JP6002730B2 - 防腐剤組成物 - Google Patents
防腐剤組成物 Download PDFInfo
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- JP6002730B2 JP6002730B2 JP2014203103A JP2014203103A JP6002730B2 JP 6002730 B2 JP6002730 B2 JP 6002730B2 JP 2014203103 A JP2014203103 A JP 2014203103A JP 2014203103 A JP2014203103 A JP 2014203103A JP 6002730 B2 JP6002730 B2 JP 6002730B2
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- antiseptic
- component
- acid ester
- composition
- alcohol
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- 229920000656 polylysine Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- ISYUCUGTDNJIHV-UHFFFAOYSA-N propyl 2-bromoacetate Chemical compound CCCOC(=O)CBr ISYUCUGTDNJIHV-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229960000414 sodium fluoride Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-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
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
〔1〕 下記式(1):
〔2〕 前記〔1〕に記載の芳香族アルコールが芳香族の第一級アルコールであることを特徴とするカビに対する防腐剤組成物。
〔3〕 前記芳香族の一級アルコールが、フェノキシエタノール及びフェネチルアルコールからなる群より選ばれた少なくとも1種の化合物であることを特徴とする前記〔2〕に記載のカビに対する防腐剤組成物。
〔4〕 前記〔1〕〜〔3〕のいずれかに記載のカビに対する防腐剤組成物を含有する化粧品。
〔5〕 前記〔1〕〜〔3〕のいずれかに記載の防腐剤組成物を食品、食器類、香粧品、化粧品、皮膚外用剤、口腔衛生製品、医薬部外品、生活衛生用品、衣類、塗料およびペット衛生用品から選ばれる防腐対象物に配合して、該防腐対象物のカビに対する防腐力を高める方法。
(1)1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル((a−1)成分)の合成例
(1−1)レフォルマトスキー反応によるβ−ヒドロキシデカン酸メチルエステルの合成例
300mlの四口丸底フラスコに亜鉛6.5g、オクタナール15.5g、トリメトキシボラン25mlおよび乾燥THF25mlを入れ、20℃、窒素気流下で2時間かけてブロモ酢酸メチル17.5gを滴下した。滴下後、20℃で1時間撹拌したのち、飽和アンモニア水溶液25mlとグリセリン25mlを加えて10分撹拌した。有機層を分離し、水溶液層をジエチルエーテルで2回抽出した。その後、有機溶液を集めて脱溶媒を行い、残分を蒸留で精製してβ−ヒドロキシデカン酸メチルエステルを得た。
50ml耐圧バイアル瓶に上記で得られたβ−ヒドロキシデカン酸メチルエステル5g、1,3−プロパンジオール5g、固定化リパーゼ(製品名 Novozyme435:ノボザイムズジャパン株式会社)を0.05g添加し、50℃、10mmHgの減圧下で24時間撹拌を行った。反応後、得られた反応液をシリカゲルカラムクロマトグラフィーにより精製を行った結果、純度99%の1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステルを得た。
表1に示す処方で、POE(20)ステアレート、テトラオレイン酸POE(40)ソルビット、モノステアリン酸グリセリン、スクワラン、グリセリントリオクタノエート、1,3−ブチレングリコール、グリセリン、キサンタンガムおよび精製水を含有する化粧品成分に対して、1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル((a−1)成分)とフェノキシエタノール((b)成分)を配合した乳液(実施例1)、1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル((a−1)成分)とフェネチルアルコール((c)成分)を配合した乳液(実施例2)、(a−1)成分を配合した乳液(比較例1)、(b)成分を配合した乳液(比較例2)、(c)成分を配合した乳液(比較例3)、1,2−ペンタンジオールを配合した乳液(比較例5)、(b)成分と1,2−ペンタンジオールを配合した乳液(比較例6)を作製し、後述するチャレンジテストにより防腐力を評価した。なお、対照として上記いずれの防腐剤成分も配合しない乳液(比較例4)を用いた。
(化粧水の配合処方)
グリセリン 5.00重量%
ジプロピレングリコール(DPG) 3.00
POE(60)硬化ヒマシ油 0.60
クエン酸Na 0.15
クエン酸 0.01
グリシン 0.20
アラニン 0.10
ヒアルロン酸Na 0.01
1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル
0.25
フェノキシエタノール 0.25
精製水 残部
(製法)
グリセリン、DPG、POE(60)硬化ヒマシ油、1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル、フェノキシエタノールを混合し、70℃に加熱溶解した(これを混合物Aとする)。一方、クエン酸Na、クエン酸、グリシン、アラニン、ヒアルロン酸Na、水をそれぞれ室温で混合した(これを混合物Bとする)。続いて、混合物Aと混合物Bを合わせて50℃で混合し、化粧水を得た。
(配合特性)
1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル、フェノキシエタノールは他の成分と容易に混和した。得られた化粧水には濁りや析出は見られなかった。
セタノール 1.00重量%
スクワラン 4.00
ステアリン酸 1.00
モノステアリン酸ポリエチレングリコール(25EO) 3.20
グリセリンステアリン酸モノエステル 1.00
1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル 0.25
フェノキシエタノール 0.25
γ−トコフェロール 0.05
BHT(酸化防止剤) 0.01
1,3−ブタンジオール 3.00
カルボキシビニルポリマー 0.20
水酸化カリウム 0.20
精製水 残部
(製法)
セタノール、スクワラン、ステアリン酸、γ−トコフェロール、BHT、モノステアリン酸ポリエチレングリコール(25EO)、グリセリンステアリン酸モノエステル、1,3−プロパンジオールモノβ−ヒドロキシデカン酸エステル、フェノキシエタノールをそれぞれ混合し70℃に加温溶解した(これを混合物Aとする)。一方、1,3−ブタンジオール、カルボキシビニルポリマー、水酸化カリウムをそれぞれ室温下で混合した(これを混合物Bとする)。続いて、混合物Aと混合物Bを合わせて60℃に加温し精製水中に少量ずつ添加しながら激しく攪拌し乳化して乳液を得た。
(配合特性)
本発明品は他の成分と直ちに混和した。得られた乳液には分離や析出は見られなかった。
Claims (5)
- 前記芳香族アルコールが芳香族の第一級アルコールであること
を特徴とする請求項1記載のカビに対する防腐剤組成物。 - 前記芳香族の一級アルコールが、フェノキシエタノール及びフェネチルアルコールからなる群より選ばれた少なくとも1種の化合物であること
を特徴とする請求項2に記載のカビに対する防腐剤組成物。 - 請求項1〜3のいずれかに記載のカビに対する防腐剤組成物を含有する化粧品。
- 請求項1〜3のいずれかに記載の防腐剤組成物を食品、食器類、香粧品、化粧品、皮膚外用剤、口腔衛生製品、医薬部外品、生活衛生用品、衣類、塗料およびペット衛生用品から選ばれる防腐対象物に配合して、該防腐対象物のカビに対する防腐力を高める方法。
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