22 (18H, m), 0.95 (3H, t).
[실시예 33] 헥사데칸올-트리(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 (Hexadecanol- Tri(ethylene glycol)-Ethylene glycol-Phosphate)Example 33 Hexadecanol-tri (ethylene glycol) -ethylene glycol-phosphate (Hexadecanol- Tri (ethylene glycol) -Ethylene glycol-Phosphate)
헥산디올 대신에 트리에틸렌 글리콜 37.5g(250mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-트리(에틸렌 글리콜)-에틸렌 글리콜-포스페이트 178g을 얻었다.178 g of hexadecanol-tri (ethylene glycol) -ethylene glycol-phosphate was obtained in the same manner as in Example 1 using 37.5 g (250 mmol) of triethylene glycol instead of hexanediol.
1H NMR (in CHCl3) : 4.22(4H, t), 4.03(2H, t), 3.91(2H, t), 3.73(2H, t), 3.54(2H, t), 2.0(1H, s), 1.66(2H, m), 1.22(26H, m), 0.96(3H, t). 1 H NMR (in CHCl 3 ): 4.22 (4H, t), 4.03 (2H, t), 3.91 (2H, t), 3.73 (2H, t), 3.54 (2H, t), 2.0 (1H, s) , 1.66 (2H, m), 1.22 (26H, m), 0.96 (3H, t).
[실시예 34] 헥사데칸올-트리(에틸렌 글리콜)-프로판올-포스페이트 (Hexadecanol-Tri(ethylene glycol)-Propanol-Phosphate)Example 34 Hexadecanol-tri (ethylene glycol) -propanol-phosphate (Hexadecanol-Tri (ethylene glycol) -Propanol-Phosphate)
헥산디올 대신에 트리에틸렌 글리콜 37.5g(250mmol)과 에틸렌 글리콜 대신에 프로판올 66.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-트리(에틸렌 글리콜)-프로판올-포스페이트 173g을 얻었다.173 g of hexadecanol-tri (ethylene glycol) -propanol-phosphate was obtained in the same manner as in Example 1 using 37.5 g (250 mmol) of triethylene glycol instead of hexanediol and 66.1 g (1100 mmol) of propanol instead of ethylene glycol.
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 3.54(2H, t), 1.70(4H, m), 1.20(26H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 3.54 (2H, t), 1.70 (4H, m), 1.20 (26H, m) , 0.96 (6H, t).
[실시예 35] 헥사데칸올-트리(에틸렌 글리콜)-데칸올-포스페이트 (Hexadecanol- Tri(ethylene glycol)-Decanol-Phosphate)[Example 35] Hexadecanol-tri (ethylene glycol) -decanol-phosphate (Hexadecanol- Tri (ethylene glycol) -Decanol-Phosphate)
헥산디올 대신에 트리에틸렌 글리콜 37.5g(250mmol)과 에틸렌 글리콜 대신에 데칸올 174.1g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-트리(에틸렌 글리콜)-데칸올-포스페이트 192g을 얻었다.192 g of hexadecanol-tri (ethylene glycol) -decanol-phosphate was prepared in the same manner as Example 1 using 37.5 g (250 mmol) of triethylene glycol instead of hexanediol and 174.1 g (1100 mmol) of decanol instead of ethylene glycol. Got it.
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 3.54(2H, t), 1.66(4H, m), 1.20(40H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 3.54 (2H, t), 1.66 (4H, m), 1.20 (40H, m) , 0.96 (6H, t).
[실시예 36] 헥사데칸올-트리(에틸렌 글리콜)-히드록시-포스페이트 (Hexadecanol-Tri(ethylene glycol)-Hydroxy-Phosphate)Example 36 Hexadecanol-tri (ethylene glycol) -hydroxy-phosphate (Hexadecanol-Tri (ethylene glycol) -Hydroxy-Phosphate)
헥산디올 대신에 트리에틸렌 글리콜 37.5g(250mmol)과 에틸렌 글리콜 대신에 물 19.8g(1100mmol)을 사용하여 실시예 1과 같은 방법으로 헥사데칸올-트리(에틸렌 글리콜)-히드록시-포스페이트 91g을 얻었다.91 g of hexadecanol-tri (ethylene glycol) -hydroxy-phosphate was obtained in the same manner as in Example 1, using 37.5 g (250 mmol) of triethylene glycol instead of hexanediol and 19.8 g (1100 mmol) of water instead of ethylene glycol. .
1H NMR (in CHCl3) : 3.70(2H, t), 3.57(6H, m), 1.48(2H, m), 1.22(26H, m), 0.96(3H, t). 1 H NMR (in CHCl 3 ): 3.70 (2H, t), 3.57 (6H, m), 1.48 (2H, m), 1.22 (26H, m), 0.96 (3H, t).
[실시예 37] 헥사데칸올-부탄디올-헥사데칸올-포스페이트(Hexadecanol- Butanediol-Hexadecanol-Phosphate)Example 37 Hexadecanol-Butanediol-Hexadecanol-Phosphate (Hexadecanol-Butanediol-Hexadecanol-Phosphate)
헥사데칸올 242g(1000mmol)과 트리에틸아민 168ml(1200mmol)을 테트라히드로퓨란 600ml에 녹였다. 그리고 포스포릴 클로라이드 46ml(500mmol)를 테트라히드로퓨란 200ml에 녹인 후 4℃에서 천천히 적가한 다음 3시간 동안 교반하여 염을 생성하였다. 교반 반응이 종료되면 생성된 염을 필터하여 제거한 후 농축하면 생성물을 얻었다. 이렇게 얻은 생성물을 500ml의 테트라히드로퓨란에 녹인 후 1,4-부탄디올 22.6g(250mmol)과 트리에틸아민 168ml(1200mmol)을 테트라히드로퓨란 200ml에 녹인 다음 천천히 적가하여 반응이 종료되면 염을 필터하고 컬럼을 통하여 생성물 헥사데칸올-부탄디올-헥사데칸올-포스페이트 214g을 얻었다.242 g (1000 mmol) of hexadecanol and 168 ml (1200 mmol) of triethylamine were dissolved in 600 ml of tetrahydrofuran. And 46 ml (500 mmol) of phosphoryl chloride was dissolved in 200 ml of tetrahydrofuran, and slowly added dropwise at 4 ° C., followed by stirring for 3 hours to form a salt. When the stirring reaction was completed, the resulting salt was filtered off and concentrated to give the product. The resulting product was dissolved in 500 ml of tetrahydrofuran, 22.6 g (250 mmol) of 1,4-butanediol and 168 ml (1200 mmol) of triethylamine were dissolved in 200 ml of tetrahydrofuran, and slowly added dropwise to complete the reaction. 214 g of the product hexadecanol-butanediol-hexadecanol-phosphate were obtained through.
1H NMR (in CHCl3) : 4.03(6H, t), 1.66(6H, m), 1.28(52H, m), 0.92(6H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, t), 1.66 (6H, m), 1.28 (52H, m), 0.92 (6H, t).
[실시예 38] 헥사데칸올-헥산디올-헥사데칸올-포스페이트(Hexadecanol-Hexanediol-Hexadecanol-Phosphate)[Example 38] Hexadecanol-hexanediol-hexadecanol-phosphate (Hexadecanol-Hexanediol-Hexadecanol-Phosphate)
부탄디올 대신에 헥산디올 29.6g (250mmol)을 사용하여 실시예 37과 같은 방법으로 헥사데칸올-헥산디올-헥사데칸올-포스페이트 178g을 얻었다.178 g of hexadecanol-hexanediol-hexadecanol-phosphate was obtained in the same manner as in Example 37, using 29.6 g (250 mmol) of hexanediol instead of butanediol.
1H NMR (in CHCl3) : 4.03(6H, t), 1.66(6H, m), 1.28(54H, m), 0.92(6H, t). 1 H NMR (in CHCl 3 ): 4.03 (6H, t), 1.66 (6H, m), 1.28 (54H, m), 0.92 (6H, t).
[실시예 39] 헥사데칸올-다이(에틸렌 글리콜)-헥사데칸올-포스페이트 (Hexadecanol-Di(ethylene glycol)-Hexadecanol-Phosphate)Example 39 Hexadecanol-di (ethylene glycol) -hexadecanol-phosphate (Hexadecanol-Di (ethylene glycol) -Hexadecanol-Phosphate)
부탄디올 대신에 다이에틸렌 글리콜 26.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 헥사데칸올-다이(에틸렌 글리콜)-헥사데칸올-포스페이트 178g을 얻었다. 178 g of hexadecanol-di (ethylene glycol) -hexadecanol-phosphate was obtained in the same manner as in Example 37 using diethylene glycol 26.5 g (250 mmol) instead of butanediol.
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 1.66(4H, m), 1.22(52H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 1.66 (4H, m), 1.22 (52H, m), 0.95 (6H, t) .
[실시예 40] 헥사데칸올-트리(에틸렌 글리콜)-헥사데칸올-포스페이트 (Hexadecanol-Tri(ethylene glycol)-Hexadecanol-Phosphate)Example 40 Hexadecanol-tri (ethylene glycol) -hexadecanol-phosphate (Hexadecanol-Tri (ethylene glycol) -Hexadecanol-Phosphate)
부탄디올 대신에 트리에틸렌글리콜 37.6g(250mmol)을 사용하여 실시예 37과 같은 방법으로 헥사데칸올-트리(에틸렌 글리콜)-헥사데칸올-포스페이트 205g을 얻었다. 205 g of hexadecanol-tri (ethylene glycol) -hexadecanol-phosphate was obtained in the same manner as in Example 37, using 37.6 g (250 mmol) of triethylene glycol instead of butanediol.
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 3.54(2H, t), 1.66(4H, m), 1.27(52H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 3.54 (2H, t), 1.66 (4H, m), 1.27 (52H, m) , 0.95 (6H, t).
[실시예 41] 도데칸올-헥산디올-도데칸올-포스페이트(Dodecanol-Hexanediol- Dodecanol-Phosphate)Example 41 Dodecanol-Hexanediol-Dodecanol-Phosphate
헥사데칸올 대신에 도데칸올 186.4g(1000mmol)과 부탄디올 대신에 헥산디올 29.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 도데칸올-헥산디올-도데칸올-포스페이트 156g을 얻었다.156 g of dodecanol-hexanediol-dodecanol-phosphate was obtained in the same manner as in Example 37, using 186.4 g (1000 mmol) of dodecanol instead of hexadecanol and 29.5 g (250 mmol) of hexanediol instead of butanediol.
1H NMR (in CHCl3) : 4.05(6H, t), 1.66(6H, m), 1.26(40H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.05 (6H, t), 1.66 (6H, m), 1.26 (40H, m), 0.96 (6H, t).
[실시예 42] 도데칸올-트리(에틸렌 글리콜)-도데칸올-포스페이트 (Dodecanol-Tri(ethylene glycol)-Dodecanol-Phosphate)Example 42 Dodecanol-tri (ethylene glycol) -dodecanol-phosphate (Dodecanol-Tri (ethylene glycol) -Dodecanol-Phosphate)
헥사데칸올 대신에 도데칸올 186.4g(1000mmol)과 부탄디올 대신에 트리에틸렌 글리콜 37.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 도데칸올-트리(에틸렌 글리콜)-도데칸올-포스페이트 165g을 얻었다.165 g of dodecanol-tri (ethylene glycol) -dodecanol-phosphate was obtained in the same manner as in Example 37 using 186.4 g (1000 mmol) of dodecanol instead of hexadecanol and 37.5 g (250 mmol) of triethylene glycol instead of butanediol. .
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 3.54(2H, t), 1.66(4H, m), 1.22(36H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 3.54 (2H, t), 1.66 (4H, m), 1.22 (36H, m) , 0.95 (6H, t).
[실시예 43] 도데칸올-다이(에틸렌 글리콜)-도데칸올-포스페이트 (Dodecanol-Di(ethylene glycol)-Dodecanol-Phosphate)Example 43 Dodecanol-di (ethylene glycol) -dodecanol-phosphate (Dodecanol-Di (ethylene glycol) -Dodecanol-Phosphate)
헥사데칸올 대신에 도데칸올 186.4g(1000mmol)과 부탄디올 대신에 다이에틸 렌 글리콜 26.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 도데칸올-다이(에틸렌 글리콜)-도데칸올-포스페이트 161g을 얻었다. 161 g of dodecanol-di (ethylene glycol) -dodecanol-phosphate was prepared in the same manner as in Example 37, using 186.4 g (1000 mmol) of dodecanol instead of hexadecanol and 26.5 g (250 mmol) of diethylene glycol instead of butanediol. Got it.
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 1.66(4H, m), 1.20(36H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 1.66 (4H, m), 1.20 (36H, m), 0.96 (6H, t) .
[실시예 44] 도데칸올-에틸렌 글리콜-도데칸올-포스페이트 (Dodecanol-ethylene glycol-Dodecanol-Phosphate) Example 44 Dodecanol-Ethylene Glycol-Dodecanol-Phosphate
헥사데칸올 대신에 도데칸올 186.4g(1000mmol)과 부탄디올 대신에 에틸렌 글리콜 15.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 도데칸올-에틸렌 글리콜-도데칸올-포스페이트 101g을 얻었다. Dodecanol-ethylene glycol-dodecanol-phosphate 101g was obtained in the same manner as in Example 37, using 186.4 g (1000 mmol) of dodecanol instead of hexadecanol and 15.5 g (250 mmol) of ethylene glycol instead of butanediol.
1H NMR (in CHCl3) : 4.4(2H, t), 4.03(4H, t), 1.66(4H, m), 1.20(40H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.4 (2H, t), 4.03 (4H, t), 1.66 (4H, m), 1.20 (40H, m), 0.96 (6H, t).
[실시예 45] 데칸올-트리(에틸렌 글리콜)-데칸올-포스페이트 (Decanol-Tri(ethylene glycol)-Decanol-Phosphate)헥사데칸올 대신에 데칸올 158.3g(1000mmol)과 부탄디올 대신에 트리에 틸렌 글리콜 37.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 데칸올-트리(에틸렌 글리콜)-데칸올-포스페이트 134g을 얻었다. Example 45 Decaneol-Tri (ethylene glycol) -Decanol-Phosphate (Decanol-Tri (ethylene glycol) -Decanol-Phosphate) Instead of hexadecanol 158.3 g (1000 mmol) and triethylene instead of butanediol 134 g of decanol-tri (ethylene glycol) -decanol-phosphate was obtained in the same manner as in Example 37 using 37.5 g (250 mmol) of glycol.
1H NMR (in CHCl3) : 4.21(2H, t), 4.01(4H, t), 3.76(2H, t), 3.56(2H, t), 1.66(4H, m), 1.22(28H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.21 (2H, t), 4.01 (4H, t), 3.76 (2H, t), 3.56 (2H, t), 1.66 (4H, m), 1.22 (28H, m) , 0.95 (6H, t).
[실시예 46] 데칸올-다이(에틸렌 글리콜)-데칸올-포스페이트 (Decanol-Di(ethylene glycol)-Decanol-Phosphate) Example 46 Decanol-di (ethylene glycol) -decanol-phosphate (Decanol-Di (ethylene glycol) -Decanol-Phosphate)
헥사데칸올 대신에 데칸올 153.8g(1000mmol)과 부탄디올 대신에 다이에 틸렌 글리콜 26.5g(250mmol)을 사용하여 실시예 37과 같은 방법으로 데칸올-다이(에틸렌 글리콜)-데칸올-포스페이트 105g을 얻었다. 105 g of decanol-di (ethylene glycol) -decanol-phosphate was prepared in the same manner as in Example 37 using 153.8 g (1000 mmol) of decanol instead of hexadecanol and 26.5 g (250 mmol) of diethylene glycol instead of butanediol. Got it.
1H NMR (in CHCl3) : 4.20(2H, t), 4.03(4H, t), 3.74(2H, t), 1.66(4H, m), 1.20(28H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.20 (2H, t), 4.03 (4H, t), 3.74 (2H, t), 1.66 (4H, m), 1.20 (28H, m), 0.96 (6H, t) .
[실시예 47] 데칸올-헥산디올-데칸올-포스페이트 (Decanol-Hexanediol-Decanol-Phosphate) Example 47 Decanol-Hexanediol-Decanol-Phosphate
헥사데칸올 대신에 데칸올 153.8g(1000mmol)과 부탄디올 대신에 헥산디올 29.5(250mmol)을 사용하여 실시예 37과 같은 방법으로 데칸올-헥산디올-데칸올-포스페이트 204g을 얻었다.204 g of decanol-hexanediol-decanol-phosphate was obtained in the same manner as in Example 37 using 153.8 g (1000 mmol) of decanol instead of hexadecanol and 29.5 (250 mmol) of hexanediol instead of butanediol.
1H NMR (in CHCl3) : 4.02(6H, t), 1.66(6H, m), 1.22(30H, m), 0.95(6H, t). 1 H NMR (in CHCl 3 ): 4.02 (6H, t), 1.66 (6H, m), 1.22 (30H, m), 0.95 (6H, t).
[실시예 48] 데칸올-옥탄디올-데칸올-포스페이트 (Decanol-Octanediol-Decanol-Phosphate)Example 48 Decantol-Octanediol-Decanol-Phosphate
헥사데칸올 대신에 데칸올 153.8g(1000mmol)과 부탄디올 대신에 옥탄디올 36.6(250mmol)을 사용하여 실시예 37과 같은 방법으로 데칸올-옥탄디올-데칸올-포스페이트 179g을 얻었다.179 g of decanol-octanediol-decanol-phosphate was obtained in the same manner as in Example 37, using 153.8 g (1000 mmol) of decanol instead of hexadecanol and 36.6 (250 mmol) of octanediol instead of butanediol.
1H NMR (in CHCl3) : 4.02(6H, t), 1.66(6H, m), 1.28(32H, m), 0.96(6H, t). 1 H NMR (in CHCl 3 ): 4.02 (6H, t), 1.66 (6H, m), 1.28 (32H, m), 0.96 (6H, t).
[시험예 1] 손상피부의 회복력 시험Test Example 1 Recovery of Damaged Skin
상기 실시예에 제조한 화합물에 대하여 피부 회복 효과를 비교하였다. 피부의 회복 효과는 탈모 기니아 돼지(Hairless Guinea Pig) 35 마리를 7개조로 나누고 상기 실시예에서 제조한 화합물들을 각 조로 나누어 측정하였다. 시험 방법은 하기와 같았다. 핀(Finn) 챔버를 이용하여 아세톤으로 30분간 시험동물들의 옆구리에 패취하여 피부장벽을 손상시킨 다음, 패취한 자리에 시험물질을 각각 200㎕씩 도포하였다. 손상된 피부장벽의 회복은 증발량 측정기(Evaporimeter)를 이용하여 각질층을 통한 수분 손실(Transepidermal Water Loss, TEWL)을 측정하여 평가하였다. 기기 측정은 아세톤 패취 전, 패취 제거 후 30분, 1시간, 2시간, 4시간, 6시간 및 8시간에 측정하였다. 그 결과는 하기 표 1에 나타내었다. 아세톤 처리전의 정상 피부의 측정치를 0으로 하였으며, 아세톤 처치직후의 값을 100으로 하여 피부가 점차 정상상태로 회복되는 것을 관찰하였다. 하기 표 1의 결과에서 보는 바와 같이 포스페이트 유도체는 vehicle에 비하여 손상된 피부의 현저한 회복능력을 보였으며, 천연 세라미드와 유사한 회복능력을 보였다.The skin repair effect was compared with respect to the compound prepared in the above example. The recovery effect of the skin was measured by dividing 35 hairless guinea pigs into seven groups and the compounds prepared in the above examples by dividing into groups. The test method was as follows. Using a Finn chamber, the skin of the test animals was patched with acetone for 30 minutes to damage the skin barrier, and then 200 μl of test substance was applied to each patch. The recovery of damaged skin barrier was assessed by measuring the Transepidermal Water Loss (TEWL) through the stratum corneum using an evaporimeter. Instrument measurements were taken at 30 minutes, 1 hour, 2 hours, 4 hours, 6 hours and 8 hours before acetone patching and after patch removal. The results are shown in Table 1 below. The measured value of normal skin before acetone treatment was 0, and the value immediately after the acetone treatment was 100, and the skin gradually recovered to a normal state. As shown in the results of Table 1, the phosphate derivative showed a remarkable recovery ability of the damaged skin compared to the vehicle, and showed a recovery ability similar to that of natural ceramide.
[시험예 2] 피부내 수분량 증가 측정 실험[Test Example 2] Measurement experiment of increase in water content
상기 실시예에서 제조한 화합물에 대하여 피부내 수분량 증가 정도를 비교하였다. 피부내 수분량 증가 측정 실험은 탈모 기니아 돼지(Hairless Guinea Pig) 35마리를 7개조로 나누고 상기 실시예에 나타난 화합물을 각 조에 나누어 측정하였다. 시험 방법은 하기와 같았다. 핀(Finn) 챔버를 이용하여 아세톤으로 30분간 시험동물들의 옆구리에 패취하여 피부장벽을 손상시킨 다음, 패취한 자리에 시험물질을 각각 200㎕씩 도포하였으며 수분량 측정기(Corneummeter)를 이용하여 각질층의 수분량을 측정하여 평가하였다. 기기 측정은 아세톤 패취 제거 직후 및 패취 제거 후 6시간, 12시간, 18시간 및 24시간에 측정하였다. 그 결과는 하기 표 2에 나타내었다. 아세톤 처리 직후의 값을 100으로 하여 피부내의 수분량의 변화를 관찰하였다. 하기 표2의 결과에서 보는 바와 같이 포스페이트 유도체는 vehicle에 비하여 피부내의 수분량을 증가시키는 효과를 보였으며, 글리세롤과도 유사한 능력을 보였다.The increase in the amount of water in the skin was compared with respect to the compound prepared in Example. In the skin moisture measurement test, 35 hairless guinea pigs were divided into seven groups, and the compounds shown in the above examples were divided into groups. The test method was as follows. Using a Finn chamber, a patch of acetone was applied to the flanks of the test animals for 30 minutes to damage the skin barrier. Then, 200 μl of test substance was applied to the patch, and the moisture level of the stratum corneum was measured using a corneummeter. Was measured and evaluated. Instrument measurements were taken immediately after acetone patch removal and at 6 hours, 12 hours, 18 hours and 24 hours after patch removal. The results are shown in Table 2 below. The change in the amount of water in the skin was observed by setting the value immediately after the acetone treatment to 100. As shown in the results of Table 2, the phosphate derivative showed an effect of increasing the amount of water in the skin compared to the vehicle, and showed a similar ability to glycerol.
[시험예 3] 수분유지력 측정 실험[Test Example 3] Moisture retention test
상기 실시예에서 제조한 화합물에 대하여 수분유지력을 측정하였다. 수분 유지력 측정 실험은 상기 실시예에 나타난 화합물에 수분함유량이 60%가 되게끔 시료를 제조하고 시료를 항온항습실(40℃, 상대습도 25%)에 보관하면서 시간에 따른 무게변화를 측정하여 수분 함유량의 변화를 관찰하고 이로써 화합물의 수분 유지력을 평가하였다. 그 결과는 하기 표 3에 나타내었다. 하기 표 3의 결과에서 보는 바와 같이 포스페이트 유도체는 vehicle이나 글리세롤에 비하여 높은 수분 유지력을 보 였다.Moisture retention was measured for the compound prepared in Example. Moisture retention test is to prepare a sample so that the moisture content in the compound shown in the above example to 60%, and store the sample in a constant temperature and humidity room (40 ℃, 25% relative humidity) while measuring the weight change over time to determine the moisture content Was observed to evaluate the water retention of the compound. The results are shown in Table 3 below. As shown in the results in Table 3, the phosphate derivative showed a higher moisture retention than the vehicle or glycerol.
[시험예 4] 액정 베이스의 액정 형성능 측정 실험[Test Example 4] Measurement experiment of liquid crystal formation ability of the liquid crystal base
상기의 제조예 1∼48의 액정베이스를 편광현미경을 통하여 액정 형성여부를 관측해 보았다. 대부분의 화합물에서 라멜라 액정의 편광결과 같은 액정을 관찰할 수 있었다. 그 결과 중 대표적인 것을 도 1에 나타내었다.The liquid crystal bases of the above Production Examples 1 to 48 were observed for liquid crystal formation through a polarizing microscope. In most compounds, liquid crystals such as polarization results of lamellar liquid crystals were observed. Typical results are shown in FIG. 1.
이상의 실시예 및 시험예에서 볼 수 있는 바와 같이, 본 발명에 의해 제공되는 화학식 1의 포스페이트 유도체 및 이를 포함하는 액정 베이스를 사용하면 높은 보습력과 더불어 높은 보습 지속력를 보이는 화장료를 제공할 수 있었다.
As can be seen in the above examples and test examples, the use of the phosphate derivative of Formula 1 provided by the present invention and the liquid crystal base including the same could provide a cosmetic having high moisturizing power and high moisturizing sustainability.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0589473A1 (en) * | 1992-09-25 | 1994-03-30 | E.R. SQUIBB & SONS, INC. | Hydroxyphosphinyl phosphonate squalene synthetase inhibitors and their use in pharmaceutical compositions |
| US5919967A (en) * | 1997-04-11 | 1999-07-06 | Epix Medical, Inc. | Process for synthesizing phosphodiesters |
| US6388120B1 (en) * | 1998-02-13 | 2002-05-14 | Pabu Services, Inc. | Continuous process for the manufacture of phosphoric acid esters |
| US6583315B2 (en) * | 2000-12-23 | 2003-06-24 | Clariant Gmbh | Process for preparing ethanebis(alkylphosphinic) acids |
| EP1454941A1 (en) * | 2003-03-04 | 2004-09-08 | Clariant GmbH | Modified polyethylenephosphinic acids and the salts thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0589473A1 (en) * | 1992-09-25 | 1994-03-30 | E.R. SQUIBB & SONS, INC. | Hydroxyphosphinyl phosphonate squalene synthetase inhibitors and their use in pharmaceutical compositions |
| US5919967A (en) * | 1997-04-11 | 1999-07-06 | Epix Medical, Inc. | Process for synthesizing phosphodiesters |
| US6388120B1 (en) * | 1998-02-13 | 2002-05-14 | Pabu Services, Inc. | Continuous process for the manufacture of phosphoric acid esters |
| US6583315B2 (en) * | 2000-12-23 | 2003-06-24 | Clariant Gmbh | Process for preparing ethanebis(alkylphosphinic) acids |
| EP1454941A1 (en) * | 2003-03-04 | 2004-09-08 | Clariant GmbH | Modified polyethylenephosphinic acids and the salts thereof |
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