CN101035508A - 荧光增白剂作为抗微生物剂的应用 - Google Patents
荧光增白剂作为抗微生物剂的应用 Download PDFInfo
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- CN101035508A CN101035508A CNA2005800343852A CN200580034385A CN101035508A CN 101035508 A CN101035508 A CN 101035508A CN A2005800343852 A CNA2005800343852 A CN A2005800343852A CN 200580034385 A CN200580034385 A CN 200580034385A CN 101035508 A CN101035508 A CN 101035508A
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Abstract
荧光增白剂的应用,用于表面的增白和抗微生物处理,以及化妆品、家用产品、个人护理产品、织物、纸和纸原料、塑料和消毒剂的防腐。
Description
本发明涉及荧光增白剂用于表面的增白和抗微生物处理以及化妆品、家用产品、个人护理产品、织物、纸及纸原料、塑料和消毒剂的防腐。
本发明涉及荧光增白剂用于牙齿的增白和/或表面尤其是牙齿的抗微生物处理。
优选荧光增白剂用于牙齿的增白,条件是荧光增白剂未被交联聚乙烯醇壳覆盖。
此外,优选的荧光增白剂为双-三嗪基-二氨基均二苯代乙烯、2-(均二苯代乙烯-4-基)-萘并三唑、2-(4-苯基均二苯代乙烯-4-基)苯并噁唑、双(唑-2-基)均二苯代乙烯(bis(azol-2-yl)stilbene、1,4-双(苯乙烯基)苯、4,4’-双(苯乙烯基)联苯、1,3-二苯基-2-吡唑啉、双(苯并噁唑-2-基)、双(苯并咪唑-2-基)、2-(苯并呋喃-2-基)-苯并咪唑、香豆素、喹诺酮、萘二甲酰亚胺、季铵化吡啶并三唑、芘衍生物或酰氨基3,7-二氨基-二苯并噻吩-2,8-二磺酸5,5-二氧化物。
更优选的荧光增白剂为具有式(1)-(20)的那些:
具有式(1)的双-三嗪基-二氨基均二苯代乙烯
其中
R1、R2、R3和R4彼此独立地为NR5R6、OR7或杂环;
其中
R5和R6彼此独立地为氢;取代或未取代的C6-C10芳基、C1-C10烷基、N,N’-二C1-C6烷基氨基C1-C10烷基或杂环,和
R7为取代或未取代的C6-C10芳基、C1-C10烷基,
优选
R1、R2、R3和R4彼此独立地为取代或未取代的苯基、NH(C1-C6)烷基、N,N’-二C1-C2烷基氨基C1-C6烷基、NH(C1-C6)烷醇基、NH苯基、O(C1-C6)烷基、NH2、哌啶或吗啉基,和
R7为取代或未取代的苯基、C1-C6烷基;
更优选
R1、R2、R3和R4彼此独立地为未取代的芳基;或SO3H/Na/K、COOR7、CONHR7、CON(R7)取代的芳基;取代或未取代的NH(C1-C6)烷基、N((C1-C6)烷基)2、N,N’-二C1-C2烷基氨基C1-C3烷基、NH(C1-C6)烷醇、N((C1-C6)烷醇)2、NH苯基、O(C1-C6)烷基、NH2、哌啶或吗啉基,和
R7为取代或未取代的苯基、C1-C4烷基;
最优选
R1、R2、R3和R4彼此独立地为未取代的芳基;或SO3H/Na/K、COOR7、CONHR7、CON(R7)取代的芳基、取代或未取代的NH(C1-C2)烷基,N((C1-C2)烷基)2、N,N’-二甲基氨基丙基、NH乙醇、N(乙醇)2、NH苯基、O(C1-C6)烷基、NH2,或吗啉基,和
R7为取代或未取代的苯基、C1-C4烷基;
和SO3H可为游离磺酸或碱金属或碱土金属盐,
或
具有式(2)的2-(均二苯代乙烯-4-基)-萘并三唑
其中
R8和R9彼此独立地为氢、SO3H、CN、卤素;
优选
R8和R9彼此独立地为氢、SO3H、CN或氯;或
具有式(3)的2-(4-苯基均二苯代乙烯-4-基)苯并噁唑
或
具有式(4)的双(唑-2-基)均二苯代乙烯
或
具有式(5)的1,4或2,3’或2,4’-双(苯乙烯基)苯
或
具有式(6)的4,4-双(苯乙烯基)联苯
或
具有式(7)的1,3-二苯基-2-吡唑啉
R10为SO3H、SO2NR11R12,
其中
R11和R12彼此独立地为氢、(C1-C6)烷基-N+(C1-C6)烷基、(C1-C6)烷基-SO3H;
优选
R10为SO3H、SO2NH2、SO2NHCH2CH2CH2N+(CH3)3、SO2NHCH2CH2CH2SO3H,
或
具有式(8)的双-苯并噁唑
其中
R13和R14彼此独立地为氢;取代或未取代的C6-C10芳基、C1-C10烷基、1,2-二苯基乙烯基、COO-C1-C10烷基或SO2-C1-C10烷基,和
R为-C=C-、1,2-二苯基亚乙烯基、1,4-亚萘基或2,5-硫代亚苯基,
优选
R13和R14彼此独立地为氢;取代或未取代的苯基、萘基、噻吩基、C1-C16烷基、1,2-二苯基乙烯基、COO-C1-C6烷基或SO2-C1-C6烷基;
或最优选
或
具有式(9)的双(苯并咪唑-2-基)
其中
R15和R16彼此独立地为氢、取代或未取代的C1-C16烷基或苯基;和
或
具有式(10)的2-(苯并呋喃-2-基)-苯并咪唑
或
香豆素,包括3-苯基-7-氨基香豆素、3-苯基-7-(唑-2-基)香豆素、3,7-双(吡咯基)-香豆素和具有式(11)、(12)、(13)或(14)的化合物
其中
R17和R18彼此独立地为氢或取代或未取代的C1-C6烷基,
其中
R19和R20彼此独立地为NR21R22、OR23或杂环,
其中
R21和R22彼此独立地为氢;取代或未取代的C6-C10芳基、C1-C10烷基和
R23为取代或未取代的C6-C10芳基、C1-C10烷基;
或
具有式(15)的喹诺酮
或
具有式(16)的萘二甲酰亚胺
其中
R24为氢或取代或未取代的C1-C16烷基或苯基,和
其中
R25为氢或取代或未取代的NR26R27、OR28或杂环
其中
R26、R27和R28具有与上面给出的R21、R22和R23相同的定义;或
季铵化吡啶并三唑;
或
具有式(17)的芘
或
具有式(18)的酰氨基3,7-二氨基-二苯并噻吩-2,8-二磺酸5,5-二氧化物
其中
R26和R27彼此独立地为取代或未取代的CO-烷氧基苯甲酰、CO-(C1-C6)烷基、CO-苯基,
或
具有式(19)的双苯乙烯基苯
或
具有式(20)的双苯乙烯基联苯
其中
X和X′彼此独立地为-COO-或-CON(R31)、直接键、氧、硫、-O-C1-C3亚烷基-CON(R31)-、-SO2N(R31)-、-O-C1-C3-亚烷基-COO-或-OCO-,
Y和Y′彼此独立地为直接键、C1-C20亚烷基、直接键,
Z为吡啶、2-吡啶-N-甲基、4-吡啶-N-甲基或N(R28R29(R30)q),和
Z′为吡啶、2-吡啶-N-甲基、4-吡啶-N-甲基或N(R28’R29’(R30)q’),
其中
R28和R28’彼此独立地为未取代或取代的C1-C8-烷基或C3-C4烯基,或R28与R29一起,或R28’与R29’一起,为杂环,R29和R29’彼此独立地为未取代或取代的C1-C8烷基或C3-C4烯基,或R29与R28一起或R29’与R28’一起为杂环,或R28和R29’或R28’和R29′与R30一起为吡啶或甲基吡啶环,R30为氢、未取代或取代的C1-C4烷基或C3-C4烯基,或与R28和R29一起或与R28’和R29’一起为吡啶或甲基吡啶环,R30为氢、未取代或取代的C1-C6-烷基,
A-为无色阴离子,和
n和n′彼此独立地为数0或1,和
m和m′彼此独立地为数0或1,和
p和p′彼此独立地为数0、1、2或3,和
q和q′彼此独立地为数0或1,和
苯核B和C还可被非发色取代基取代;
优选地,
具有式(21)的双苯乙烯基苯
或
具有式(22)的双苯乙烯基联苯
其中
X1和X1′为-COO-或-CONH-、直接键、氧、硫、-OC1-C3亚烷基-CONH-、-SO2NH-、-O-C1-C3亚烷基-COO-或-OCO-,
Y1和Y1′彼此独立地为直接键、C1-C4亚烷基或羟基亚丙基,
Z1和Z1′彼此独立地为吡啶、2-吡啶-N-甲基、4-吡啶-N-甲基或N(R35R36(R37)q”),
其中
R35和R36彼此独立地为C1-C4烷基或在一起为吡咯烷、哌啶、六亚甲基亚胺或吗啉环,或与R37一起为吡啶或甲基吡啶环,
R37为氢、C1-C4烷基、C3-C4烯基、C1-C3烷氧基羰基甲基、苄基,C2-C4-羟基烷基或C2-C4氰基烷基或与R35和R36一起为吡啶或甲基吡啶环,
R32为氢、氯、C1-C4烷基、C3-C4烯基、C1-C3烷氧基或(X1)m-Y1-N(R35R36(R37)q”),或与R33一起为三亚甲基或四亚甲基
R33为氢、氯、C1-C4烷基或C1-C3烷氧基,或与R32一起为三亚甲基或四亚甲基,
R34为氢、氯或甲基,
n1和n1彼此独立地为数0或1,
m1和m1′彼此独立地为数0或1,和
p1和p1′彼此独立地为数0、1、2或3,和
q”为数0或1,和
A-为无色阴离子;
和
更优选的为具有式(40)的双苯乙烯基苯
或
具有式(41)的双苯乙烯基联苯
具有式(42)的双苯乙烯基苯
或
具有式(43)的双苯乙烯基联苯
其中
X4为氧、硫,
Y4为直接键,C1-C4亚烷基,
Z4为N(R40R41(R42)q4),
其中
R40和R41彼此独立地为C1-C4烷基或在一起为吡咯烷、哌啶、六亚甲基亚胺或吗啉环,或与R42一起为吡啶或甲基吡啶环,
R42为氢或C1-C4烷基
R33为氢、氯、C1-C4烷基或C1-C3烷氧基,
R34为氢、氯或甲基,
q4为数0或1。
此外,更优选的荧光增白剂为在上面给出的定义和优先选择内的具有式(1)-(4)和(7)-(10)、(15)、(17)-(20)的那些。
最优选的荧光增白剂为具有式(23)-(34)的化合物:
尤其优选的荧光增白剂为式(26)和(28)的化合物。
在本发明中,一个或多个相同或不同的取代基选自以下取代基,例如合适的C1-C16烷基、C1-C20亚烷基、亚芳基或芳基-C1-C10亚烷基、羟基、C1-C8烷氧基、氰化物、卤化物、芳基、芳烷基、烷芳基和NR40R41,其中
R40和R41各自独立地为氢、未取代或取代的芳基或C1-C6烷基;或C1-C8烷基、C1-C8烷氧基、氰化物和/或卤化物。
优选R40和R42为氢或未取代的C1-C6烷基。
杂环为未取代或取代的芳香或非芳香环,如噻吩基、1,3-噻唑基、1,2-噻唑基、1,3-苯并噻唑基、2,3-苯并噻唑基、咪唑基、1,3,4-噻二唑基、1,3,5-噻二唑基、1,3,4-三唑基、甲基吡啶、吡唑基、苯并咪唑基、苯并吡唑基、吗啉基、吡咯烷、哌啶、六亚甲基亚胺、2-吡啶-N-甲基、4-吡啶-N-甲基、吡啶基、喹啉基、嘧啶基和异噁唑基、氨基二苯基、氨基二苯醚或偶氮次苄基。
芳基为例如未取代或取代的苯基或萘基。
取代或未取代的亚烷基或烷基残基可为直链、支链或C5烷基以上的单环或多环,并可以是未断开的或被杂原子如O、S、CO、N、NH、NR40断开,例如C1-C10亚烷基可为残基,如
-CH2CH2-O-CH2CH2-O-CH2CH2-或-CH2CH2-O-CH2CH2-或-CH2CH2-O-CH2-或-CH2-O-CH2-或-CH2CH2-CH2CH2-O-CH2-CH2-或-CH2CH2-CH(N(CH3)2)-CH2-CH2-或CH2-NH2-CH2-CH2。
C1-C16烷基为例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、环戊基、环己基、正己基、正辛基、1,1′,3,3′-四甲基丁基或2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基。
C1-C10烷基为例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、环戊基、环己基、正己基、正辛基、1,1′,3,3′-四甲基丁基或2-乙基己基、壬基、癸基。
C1-C8烷基为例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、环戊基、环己基、正己基、正辛基、1,1′,3,3′-四甲基丁基或2-乙基己基。
C1-C6烷基为例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、环戊基、环己基、正己基。
C1-C4烷基为例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基。
NH(C1-C6)烷基为例如NH-甲基、NH-乙基、NH-丙基、NH-异丙基、NH-正丁基、NH-仲丁基、NH-叔丁基、NH-正戊基、NH-2-戊基、NH-3-戊基、NH-2,2′-二甲基丙基、NH-环戊基、NH-环己基、NH-正己基。
NH(C1-C6)烷醇为例如NH-甲醇、NH-乙醇、NH-丙醇、NH-异丙醇、NH-正丁醇、NH-仲丁醇、NH-叔丁醇、NH-正戊醇、NH-2-戊醇、NH-3-戊醇、NH-2,2′-二甲基丙醇、NH-环戊醇、NH-环己醇、NH-正己醇。
N,N’-二C1-C6烷基氨基C1-C10烷基为例如N,N’-二甲基氨基甲基、N,N’-二乙基氨基甲基、N,N’-二甲基氨基乙基、N,N’-二丙基氨基乙基、N,N’-二丙基氨基乙基、N,N’-二丙基氨基丙基、N,N’-二异丙基氨基甲基、N,N’-二异丙基氨基乙基、N,N’-二异丙基氨基丙基或N,N’-二己基氨基甲基、N,N’-二辛基氨基乙基、N,N’-二壬基氨基丙基。
N,N’-二C1-C2烷基氨基C1-C6烷基为例如N,N’-二甲基氨基甲基、N,N’-二乙基氨基甲基、N,N’-二甲基氨基乙基、N,N’-二甲基氨基甲基、N,N’-二甲基氨基异丙基、N,N’-二甲基氨基丁基、N,N’-二甲基氨基戊基、N,N’-二甲基氨基己基。
O-烷基与烷氧基相同,并优选代表O(C1-C8)烷基、O(C1-C6)烷基、O(C1-C3)烷基。
O(C1-C8)烷基为例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2′-二甲基丙氧基、环戊氧基、环己氧基、正己氧基、正庚氧基或正辛氧基。
O(C1-C6)烷基为例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2′-二甲基丙氧基、环戊氧基、环己氧基、正己氧基。
O(C1-C3)烷基为例如甲氧基、乙氧基、丙氧基、异丙氧基。
C1-C6烷醇为例如甲醇、乙醇、丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇、正戊醇、2-戊醇、3-戊醇、2,2′-二甲基丙醇、环戊醇、环己醇、正己醇。
C1-C20亚烷基为例如亚甲基、亚乙基、亚丙基、亚异丙基、亚正丁基、亚仲丁基、亚叔丁基、亚正戊基、2-亚戊基、3-亚戊基、2,2′-二甲基亚丙基、亚环戊基、亚环己基、亚正己基、亚正辛基、1,1′,3,3′-四甲基亚丁基或2-乙基亚己基、亚壬基、亚癸基、亚十一烷基、亚十二烷基、亚十三烷基、亚十四烷基、亚十五烷基、亚十六烷基、亚十七烷基、亚十八烷基、亚十九烷基。
C1-C4亚烷基为例如亚甲基、亚乙基、亚丙基、亚异丙基、亚正丁基、亚仲丁基、亚叔丁基。
C1-C3亚烷基为例如亚甲基、亚乙基、亚丙基、亚异丙基。
C3-C4烯基为例如丙烯基、异丙烯基、正丁烯基、仲丁烯基、叔丁烯基。
卤素为例如氟、氯、溴或碘,尤其是氯和氟。
A-为无色阴离子,如有机或无机阴离子,如卤化物,优选氯化物和氟化物,硫酸盐、硫酸氢盐、磷酸盐、四氟化硼、碳酸盐、碳酸氢盐、草酸盐或C1-C8烷基硫酸酯,尤其是硫酸甲酯或硫酸乙酯;阴离子还表示乳酸盐、甲酸盐、醋酸盐、丙酸盐或络合阴离子,如氯化锌复盐。
阴离子尤其为卤化物优选氯化物或氟化物、硫酸盐、硫酸氢盐、硫酸甲酯、磷酸盐、甲酸盐、醋酸盐或乳酸盐。
阴离子更尤其为氟化物、氯化物、硫酸甲酯、甲酸盐或醋酸盐。
牙齿在本发明书内代表天然或人造牙齿。
牙齿具有各种牙齿术语的含义。
在本说明书中,荧光增白剂包括现有技术中已知的所有荧光增白剂。本发明中给出的荧光增白剂的限定和优先选择对于包含荧光增白剂的组合物以及它们的用途是相同的。
根据本发明使用的荧光增白剂表现出显著的抗微生物效果,尤其是抗病原革兰阳性和革兰阴性细菌以及抗皮肤菌丛细菌。因此它们尤其适合于消毒、除臭、以及皮肤和粘膜还有皮肤附属物(头发)的一般抗微生物处理,特别适合于手和伤口消毒。因此它们适合作为身体护理组合物中的抗微生物活性物质和防腐剂,身体护理组合物如洗发剂、牙膏、沐浴产品、头发护理组合物、液体和固体皂(基于合成表面活性剂和饱和和/或不饱和脂肪酸的盐)、洗液和面霜、除臭剂、含水或含醇溶液,例如皮肤清洁液、湿清洁擦、油或粉末。
因此,本发明还提供身体护理组合物,其包括式(1)的至少一种化合物和化妆用载体或助剂。
根据本发明的身体护理组合物包括基于组合物总重量0.01-15wt%、优选0.1-10wt%的荧光增白剂和化妆用助剂。
根据本发明的牙膏包括基于组合物总重量0.01-15wt%、优选0.1-10wt%的荧光增白剂和化妆用助剂。
根据身体护理组合物存在的形式以及荧光增白剂,该组合物还包括其他组分,例如多价螯合剂(sequestering agent)、染料、芳香油、增稠剂或沉降剂(稠度调节剂)、润肤剂、UV吸收剂、皮肤保护剂、抗氧化剂、提高机械性能的添加剂如二羧酸和/或C14-C22脂肪酸的Al、Zn、Ca、Mg盐,还任选地包含防腐剂。
根据本发明的身体护理组合物可被配制成油包水乳液或水包油乳液、醇类或含醇制剂、离子或非离子两性脂类的泡状分散体、凝胶、固体条或气溶胶制剂。
作为油包水或水包油乳液,化妆用助剂优选包括5-50%的油相、5-20%的乳化剂和30-90%的水。油相可包括适合于化妆品制剂的任何油,如烃油、蜡、天然油、硅酮油、脂肪酸酯或脂肪醇中的一种或多种。优选的一元或多元醇为乙醇、异丙醇、丙二醇、己二醇、甘油和山梨糖醇。
根据本发明的化妆品制剂可在各种领域中使用,尤其考虑例如下面的组合物:
-护肤组合物,如条皂或液体皂形式的皮肤洗涤和清洁组合物、合成洗涤剂或洗涤膏(washing paste),
-沐浴制剂,如液体沐浴制剂(泡沫浴、乳液、淋浴制剂)或固体沐浴制剂,如浴块或浴盐;
-护肤组合物,如皮肤乳液、多重乳液或美肤油(skin oil);
-美容用身体护理组合物,如日霜或粉霜(power cream)、扑面粉(散粉和粉饼)、胭脂或面霜形式的面部化妆品,眼睛护理组合物,如眼影膏制剂、睫毛膏、眼线膏、眼霜或定眼霜(eye-fix cream);嘴唇护理组合物,如口红、润唇膏(lip gloss)、唇线笔,指甲护理组合物,如指甲油、指甲油去除剂、指甲硬化剂或角质层去除剂(cuticle remover);
-私密护理组合物,如私密冲洗洗液或私密喷洒液;
-足护理组合物,如足浴、足粉、足霜或足用香脂(foot balsam),尤其是除臭剂和止汗剂或去硬皮组合物;
-防晒剂,如防晒乳、防晒液、防晒膏、防晒油、防晒霜(sunblock)或热带粉(tropical)、预晒黑制剂或晒后制剂;
-皮肤晒黑制剂,如自晒黑霜;
-褪色(depigmentation)组合物,如皮肤漂白制剂或皮肤光亮组合物;
-驱虫组合物(“驱虫剂(repellant)”),如杀虫油、洗剂、喷雾剂或粘剂(sticks);
-除臭剂,如除臭喷雾剂、泵送喷雾剂、除臭凝胶、条或或走珠(roll-ons);
-止汗剂,如止汗棒、霜或走珠;
-用于清洗和护理弄脏皮肤的组合物,如合成洗涤剂(固体或液体)、剥离或擦制剂或剥离掩膜;
-化学形式的脱发组合物(除毛剂),如脱毛粉、液体脱毛剂、霜或膏状脱毛剂、凝胶形式或气溶胶泡沫的脱毛剂;
-剃须组合物,如剃须皂、发泡剃须膏、不发泡剃须膏、泡沫和凝胶、用于干剃须的剃前制剂、须后水或须后洗剂;
-香味剂,如花露水((科隆香水(eau de Cologne)、化妆水(eau de toilette)、香味香料(eau de parfum)、化妆香味(parfum de toilette)、香料))、芳香油或芳香膏;
-用于牙齿护理、假牙护理和口腔护理的组合物,如牙膏、凝胶牙膏、牙粉、嗽口水浓缩物、防斑嗽口水、修复清洁剂或修复粘合剂;
-用于头发处理的化妆品组合物,如洗发剂形式的头发清洗剂、头发调理剂(hair conditioner),头发护理组合物,如预处理组合物、生发油(hairtonics)、定型膏、定型胶、润发油(pomade)、发用漂洗剂、处理包、深入型头发处理剂,用于头发成形的组合物,如用于烫发(热烫、温烫、冷烫)的卷发剂(waving agent)、头发柔顺制剂、液体头发定型组合物、头发起泡液(hairfoam)、喷发胶(hair sprays)、漂金发剂(blonding agent)如过氧化氢溶液、光亮洗发液、漂金发膏(blonding cream)、漂金发粉(blonding agent)、漂金发糊或油,临时、半永久性或永久性头发着色剂,包含自氧化染料、或天然头发着色剂如指甲花染料或甘菊的制剂。
抗微生物增白皂具有例如以下组成:
0.01-5wt% 式(1)的化合物,
0.3-1wt% 二氧化钛,
1-10wt% 硬脂酸
达到100% 皂基成分,如牛油脂肪酸和椰油脂肪酸的钠盐或甘油。
洗发剂具有例如以下组成:
0.01-5wt% 式(1)的化合物,
12.0wt% 月桂醇聚氧乙烯醚-2-硫酸钠(sodium laureth-2 sulphate)
4.0wt% 椰油酰氨丙基甜菜碱,
3.0wt% NaCl和
加至100% 水。
除臭剂具有例如以下组成:
0.01-5wt% 式(1)的化合物,
60wt% 乙醇,
0.3wt% 芳香油,和
达到100% 水。
本发明还提供包括基于组合物总重量的0.01-15wt%的式(1)的化合物和口服用助剂的口服组合物。
口服组合物的例子:
10wt% 山梨糖醇,
10wt% 甘油,
15wt% 乙醇,
15wt% 丙二醇,
0.5wt% 月桂基硫酸钠,
0.25wt% sodium methyl cocyltaurate,
0.25wt% 聚氧丙烯/聚氧乙烯嵌段共聚物,
0.10wt% 薄荷调味剂,
0.1-0.5wt% 式(1)的化合物,和
48.6wt% 水。
根据本发明的口服组合物可为例如凝胶、糊、膏或含水制剂(漱口水)的形式。
另外,根据本发明的口服组合物可包括释放氟化物离子的化合物,其能有效防止龋齿的形成,例如无机氟化物盐,如氟化钠、氟化钾、氟化铵或氟化钙,或有机氟化物盐,如已知商标名为Olafluor的氟化胺。
另外,根据本发明使用的具有式(1)的苄醇衍生物适用于织物纤维材料的处理,尤其是防腐。纤维材料未被染色和被染色或印刷,并由例如蚕丝、羊毛、聚酰胺或聚氨酯制成,尤其是所有类型的纤维素纤维材料。这种纤维材料为例如天然纤维素纤维,如棉、亚麻、黄麻和大麻,以及再生纤维素。优选的合适织物纤维材料由棉制成。
荧光增白剂还适用于塑料的处理,尤其是抗微生物整理(finishing)或防腐,塑料如聚乙烯、聚丙烯、聚氨酯、聚酯、聚酰胺、聚碳酸酯、胶乳等。这些应用领域为例如地板包覆层(floor covering)、塑料涂层、塑料容器和包装材料;厨房和浴室器具(例如刷子、淋浴帘;海绵、浴室垫)、胶乳、过滤器材料(空气和水过滤器)、医疗部门中使用的塑料制品如绷带材料、注射器、导管等,通常所说的医疗设备、手套和床垫。
纸,例如卫生纸也可用根据本发明的苄醇进行抗微生物整理。
另外,无纺布如尿布、卫生巾、裤衬里、用于卫生和家用的抹布可根据本发明进行抗微生物整理。
另外,荧光增白剂用于洗涤和清洁制剂中,如用于液体和粉末清洁剂或织物柔软剂中。
特别是,荧光增白剂还可用在家庭和各种清洁剂中以清洁、增白和消毒硬质表面。清洁剂具有例如以下组成:
0.01-5% 式(1)的化合物
3.0% 辛醇4EO
1.3% 脂肪醇C8-C10聚葡糖苷
3.0% 异丙醇
加至100% 水。
还有化妆品和家用产品的防腐和增白,技术产品的增白、防腐和抗微生物整理以及用作工艺过程中的杀菌剂也是可以的,如在纸的处理中,尤其在纸处理液、由淀粉或纤维素变体(modification)制成的印刷增稠剂、表面涂层和涂料中。
荧光增白剂还适用于木材的抗微生物处理以及皮革的抗微生物处理、防腐和精整。
另外,根据本发明的化合物适合于防止化妆品和家用产品受到微生物腐烂。
可根据本发明使用的荧光增白剂为已知的化合物。
实施例1:
用荧光增白剂处理羟基磷灰石
溶液A:0.5wt%式(26)的化合物溶解在100g无水乙醇中。
溶液B:0.1gwt%式(26)的化合物溶解在100g无水乙醇中。
溶液C:0.01wt%式(26)的化合物溶解在100g无水乙醇中。
过程a):
将羟基磷灰石基材(大小3/8“×0.06“,供应商Clarkson Chemical Co.,USA)放在溶液A(如上面所给出的),保持5分钟。然后从溶液中取出羟基磷灰石基材,摇晃以除去残留的溶液,然后在室温下干燥2小时。为了分析,然后用蒸馏水洗涤羟基磷灰石基材,并在室温下在空气中干燥18小时。
过程b):
重复过程a),条件是用溶液B替换溶液A。
过程c):
重复过程a),条件是用溶液C替换溶液A。
实施例2:实施例1经处理的羟基磷灰石基材上的荧光定性检验
用UV-光(254nm)测定根据实施例1制备的羟基磷灰石的荧光。在基材上存在可见的荧光。荧光的强度与溶液A、B或C所用的浓度成比例。荧光增白剂对羟基磷灰石基材具有亲合力,因为尽管基材被洗涤,但荧光仍然可见。
实施例3:实施例1经处理的羟基磷灰石的白度(按照Ganz)
为了评价白度,测定处理的羟基磷灰石的白度,然后与未处理的羟基磷灰石基材的白度比较。存在明显的可见增白,其与溶液A、B或C的所用浓度成比例。
所用溶液A,B或C | 无 | 溶液C | 溶液B | 溶液A |
白度 | 82.3 | 87.1 | 91.2 | 96.6 |
实施例4
琼脂结合试验中最小抑制浓度(MIC值)的测定
试验原理:
在合适的溶剂中制备物质的1%储备溶液,以1∶2连续稀释(在琼脂中得到500-1,9ppm的最终浓度)。使每个稀释步骤中的0.3ml溶液与15ml营养培养基混合,而后者仍是液体。在营养培养基固化后,将10μl在0.85%NaCl溶液中的每种试验菌株点到琼脂培养基上。
在37℃下培育培养皿24小时,然后测定不能再观察到生长时的试验物质的最高稀释(最低浓度)。
营养培养基:Mueller Hinton琼脂(Difco)
*Sabouraud 4%葡萄琼脂(Merck)
稀释液: 无菌0.85%(w/w)NaCl溶液
培育 在37℃下24小时
*在29℃下2-3天
试验有机体:
金黄色葡萄球菌(Staphylococcus aureus)ATCC 6583
表皮葡萄球菌(Staphylococcus epidermidis)ATCC 12228
干燥棒状杆菌(Corynebacterium xerosis)ATCC 373
短小棒状杆菌(Propionibacterium acnes)ATCC
大肠杆菌(Escherichia coli)ATCC 10536
猪霍乱沙门(氏)菌(Salmonella choleraesuis)ATCC
肺炎杆菌(Klebsiella pneumoniae)ATCC
*白色念珠菌(Candida albicans)ATCC 10231
*黑曲霉素(Aspergillus niger)ATCC 6275
表1:双苯乙烯基苯的MIC-值[ppm]
具有下式的双苯乙烯基苯 | 金黄色葡萄球菌 | 干燥棒状杆菌 | 棒状杆菌minutissimum | 干燥棒状杆菌 |
23 | 7.8 | 7.8 | 3.9 | 15.6 |
24 | 7.5 | 3.8 | 3.8 | 7.5 |
25 | 62.5 | 15.6 | 15.6 | 62.5 |
26 | 6.3 | 3.1 | 6.3 | 6.3 |
27 | 12.5 | 3.1 | 3.1 | 12.5 |
28 | 6.3 | 6.3 | 3.1 | 6.3 |
29 | 3.1 | 3.1 | 6.3 | 3.1 |
30 | 12.5 | 3.1 | 3.1 | 12.5 |
31 | 62.5 | 125 | 15.6 | 125 |
32 | 0 | 100 | 200 | 50 |
33 | 3.9 | 31.3 | 7.8 | 3.9 |
34 | 3.1 | 3.1 | 3.1 | 3.1 |
表1(续):双苯乙烯基苯的MIC-值[ppm]
具有下式的双苯乙烯基苯 | 短小棒状杆菌 | 大肠杆菌 | 猪霍乱沙门(氏)菌 | 肺炎杆菌 |
23 | 3.9 | 125 | 125 | 31.3 |
24 | 3.8 | 0 | 0 | 120 |
25 | 62.5 | 125 | 125 | 0 |
26 | 12.5 | 200 | 200 | 25 |
具有下式的双苯乙烯基苯 | 短小棒状杆菌 | 大肠杆菌 | 猪霍乱沙门(氏)菌 | 肺炎杆菌 |
27 | 6.3 | 0 | 200 | 25 |
28 | 3.1 | 0 | 0 | 0 |
29 | 3.1 | 200 | 200 | 25 |
30 | 6.3 | 0 | 200 | 25 |
31 | 7.8 | 0 | 0 | 0 |
32 | 100 | 0 | 0 | 0 |
33 | 3.9 | 0 | 0 | 0 |
34 | 1.6 | 50 | 0 | 0 |
实施例5
通过液体培养基(broth)稀释测定对不同口腔微生物的最小抑制浓度(MIC值)
试验原理:
在乙醇中制备物质的1500ppm储备溶液,并移液到生长培养基中得到介于0.94和15ppm之间的浓度。用棉签从血液琼脂培养皿中取出细菌,并在合适的生长培养基中调整产生相当于McFarland 0.5的光密度。在F.nucleatum和P.nigrescens的情况下直接使用这种悬浮液。对于其它菌株,将悬浮液稀释成1∶20。向2ml物质溶液中加入0.1ml这些细菌悬浮液。在培育时间后,评价管的生长(浊度)。
营养培养基:含氯化血红素(hemine)和甲萘醌的巯基乙酸盐培养基
具有氯化血红素和甲萘醌的Columbia培养基,用于P.gingivalis和P.nigrescens
稀释液: 向生长培养基中直接加入相应数量的储备溶液
培育: 在37℃无氧7-10天
*对于链球菌属和A.actinomycetemcomintans,用10%CO2有氧,24小时
试验有机体:
*放线杆菌(Actinobacillus actinomycetemcomitans)ATCC 43718
*链球菌(Streptococcus gordonii)ATCC 10558
*变形链球菌(Streptococcus mutans)ATCC 33402
粘性放线菌(Actinomyces viscosus)ATCC 43146
核粒梭杆菌亚种(Fusobacterium nucleatum subsp.Polymorphum)ATCC10953
甲基丝裂霉素Porphyromonas gingivalis ATCC 33277
Prevotella nigrescens ATCC 33563
表2:双苯乙烯基苯的MIC值[ppm]
具有下式的苯乙烯基苯 | 粘性放线菌 | Streptococcusgordonii | Streptococcusmutans | Actinobacillusactmomycetem-comitans |
23 | 3.75 | 7.5 | 7.5 | 0 |
24 | 3.75 | 7.5 | 7.5 | 15 |
25 | 15 | 0 | 0 | 0 |
26 | 3.8 | 7.5 | 3.8 | 15 |
27 | 7.5 | 15 | 15 | 0 |
28 | 3.8 | 7.5 | 7.5 | 0 |
29 | 3.8 | 7.5 | 3.8 | 7.5 |
30 | 3.8 | 15 | 7.5 | 15 |
31 | 3.8 | 11.25 | 7.5 | 0 |
32 | 0 | 0 | 0 | 0 |
33 | 3.8 | 3.75 | 1.88 | 0 |
34 | 1.9 | 15 | 1.9 | 0 |
表2(续):双苯乙烯基苯的MIC值[ppm]
具有下式的苯乙烯基苯 | Fusobacteriumnucleatum subsp.polymorphum | Porphyromnasgingivalis | Prevotellanigrescens |
23 | 7.5 | 3.75 | 7.5 |
24 | 15 | 1.9 | 1.9 |
25 | 0 | 0 | 15 |
26 | 3.8 | 3.8 | 1.9 |
27 | 7.5 | 7.5 | 3.8 |
28 | 15 | 1.9 | 3.8 |
29 | 3.8 | 1.9 | 1.9 |
30 | 3.8 | 3.8 | 3.8 |
31 | 15 | 1.9 | 3.75 |
32 | 0 | 0 | 0 |
33 | 0 | 15 | 3.75 |
34 | 0 | 7.5 | 3.8 |
实施例6
杀菌剂活性测定
试验原理:
将1g具有适宜的试验产品浓度的储备溶液与8g水混合,然后用1ml选择的试验有机体接种。在指定的接触时间后,取等分试样,灭活(inactivate)并稀释。通过培养皿记数测定每ml培育分析物中存活细菌的数目。每次检查由所用的灭活培养基引起的适当灭活。
稀释液:用于微生物的胰胨(trytone)水
(0.1%胰胨(Oxoid),0.85%NaCl,去离子水)
用于试验物质的去离子水
用于检测存活的微生物的灭活培养基
生长培养基:酪蛋白大豆胨琼脂
灭活培养基:胰蛋白酶大豆液体培养基专用
(10%w/w吐温80,3%w/w卵磷脂,0.1%w/w L-组氨酸,0.055%w/w硫代硫酸钠)
试验有机体:金黄色葡萄球菌ATCC 6538
大肠杆菌ATCC 10536
粘性放线菌ATCC 43146
干燥棒状杆菌ATCC 373
试验浓度:120ppm和1200ppm
接触时间:在22℃下5和30分钟
培育时间:在37℃下24小时
表3:苯乙烯基苯的杀菌活性[log减少量]:
具有下式的双苯乙烯基苯 | 金黄色葡萄球菌 | 大肠杆菌 | ||||||
120ppm/5min | 120ppm/30min | 1200ppm/5min | 1200ppm/30min | 120ppm/5min | 120ppm/30min | 1200ppm/5min | 1200ppm/30min | |
23 | 2 | 4 | 3.3 | 5 | ||||
25 | 1 | 1 | 2.9 | 2.8 | 5 | 5 | 5 | 5 |
26 | 0 | 4 | 4.5 | 5 | ||||
29 | 3 | 5 | 5 | 5 |
表3(续):双苯乙烯基苯的杀菌活性[log减少量]
具有下式的双苯乙烯基苯 | 粘性放线菌 | 干燥棒状杆菌 | ||||||
120ppm/5min | 120ppm/30min | 1200ppm/5min | 1200ppm/30min | 120ppm/5min | 120ppm/30min | 1200ppm/5min | 1200ppm/30min | |
23 | 2 | 4 | 5 | 5 | ||||
25 | 2.9 | 2.1 | 4 | 4 | 5 | 5 | 5 | 5 |
26 | 0 | 3.7 | 2.9 | 5 | ||||
29 | 2.5 | 5 | 5 | 5 |
实施例7
对羟基磷灰石的直接性(substantivity)和生长抑制的测定
试验原理:
在搅拌下在人工唾液(German Dental Magazine DZZ 5/2002)中培育羟基磷灰石圆片4小时,在NaCl中冲洗,干燥过夜,然后在试验物质的乙醇溶液中培育。然后将全部处理的圆片放在12孔Nunclon表面滴定培养皿中(每孔一个圆片),并用试验菌株接种Caso液体培养基。在37℃下培育滴定培养皿,在6和24小时后取样品,通过培养皿记数测定菌落记数。
稀释液:0.85%(w/w)NaCl
用于试验物质的乙醇
培养基:酪蛋白大豆胨琼脂
试验有机体:粘性放线菌ATCC 43146
试验浓度:500ppm
接触时间:在37℃下6和24小时
培育时间:在37℃下24-28小时
示图显示了在羟基磷灰石圆片上吸附物质后式(24)和(33)的双苯乙烯基苯对粘性放线菌的生长抑制,与未处理的对照相比,所述羟基磷灰石圆片用人工唾液进行预处理。
Claims (20)
1.荧光增白剂用于表面抗微生物处理的应用。
2.根据权利要求1的荧光增白剂的应用,用于表面的增白和抗微生物处理。
3.根据权利要求2的荧光增白剂的应用,用于牙齿增白和抗微生物处理用的增白剂。
4.根据前述权利要求任何一项的应用,其中荧光增白剂为双-三嗪基-二氨基均二苯代乙烯、2-(均二苯代乙烯-4-基)-萘并三唑、2-(4-苯基均二苯代乙烯-4-基)苯并噁唑、双(唑-2-基)均二苯代乙烯、1,4-双(苯乙烯基)苯、4,4’-双(苯乙烯基)联苯、1,3-二苯基-2-吡唑啉、双(苯并噁唑-2-基)、双(苯并咪唑-2-基)、2-(苯并呋喃-2-基)-苯并咪唑、香豆素、喹诺酮、萘二甲酰亚胺、季铵化吡啶并三唑、芘衍生物或酰氨基3,7-二氨基-二苯并噻吩-2,8-二磺酸5,5-二氧化物。
5.根据前述权利要求任何一项的应用,其中荧光增白剂为具有式(1)-(20)的化合物:
具有式(1)的双-三嗪基-二氨基均二苯代乙烯
其中
R1、R2、R3和R4彼此独立地为NR5R6、OR7或杂环;
其中
R5和R6彼此独立地为氢;取代或未取代的C6-C10芳基、C1-C10烷基、N,N’-二C1-C6烷基氨基C1-C10烷基或杂环,和
R7为取代或未取代的C6-C10芳基、C1-C10烷基;
或
具有式(2)的2-(均二苯代乙烯-4-基)-萘并三唑
其中
R8和R9彼此独立地为氢、SO3H、CN、卤素;
或
具有式(3)的2-(4-苯基均二苯代乙烯-4-基)苯并噁唑
或
具有式(4)的双(唑-2-基)均二苯代乙烯
或
具有式(5)的1,4-双(苯乙烯基)苯
或
具有式(6)的4,4-双(苯乙烯基)联苯
或
具有式(7)的1,3-二苯基-2-吡唑啉
R10为SO3H、SO2NR11R12,
其中
R11和R12彼此独立地为氢、(C1-C6)烷基-N+(C1-C6)烷基、(C1-C6)烷基-SO3H;
或
具有式(8)的双-苯并噁唑
其中
R13和R14彼此独立地为氢;取代或未取代的C6-C10芳基、C1-C10烷基、1,2-二苯基乙烯基、COO-C1-C10烷基或SO2-C1-C10烷基,和
R为-C=C-、1,2-二苯基亚乙烯基、1,4-亚萘基或2,5-硫代亚苯基,
或
具有式(9)的双(苯并咪唑-2-基)
其中
R15和R16彼此独立地为氢、取代或未取代的C1-C16烷基或苯基;和
或
具有式(10)的2-(苯并呋喃-2-基)-苯并咪唑
或
香豆素,包括3-苯基-7-氨基香豆素、3-苯基-7-(唑-2-基)香豆素、3,7-双(吡咯基)-香豆素和具有式(11)、(12)、(13)或(14)的化合物
其中
R17和R18彼此独立地为氢或取代或未取代的C1-C6烷基,
其中
R19和R20彼此独立地为NR21R22、OR23或杂环,
其中
R21和R22彼此独立地为氢;取代或未取代的C6-C10芳基、C1-C10烷基,和
R23为取代或未取代的C6-C10芳基、C1-C10烷基;
或
具有式(15)的喹诺酮
或
具有式(16)的萘二甲酰亚胺
其中
R24为氢或取代或未取代的C1-C16烷基或苯基,和
其中
R25为氢或取代或未取代的NR26R27、OR28或杂环
其中
R26、R27和R28具有与上面给出的R21、R22和R23相同的定义;或季铵化吡啶并三唑;
或
具有式(17)的芘
或
具有式(18)的酰氨基3,7-二氨基-二苯并噻吩-2,8-二磺酸5,5-二氧化物
其中
R26和R27彼此独立地为取代或未取代的CO-烷氧基苯甲酰、CO-(C1-C6)烷基、CO-苯基,
或
具有式(19)的双苯乙烯基苯
或
具有式(20)的双苯乙烯基联苯
其中
X和X′彼此独立地为-COO-或-CON(R31)、直接键、氧、硫、-O-C1-C3亚烷基-CON(R31)-、-SO2N(R31)-、-O-C1-C3-亚烷基-COO-或-OCO-,
Y和Y′彼此独立地为直接键、C1-C20亚烷基、直接键,
Z为吡啶、2-吡啶-N-甲基、4-吡啶-N-甲基或N(R28R29(R30)q),和
Z′为吡啶、2-吡啶-N-甲基、4-吡啶-N-甲基或N(R28’R29’(R30)q’),
其中
R28和R28’彼此独立地为未取代或取代的C1-C8-烷基或C3-C4烯基,或R28与R29一起,或R28’与R29’一起,为杂环,R29和R29’彼此独立地为未取代或取代的C1-C8烷基或C3-C4烯基,或R29与R28一起或R29’与R28’一起为杂环,或R28和R29,或R28’和R29’与R30一起为吡啶或甲基吡啶环,R30为氢、未取代或取代的C1-C4烷基或C3-C4烯基,或与R28和R29一起或与R28’和R29’一起为吡啶或甲基吡啶环,R30为氢或未取代或取代的C1-C6-烷基,
A-为无色阴离子,和
n和n′彼此独立地为数0或1,和
m和m′彼此独立地为数0或1,和
p和p′彼此独立地为数0、1、2或3,和
q和q′彼此独立地为数0或1,和
苯核B和C还可被非发色取代基取代;
6.根据前述权利要求任何一项的应用,其中荧光增白剂为
具有式(21)的双苯乙烯基苯
或
具有式(22)的双苯乙烯基联苯
其中
X1和X1′为-COO-或-CONH-、直接键、氧、硫、-OC1-C3亚烷基-CONH-、-SO2NH-、-O-C1-C3亚烷基-COO-或-OCO-,
Y1和Y1′彼此独立地为直接键、C1-C4亚烷基或羟基亚丙基,
Z1和Z1′彼此独立地为吡啶、2-吡啶-N-甲基、4-吡啶-N-甲基或N(R35R36(R37)q”),
其中
R35和R36彼此独立地为C1-C4烷基或在一起为吡咯烷、哌啶、六亚甲基亚胺或吗啉环,或与R37一起为吡啶或甲基吡啶环,
R30为氢、C1-C4烷基、C3-C4烯基、C1-C3烷氧基羰基甲基、苄基、C2-C4-羟基烷基或C2-C4氰基烷基或与R35和R36一起为吡啶或甲基吡啶环,
R32为氢、氯、C1-C4烷基、C3-C4烯基、C1-C3烷氧基或(X1)m-Y1-N(R35R36(R37)q”),或与R33一起为三亚甲基或四亚甲基,
R33为氢、氯、C1-C4烷基或C1-C3烷氧基,或与R32一起为三亚甲基或四亚甲基,
R34为氢、氯或甲基,
n1和n1′彼此独立地为数0或1,
m1和m1′彼此独立地为数0或1,和
p1和p1′彼此独立地为数0、1、2或3,和
q′’为数0或1,和
A-为无色阴离子。
8.根据前述权利要求任何一项的应用,是用于牙齿护理产品、假牙护理产品和口腔护理产品的增白和抗微生物处理。
9.根据权利要求8的应用,其中荧光增白利用于牙膏、凝胶牙膏、牙粉、嗽口水浓缩物、防斑嗽口水、修复清洁剂或修复粘合剂。
10.根据前述权利要求任何一项的应用,是用于皮肤、粘膜和头发的抗微生物处理、除臭、消毒和/或增白。
11.根据前述权利要求任何一项的应用,是用于消毒和除臭。
12.根据前述权利要求任何一项的应用,是用于织物纤维材料的抗微生物处理和增白。
13.根据前述权利要求任何一项的应用,是用于防腐和/或增白。
14.根据前述权利要求任何一项的应用,是用于在洗涤和清洁制剂中的抗微生物处理和增白。
15.根据前述权利要求任何一项的应用,是用于塑料、纸、无纺布、木材或皮革的增白和抗微生物整理和防腐。
16.根据前述权利要求任何一项的应用,是用于技术产品、尤其是淀粉或纤维素变体制成的印刷增稠剂、表面涂层和涂料的增白和抗微生物整理和防腐。
17.根据前述权利要求任何一项的荧光增白剂的应用,是在工艺过程中作为杀菌剂。
18.一种身体护理组合物,包括基于组合物总重量0.01-15wt%的荧光增白剂和化妆用助剂。
19.一种口腔组合物,包括基于组合物总重量0.01-15wt%的荧光增白剂和口腔用助剂。
20.牙膏,包括基于组合物总重量0.01-15wt%的荧光增白剂和口腔用助剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP04103830 | 2004-08-09 | ||
EP04103830.8 | 2004-08-09 |
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CN101035508A true CN101035508A (zh) | 2007-09-12 |
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CNA2005800343852A Pending CN101035508A (zh) | 2004-08-09 | 2005-08-03 | 荧光增白剂作为抗微生物剂的应用 |
Country Status (4)
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US (1) | US20070258912A1 (zh) |
EP (1) | EP1776086A2 (zh) |
CN (1) | CN101035508A (zh) |
WO (1) | WO2006015959A2 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101851210A (zh) * | 2010-05-26 | 2010-10-06 | 南京工业大学 | 三联苯桥联双苯并咪唑季铵盐类化合物、合成方法及应用 |
CN107523192A (zh) * | 2017-09-27 | 2017-12-29 | 江苏固格澜栅防护设施有限公司 | 一种酸碱刺激双响应智能防腐涂层的制备方法及应用 |
CN114010790A (zh) * | 2021-11-15 | 2022-02-08 | 重庆理工大学 | 荧光增白剂在抗真菌感染中的应用 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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BRPI0707719A2 (pt) | 2006-02-10 | 2011-05-10 | Summit Corp Plc | uso de um composto ou de um sal farmaceuticamente aceitÁvel do mesmo |
CA2685540C (en) | 2007-08-03 | 2018-10-16 | Graham Michael Wynne | Drug combinations for the treatment of duchenne muscular dystrophy |
CN102964864B (zh) * | 2012-11-28 | 2013-12-25 | 华南师范大学 | 一种多功能呋喃酮荧光增白剂及其制备方法 |
FR3017376B1 (fr) * | 2014-02-12 | 2016-02-12 | Albea Le Treport | Recipient comprenant un reservoir et un systeme de distribution de produit |
WO2019183381A2 (en) * | 2018-03-23 | 2019-09-26 | The Regents Of The University Of California | Short conjugated oligoelectrolytes and uses thereof |
Family Cites Families (9)
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CA1172980A (en) * | 1979-04-02 | 1984-08-21 | Kenji Takemoto | Pentadecapeptide and process for the preparation thereof |
US4314820A (en) * | 1979-04-11 | 1982-02-09 | Ciba-Geigy Corporation | Distyrylbenzene fluorescent brightening agents |
US4384121A (en) * | 1979-11-01 | 1983-05-17 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US4608088A (en) * | 1984-03-22 | 1986-08-26 | Dento-Med Industries Incorporated | Denture adherent powder |
CN1297347A (zh) * | 1998-02-19 | 2001-05-30 | 奥拉修蒂科有限公司 | 抗菌托牙粘合剂组合物 |
US6540792B1 (en) * | 1999-04-14 | 2003-04-01 | Toray Industries, Inc. | Cellulose fiber-containing structure |
US7306809B2 (en) * | 2002-09-13 | 2007-12-11 | Lipo Chemicals, Inc. | Optically activated particles for use in cosmetic compositions |
GB0222091D0 (en) * | 2002-09-24 | 2002-10-30 | Boots Co Plc | Dental compositions and methods |
CN100471940C (zh) * | 2003-11-12 | 2009-03-25 | 西巴特殊化学制品控股公司 | 表面增亮组合物 |
-
2005
- 2005-08-03 CN CNA2005800343852A patent/CN101035508A/zh active Pending
- 2005-08-03 US US11/659,549 patent/US20070258912A1/en not_active Abandoned
- 2005-08-03 WO PCT/EP2005/053780 patent/WO2006015959A2/en active Application Filing
- 2005-08-03 EP EP05771988A patent/EP1776086A2/en not_active Withdrawn
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101851210A (zh) * | 2010-05-26 | 2010-10-06 | 南京工业大学 | 三联苯桥联双苯并咪唑季铵盐类化合物、合成方法及应用 |
CN107523192A (zh) * | 2017-09-27 | 2017-12-29 | 江苏固格澜栅防护设施有限公司 | 一种酸碱刺激双响应智能防腐涂层的制备方法及应用 |
CN114010790A (zh) * | 2021-11-15 | 2022-02-08 | 重庆理工大学 | 荧光增白剂在抗真菌感染中的应用 |
Also Published As
Publication number | Publication date |
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US20070258912A1 (en) | 2007-11-08 |
WO2006015959A3 (en) | 2006-05-04 |
WO2006015959A2 (en) | 2006-02-16 |
EP1776086A2 (en) | 2007-04-25 |
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