TWI616517B - 利用包含苯并酚酮(benzotropolone)之植物萃取物及/或相關之酚酮衍生物於家用、身體護理及食物產品之穩定 - Google Patents
利用包含苯并酚酮(benzotropolone)之植物萃取物及/或相關之酚酮衍生物於家用、身體護理及食物產品之穩定 Download PDFInfo
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- TWI616517B TWI616517B TW099134094A TW99134094A TWI616517B TW I616517 B TWI616517 B TW I616517B TW 099134094 A TW099134094 A TW 099134094A TW 99134094 A TW99134094 A TW 99134094A TW I616517 B TWI616517 B TW I616517B
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- Prior art keywords
- alkyl
- hydrogen
- acid
- preparations
- formula
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- 239000000419 plant extract Substances 0.000 title claims description 7
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- 235000013305 food Nutrition 0.000 title description 2
- -1 phenol ketone Chemical class 0.000 claims abstract description 136
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
- 239000001257 hydrogen Substances 0.000 claims abstract description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 125000005605 benzo group Chemical group 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
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- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 3
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Abstract
本發明揭示下式之苯并酚酮衍生物之用途(1),其中R1、R2及R7彼此獨立地為氫;C1-C30烷基;或COR8;R3係氫;或COOR9R4係氫;或C1-C30烷基;R5係氫;羥基;C1-C30-烷氧基;或-O-(CO)-R10;R6係氫;C1-C30烷基;或COR8;或R5與R6可一起形成五或六員環;或R6與R7一起形成五或六員環;且R8、R9、R10彼此獨立地為C1-C30烷基;其用於保護身體護理及家用產品,免於光解及氧化降解。
Description
本發明係關於所選光穩定劑用於保護身體護理及家用產品免於光解及氧化降解之用途。
在化妝品調配物及家用產品中,近年來產品趨向於更多的使用基於油及脂肪之天然物質,此亦加劇脂肪及油氧化降解問題,從而導致腐敗。乳液幾乎從不缺乏天然油或不飽和脂肪酸。氧化改變往往可產生反應性代謝物,例如酮、醛、酸、環氧化物及脂質過氧化物。
因此,一方面產物氣味發生不期望之改變且另一方面物質易於變質,進而可改變皮膚耐受性。自由基在皮膚上之不受控形成係多種病理生理調節(例如過敏、炎症、癌發生及諸如此類)發生及發展的主要原因。
然而,氧化降解過程不僅出現在基於油及脂肪之天然物質之情形下。其亦出現在許多其他化妝品成份中,例如芳香劑及芳香物質、維生素、著色劑及諸如此類。
為防止氧化降解過程(光氧化、自氧化),因此在化妝品及食物產品中使用所謂的抗氧化劑(AO)。此等抗氧化劑可劃分為防止氧化之化合物(配位劑、還原劑及諸如此類)及阻斷自由基鏈反應之化合物(例如丁基化羥基甲苯(BHT)、丁基化羥基苯甲醚(BHA)、沒食子酸酯(例如沒食子酸丙基酯(PG))、或第三丁基氫醌(TBHQ))。然而,後者之化合物通常無法滿足有關pH穩定性以及光及溫度穩定性之要求。
因此,該等內含物中之活性物質因自氧化過程而不利地改變其性質。從而導致(例如)黏度降低及顏色或氣味改變。
此外,對於化妝品調配物及家用產品,近年來產品發展趨勢亦已使得透明(玻璃、PET等)容器之使用增多。儘管玻璃及普通塑膠二者在UV-B-範圍內具有一定固有吸收,但在UV-A範圍內吸收極低。
因UV吸收,通常對透明封裝產品使用各種穩定技術且該等技術已眾所周知。舉例而言,與其他吸收劑(例如二苯甲酮,其主要吸收UV-B)相比,苯并三唑類寬帶UV光穩定劑因其極佳之UV-A及UV-B吸收性質可增強產品穩定性且存放期限。迄今所知防止或延遲光引起之透明封裝產品褪色之最有效穩定劑係(例如)以商品名BASF TINOGARD HS或BASF TINOGARD TL登記之苯并三唑衍生物。
現今,在一個穩定劑分子中組合抗氧化及自由基清除以及光保護性質將甚為有利。
令人驚奇的是,已發現基於苯并酚酮衍生物之特定光穩定劑表現出突出的UV吸收劑以及抗氧化劑性質且因此適用於產品保護。
基於苯并酚酮部分之多酚可自植物或真菌分離得到。天然存在苯并酚酮之實例係紅棓酚、紅棓酚羧酸、來自真菌木蹄層孔菌(Fomes fomentarius)之氟米妥芬(fomentariol)、古匹林酮(goupiolone)及來自真菌橘黃色口蘑菌(Tricholoma aurantium)之奧羅氯酮(aurantricholone)。存於紅茶中之茶黃素係含有苯并酚酮核之多酚之另一習知群。
合成苯并酚酮係藉由1,2-二羥基苯衍生物與1,2,3-三羥基苯衍生物之氧化偶合來製備。
合成及天然存在苯并酚酮化合物共同之處在於其係具有強抗氧化劑性質之有效且光穩定之UV吸收劑且因此適宜用作穩定劑。
因此,本發明係關於下式之苯并酚酮衍生物之用途(1),其中R1、R2及R7彼此獨立地為氫;C1-C30烷基;或COR8;R3係氫;或COOR9;R4係氫;或C1-C30烷基;R5係氫;羥基;C1-C30-烷氧基;或-O-(CO)-R10;R6係氫;C1-C30烷基;或COR8;或R5與R6可一起形成五或六員環;或R6與R7一起形成五或六員環;且R8、R9、R10彼此獨立地為C1-C30烷基;其用於保護身體護理及家用產品免於光解及氧化降解。
較佳者係式(1)化合物,其中R1係氫;COR8;或C1-C30烷基;R2、R4及R5係氫;R3係COOR9;R6及R7彼此獨立地為氫;C1-C30烷基;或COR8;或R6與R7一起形成五或六員環;且R8係如式(1)中所定義。
更佳者係式(1)化合物,其中R1係氫;或CO-CH3;R2、R4及R5係氫;R3係COO-C3H7;R6及R7彼此獨立地為氫;或CO-CH3;或R6與R7一起形成五或六員環。
亦較佳者係式(1)化合物,其中R1、R2及R7彼此獨立地為氫;甲基;或-CO-CH3;R3係氫;或-COOR9;R4係氫;或C1-C30烷基;R5係氫;甲氧基;或-O-(CO)-CH3;R6係氫;甲基;或-CO-CH3;或R5與R6可一起形成五或六員環;或R6與R7一起形成五或六員環;且R9 係C1-C10烷基。
最佳者係下列各式化合物:
用於本發明之苯并酚酮之其他實例係化合物
C1-C30烷基係直鏈或具支鏈基團,例如甲基、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基、戊基、異戊基或第三戊基、己基、2-乙基己基、庚基、辛基、異辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十一烷基、二十烷基、二十四烷基、二十五烷基、二十七烷基、二十八烷基或三十烷基。
C1-C30烷氧基係直鏈或具支鏈基團,例如甲氧基、乙氧基、正丙氧基、或異丙氧基、異丙基氧基、正丁基氧基、第二丁基氧基、第三丁基氧基、戊基氧基、異戊基氧基或第三戊基氧基、己基氧基、2-乙基己基氧基、庚基氧基、辛基氧基、異辛基氧基、壬基氧基、癸基氧基、十一烷基氧基、十二烷基氧基、十四烷基氧基、十一烷基氧基、二十烷基氧基、二十四烷基氧基、二十五烷基氧基、二十七烷基氧基、二十八烷基氧基或三十烷基氧基。
每一烷基可為飽和或不飽和。
每一烷基可經一或多個E取代及/或間雜有一或多個D。
D 係-CO-;-COO-;-O-;-S-;-CR12=CR13-;或-C≡C-;且E 係-OR18;-NR14R15;-COR17;-COOR16或-CONR14R15;其中R12、R13、R14及R15彼此獨立地為氫;視情況經OH、C1-C18烷基或C1-C18烷氧基取代之C6-C18芳基;視情況間雜有-O-之C1-C18烷基;或R14與R15一起形成五或六員環,R16係氫;視情況經OH、C1-C18烷基或C1-C18烷氧基取代之C6-C18芳基;視情況間雜有-O-之C1-C18烷基;R17係H;視情況經OH、C1-C18烷基或C1-C18烷氧基取代之C6-C18芳基;或視情況間雜有-O-之C1-C18烷基;R18係氫;視情況經OH、C1-C18烷基或C1-C18烷氧基取代之C6-C18芳基;或視情況間雜有-O-之C1-C18烷基。
式(1)化合物可以其質子化或去質子化形式存在。
本發明中所用苯并酚酮衍生物代表已知及新穎化合物。
該等新穎化合物對應於下式(1'),其中R'1、R'2及R'7彼此獨立地為氫;C1-C30烷基;或COR8;R'3係氫;或COOR9;R'4係氫;或C1-C30烷基;R'5係氫;羥基;C1-C30-烷氧基;或-O-(CO)-R10;R'6係氫;C1-C30烷基;或COR8;或R'5與R'6可一起形成五或六員環;或R'6與R'7一起形成五或六員環;且R'8、R'9、R'10彼此獨立地為C1-C30烷基;條件係在式(1')化合物中R7與R8一起形成五或六員環;或R6與R7一起形成五或六員環。
較佳者係式(1')化合物,其中R3 係式之基團,其中R'20係C3-C30烷基R'5係氫;或C1-C12烷基;R'1、R'6及R'7係氫;COR'9;或C1-C30烷基;且R'9係如在式(1')中所定義。
較佳者亦係對應於下式化合物(2'),其中R'21及R'22彼此獨立地為氫;OH;C1-C30烷基;或C1-C30烷氧基;且R'1、R'2、R'3、R'4及R'7係如在式(1')中所定義。
較佳者亦為下式化合物(3'),其中R'21及R'22彼此獨立地為氫;OH;C1-C30烷基;或C1-C30烷氧基;R'1、R'2、R'3、R'4及R'5係如在式(1')中所定義。
更佳者係式(3')化合物,其中R'21及R'22彼此獨立地為氫;OH;未經取代C1-C30烷基或未經取代C1-C30烷氧基;且R'1、R'2、R'3、R'4及R'5係如在式(1')中所定義。
其他新穎化合物對應於式(3'),其中R3 係式之基團,其中R'20係C3-C30烷基;R'5係氫;或C1-C12烷基;R'1、R'6及R'7係氫、COR'9;或C1-C30烷基;且R'9係如式(1')中所定義。
其他新穎化合物對應於下式(4'),其中R'2及R'4彼此獨立地為C1-C30烷基;R'1、R'5、R'6及R'7係C1-C30烷基;或COR8;且R'8係如在式(1')中所定義。
較佳者亦為下式化合物(5'),其中R'3係式之基團;R'20 係C3-C30烷基;R'1、R'6及R'7係氫;COR9;或C1-C30烷基;且R'9係C1-C30烷基。
本發明苯并酚酮衍生物係自天然來源(例如自植物萃取物)分離得到及/或由特定前體化合物(例如苯三酚衍生物及1,2-二羥基-苯衍生物)之化學氧化來合成。
式(1)之苯并酚酮衍生物以及此等化合物與如表1-3中所列示之其他UV吸收劑、酚系或非酚系抗氧化劑或與配位劑的混合物尤其適用於保護身體護理及家用產品免於光解降解。
可與式(1)化合物混合使用之有機UV過濾劑之實例列示於下表中:
式(1)之苯并酚酮衍生物亦可與如(例如)WO 00/25731中所揭示之酚系或內酯型抗氧化劑混合使用。
式(1)之苯并酚酮衍生物亦可與如WO 03/103622中所揭示之受阻胺光穩定劑(例如受阻硝醯基、羥基胺及羥基胺鹽化合物)混合使用。
為優化抗氧化效果,家用及/或個人護理應用可含有在製劑總重量0.0001%至10%濃度範圍內之至少一種其他親水或親脂抗氧化劑。彼等額外抗氧化劑較佳選自含有下列之群:
- 生育酚(α、β、γ、δ異構體,具體而言維生素E)及其衍生物(具體而言維生素E衍生物,例如維生素E乙酸酯、維生素E亞油酸酯、維生素E菸鹼酸酯及維生素E琥珀酸酯)。
- 含有一個不飽和脂肪鏈之生育三烯酚(α、β、γ、δ異構體)、及其與酸之酯。
- 抗壞血酸及其與酸(例如磷酸)之酯以及鈉鹽、鉀鹽、鋰鹽及鎂鹽、四異棕櫚酸抗壞血酸酯、其他與吡咯啶酮羧酸之酯及與通式(3) H(CH2)n(CHR)COOH及(4) CH3(CH2)mCH=CH(CH2)nCOOH之酸之酯,其中R係氫原子或OH基團,m、n係0至20之整數,其中m+n總和最大為21。
- 類視色素,其包括所有維生素A之天然及/或合成類似物或在皮膚中具有維生素A生物活性之類視黃醛化合物以及此等化合物之幾何異構體及立體異構體。較佳化合物係視黃醇、視黃醇酯(例如,視黃醇之C2-C22烷基酯(飽和或不飽和烷基鏈),包括棕櫚酸視黃酯、乙酸視黃酯、丙酸視黃酯)、視黃醛、及/或視黃酸(包括所有反式視黃酸及/或13-順式-視黃酸)或衍生物。可用於本文之其他類視色素闡述於下列美國專利中:於1987年6月30日頒佈之頒予Parish等人的第4,677,120號;於1989年12月5日頒佈之頒予Parish等人的第4,885,311號;於1991年9月17日頒佈之頒予Purcell等人的第5,049,584號;於1992年6月23日頒佈之頒予Purcell等人的第5,124,356號。其他適宜之類視色素係視黃酸生育酚酯[視黃酸(反式或順式)之生育酚酯]、阿達帕林(adapalene)[6-(3-(1-金剛烷基)-4-甲氧基苯基)-2-萘酸]及他紮羅汀(tazarotene)(6-[2-(4,4-二甲基硫-6-基)-乙炔基]菸鹼酸乙基酯)。
- 類胡蘿蔔素,例如α-、β-、γ-及δ-胡蘿蔔素、黃體素、黃葉素、玉米黃素、堇黃素、隱黃素、藻褐素、環氧玉米黃質、番茄紅素、二脫氫番茄紅素及四脫氫番茄紅素類胡蘿蔔素。
- 硫辛酸及其衍生物,例如α-硫辛酸。
- 芸香亭酸及其衍生物,例如α-葡糖基芸香苷(一種水溶性類黃酮)、水合芸香苷(維生素P)。
- 藥材萃取物,例如白茶及綠茶萃取物、紅茶萃取物、菊苣葉萃取物(菊苣(Cichorium intybus))、西番蓮萃取物(美國西番蓮(Passiflora incarnata))、線狀阿司巴拉妥(Aspalathus linearis)萃取物、謎迭香萃取物、槭樹科(Aceraceae)楓樹或薔薇科(Rosaceae)櫻桃樹之紅葉萃取物、薑黃(Curcuma longa L)(類薑黃色素活性成份)、高山火絨草(Leontopodium alpinum)萃取物、印第安鵝莓(Emblica officinalis)(餘甘子(phyllanthus emblica))樹萃取物。
- 酚酸,例如咖啡酸、3,4-二羥基苯基乙酸、3,4-二羥基-苯甲酸。
- 沒食子酸酯,例如沒食子酸、沒食子酸甲基酯、沒食子酸乙基酯、沒食子酸丙基酯、沒食子酸辛基酯、沒食子酸十二烷基酯、沒食子酸戊基酯、沒食子酸異戊基酯、醯化沒食子酸酯,如3,4,5-叁(乙醯基氧基)-苯甲酸甲基酯、3,4,5-叁(乙醯基氧基)-苯甲酸丙基酯、3,4,5-叁(乙醯基氧基)-苯甲酸辛基酯。
- 兒茶酚,例如1,2-二羥基苯、3-甲基兒茶酚、4-第三丁基兒茶酚或例如醯化兒茶酚,例如兒茶酚二乙酸酯、3-甲基兒茶酚二乙酸酯、兒茶酚乙酸酯。
- 苯三酚,例如1,2,3-三羥基苯、4-乙基苯三酚、4-丙基苯三酚、4-丁基苯三酚、4-戊基苯三酚、4-異戊基苯三酚、4-辛基苯三酚、4-十二烷基苯三酚或例如醯化苯三酚,例如苯三酚乙酸酯、苯三酚二乙酸酯、苯三酚三乙酸酯。
- 類黃酮及多酚,例如黃烷酮,其選自由未經取代之黃烷酮、單取代黃烷酮、及其混合物組成之群;查耳酮(chalcone),其選自由未經取代之查耳酮、單取代查耳酮、二取代查耳酮、三取代查耳酮、及其混合物組成之群;黃酮,其選自由未經取代之黃酮、單取代黃酮、二取代黃酮、及其混合物組成之群;一或多種異黃酮;香豆素,其選自由未經取代之香豆素、單取代香豆素、二取代香豆素、及其混合物組成之群;黃酮醇、花色素苷、兒茶素(例如綠茶兒茶素,例如(-)-表沒食子兒茶素-3-沒食子酸酯、(-)-表兒茶素、(-)-表沒食子兒茶素及其混合物)、茶黃素、原花色素(葡萄籽萃取物)。亦可使用廣泛揭示於美國專利5,686,082及5,686,367中之類黃酮。
- 綠原酸及阿魏酸及其衍生物。
- 酚酮衍生物,例如酚酮(CAS第533-75-5號)本身、扁柏油酚、黃柏素、密擠青黴酸、短毛酸、密擠青黴酸、短毛黴酮酸、γ-側柏素、β-側柏素、秋水仙醯胺或如專利申請案WO 2008/003529 A1中所闡述之酚酮衍生物及其混合物。
亦可使用當UV輻射透過皮膚或頭髮時可阻斷光化學反應鏈引發之第三種抗氧化劑。該等抗氧化劑之典型實例係胺基酸及其衍生物(例如甘胺酸、組胺酸、乙醯基組胺酸、酪胺酸、己醯基酪胺酸、色胺酸)、咪唑(例如尿刊酸)及其衍生物、肽(例如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(例如鵝肌肽))、金硫葡糖、丙硫氧嘧啶及其他硫醇(例如硫氧還蛋白、麩胱甘肽、半胱胺酸、胱胺酸、胱胺及其糖基、N-乙醯基、甲基、乙基、丙基、戊基、丁基、月桂基、棕櫚醯基、油基、亞麻油基、膽甾醇基及甘油基酯)以及其鹽、硫代二丙酸二月桂基酯、硫代二丙酸二硬脂基酯、硫代二丙酸及其衍生物(酯、醚、肽、脂、核苷酸、核苷及鹽)以及亞碸亞胺化合物(例如丁硫胺酸亞碸亞胺、高半胱胺酸亞碸亞胺、丁硫胺酸碸、五-、六-、七-硫堇亞碸亞胺)。
以及(金屬)螯合劑(具體而言α-羥基脂肪酸、棕櫚酸、植酸、乳鐵蛋白)且較佳為彼等下列中所揭示者:於1996年1月30日頒佈之頒予Bisset等人的美國專利第5,487,884號;於1995年12月31日公佈之Bush等人之國際申請案第91/16035號及第91/16034號。羥基酸(例如檸檬酸、乳酸、蘋果酸、羥基琥珀酸)、胡敏酸、膽汁酸、膽汁萃取物、膽紅素、膽綠素、EDTA、EDDS、EGTA及其衍生物、不飽和脂肪酸及其衍生物(例如亞麻酸、亞油酸、油酸)、葉酸及其衍生物、安息香樹脂之苯甲酸松柏酯、阿魏酸、呋喃亞甲基葡糖醇、肌肽、丁基羥基甲苯、丁基羥基苯甲醚、去甲二氫愈創木酸、三羥基丁酸酚酮、尿酸及其衍生物、甘露糖及其衍生物、N-[3-(3,5-二-第三丁基-4-羥基苯基)丙醯基]磺胺酸(及其鹽,例如二鈉鹽)、鋅及其衍生物(例如ZnO、ZnSO4)、硒及其衍生物(例如硒代甲硫胺酸)、均二苯乙烯及其衍生物(具體而言羥基均二苯乙烯、白藜蘆醇及赤松素)及具有彼等所提及活性成份之適於本發明之衍生物(鹽、酯、醚、糖、核苷酸、核苷、肽及脂)。亦可提及HALS(=「受阻胺光穩定劑」)化合物。
其他合成及天然抗氧化劑列示於(例如)專利WO 0025731中:結構1-3(第2頁)、結構4(第6頁)、結構5-6(第7頁)及化合物7-33(第8頁至第14頁)。
適宜抗氧化劑之實例包括(但不限於)對-羥基苯甲酸及其衍生物(對-羥基苯甲酸乙基異丁基酯、對-羥基苯甲酸甘油酯)、水楊酸酯(辛基戊基酯、苯基酯、苄基薄荷基酯、甘油酯及二丙二醇酯)、丙二酸亞苄基酯、苯基甲基丙酸衍生物(例如[(4-羥基-3,5-二甲氧基苯基)甲基]-丙二酸雙(2-乙基己基)酯(CAS第872182-46-2號))、經羥基或甲氧基取代之二苯甲酮、尿酸或單寧酸及其衍生物。
可用於本發明化妝品組合物之其他額外抗氧化劑選自由下列組成之群:乙醯基半胱胺酸、3-第三丁基-4-羥基苯甲醚、2,6-二-第三丁基-對甲酚、咖啡酸、綠原酸、癸基巰基甲基咪唑、硫代二丙酸二乙醯基酯、三油酸二沒食子醯基酯、硫代二丙酸二月桂基酯、硫代二丙酸二肉豆蔻基酯、二油基生育酚甲基矽烷醇、芸香亭基硫酸二鈉、硫代二丙酸二硬脂基酯、硫代二丙酸二(十三烷基)酯、沒食子酸十二烷基酯、異抗壞血酸、阿魏酸乙酯、氫醌及烷基化氫醌(例如第三丁基氫醌、二戊基氫醌、二-第三丁基氫醌)、對-羥基苯甲醚、鹽酸羥胺、硫酸羥胺、硫代乙醇酸異辛基酯、曲酸、羥基積雪草甙(madecassicoside)、甲氧基-PEG-7-琥珀酸芸香亭基酯、沒食子酸辛基酯、苯基硫代乙醇酸、間苯三酚、沒食子酸丙基酯、迷迭香酸及其衍生物、芸香苷、異抗壞血酸鈉、硫代乙醇酸鈉、山梨醇縮糠醛、硫代二乙二醇、硫代二乙二醇醯胺、硫代二乙醇酸、硫代乙醇酸、硫代乳酸、硫代水楊酸、生育酚聚醚-5、生育酚聚醚-10、生育酚聚醚-12、生育酚聚醚-18、生育酚聚醚-50、托可索侖(tocophersolan)、鄰-甲苯基雙胍、亞磷酸叁(壬基苯基)酯、右泛醇、α-羥基羧酸(具體而言乙醇酸、乳酸、扁桃酸)及其鹽、二羥甲基二甲基乙內醯脲、N-醯基胺基酸及其鹽(具體而言N-辛醯基甘胺酸)及扁柏酚、及其混合物,其用於長期穩定下列通式之甘油單烷基醚:R-O-CH2-CHOH-CH2-OH,其中R係具支鏈或不具支鏈C3-C18烷基,其中該烷基可經一或多個羥基及/或C1-C4烷氧基取代及/或烷基鏈可間雜有至多四個氧原子。
可用於本發明化妝品組合物之其他額外抗氧化劑選自由下列組成之群:丙胺酸二乙酸、槲皮素、桑黃素、3,4-二羥基苯甲酸、麝香草酚、香芹酚、兒茶素、以及安息香膠樹脂之衍生物、芸香苷及其衍生物、及苄基膦酸酯(例如,2,5-二-第三丁基-4-羥基苄基膦酸二甲基酯、3,5-二-第三丁基-4-羥基苄基膦酸二乙基酯及3,5-二-第三丁基-4-羥基苄基膦酸單乙基酯之鈣鹽)。
較佳地,本發明苯并酚酮衍生物係用於含有選自沒食子酸酯衍生物、兒茶酚衍生物或苯三酚衍生物之至少一種其他抗氧化劑的混合物中。
除式(1)之苯并酚酮衍生物外,本發明家用及/或個人護理組合物亦可含有如(例如)於WO 00/25731中所揭示之酚系或內酯型抗氧化劑及/或如於WO 03/103622中所揭示之受阻胺光穩定劑(例如受阻硝醯基、羥基胺及羥基胺鹽化合物)。
式(1)之苯并酚酮衍生物可以單一組份形式使用或可與其他穩定劑混合使用,具體而言用於皮膚護理產品、沐浴及淋浴添加劑、含有芳香劑及芳香物質之製劑、頭髮護理產品、潔齒劑、除臭及止汗製劑、彩妝用製劑、防曬調配物及含有活性成份之製劑。
皮膚護理產品具體而言係身體油、身體洗劑、身體凝膠、保養乳霜、護膚膏、刮鬍製劑(例如刮鬍泡沫劑或凝膠)、膚用粉劑(例如嬰兒爽身粉)、保濕凝膠、保濕噴霧、緊致活膚身體噴霧、纖體凝膠及去角質製劑。
適宜之沐浴及淋浴添加劑係淋浴凝膠、浴鹽、沐浴露及皂。
含有芳香劑及芳香物質之製劑具體而言係香水、香料、花露水及刮鬍水(刮鬍後製劑)。
適宜之頭髮護理產品為(例如)人類及動物(具體而言犬)洗髮精、護髮素、用於造型及保養頭髮之產品、燙髮劑、定型噴霧及髮蠟、髮膠、固髮劑及染髮劑或漂白劑。
適宜之潔齒劑具體而言係牙霜(tooth cream)、牙膏、漱口劑、口腔清洗劑、抗牙斑製劑及假牙清潔劑。
適宜之彩妝性製劑(decorative preparation)具體而言係唇膏、指甲油、眼影、睫毛膏、乾及濕粉餅、腮紅、粉劑、脫毛劑及曬黑洗劑。
含有活性成份之適宜化妝品調配物具體而言係激素製劑、維生素製劑、植物萃取物製劑及抗菌製劑。
所提及之身體護理產品可呈下列形式:乳霜、軟膏、膏糊、發泡體、凝膠、洗劑、粉劑、粉餅、噴霧、貼片或氣溶膠。
其較佳含有式(1)之苯并酚酮衍生物,及視情況其他UV吸收劑、空間受阻胺、錯合劑及酚系或非酚系抗氧化劑。
因此,本發明亦係關於包含至少一種式(1)之苯并酚酮衍生物之身體護理產品。
式(1)之苯并酚酮衍生物以總調配物計係以約5 ppm至約10000 ppm、較佳約10 ppm至約5000 ppm、且最佳約100 ppm至約1000 ppm之濃度存於身體護理及家用產品中。
本發明化妝品組合物亦可含有一或多種如下文所述之額外化合物。
基於具有6個至18個、較佳8個至10個碳原子之脂肪醇之格爾伯特(Guerbet)醇,該等脂肪醇包括鯨蠟醇、硬脂醇、鯨蠟硬脂醇、油醇、辛基十二烷醇、C12-C15醇之苯甲酸酯、乙醯化羊毛脂醇等。
直鏈C6-C24脂肪酸與直鏈C3-C24醇之酯、具支鏈C6-C13羧酸與直鏈C6-C24脂肪醇之酯、直鏈C6-C24脂肪酸與具支鏈醇(尤其2-乙基己醇)之酯、羥基羧酸與直鏈或具支鏈C6-C22脂肪醇之酯(尤其蘋果酸二辛基酯)、直鏈及/或具支鏈脂肪酸與多羥基醇(例如丙二醇、二聚體二醇或三聚體二醇)及/或格爾伯特醇之酯,例如己酸、辛酸、2-乙基己酸、癸酸、月桂酸、異十三烷酸、肉豆蔻酸、棕櫚酸、棕櫚油酸、硬脂酸、異硬脂酸、油酸、反油酸、岩芹酸、亞油酸、亞麻酸、桐酸、花生酸、鱈烯酸、山萮酸及瓢兒菜酸及其工業級混合物(舉例而言,在天然脂肪及油加壓去除期間、在來自瑞倫氏(Roelen's)側氧基合成之醛還原期間或在不飽和脂肪酸二聚期間獲得)與(例如)下列醇之酯:異丙醇、己醇、辛乙二醇、2-乙基己基醇、癸醇、月桂基醇、異十三烷基醇、肉豆蔻基醇、鯨蠟醇、棕櫚油醇、硬脂醇、異硬脂醇、油醇、反油醇、岩芹醇、亞油醇、亞麻醇、桐醇、花生醇、鱈烯醇、山萮醇、瓢兒菜醇及巴惟醇及其工業級混合物(舉例而言,在基於脂肪及油之工業級甲基酯或來自瑞倫氏側氧基合成之醛高壓氫化期間及在不飽和脂肪醇二聚期間作為單體部分獲得)。
該等酯油之實例係肉豆蔻酸異丙基酯、棕櫚酸異丙基酯、硬脂酸異丙基酯、異硬脂酸異丙基酯、油酸異丙基酯、硬脂酸正丁基酯、月桂酸正己基酯、油酸正癸基酯、硬脂酸異辛基酯、硬脂酸異壬基酯、異壬酸異壬基酯、棕櫚酸2-乙基己基酯、月桂酸2-己基酯、硬脂酸2-己基癸基酯、棕櫚酸2-辛基十二烷基酯、油酸油基酯、瓢兒菜酸油基酯、油酸瓢兒菜基酯、瓢兒菜酸瓢兒菜基酯、辛酸鯨蠟基酯、棕櫚酸鯨蠟基酯、硬脂酸鯨蠟基酯、油酸鯨蠟基酯、山萮酸鯨蠟基酯、乙酸鯨蠟基酯、肉豆蔻酸肉豆蔻基酯、山萮酸肉豆蔻基酯、油酸肉豆蔻基酯、硬脂酸肉豆蔻基酯、棕櫚酸肉豆蔻基酯、乳酸肉豆蔻基酯、丙二醇二辛酸酯/癸酸酯、庚酸硬脂基酯、蘋果酸二異硬脂基酯、羥基硬脂酸辛基酯等。
基於C6-C18脂肪酸且藉由與其他醇反應而改質之二-或三-甘油酯(辛酸/癸酸甘油三酯、小麥胚芽甘油酯等)。聚甘油之脂肪酸酯(聚甘油基-n(例如聚甘油基-4癸酸酯、聚甘油基-2異硬脂酸酯等)或蓖麻油、氫化植物油、甜扁桃仁油、小麥胚芽油、芝麻油、氫化棉籽油、椰子油、鱷梨油、玉米油、氫化蓖麻油、牛油樹脂、可可脂、大豆油、貂油、葵花油、紅花油、夏威夷果油、橄欖油、氫化獸脂、杏仁油、榛果油、琉璃苣籽油等。
包括長鏈酸與醇之酯,及具有蠟樣性質之化合物,例如,巴西棕櫚蠟、蜂蠟(白色或黃色)、羊毛脂蠟、小燭蠟、地蠟、日本蠟、石蠟、微晶蠟、純地蠟、鯨蠟基酯蠟、合成蜂蠟等。以及親水蠟,例如鯨蠟硬脂醇或偏甘油酯。
烷二醇酯,尤其乙二醇二硬脂酸酯;脂肪酸鏈烷醇醯胺,尤其椰油脂肪酸二乙醇醯胺;偏甘油酯,尤其硬脂酸單甘油酯;未經取代或經羥基取代之多價羧酸與具有6個至22個碳原子之脂肪醇的酯,尤其酒石酸之長鏈酯;總計具有24個碳原子之脂肪物質,例如脂肪醇、脂肪酮、脂肪醛、脂肪醚及脂肪族碳酸酯,尤其月桂酮及二硬脂基醚;脂肪酸,例如硬脂酸、羥基硬脂酸或山萮酸;具有12個至22個碳原子之烯烴環氧化物與具有12個至22個碳原子之脂肪醇及/或具有2個至15個碳原子及2個至10個羥基之多元醇的開環產物,及其混合物。
礦物油(輕質或重質)、凡士林(黃色或白色)、微晶蠟、石蠟及異石蠟化合物、氫化異石蠟分子,例如聚癸烯及聚丁烯、氫化聚異丁烯、角鯊烷、異十六烷、異十二烷及其他來自植物界及動物界者。
聚二甲基矽氧烷、甲基苯基聚矽氧烷、環狀聚矽氧、以及經胺基-、脂肪酸-、醇-、聚醚-、環氧-、氟-、糖苷-及/或烷基修飾之聚矽氧化合物(其在室溫下可呈液體或樹脂形式)。直鏈聚矽氧烷、聚二甲基矽氧烷(Dow Corning 200流體,Rhodia Mirasil DM)、聚二甲基矽氧烷醇、環狀聚矽氧流體、環戊矽氧烷揮發物(Dow Corning 345流體)、苯基三甲基矽氧烷(Dow Corning 556流體)。亦適宜者係水合矽石聚二甲矽氧烷,其係平均鏈長為200個至300個二甲基矽氧烷單元之聚二甲基矽氧烷與氫化矽酸鹽之混合物。適宜揮發性聚矽氧之詳細概述可另外見於Todd等人之Cosm.Toil. 91,27(1976)。
全氟己烷、二甲基環己烷、乙基環戊烷、聚全氟甲基異丙基醚。
組合物可使用任一習用乳化劑。乳化劑系統可包含(例如):碳環酸及其鹽:含鈉、鉀及銨之鹼性皂、含鈣或鎂之金屬皂、有機基質皂,例如月桂酸、棕櫚酸、硬脂酸及油酸等等。烷基磷酸鹽或磷酸酯、酸式磷酸鹽、二乙醇胺磷酸鹽、鯨蠟基磷酸鉀。乙氧基化羧酸或聚乙二醇酯(PEG-n丙烯酸酯)。具有8個至22個碳原子之直鏈脂肪醇,其具有2 mol至30 mol環氧乙烷及/或0至5 mol環氧丙烷之支鏈,與具有12個至22個碳原子之脂肪酸且在烷基中具有8個至15碳原子之烷基酚。脂肪醇聚乙二醇醚,例如月桂醇聚醚-n、鯨蠟硬脂醇聚醚-n、硬脂醇聚醚-n、油醇聚醚-n。脂肪酸聚乙二醇醚,例如PEG-n硬脂酸酯、PEG-n油酸酯、PEG-n椰油酸酯。單甘油酯及多元醇酯。1 mol至30 mol環氧乙烷與多元醇之加成產物之C12-C22脂肪酸單-及二-酯。脂肪酸及聚甘油酯,例如單硬脂酸甘油酯、聚甘油基-3-二異硬脂酸二異硬脂醯基酯、聚甘油基-3-二異硬脂酸酯、二異硬脂酸三甘油基酯、聚甘油基-2-倍半異硬脂酸酯或二元脂肪酸聚甘油基酯。來自複數種彼等物質類別之化合物之混合物亦係適宜的。脂肪酸聚乙二醇酯(例如二乙二醇單硬脂酸酯)、脂肪酸與聚乙二醇之酯、脂肪酸與蔗糖之酯(例如蔗糖酯)、甘油與蔗糖之酯(例如蔗糖甘油酯)。山梨醇及山梨醇酐、具有6個至22個碳原子之飽和及不飽和脂肪酸之山梨醇酐單-及二-酯及環氧乙烷加成產物。聚山梨醇酯-n系列,山梨醇酐酯(例如倍半異硬脂酸酯)、山梨醇酐、PEG-(6)-山梨醇酐異硬脂酸酯、PEG-(10)-山梨醇酐月桂酸酯、PEG-17-山梨醇酐二油酸酯、葡萄糖衍生物、C8-C22烷基-單及寡-糖苷及乙氧基化類似物,其中葡萄糖作為糖組份較佳。O/W乳化劑,例如甲基葡糖醇聚醚-20倍半硬脂酸酯、山梨醇酐硬脂酸酯/蔗糖椰油酸酯、甲基葡萄糖倍半硬脂酸酯、鯨蠟硬脂醇/鯨蠟基葡糖苷。W/O乳化劑,例如甲基葡萄糖二油酸酯/甲基葡萄糖異硬脂酸酯。硫酸鹽及磺化衍生物,二烷基磺基琥珀酸鹽、二辛基琥珀酸鹽、烷基月桂基磺酸鹽、直鏈磺化石蠟、磺化四伸丙基磺酸鹽、月桂基硫酸鈉、月桂基硫酸銨及月桂基硫酸乙醇胺鹽、月桂基醚硫酸鹽、月桂醇醚硫酸鈉、磺基琥珀酸鹽、乙醯基異硫羰酸鹽、烷醇醯胺硫酸鹽、牛磺酸、甲基牛磺酸、咪唑硫酸鹽。胺衍生物,胺鹽、乙氧基化胺、具有含雜環(例如烷基咪唑啉)鏈之氧化胺,吡啶衍生物,異喹啉、氯化鯨蠟基吡啶鎓、溴化鯨蠟基吡啶鎓、四級銨(例如鯨蠟基三甲基溴化銨(CTBA))、硬脂基烷基鎓。醯胺衍生物,鏈烷醇醯胺(例如醯基醯胺DEA)、乙氧基化醯胺(例如PEG-n醯基醯胺)、草醯胺。聚矽氧烷/聚烷基/聚醚共聚物及衍生物,聚二甲基矽氧烷、共聚醇、聚矽氧聚環氧乙烷共聚物、聚矽氧乙二醇共聚物。丙氧基化或POE-n醚(美羅沙波(Meroxapol))、泊洛沙姆(Polaxamer)或聚(氧乙烯)m-嵌段-聚(氧丙烯)n-嵌段(氧乙烯)。在分子中攜帶至少一個四級銨基團至少一個羧酸根及/或磺酸根基團之兩性離子表面活性劑。尤其適宜之兩性離子表面活性劑係甜菜鹼,例如N-烷基-N,N-二甲基甘胺酸銨、椰油烷基二甲基甘胺酸銨、N-醯基胺基丙基-N,N-二甲基甘胺酸銨、椰油醯基胺基丙基二甲基甘胺酸銨及在烷基或醯基中各自具有8個至18個碳原子之2-烷基-3-羧基甲基-3-羥基乙基咪唑啉以及椰油醯基胺基乙基羥基乙基羧基甲基甘胺酸鹽、N-烷基甜菜鹼、N-烷基胺基甜菜鹼。烷基咪唑啉、烷基肽、脂胺基酸、自乳化基質及如K.F. DePolo,A short textbook of cosmetology,第8章,表8-7,第250頁至第251頁中所闡述之化合物。
非離子乳化劑,例如PEG-6蜂蠟(及)PEG-6硬脂酸酯(及)聚甘油-2異硬脂酸酯[Apifac]、硬脂酸甘油酯(及)PEG-100硬脂酸酯[Arlacel 165]、PEG-5硬脂酸甘油酯[arlatone 983 S]、山梨醇酐油酸酯(及)聚甘油基-3蓖麻醇酸酯[Arlacel 1689]、山梨醇酐硬脂酸酯及蔗糖椰油酸酯[arlatone 2121]、硬脂酸甘油酯及月桂醇聚醚-23[Cerasynth 945]、鯨蠟硬脂醇及鯨蠟醇聚醚-20[Cetomacrogol蠟]、鯨蠟硬脂醇及聚山梨酸酯60及PEG-150及硬脂酸酯-20[Polawax GP 200,Polawax NF]、鯨蠟硬脂醇及鯨蠟基聚葡糖苷[Emulgade PL 1618]、鯨蠟硬脂醇及鯨蠟硬脂醇聚醚-20[Emulgade 1000NI、Cosmowax]、鯨蠟硬脂醇及PEG-40蓖麻油[Emulgade F Special]、鯨蠟硬脂醇及PEG-40蓖麻油及鯨蠟基硫酸鈉[Emulgade F]、硬脂醇及硬脂醇聚醚-7及硬脂醇聚醚-10[Emulgator E 2155]、鯨蠟醇及硬脂醇聚醚-7及硬脂醇聚醚-10[Emulsifying wax U.S.N.F]、硬脂酸甘油酯及PEG-75硬脂酸酯[Gelot 64]、丙二醇鯨蠟醇聚醚-3乙酸酯[Hetester PCS]、丙二醇異鯨蠟醇-3乙酸酯(isoceth-3 acetate)[Hetester PHA]、鯨蠟硬脂醇及鯨蠟醇聚醚-12及油醇聚醚-12[Lanbritol Wax N 21]、PEG-6硬脂酸酯及PEG-32硬脂酸酯[Tefose 1500]、PEG-6硬脂酸酯及鯨蠟醇聚醚-20及硬脂醇聚醚-20[Tefose 2000]、PEG-6硬脂酸酯及鯨蠟醇聚醚-20及硬脂酸甘油酯及硬脂醇聚醚-20[Tefose 2561]、硬脂酸甘油酯及鯨蠟硬脂醇聚醚-20[Teginacid H,C,X]。
陰離子乳化劑,例如PEG-2硬脂酸酯SE、硬脂酸甘油酯SE[Monelgine,Cutina KD]、丙二醇硬脂酸酯[Tegin P]、鯨蠟硬脂醇及鯨蠟基硫酸鈉[Lanette N,Cutina LE,Crodacol GP]、鯨蠟硬脂醇及月桂基硫酸鈉[Lanette W]、三月桂醇聚醚-4磷酸酯及硬脂酸乙二醇酯及PEG-2硬脂酸酯[Sedefos 75]、硬脂酸甘油酯及月桂基硫酸鈉[Teginacid Special]。陽離子酸性基質,例如鯨蠟硬脂醇及西曲溴銨(cetrimonium bromide)。
乳化劑以組合物總重量計可以(例如)1重量%至30重量%、尤其4重量%至20重量%且較佳5重量%至10重量%之量使用。
當調配於O/W乳液中時,該等乳化劑系統之較佳量可表示為油相的5%至20%。
適宜用作超脂劑之物質係(例如)羊毛脂及卵磷脂以及聚乙氧基化或丙烯酸酯化羊毛脂及卵磷脂衍生物、多元醇脂肪酸酯、單甘油酯及脂肪酸鏈烷醇醯胺,後者同時充當發泡體穩定劑。
適宜溫和表面活性劑(即尤其皮膚耐受良好之表面活性劑)之實例包括脂肪醇聚乙二醇醚硫酸鹽、單甘油酯硫酸鹽、單-及/或二-烷基磺基琥珀酸鹽、脂肪酸羥乙基磺酸鹽、脂肪酸肌胺酸鹽、脂肪酸牛磺酸鹽、脂肪酸麩胺酸鹽、α-烯烴磺酸鹽、醚羧酸、烷基葡聚寡糖、脂肪酸葡萄糖醯胺、烷基醯胺基甜菜鹼及/或蛋白脂肪酸縮合產物,後者較佳基於小麥蛋白。
二氧化矽、矽酸鎂、矽酸鋁、多糖或其衍生物(例如透明質酸)、黃原膠、瓜耳膠、瓊脂、海藻酸鹽、角叉菜膠、膠凝糖、果膠、或經改良之纖維素(例如羥基纖維素、羥基丙基甲基纖維素)。另外,聚丙烯酸酯或網狀丙烯酸均聚物及聚丙烯醯胺、卡波姆(carbomer)(卡波普(carbopol)型980、981、1382、ETD 2001、ETD 2020、Ultrez 10)或Salcare系列(例如Salcare SC80(硬脂醇聚醚-10烯丙基醚/丙烯酸酯共聚物)、Salcare SC81(丙烯酸酯共聚物)、Salcare SC91及Salcare AST(丙烯酸鈉共聚物/PPG-1十三烷醇聚醚-6))、sepigel 305(聚丙烯醯胺/月桂醇聚醚-7)、Simulgel NS及Simulgel EG(羥基乙基丙烯酸酯/丙烯醯二甲基牛磺酸鈉共聚物)、Stabilen 30(丙烯酸酯/異癸酸乙烯基酯交聯聚合物)、Pemulen TR-1(丙烯酸酯/丙烯酸C10-30烷基酯交聯聚合物)、Luvigel EM(丙烯酸鈉共聚物)、Acu1yn 28(丙烯酸酯/山萮醇聚醚-25甲基丙烯酸酯共聚物)等。
適宜之陽離子聚合物係(例如)陽離子纖維素衍生物(例如以Polymer JR 400名稱自Amerchol獲得之四級銨化羥基甲基纖維素)、陽離子澱粉、二烯丙基銨鹽與丙烯醯胺之共聚物、四級銨化乙烯基吡咯啶酮/乙烯基咪唑聚合物(例如Luviquat(BASF))、聚乙二醇與胺之縮合產物、四級銨化膠原多肽(例如月桂基二甲基銨羥丙基水解膠原(LamequatL/Grnau))、四級銨化小麥多肽、聚乙烯亞胺、陽離子聚矽氧聚合物(例如胺端聚二甲基矽氧烷)、己二酸與二甲胺基羥丙基二伸乙基三胺之共聚物(Cartaretin/Sandoz)、丙烯酸與二甲基二烯丙基氯化銨之共聚物(Merquat 550/Chemviron)、如(例如)FR-A-2 252 840中所闡述之聚胺基聚醯胺及其交聯水溶性聚合物、陽離子殼多糖衍生物(例如視情況呈微晶形式分佈之四級銨化殼聚糖);二鹵代烷基化物(例如二溴丁烷)與雙(二烷基)胺(例如雙(二甲基胺基)-1,3-丙烷)之縮合產物、陽離子瓜爾膠(例如購自Celanese之Jaguar C-17、Jaguar C-16)、四級銨化銨鹽聚合物(例如購自Miranol之Mirapol A-15、Mirapol AD-1、Mirapol AZ-1)。可考慮陰離子、兩性離子、兩性及非離子聚合物,例如乙酸乙烯酯/巴豆酸共聚物、乙烯基吡咯啶酮/丙烯酸乙烯基酯共聚物、乙酸乙烯酯/馬來酸丁基酯/丙烯酸異冰片基酯共聚物、甲基乙烯基醚/馬來酸酐共聚物及其酯、未交聯聚丙烯酸及與多元醇交聯之聚丙烯酸、丙烯醯胺基丙基-三甲基氯化銨/丙烯酸酯共聚物、辛基丙烯醯胺/甲基丙烯酸甲酯、甲基丙烯酸第三丁基胺基乙基酯/甲基丙烯酸2-羥基丙基酯共聚物、聚乙烯基吡咯啶酮、乙烯基吡咯啶酮/乙酸乙烯酯共聚物、乙烯基吡咯啶酮/甲基丙烯酸二甲基胺基乙基酯/乙烯基己內醯胺三聚物以及視情況衍生之纖維素醚及聚矽氧。此外,可使用如EP 1093796(第3頁至第8頁,第17段至第68段)中所闡述之聚合物。
鯨蠟基三甲基溴化銨(CTAB)、聚二甲基矽氧烷共聚醇、胺端聚二甲基矽氧烷、丙烯醯胺基丙基三甲基氯化銨/丙烯醯胺共聚物、瓜爾羥丙基三甲基氯化銨、如International Cosmetic Ingredient Dictionary and Handbook,第7版,1997中所列示之羥基鯨蠟基羥基乙基二甲基氯化銨四級銨化合物(例如四級銨-80)、如International Cosmetic Ingredient Dictionary and Handbook,第7版,1997中所列示之聚四級銨化合物(例如聚四級銨-5、聚四級銨-6、聚四級銨-7、聚四級銨-10、聚四級銨-11、聚四級銨-17、聚四級銨-18、聚四級銨-24或聚四級銨-27、聚四級銨-28、聚四級銨-32、聚四級銨-37)。
生物源活性成份欲理解為意指(例如)生育酚、生育酚乙酸酯、生育酚棕櫚酸酯、抗壞血酸、脫氧核糖核酸、視黃醇、沒藥醇、尿囊素、植烷三醇、泛醇、AHA酸、胺基酸、神經醯胺、類神經醯胺、精油、植物萃取物及維生素複合物。
除臭活性成份係(例如)止汗劑,例如水合氯化鋁(參見J. Soc. Cosm. Chem. 24,281(1973))。舉例而言,尤佳使用以商標名Locron自Hoechst AG,Frankfurt(FRG)購得之對應於式Al2(OH)5Cl x 2.5 H2O之水合氯化鋁(參見J. Pharm. Pharmacol. 26,531(1975))。除水合氯化物外,亦可使用羥基乙酸鋁及酸式鋁鹽/鋯鹽。可添加酯酶抑制劑作為其他除臭活性成份。該等抑制劑較佳為檸檬酸三烷基酯,例如檸檬酸三甲基酯、檸檬酸三丙基酯、檸檬酸三異丙基酯、檸檬酸三丁基酯且尤其檸檬酸三乙基酯(Hydagen CAT,Henkel),其可抑制酶活性且因此減少臭味形成。可考慮作為酯酶抑制劑之其他物質係甾醇硫酸酯或磷酸酯(例如羊毛甾醇、膽固醇、芸苔甾醇、豆甾醇及穀甾醇硫酸酯或磷酸酯)、其二羧酸及酯(例如戊二酸、戊二酸單乙基酯、戊二酸二乙基酯、己二酸、己二酸單乙基酯、己二酸二乙基酯、丙二酸及丙二酸二乙基酯)及其羥基羧酸及酯(例如檸檬酸、蘋果酸、酒石酸或酒石酸二乙基酯)。在製劑中(尤其在黏稠製劑中)同樣可存在影響病菌菌落並殺死或抑制汗液分解細菌生長之抗菌活性成份。實例包括殼聚糖、苯氧乙醇及葡萄糖酸氯己定。亦已證實5-氯-2-(2,4-二氯苯氧基)-苯酚(Triclosan,Irgasan,BASF)尤其有效。
可使用之去頭屑劑係(例如)氯咪巴唑(climbazole)、羥甲辛吡酮(octopirox)及吡硫鋅(zinc pyrithione)。習用成膜劑包括(例如)殼聚糖、微晶殼聚糖、四級銨化殼聚糖、聚乙烯基吡咯啶酮、乙烯基吡咯啶酮/乙酸乙烯酯共聚物、含有高比例丙烯酸之四級纖維素衍生物聚合物、膠原、透明質酸及其鹽及類似化合物。
為改良流動行為,亦可使用水溶助劑,例如具有低碳原子數之乙氧基化或非乙氧基化單醇、二醇或多元醇或其醚(例如乙醇、異丙醇、1,2-二丙二醇、丙二醇、甘油、乙二醇、乙二醇單乙基醚、乙二醇單丁基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單丁基醚、二乙二醇單甲基醚;二乙二醇單乙基醚、二乙二醇單丁基醚及類似產品)。用於彼用途之多元醇較佳包含2個至15個碳原子及至少兩個羥基。多元醇亦可含有其他官能基(尤其胺基)及/或可經氮修飾。典型實例如下:甘油、烷二醇(例如乙二醇、二乙二醇、丙二醇、丁二醇、己二醇)以及平均分子量為100至1000道爾頓(Dalton)之聚乙二醇;本質縮合度為1.5至10之工業級寡聚甘油混合物,例如二甘油含量為40重量%至50重量%之工業級二甘油混合物;羥甲基化合物,尤其例如三羥甲基乙烷、三羥甲基丙烷、三羥甲基丁烷、新戊四醇及二新戊四醇;低碳數烷基葡糖苷,尤其彼等在烷基中具有1個至8個碳原子者,例如甲基及丁基葡糖苷;具有5個至12個碳原子之糖醇,例如山梨醇或甘露醇;具有5個至12個碳原子之糖,例如葡萄糖或蔗糖;胺基糖,例如葡糖胺;二醇胺,例如二乙醇胺或2-胺基-1,3-丙二醇。
適宜之防腐劑包括(例如)對羥苯甲酸甲基酯、對羥苯甲酸乙基酯、對羥苯甲酸丙基酯、對羥苯甲酸丁基酯、苯紮氯銨、2-溴-2-硝基-丙烷-1,3-二醇、脫氫乙酸、尿素醛、2-二氯-苄基醇、二羥甲基二甲基乙內醯脲、甲醛溶液、甲基二溴戊二腈、苯氧乙醇、羥甲基甘胺酸鈉、咪唑烷基脲、三氯生(triclosan)及下列參考文獻中所列示之其他物質類別:K.F. Depolo-A Short Textbook Of Cosmetology,第7章,表7-2、7-3、7-4及7-5,第210頁至第219頁。
抑菌劑之典型實例係對革蘭陽性細菌具有特定作用之防腐劑,例如2,4,4'-三氯-2'-羥基二苯基醚、氯己定(chlorhexidine)(1,6-二(4-氯苯基-雙胍)己烷)或TCC(3,4,4'-三氯二苯脲)。許多種芳香族物質及香精油亦具有抗微生物性質。典型實例係丁香油、薄荷油及麝香草油中之活性成份丁香酚、薄荷腦及麝香草酚。令人感興趣之天然除臭劑係萜醇法尼醇(3,7,11-三甲基-2,6,10-十二碳三烯-1-醇),其存於萊姆花油中。亦已證實甘油單月桂酸酯係抑菌劑。所存在額外抑菌劑之量以製劑固體含量計,通常為0.1重量%至2重量%。
天然及/或合成芳香族物質之混合物。天然芳香族物質係(例如)來自下列之萃取物:花(百合花、薰衣草、玫瑰、茉莉、橙花、依蘭)、莖及葉(天竺葵、廣藿香、橙葉);果實(茴香籽、胡妥、貢蒿、杜松)、果皮(佛手柑、檸檬、柑橘)、根(肉豆蔻、當歸、芹菜、小豆蔻、閉鞘薑、鳶尾、菖蒲)、木材(松木、檀香木、愈創木、杉木、紅木)、藥草及牧草(龍嵩、香茅草、鼠尾草、百里香)、針葉及嫩枝(雲杉、松樹、歐洲赤松、山松)、樹脂及香脂(白松香、欖香脂、安息香、沒藥、乳香、甜沒藥)。亦可考慮動物原料,例如麝貓香及海狸香。典型合成芳香族物質係(例如)酯、醚、醛、酮、醇或烴型產品。酯型芳香族物質化合物係(例如)乙酸苄基酯、異丁酸苯氧基乙基酯、乙酸對-第三丁基環己基酯、乙酸沉香酯、乙酸二甲基苄基甲酯、乙酸苯基乙基酯、苯甲酸沉香酯、甲酸苄基酯、甘胺酸乙基甲基苯基酯、丙酸烯丙基環己基酯、丙酸蘇合香酯及水楊酸苄基酯。醚包括(例如)苄基乙基醚;醛包括(例如)具有8個至18個碳原子之直鏈烷醛、檸檬醛、香茅醛、香茅基氧基乙醛、兔耳草醛、羥基香茅醛、鈴蘭醛及波潔紅醛;酮包括(例如)紫羅蘭酮、異甲基紫羅蘭酮及甲基柏木酮;醇包括(例如)茴香腦、香草醇、丁香酚、異丁子香酚、香葉醇、沈香醇、苯基乙基醇及萜品醇;及烴,主要包括萜類及香脂。然而,較佳使用可共同產生有吸引力氣味之各種芳香族物質之混合物。揮發性相對較低之香精油(其主要用作芳香組份)亦適宜作為芳香油,例如鼠尾草油、洋甘菊油、丁香油、蜂花油、肉桂油、萊姆花油、杜松子油、岩蘭草油、乳香油、白松香油、勞丹油及熏衣類油。較佳單獨或彼此混合使用佛手柑油、二羥基月桂烯醇、鈴蘭醛、新鈴蘭醛、香草醇、苯基乙基醇、己基肉桂醛、香葉醇、苄基丙酮、兔耳草醛、沈香醇、乙氧基甲氧基環十一烷、龍涎呋喃(ambroxan)、吲哚、希蒂鶯(hedione)、賽得利(sandelice)、檸檬油、紅桔油、橙油、乙醇酸烯丙基戊基酯、賽羅沃特(cyclovertal)、熏衣類油、香紫蘇油、大馬酮、天竺葵香葉油、水楊酸環己基酯、甲基柏木酮、龍涎酮(iso-E-Super)、吐納麝香(Fixolide)NP、依沃尼(evernyl)、α-異甲基紫羅蘭酮、苯基乙酸、乙酸香葉酯、乙酸苄基酯、玫瑰醚、瑞米萊特(romillat)、依瑞替(irotyl)及氟羅邁特(floramat)。
此外,化妝品製劑可能含有佐劑、消泡劑(例如聚矽氧)、結構劑(例如馬來酸)、增溶劑(例如乙二醇、丙二醇、甘油或二乙二醇)、遮光劑(例如乳膠、苯乙烯/PVP或苯乙烯/丙烯醯胺共聚物)、推進劑(例如丙烷/丁烷混合物、N2O、甲醚、CO2、N2或空氣),所謂的偶聯劑及顯影劑組份(如氧化染料前體)、還原劑(例如硫代乙醇酸及其衍生物、硫代乳酸、半胱胺、硫代蘋果酸或巰基乙磺酸)、或氧化劑(例如過氧化氫、溴酸鉀或溴酸鈉)。
適宜之驅蟲劑係(例如)N,N-二乙基-間-甲苯醯胺、1,2-戊二醇或驅蟲劑3535;適宜之仿曬劑係(例如)二羥基丙酮及/或赤藻酮糖或二羥基丙酮及/或二羥基丙酮前體(如WO 01/85124中所闡述)及/或赤藻酮糖。
本發明穩定劑系統尤其適用於穩定身體護理產品,具體而言:
- 皮膚護理製劑,例如皮膚洗滌及清潔製劑,其呈錠劑形式或液體皂、非皂性清洗劑或洗滌膏之形式,
- 沐浴製劑,例如液體(沐浴露、牛奶、淋浴製劑)或固體沐浴製劑(例如沐浴磚及浴鹽);
- 皮膚護理製劑,例如潤膚乳、多功能乳液或護膚油;身體油、身體洗劑、身體凝膠;護膚膏;
- 個人護理化妝品製劑,例如呈日霜或粉霜形式之面部美容產品、蜜粉(鬆散或壓縮)、腮紅或隔離霜、眼部護理製劑(例如眼影製劑、睫毛膏、眼線筆、眼霜或眼部修護霜);唇部護理製劑(例如唇膏、唇彩、唇線筆)指甲護理製劑(例如指甲油、洗甲油、護甲劑或角質去除劑);
- 足部護理製劑,例如足部沐浴用品、足粉、足霜或足部香脂、特定除臭劑及止汗劑或除繭製劑;
- 防曬製劑,例如防曬乳、防曬洗劑、防曬霜或防曬油、防曬隔離霜或熱帶用防曬用品(tropicals)、日曬前製劑(pre-tanning preparations)或日曬後製劑;
- 皮膚曬黑製劑,例如仿曬霜;
- 脫色製劑,例如用於漂白皮膚之製劑或皮膚增白製劑;
- 驅蟲劑,例如驅蟲油、洗劑、噴霧或貼片;
- 除臭劑,例如除臭噴霧、手壓式噴霧、除臭凝膠、貼片或走珠;
- 止汗劑,例如止汗貼片、乳霜或走珠;
- 用於暗瘡皮膚之清潔及護理製劑,例如合成清洗劑(固體或液體)、去角質或磨砂製劑或去角質面膜;
- 呈化學形式之脫毛製劑(脫毛法),例如脫毛粉、液體脫毛製劑、霜或膏形式的脫毛製劑、呈凝膠形式或氣溶膠發泡體之脫毛製劑;
- 刮鬍製劑,例如刮鬍皂、發泡體型刮鬍霜、非發泡體型刮鬍霜、發泡體及凝膠、用於乾式刮鬍之刮鬍前製劑、刮鬍後用品或刮鬍後洗劑;
- 芳香劑製劑,例如含有芳香劑及芳香物質之製劑(香水、古龍水、淡香水、濃香水、淡香精、香料)、芳香油或芳香霜;
- 頭髮保養化妝品製劑,例如呈洗髮精形式之洗髮製劑及護髮素;頭髮護理製劑,例如預保養製劑、育髮露、造型霜、造型凝膠、潤髮油、洗髮劑、保養包(treatment packs)、護髮精華素;頭髮成型製劑,例如用於燙髮液(熱燙髮液、溫和燙髮液、冷燙發液)之燙髮製劑、直發製劑、液體頭髮定型製劑、定型發泡體、定型噴霧;漂白製劑,例如過氧化氫溶液、亮發洗髮精、漂白霜、漂白粉、漂白膏或油;臨時性、半永久性或永久性染髮劑、含有自氧化染料之製劑、或天然染髮劑(例如指甲花或洋甘菊);
- 潔齒劑,具體而言牙霜、牙膏、漱口劑、口腔清洗劑、抗牙斑製劑及假牙清潔劑;
- 彩妝性製劑,具體而言唇膏、指甲油、眼影、睫毛膏、乾及濕粉餅、腮紅、粉劑、脫毛劑及曬黑洗劑
- 含有活性成份之化妝品調配物,具體而言激素製劑、維生素製劑、植物萃取物製劑及抗菌製劑。
含有活性成份之適宜化妝品調配物具體而言係激素製劑、維生素製劑、植物萃取物製劑及抗菌製劑。
所列示之最終調配物可以多種存在形式存在、例如:
- 以液體製劑形式、如W/O、O/W、O/W/O、W/O/W或PIT乳液及各種微乳液,
- 以凝膠形式,
- 以油、乳霜、乳液或洗劑形式,
- 以貼片形式,
- 以噴霧(利用推進氣體或手壓式噴霧進行噴霧)或氣溶膠形式,
- 以發泡體形式,或
- 以膏糊形式。
對於皮膚尤其重要之化妝品製劑係防曬製劑,例如防曬乳、防曬洗劑、防曬霜、防曬油、防曬隔離霜或熱帶用防曬用品、日曬前製劑或日曬後製劑、以及皮膚曬黑製劑(例如仿曬霜)。尤其令人感興趣者係防曬乳霜、防曬洗劑、防曬乳及呈噴霧形式之防曬製劑。
對於頭髮尤其重要之化妝品製劑係上述用於頭髮保養之製劑,尤其呈洗髮精形式之洗髮製劑、護髮素、頭髮護理製劑(例如預保養製劑)、育髮露、造型霜、造型凝膠、潤髮油、洗髮劑、保養包、護髮精華素、直發製劑、液體頭髮定型製劑、定型發泡體、定型噴霧。尤其令人感興趣者係呈洗髮精形式之洗髮製劑。
洗髮精具有(例如)下列組合物:0.01重量%至5重量%的式(1)化合物,12.0重量%的月桂醇聚醚-2-硫酸鈉,4.0重量%的椰油醯胺基丙基甜菜鹼,3.0重量%的氯化鈉,及添加至100%的水。
舉例而言,尤其可使用下列頭髮化妝品調配物:
a1)自發乳化原料調配物,其包含本發明式(1)化合物、視情況另一種穩定劑、PEG-6-C10側氧基醇及倍半油酸山梨醇酐,向其中添加水及任一期望四級銨化合物(例如4%貂油醯胺基丙基二甲基-2-羥基乙基氯化銨或四級銨80);
a2)自發乳化原料調配物,其包含本發明式(1)化合物、視情況另一種穩定劑、檸檬酸三丁基酯及PEG-20-山梨醇酐單油酸酯,向其中添加水及任一期望四級銨化合物(例如4%貂油醯胺基丙基二甲基-2-羥基乙基氯化銨或四級銨80);
b) 四元摻雜溶液,其包含存於三乙二醇丁基醚中之本發明式(1)化合物及檸檬酸三丁基酯;及視情況另一種穩定劑;
c) 混合物或溶液,其包含本發明式(1)化合物與烷基吡咯啶酮;及視情況另一種穩定劑。
本發明身體護理產品之實例列示於下表中:
本發明穩定劑系統亦可用於家用清潔及處理劑中,例如用於下列中:洗衣店產品及織物柔軟劑、液體清潔及精煉劑、玻璃清洗劑、中性清潔劑(多用途清潔劑)、酸性家用清潔劑(浴缸)、浴室清潔劑、WC清潔劑,例如用於下列中:洗滌劑、漂洗劑及洗碗劑、廚房及烤箱清潔劑、洗淨劑、洗碗機用清洗劑、鞋油、拋光蠟、地板清洗劑及拋光劑、金屬、玻璃及陶瓷清潔劑、紡織品保養產品、氈毯清潔劑及地毯清潔劑、用於去除鏽漬、色漬及污漬之試劑(去污鹽)、傢具及多用途拋光劑及皮革及乙烯基樹脂修飾劑(皮革及乙烯基樹脂噴霧)及空氣清新劑。
家用清潔劑係具有下列組份中一或多者之水或醇(乙醇或異丙醇)溶液:
- 陰離子、非離子、兩性及/或陽離子表面活性劑;
- 藉由動物及植物油脂皂化製得之皂;
- 無機酸,例如鹽酸、磷酸或硫酸;
- 無機鹼(NaOH或KOH)或有機鹼之鹼性產物;
- 用於改善表面清潔之研磨劑;
- 用於滋養及保護表面之蠟及/或聚矽氧;
- 多磷酸鹽;
- 釋放次氯酸鹽或鹵素之物質;
- 包含漂白活化劑(例如TAED)之過氧化物、例如過硼酸鈉或H2O2;
- 酶;
- 洗滌時清洗劑褪色抑制劑、去污化合物、除垢劑、消泡劑、螢光增白劑;
- 基於蠟之清潔劑可包含選自石油精、松節油及/或石蠟之溶劑及基於蠟之乳化劑;
- 填充劑、例如用於強力清潔劑之矽酸鹽、多磷酸鹽、沸石;
- 顏料、色澱或可溶染料;
- 香料;及
- 光穩定劑、抗氧化劑及螯合劑。
經著色清潔劑及彩妝性化妝品產品可包含下列染料:
- 無機顏料、例如氧化鐵(氧化鐵紅、氧化鐵黃、氧化鐵黑等)、群青、氧化鉻綠或炭黑;
- 天然或合成有機顏料;
- 可溶於溶劑中之分散性染料,例如HC型直接染髮劑,例如HC紅3號、HC藍2號及列示於International Cosmetic Ingredient Dictionary and Handbook,第7版,1997中之所有其他染髮劑或列示於Color Index International or Society of Dyers and Colourists中之分散性染料;
- 彩色清漆(可溶染料之不溶鹽、例如陰離子染料之大多數Ca-、Ba-或Al-鹽);
- 可溶陰離子或陽離子染料、例如酸性染料(陰離子)、鹼性染料(陽離子)、直接染料、反應性染料或溶劑染料。
通常,對於家用及身體護理產品之著色而言,所有在電磁輻射之可見光(波長為約4000至700 nm)範圍內具有吸收的物質均係適宜的。吸收通常由下列生色團引起:偶氮-(單-、二、三-或多-)均二苯乙烯-、類胡蘿蔔素-、二芳基甲烷-、三芳基甲烷-、呫噸-、吖啶-、喹啉、次甲基-(亦可為多次甲基-)、噻唑-、吲達胺-、靛酚-、吖嗪-、噁嗪、噻嗪-、蒽醌-、靛類-、酞菁-及其他合成、天然及/或無機生色團。
本發明亦係關於家用護理及織物護理產品、例如下水道清潔劑、消毒劑溶液、室內裝飾品清潔劑、汽車護理產品(例如,係關於清潔及/或拋光並保護塗料、輪胎、鉻、乙烯基樹脂、皮革、織物、橡膠、塑膠及織物)、脫脂劑、拋光劑(玻璃、木材、皮革、塑膠、大理石、花崗石及瓦片等)、及金屬拋光劑及清潔劑。抗氧化劑適用於保護上文產品以及乾燥片中之芳香劑。本發明亦係關於家用護理產品、例如蠟燭、凝膠蠟燭、空氣清新劑及香薰油(家用)。
家用清潔及處理劑之典型實例列示於下表中:
本發明式(1)之苯并酚酮衍生物係(例如)藉由溶於油相或醇或水相(視需要在高溫下)而納入。
本發明身體護理產品及家用產品對存於此等產品中之成份之顏色變化及化學降解具有高穩定性。舉例而言,已發現包含染料之本發明組合物具有極佳之顏色穩定性。
下列實例闡釋本發明。
在下列實例中已使用下表中所列示之穩定劑:
製備下列經著色鹼性洗髮精調配物:
月桂基乙醚硫酸鈉 10%
椰油醯胺丙基甜菜鹼 3%
檸檬酸 至pH 5
FD&C藍色1號 0.002%
穩定劑 0.01%
製備此調配物之下列經穩定及未經穩定之樣品用於光穩定性測試:
1.未經穩定之鹼性洗髮精調配物
2.鹼性洗髮精調配物+0.01%的式(B-1)化合物
3.鹼性洗髮精調配物+0.01%的式(B-2)化合物
4.鹼性洗髮精調配物+0.01%的式(B-32)化合物
5.鹼性洗髮精調配物+0.01%的式(B-18)化合物
將調配物填充至30 ml玻璃瓶中並在ATLAS日光測試器XLS+Xenon燈(光強度為500 W/m2,將光譜調節至室內條件,樣品室溫度:32℃)中進行輻照。
輻照15小時後的結果。
輻照30小時後的結果。
所有穩定劑均顯著增加調配物之穩定性。本發明式(B-18)之穩定劑另外展示不改變初始顏色之益處,若特定預期色度不允許經著色組份變黃,則此甚為有利。
製備下列經著色鹼性洗髮精調配物:
月桂基乙醚硫酸鈉 10%
椰油醯胺丙基甜菜鹼 3%
檸檬酸 至pH 5
染料 0.002%
穩定劑 0.01%
將調配物分別用PURICOLOR藍ABL9(BASF、FD&C藍1號、酸性藍9)、及PURICOLOR紅ARE33(BASF、D&C紅33、酸性紅33)著色。
製備此調配物之下列經穩定及未經穩定之樣品用於光穩定性測試:
1.未經穩定之鹼性洗髮精調配物
2.鹼性洗髮精調配物+0.01%的式(B-18)化合物
3.鹼性洗髮精調配物+0.01%的TINOGARD TL(BASF)
將調配物填充至30 ml玻璃瓶中並在ATLAS日光測試器XLS+Xenon燈(光強度為500 W/m2,將光譜調節至室內條件,樣品室溫度:32℃)中進行輻照。
輻照12小時後經藍色染料著色之洗髮精之結果。
輻照25小時後經藍色染料著色之洗髮精之結果。
輻照10小時後經紅色染料著色之洗髮精之結果。
輻照25小時後經紅色染料著色之洗髮精之結果。
式(B-18)化合物表現顯著優於具有兩種測試染料之現有技術寬帶UV吸收劑(例如TINOGARD TL)。
製備此調配物之下列經穩定及未經穩定之樣品用於光穩定性測試:
1.純蓖麻油
2.含有0.1%式(B-32)化合物之蓖麻油
3.含有0.1%抗氧化劑TINOGARD TT(BASF)之蓖麻油
4.含有0.1%抗氧化劑BHT之蓖麻油
5.含有0.1%槲皮素之蓖麻油
將樣品放置於RACIMAT中並加熱至140℃。將空氣流動調節為15 L/min。氣流鼓泡通過各加熱樣品且然後通過貯水池。因此,氧化過程所形成的所有揮發性有機化合物均藉助氣流帶入貯水池。在量測期間在線監測貯水池之導電性。在氧化開始後,揮發性有機化合物(例如甲酸)轉移至貯水池中,使得導電性快速(指數)增加。直至氧化開始為止的時間稱為「誘導時間」。
結果列示於下表中。
樣品2(其包含本發明穩定劑)展示比現有技術抗氧化劑(例如TINOGARD TT(Ciba)或BHT)更佳的氧化穩定性,且表現亦顯著優於天然多酚結構(例如槲皮素)。
在室溫下將組份(A)分散。
在加熱下將(B)混合直至對羥基苯甲酸酯完全溶解為止且然後邊輕輕攪拌將(B)添加至(A)中。
將(C)摻和直至其完全溶解為止並在攪拌下緩慢添加至(A)與(B)之混合物中。
將(D)摻和直至完全溶解為止並在攪拌下緩慢添加至(A)、(B)及(C)之混合物中。
可藉由添加少量的三乙醇胺(pH=5.6-5.75)來增加凝膠透明度。
製備:將表面活性劑與水摻和直至獲得均勻溶液為止。用檸檬酸將pH調節至6.0-6.5。添加其他組份,將穩定劑與香薰油預先混合。將混合物攪拌直至其完全溶解為止。
製備:在50℃下將各組份按指定順序充分混合。獲得透明均勻溶液。
家用產品調配物之製備
製備:將各組份按指定順序溶解直至獲得透明均勻混合物為止。
製備:將各組份按指定順序攪拌直至獲得均勻混合物為止。
將1,7-二丁基-2,3,4,6-四羥基-5H-苯并環庚-5-酮(CAS-第16492-78-7號)(1.4 g)溶於40 ml甲苯及0.8 ml原甲酸三乙酯中並加熱至120℃,直至乙醇蒸發結束為止。然後將混合物蒸發至乾燥並在自矽膠過濾以去除黑色雜質後,將殘餘物自二噁烷凍乾。所得黃色粉末可溶於己烷中。
1H-NMR(CDCl3,300 MHz):9.00(OH);7.45(d,1 H);6.82(d,1 H);3.65(dq,1 H);3.53(dq,1 H);2.85(t,2 H);2.72(t,2 H);1.88(s,3 H);1.48-1.66(m,4 H);1.29-1.45(m,4 H);1.18(t,3 H);0.90(dt,6 H)。
13C-NMR(CDCl3,75 MHz):13.88;13.95;14.74;22.51;22.75;24.80;26.29;31.23;31.94;34.11;58.45;112.85;119.40;127.11;129.45;129.52;132.62;133.91;144.66;150.61;152.75;181.76。
在室溫下將0.50 g兒茶酚(44.3 mmol,98%)及1.28 g沒食子酸辛基酯(44.3 mmol,98%)溶於30 ml鄰苯二甲酸鹽緩衝液(pH=5)及10 mL乙酸乙酯中。
添加3.0 mg(21.8 U/mg)市售(Sigma-Aldrich)變色栓菌(T. versicolor)漆酶並在室溫下將混合物攪拌2天。
然後分離出有機相並在真空中濃縮,得到1.02 g粗製化合物B-2。自乙醇/水重結晶後,得到1.26 g呈深橙色粉末形式之預期產物B-2。熔點:79℃(分解)。
1H-NMR(DMSO,300 MHz):14.77(s,1H,OH),10.00(s,2H,2OH);8.27(s,1 H);7.612(m,2 H);7.48(d,1 H);4.28(t,2 H);1.73(m,2 H);1.16-1-42(m,10 H);0.85(t,3 H)。
在室溫下將6.74 g兒茶酚(60 mmol,98%)及8.66 g沒食子酸丙基酯(40 mmol,98%)溶於400 mL磷酸鹽緩衝液(pH=5)及120 mL乙酸乙酯中。
添加45.2 mg(21.8 U/mg)市售變色栓菌漆酶並在室溫下將混合物攪拌4天。
然後分離出有機相並在真空中濃縮,得到13.40 g粗產物。自水重結晶後,得到7.34 g呈橙色粉末形式之預期產物B-1。熔點:139℃。
1H-NMR(DMSO,300 MHz):14.75(s,1H,OH),10.15(s,1H,OH);9.90(s,1 H,OH);8.26(s,1 H);7.61(d,1 H);7.60(s,1 H);7.48(d,1 H);4.25(t,2 H);1.76(m,2 H),0.99(t,3 H)。
向3.00 g紅棓酚於40 ml吡啶中之溶液中逐滴添加2.56 ml乙酸酐。在100℃下攪拌1 h後,將混合物蒸發至乾燥並將橙色殘餘物懸浮於乙醚中。濾出沉澱並在真空中乾燥,得到0.59 g粗製化合物B-32。在乙醚/乙酸乙酯(1:1)中煮沸後,獲得0.42 g呈黃色粉末形式之預期產物。
1H-NMR(DMSO,360 MHz):15.29(s,1H);11.38(s,1 H);7.57(d,J=11.6,1 H);7.35(d,J=8.95,1 H);6.99(s,1 H);6.78(dd,1 H);2.34(s,3 H);2.30(s,3 H)。
將紅棓酚(0.50 g)溶於20 ml甲苯及0.43 ml原甲酸三乙酯中並加熱至120℃,直至乙醇蒸發結束為止。然後將所得橙色懸浮液蒸發至乾燥並在二氯甲烷中攪拌殘餘物。濾出沉澱並在真空中在25℃下乾燥。分離得到450 mg呈橙色粉末形式之預期產物。
1H-NMR(CDCl3,360 MHz):14.61(s,1H);8.56(s,1 H);7.34(d,J=11.5,1 H);7.19(d,J=9.5,1 H);6.86-6.80(m,2 H);3.72-3.59(m,2 H);1.92(s,3 H);1.24(t,J=7.1,3 H)。
將化合物B-37懸浮於10.0 ml HCl 0.1N水溶液中並在25℃下攪拌18 h。濾出橙黃色沉澱並在真空中乾燥。分離得到0.318 g呈灰棕色粉末形式之預期產物。
1H-NMR(DMSO,360 MHz):15.26(s,1H);7.56(d,1 H);7.33(d,1 H);6.98(s,1 H);6.65(dd,1 H);2.30(s,3 H)。
在室溫下向0.636 g B-23於6.0 ml吡啶中之溶液中添加0.207 ml乙酸酐。在室溫下將褐橙色溶液攪拌1.5 h並添加至30.0 ml冰水中並在0℃下攪拌15 min。濾出橙色懸浮液並在真空中乾燥。分離得到0.620 g呈橙色粉末形式之預期產物。
1H-NMR(DMSO,360 MHz):14.78(s,1H);7.68(d,1 H);7.43(d,1 H);7.26(s,1 H);6.82(dd,1 H);3.59-3.56(m,2 H);2.31(s,3 H);1.89(s,3H);1.16(t,3H)。
將化合物B-1(1.50 g)溶於35 ml甲苯及1.89 ml原甲酸三乙酯中並加熱至120℃,直至乙醇蒸發結束為止。然後將所得橙色懸浮液蒸發至乾燥並在10.0 ml乙醚中攪拌殘餘物。濾出沉澱並在真空中在25℃下乾燥。分離得到1.20 g呈黃色粉末形式之預期產物。
1H-NMR(CDCl3,360 MHz):8.39(s,1H);8.30(s,1 H);7.77(s,1H);7.57(d,1H);7.34(d,1H);4.31(t,2H);3.70-3.57(m,2 H);1.98(s,3 H);1.84-1.82(m,2 H);1.24(t,3 H);1.06(t,3H)。
在室溫下向0.40 g B-23於4.0 ml吡啶中之溶液中添加2.651 ml乙酸酐。在室溫下將褐色混合物攪拌20 h並添加至40.0 ml冰水中並在0℃下攪拌15 min。濾出灰棕色懸浮液並在真空中乾燥橙黃色殘餘物。分離得到0.198 g呈黃色粉末形式之預期產物。
1H-NMR(CDCl3,360 MHz):7.14(d,1 H);6.92(s,1 H);6.78(d,1 H);6.52-6.47(m,1 H);3.703.54(m,2 H);2.35(s,3 H);2.29(s,3H);1.87(s,3 H);1.21(t,3H)。
在室溫下將化合物B-1(0.35 g)溶於4.0 ml吡啶中。逐滴添加0.50 ml乙酸酐並在室溫下將溶液攪拌16 h。然後將混合物添加至5.0 ml冰水中並在15℃下攪拌30 min。濾出黃色沉澱,用水洗滌並在真空中在30℃下乾燥。分離得到0.337 g呈黃色粉末形式之預期產物。
1H-NMR(DMSO,360 MHz):8.45(s,1H);8.16(d,1 H);7.88(d,1H);7.50(s,1H);4.31(t,2 H);2.38(s,3 H);2.33(s,3 H);2.30(s,3 H);1.83-1.77(m,2 H);1.03(t,3H)。
在室溫下向0.20 g B-41於4.0 ml HCl 0.1N水溶液中之混合物中添加0.5 ml THF。在60℃下將褐色懸浮液攪拌6 h。然後將混合物蒸發至乾燥並將殘餘物懸浮於水中。濾出褐色沉澱並在真空中在25℃下乾燥。分離得到0.12 g呈褐紅色粉末形式之預期產物。
1H-NMR(DMSO,360 MHz):14.36(s,1H);10.75(s,1 H);8.35(s,1H);7.70(s,1H);7.63(d,1 H);7.37(d,1 H);4.15(t,2 H);2.21(s,3 H);1.67-1.61(m,2 H);0.87(t,3 H)。
在室溫下將化合物B-38(490 mg)溶於2.0 ml吡啶中。逐滴添加0.154 ml乙酸酐並在25℃下將褐色溶液攪拌1 h。然後將混合物添加至5.0 ml冰水中並在15℃下攪拌30 min。濾出黃色沉澱,用水洗滌並在真空中在30℃下乾燥。分離得到0.33 g呈黃色粉末形式之預期產物。
1H-NMR(DMSO,360 MHz):8.40(s,1H);7.85(d,1H);7.60(d,1 H);7.54(s,1 H);4.25(t,2 H);3.53-3.50(m,3 H);2.30(s,3H);1.88(s,3H);1.81-1.71(m,2 H);1.15(t,3H);0.98(t,3H)。
Claims (21)
- 一種下式之苯并酚酮衍生物之用途,其中R1、R2及R7彼此獨立地為氫;C1-C30烷基;或COR8;R3係氫;或COOR9;R4係氫;或C1-C30烷基;R5係氫;羥基;C1-C30-烷氧基;或-O-(CO)-R10;R6係氫;C1-C30烷基;或COR8;或R5與R6可一起形成五或六員環;或R6與R7一起形成五或六員環;且R8、R9、R10彼此獨立地為C1-C30烷基;其用於保護身體護理及家用產品,免於光解及氧化降解。
- 如請求項1之用途,其中R1係氫;COR8;或C1-C30烷基;R2、R4及R5係氫;R3係COOR9;R6及R7彼此獨立地為氫;C1-C30烷基;或COR8;或R6與R7一起形成五或六員環;且R8係如在請求項1中所定義。
- 如請求項2之用途,其中 R1係氫;或CO-CH3;R2、R4及R5係氫;R3係COO-C3H7;R6及R7彼此獨立地為氫;或CO-CH3;或R6與R7一起形成五或六員環。
- 如請求項1之用途,其中R1、R2及R7彼此獨立地為氫;甲基;或-CO-CH3;R3係氫;或-COOR9;R4係氫;或C1-C30烷基;R5係氫;甲氧基;或-O-(CO)-CH3;R6係氫;甲基;或-CO-CH3;或R5與R6可一起形成五或六員環;或R6與R7一起形成五或六員環;且R9係C1-C10烷基。
- 如請求項1之用途,其中使用下列各式化合物
- 如請求項1之用途,其中該產品係用於皮膚及其附屬部位。
- 如請求項6之用途,其中該等身體護理產品選自皮膚護 理產品、沐浴及淋浴添加劑、含有芳香劑及芳香物質之製劑、頭髮護理產品、潔齒劑、除臭及止汗製劑、彩妝性製劑(decorative preparation)、防曬調配物及含有活性成份之製劑。
- 如請求項6之用途,其中該等身體護理產品選自身體油、身體洗劑、身體凝膠、保養乳霜、護膚膏、刮鬍製劑及膚用粉劑。
- 如請求項6之用途,其中該等身體護理產品含有芳香劑及芳香物質,其選自香水、香料、花露水及刮鬍水(刮鬍後製劑)。
- 如請求項6之用途,其中該等身體護理產品係頭髮護理產品且選自洗髮精、護髮素、用於造型及保養頭髮之產品、燙髮劑、定型噴霧及髮蠟、髮膠、固髮劑及染髮劑或漂白劑。
- 如請求項6之用途,其中該等身體護理產品係彩妝性製劑且選自唇膏、指甲油、眼影、睫毛膏、乾及濕粉餅、腮紅、粉劑、脫毛劑及曬黑洗劑。
- 如請求項6之用途,其中該等身體護理產品含有活性成份且選自激素製劑、維生素製劑、植物萃取物製劑及抗細菌製劑。
- 如請求項1之用途,其中該產品係用於家用清潔及處理劑中。
- 如請求項13之用途,其中該等家用清潔及處理劑選自洗滌劑、漂洗劑及洗碗劑、鞋油、拋光蠟、地板清洗劑及 拋光劑、多用途清潔劑、浴缸及廁所清潔劑、廚房清潔劑、洗車精及洗車蠟、中性、酸性及鹼性清潔劑、金屬、玻璃及陶瓷清潔劑、紡織品保養劑、用於去除鏽漬、色漬及污漬之製劑(去污鹽)、漂白劑、傢具及多用途拋光劑、表面保護調配物、膜形成調配物及空氣護理調配物。
- 一種下式化合物,其中R'1、R'2及R'7彼此獨立地為氫;C1-C30烷基;或COR'8;R'3係氫;或COOR'9;R'4係氫;或C1-C30烷基;R'5係氫;羥基;C1-C30-烷氧基;或-O-(CO)-R'10;R'6係氫;C1-C30烷基;或COR'8;或R'5與R'6可一起形成五或六員環;或R'6與R'7一起形成五或六員環;且R'8、R'9、R'10彼此獨立地為C1-C30烷基;條件係在式(1')化合物中R'5與R'6一起形成五或六員環;或者,R'6與R'7一起形成五或六員環。
- 如請求項15之式(1')化合物,其中:R'3係式之基團,其中 R'20係C3-C30烷基R'5係氫;或C1-C12烷基;R'1、R'6及R'7係氫;COR'9;或C1-C30烷基;且R'9係如在式(1')中所定義。
- 如請求項15之化合物,其對應於下式,其中R'21及R'22彼此獨立地為氫;OH;C1-C30烷基;或C1-C30烷氧基,且R'1、R'2、R'3、R'4及R'7係如在式(1')中所定義。
- 如請求項15之化合物,其對應於下式,其中R'21及R'22彼此獨立地為氫;OH;C1-C30烷基;或C1-C30烷氧基;且R'1、R'2、R'3、R'4及R'5係如在式(1')中所定義。
- 一種下式化合物 ,其中R'2及R'4彼此獨立地為C1-C30烷基;R'1、R'5、R'6及R'7係C1-C30烷基;或COR'8;且R'8係如在式(1')中所定義。
- 一種下式化合物,其中 R'3係式之基團;R'20係C3-C30烷基;R'1、R'6及R'7係氫;COR'9;或C1-C30烷基;且R'9係C1-C30烷基。
- 一種如請求項15至20中任一項之式(1')、(2')、(3')、(4')及(5')之化合物之用途,其用於保護身體護理及家用產品,免於光解及氧化降解。
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