CN118317764A - Composition and cellulose derivative - Google Patents
Composition and cellulose derivative Download PDFInfo
- Publication number
- CN118317764A CN118317764A CN202280078527.9A CN202280078527A CN118317764A CN 118317764 A CN118317764 A CN 118317764A CN 202280078527 A CN202280078527 A CN 202280078527A CN 118317764 A CN118317764 A CN 118317764A
- Authority
- CN
- China
- Prior art keywords
- cellulose
- monovalent organic
- group
- cellulose derivative
- organic group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229920002678 cellulose Polymers 0.000 title claims abstract description 281
- 239000001913 cellulose Substances 0.000 title claims abstract description 280
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 125000000962 organic group Chemical group 0.000 claims abstract description 142
- 239000003921 oil Substances 0.000 claims abstract description 103
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 77
- 238000006467 substitution reaction Methods 0.000 claims abstract description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 27
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 239000010696 ester oil Substances 0.000 claims abstract description 24
- 229920002545 silicone oil Polymers 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 41
- 239000002537 cosmetic Substances 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 19
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- 239000008041 oiling agent Substances 0.000 claims description 3
- 235000010980 cellulose Nutrition 0.000 description 256
- 235000019198 oils Nutrition 0.000 description 95
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000008186 active pharmaceutical agent Substances 0.000 description 31
- -1 hydroxypropyl Chemical group 0.000 description 21
- 125000002252 acyl group Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 18
- 239000000499 gel Substances 0.000 description 17
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 16
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000002608 ionic liquid Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000009825 accumulation Methods 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229920002301 cellulose acetate Polymers 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 210000004209 hair Anatomy 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ZQZUENMXBZVXIZ-UHFFFAOYSA-N ethenyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC=C ZQZUENMXBZVXIZ-UHFFFAOYSA-N 0.000 description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000516 sunscreening agent Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- WAYINTBTZWQNSN-UHFFFAOYSA-N 11-methyldodecyl 3,5,5-trimethylhexanoate Chemical compound CC(C)CCCCCCCCCCOC(=O)CC(C)CC(C)(C)C WAYINTBTZWQNSN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- SPTSIOTYTJZTOG-UHFFFAOYSA-N acetic acid;octadecanoic acid Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O SPTSIOTYTJZTOG-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000012377 drug delivery Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000346 nonvolatile oil Substances 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000000475 sunscreen effect Effects 0.000 description 3
- 230000002522 swelling effect Effects 0.000 description 3
- 150000007970 thio esters Chemical class 0.000 description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000875 Dissolving pulp Polymers 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 description 2
- IIOPVJIGEATDBS-UHFFFAOYSA-N acetic acid;dodecanoic acid Chemical compound CC(O)=O.CCCCCCCCCCCC(O)=O IIOPVJIGEATDBS-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000006480 benzoylation reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 2
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BJDAUCLANVMIOB-UHFFFAOYSA-N (3-decanoyloxy-2,2-dimethylpropyl) decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)(C)COC(=O)CCCCCCCCC BJDAUCLANVMIOB-UHFFFAOYSA-N 0.000 description 1
- VIKMHHCQBWIVLV-UHFFFAOYSA-N 1,2,3-trimethyl-2h-imidazole Chemical compound CC1N(C)C=CN1C VIKMHHCQBWIVLV-UHFFFAOYSA-N 0.000 description 1
- ALSIFQIAIHCPAA-UHFFFAOYSA-N 1,2-dimethyl-3-propyl-2h-imidazole Chemical compound CCCN1C=CN(C)C1C ALSIFQIAIHCPAA-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- TYOCDPIZUIQUSO-UHFFFAOYSA-N 1-butyl-2,3-dimethyl-2h-imidazole Chemical compound CCCCN1C=CN(C)C1C TYOCDPIZUIQUSO-UHFFFAOYSA-N 0.000 description 1
- LASRFGOBZGDHSR-UHFFFAOYSA-N 1-butyl-2,4-dimethyl-2H-pyridine Chemical compound C(CCC)N1C(C=C(C=C1)C)C LASRFGOBZGDHSR-UHFFFAOYSA-N 0.000 description 1
- GDCCFQMGFUZVKK-UHFFFAOYSA-N 1-butyl-2h-pyridine Chemical compound CCCCN1CC=CC=C1 GDCCFQMGFUZVKK-UHFFFAOYSA-N 0.000 description 1
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 description 1
- CDXLWOUTFCMPDM-UHFFFAOYSA-N 1-butyl-4-methyl-2h-pyridine Chemical compound CCCCN1CC=C(C)C=C1 CDXLWOUTFCMPDM-UHFFFAOYSA-N 0.000 description 1
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 1
- JFYZBXKLRPWSGV-UHFFFAOYSA-N 1-methyl-3-propyl-2h-imidazole Chemical compound CCCN1CN(C)C=C1 JFYZBXKLRPWSGV-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VRBHTEGUHVNKEA-UHFFFAOYSA-N 16-methylheptadecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC(C)C VRBHTEGUHVNKEA-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- YHBWXWLDOKIVCJ-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]acetic acid Chemical compound COCCOCCOCC(O)=O YHBWXWLDOKIVCJ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- ZDHRAACDPXUCHC-UHFFFAOYSA-N 3,4-diethyl-2-hexoxyphenol;5-methoxy-4-phenyltriazine Chemical compound COC1=CN=NN=C1C1=CC=CC=C1.CCCCCCOC1=C(O)C=CC(CC)=C1CC ZDHRAACDPXUCHC-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YYJDNPBBSWDQNF-UHFFFAOYSA-N C(C)C([N+](CCOC)(C)C)CC Chemical compound C(C)C([N+](CCOC)(C)C)CC YYJDNPBBSWDQNF-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- GSBKRFGXEJLVMI-UHFFFAOYSA-N Nervonyl carnitine Chemical compound CCC[N+](C)(C)C GSBKRFGXEJLVMI-UHFFFAOYSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- HQRJTRSKPWEIII-OCANKYAHSA-N icosan-9-yl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCC\C=C/C[C@H](O)CCCCCC HQRJTRSKPWEIII-OCANKYAHSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000004806 packaging method and process Methods 0.000 description 1
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- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000002304 perfume Substances 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- SCRSFLUHMDMRFP-UHFFFAOYSA-N trimethyl-(methyl-octyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C SCRSFLUHMDMRFP-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Abstract
The present invention provides a cellulose derivative having excellent affinity for various oils and a composition comprising the cellulose derivative. The composition comprises a cellulose derivative having a monovalent organic group (L a) having a hydrocarbon group of 6 or more carbon atoms at the terminal and having no ether bond, wherein at least a part of hydrogen atoms constituting a hydroxyl group in cellulose is substituted, and an oil agent, and the average substitution degree of the monovalent organic group (L a) is 1.1 or more. The oil is preferably at least one selected from hydrocarbon oil, ester oil and silicone oil.
Description
Technical Field
The present disclosure relates to compositions and cellulose derivatives. More specifically, the present disclosure relates to compositions comprising cellulose derivatives and an oil, and cellulose derivatives. The present application claims the priority of japanese patent application nos. 2021-193177 of japanese patent application No. 11/month 29 and of japanese patent application nos. 2021-196936 of japanese patent application No. 12/month 3 of 2021, the contents of which are incorporated herein by reference.
Background
Cellulose is a polymer compound in which a large number of glucose units (glucopyranose units) are polymerized through β -1, 4-glycosidic bonds. At present, cellulose and its derivatives have been widely used for applications such as application to skin of paper, cosmetics, and the like, and for applications such as coating agents, paints, film forming agents, and the like.
For example, patent documents 1 and 2 disclose cosmetics containing specific cellulose derivatives. Patent document 3 discloses an external preparation for skin containing a specific cellulose derivative. Patent document 4 discloses a film forming agent containing a specific cellulose derivative.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2017-105757
Patent document 2: japanese patent laid-open No. 2007-527861
Patent document 3: japanese patent laid-open No. 8-175929
Patent document 4: japanese patent laid-open publication No. 2014-12852
Disclosure of Invention
Problems to be solved by the invention
It is important that cellulose and its derivatives have excellent affinity with solvents, such as solubility in solvents, swelling properties and dispersibility, when used as components and materials of products. However, the cosmetic of patent document 1 is required to use a solvent obtained by mixing a hydrocarbon oil and an ester oil in a specific ratio as an oil agent from the viewpoint of excellent film formability, and does not disclose or teach the use of only a hydrocarbon oil or only an ester oil as an oil agent. The cosmetic composition disclosed in patent document 2 contains a nonvolatile oil such as wax and wax oil, and does not investigate the solubility and swelling properties of a cellulose derivative in a volatile oil alone. The nonvolatile oil agent also remains in the form of a film together with the cellulose derivative after coating, and thus high affinity is not necessarily required. Patent document 3 discloses only an emulsified skin external preparation. Patent document 4 only discusses solubility of cellulose ester in acetone as an organic solvent, but does not discuss solubility in an oil solution.
As described above, patent documents 1 to 4 disclose only a method using emulsification or acetone instead of an oil agent, a method using a nonvolatile oil agent or a specific mixed solvent as an oil agent, and the range of the oil agent that can be used is limited for a composition containing a cellulose derivative. For this reason, a composition containing a cellulose derivative and capable of using various oils is required.
Accordingly, an object of the present disclosure is to provide cellulose derivatives having excellent affinity for various oils, and compositions containing the cellulose derivatives.
Means for solving the problems
As a result of intensive studies to solve the above problems, the inventors of the present disclosure have found that specific cellulose derivatives have excellent affinity for various oils. The present disclosure has been completed based on these findings.
That is, the present disclosure provides a composition comprising a cellulose derivative having a monovalent organic group (La) that replaces at least a part of hydrogen atoms constituting a hydroxyl group in cellulose, a hydrocarbon group having 6 or more carbon atoms at the terminal, and no ether bond, and an oil agent, wherein the average substitution degree of the monovalent organic group (L a) is 1.1 or more.
The oil is preferably at least one selected from hydrocarbon oil, ester oil and silicone oil.
The content of the hydrocarbon oil is preferably more than 80 mass%.
The content of the ester oil is preferably more than 50 mass%.
The cellulose derivative preferably has a monovalent organic group (L c) having 5 or less carbon atoms, wherein the monovalent organic group (L c) has a hydrocarbon group at the terminal and no ether bond, in place of at least a part of hydrogen atoms constituting the hydroxyl group in the cellulose.
In the cellulose derivative, the average substitution degree of the monovalent organic group (L a) is preferably equal to or higher than the average substitution degree of the monovalent organic group (L c).
In the cellulose derivative, the average substitution degree of the monovalent organic group (L c) is preferably 1.0 or less.
The monovalent organic group (L a) is preferably a group represented by the following formula (1).
-X1-R1(1)
[ Wherein R 1 represents the above-mentioned hydrocarbon group having 6 or more carbon atoms, and X 1 represents a group which is directly bonded or can be bonded to an oxygen atom constituting a hydroxyl group in the above-mentioned cellulose to form a linking group. The leftwardly extending bonding arm is bonded to an oxygen atom in the cellulose backbone ].
The composition is preferably used for oily cosmetics.
The present disclosure also provides a cellulose derivative comprising a monovalent organic group (L b) in which at least a part of hydrogen atoms constituting hydroxyl groups in cellulose are replaced with the monovalent organic group (L b), and a group represented by the following formula (2) is present at the terminal.
-O-R2(2)
[ Wherein R 2 represents a hydrocarbon group having 6 or less carbon atoms ].
The monovalent organic group (L b) preferably contains 2 or more ether linkages.
The monovalent organic group (L b) is preferably bonded to the cellulose skeleton via an ester bond having an oxygen atom constituting the hydroxyl group as a constituent atom.
The monovalent organic group (L b) preferably comprises a (poly) oxyalkylene chain.
The cellulose derivative preferably has a monovalent organic group (L a) which replaces at least a part of hydrogen atoms constituting a hydroxyl group in the cellulose, has a hydrocarbon group having 6 or more carbon atoms at the terminal, and has no ether bond.
The average degree of substitution of the monovalent organic group (L a) is preferably greater than the average degree of substitution of the monovalent organic group (L b).
In addition, the present disclosure provides a composition, and comprises the cellulose derivative and an oil agent.
In addition, the present disclosure provides an oily cosmetic comprising the above composition.
ADVANTAGEOUS EFFECTS OF INVENTION
The composition of the present disclosure is excellent in affinity of cellulose derivatives for oils even in the case of using various oils. Therefore, even when the content ratio of the hydrocarbon oil or the ester oil is high, for example, the cellulose derivative tends to be excellent in solubility and swelling properties and film formability (film formability).
Drawings
FIG. 1 is a diagram showing 1 H-NMR of a cellulose derivative produced in example 9.
Detailed Description
[ Composition ]
The composition of the present disclosure comprises at least a cellulose derivative and an oil. The cellulose derivative has at least a monovalent organic group having a hydrocarbon group having 6 or more carbon atoms at the terminal and having no ether bond, wherein at least a part of hydrogen atoms constituting a hydroxyl group in cellulose is substituted, and the average substitution degree of the monovalent organic group is 1.1 or more.
In the present specification, "cellulose" means a carbohydrate (polysaccharide) represented by the formula (C 6H10O5) n, that is, cellulose. For example, the cellulose does not contain a substituent substituted on the cellulose such as hydroxypropyl in hydroxypropyl Cellulose (CAP), hydroxyethyl in hydroxyethyl cellulose (HEC), or acyl in Cellulose Acetate Butyrate (CAB). Specifically, the cellulose derivative is a bond of a repeating unit represented by the following formula (a). For the cellulose derivative of the present disclosure, in the above formula (a), 1 or more of the 3 groups bonded to an oxygen atom (i.e., groups bonded by bonding arms extending from 3 oxygen atoms) are monovalent organic groups (L a) or monovalent organic groups (L b). In the present specification, the "cellulose skeleton" refers to a group other than a group bonded to an oxygen atom derived from a hydroxyl group in cellulose.
[ Chemical formula 1]
In the present specification, the monovalent organic group having a hydrocarbon group having 6 or more carbon atoms at the terminal and having no ether bond may be referred to as "monovalent organic group (L a)".
The monovalent organic group (L a) may replace a hydrogen atom of any of 3 hydroxyl groups in a glucose unit in cellulose. That is, the monovalent organic group (L a) may be bonded to an oxygen atom of any of 3 hydroxyl groups in the glucose unit in cellulose. The cellulose derivative (a) may have only one monovalent organic group (L a) or two or more monovalent organic groups (L a).
The monovalent organic group (L a) has a hydrocarbon group having 6 or more carbon atoms at the terminal. By having such monovalent organic groups (L a), the cellulose derivative (a) is excellent in affinity for various oils. The number of carbon atoms in the hydrocarbon group is preferably 7 or more, more preferably 10 or more, and still more preferably 12 or more. The number of carbon atoms in the hydrocarbon group is preferably 24 or less, more preferably 18 or less. When the number of carbon atoms is 24 or less, entanglement of monovalent organic groups (L a) is suppressed, and the affinity for oils is more excellent.
The hydrocarbon group at the terminal of the monovalent organic group (L a) may be linear or branched, and preferably has 6 or more carbon atoms. The hydrocarbon group may be any hydrocarbon group of a saturated hydrocarbon group or an unsaturated hydrocarbon group.
Examples of the hydrocarbon group include: hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl, dodecyl, lauryl, tridecyl, tetradecyl, myristyl, pentadecyl, myristyl, heptadecyl, stearyl, oleyl, and the like.
The monovalent organic group (L a) has no ether linkage (-O-). The oxygen atom in the hydroxyl group in cellulose, i.e., the oxygen atom that bonds the monovalent organic group (L a) to the cellulose skeleton, is not included in the monovalent organic group (L a). Accordingly, the monovalent organic group (L a) may be bonded to the cellulose skeleton via an ether bond having an oxygen atom constituting a hydroxyl group in cellulose as a constituting atom. In addition, for example, a group in which an organic group is substituted with a hydroxyl group in the hydroxypropyl group in CAP through an ether bond, has an ether bond derived from the hydroxypropyl group in a portion not included in the cellulose skeleton, and therefore does not belong to a monovalent organic group (L a).
The monovalent organic group (L a) is directly bonded to an oxygen atom constituting a hydroxyl group in cellulose, or bonded together via a linking group having the above oxygen atom (oxygen atom in cellulose skeleton) as a constituting atom. The linking group is formed by the oxygen atom and a monovalent organic group (L a). Examples of the linking group include: ether linkages, ester linkages, urethane linkages, phosphonic acid groups, thioester linkages, and the like. Among them, ester bonds are preferable from the viewpoint of easy introduction.
The monovalent organic group (L a) is preferably a group represented by the following formula (1).
-X1-R1(1)
[ Wherein R 1 represents the above-mentioned hydrocarbon group having 6 or more carbon atoms, and X 1 represents a group which is directly bonded or can be bonded to an oxygen atom constituting a hydroxyl group in cellulose to form a linking group. Bonding arms extending to the left to oxygen atoms in the cellulose skeleton
Examples of the linking group that X 1 can form include the above-mentioned groups. As X 1, for example, there may be mentioned: direct bonding, carbonyl (-C (=o) -), amido (-C (=o) -N (-R) -), (-P (=o) (-R) -) thiocarbonyl (-C (=s) -) and the like. R is a hydrogen atom or a monovalent organic group. As X 1, a carbonyl group is preferable. That is, the monovalent organic group (L a) is preferably an acyl group.
In the cellulose derivative (a), the average substitution degree (DS a) of the monovalent organic group (L a) is 1.1 or more, preferably 1.4 or more, more preferably 1.7 or more, still more preferably 2.0 or more, particularly preferably 2.2 or more. When DS a is 1.1 or more, the cellulose derivative (A) has excellent affinity for various oils. DS a is 3.0 or less, preferably 2.9 or less, and may be 2.8 or less, 2.7 or less. When DS a is 2.9 or less, for example, a monovalent organic group (L b) described later can be introduced, and the cellulose derivative has a more excellent affinity for oils.
The average substitution degree in the present specification is the number of groups (average value) per unit of the repeating unit represented by the above formula (a) in the cellulose derivative. In the present specification, the average substitution degree may be determined by a known or conventional method, and for example, analysis/determination may be performed by 1H-NMR、13 C-NMR. Specifically, the integral ratio of the proton in the cellulose skeleton to the proton of the terminal methyl group of the hydrocarbon group having 6 or more carbon atoms in the monovalent organic group (L a) can be calculated. In addition, in the case where a peak of a monovalent organic group included in the cellulose derivative overlaps with a peak derived from the cellulose skeleton in the NMR spectrum, 1 H-NMR analysis may be performed on the cellulose derivative obtained by completely benzoylating the residual hydroxyl groups included in the cellulose skeleton in the cellulose derivative, and the calculation may be performed based on the integral ratio of the characteristic peaks, with the average substituent including the total of benzoyl groups being 3.0.
The total number of carbon atoms in the monovalent organic group (L a) is preferably 6 to 30, more preferably 7 to 20. When the total number of carbon atoms is within the above range, the cellulose derivative is more excellent in affinity for an oil agent.
The cellulose derivative (a) may have a monovalent organic group (L b) substituted for at least a part of hydrogen atoms constituting a hydroxyl group in cellulose, and the monovalent organic group (L b) may have a group represented by the following formula (2) at the terminal. When the monovalent organic group (L b) is provided, accumulation (packing) of cellulose derivatives in the oil due to its flexibility is suppressed, and the affinity for the oil is more excellent.
-O-R2(2)
[ Wherein R 2 represents a hydrocarbon group having 6 or less carbon atoms ]
R 2 is a hydrocarbon group having 6 or less carbon atoms. The number of carbon atoms in the hydrocarbon group is preferably 4 or less, more preferably 2 or less. Examples of the hydrocarbon group include: methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl.
The hydrocarbon group having a monovalent organic group (L b) at the terminal may be linear or branched. The hydrocarbon group may be any hydrocarbon group of a saturated hydrocarbon group or an unsaturated hydrocarbon group.
The total number of carbon atoms in the monovalent organic group (L b) is preferably 1 to 20, more preferably 2 to 15. When the total number of carbon atoms is within the above range, the accumulation of cellulose derivatives is further suppressed.
The monovalent organic group (L b) preferably comprises a (poly) oxyalkylene chain. In this case, the accumulation of the cellulose derivative is further suppressed. The alkylene group in the (poly) oxyalkylene chain is preferably a divalent hydrocarbon group having 1 to 6 carbon atoms (more preferably 2 to 4 carbon atoms). Examples of the alkylene group include: methylene, ethylene, propylene, trimethylene, tetramethylene, and the like.
The average polymerization degree of the oxyalkylene groups in the (poly) oxyalkylene chain is preferably 1 to 5, more preferably 2 to 3. When the average polymerization degree is within the above range, the accumulation of the cellulose derivative is further suppressed.
The monovalent organic group (L b) has at least 1 ether bond, preferably 2 or more. The number of the ether bonds is preferably 6 or less, more preferably 4 or less. When the average polymerization degree is within the above range, the accumulation of the cellulose derivative is further suppressed.
The monovalent organic group (L b) is directly bonded to an oxygen atom in the cellulose skeleton or bonded to the cellulose skeleton via a linking group having the oxygen atom as a constituent atom. The linking group is formed of the oxygen atom and a monovalent organic group (L b). Examples of the linking group include: ether linkages, ester linkages, urethane linkages, phosphonic acid groups, thioester linkages, and the like. Among them, ester bonds are preferable from the viewpoint of easy introduction.
The monovalent organic group (L b) is particularly preferably a group represented by the following formula (3).
-X2-R4(-O-R3)n-O-R2(3)
[ Wherein R 2 is the same as described above. R 3 represents an alkylene group, n represents the degree of polymerization (-O-R 3), R 4 represents a directly bonded or divalent organic group, and X 2 represents a group capable of bonding to an oxygen atom constituting a hydroxyl group in cellulose to form a linking group. The leftwardly extending bonding arm bonds to an oxygen atom in the cellulose backbone. ]
(-O-R 3) n represents the above-mentioned (poly) oxyalkylene chain. R 3 represents an alkylene group, and examples of the alkylene group include those already described and illustrated. n represents a natural number, preferably 1 to 5, more preferably 2 to 3.
R 4 is a direct bond or a divalent organic group. The divalent organic group is preferably a divalent hydrocarbon group. The divalent hydrocarbon group may be any hydrocarbon group of a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be any hydrocarbon group of a straight chain or a branched chain. The number of carbon atoms of the divalent hydrocarbon group is preferably 1 to 8. The divalent hydrocarbon group is preferably an alkylene group such as a methylene group, an ethylene group, a propylene group, a trimethylene group, or a tetramethylene group.
Examples of the linking group that can be formed by X 2 include those exemplified and described as the linking group that can be formed by X 1 described above. As X 2, for example, there may be mentioned: carbonyl (-C (=o) -), amido (-C (=o) -N (-R) -), (-P (=o) (-R) -) thiocarbonyl (-C (=s) -) and the like. R is a hydrogen atom or a monovalent organic group. Among them, carbonyl is preferable.
In the cellulose derivative (a), the average substitution degree (DS b) of the monovalent organic group (L b) is preferably 0.1 or more, more preferably 0.5 or more, and further preferably 1.0 or more. When DS b is 0.1 or more, the accumulation of cellulose derivatives is further suppressed. The DS b is preferably 1.9 or less, more preferably 1.5 or less, and further preferably 1.3 or less.
In the cellulose derivative (a), the average degree of substitution of the monovalent organic group (L a) is preferably equal to or higher than the average degree of substitution of the monovalent organic group (L b), and more preferably higher than the average degree of substitution of the monovalent organic group (L b). The difference [ DS a-DSb ] between the average degree of substitution (DS a) of the monovalent organic group (L a) and the average degree of substitution (DS c) of the monovalent organic group (L b) is preferably 0.1 to 2.5, more preferably 0.4 to 2.0, and even more preferably 0.4 to 1.0. When the difference is within the above range, the affinity for the oil agent is more excellent.
The ratio [ DS a/DSb ] of the average degree of substitution (DS a) of the monovalent organic group (L a) to the average degree of substitution (DS b) of the monovalent organic group (L b) is preferably 1 to 2.5, more preferably 1.3 to 2.2. When the ratio is within the above range, the affinity for the oil agent is more excellent.
The monovalent organic group (L b) may replace a hydrogen atom of any of 3 hydroxyl groups in a glucose unit in cellulose. The cellulose derivative (a) may have only one monovalent organic group (L b) or two or more monovalent organic groups (L b).
The cellulose derivative (a) may have a monovalent organic group (L c) having 5 or less carbon atoms, which has a hydrocarbon group at the terminal and no ether bond, in place of at least a part of the hydrogen atoms constituting the hydroxyl group in cellulose. When the organic group (L c) is monovalent, the affinity for the oil tends to be more excellent. The hydrocarbon group at the terminal of the monovalent organic group (L c) may be any hydrocarbon group of a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be any hydrocarbon group of a straight chain or a branched chain. Examples of the hydrocarbon group include methyl, ethyl, propyl, isopropyl, butyl and pentyl.
The monovalent organic group (L c) is directly bonded to an oxygen atom in the cellulose skeleton or bonded to the cellulose skeleton via a linking group having the oxygen atom as a constituent atom. The linking group is formed of the oxygen atom and a monovalent organic group (L c). Examples of the linking group include: ether linkages, ester linkages, urethane linkages, phosphonic acid groups, thioester linkages, and the like. Among them, ester bonds are preferable from the viewpoint of easy introduction.
The total number of carbon atoms in the monovalent organic group (L c) is preferably 1 to 5, more preferably 2 to 4.
The monovalent organic group (L c) is particularly preferably a group represented by the following formula (4).
-X3-R4(4)
[ Wherein R 4 represents the above-mentioned hydrocarbon group, and X 3 represents a group which is directly bonded or can be bonded to an oxygen atom in cellulose to form a linking group. The leftwardly extending bonding arm bonds to an oxygen atom in the cellulose backbone. ]
Examples of the linking group that can be formed by X 3 include those exemplified and described as the linking group that can be formed by X 1 described above. As X 3, for example, there may be mentioned: direct bonding, carbonyl (-C (=o) -), amido (-C (=o) -N (-R) -), (-P (=o) (-R) -) thiocarbonyl (-C (=s) -) and the like. R is a hydrogen atom or a monovalent organic group. As X 3, a carbonyl group is preferable. That is, the monovalent organic group (L c) is preferably an acyl group.
In the cellulose derivative (a), the average degree of substitution of the monovalent organic group (L a) is preferably equal to or higher than the average degree of substitution of the monovalent organic group (L c), and more preferably higher than the average degree of substitution of the monovalent organic group (L c). The difference [ DS a-DSc ] between the average degree of substitution (DS a) of the monovalent organic group (L a) and the average degree of substitution (DS c) of the monovalent organic group (L c) is preferably 1.1 to 2.9, more preferably 1.4 to 2.7. When the difference is within the above range, the affinity for the oil agent is more excellent.
In the cellulose derivative (a), the average substitution degree (DS c) of the monovalent organic group (L c) may be 0.05 or more, and may be 0.1 or more. The DS c is preferably 1.0 or less, more preferably 0.5 or less, and still more preferably 0.25 or less.
The ratio [ DS a/DSc ] of the average degree of substitution (DS a) of the monovalent organic group (L a) to the average degree of substitution (DS c) of the monovalent organic group (L c) is preferably 5 to 20, more preferably 7 to 16. When the ratio is within the above range, the affinity for the oil agent is more excellent.
The monovalent organic group (L c) may replace a hydrogen atom of any of 3 hydroxyl groups in a glucose unit in cellulose. The cellulose derivative (a) may have only one monovalent organic group (L c) or two or more monovalent organic groups (L c).
The total of the average degree of substitution (DS a) of the monovalent organic groups (L a), the average degree of substitution (DS b) of the monovalent organic groups (L b), and the average degree of substitution (DS c) of the monovalent organic groups (L c) is 1.1 or more, preferably 1.5 or more, more preferably 2.0 or more, still more preferably 2.5 or more, and particularly preferably 2.7 or more. The higher the above total, the more excellent the affinity for the oil.
In the cellulose derivative (a), at least a part of hydrogen atoms constituting hydroxyl groups in cellulose may be unsubstituted. That is, the cellulose derivative (a) may have hydroxyl groups derived from cellulose. The cellulose derivative (a) may have, in addition to the monovalent organic group (L a), the monovalent organic group (L b), and the monovalent organic group (L c), other substituents in which at least a part of hydrogen atoms constituting hydroxyl groups in cellulose are substituted. The cellulose derivative (a) may have only one or two or more of the above other substituents.
The total proportion of one or more substituents selected from the group consisting of monovalent organic groups (L a), monovalent organic groups (L b) and monovalent organic groups (L c) in the cellulose derivative (a) is preferably 50 mol% or more, more preferably 80 mol% or more, and still more preferably 90 mol% or more, of all substituents (100 mol%) substituted with hydrogen atoms constituting hydroxyl groups in cellulose. The proportion of the other substituents (particularly monovalent substituents having a hydroxyl group at the terminal) in the cellulose derivative (a) is preferably 50 mol% or less, more preferably 20 mol% or less, and still more preferably 10 mol% or less, of all substituents (100 mol%) substituted with hydrogen atoms constituting hydroxyl groups in cellulose.
As the oil, for example, known or conventional oil used in cosmetic compositions and the like can be used, and examples thereof include: hydrocarbon oils, ester oils, silicone oils. The oil is preferably in a liquid state having fluidity at 25 ℃. The oil may be volatile. The above-mentioned oils may be used singly or in combination of two or more.
The hydrocarbon oils described above have a flash point of, for example, 35 to 87 ℃. Examples of the hydrocarbon oil include: paraffin hydrocarbon oils such as n-decane, n-undecane and n-dodecane; isoparaffin hydrocarbon oils such as isodecane, isododecane and hydrogenated polyisobutene; cyclic alkane hydrocarbon oils such as cyclodecane and cyclododecane.
Examples of the ester oil include: isotridecyl isononanoate, diisostearyl malate, isostearyl myristate, octyldodecyl ricinoleate, neopentyl glycol dicaprate, diglyceryl diisostearate, glyceryl monoisostearate, 2-ethylhexyl p-methoxycinnamate, tocopheryl acetate, diglyceryl monoisostearate, and the like. The vegetable oil also belongs to the ester oil.
Examples of the silicone oil include: octamethyltetrasiloxane, decamethyltetrasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and the like.
Among them, the above-mentioned oiling agent is preferably hydrocarbon oil or ester oil.
The content of the cellulose derivative (a) in the composition is preferably 0.06 to 30% by mass, more preferably 0.1 to 20% by mass, based on 100% by mass of the total composition. When the content is 0.06 mass% or more, the film formability is more excellent. When the content is 30 mass% or less, the cellulose derivative has a more excellent affinity for the oil.
The content of the oil agent in the composition is preferably 50 to 99.99% by mass, more preferably 60 to 99.9% by mass, based on 100% by mass of the total composition. When the content is 50% by mass or more, the cellulose derivative has a more excellent affinity for the oil. When the content is 99.99 mass% or less, the film formability is more excellent.
When the oil agent contains a hydrocarbon oil as a main component, the content of the hydrocarbon oil in the composition is preferably greater than 50% by mass, more preferably 70% by mass or more, still more preferably greater than 80% by mass, and particularly preferably 90% by mass or more, based on 100% by mass of the total composition. Since the cellulose derivative has excellent affinity for various oils, even if the content of the hydrocarbon oil is more than 50 mass% (particularly more than 80 mass%), the cellulose derivative has excellent affinity for the oils.
When the oil agent contains an ester oil as a main component, the content of the ester oil in the composition is preferably greater than 50% by mass, more preferably 70% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass or more, based on 100% by mass of the total amount of the composition. Since the cellulose derivative has excellent affinity for various oils, even if the content of the ester oil is more than 50 mass%, the cellulose derivative has excellent affinity for the oils.
The concentration of each component in the composition can be appropriately adjusted by dilution and concentration according to the conditions at the time of manufacture, use, and the like.
The composition may contain other components than the cellulose derivative (a) and the oil. The other components mentioned above may be: powder, surfactant, lower alcohol, polyhydric alcohol, polymer other than cellulose derivative (A), ultraviolet absorber, antioxidant, dye, perfume, color material, antifouling agent, humectant, water, etc. The other components may be used alone or in combination of two or more. The content of the oil agent in the organic solvent contained in the composition is preferably 80% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, and particularly preferably 98% by mass or more, relative to 100% by mass of the total amount of the organic solvent.
The formulation of the above composition may be any of solid, semisolid, gel, liquid, and the like.
The above-mentioned composition containing the cellulose derivative (a) can be obtained by dispersing/dissolving the cellulose derivative (a) in a solvent, or by swelling and gelling the cellulose derivative (a) with a solvent.
[ Cellulose derivative ]
The present disclosure also provides a cellulose derivative comprising a monovalent organic group (L b) substituted for at least a part of hydrogen atoms constituting a hydroxyl group in cellulose, wherein the monovalent organic group (L b) has a group represented by the following formula (2) at the terminal.
-O-R2(2)
[ Wherein R 2 represents a hydrocarbon group having 6 or less carbon atoms ]
In the present specification, a cellulose derivative having at least a monovalent organic group (L b) may be referred to as a "cellulose derivative (B)". The cellulose derivative (B) is a novel compound and tends to be excellent in stacking inhibition.
Examples of the monovalent organic group (L b) in the cellulose derivative (B) include those exemplified and described as the monovalent organic group (L b) optionally provided in the cellulose derivative (a). The monovalent organic group (L b) in the cellulose derivative (B) is preferably the same as the monovalent organic group (L b) optionally provided in the cellulose derivative (a).
In the cellulose derivative (B), the average substitution degree (DS b) of the monovalent organic group (L b) is preferably 0.1 or more, more preferably 0.5 or more, and further preferably 1.0 or more. When DS b is 0.1 or more, the accumulation of cellulose derivatives is further suppressed. DS b may be 2.9 or less, 2.5 or less, 1.9 or less, 1.5 or less, 1.3 or less.
The cellulose derivative (B) may or may not have a monovalent organic group (L a). The cellulose derivative (B) may or may not have a monovalent organic group (L c). In the cellulose derivative (B), at least a part of hydrogen atoms constituting hydroxyl groups in cellulose may be unsubstituted. That is, the cellulose derivative (B) may have hydroxyl groups derived from cellulose.
The cellulose derivative (B) may have, in addition to the monovalent organic group (L a), the monovalent organic group (L b), and the monovalent organic group (L c), other substituents in which at least a part of hydrogen atoms constituting hydroxyl groups in cellulose are substituted. The cellulose derivative (B) may have only one of the above other substituents, or may have two or more kinds.
The preferred mode of the cellulose derivative (B) is the same as that of the cellulose (A).
The composition containing the cellulose derivative (B) can be obtained by dispersing/dissolving the cellulose derivative (B) in a solvent or by swelling the cellulose derivative (B) with a solvent to gel. As the solvent, an oil is preferably used.
As the oil, known or conventional ones can be used, and examples thereof include: hydrocarbon oils, ester oils, silicone oils. The oil is preferably in a liquid state having fluidity at 25 ℃. Among them, the above-mentioned oiling agent is preferably hydrocarbon oil or ester oil. Examples of the silicone oil, the ester oil, and the hydrocarbon oil include those exemplified and described as the oil agent in the composition containing the cellulose derivative (a). The above-mentioned oils may be used singly or in combination of two or more.
The content of the cellulose derivative (B) in the composition is preferably 0.06 to 30% by mass, more preferably 0.1 to 20% by mass, based on 100% by mass of the total composition. When the content is 0.06 mass% or more, the film formability is more excellent. When the content is 30 mass% or less, the cellulose derivative has a more excellent affinity for the oil.
The content of the oil agent in the composition is preferably 50 to 99.99% by mass, more preferably 60 to 99.9% by mass, based on 100% by mass of the total composition. When the content is 50% by mass or more, the cellulose derivative has a more excellent affinity for the oil. When the content is 99.99 mass% or less, the film formability is more excellent.
When the oil agent contains a hydrocarbon oil as a main component, the content of the hydrocarbon oil in the composition is preferably greater than 50% by mass, more preferably 70% by mass or more, still more preferably greater than 80% by mass, and particularly preferably 90% by mass or more, based on 100% by mass of the total composition. Since the cellulose derivative has excellent affinity for various oils, even if the content of the hydrocarbon oil is more than 50 mass% (particularly more than 80 mass%), the cellulose derivative has excellent affinity for the oils.
When the oil agent contains an ester oil as a main component, the content of the ester oil in the composition is preferably greater than 50% by mass, more preferably 70% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass or more, based on 100% by mass of the total amount of the composition. Since the cellulose derivative has excellent affinity for various oils, even if the content of the ester oil is more than 50 mass%, the cellulose derivative has excellent affinity for the oils.
The concentration of each component in the composition can be appropriately adjusted by dilution and concentration according to the conditions at the time of manufacture, use, and the like.
The composition may contain other components than the cellulose derivative (B) and the oil. Examples of the other components include those exemplified and described as other components in the composition containing the cellulose derivative (a). The other components may be used alone or in combination of two or more.
The formulation of the above composition may be any of solid, semisolid, gel, liquid, and the like.
[ Method for producing cellulose derivative ]
Examples of the cellulose derivative (a) and the cellulose derivative (B) include: (i) A method of reacting cellulose with an acyl donor in an ionic liquid, (ii) a method of reacting cellulose with an acyl donor in the presence of lithium chloride in a highly polar solvent (dimethylacetamide). The ionic liquid, the acyl donor, the highly polar solvent, and other components may be used singly or in combination.
(I) The ionic liquid used in (a) is used as a solvent for dissolving cellulose, and functions as a strong organic molecular catalyst. The ionic liquid may be used alone or in combination of two or more.
The constituent anions of the ionic liquid are not particularly limited, and examples thereof include: when a carboxylic acid anion is used as the anion, a substituent derived from the carboxylic acid anion may be introduced into the cellulose skeleton by the method of (i), for example, when an acetic acid anion is used as the anion, an acetyl group may be introduced into the cellulose derivative as a monovalent organic group (L c).
The constituent cations of the ionic liquid are preferably organic cations, and examples thereof include: ammonium cation, heterocycleCations, and the like. Examples of the ammonium cation include: aliphatic quaternary ammonium ions such as trimethyl propyl ammonium ion, trimethyl hexyl ammonium ion, tetrapentyl ammonium ion, diethyl trimethyl (2-methoxyethyl) ammonium ion, and N-butyl-N-methylpyrrolidineAnd alicyclic quaternary ammonium ions such as ions.
As heterocyclic ringExamples of cations include: imidazoleCationic and pyridineCationic, piperidineCationic, pyrrolidinesCations, and the like. As imidazolesCations, which may be mentioned: 1-ethyl-3-methylimidazoleIon, 1-butyl-3-methylimidazoleIon, 1-propyl-3-methylimidazoleIon-mediated dialkyl imidazolesCationic, 1- (1, 2 or 3-hydroxypropyl) -3-methylimidazoleIon, 1,2, 3-trimethylimidazoleIon, 1, 2-dimethyl-3-propylimidazoleIon, 1-butyl-2, 3-dimethylimidazoleIon-class trialkylimidazoleCationic, 1-allyl-3-ethylimidazoleIon, 1-allyl-3-butylimidazole1-Allyl-3-alkylimidazoles as ionsCationic, 1, 3-diallyl imidazoleCations, and the like. As pyridineCations, which may be mentioned: n-propylpyridineIon, N-butylpyridineIon, 1-butyl-4-methylpyridineIon, 1-butyl-2, 4-dimethylpyridineIons, and the like. As piperidineCations, which may be mentioned: N-methyl-N-ethylpiperidineIon, N-methyl-N-propylpiperidineIon, N-methyl-N-butylpiperidineIons, and the like. As pyrrolidinesCations, which may be mentioned: N-methyl-N-ethylpyrrolidineIon, N-methyl-N-propyl pyrrolidineIon, N-methyl-N-butylpyrrolidineIons, and the like.
The acyl donor may be, for example, a compound capable of reacting with a hydroxyl group in cellulose to replace a hydrogen atom with an acyl group, and may be appropriately selected according to the monovalent organic group (La) or the monovalent organic group (Lb). Examples of such a compound include: chain or cyclic esters (e.g., vinyl carboxylates), aldehydes, carboxylic acid halides, carboxylic acid anhydrides. Examples of the carboxylic acid halide include fluoride, chloride, bromide, and iodide.
The amount of the acyl donor is not particularly limited and may be appropriately adjusted according to the substitution degree of the introduced substituent. The amount of the acyl donor is, for example, 100 to 6000 parts by mass, preferably 100 to 3000 parts by mass, based on 100 parts by mass of the total amount of cellulose. The amount of the acyl donor is, for example, 1 to 20 equivalents, preferably 3 to 9 equivalents, based on 1 equivalent (i.e., 3 equivalents of hydroxyl groups) of glucose in cellulose.
Solvents other than ionic liquids may also be added in the reaction of (i). As the solvent, a known or conventional organic solvent or water can be used. The manufacturing cost can be reduced while maintaining the affinity of cellulose for the oil. The solvent is particularly preferably the highly polar solvent.
The reaction temperature is, for example, 40 to 120℃and the reaction time is, for example, 1 minute to 48 hours. The solution after the reaction may be subjected to reprecipitation using a solvent such as methanol, filtration, or the like to introduce the above-mentioned acyl donor to an oxygen atom of a hydroxyl group in cellulose, thereby obtaining a cellulose derivative having a monovalent organic group (La), a monovalent organic group (Lb), or a monovalent organic group (Lc). In addition, the ionic liquid used in the reaction can be recycled.
(Ii) The highly polar solvent used in (a) may be used as a solvent for dissolving cellulose. Examples of the highly polar solvent include: amide solvents such as dimethylformamide, N-dimethylacetamide, N-methylpiperidone, and 1, 3-dimethyl-2-imidazolidinone; dimethyl sulfoxide; sulfolane; gamma-butyrolactone; hexamethylphosphoric triamide, and the like. Among them, from the viewpoint of excellent solubility of cellulose, an amide-based solvent is preferable, and N, N-dimethylacetamide is more preferable.
Examples of the acyl donor include those exemplified and described as usable acyl donors in the above (i). The amount of the acyl donor is not particularly limited and may be appropriately adjusted according to the substitution degree of the introduced substituent. The amount of the acyl donor is, for example, 100 to 6000 parts by mass, preferably 100 to 3000 parts by mass, based on 100 parts by mass of the total amount of cellulose. The amount of the acyl donor is, for example, 1 to 20 equivalents, preferably 3 to 15 equivalents, relative to 1 equivalent of glucose (i.e., 3 equivalents of hydroxyl groups) in cellulose.
The amount of the lithium chloride is not particularly limited, but is, for example, 1 to 12 parts by mass, preferably 3 to 9 parts by mass, based on 100 parts by mass of the total amount of the highly polar solvent.
In (ii), a basic catalyst is preferably used. Examples of the basic catalyst include: tertiary amines such as triethylamine, pyridine, dimethylaminopyridine and triphenylphosphine.
The reaction temperature is, for example, 40 to 120℃and the reaction time is, for example, 1 minute to 48 hours. The solution after the reaction may be subjected to reprecipitation using a solvent such as methanol, filtration, or the like to introduce the above-mentioned acyl donor to an oxygen atom of a hydroxyl group in cellulose, thereby obtaining a cellulose derivative having a monovalent organic group (La), a monovalent organic group (Lb), or a monovalent organic group (Lc).
[ Use of composition ]
The above composition (composition containing the cellulose derivative (a) and/or the cellulose derivative (B)) is excellent in affinity for oils even when various oils are used. Therefore, even when the content ratio of the hydrocarbon oil or the ester oil is high, for example, the cellulose derivative tends to have excellent affinity for the oil agent and excellent film formability (film formability). Further, since the cellulose derivative has excellent affinity for the oil agent even when the content of the hydrocarbon oil is high, the content of the ester oil can be suppressed to a low level, and tackiness of the film formed from the composition can be suppressed. In addition, since the cellulose derivative can be produced using cellulose as a raw material, it is not necessary to pass through CAP or CAB, and thus the synthesis process of the cellulose derivative can be shortened, and environmental burden and production cost can be reduced.
The composition can be used in various fields such as a paper field for packaging, a printing field, a fiber field, a medical field, and a cosmetic field. For example, it can be used for cosmetics, external preparations for skin, coating agents, paints, etc. In the above-mentioned applications, the film-forming agent can be used.
The cosmetic (cosmetic composition) may be applied to skin such as skin, lips, nails, etc., eyelashes, hair, etc. Specific examples of the cosmetic include: lip cosmetics such as lipstick, lip gloss, lip pencil, etc.; make-up cosmetics such as mascara, eyeliner, eye shadow, blush, foundation (cream foundation, powder foundation, liquid foundation, etc.), concealer, etc.; cream, lotion, make-up water, all-in-one gel, face lotion, solid soap, massage agent, deodorant, sun cream, hair tonic, shampoo, conditioner, hair dye, hair oil, hair wax, hair styling spray, hair foam (hair foam), waterproof cosmetic, and the like. The cosmetic may be in any of liquid, semisolid and solid state at normal temperature. The above-mentioned cosmetic is preferably an oily cosmetic comprising an oil agent as a base.
The cosmetic may be filled in a container. Examples of the container include a bottle container, a tank container, and a tube container.
The coating agent can be used for automobiles, wood, plastics, metals and the like. In the printing field, for example, the film can be used for solvent casting. Examples of such applications include films for photographs and protective films for liquid crystal displays.
As the medical field, there is mentioned a drug delivery application. In drug delivery applications, the cellulose derivative may act as a film forming agent, for example, as a coating agent for tablets or particles. In addition, the cellulose derivative can be used to form an amorphous mixture of a poorly soluble drug, thereby improving the solubility and bioavailability of the drug. In addition, the cellulose derivatives described above may be used in controlling drug delivery where the drug is released from the cellulose derivatives in response to an external stimulus, such as a change in pH.
The aspects disclosed in the present specification may also be combined with any of the other features disclosed in the present specification. Each configuration and combination thereof in each embodiment are examples, and addition, omission, substitution, and other modifications of the configuration may be appropriately performed within a range not departing from the gist of the present disclosure. The invention of the present disclosure is not limited to the embodiments and examples described below, but is limited only by the claims.
Examples
Hereinafter, an embodiment of the present disclosure will be described in more detail based on examples.
Example 1
To ethyl methylimidazole in a nitrogen atmosphere1.5G (9.4 mmol) of microcrystalline cellulose (available from Avicel, asahi chemical Co., ltd.) was added to a mixed solvent of 29g of acetate and 38g of dimethyl sulfoxide, and the mixture was dissolved at 80 ℃. After 8.1g (36 mmol) of vinyl laurate was added thereto, the mixture was reacted at 80℃for 30 minutes, precipitated in methanol, purified and dried to prepare a cellulose derivative (cellulose laurate acetate) in which acetyl groups and lauroyl groups were substituted on oxygen atoms of a cellulose skeleton. Then, the obtained cellulose derivative was heated to 70℃in isododecane to prepare a swollen gel (concentration: 10 mass%) of the cellulose derivative.
Example 2
To ethyl methylimidazole in a nitrogen atmosphere1.0G (6.2 mmol) of microcrystalline cellulose (Avicel, asahi chemical Co., ltd.) was added to a mixed solvent of 19g of acetate and 24g of dimethyl sulfoxide, and the mixture was dissolved at 80 ℃. After 4.8g (18 mmol) of vinyl myristate was added thereto, the mixture was reacted at 80℃for 40 minutes, precipitated in methanol, purified and dried to prepare a cellulose derivative (cellulose acetate myristate) in which acetyl groups and myristoyl groups were substituted on oxygen atoms of a cellulose skeleton. Then, the obtained cellulose derivative was heated to 70℃in isododecane to prepare a swollen gel (concentration: 10 mass%) of the cellulose derivative.
Example 3
3.9G of a cellulose derivative (cellulose acetate palmitate) in which an acetyl group and a palmitoyl group were substituted on an oxygen atom of a cellulose skeleton was produced in the same manner as in example 2, except that 5.8g (20 mmol) of vinyl palmitate was added instead of vinyl myristate and the mixture was reacted at 80℃for 30 minutes. Then, the obtained cellulose derivative was heated to 70℃in isododecane to prepare a swollen gel (concentration: 10 mass%) of the cellulose derivative.
Example 4
A cellulose derivative (cellulose acetate stearate) in which acetyl group and stearyl group were substituted on the oxygen atom of the cellulose skeleton was produced in the same manner as in example 2, except that 4.2g (13 mmol) of vinyl stearate was used instead of vinyl myristate. Then, the obtained cellulose derivative was heated to 70℃in isododecane to prepare a swollen gel (concentration: 10 mass%) of the cellulose derivative.
Example 5
A cellulose derivative (cellulose acetate stearate) was produced in the same manner as in example 4 except that the amount of vinyl stearate added was 5.4g (17 mmol) and the reaction was carried out at 80 ℃ for 30 minutes. Then, the obtained cellulose derivative was heated to 70℃in isododecane to prepare a swollen gel (concentration: 10 mass%) of the cellulose derivative.
Example 6
A cellulose derivative (cellulose acetate stearate) was produced in the same manner as in example 5 except that the amount of vinyl stearate added was 7.3g (23 mmol). Then, the obtained cellulose derivative was added to isododecane, and dissolved at 70℃to prepare a cellulose derivative solution (concentration: 10 mass%).
Example 7
To 21.43g (concentration 6.7 mass%) of a dimethylacetamide solution in which lithium chloride was dissolved, 0.50g (3.1 mmol) of microcrystalline cellulose (manufactured by Sigma-Aldrich) was added and dissolved in a nitrogen atmosphere. To this was added 1.13g (9.3 mmol) of dimethylaminopyridine and 4.51g (27.8 mmol) of octanoyl chloride, followed by stirring at 80℃for 3 hours, whereby a reaction was performed. Then, the product was precipitated by adding a large amount of methanol and recovered by filtration. The obtained product was dissolved in 20g of Tetrahydrofuran (THF), and the solution was added dropwise to a large amount of methanol to purify the product, and the precipitate was collected by filtration and dried to obtain 1.01g of a cellulose derivative (octanoyl cellulose) in which octanoyl groups were substituted on oxygen atoms of a cellulose skeleton. Then, the obtained cellulose derivative was added to isododecane, and dissolved at 70℃to prepare a cellulose derivative solution (concentration: 10 mass%).
Example 8
1.64G of a cellulose derivative (lauric acid cellulose) in which lauroyl groups were substituted on oxygen atoms of a cellulose skeleton was produced in the same manner as in example 7 except that 6.07g (27.8 mmol) of lauroyl chloride was added instead of octanoyl chloride. Then, the obtained cellulose derivative was added to isododecane, and dissolved at 70℃to prepare a cellulose derivative solution (concentration: 10 mass%).
Preparation example 1
Thionyl chloride (14.69 g,0.12 mol) was slowly added dropwise to [2- (2-methoxyethoxy) ethoxy ] acetic acid (20.00 g,0.11 mol) at room temperature under nitrogen atmosphere. After the completion of the dropwise addition, the reaction was carried out by stirring at about 40℃for about 3 hours, and then the temperature was raised to 60℃to complete the reaction. After confirming the disappearance of the starting material by GC analysis, the reaction mixture was cooled to room temperature, and the excess thionyl chloride was distilled off as a solvent, whereby acid chloride (21.43 g,0.11mol, 97.1 mass%) having a hydrophilic group was obtained.
Example 9
To 32.22g (concentration 6.7 mass%) of a dimethylacetamide solution in which lithium chloride was dissolved, 0.80g (4.9 mmol) of TENCEL (registered trademark) (manufactured by Fujibo Holdings corporation) was added and dissolved in a nitrogen atmosphere. A mixture of 1.81g (14.8 mmol) of dimethylaminopyridine, 14.37g (22.2 mmol) of the acid chloride prepared in preparation example 1 and 4.86g (22.2 mmol) of lauroyl chloride was added thereto, followed by stirring at 80℃for 3 hours, whereby a reaction was carried out. Then, a large amount of methanol was added to precipitate a product, and the product was recovered by filtration. The obtained product was dissolved in THF 32g and added dropwise to a large amount of methanol, followed by purification, and the precipitate was collected by filtration and dried, whereby 3.370g of a cellulose derivative in which lauroyl groups and groups derived from the above-mentioned acid chloride (sometimes referred to as "groups containing ether bonds") were substituted on oxygen atoms of a cellulose skeleton was obtained. Then, the obtained cellulose derivative was added to isododecane, and dissolved at 70℃to prepare a cellulose derivative solution (concentration: 10 mass%). The 1 H-NMR spectrum of the cellulose derivative is shown in FIG. 1.
Example 10
To 16.11g (concentration: 6.7 mass%) of dimethylacetamide solution in which lithium chloride was dissolved, 0.40g (2.5 mmol) of microcrystalline cellulose (manufactured by Sigma-Aldrich) was added and dissolved in a nitrogen atmosphere. A mixture of 0.90g (7.4 mmol) of dimethylaminopyridine, 2.18g (11.1 mmol) of the acid chloride prepared in preparation example 1, and 2.43g (11.1 mmol) of lauroyl chloride was added thereto, followed by stirring at 80℃for 3 hours, whereby a reaction was carried out. Then, a large amount of methanol was added to precipitate a product, and the product was recovered by filtration. The obtained product was dissolved in THF 32g and added dropwise to a large amount of methanol, whereby purification was performed, and the precipitate was recovered by filtration and dried, whereby 0.997g of a cellulose derivative in which lauroyl groups and groups derived from the above-mentioned acid chloride (groups containing ether bonds) were substituted on oxygen atoms of a cellulose skeleton was obtained. Then, the obtained cellulose derivative was added to isododecane, and dissolved at 100℃to prepare a cellulose derivative solution (concentration: 10 mass%).
Example 11
The cellulose derivative produced in example 1 was added to isotridecyl isononanoate, and dissolved at 70℃to produce a cellulose derivative solution (concentration: 10 mass%).
Comparative example 1
Cellulose acetate (manufactured by cellophane corporation) was added to isododecane to prepare a cellulose derivative mixed solution (mixing ratio: 10 mass%).
Comparative example 2
Cellulose derivatives (cellulose laurate acetate) in which acetyl groups and lauroyl groups were substituted on oxygen atoms of the cellulose skeleton were prepared in the same manner as in example 2 except that 1.3g (5.7 mmol) of vinyl laurate was added instead of vinyl myristate and the reaction was carried out at 80℃for 30 minutes. Then, the obtained cellulose derivative was added to isododecane to prepare a cellulose derivative mixed solution (mixing ratio: 10 mass%).
Comparative example 3
10G of hydroxyethylcellulose (average degree of substitution of hydroxyethyl group: 1.8 to 2.3) was added to 100g of dimethyl sulfoxide under nitrogen atmosphere, and stirred at 80℃for 4 hours to dissolve. After dissolution, 30g of pyridine was added. To this, 40g of stearoyl chloride was added, followed by reaction at 80℃for 8 hours, precipitation in methanol, purification and drying were carried out, whereby a cellulose derivative having a stearoyl group substituted on the oxygen atom of hydroxyethyl cellulose was produced. Then, the obtained cellulose derivative was added to isododecane to prepare a cellulose derivative mixed solution (mixing ratio: 10 mass%).
< Evaluation >
The cellulose derivatives and cellulose derivative solutions, swelling gels of cellulose derivatives, or mixed solutions prepared or used in examples and comparative examples were evaluated as follows. The results are shown in the table.
(1) Average degree of substitution
1 H-NMR analyses were carried out on the cellulose derivatives obtained in the examples and comparative examples, respectively. Protons derived from the terminal methyl group of the acyl group of the fatty acid ester having 6 or more carbon atoms in the esterified cellulose derivative occur in the vicinity of 0.9ppm, and 7 protons of the cellulose skeleton occur in the vicinity of 3.2 to 5.2 ppm. Based on this, the average substitution degree of the acyl group derived from the above fatty acid ester to be introduced is calculated from the calculated integral value. The average substitution degree of the acetyl group was similarly calculated from methyl protons derived from the acetyl group occurring in the vicinity of 2 ppm. In examples 9 and 10, since it was difficult to clearly read the integral value of protons in the cellulose skeleton, the following benzoylation reaction was further performed to replace the residual hydroxyl groups, and the total average substitution degree of all substituents including benzoyl groups was set to 3.0 in the obtained cellulose derivative, and the calculation was performed based on the ratio of the integral values of protons derived from benzoyl groups, protons derived from groups having ether bonds, and protons derived from lauroyl groups.
(Benzoylation reaction)
100Mg of the cellulose derivative obtained in example 9 or 10 and 4g of pyridine were put into a test tube, and heated to 115℃under nitrogen to be dissolved. To this was added dropwise 100mg of benzoyl chloride in excess, and the mixture was reacted at 115℃for 5 hours. Then, the reaction solution was added dropwise to 15g of methanol as a poor solvent, and the precipitate was dried to obtain a cellulose derivative in which unreacted hydroxyl groups were benzoylated.
(2) Affinity for
The affinity of the cellulose derivative to the oil was evaluated on the cellulose derivative solutions, swelling gels, or mixed solutions obtained in examples and comparative examples according to the following criteria.
A: is dissolved by heating at 70 ℃.
B: the gel was swelled by heating at 70 ℃.
C: is dissolved by heating at 100 ℃.
D: no dissolution and dispersion occurred and no swollen gel was formed upon heating at 100 ℃.
(3) Film formability
The cellulose derivative solutions, swollen gels, or mixed solutions obtained in examples and comparative examples were spread on an aluminum cup by spreading with a spatula, respectively, and were heated at 70℃for 1 hour to a thickness of about 3 mm. In addition, the solvent was volatilized by spreading on a glass plate with a spatula and heating at 70℃for 5 minutes. Then, the glass was cooled to room temperature, and the state of the films formed on the aluminum cup and the glass was visually observed, and evaluated according to the following criteria.
A: a transparent film can be formed on either the aluminum cup or the glass plate.
B: a film can be formed on either the aluminum cup or the glass plate, but the film is translucent or white in color.
C: a film can be formed on either the aluminum cup or the glass plate, but a crack is generated in the film.
D: transparent films can be formed on either the aluminum cup or the glass plate, but they are thicker than a to C (cannot be spread thinly).
E: a film could not be formed on either the aluminum cup or the glass plate.
TABLE 1
TABLE 2
As shown in tables 1 and 2, in the cellulose derivative solutions or swollen gels of examples, the cellulose derivative was excellent in affinity with the oil, and the cellulose derivative was dissolved in isododecane or isotridecyl isononanoate at 70 to 100 ℃ or formed a swollen gel, and was excellent in affinity with any oil of hydrocarbon oil only and ester oil only. In addition, the cellulose derivative solution of examples also had excellent film formability. In particular, the more excellent the affinity, the more excellent the film formability. In addition, if the film formation is easy, the elongation at the time of coating is good, and the feeling after coating is good. On the other hand, when the cellulose derivative having no monovalent organic group (L a) or the average substitution degree is less than 1.1 (comparative examples 1 and 2), the cellulose derivative having an organic group introduced into the hydroxyalkyl cellulose (comparative example 3) was not dissolved or dispersed in isododecane, and a swollen gel was not formed, and the film formability was poor.
Example 12
(Preparation of liquid foundation)
After mixing the components shown in table 3, the mixture was stirred well and filled into a container to prepare a liquid foundation. The resulting liquid foundation was applied to the skin in a small amount, and as a result, water resistance/sebum resistance and flexibility without feeling a film feel were maintained.
TABLE 3
Example 13
(Preparation of sunscreen cream)
After mixing the components shown in table 4, they were stirred sufficiently and filled into a container, thereby preparing a sunscreen cream. The obtained sunscreen cream was applied to the skin, and as a result, it had good feel and water-proof properties.
TABLE 4
| Composition of the components | Mass percent of |
| Diethylamino hydroxybenzoyl hexyl benzoate | 2.0 |
| Diethylhexyloxyphenol methoxyphenyl triazine | 0.5 |
| Trade name "Uvinul MC80" (manufactured by BASF corporation) | 7.0 |
| Diisopropyl sebacate | 10.0 |
| Polydimethylsiloxane | 2.0 |
| Isodecyl (Isodecyl) | 16.47 |
| Cellulose derivative solution of example 2 | 10.0 |
| PEG-9 Dimethicone Ethyl Dimethicone | 2.0 |
| Trade name "DIS-OP-10A" (made by Sakai chemical industry Co., ltd.) | 4.0 |
| Trade name "DIF-OP-3W" (made by Sakai chemical industry Co., ltd.) | 10.0 |
| Cellulose acetate | 5.0 |
| 1, 3-Butanediol | 3.0 |
| Phenoxyethanol | 0.2 |
| Ethanol | 7.0 |
| Sodium chloride | 0.5 |
| EDTA-2Na | 0.03 |
| Purified water | Allowance of |
| Totalizing | 100.0 |
Claims (17)
1. A composition comprising a cellulose derivative and an oil,
The cellulose derivative has a monovalent organic group (L a) having a hydrocarbon group having 6 or more carbon atoms at the terminal and having no ether bond, which is substituted with at least a part of hydrogen atoms constituting a hydroxyl group in cellulose, and the monovalent organic group (L a) has an average substitution degree of 1.1 or more.
2. The composition of claim 1, wherein,
The oil agent is at least one selected from hydrocarbon oil, ester oil and silicone oil.
3. The composition of claim 2, wherein,
The content of the hydrocarbon oil is more than 80 mass%.
4. The composition of claim 2, wherein,
The content of the ester oil is more than 50 mass%.
5. The composition according to any one of claim 1 to 4, wherein,
The cellulose derivative has a monovalent organic group (L c) having 5 or less carbon atoms, which has a hydrocarbon group at the terminal and no ether bond, in place of at least a part of hydrogen atoms constituting a hydroxyl group in the cellulose.
6. The composition of claim 5, wherein,
In the cellulose derivative, the average substitution degree of the monovalent organic group (L a) is equal to or higher than the average substitution degree of the monovalent organic group (L c).
7. The composition according to claim 5 or 6, wherein,
In the cellulose derivative, the monovalent organic group (L c) has an average substitution degree of 1.0 or less.
8. The composition according to any one of claims 1 to 7, wherein,
The monovalent organic group (L a) is a group represented by the following formula (1),
-X1-R1(1)
In the formula (1), R 1 represents the hydrocarbon group having 6 or more carbon atoms, X 1 represents a group which is directly bonded or can be bonded to an oxygen atom constituting a hydroxyl group in the cellulose to form a linking group, and a bonding arm extending leftward is bonded to an oxygen atom in the cellulose skeleton.
9. An oily cosmetic comprising the composition of any one of claims 1 to 8.
10. A cellulose derivative comprising a monovalent organic group (L b) substituted with at least a part of hydrogen atoms constituting a hydroxyl group in cellulose, wherein the monovalent organic group (L b) has a group represented by the following formula (2) at the terminal,
-O-R2(2)
In the formula (2), R 2 represents a hydrocarbon group having 6 or less carbon atoms.
11. The cellulose derivative according to claim 10, wherein,
The monovalent organic group (L b) contains 2 or more ether linkages.
12. The cellulose derivative according to claim 10 or 11, wherein,
The monovalent organic group (L b) is bonded to the cellulose skeleton via an ester bond having an oxygen atom constituting the hydroxyl group as a constituent atom.
13. The cellulose derivative according to any one of claims 10 to 12, wherein,
The monovalent organic group (L b) comprises a (poly) oxyalkylene chain.
14. The cellulose derivative according to any one of claims 10 to 13, which comprises a monovalent organic group (L a) having a hydrocarbon group having 6 or more carbon atoms at the terminal and having no ether bond, wherein the monovalent organic group (L a) is substituted for at least a part of hydrogen atoms constituting a hydroxyl group in the cellulose.
15. The cellulose derivative according to claim 14, wherein,
The average degree of substitution of the monovalent organic groups (L a) is greater than the average degree of substitution of the monovalent organic groups (L b).
16. A composition comprising:
a cellulose derivative according to any one of claims 10 to 15, and
And (3) oiling agent.
17. An oily cosmetic comprising the composition of claim 16.
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| JP2021-193177 | 2021-11-29 | ||
| JP2021-196936 | 2021-12-03 | ||
| JP2021196936 | 2021-12-03 | ||
| PCT/JP2022/043619 WO2023095892A1 (en) | 2021-11-29 | 2022-11-25 | Composition and cellulose derivative |
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