JP6120845B2 - イソソルビドモノエステルと、少なくとも1個の芳香族基を含有するアルコールとを含有する組成物 - Google Patents
イソソルビドモノエステルと、少なくとも1個の芳香族基を含有するアルコールとを含有する組成物 Download PDFInfo
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- JP6120845B2 JP6120845B2 JP2014523229A JP2014523229A JP6120845B2 JP 6120845 B2 JP6120845 B2 JP 6120845B2 JP 2014523229 A JP2014523229 A JP 2014523229A JP 2014523229 A JP2014523229 A JP 2014523229A JP 6120845 B2 JP6120845 B2 JP 6120845B2
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Description
a)1種または複数の式(I)の化合物と、
Rは、5〜11個、好ましくは7〜9個、および特に好ましくは7個の炭素原子を有する直鎖状もしくは分枝状の飽和アルキル基または5〜11個、好ましくは7〜9個、および特に好ましくは7個の炭素原子を有する直鎖状もしくは分枝状のモノもしくはポリ不飽和アルケニル基である]
b)少なくとも1個の芳香族基を含有する1種または複数のアルコールとを含有する組成物によって解決されることが発見された。
a)1種または複数の式(I)の化合物と、
Rは、5〜11個、好ましくは7〜9個、および特に好ましくは7個の炭素原子を有する直鎖状もしくは分枝状の飽和アルキル基または5〜11個、好ましくは7〜9個、および特に好ましくは7個の炭素原子を有する直鎖状もしくは分枝状のモノもしくはポリ不飽和アルケニル基である]
b)少なくとも1個の芳香族基を含有する1種または複数のアルコールとを含有する組成物である。
Xは、OまたはCH2であり、
Yは、H、CH3、OH、またはOCH3であり、
Zは、Hまたはハロゲン原子であり、このハロゲン原子は好ましくはF、Cl、およびBrから成る群から選択され、好ましくはClおよびBrから選択され、とりわけ好ましくはClであり、式(II)の化合物は1〜4個のハロゲン原子Zを含有することができ、かつ
Rは、1〜6個の炭素原子を含有し、1個もしくは2個のH原子がヒドロキシル基(OH基)で置き換えられている直鎖状もしくは分枝状の飽和アルキル基であるか、または2〜6個の炭素原子を含有し、1個もしくは2個のH原子がヒドロキシル基(OH基)で置き換えられている直鎖状もしくは分枝状のモノもしくはポリ不飽和の、好ましくはモノ不飽和のアルケニル基である。
それぞれ1種または複数の式(I)の化合物1.0重量部に対し、および好ましくはモノカプリル酸イソソルビド1.0重量部に対し、
I)イソソルビド0.05〜0.7重量部、好ましくは0.1〜0.7重量部、および特に好ましくは0.2〜0.5重量部と、
II)下式のイソソルビドジエステル0.1〜1.0重量部、好ましくは0.2〜1.0重量部、および特に好ましくは0.4〜0.8重量部とを含有している。
Va=試料の滴定の際の水酸化ナトリウム溶液の消費量 単位はml
Vb=作用値の滴定の際の水酸化ナトリウム溶液の消費量 単位はml
c=水酸化ナトリウム溶液の物質量濃度 単位はmol/l
t=水酸化ナトリウム溶液の力価
M=KOHのモル質量=56.11g/mol
E=試料の量り取った量 単位はg
a)水相または水−アルコール性相を最大で95.0重量%、好ましくは49.49〜95.0重量%、特に好ましくは68.9〜90.0重量%、とりわけ好ましくは70.0〜85.0重量%含有しており、
b)油相を最大で70.0重量%、好ましくは4.49〜50.0重量%、特に好ましくは8.9〜30.0重量%、とりわけ好ましくは13.5〜25.0重量%含有しており、
c)1種または複数の式(I)の化合物と、少なくとも1個の芳香族基を含有する1種または複数のアルコールとを含有する組成物を最大で10.0重量%、好ましくは0.01〜10.0重量%、特に好ましくは0.05〜5.0重量%、とりわけ好ましくは0.1〜2.0重量%含有しており、この組成物は上記の化合物およびアルコールを好ましくは30重量%以上、特に好ましくは40重量%以上、とりわけ好ましくは50重量%以上の量で含有しており、さらに式(I)の化合物:少なくとも1個の芳香族基を含有するアルコールの重量比が好ましくは90.0:10.0〜10.0:90.0、特に好ましくは80.0:20.0〜20.0:80.0であり、さらに好ましくはこの組成物は本発明による予混合物であり、かつ
d)1種または複数のさらなる添加物質を最大で20.0重量%、好ましくは0.5〜10重量%、特に好ましくは1.0〜5.0重量%、とりわけ好ましくは1.0〜3.0重量%含有している。
A)カプリル酸イソソルビドの製造
ト字管を備えた撹拌機に、80℃で、イソソルビド(Ecogreen Oleochemicalsの「Sorbon」)190.0g(1.3mol)およびオクタン酸(カプリル酸)187.5g(1.3mol)を、触媒としての水酸化ナトリウム溶液(18重量%水溶液)0.38gと一緒に入れる。撹拌しながら、かつ窒素を通しながら(1時間当たり10〜12リットル)、反応混合物を最初に180℃に加熱し、このとき反応水が分留し始める。その後、出発原料を1時間後に190℃に、それから2時間後に210℃に加熱する。210℃に達した後、酸価が<1mg KOH/gになるまでエステル化させる。琥珀色のカプリル酸イソソルビド345.7g(理論値の97%)が得られる。pH値(エタノール/水1:1中5重量%)は5.9である。pH値はDIN EN 1262に基づいて測定した。
酸価:0.9mg KOH/g、DIN EN ISO 2114に基づいて測定
ヒドロキシル価:206mg KOH/g、DIN 53240−2に依拠して方法OHZ−Aに基づいて測定
鹸化価:204mg KOH/g、DIN EN ISO 3681に基づいて測定
以下では、カプリル酸イソソルビド1 50重量%と、フェノキシエタノール50重量%とから成る本発明による組成物の、細菌、真菌、および酵母に対する抗菌作用を調べる(この組成物を以下に「組成物A」と言う)。細菌で検査するため、組成物Aをブチルポリグリコールで希釈し、続いてpH7(+/−0.2)に緩衝させた50℃の液状Caso寒天(カゼインペプトン寒天)に、様々な濃度で加えた(以下に組成物B1、B2、などと言う)。真菌で、および酵母で検査するため、組成物Aをブチルポリグリコールで希釈し、続いてpH5.6(+/−0.2)に緩衝させた液状のサブロー4%デキストロース寒天に様々な濃度で加えた(以下に組成物PH1、PH2、などと言う)。組成物B1、B2など、またはPH1、PH2などのそれぞれをペトリ皿に注ぎ、それぞれ同量の細菌、真菌、および酵母を接種した。最小発育阻止濃度(MHK)は、組成物B1、B2など、またはPH1、PH2などの中の細菌、真菌、および酵母の発育が阻止される濃度である。
SE=Qa/QA+Qb/QB
式中、
Qaは、用いられる混合物中でのカプリル酸イソソルビド1の最小発育阻止濃度であり、
QAは、カプリル酸イソソルビド1の最小発育阻止濃度であり、
Qbは、用いられる混合物中でのフェノキシエタノールの最小発育阻止濃度であり、
QBは、フェノキシエタノールの最小発育阻止濃度である。
カプリル酸は抗菌作用を有している。しかしカプリル酸は、組成物「カプリル酸イソソルビド1」中に0.4重量%しか存在しないので、この組成物中でのカプリル酸の抗菌作用は無視できるほど小さい。これに加え、カプリル酸はpH値6以上では抗菌作用を有さない。
I)本発明による組成物の例
a)カプリル酸イソソルビド1 50重量%、フェノキシエタノール50重量%
b)カプリル酸イソソルビド1 25重量%、フェノキシエタノール75重量%
c)カプリル酸イソソルビド1 75重量%、フェノキシエタノール25重量%
d)カプリル酸イソソルビド1 40重量%、フェノキシエタノール20重量%、ベンジルアルコール20重量%、安息香酸20重量%
から成る組成物
例a)〜d)の組成物の製造は、80℃に加熱した液状のカプリル酸イソソルビド1を入れたフィンガー型撹拌機で、撹拌速度200〜300回転/分で撹拌しながら個々の成分を次々と混ぜ合わせることによって行われる。
以下の化粧料調合物、植物保護調合物、洗濯洗剤および洗浄剤、または着色剤および塗料1〜41は、例a)〜d)の本発明による組成物を用いて製造される。
Aristoflex(登録商標)AVCを水に溶かす。カルボマーを加える場合は続いてNaOHでpH=7に中和する。残りの成分を必要に応じてPEG−40水添ヒマシ油と混合し、粘度が増した水相に混ぜ入れる。
加熱しながらAを相Bに溶かす。相Cを相Dに分散させ、水相に混ぜ入れる。続いて相EおよびFを混ぜ入れる。
油相Aを80℃に加熱し、ポリマーBを混ぜ入れる。強く撹拌しながら相Cをゆっくり少しずつ加え、それから室温に冷却させる。
Bの成分を次々とAに溶かす。
Aristoflex(登録商標)TACを水に溶かし、その後、次々と相C、D、およびEを入れて均質化する。
相Aを混合し、その後に相Bおよび相Cを次々と加え、それからpH値を相Eで5.5に適合させる。最後に、均質な透明ジェルになるまで相Dを混ぜ入れる。
Bの成分を次々と相Aに混ぜ入れる。
加熱しながら相Aを相Bに溶かし、相Cを混ぜ入れ、相Dを加え、それから相EでpH=6.5に調整する。相Fを混合してから加え、続いて相Gを加え、均質なゲルになるまで撹拌する。必要に応じて相HでpH値を6.5に調整し、それから相Iを混ぜ入れる。
相Aを70℃で溶融し、相Bを撒き入れ、70℃に加熱した相Cを混ぜ入れる。35℃に冷却した後で相Dを混ぜ込み、最後に相EでpH値を6に調整する。
相Aを80℃で溶融し、相Bおよび相Cを次々と混ぜ入れる。相Dを相Eに予め溶かしてから加える。相Fを35℃で混ぜ入れ、それから相GでpH値を6.0に調整する。ゲルクリームができる。
相Aを80℃で溶融し、相Bおよび相Cを次々と混ぜ入れる。相Dを相Eに予め溶かしてから加える。相Fを35℃で混ぜ入れ、それから相GでpH値を6.0に調整する。ゲルクリームができる。
相Aを80℃で溶融し、相Bおよび相Cを次々と混ぜ入れる。相Dを30℃で加え、最後に相Eを混ぜ入れる。結果としてpH値4.2のクリームができる。
製造のため、油溶性成分を80℃に加熱し、セチルリン酸カリウムおよびAristoflex(登録商標)AVCを撒き入れ、一緒にした水溶性相を油相にゆっくりと、強く撹拌しながら投入した。生成されたエマルションを撹拌しながら室温に冷却させた。
相Aを均質化して60℃で溶かして相Bに混ぜ込み、次いで相Cを撹拌しながら加え、1分当たり300回転で撹拌する。続いて相Dを混ぜ入れ、EでpH値を6.8〜7.2に調整する。
相Aを60℃に加熱し、相Bを混ぜ込み、次いで相Cを撹拌しながら加え、1分当たり300回転で撹拌し、それから冷却させる。相Dを35℃で混ぜ入れ、相Eを加え、最後に均質化する。
相Aを70℃に加熱し、相Cを70℃に加熱する。相Bを相Aに混ぜ込み、次いで相Cを加えて良く均質化する。40℃未満に冷却した後、相Dを加えて1分間均質化する。
I AとBを混合する。
II CをIに加え、透明な溶液になるまで撹拌する。
III DをEに溶かし、この溶液をIIに加える。
IV Fの成分を次々とIIIに混ぜ入れる。
V pH値を6.0〜6.5に調整する。
VI 粘度をGで調整する。
I Aを用意し、Bの成分を次々と撹拌しながら加える。
II pH値をCで5.5〜6.0に調整する。
I Aの成分を混合し、それを50℃で溶かす。
II Bの成分を撹拌しながら混合し、少し加熱する。
III Cを約25℃でIIに溶かす。
IV DをIに加える。
V IIIをIVに混ぜ入れる。
VI Eを加える。
VII pH値をFで5.0に調整する。
II Bの成分を混合する。
III IIをIに加える。
IV CでpH値をpH6.0に調整する。
作用物質を他の含有物質(Kelzan(登録商標)Sの溶液を除く)と共に予め分散させ、続いて平均粒子サイズ<2マイクロメートルになるまで微粉砕する。続いてKelzan(登録商標)Sの溶液を混ぜ入れる。
半分の量の水を用意し、表に示した順番で成分を混ぜ入れる。その後、水の残量をさらに加える。結果として透明な水性洗浄剤ができる。
I 成分Aを用意する。
II Bを40〜50℃に加熱して加え、完全に溶解させる。
III 丹念に撹拌しながらCを次々と加える。
IV Dを示した順番で加える。
V 最後にEを加える。
I 成分11、5a、3、および8を用意し、ディゾルバー翼で掻き混ぜる。
II 成分1、6、および7aをヘラで掻き混ぜる。
III ディゾルバー翼を用いてIIをIに添加する。
IV 続いて成分9b、2a、および10を添加する。
Claims (11)
- 成分b)の物質が、フェノキシエタノールである、請求項1に記載の組成物。
- それぞれ、前記組成物の総重量に対し、成分a)の化合物を10.0〜90.0重量%の量で、および1種または複数の成分b)の物質を10.0〜90.0重量%の量で含有している、請求項1または2に記載の組成物。
- 化粧料組成物、皮膚科学的組成物または医薬組成物、植物保護調合物、洗濯洗剤および洗浄剤、または着色剤および塗料である、請求項1または2に記載の組成物。
- それぞれ、前記組成物の総重量に対し、成分a)の化合物を0.01〜10.0重量%の量で、および1種または複数の成分b)の物質を0.01〜10.0重量%の量で含有している、請求項4に記載の組成物。
- 水もしくは水−アルコールをベースとして構成されているか、または溶液、エマルション、もしくは分散系として存在している、請求項4または5に記載の組成物。
- エマルションとして存在している。請求項6記載の組成物。
- pH値が2〜11である、請求項4〜7のいずれか一つに記載の組成物。
- 化粧料組成物、皮膚科学的組成物または医薬組成物、植物保護調合物、洗濯洗剤もしくは洗浄剤、または着色剤もしくは塗料の防腐のための、請求項1〜3のいずれか一つに記載の組成物の使用。
- 化粧料組成物、皮膚科学的組成物または医薬組成物、植物保護調合物、洗濯洗剤もしくは洗浄剤、または着色剤もしくは塗料が、細菌、酵母および真菌に対して防腐される、請求項9に記載の使用。
- 化粧料組成物、皮膚科学的組成物または医薬組成物、植物保護調合物、洗濯洗剤もしくは洗浄剤、または着色剤もしくは塗料が、酵母および真菌に対して防腐される、請求項10に記載の使用。
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CN103717074B (zh) | 2016-07-13 |
JP2014521669A (ja) | 2014-08-28 |
CN103717074A (zh) | 2014-04-09 |
US20140348763A1 (en) | 2014-11-27 |
EP2739152A1 (de) | 2014-06-11 |
ES2607654T3 (es) | 2017-04-03 |
BR112014002600B1 (pt) | 2020-04-22 |
US10406135B2 (en) | 2019-09-10 |
WO2013017264A1 (de) | 2013-02-07 |
BR112014002600A2 (pt) | 2017-04-11 |
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