JP2005145851A - Oil-gelling agent, method for producing the same, and oil gel and cosmetic each containing the same - Google Patents
Oil-gelling agent, method for producing the same, and oil gel and cosmetic each containing the same Download PDFInfo
- Publication number
- JP2005145851A JP2005145851A JP2003383591A JP2003383591A JP2005145851A JP 2005145851 A JP2005145851 A JP 2005145851A JP 2003383591 A JP2003383591 A JP 2003383591A JP 2003383591 A JP2003383591 A JP 2003383591A JP 2005145851 A JP2005145851 A JP 2005145851A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- dextrin
- acyl group
- acid
- oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003349 gelling agent Substances 0.000 title claims abstract description 17
- 239000002537 cosmetic Substances 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 239000004375 Dextrin Substances 0.000 claims abstract description 132
- 229920001353 Dextrin Polymers 0.000 claims abstract description 132
- 235000019425 dextrin Nutrition 0.000 claims abstract description 132
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 116
- 239000000194 fatty acid Substances 0.000 claims abstract description 116
- 229930195729 fatty acid Natural products 0.000 claims abstract description 116
- -1 fatty acid ester Chemical class 0.000 claims abstract description 109
- 125000002252 acyl group Chemical group 0.000 claims abstract description 54
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 35
- 150000003222 pyridines Chemical class 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 238000006467 substitution reaction Methods 0.000 claims abstract description 14
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 5
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical group CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 12
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 11
- 239000000126 substance Substances 0.000 abstract description 10
- 239000003921 oil Substances 0.000 description 50
- 235000019198 oils Nutrition 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 29
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 23
- 239000000499 gel Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 17
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 235000021314 Palmitic acid Nutrition 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 8
- 229940057995 liquid paraffin Drugs 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- 150000004671 saturated fatty acids Chemical class 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 5
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- 235000021357 Behenic acid Nutrition 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940116226 behenic acid Drugs 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
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- 239000000839 emulsion Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
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- 229940071085 lauroyl glutamate Drugs 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 4
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
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- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
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- MENILFUADYEXNU-UHFFFAOYSA-N tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(=O)CC2CCC1N2C(=O)OC(C)(C)C MENILFUADYEXNU-UHFFFAOYSA-N 0.000 description 1
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- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 1
- RCRYHUPTBJZEQS-UHFFFAOYSA-N tetradecanoyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC RCRYHUPTBJZEQS-UHFFFAOYSA-N 0.000 description 1
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- CUXYLFPMQMFGPL-UYWAGRGNSA-N trichosanic acid Natural products CCCCC=C/C=C/C=CCCCCCCCC(=O)O CUXYLFPMQMFGPL-UYWAGRGNSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
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- DGJTZXXNXZVULP-UHFFFAOYSA-N undecanoyl undecanoate Chemical compound CCCCCCCCCCC(=O)OC(=O)CCCCCCCCCC DGJTZXXNXZVULP-UHFFFAOYSA-N 0.000 description 1
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Images
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- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
本発明は、デキストリンと脂肪酸誘導体とをピリジン誘導体の存在下反応させエステル化して得られるデキストリン脂肪酸エステルからなるオイルゲル化剤、上記デキストリン脂肪酸エステルの製造方法並びにそれを含有するオイルゲル及び化粧料に関するものである。 The present invention relates to an oil gelling agent comprising a dextrin fatty acid ester obtained by reacting dextrin with a fatty acid derivative in the presence of a pyridine derivative, a method for producing the dextrin fatty acid ester, an oil gel containing the same, and a cosmetic. is there.
デキストリン脂肪酸エステルは、オイルゲル化性を損なうことなくオイルへの溶解性を向上するためにデンプン脂肪酸エステルを基に発明されたオイルゲル化剤である(例えば特許文献1,2,3,4参照)。このオイルゲルの透明性向上(例えば特許文献2参照)、オイルゲルへのチクソトロピー性付与(例えば特許文献3参照)、オイルゲルへの乳化性付与(例えば特許文献4参照)といった命題を解決するための発明がそれぞれ提案されている。しかしながら、これら従来のデキストリン脂肪酸エステルはデキストリンと脂肪酸クロライドをピリジンの存在下反応させる製法によって製造されるものである(例えば特許文献1、特許文献2、特許文献3、特許文献4参照、)。 Dextrin fatty acid ester is an oil gelling agent invented on the basis of starch fatty acid ester in order to improve solubility in oil without impairing oil gelation (see, for example, Patent Documents 1, 2, 3, and 4). An invention for solving the propositions of improving the transparency of the oil gel (see, for example, Patent Document 2), imparting thixotropy to the oil gel (see, for example, Patent Document 3), and imparting emulsifiability to the oil gel (for example, see Patent Document 4) Each has been proposed. However, these conventional dextrin fatty acid esters are produced by a production method in which dextrin and fatty acid chloride are reacted in the presence of pyridine (see, for example, Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4).
上記従来のピリジンの存在下で得られたデキストリン脂肪酸エステルにおいては、ゲル化力を有するものでは、しばしばオイルに対し100℃近くまで加熱攪拌しても僅かではあるが、細かい未溶解物が残り、これがしばしば化粧品としての感触に悪い影響を与え、異物として問題の対象となり、そのために莫大な損害を与えることにもなる。これを避けるために、反応系にクロロホルム、ジクロロメタン、ジクロロエタン、ベンゼン、トルエン、キシレン、ヘキサン、ヘプタン等の非極性溶媒の添加をすることはデキストリン脂肪酸エステルのオイルへの溶解性を向上させる効果はあるが、肝心なオイルゲル化能力を損なってしまうという機能的に致命的な問題があった。
また、従来の方法であるピリジン存在下で合成したデキストリン脂肪酸エステルは精製時にアルコールや水で洗浄を繰り返してから十分に乾燥してもアミン臭が残り、特に高配合で使用される化粧品においては好ましいものではなかった。
本発明ではオイル溶解性に優れたデキストリン脂肪酸エステルからなるオイルゲル化剤、そのデキストリン脂肪酸エステルの製造方法並びにそれを含有するオイルゲル及び化粧料を提供することを目的とする。
In the dextrin fatty acid ester obtained in the presence of the above-mentioned conventional pyridine, those having gelling power are often slightly heated even when heated and stirred to near 100 ° C., but fine undissolved substances remain, This often has a negative effect on the cosmetic feel and is a problem as a foreign object, thus causing enormous damage. To avoid this, adding a nonpolar solvent such as chloroform, dichloromethane, dichloroethane, benzene, toluene, xylene, hexane, or heptane to the reaction system has the effect of improving the solubility of dextrin fatty acid ester in oil. However, there was a functionally fatal problem that the essential oil-gelling ability was impaired.
In addition, dextrin fatty acid esters synthesized in the presence of pyridine, which is a conventional method, retains an amine odor even after being thoroughly washed with alcohol or water at the time of purification, and are particularly preferable for cosmetics used in high formulations. It was not a thing.
An object of the present invention is to provide an oil gelling agent comprising a dextrin fatty acid ester excellent in oil solubility, a method for producing the dextrin fatty acid ester, an oil gel containing the same, and a cosmetic.
本発明者らは、上記課題を解決するために鋭意研究を行なった結果、デキストリンと脂肪酸誘導体とを従来から使用されているピリジンの代わりに下記一般式で示されるピリジン誘導体を用いたとき合成されるデキストリン脂肪酸エステルから成るオイルゲル化剤が、驚くべきことには、オイル溶解性が良く異物の基になる未溶解物が残ることなく、異臭のしないオイルゲルや化粧料を提供できることを見出し、本発明を完成するに至った。
すなわち、本発明は(1)デキストリンと脂肪酸ハライド又は脂肪酸無水物とを式Iで示されるピリジン誘導体の存在下、エステル化して得られた以下の特性1〜特性3を満たすデキストリン脂肪酸エステルからなるオイルゲル化剤、
特性1
デキストリン骨格の平均単糖重合度が10〜150であるデキストリン脂肪酸エステル
特性2
平均アシル基置換度がグルコース単位当たり1.0以上であるデキストリン脂肪酸エステル
特性3
アシル基が、炭素数12〜22の直鎖飽和アシル基、炭素数4〜26の分岐アシル基、炭素数6〜30の不飽和アシル基及び/又は炭素数2〜11の直鎖飽和アシル基からなり、かつ、アシル基のモル比組成において、炭素数12〜22の直鎖飽和アシル基が少なくとも50%以上を構成するデキストリン脂肪酸エステル
(2)ピリジン誘導体がピコリンである(1)記載のオイルゲル化剤、
(3)ピコリンが3−メチルピリジンである1、2記載のオイルゲル化剤、
(4)デキストリンと脂肪酸クロライド又は脂肪酸無水物とを式Iで示されるピリジン誘導体の存在下、エステル化することを特徴とする以下の特性1〜特性3を満たすデキストリン脂肪酸エステルの製造方法、
特性1
デキストリン骨格の平均単糖重合度が10〜150であるデキストリン脂肪酸エステル
特性2
平均アシル基置換度がグルコース単位当たり1.0以上であるデキストリン脂肪酸エステル
特性3
アシル基が、炭素数12〜22の直鎖飽和アシル基、炭素数4〜26の分岐アシル基、炭素数6〜30の不飽和アシル基及び/又は炭素数2〜11の直鎖飽和アシル基からなり、かつ、アシル基のモル比組成において、炭素数12〜22の直鎖飽和アシル基が少なくとも50%以上を構成するデキストリン脂肪酸エステル、
(5)1、2、3記載のオイルゲル化剤を含有するオイルゲル、及び
(6)1、2、3記載のオイルゲル化剤を含有する化粧料、に関するものである。
As a result of diligent research to solve the above problems, the present inventors have synthesized dextrin and a fatty acid derivative when a pyridine derivative represented by the following general formula is used instead of the conventionally used pyridine. The oil gelling agent comprising a dextrin fatty acid ester has surprisingly been found to be able to provide oil gels and cosmetics that have good oil solubility and that do not leave undissolved substances that are the basis of foreign matters, and that do not have a foul odor. It came to complete.
That is, the present invention is (1) an oil gel comprising a dextrin fatty acid ester satisfying the following characteristics 1 to 3 obtained by esterification of dextrin and a fatty acid halide or fatty acid anhydride in the presence of a pyridine derivative represented by formula I: Agent,
Characteristic 1
Characteristic 2 of dextrin fatty acid ester having an average monosaccharide polymerization degree of dextrin skeleton of 10 to 150
Dextrin fatty acid ester characteristic 3 with an average acyl group substitution degree of 1.0 or more per glucose unit
The acyl group is a linear saturated acyl group having 12 to 22 carbon atoms, a branched acyl group having 4 to 26 carbon atoms, an unsaturated acyl group having 6 to 30 carbon atoms, and / or a linear saturated acyl group having 2 to 11 carbon atoms. And a dextrin fatty acid ester in which the linear saturated acyl group having 12 to 22 carbon atoms constitutes at least 50% or more in the molar ratio composition of the acyl group
(2) The oil gelling agent according to (1), wherein the pyridine derivative is picoline,
(3) The oil gelling agent according to 1 or 2, wherein picoline is 3-methylpyridine,
(4) A method for producing a dextrin fatty acid ester satisfying the following characteristics 1 to 3, characterized by esterifying dextrin and fatty acid chloride or fatty acid anhydride in the presence of a pyridine derivative represented by formula I:
Characteristic 1
Characteristic 2 of dextrin fatty acid ester having an average monosaccharide polymerization degree of dextrin skeleton of 10 to 150
Dextrin fatty acid ester characteristic 3 with an average acyl group substitution degree of 1.0 or more per glucose unit
The acyl group is a linear saturated acyl group having 12 to 22 carbon atoms, a branched acyl group having 4 to 26 carbon atoms, an unsaturated acyl group having 6 to 30 carbon atoms, and / or a linear saturated acyl group having 2 to 11 carbon atoms. And a dextrin fatty acid ester in which a linear saturated acyl group having 12 to 22 carbon atoms constitutes at least 50% or more in the molar ratio composition of the acyl group,
(5) Oil gel containing the oil gelling agent according to 1, 2, 3 and (6) Cosmetics containing the oil gelling agent according to 1, 2, 3,
本発明のデキストリンと脂肪酸ハライドとを従来から使用されているピリジンの代わりに特定のピリジン誘導体を用いたとき合成されるデキストリン脂肪酸エステルから成るオイルゲル化剤は、十分なゲル化力を有し、オイル溶解性が良く異物の基になる未溶解物や異臭の無い優れた性質のオイルゲルや化粧料を提供できる。 An oil gelling agent comprising a dextrin fatty acid ester synthesized using a specific pyridine derivative instead of pyridine conventionally used for the dextrin and fatty acid halide of the present invention has a sufficient gelling power, Oil gels and cosmetics having excellent solubility and good properties with no undissolved matter and a bad odor can be provided.
以下に本発明をさらに詳細に説明する。
本発明に用いられるデキストリンは、平均糖重合度10〜150、特に20〜100のデキストリンが好ましい。平均糖重合度9以下では、ワックス様となって滑らかなゲルが得られ難くなる。また、平均糖重合度が150を越えると、油剤への溶解温度が高くなる、又は溶解性が悪くなる等の問題を生ずることがある。デキストリンの糖鎖は直鎖状でもよく、分岐鎖状でもよい。
本発明に用いられる脂肪酸ハロゲン化物や脂肪酸無水物を構成する脂肪酸は、直鎖もしくは分岐の飽和もしくは不飽和脂肪酸から選択される。
本発明に用いられる脂肪酸ハロゲン化物や脂肪酸無水物の構成脂肪酸として必須であるのは、炭素数12〜22の直鎖飽和脂肪酸であり、例えば、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、アラキン酸、ベヘン酸、ペンタデカン酸、ヘプタデカン酸等が挙げられ、これらの一種又は二種以上を適宜、選択又は組み合わせて使用することができる。
炭素数12未満の直鎖脂肪酸だけではゲルを形成することが困難であり、又、炭素数22を超えるもの、即ち、炭素数23以上ではゲルが白濁し滑らかさが得られにくく、遊離脂肪酸等の副生成物や触媒、溶媒等の不純物の除去が困難である。
The present invention is described in further detail below.
The dextrin used in the present invention is preferably a dextrin having an average sugar polymerization degree of 10 to 150, particularly 20 to 100. If the average sugar polymerization degree is 9 or less, it becomes wax-like and it becomes difficult to obtain a smooth gel. On the other hand, when the average degree of sugar polymerization exceeds 150, problems such as an increase in the temperature of dissolution in the oil or a decrease in solubility may occur. The sugar chain of dextrin may be linear or branched.
The fatty acid constituting the fatty acid halide or fatty acid anhydride used in the present invention is selected from linear or branched saturated or unsaturated fatty acids.
What is essential as a constituent fatty acid of the fatty acid halide or fatty acid anhydride used in the present invention is a linear saturated fatty acid having 12 to 22 carbon atoms, such as lauric acid, myristic acid, palmitic acid, stearic acid, arachin. Examples thereof include acids, behenic acid, pentadecanoic acid, heptadecanoic acid and the like, and one or two or more of these can be appropriately selected or used in combination.
It is difficult to form a gel only with straight chain fatty acids having less than 12 carbon atoms, and those having more than 22 carbon atoms, that is, those having 23 or more carbon atoms, the gel is cloudy and difficult to obtain smoothness, such as free fatty acids. It is difficult to remove impurities such as by-products, catalysts and solvents.
また、本発明に用いられる脂肪酸ハロゲン化物や脂肪酸無水物を構成する分岐脂肪酸は、炭素数4〜26の分岐飽和脂肪酸であり、例えば、イソ酪酸、イソ吉草酸、2−エチル酪酸、エチルメチル酢酸、イソヘプタン酸、2−エチルヘキサン酸、イソノナン酸、イソデカン酸、イソトリデカン酸、イソミリスチン酸、イソパルミチン酸、イソステアリン酸、イソアラキン酸、イソヘキサコサン酸等が挙げられ、これらの一種又は二種以上を適宜選択又は組み合わせて使用することができる。
また、本発明に用いられる脂肪酸ハロゲン化物や脂肪酸無水物を構成する不飽和脂肪酸は、炭素数6〜30の不飽和脂肪酸であり、例えば、モノエン不飽和脂肪酸としては、シス−4−デセン(オブツシル)酸、9−デセン(カプロレイン)酸、シス−4−ドデセン(リンデル)酸、シス−4−テトラデセン(ツズ)酸、シス−5−テトラデセン(フィデセリン)酸、シス−9−テトラデセン(ミリストレイン)酸、シス−6−ヘキサデセン酸、シス−9−ヘキサデセン(パルミトレイン)酸、シス−9−オクタデセン(オレイン)酸、トランス−9−オクタデセン酸(エライジン酸)、シス−11−オクタデセン(アスクレピン)酸、シス−11−エイコセン(ゴンドレイン)酸、シス−17−ヘキサコセン(キシメン)酸、シス−21−トリアコンテン(ルメクエン)酸等が挙げられ、ポリエン不飽和脂肪酸としては、ソルビン酸、リノール酸、ヒラゴ酸、プニカ酸、リノレン酸、γ−リノレン酸、モロクチ酸、ステアリドン酸、アラキドン酸、EPA、イワシ酸、DHA、ニシン酸、ステアロール酸、クレペニン酸、キシメニン酸等が挙げられ、これらの一種又は二種以上を適宜、選択又は組み合わせて使用することができる。
また、本発明に用いられる脂肪酸ハロゲン化物や脂肪酸無水物を構成する直鎖短鎖飽和脂肪酸は炭素数2〜11の脂肪酸であり、例えば、ウンデカン酸、カプリン酸、カプリル酸、カプロン酸、吉草酸、酪酸、プロピオン酸、酢酸等が挙げられ、これらの一種又は二種以上を適宜、選択又は組み合わせて使用することができる。
The branched fatty acid constituting the fatty acid halide or fatty acid anhydride used in the present invention is a branched saturated fatty acid having 4 to 26 carbon atoms, such as isobutyric acid, isovaleric acid, 2-ethylbutyric acid, and ethylmethylacetic acid. , Isoheptanoic acid, 2-ethylhexanoic acid, isononanoic acid, isodecanoic acid, isotridecanoic acid, isomyristic acid, isopalmitic acid, isostearic acid, isoarachic acid, isohexacosanoic acid, etc. Or they can be used in combination.
The unsaturated fatty acid constituting the fatty acid halide or fatty acid anhydride used in the present invention is an unsaturated fatty acid having 6 to 30 carbon atoms. For example, as the monoene unsaturated fatty acid, cis-4-decene (obtusil) ) Acid, 9-decene (caprolein) acid, cis-4-dodecene (Lindell) acid, cis-4-tetradecene (Tuzu) acid, cis-5-tetradecene (phydeserine) acid, cis-9-tetradecene (myristolein) ) Acid, cis-6-hexadecenoic acid, cis-9-hexadecene (palmitolein) acid, cis-9-octadecene (oleic) acid, trans-9-octadecenoic acid (elaidic acid), cis-11-octadecene (asclepine) acid Cis-11-eicosene (gondrain) acid, cis-17-hexacosene (ximene) acid, cis-21- Riaconten (lumecenic acid) and the like are exemplified, and polyene unsaturated fatty acids include sorbic acid, linoleic acid, hiragoic acid, punicic acid, linolenic acid, γ-linolenic acid, moloctic acid, stearidonic acid, arachidonic acid, EPA, and iwacic acid , DHA, nisinic acid, stearolic acid, crepenic acid, xymenic acid and the like, and one or two or more of these can be appropriately selected or used in combination.
The straight chain short-chain saturated fatty acid constituting the fatty acid halide or fatty acid anhydride used in the present invention is a fatty acid having 2 to 11 carbon atoms, such as undecanoic acid, capric acid, caprylic acid, caproic acid, valeric acid. , Butyric acid, propionic acid, acetic acid and the like, and one or two or more of these can be appropriately selected or used in combination.
本発明の飽和又は不飽和脂肪酸のハロゲン化物、例えば脂肪酸クロライド、脂肪酸フルオライド、脂肪酸ヨーダイドがあるが、特に脂肪酸クロライドが好ましく用いられ、その具体例としてはパルミチン酸クロライド、ステアリン酸クロライド、ミリスチン酸クロライド、ラウリン酸クロライド、アラキン酸クロライド、ベヘン酸クロライド、ペンタデカン酸クロライド、ヘプタデカン酸クロライド、2−エチルヘキサン酸クロライド、イソステアリン酸クロライド、イソ酪酸クロライド、イソ吉草酸クロライド、2−エチル酪酸クロライド、イソヘプタン酸クロライド、イソノナン酸クロライド、イソデカン酸クロライド、イソトリデカン酸クロライド、イソミリスチン酸クロライド、イソパルミチン酸クロライド、イソアラキン酸クロライド、イソヘキサコサン酸クロライド、オレイン酸クロライド、ウンデカン酸クロライド、カプリン酸クロライド、カプリル酸クロライド、カプロン酸クロライド、吉草酸クロライド、酪酸クロライド、プロピオン酸クロライド、酢酸クロライド等が挙げられる。
また、本発明の飽和又は不飽和脂肪酸の無水物、例えば無水パルミチン酸、無水ステアリン酸、無水ミリスチン酸、無水ラウリン酸、無水アラキン酸、無水ベヘン酸、無水ペンタデカン酸、無水ヘプタデカン酸、無水2−エチルヘキサン酸、無水イソステアリン酸、無水イソ酪酸、無水イソ吉草酸、無水2−エチル酪酸、無水イソヘプタン酸、無水イソノナン酸、無水イソデカン酸、無水イソトリデカン酸、無水イソミリスチン酸、無水イソパルミチン酸、無水イソアラキン酸、無水イソヘキサコサン酸、無水オレイン酸、無水ウンデカン酸、無水カプリン酸、無水カプリル酸、無水カプロン酸、無水吉草酸、無水酪酸、無水プロピオン酸、無水酢酸、無水ミリスチン酸パルミチン酸、無水酢酸パルミチン酸、無水酢酸酪酸等が挙げられる。
There are halides of saturated or unsaturated fatty acids of the present invention, such as fatty acid chlorides, fatty acid fluorides, fatty acid iodides, but fatty acid chlorides are particularly preferably used, and specific examples thereof include palmitic acid chloride, stearic acid chloride, myristic acid chloride, Lauric acid chloride, arachidic acid chloride, behenic acid chloride, pentadecanoic acid chloride, heptadecanoic acid chloride, 2-ethylhexanoic acid chloride, isostearic acid chloride, isobutyric acid chloride, isovaleric acid chloride, 2-ethylbutyric acid chloride, isoheptanoic acid chloride, Isononanoic acid chloride, isodecanoic acid chloride, isotridecanoic acid chloride, isomyristic acid chloride, isopalmitic acid chloride, isoarachidic acid chlora De, Isohekisakosan acid chloride, chloride oleic acid, undecanoic acid chloride, capric chloride, caprylic chloride, caproic acid chloride, valeric chloride, acid chloride, propionyl chloride, acetyl chloride, and the like.
In addition, anhydrides of saturated or unsaturated fatty acids of the present invention, such as palmitic anhydride, stearic anhydride, myristic anhydride, lauric anhydride, arachidic anhydride, behenic anhydride, pentadecanoic anhydride, heptadecanoic anhydride, 2- Ethylhexanoic acid, isostearic anhydride, isobutyric anhydride, isovaleric anhydride, 2-ethylbutyric anhydride, isoheptanoic anhydride, isononanoic anhydride, isodecanoic anhydride, isotridecanoic anhydride, isomyristic anhydride, isopalmitic anhydride, anhydrous Isoarachidic acid, anhydrous isohexacosanoic acid, oleic anhydride, undecanoic anhydride, capric anhydride, caprylic anhydride, caproic anhydride, valeric anhydride, butyric anhydride, propionic anhydride, acetic anhydride, palmitic acid anhydride, palmitic anhydride Examples include acid and acetic butyric anhydride.
そして、本発明のデキストリン脂肪酸エステルは平均アシル基置換度でグルコース当たり1.0以上である。また、アシル基のモル比組成として、炭素数12以上22以下の直鎖アシル基は50%以上で、分岐、不飽和、炭素数11以下の短鎖アシル基は50%未満である。オイルゲル化剤として機能するには、これらのアシル基の条件を満たすことが必要である。具体例として挙げると、デキストリンパルミチン酸エステル、デキストリンステアリン酸エステル、デキストリンミリスチン酸エステル、デキストリンラウリン酸エステル、デキストリンアラキン酸エステル、デキストリンベヘン酸エステル、デキストリンペンタデカン酸エステル、デキストリンヘプタデカン酸エステル、デキストリン(パルミチン酸/ステアリン酸)エステル、(デキストリンベヘン酸/ミリスチン酸/ペンタデカン酸)エステル、デキストリン(パルミチン酸/2−エチルヘキサン酸)エステル、デキストリン(パルミチン酸/イソステアリン酸)エステル、デキストリン(ラウリン酸/オレイン酸)エステル、デキストリン(ベヘン酸/酢酸)エステル、デキストリン(パルミチン酸/イソステアリン酸/2−エチルヘキサン酸/オレイン酸/吉草酸/酢酸)エステル等である。 The dextrin fatty acid ester of the present invention has an average acyl group substitution degree of 1.0 or more per glucose. As the molar ratio composition of acyl groups, straight chain acyl groups having 12 to 22 carbon atoms are 50% or more, and branched, unsaturated, short chain acyl groups having 11 or less carbon atoms are less than 50%. In order to function as an oil gelling agent, it is necessary to satisfy the conditions of these acyl groups. Specific examples include dextrin palmitate, dextrin stearate, dextrin myristic ester, dextrin laurate, dextrin arachinate, dextrin behenate, dextrin pentadecanoate, dextrin heptadecanoate, dextrin (palmitin) Acid / stearic acid) ester, (dextrin behenic acid / myristic acid / pentadecanoic acid) ester, dextrin (palmitic acid / 2-ethylhexanoic acid) ester, dextrin (palmitic acid / isostearic acid) ester, dextrin (lauric acid / oleic acid) ) Ester, dextrin (behenic acid / acetic acid) ester, dextrin (palmitic acid / isostearic acid / 2-ethyl) Hexanoic acid / oleic acid / valeric / acetic acid) esters and the like.
本発明の式Iに示される、ピリジン誘導体としては2−メチルピリジン、3−メチルピリジン、4−メチルピリジン等のピコリン類、2−エチルピリジン、3−エチルピリジン、4−エチルピリジン等のエチルピリジン、2−ジメチルアミノピリジン、3−ジメチルアミノピリジン、4−ジメチルアミノピリジン等のジメチルアミノピリジン類、2,4−ジメチルピリジン、2,6−ジメチルピリジン等のルチジン類、α―ピコリン酸、β―ピコリン酸(ニコチン酸)、γ−ピコリン酸等のピコリン酸類、α―ピコリン酸アミド、β―ピコリン酸アミド(ニコチン酸アミド)、γ−ピコリン酸アミド等のピコリン酸アミド類、α―ピコリン酸メチル、β―ピコリン酸メチル(ニコチン酸メチル)、γ−ピコリン酸メチル等のピコリン酸エステル等が使用できる。中でもピコリンが好ましく、そのうちの3−メチルピリジンが最も好ましく用いられる。 Examples of the pyridine derivative represented by the formula I of the present invention include picolines such as 2-methylpyridine, 3-methylpyridine and 4-methylpyridine, and ethylpyridine such as 2-ethylpyridine, 3-ethylpyridine and 4-ethylpyridine. Dimethylaminopyridines such as 2-dimethylaminopyridine, 3-dimethylaminopyridine and 4-dimethylaminopyridine, lutidines such as 2,4-dimethylpyridine and 2,6-dimethylpyridine, α-picolinic acid, β- Picolinic acid (nicotinic acid), picolinic acids such as γ-picolinic acid, α-picolinic acid amide, β-picolinic acid amide (nicotinic acid amide), picolinic acid amides such as γ-picolinic acid amide, α-picolinic acid methyl , Picolinate such as methyl β-picolinate (methyl nicotinate) and methyl γ-picolinate You can use. Of these, picoline is preferred, and 3-methylpyridine is most preferred.
反応方法は式Iで示されるピリジン誘導体にデキストリンを分散させ、必要に応じて、着色防止目的で適量の水またはアルコ−ルを加えてから、脂肪酸ハライドまたは脂肪酸無水物を加えながら0℃から150℃で1時間から24時間かけて反応させる。このとき必要に応じ、N,N−ジメチルホルムアミドやN−メチル−2−ピロリドンのような水、メタノール、エタノール等の極性溶媒に可溶な反応溶媒で希釈することもできる。
反応終了後、メタノール、エタノール等の低級アルコールや水に分散し、デキストリン脂肪酸エステルを不溶画分として可溶画分に移行するピリジン誘導体と反応溶媒とを分離することにより精製することができる。さらに、減圧乾燥、流動乾燥等の既知の乾燥法による乾燥等により、水や洗浄溶媒である低級アルコールを除去し、必要に応じ粉砕してデキストリン脂肪酸エステルが得られる。
上記反応溶媒としては、N,N−ジメチルホルムアミド、ホルムアミド等のホルムアミド系、N,N−ジメチルアセトアミド、アセトアミド等のアセトアミド系、メチルエチルケトン、ジエチルケトン等のケトン系、酢酸エチル、酢酸−n−プロピル等のエステル系、テトラヒドロフラン、1,3−ジメチル−2−イミダゾリジノン、N−メチル2−ピロリドン、炭酸ジエチル、炭酸ジプロピル、炭酸エチレン、アセトニトリル、1,4−ジオキサン及び2−メチルピリジン、4−ジメチルアミノピリジン等の本発明式Iに示されるピリジンを含まないピリジン誘導体等を適宜使用することができる。
デキストリン脂肪酸エステルの製造において、一般的な反応の一例をピコリン及び脂肪酸クロライドを用いて示すと以下の通りである。下記式のAは互いに独立してRCO又はHである。
反応温度は原料脂肪酸等により適宜選択されるが、0℃以上から150℃の温度が好ましく、さらに、好ましくは50〜120℃である。
尚、本発明の「式Iで示されるピリジン誘導体存在下」とは式Iで示されるピリジン誘導体がアシル化のための反応触媒および反応溶媒として機能することを意味し、触媒機能としては〔化5〕に示されるように、脂肪酸ハライドまたは脂肪酸無水物を無駄なく、デキストリンのアシル化剤と働かせるためには、脂肪酸ハライドと脂肪酸無水物の総モル数と等モル数以上の式Iに示されるピリジン誘導体を使用することが好ましいと推測される。
In the reaction method, dextrin is dispersed in a pyridine derivative represented by the formula I, and if necessary, an appropriate amount of water or alcohol is added for the purpose of preventing coloring, and then 0 ° C. to 150 ° C. while adding a fatty acid halide or a fatty acid anhydride. The reaction is carried out at 1 ° C for 1 to 24 hours. At this time, it can also be diluted with a reaction solvent soluble in a polar solvent such as water, methanol, ethanol such as N, N-dimethylformamide or N-methyl-2-pyrrolidone, if necessary.
After completion of the reaction, it can be purified by dispersing in a lower alcohol such as methanol or ethanol or water and separating the reaction solvent from a pyridine derivative that migrates to a soluble fraction as a dextrin fatty acid ester as an insoluble fraction. Further, the dextrin fatty acid ester can be obtained by removing water and the lower alcohol as a washing solvent by drying by a known drying method such as reduced pressure drying or fluidized drying, and pulverizing as necessary.
Examples of the reaction solvent include formamides such as N, N-dimethylformamide and formamide, acetamides such as N, N-dimethylacetamide and acetamide, ketones such as methyl ethyl ketone and diethyl ketone, ethyl acetate, and acetic acid-n-propyl. Ester system, tetrahydrofuran, 1,3-dimethyl-2-imidazolidinone, N-methyl 2-pyrrolidone, diethyl carbonate, dipropyl carbonate, ethylene carbonate, acetonitrile, 1,4-dioxane and 2-methylpyridine, 4-dimethyl A pyridine derivative containing no pyridine represented by Formula I of the present invention, such as aminopyridine, can be used as appropriate.
An example of a general reaction in the production of dextrin fatty acid ester is shown below using picoline and fatty acid chloride. A in the following formula is RCO or H independently of each other.
The reaction temperature is appropriately selected depending on the starting fatty acid and the like, but a temperature of 0 ° C. or higher to 150 ° C. is preferable, and 50 to 120 ° C. is more preferable.
In the present invention, “in the presence of a pyridine derivative represented by formula I” means that the pyridine derivative represented by formula I functions as a reaction catalyst and a reaction solvent for acylation. 5] As shown in Formula I, the fatty acid halide or fatty acid anhydride can be used with an acylating agent for dextrin without waste, and the total number of moles of fatty acid halide and fatty acid anhydride is equal to or more than the number of moles. It is presumed that it is preferable to use a pyridine derivative.
次に本発明の新規デキストリン脂肪酸エステルを加えるオイルゲルについて詳述する。
本発明の新規デキストリン脂肪酸エステルをゲル化可能なオイルに配合する場合、その配合量は特に限定されないが、好ましくは0.1〜90重量%(以下、単に%で示す)、さらに好ましくは0.5〜50%である。
ゲル化可能なオイルとしては、例えば、流動パラフィン、イソパラフィン、スクワラン、ワセリン等の炭化水素系オイル、トリ−2−エチルヘキサン酸グリセリル、トリ(カプリル・カプロン酸)グリセリル、トリイソステアリン酸グリセリル、ジイソステアリン酸グリセリル等のグリセライド、トリイソステアリン酸ジグリセリル、テトライソステアリン酸ジグリセリル等のジグリセリン脂肪酸エステル、ジオクタン酸ネオペンチルグリコール、ジカプリン酸ネオペンチルグリコール等のネオペンチールグリコール脂肪酸エステル、ミリスチン酸イソプロピル、ステアリン酸ブチル、パルミチン酸2−エチルヘキシル、イソノナン酸イソノニル、イソノナン酸イソトリデシル、ステアリン酸ステアリル、ミリスチン酸イソステアリル、ミリスチン酸オクチルドデシル、オレイン酸オクチルドデシル、12−ヒドロキシステアリン酸コレステリル、ダイマ−ジリノ−ル酸(ジイソステアリル・フィトステアリル)、ジ水添ロジンダイマ−ジリノレイル、ジイソステアリン酸ダイマ−ジリノレイル、イソステアリン酸ダイマ−ジリノレイル、ダイマ−ジリノール酸ダイマ−ジリノレイル、ラウロイルグルタミン酸ジ(コレステリル/オクチルドデシル)、ラウロイルグルタミン酸ジ(コレステリル/ベヘニル/オクチルドデシル)、ラウロイルグルタミン酸ジオクチルドデシル等のエステル油、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸、ベヘニン酸、イソステアリン酸、エルカ酸、リノール酸、リノレン酸等の高級脂肪酸、オクチルアルコール、デシルアルコール、ラウリルアルコール、ミリスチルアルコール、セチルアルコール、ステアリルアルコール、ベヘニルアルコール、2−ヘキシルデカノール、2−オクチルデカノール、オレイルアルコール、イソステアリルアルコール等の高級アルコール、オリーブ油、椿油、大豆油、綿実油、ゴマ油、サフラワー油、小麦胚芽油、ヨクイニン油、米油、ホホバ油、ヒマシ油、亜麻仁油、コーン油、菜種油、椰子油、パーム油、スクワレン、液状ラノリン、ミンクオイル、卵黄油、羊毛油等の動植物油、パラフィンワックス、マイクロクリスタリンワックス、セレシンワックス、蜜ロウ、カルナウバワックス、キャンデリラワックス、硬化ヒマシ油、ロジン等のワックス類、ジメチルポリシロキサン、環状シリコーン、メチルフェニルポリシロキサン、変性シリコーン等のシリコーン油、有機溶剤としてはベンゼン、トルエン、キシレン等の芳香族化合物、クロロホルム、ジクロロメタン、ジクロロエタン等の塩素系化合物、ジオキサン、テトラハイドロフラン等のエーテル系化合物、ベンジルアルコール、フェノキシエタノール、カービトール類、セロソルブ類、ポリブテン、スピンドル油等を用いることができる。
Next, the oil gel to which the novel dextrin fatty acid ester of the present invention is added will be described in detail.
When the novel dextrin fatty acid ester of the present invention is blended in a gelable oil, the blending amount is not particularly limited, but is preferably 0.1 to 90% by weight (hereinafter simply expressed as%), more preferably 0.8. 5 to 50%.
Examples of oils that can be gelled include hydrocarbon oils such as liquid paraffin, isoparaffin, squalane, petrolatum, glyceryl tri-2-ethylhexanoate, glyceryl tri (capryl / caproic acid), glyceryl triisostearate, diisostearic acid Glyceride such as glyceryl, diglyceryl fatty acid ester such as diglyceryl triisostearate and diglyceryl tetraisostearate, neopentyl glycol fatty acid ester such as neopentyl glycol dioctanoate and neopentyl glycol dicaprate, isopropyl myristate, butyl stearate , 2-ethylhexyl palmitate, isononyl isononanoate, isotridecyl isononanoate, stearyl stearate, isostearyl myristate, milli Octyldodecyl tinate, octyldodecyl oleate, cholesteryl 12-hydroxystearate, dimer-dilinoleic acid (diisostearyl phytostearyl), dihydrogenated rosin dimer-dilinoleyl, diisostearic acid dimer-dilinoleyl, isostearic acid dimer-dilinoleyl , Dimer-dilinoleic acid dimer-dilinoleyl, lauroylglutamate di (cholesteryl / octyldodecyl), lauroylglutamate di (cholesteryl / behenyl / octyldodecyl), lauroylglutamate dioctyldodecyl, etc. ester oil, capric acid, lauric acid, myristic acid, palmitic acid, Higher fatty acids such as acid, stearic acid, oleic acid, behenic acid, isostearic acid, erucic acid, linoleic acid, linolenic acid, octyl alcohol Higher alcohols such as decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, 2-hexyl decanol, 2-octyl decanol, oleyl alcohol, isostearyl alcohol, olive oil, coconut oil, soybean oil, cottonseed oil, sesame oil, sacrificial oil Animal and vegetable oils such as flower oil, wheat germ oil, yokuinin oil, rice oil, jojoba oil, castor oil, linseed oil, corn oil, rapeseed oil, coconut oil, palm oil, squalene, liquid lanolin, mink oil, egg yolk oil, wool oil , Paraffin wax, microcrystalline wax, ceresin wax, beeswax, carnauba wax, candelilla wax, hardened castor oil, waxes such as rosin, dimethylpolysiloxane, cyclic silicone, methylphenylpoly Silicone oil such as siloxane and modified silicone, organic solvents such as aromatic compounds such as benzene, toluene and xylene, chlorine compounds such as chloroform, dichloromethane and dichloroethane, ether compounds such as dioxane and tetrahydrofuran, benzyl alcohol, phenoxyethanol Carbitols, cellosolves, polybutene, spindle oil and the like can be used.
本発明において、その他の添加剤としては、陽イオン性、陰イオン性、両性界面活性剤、非イオン性界面活性剤、薬剤、紫外線吸収剤、保湿剤、防腐剤、酸化防止剤、粉末類の酸化チタン、マイカ、カオリン、タルク、酸化鉄、群青、チタン酸コバルト等又はそれらの疎水化処理粉末、さらには有機顔料、染料、香料、メチルアルコール、エチルアルコール等の低級アルコール、水等、目的物の性能を損なわない程度に配合できる。 In the present invention, other additives include cationic, anionic, amphoteric surfactants, nonionic surfactants, drugs, ultraviolet absorbers, humectants, preservatives, antioxidants, powders Titanium oxide, mica, kaolin, talc, iron oxide, ultramarine, cobalt titanate, etc. or their hydrophobized powders, organic pigments, dyes, fragrances, lower alcohols such as methyl alcohol and ethyl alcohol, water, etc. Can be blended to such an extent that does not impair the performance.
ピリジンを用いて製造される従来のデキストリン脂肪酸エステルに対し、本発明のピリジン誘導体を用いて製造されるデキストリン脂肪酸エステルは上記のオイルに対する溶解性が向上し、100℃以内の加熱で完全に溶解し、冷却したゲルは均一で未溶解物が残らない。ピリジンを用いたものではデキストリン脂肪酸エステルのアシル基置換が均一でなく、偏ったものの集合体となっているのに対し、本発明のピリジン誘導体を用いたものではアシル基置換が均一なデキストリン脂肪酸エステルが得られていると推測される。本発明に至るまでの種々の実験によって得られた知見より、反応系にクロロホルム、ジクロロメタン、ジクロロエタン、ベンゼン、トルエン、キシレン、ヘキサン、ヘプタン等の非極性溶媒の添加をすることによって得られるデキストリン脂肪酸エステルはオイルへの溶解性は向上するが、オイルゲル化能力が無くなる。この理由として、反応がより均一に行なわれ、得られるデキストリン脂肪酸エステルのアシル基置換が均一過ぎるためであると考えられる。また、トリエチルアミン等の脂肪族3級アミンをピリジン代替として用いて得られたデキストリン脂肪酸エステルは反応が不均一過ぎてオイルに対する溶解性もゲル化力もピリジン存在下で反応したものより劣っていた。3級アミンと脂肪酸ハロゲン化物または脂肪酸無水物によるエステル化は多糖類をアシル化するのに有用な方法として紹介されているが、中でも平面的で窒素原子近傍に官能基が無く立体障害の少ないピリジンが最も反応性に富むことが説明されている。オイル溶解性、オイルゲル化力を兼ねたデキストリン脂肪酸エステル合成反応において適度な反応の均一性を求めたとしてもこの絶妙のバランスであるオイルに対する溶解性とゲル化力を両立するデキストリン脂肪酸エステルを得ることは容易ではない。このオイルに対する溶解性とゲル化力を両立するデキストリン脂肪酸エステルについて鋭意検討した結果、本発明に到達したものである。そして、異臭に関しても、本発明のピリジン誘導体を用いて製造されるデキストリン脂肪酸エステルはピリジンを用いて製造される従来のデキストリン脂肪酸エステルに比べてその異臭が低減されており、特に3−メチルピリジン、ニコチン酸、ニコチン酸メチル、ニコチン酸アミドを使用したものを用いた場合は殆ど異臭がしないものが得られる。このことは本発明の主用途である化粧品において非常に有用である。さらに、ニコチン酸、ニコチン酸アミドについてはビタミンとして人体に必須な成分であり、ピリジンに比べ人体に対する安全性が高いといえるものである。 Compared to the conventional dextrin fatty acid ester produced using pyridine, the dextrin fatty acid ester produced using the pyridine derivative of the present invention has improved solubility in the above oil and is completely dissolved by heating within 100 ° C. The cooled gel is uniform and no undissolved material remains. In the case of using pyridine, the acyl group substitution of the dextrin fatty acid ester is not uniform and is a collection of biased ones, whereas in the case of using the pyridine derivative of the present invention, the dextrin fatty acid ester has a uniform acyl group substitution. Is estimated to be obtained. Based on knowledge obtained through various experiments up to the present invention, dextrin fatty acid ester obtained by adding nonpolar solvent such as chloroform, dichloromethane, dichloroethane, benzene, toluene, xylene, hexane, heptane to the reaction system Although the solubility in oil is improved, the oil gelling ability is lost. The reason for this is considered to be that the reaction is carried out more uniformly and acyl group substitution of the resulting dextrin fatty acid ester is too uniform. Moreover, the dextrin fatty acid ester obtained by using an aliphatic tertiary amine such as triethylamine as a substitute for pyridine was too heterogeneous to be inferior in oil solubility and gelling power to those reacted in the presence of pyridine. Esterification with tertiary amines and fatty acid halides or fatty acid anhydrides has been introduced as a useful method for acylating polysaccharides. Among them, pyridine is planar and has no functional groups near the nitrogen atom and has little steric hindrance. Has been described as being the most reactive. Even if a suitable homogeneity of the reaction is required in the synthesis reaction of dextrin fatty acid ester that has both oil solubility and oil gelling power, it is possible to obtain a dextrin fatty acid ester that has both the solubility in oil and the gelling power, which is this exquisite balance. Is not easy. As a result of intensive investigations on dextrin fatty acid esters having both solubility in oil and gelling power, the present invention has been achieved. And also regarding the off-flavor, the dextrin fatty acid ester produced using the pyridine derivative of the present invention has a reduced off-flavor compared to the conventional dextrin fatty acid ester produced using pyridine, particularly 3-methylpyridine, When using nicotinic acid, methyl nicotinate, or nicotinamide, a product with almost no off-flavor is obtained. This is very useful in cosmetics which are the main use of the present invention. Furthermore, nicotinic acid and nicotinic acid amide are essential components for the human body as vitamins, and can be said to have higher safety for the human body than pyridine.
以下に実施例を挙げて、本発明を更に詳細に説明する。
デキストリン脂肪酸エステルの製造
合成例1
本発明における反応モル比とは、反応に供するデキストリンの無水グルコース単位(FW=162.14)当たりの反応に供する脂肪酸ハライドまたは脂肪酸無水物のモル数を示す。
デキストリン(平均糖重合度30)16.2gを3−メチルピリジン111gに分散させ、50℃にする。パルミチン酸クロライド82.5g(反応モル比3.0)を30分間滴下した。滴下終了後、反応温度を90℃として4時間反応させた。反応液をメタノールに沈澱させてからろ過し、固形分をメタノールで洗浄後、乾燥して、白色の粉体約80gを得た。得られた合成例1の生成物の乾燥減量は0.3%、酸価は1.9、平均アシル置換度はグルコース単位当たり2.1、アシル基モル比組成100%パルミトイル基であった。得られた合成例1の生成物の赤外吸収(IR)スペクトルは1740cm−1付近にエステル由来、2800〜3000cm−1付近にアルキル由来、1000〜1200cm−1付近に糖由来のピークを示した。このことからこの生成物がデキストリンパルミチン酸エステルであることが確認された。
Hereinafter, the present invention will be described in more detail with reference to examples.
Production synthesis example 1 of dextrin fatty acid ester
The reaction molar ratio in the present invention indicates the number of moles of fatty acid halide or fatty acid anhydride to be used for the reaction per anhydroglucose unit (FW = 162.14) of dextrin to be subjected to the reaction.
16.2 g of dextrin (average sugar polymerization degree 30) is dispersed in 111 g of 3-methylpyridine and brought to 50 ° C. 82.5 g of palmitic acid chloride (reaction molar ratio: 3.0) was added dropwise for 30 minutes. After completion of the dropping, the reaction temperature was 90 ° C. for 4 hours. The reaction solution was precipitated in methanol and then filtered, and the solid content was washed with methanol and dried to obtain about 80 g of a white powder. The product obtained in Synthesis Example 1 had a loss on drying of 0.3%, an acid value of 1.9, an average acyl substitution degree of 2.1 per glucose unit, and an acyl group molar ratio composition of 100% palmitoyl group. The obtained infrared absorption (IR) spectrum of the product of Synthesis Example 1 is derived from an ester near 1740 cm -1, alkyl from around 2800 to 3000 cm -1, and a peak derived from sugar in the vicinity of 1000 to 1200 -1 . This confirmed that the product was dextrin palmitate.
比較合成例1
デキストリン(平均糖重合度30)16.2gをピリジン111gに分散させ、50℃にする。パルミチン酸クロライド82.5g(反応モル比3.0)を30分間滴下した。滴下終了後、反応温度を90℃として4時間反応させた。反応液をメタノールに沈澱させてからろ過し、固形分をメタノールで洗浄後、乾燥して、白色の粉体約76gを得た。得られた比較合成例1の生成物の乾燥減量は0.3%、酸価は1.8、平均アシル置換度はグルコース単位当たり2.1、アシル基モル比組成100%パルミトイル基であった。
得られた比較合成例1の生成物の赤外吸収(IR)スペクトルは1740cm−1付近にエステル由来、2800〜3000cm−1付近にアルキル由来、1000〜1200cm−1付近に糖由来のピークを示した。このことからこの生成物がデキストリンパルミチン酸エステルであることが確認された。
Comparative Synthesis Example 1
16.2 g of dextrin (average sugar polymerization degree 30) is dispersed in 111 g of pyridine and brought to 50 ° C. 82.5 g of palmitic acid chloride (reaction molar ratio: 3.0) was added dropwise for 30 minutes. After completion of the dropping, the reaction temperature was 90 ° C. for 4 hours. The reaction solution was precipitated in methanol and then filtered, and the solid content was washed with methanol and dried to obtain about 76 g of a white powder. The resulting product of Comparative Synthesis Example 1 had a loss on drying of 0.3%, an acid value of 1.8, an average acyl substitution degree of 2.1 per glucose unit, and an acyl group molar ratio composition of 100% palmitoyl group. .
The obtained infrared absorption (IR) spectrum of the product of Comparative Synthesis Example 1 is derived from an ester near 1740 cm -1, alkyl from around 2800 to 3000 cm -1, a peak derived from sugar in the vicinity of 1000 to 1200 -1 It was. This confirmed that the product was dextrin palmitate.
溶解性試験及び臭い試験
デキストリン脂肪酸エステル40gを流動パラフィン60gに加え、室温で十分攪拌する。静かに攪拌しながら加温し、80、85、90℃でのデキストリン脂肪酸エステルの溶け残りを目視により確認する。同時に90℃での臭い評価を官能で行い確認した。
Solubility test and odor test 40 g dextrin fatty acid ester is added to 60 g liquid paraffin and stirred well at room temperature. Heat gently while stirring and visually check the undissolved residue of dextrin fatty acid ester at 80, 85 and 90 ° C. At the same time, the odor evaluation at 90 ° C. was confirmed by sensory evaluation.
目視による溶解性試験評価 5人のパネラーが評価(0〜3点)を行い、その平均点を下記のように記号で表した。
官能による臭い試験評価 5人のパネラーが評価(0〜3点)を行い、その平均点を下記のように記号で表した。
実施例及び比較例
合成例2〜22、比較合成例2〜3
以下の表に示す<反応条件>以外は合成例1と同様に操作して各種デキストリン脂肪酸エステルを得た。得られた生成物の<合成結果>と<物性・官能評価>を表に示す。
Synthesis Examples 2-22, Comparative Synthesis Examples 2-3
Except for the <reaction conditions> shown in the following table, various dextrin fatty acid esters were obtained in the same manner as in Synthesis Example 1. The <synthetic results> and <physical properties / sensory evaluation> of the obtained products are shown in the table.
本実施例で使用した分析機器及び分析方法は以下の通りであった。
IR分析
FT−IR:日本分光製FT/IR−470 Plusを用いKBr錠剤法により測定した。
HPLC分析
HPLC機器:
検出器 UV(紫外線吸収検出器)
カラム 資生堂 カプセルパックC18 4.6mmφ×250mm
溶離液 アセトニトリル/水によるグラジエント分析
サンプル作成方法:試料を水酸化カリウムエタノール溶液にて加水分解分解後、乾固し、18−クラウンエーテル触媒下、パラブロモフェナシルブロミドにより脂肪酸をパラブロモフェナシルエステル化UV254nm吸収強度を以ってHPLC測定した。内部標準物質としてペンタデカン酸等を使用した。各脂肪酸パラブロモフェナシルエステルのピーク面積比はパラブロモフェナシル基のモル比、つまり各脂肪酸のモル比を表すと考えた。
ゲル強度測定
本品5.0gを内径45mmの平底容器に精秤し、流動パラフィン(#70)45gを加えて分散させ、ゆるやかにかき混ぜながら90℃まで加熱して溶解する。その後直ちに30℃の恒温槽にて36時間静置しゲルを形成させる。このゲルを温度変化が生じないように手早くレオメーター(不動工業株式会社製、NRM−1002A)にセットし、次の条件でゲル強度を測定する。
測定条件
温度:30℃,
アダプター:φ20mm、厚さ2mmの円盤
架台上昇速度:6cm/min
チャート紙に得られるパターンは図1のようになり、初期のピーク即ち降伏値(a g)をゲル強度とする。尚、ゲル強度は温度の影響を著しく受けやすいため測定温度を厳密に調整する必要がある。
乾燥減量測定
試料として、本品2gを105℃で1時間乾燥させ、乾燥前後の重量差より求める
酸価測定
粧原基 一般試験法 酸価試験法 第2法に準じる。
ただし、試料として、本品3.0gをとり、溶媒は、エタノールとキシレンの等容量混液を用いる。
平均アシル基置換度
デキストリン脂肪酸エステルを約1.0g精秤し、6N水酸化ナトリウムを4ml、水を5ml、エタノールを25mlを加え、約80℃で2時間加熱還流し、完全にエステルを加水分解させる。6N塩酸で中和し、pH試験紙で酸性を確認する。ジエチルエーテルで中和された脂肪酸をジエチルエーテルで抽出し、分液ロートに移し、水50mlで5〜6回洗浄し、最終的に洗浄した水がpH試験紙で中性になるまで繰り返す。エーテル相を留去した後、0.1N水酸化カリウムエタノール溶液でフェノールフタレイン指示薬による中和滴定した。ただし、測定に供するデキストリン脂肪酸エステルの乾燥減量と酸価はそれぞれ、1%以下、2.5以下であるものを用いる。
デキストリン脂肪酸エステルA(g)中の脂肪酸の総モル数C=0.1×f×TV/1000
平均アシル基置換度(無水グルコース単位当たりの置換度で理論上0から3まで取り得る)=162.14×C/(A−C(M−18.01))
ただし、上記2式中の文字の意味を以下に定める。
デキストリン脂肪酸エステルの秤取量=A(g)
0.1N水酸化カリウムエタノール溶液のファクター=f
0.1N水酸化カリウムエタノール溶液の滴定量=TV(ml)
アシル化されている脂肪酸の分子量=M
デキストリン混合脂肪酸エステルの場合は、HPLCにより求めた各脂肪酸のモル比から平均脂肪酸分子量を算出して用いる。
The analytical instruments and analytical methods used in this example were as follows.
IR analysis FT-IR: Measured by KBr tablet method using FT / IR-470 Plus manufactured by JASCO Corporation.
HPLC analysis HPLC instrument:
Detector UV (ultraviolet absorption detector)
Column Shiseido Capsule Pack C18 4.6mmφ × 250mm
Eluent Gradient analysis with acetonitrile / water Sample preparation method: The sample was hydrolyzed with potassium hydroxide ethanol solution, dried to dryness, and the fatty acid was converted to parabromophenacyl ester with parabromophenacyl bromide under 18-crown ether catalyst. HPLC measurement was performed with the absorption UV 254 nm absorption intensity. Pentadecanoic acid or the like was used as an internal standard substance. The peak area ratio of each fatty acid parabromophenacyl ester was considered to represent the molar ratio of parabromophenacyl groups, that is, the molar ratio of each fatty acid.
Gel strength measurement
5.0 g of this product is precisely weighed in a flat bottom container having an inner diameter of 45 mm, 45 g of liquid paraffin (# 70) is added and dispersed, and heated to 90 ° C. while gently stirring to dissolve. Immediately after that, it is allowed to stand for 36 hours in a thermostatic bath at 30 ° C. to form a gel. This gel is quickly set on a rheometer (NRM-1002A, manufactured by Fudo Kogyo Co., Ltd.) so as not to cause a temperature change, and the gel strength is measured under the following conditions.
Measurement conditions Temperature: 30 ℃
Adapter: φ20mm, 2mm thick disk Mounting speed: 6cm / min
The pattern obtained on the chart paper is as shown in FIG. 1, and the initial peak, that is, the yield value (ag), is used as the gel strength. Since the gel strength is extremely susceptible to temperature, it is necessary to strictly adjust the measurement temperature.
Drying loss measurement As a sample, 2 g of this product is dried at 105 ° C. for 1 hour, and obtained from the weight difference before and after drying.
Acid value measurement Cosmetic primordium General test method Acid value test method According to the second method.
However, 3.0 g of this product is taken as a sample, and an equal volume mixture of ethanol and xylene is used as the solvent.
Average acyl group substitution degree About 1.0 g of dextrin fatty acid ester is precisely weighed, 4 ml of 6N sodium hydroxide, 5 ml of water and 25 ml of ethanol are added and heated to reflux at about 80 ° C. for 2 hours to completely hydrolyze the ester. Let Neutralize with 6N hydrochloric acid and check acidity with pH test paper. The fatty acid neutralized with diethyl ether is extracted with diethyl ether, transferred to a separatory funnel, washed 5 to 6 times with 50 ml of water, and repeated until the finally washed water becomes neutral with pH test paper. After the ether phase was distilled off, neutralization titration with a phenolphthalein indicator was performed with a 0.1N potassium hydroxide ethanol solution. However, the weight loss on drying and the acid value of the dextrin fatty acid ester used for the measurement are 1% or less and 2.5 or less, respectively.
Total number of moles of fatty acids in dextrin fatty acid ester A (g) C = 0.1 × f × TV / 1000
Average acyl group substitution degree (theoretical substitution degree per anhydroglucose unit can be 0 to 3) = 162.14 × C / (A-C (M-18.01))
However, the meaning of the characters in the above two formulas is defined below.
Weighed amount of dextrin fatty acid ester = A (g)
Factor of 0.1N potassium hydroxide ethanol solution = f
Titration of 0.1N potassium hydroxide ethanol solution = TV (ml)
Molecular weight of acylated fatty acid = M
In the case of dextrin mixed fatty acid ester, the average fatty acid molecular weight is calculated from the molar ratio of each fatty acid determined by HPLC.
配合例1
合成例1で得たデキストリンパルミチン酸エステルを用いて乳液(O/W)を作成した。
1.モノステアリン酸ポリオキシエチレンソルビタン(20.E.O.)1.0部
2.テトラオレイン酸ポリオキシエチレンソルビット(60.E.O.)0.5部
3.モノステアリン酸グリセリル 1.0部
4.ステアリン酸 0.5部
5.ベヘニルアルコール 0.5部
6.流動パラフィン 4.0部
7.トリオクタン酸グリセリル 4.0部
8.2−エチルヘキサン酸セチル 2.0部
9.デキストリンパルミチン酸エステル(合成例1)3.0部
10.1,3−ブチレングリコール 5.0部
11.カルボキシビニルポリマー 0.05部
12.水酸化ナトリウム 0.025部
13.防腐剤 適量
14.香料 適量
15.精製水 残量
(製法)(A)成分10〜13、15の一部を70℃にて均一に加熱溶解する。(B)成分1〜9を70℃にて均一に加熱溶解する。(C)AにBを添加して乳化した。(D)Cに成分11及び15の残部を加えて冷却し、成分14を加えて乳液を得た。
上記乳液は硬い未溶解物が残らない、滑らかでアミン異臭の感じられない、なじみが良く、しっとり感に優れたものであった。
Formulation Example 1
An emulsion (O / W) was prepared using the dextrin palmitate ester obtained in Synthesis Example 1.
1. 1. 1.0 part of polyoxyethylene sorbitan monostearate (20.EO) 2. 0.5 part of polyoxyethylene sorbitol tetraoleate (60.EO) 1. Glyceryl monostearate 1.0 part Stearic acid 0.5 part5. Behenyl alcohol 0.5 part6. Liquid paraffin 4.0 parts7. Glyceryl trioctanoate 4.0 parts 8.2 Cetyl 2-ethylhexanoate 2.0 parts 9. Dextrin palmitate (Synthesis Example 1) 3.0 parts 10.1,3-butylene glycol 5.0 parts11. Carboxyvinyl polymer 0.05 part 12. Sodium hydroxide 0.025 part13. Preservative appropriate amount14. Perfume appropriate amount 15. Remaining amount of purified water (Production method) (A) A part of components 10 to 13 and 15 are heated and dissolved uniformly at 70 ° C. (B) Components 1 to 9 are heated and dissolved uniformly at 70 ° C. (C) B was added to A and emulsified. (D) The remainder of components 11 and 15 was added to C and cooled, and component 14 was added to obtain an emulsion.
The above-mentioned emulsion had no hard undissolved material, was smooth and did not feel an amine odor, was well-familiar, and had a moist feeling.
配合例2
合成例3で得たデキストリンパルミチン酸エステルを用いてW/Oクリームを作成した。
1.セスキオレイン酸ソルビタン 3.0部
2.モノステアリン酸グリセリル 4.0部
3.モノステアリン酸ポリエチレングリコール(40E.O.) 2.0部
4.セチルアルコール 2.0部
5.デキストリンパルミチン酸エステル(合成例3) 15.0部
6.スクワラン 3.0部
7.1,3−ブチレングリコール 10.0部
8.防腐剤 適量
9.香料 適量
10.精製水 残量
(製法)(A)成分1〜6を70℃にて均一に加熱溶解する。(B)成分7,8,10を70℃にて均一に加熱溶解する。(C)AにBを添加して乳化し、冷却した後、成分9を添加してクリームを得る。上記クリームは硬い未溶解物が残らない、滑らかでアミン異臭の感じられない、延展性及びなじみに優れ、経時安定性の良いものであった。
Formulation Example 2
A W / O cream was prepared using the dextrin palmitate ester obtained in Synthesis Example 3.
1. Sorbitan sesquioleate 3.0 parts 4.0 parts glyceryl monostearate Polyethylene glycol monostearate (40E.O.) 2.0 parts 4. Cetyl alcohol 2.0 parts 5. Dextrin palmitate (Synthesis Example 3) 15.0 parts 6. Squalane 3.0 parts 7.1,3-butylene glycol 10.0 parts 8. Preservative appropriate amount 9. Perfume appropriate amount 10. Purified water Remaining amount (Production method) (A) Components 1 to 6 are uniformly dissolved by heating at 70 ° C. (B) Components 7, 8, and 10 are uniformly dissolved by heating at 70 ° C. (C) After adding B to A and emulsifying and cooling, component 9 is added to obtain a cream. The above cream had no hard undissolved product, was smooth and did not feel an amine odor, was excellent in spreadability and familiarity, and had good stability over time.
配合例3
合成例12で得たデキストリン(パルミチン酸/2−エチルヘキサン酸)エステルおよび合成例1で得たデキストリンパルミチン酸エステルを用いてファンデーションを作成した。
1.デキストリン(パルミチン酸/2−エチルヘキサン酸)エステル(合成例12) 13.0部
2.デキストリンパルミチン酸エステル(合成例1) 2.0部
3.セレシン 8.0部
4.流動パラフィン 残量
5.メチルフェニルポリシロキサン 9.0部
6.香料 適量
7.色材 適量
(製法)(A)成分1〜5を均一に加熱溶解する。(B)Aに成分7を加えて均一分散し、さらに成分6を添加してファンデーションを得る。上記ファンデーションは硬い未溶解物が残らない、滑らかでアミン異臭の感じられない、延展性及びもちに優れ、経時安定性の良いものであった。
Formulation Example 3
A foundation was prepared using the dextrin (palmitic acid / 2-ethylhexanoic acid) ester obtained in Synthesis Example 12 and the dextrin palmitate ester obtained in Synthesis Example 1.
1. Dextrin (palmitic acid / 2-ethylhexanoic acid) ester (Synthesis Example 12) 13.0 parts 2. Dextrin palmitate ester (Synthesis example 1) 2.0 parts Ceresin 8.0 parts 4. 4. Liquid paraffin remaining Methylphenylpolysiloxane 9.0 parts 6. Perfume appropriate amount 7. Color material Appropriate amount (production method) (A) Components 1 to 5 are uniformly heated and dissolved. (B) Add component 7 to A and uniformly disperse, and then add component 6 to obtain a foundation. The above foundation had no hard undissolved material, was smooth and did not feel an amine odor, had excellent spreadability and durability, and had good stability over time.
配合例4
合成例1で得たデキストリンパルミチン酸エステルを用いて口紅を作成した。
1.マイクロクリスタリンワックス 5.0部
2.ジペンタエリトリット脂肪酸エステル 5.0部
3.ポリブテン 10.0部
4.ラノリン酸オクチルドデシル 30.0部
5.2−エチルヘキサン酸セチル 10.0部
6.デキストリンパルミチン酸エステル(合成例1) 20.0部
7.ジグリセリントリイソステアレート 12.0部
8.色材 適量
9.香料 適量
(製法)(A)成分1〜9を加熱溶解し、ローラーにて混練し、容器に流し込んで冷却し、口紅を得る。
上記口紅は硬い未溶解物が残らない、滑らかでアミン異臭の感じられない、延展性及び付着性に優れ、経時安定性の良いものであった。
Formulation Example 4
A lipstick was prepared using the dextrin palmitate ester obtained in Synthesis Example 1.
1. Microcrystalline wax 5.0 parts 2. Dipentaerythritol fatty acid ester 5.0 parts Polybutene 10.0 parts 4. 5. Octyldodecyl lanolinate 30.0 parts 5. Cetyl 2-ethylhexanoate 10.0 parts 6. Dextrin palmitate (Synthesis Example 1) 20.0 parts Diglycerin triisostearate 12.0 parts 8. Appropriate amount of coloring material9. Perfume Appropriate amount (Manufacturing method) (A) Components 1 to 9 are heated and dissolved, kneaded with a roller, poured into a container and cooled to obtain a lipstick.
The lipstick did not leave a hard undissolved substance, was smooth and did not feel an amine odor, was excellent in spreadability and adhesion, and had good stability over time.
配合例5
合成例13で得たデキストリン(パルミチン酸/イソステアリン酸)エステルを用いてアイライナーを作成した。
1.マイクロクリスタリンワックス 6.0部
2.カルナウバワックス 4.0部
3.デキストリン(パルミチン酸/イソステアリン酸)エステル(合成例13)20.0部
4.シリコーン系グラフト重合体(固型分) 4.0部
5.有機性ベントナイト 1.5部
6.無水ケイ酸 1.5部
7.プロピレンカーボネート 0.5部
8.低沸点イソパラフィン系炭化水素油 残量
9.色材 適量
(製法)成分1〜9を加熱溶解し、ローラー処理をしてアイライナーを得る。
上記アイライナーは硬い未溶解物が残らない、滑らかでアミン異臭の感じられない、皮膜形成性及び延展性に優れ、経時安定性の良いものであった。
Formulation Example 5
An eyeliner was prepared using the dextrin (palmitic acid / isostearic acid) ester obtained in Synthesis Example 13.
1. Microcrystalline wax 6.0 parts Carnauba wax 4.0 parts 3. Dextrin (palmitic acid / isostearic acid) ester (Synthesis Example 13) 20.0 parts 4. Silicone graft polymer (solid component) 4.0 parts Organic bentonite 1.5 parts 6. Silicic acid 1.5 parts 7. Propylene carbonate 0.5 part 8. 8. Low boiling point isoparaffinic hydrocarbon oil remaining amount Appropriate amount of coloring material (Manufacturing method) Components 1 to 9 are heated and dissolved, and roller treatment is performed to obtain an eyeliner.
The eyeliner did not leave a hard undissolved product, was smooth and did not feel an amine odor, was excellent in film formation and spreadability, and had good stability over time.
配合例6
合成例10で得たデキストリンミリスチン酸エステルを用いてマスカラを作成した。
1.ステアリン酸 2.0部
2.ミツロウ 3.0部
3.セタノール 1.0部
4.デキストリンミリスチン酸エステル(合成例10) 10.0部
5.モノオレイン酸ポリオキシエチレンソルビタン(20E.O.) 1.0部
6.セスキオレイン酸ソルビタン 0.5部
7.色材 適量
8.トリエタノールアミン 1.0部
9.防腐剤 適量
10.ポリアクリル酸エステルエマルジョン 40.0部
11.精製水 残量
(製法)(A)成分1〜6を70℃にて加熱溶解し、成分7を加えて均一に混合する。(B)成分8〜11を70℃にて均一に加熱溶解する。(C)AにBを添加して乳化後、冷却して容器に充填してマスカラを得る。
上記マスカラは硬い未溶解物が残らない、滑らかでアミン異臭の感じられない、皮膜形成性に優れ、もちのよいものであった。
Formulation Example 6
A mascara was prepared using the dextrin myristic acid ester obtained in Synthesis Example 10.
1. Stearic acid 2.0 parts 3. Beeswax 3.0 parts Cetanol 1.0 part 4. Dextrin myristic acid ester (Synthesis example 10) 10.0 parts 5. Monooleic acid polyoxyethylene sorbitan (20E.O.) 1.0 part 6. 6. Sorbitan sesquioleate 0.5 part Appropriate amount of coloring material 8. Triethanolamine 1.0 part 9. Preservative appropriate amount 10. 10. Polyacrylic ester emulsion 40.0 parts Remaining amount of purified water (Manufacturing method) (A) Components 1 to 6 are dissolved by heating at 70 ° C., and component 7 is added and mixed uniformly. (B) Components 8 to 11 are heated and dissolved uniformly at 70 ° C. (C) After adding B to A and emulsifying, it is cooled and filled into a container to obtain a mascara.
The mascara had no hard undissolved material, was smooth and did not feel an amine odor, was excellent in film-forming properties, and had a good texture.
配合例7
合成例1で得たデキストリンパルミチン酸エステルを用い透明リップグロスを作成した。
1.デキストリンパルミチン酸エステル(合成例1) 15部
2.流動パラフィン 15部
3.水添ポリブテン 20部
4.ダイマ−ジリノ−ル酸ダイマ−ジリノ−ル 10部
5.ダイマージリノール酸ジ(イソステアリル/フィトステアリル) 10部
6.ラウロイルグルタミン酸ジ(コレステリル/オクチルドデシル) 10部
7.イソステアリン酸ダイマ−ジリノ−ル 10部
8.ラウロイルグルタミン酸ジ(コレステリル/ベヘニル/オクチルドデシル)10部
9. 色材 適量
10.ジメチコン 0.1部
(製法)成分1を成分2に室温で分散させ、90℃まで攪拌溶解させ、成分2から成分9までを加え、攪拌しながら90℃まで加熱する。成分9を加え消泡し、80℃で皿型容器に充填した。これを24時間室温で静置して固形透明リップグロスを得る。硬い未溶解物が残らない、滑らかでアミン異臭の感じられないリップグロスであった。
Formulation Example 7
A transparent lip gloss was prepared using the dextrin palmitate ester obtained in Synthesis Example 1.
1. Dextrin palmitate ester (Synthesis example 1) 15 parts2. Liquid paraffin 15 parts3. Hydrogenated polybutene 20 parts4. Dimer dilinoleic acid dimer dilinol 10 parts5. Dimer dilinoleic acid di (isostearyl / phytostearyl) 10 parts6. 6. Lauroyl glutamate di (cholesteryl / octyldodecyl) 10 parts 7 parts of isostearic acid dimer dilinol 8. 10 parts dilauroyl glutamate (cholesteryl / behenyl / octyldodecyl) Coloring material appropriate amount10. Dimethicone 0.1 part (preparation method) Component 1 is dispersed in Component 2 at room temperature, dissolved by stirring to 90 ° C, added from Component 2 to Component 9, and heated to 90 ° C while stirring. Ingredient 9 was added to eliminate foam, and the dish-shaped container was filled at 80 ° C. This is left still for 24 hours at room temperature to obtain a solid transparent lip gloss. It was a smooth, lip gloss that did not leave a hard undissolved substance and did not feel an amine odor.
配合例8
合成例13で得たデキストリンパルミチン酸/イソステアリン酸エステル及び合成例5で得たデキストリンパルミチン酸エステルを用いファンデーションを作成した。
1.デキストリンパルミチン酸/イソステアリン酸エステル(合成例13) 20部
2.イソパラフィン 50部
3.イソノナン酸イソトリデシル 10部
4.マイカ 4部
5.10%デキストリンパルミチン酸エステル(合成例5)表面処理酸化チタン 5部
6.8%デキストリンパルミチン酸エステル(合成例5)表面処理酸化鉄 5部
7.6%デキストリンパルミチン酸エステル(合成例5)表面処理セリサイト 5部
8.ポリエチレングリコール 1部
(製法)成分1を成分2および成分2に室温で分散させ、60℃まで攪拌溶解させ、成分3から成分8までを加え、攪拌しながら75℃まで攪拌加熱する。ガラス容器に充填し、冷却し、ゲル状ファンデーションを得る。硬い未溶解物が残らない、滑らかでアミン異臭の感じられない清涼感があるファンデーションであった。
Formulation Example 8
A foundation was prepared using the dextrin palmitic acid / isostearic acid ester obtained in Synthesis Example 13 and the dextrin palmitic acid ester obtained in Synthesis Example 5.
1. Dextrin palmitic acid / isostearic acid ester (Synthesis Example 13) 20 parts2. Isoparaffin 50 parts3. Isotridecyl isononanoate 10 parts4. Mica 4 parts 5.10% dextrin palmitate (Synthesis Example 5) surface treated titanium oxide 5 parts 6.8% dextrin palmitate (Synthesis Example 5) surface treated iron oxide 5 parts 7.6% dextrin palmitate ( Synthesis Example 5) Surface-treated sericite 5 parts8. Polyethylene glycol 1 part
(Manufacturing method) Component 1 is dispersed in component 2 and component 2 at room temperature, dissolved by stirring to 60 ° C, added from component 3 to component 8, and stirred and heated to 75 ° C while stirring. A glass container is filled and cooled to obtain a gel-like foundation. It was a smooth foundation that had no undissolved hard residue and had a refreshing sensation that did not give off an amine odor.
配合例9
合成例1で得たデキストリンパルミチン酸エステルを用いて印刷用インキ(枚葉平板インキ)を作成した。
1.デキストリンパルミチン酸エステル(合成例1) 2.0部
2.カーボンブラック(MA−8:三菱化成) 20.0部
3.アルカリブルートナーペースト(C.I.42750:1) 4.0部
4.フタロシアンブルー(JIS K 5241) 2.0部
5.フェノール樹脂ワニス(ヒタノール1501:日立化成工業)45.0部
6.アマニ油ワニス(JIS K 5421) 12.0部
7.流動パラフィン(シルコールP−70:松村石油) 13.0部
8.マンガンドライヤー(JIS K 8997・64:日本化学産業)
2.0部
(製法)(A)成分1と7を80℃で加熱溶解する。(B)Aに成分2〜6及び8を順次加えて、常温で良く練り合わせて枚葉平板インキを作成した。
上記枚葉平板インキは分散安定性に優れ、印刷に際し適度な粘度を与え、チキソトロピー性を示し、均一な薄膜となって板に移すことができる印刷特性の優れたインキであった。
Formulation Example 9
A printing ink (sheet-fed flat plate ink) was prepared using the dextrin palmitate ester obtained in Synthesis Example 1.
1. Dextrin palmitate (Synthesis Example 1) 2.0 parts Carbon black (MA-8: Mitsubishi Kasei) 20.0 parts3. 4. Alkali blue toner paste (C.I. 42750: 1) 4.0 parts 4. Phthalocyan Blue (JIS K 5241) 2.0 parts Phenolic resin varnish (Hitanol 1501: Hitachi Chemical) 45.0 parts Linseed oil varnish (JIS K 5421) 12.0 parts Liquid paraffin (Silcol P-70: Matsumura Oil) 13.0 parts8. Manganese dryer (JIS K 8997/64: Nippon Chemical Industry)
2.0 parts (production method) (A) Components 1 and 7 are heated and dissolved at 80 ° C. (B) Components 2 to 6 and 8 were sequentially added to A and kneaded well at room temperature to prepare a sheet-fed flat plate ink.
The sheet-fed flat plate ink was excellent in dispersion stability, gave an appropriate viscosity during printing, exhibited thixotropy, and had excellent printing characteristics that could be transferred to a plate as a uniform thin film.
配合例10
合成例2で得たデキストリンパルミチン酸エステルを用いて、金属用油性白色塗料を作成した。
1.デキストリンパルミチン酸エステル(合成例2) 1.5部
2.チタン白(MT500B:ティカ) 60.0部
3.脱水ヒマシ油変性アルキッド樹脂ワニス 33.0部
4.流動パラフィン(シルコールP−70:松村石油) 5.0部
5.マンガンドライヤー(JIS K 8997・64:日本化学産業) 0.5部
(製法)(A)成分1と4を80℃にて加熱溶解し、成分3,2,5を順次加えた後、常温でよく練り合わせて金属用油性白色塗料を作成した。
上記金属用油性白色塗料は分散安定性に優れ、また使用時には少量のテレピン油や溶剤を添加して撹拌することにより、大きく粘度が低下し、塗装作業に適した粘度となる。ハケ塗りの場合、塗り延ばしやすく、厚塗りができ、ハケ目が残りにくく、また、タレにくい等の塗料として優れた粘性の塗料であった。
Formulation Example 10
Using the dextrin palmitate ester obtained in Synthesis Example 2, an oily white paint for metal was prepared.
1. Dextrin palmitate (Synthesis Example 2) 1.5 parts 2. Titanium white (MT500B: Tika) 60.0 parts 3. 33.0 parts of dehydrated castor oil-modified alkyd resin varnish Liquid paraffin (Silcol P-70: Matsumura Oil) 5.0 parts5. Manganese dryer (JIS K 8997 · 64: Nippon Chemical Industry Co., Ltd.) 0.5 parts (Manufacturing method) (A) Components 1 and 4 are heated and dissolved at 80 ° C., components 3, 2, and 5 are added sequentially, and then at room temperature. Kneaded well to create an oily white paint for metal.
The oily white paint for metal is excellent in dispersion stability, and when used, a small amount of turpentine oil or a solvent is added and stirred, so that the viscosity is greatly reduced, and the viscosity becomes suitable for coating work. In the case of brush coating, it was a viscous paint excellent as a paint that was easy to spread, thick coating was difficult to leave, and it was difficult to sag.
本発明のピリジン誘導体の存在下で得られた実施例のデキストリン脂肪酸エステルは、ピリジンの存在下で得られた比較例のデキストリン脂肪酸エステルに比しオイル溶解性に優れ、そのオイルゲル中未溶解物が少ない。更に異臭も少ない。 The dextrin fatty acid ester of the example obtained in the presence of the pyridine derivative of the present invention is superior in oil solubility to the dextrin fatty acid ester of the comparative example obtained in the presence of pyridine, and the undissolved substance in the oil gel is Few. Furthermore, there is little off-flavor.
Claims (6)
特性1
デキストリン骨格の平均単糖重合度が10〜150であるデキストリン脂肪酸エステル
特性2
平均アシル基置換度がグルコース単位当たり1.0以上であるデキストリン脂肪酸エステル
特性3
アシル基が、炭素数12〜22の直鎖飽和アシル基、炭素数4〜26の分岐アシル基、炭素数6〜30の不飽和アシル基及び/又は炭素数2〜11の直鎖飽和アシル基からなり、かつ、アシル基のモル比組成において、炭素数12〜22の直鎖飽和アシル基が少なくとも50%以上を構成するデキストリン脂肪酸エステル
Characteristic 1
Characteristic 2 of dextrin fatty acid ester having an average monosaccharide polymerization degree of dextrin skeleton of 10 to 150
Dextrin fatty acid ester characteristic 3 with an average acyl group substitution degree of 1.0 or more per glucose unit
The acyl group is a linear saturated acyl group having 12 to 22 carbon atoms, a branched acyl group having 4 to 26 carbon atoms, an unsaturated acyl group having 6 to 30 carbon atoms, and / or a linear saturated acyl group having 2 to 11 carbon atoms. And a dextrin fatty acid ester in which the linear saturated acyl group having 12 to 22 carbon atoms constitutes at least 50% or more in the molar ratio composition of the acyl group
特性1
デキストリン骨格の平均単糖重合度が10〜150であるデキストリン脂肪酸エステル
特性2
平均アシル基置換度がグルコース単位当たり1.0以上であるデキストリン脂肪酸エステル
特性3
アシル基が、炭素数12〜22の直鎖飽和アシル基、炭素数4〜26の分岐アシル基、炭素数6〜30の不飽和アシル基及び/又は炭素数2〜11の直鎖飽和アシル基からなり、かつ、アシル基のモル比組成において、炭素数12〜22の直鎖飽和アシル基が少なくとも50%以上を構成するデキストリン脂肪酸エステル。 A method for producing a dextrin fatty acid ester satisfying the following characteristics 1 to 3, characterized in that dextrin and a fatty acid halide or a fatty acid anhydride are esterified in the presence of a pyridine derivative represented by the formula I.
Characteristic 1
Characteristic 2 of dextrin fatty acid ester having an average monosaccharide polymerization degree of dextrin skeleton of 10 to 150
Dextrin fatty acid ester characteristic 3 with an average acyl group substitution degree of 1.0 or more per glucose unit
The acyl group is a linear saturated acyl group having 12 to 22 carbon atoms, a branched acyl group having 4 to 26 carbon atoms, an unsaturated acyl group having 6 to 30 carbon atoms, and / or a linear saturated acyl group having 2 to 11 carbon atoms. And a dextrin fatty acid ester in which the linear saturated acyl group having 12 to 22 carbon atoms constitutes at least 50% or more in the molar ratio composition of the acyl group.
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