CN1315851A - 口腔护理组合物 - Google Patents
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Abstract
本发明涉及含去斑剂的口腔护理组合物。所述去斑剂是二价铜、锌、铁或锡,或者三价铁与特定类型的环α-羟基酮的络合物,典型例是铜(Ⅱ)-乙基麦芽酚络合物。这些络合物比铜-日柏酚络合物等有更强去斑作用。
Description
本发明涉及含有特定去斑剂的口腔护理组合物。更具体地说,涉及含带有生物活性配体的某些酮、锌、铁或锡金属络合物作为去斑剂的口腔护理组合物。
人们知道,含某些生物活性配体的铜和锌金属络合物有杀微生物活性。例如EP-A-0728478(Otsuta药物有限公司)介绍了铜-日柏酚和锌-日柏酚络合物,申称其有杀微生物活性。根据该文献,这些铜-和锌-日柏酚络合物可用于口腔护理组合物中。
日柏酚是4-异丙基环庚三烯酚酮、即环α-羟基酮,结构式如下:
现我们发现不同类型的环α-羟基酮也是生物活性配体,能与铜、锌、铁和锡形成络合物。该络合物有去斑活性,优于前述铜-和锌-日柏酚络合物。
其中X代表O或NR3,R1和R3代表H或C1-C16,优选C1-C4支链或直链烷基,而R2代表H或羟甲基。环中第2位和第3位碳原子之间的键可以是饱和的或不饱和的,优选不饱和的。
因此该类环α-羟基酮包括羟基吡喃-4-酮和羟基吡啶-4-酮衍生物。该类环α-羟基酮的典型例是麦芽酚(即3-羟基-2-甲基-4H-吡喃-4-酮),其中X是O,R1是甲基、而R2是氢;乙基麦芽酚(即3-羟基-2-乙基-4H-吡喃-4-酮),其中X是O,R1是乙基,而R2是H;曲酸(5-羟基-2-羟甲基-4H-吡喃-4-酮),其中X是O,R1是H,而R2是羟甲基;2-甲基-3-羟基吡啶-4-酮,其中X=NR3,R3=H,R1=甲基,而R2=H;1,2-二甲基-3-羟基吡啶-4-酮,其中X=NR3,R3=甲基,R1=甲基,而R2=H;以及1-乙基-2-甲基-3-羟基吡啶-4-酮,其中X=NR3,R3=乙基,R1=甲基,而R2=H。
与上述环α-羟基酮络合的金属是二价铜、锌、铁和锡、以及三价铁。
本发明的环α-羟基酮及其金属络合物是已知的,并可由已确定的方法合成,例如由Berg等人在“晶体学报”,B32,(1976),第3121页上;由Annan等人在“加拿大化学杂志”,68,(1990),第1598页上;由Denekamp等人在“Dalton论文集”,(1992),第2375页上;由E1-Jammal等人在“医药化学杂志”,37,(1994),第461页上;以及Ellis等人在“医药化学杂志”,39,(1996),第3659页上所述。适宜的络合物可由二价铜、锌、铁或锡盐、或者三价铁盐与环-α-羟基酮,按摩尔比10∶1至1∶10,优选4∶1至1∶4,更优选2∶1至1∶2(该摩尔比以金属离子为基础计)形成。
根据本发明优选的金属络合物是Cu2+和Sn2+络合物,尤其是Cu2+和Sn2+麦芽酚及乙基麦芽酚络合物。
本发明的金属络合物在口腔护理组合物中的含量占组合物重量0.001-5%,优选0.1-3%,以占组合物重量0.2-2%获得最佳效果。各种金属络合物的混合物也可使用。该络合物可在其加入口腔护理组合物之前制备,或者在配制该口腔护理组合物期间原位制备。有时宜以形成络合物所需过量化学当量加入环α-羟基酮,以避免贮存期间该口腔护理组合物中络合物可能出现的分解作用,以及进一步提高该络合物的去斑活性。已发现有时也宜于使用过量的金属盐,例如铜或锡盐,以进一步提高去斑活性。
视需要,本发明口腔护理组合物还可含有常规成分,例如淀粉、糖、水或水/醇体系等可药用载体。也可含有少量表面活性剂,例如阴离子、非离子、阳离子和两性离子、或两性表面活性剂。还可含有颗粒磨料,例如二氧化硅、氧化铝、碳酸钙、磷酸二钙、焦磷酸钙、羟磷灰石、三偏磷酸盐、不溶性六偏磷酸盐等,还包括附聚颗粒磨料,通常占3-60%重量。若以碳酸钙为磨料,则其与除铜盐以外的本发明金属络合物更相容,根据EP-B-38867(Blendax),铜盐与碳酸钙则很不相容。
此外,还可含甘油、山梨醇、丙二醇、木糖醇、乳糖醇等润湿剂。
也可以包含羧甲基纤维素钠、黄原胶、阿拉伯胶等粘结剂和增稠剂,以及合成聚合物,例如聚丙烯酸酯,和Carbopol之类的羧乙烯基聚合物。
也可以含有薄荷油之类的香料,以及防腐剂、遮光剂、着色剂、pH调节剂、甜味剂等。
也可以加入其它杀菌剂,例如三氯生;洗必太;柠檬酸锌、柠檬酸锌钠,焦磷酸锡等铜、锌和锡盐;血根碱提取物;2-甲基-5-硝基-1-咪唑基-乙醇等。杀菌剂其它例子是如鲸蜡基氯化吡啶鎓之类的季铵化合物;二葡糖酸洗必太、海克替啶、奥替尼啶、阿来西啶等双胍类;2,2’-亚甲基-二(4-氯-6-溴苯酚)之类的卤代双酚化合物。
还可以含有提高抗菌剂等活性成分输送能力的聚合物。所述聚合物是与马来酸酐共聚的聚乙烯基甲基醚共聚物和其它可以提高输送能力的类似聚合物,例如DE-A-3942643(Colgate)所述。
虽然本发明络合物具体用作去斑剂,但它们也可用作口腔护理组合物中的杀微生物剂和牙龈消炎剂。
此外,布洛芬、氟比洛芬、阿斯匹林、吲哚美辛等消炎剂也可加入其中。
还可以加入氟化钠和氟化锡、氟化胺、一氟磷酸钠、酪蛋白等抗龋剂;脲、乳酸钙、甘油磷酸钙、聚丙烯酸锶等斑块缓冲剂。其它视需要加入的成分包括维生素,例如维生素C及植物提取物。甘油一油酸酯、柠檬酸钾、氯化钾、酒石酸钾、碳酸氢钾、草酸钾、硝酸钾、以及锶盐等脱敏剂也可加入。
也可以包括缓冲pH值和组合物离子强度的缓冲剂和盐,还可加入脂质体和其它包封剂,用于改善活性成分的输送或稳定性。
此外,该口腔护理组合物还可包括去结石剂,例如碱金属焦磷酸盐、含次磷酸盐的聚合物、有机磷酸盐、磷柠檬酸盐等。
此外,该组合物可以含功能性生物分子,例如杆菌素、抗生素、酶等。
其它视需要加入的成分可以包括漂白剂,例如过氧二磷酸钾等过氧化合物,包括碳酸氢钠/柠檬酸体系等起泡系统,和变色系统等等。
也可以将牙膏配制进双隔间型分配器所用的系统中。
以下述实施例进一步说明本发明。
实施例1
以酮盐、和日柏酚及麦芽酚的铜络合物进行体外生物膜去斑试验。
该试验以监测用牙膏浆液处理后96孔平板各孔中形成的单一细菌种生物膜的生长(测定吸收度)为基础,并计算达到所选择的浊度(即630nm处选择的吸收度值)所需时间。
在BHI培养基中,将S.Warneri培养过夜。将培养物离心处理并用磷酸盐缓冲盐水(PBS)洗涤两次,至其光密度接近1.0。将200μl细菌悬浮液等分样,用吸管加入到以马来酐活化过的聚苯乙烯96孔平板(Pierce-Warriner、Chester)的各孔中。用无菌板状密封器将该平板盖上(为防止污染),离心处理(3000rpm,4分钟),并于37℃保温1小时。若板在制备当天使用,将其置于室温至使用为止,或如果数小时尚不需使用,则置于4℃。用PBS洗涤有生物膜的孔三次,需小心处置,防止细菌破坏分裂。
将牙膏与水混合制备33%(w/w)牙膏浆液、于3500rpm离心10或20分钟(heraeus Labofuge 400或MSE Mistral 1000离心器)。将上清液倾入无菌容器中,并在一天内使用。
将平板洗涤之后,各孔用200μl牙膏上清液处理30秒。将该板倒盖于装有Virkon消毒液的烧杯上,将其在吸收纸上向下轻拍使其干燥,用无菌Milli-Q牌号的溶液洗涤三次,并再在吸收纸上向下轻拍干燥之。
处理及洗涤之后,各孔中相继加入200μl BHI、80μl无菌轻矿物油。于微滴平板读数仪(Dynex Technologies DIAS)中于37℃保温16小时,并于630nm波长下每15分钟监测一次生长情况。A630达到0.4所需时间作为终点。该吸收度近似于各细菌生长曲线的内曲点,该处培养物生长最快。所取最大生长速度点,作为对本底吸收中变量最不敏感的点,而在时间轴上是能最清晰分辨的点。记录下达到0.4光密度的时间,该生长时间越长,则处理越有效。
在含白垩作为磨擦清洁剂的常规牙膏中,得到下述结果:
光密度(O.D.)达 Cu所占重量百分比 麦芽酚所占重量
0.4的时间(小时) (为CuSO4) 百分比
5.32 - -
5.39 0.1 -
5.14 - 0.1
12.29 0.1 0.1
4.15 - 0.2
10.26 0.1 0.2
该结果表明,铜(Ⅱ)-麦芽酚络合物(原位形成,由牙膏颜色变绿可以证明其已形成)的抗菌效果,明显大于CuSO4或麦芽酚各自单独存在的效果,由达到0.4光密度所需时间明显较长可以看出。
用含二氧化硅作为磨擦剂的常规牙膏重复该试验,得到下述结果:
光密度(O.D.)达 Cu所占重量百分比 麦芽酚所占重量
0.4的时间(小时) (为CuSO4) 百分比
4.88 - -
6.20 0.1 -
5.10 - 0.1
13.86 0.1 0.1
4.79 - 0.2
12.92 0.1 0.2
这些结果也清楚表明,铜(Ⅱ)-麦芽酚络合物的抗菌效果好于硫酸铜。
以标准牙膏溶液重复该试验,得到下述结果:
光密度(O.D.)达 Cu所占重量百分比 麦芽酚所占重量
0.4的时间(小时) (为CuSO4) 百分比
4.34 - -
6.49 0.1 -
4.38 - 0.1
9.39 0.1 0.1
4.69 - 0.2
9.57 0.1 0.2
相比之下,0.25%CuSO4和0.25%日柏酚达到0.4 O.D.生长时间要7小时,单独0.25%CuSO4则为4.82小时,而单独0.25%日柏酚为4.54小时。
提高麦芽酚含量,CuSO4为0.1%,以上述标准牙膏溶液试验,得到下面结果:光密度达到0.4的时间 麦芽酚重量百分比4.03 -9.66 0.19.72 0.29.38 0.58.55 1上面所有试验中,硫酸铜(Ⅱ)均为其五水合物盐。当使用麦芽酚和乙基麦芽酚的锌、铁和锡络合物时,获得相似结果。
实施例2制备下述牙膏:
产品成分 | 1.(安慰剂) | 2. | 3. | 4. |
山梨醇(70%) | 45.00 | 45.00 | 45.00 | 45.00 |
糖精钠 | 0.17 | 0.17 | 0.17 | 0.17 |
二氧化钛 | 1.00 | 1.00 | 1.00 | 1.00 |
聚乙二醇1500 | 5.00 | 5.00 | 5.00 | 5.00 |
增稠二氧化硅 | 8.00 | 8.00 | 8.00 | 8.00 |
磨擦二氧化硅 | 10.00 | 10.00 | 10.00 | 10.00 |
纤维素胶 | 0.90 | 0.90 | 0.90 | 0.90 |
月桂基硫酸钠 | 1.50 | 1.50 | 1.50 | 1.50 |
香料 | 1.00 | 1.00 | 1.00 | 1.00 |
硫酸铜五水合物 | - | 0.20 | 0.20 | 0.20 |
日柏酚 | - | - | 0.20 | - |
乙基麦芽酚 | - | - | - | 0.20 |
乙醇 | - | - | - | 1.0 |
水 | TO 100% | TO 100% | TO 100% | TO 100% |
按Harrap在“临床牙周病学杂志”(1)(1974),第166-174页所述方法,进行抑制斑产生试验,测定以上产品的斑抑制作用(PGI),单独刷洗并用产品1作安慰剂,测量试验开始时和18小时之后的斑块。根据下述公式,PGI以百分比表达:
产品 PGI(%) 标准误差 p
2 15.16 11.43 n.s.
3 11.98 12.45 n.s.
4 26.31 10.686 0.026
这些结果表明,比起安慰剂,铜(Ⅱ)乙基麦芽酚络合物的PGI明显较高,而单独用铜,或用铜-日柏酚络合物,则与安慰剂相比PGI没有明显差别。
Claims (6)
1.一种口腔护理组合物,含铜、锌、铁或锡化合物作为去斑剂,其特征在于所述化合物是键合于下述通式的环α-羟基酮生物活性配体的二价铜、锌、铁或锡,或者三价铁的络合物,其中X代表O或NR3,R1和R3代表H或C1-C16支链或直链烷基,而R2代表H或羟甲基,环中第2位和第3位碳原子之间的键可以是饱和的或不饱和的。
2.根据权利要求1的口腔护理组合物,其特征在于所述键是不饱和的。
3.根据权利要求1或2的组合物,其特征在于,其中R1和R3代表H或C1-C4支链或直链烷基。
4.根据权利要求1-3的口腔护理组合物,其特征在于所述络合物是二价铜络合物。
5.根据权利要求1-4的口腔护理组合物,其特征在于环α-羟基酮是乙基麦芽酚。
6.键合于权利要求1通式的环α-羟基酮上的二价铜、锌、铁或锡,或者三价铁的络合物的应用,将其用于制备口腔护理组合物,作为杀微生物剂、去斑剂或牙龈消炎剂。
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Application Number | Priority Date | Filing Date | Title |
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EP98307733 | 1998-09-23 | ||
EP98307733.0 | 1998-09-23 |
Publications (2)
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CN1315851A true CN1315851A (zh) | 2001-10-03 |
CN1178642C CN1178642C (zh) | 2004-12-08 |
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CNB998104639A Expired - Fee Related CN1178642C (zh) | 1998-09-23 | 1999-09-20 | 口腔护理组合物 |
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US (1) | US6287541B1 (zh) |
EP (2) | EP1115373B1 (zh) |
JP (1) | JP2003517442A (zh) |
CN (1) | CN1178642C (zh) |
AT (2) | ATE290848T1 (zh) |
AU (2) | AU742428B2 (zh) |
BR (1) | BR9913890B1 (zh) |
CA (1) | CA2342976A1 (zh) |
DE (2) | DE69924265T2 (zh) |
HU (1) | HUP0103667A3 (zh) |
ID (1) | ID28630A (zh) |
PL (1) | PL194985B1 (zh) |
TR (1) | TR200100846T2 (zh) |
WO (2) | WO2000018366A1 (zh) |
ZA (1) | ZA200101499B (zh) |
Cited By (3)
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CN102028305A (zh) * | 2010-11-24 | 2011-04-27 | 湖南中烟工业有限责任公司 | 一类邻羟基酮类化合物的锌配合物的应用 |
CN110248654A (zh) * | 2017-02-06 | 2019-09-17 | 英国研究与创新署 | 包含铜-羟基吡喃酮络合物的抗微生物组合物 |
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JP2003517442A (ja) * | 1998-09-23 | 2003-05-27 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 口腔手入れ組成物 |
AR020661A1 (es) | 1998-09-30 | 2002-05-22 | Alcon Lab Inc | Una composicion farmaceutica topica oftalmica, otica o nasal y el uso de la misma para la manufactura de un medicamento |
US7632803B2 (en) | 1999-10-01 | 2009-12-15 | Dmi Life Sciences, Inc. | Metal-binding compounds and uses therefor |
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AU2003210850A1 (en) | 2002-02-05 | 2003-09-02 | Bristol-Myers Squibb Company | N-substituted3-hydroxy-4-pyridinones and pharmaceuticals containing thereof |
US6689342B1 (en) | 2002-07-29 | 2004-02-10 | Warner-Lambert Company | Oral care compositions comprising tropolone compounds and essential oils and methods of using the same |
US6787675B2 (en) | 2002-07-29 | 2004-09-07 | Warner-Lambert Company | Substituted tropolone compounds, oral care compositions containing the same and methods of using the same |
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WO2011123121A1 (en) | 2010-03-31 | 2011-10-06 | Colgate-Palmolive Company | Oral care composition |
JP5694506B2 (ja) | 2010-03-31 | 2015-04-01 | コルゲート・パーモリブ・カンパニーColgate−Palmolive Company | 口腔ケア組成物 |
US8952057B2 (en) | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
BR112019025631A2 (pt) | 2017-06-06 | 2020-06-16 | Unilever Nv | Composição de gel aquosa para clarear dentes, kit de peças, dispositivo para clarear dentes, método para clarear dentes, uso de uma composição de gel aquosa e produto embalado |
EP3774944B1 (en) | 2018-06-26 | 2022-04-13 | Unilever Global IP Limited | A novel polymer, a composition, a method and a kit for whitening teeth |
WO2021094156A1 (en) | 2019-11-11 | 2021-05-20 | Unilever Ip Holdings B.V. | A film and a kit for whitening teeth |
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-
1999
- 1999-09-20 JP JP2000573697A patent/JP2003517442A/ja not_active Withdrawn
- 1999-09-20 AT AT99947463T patent/ATE290848T1/de not_active IP Right Cessation
- 1999-09-20 DE DE69924265T patent/DE69924265T2/de not_active Expired - Lifetime
- 1999-09-20 AU AU60895/99A patent/AU742428B2/en not_active Ceased
- 1999-09-20 BR BRPI9913890-5A patent/BR9913890B1/pt not_active IP Right Cessation
- 1999-09-20 WO PCT/EP1999/007379 patent/WO2000018366A1/en active IP Right Grant
- 1999-09-20 HU HU0103667A patent/HUP0103667A3/hu unknown
- 1999-09-20 AT AT99953749T patent/ATE285221T1/de not_active IP Right Cessation
- 1999-09-20 AU AU10334/00A patent/AU1033400A/en not_active Abandoned
- 1999-09-20 EP EP99953749A patent/EP1115373B1/en not_active Expired - Lifetime
- 1999-09-20 ID IDW20010673A patent/ID28630A/id unknown
- 1999-09-20 CA CA002342976A patent/CA2342976A1/en not_active Abandoned
- 1999-09-20 WO PCT/EP1999/007380 patent/WO2000016736A1/en active IP Right Grant
- 1999-09-20 CN CNB998104639A patent/CN1178642C/zh not_active Expired - Fee Related
- 1999-09-20 EP EP99947463A patent/EP1115371B1/en not_active Expired - Lifetime
- 1999-09-20 DE DE69922817T patent/DE69922817T2/de not_active Expired - Lifetime
- 1999-09-20 PL PL346875A patent/PL194985B1/pl not_active IP Right Cessation
- 1999-09-20 TR TR2001/00846T patent/TR200100846T2/xx unknown
- 1999-09-23 US US09/401,880 patent/US6287541B1/en not_active Expired - Fee Related
-
2001
- 2001-02-22 ZA ZA200101499A patent/ZA200101499B/en unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102010790A (zh) * | 2010-11-24 | 2011-04-13 | 湖南中烟工业有限责任公司 | 麦芽酚或乙基麦芽酚的锌配合物的应用 |
CN102028305A (zh) * | 2010-11-24 | 2011-04-27 | 湖南中烟工业有限责任公司 | 一类邻羟基酮类化合物的锌配合物的应用 |
CN102010790B (zh) * | 2010-11-24 | 2012-09-19 | 湖南中烟工业有限责任公司 | 麦芽酚或乙基麦芽酚的锌配合物的应用 |
CN102028305B (zh) * | 2010-11-24 | 2013-11-27 | 湖南中烟工业有限责任公司 | 一类邻羟基酮类化合物的锌配合物的应用 |
CN110248654A (zh) * | 2017-02-06 | 2019-09-17 | 英国研究与创新署 | 包含铜-羟基吡喃酮络合物的抗微生物组合物 |
Also Published As
Publication number | Publication date |
---|---|
DE69924265D1 (de) | 2005-04-21 |
ID28630A (id) | 2001-06-21 |
EP1115373B1 (en) | 2004-12-22 |
BR9913890A (pt) | 2001-07-03 |
JP2003517442A (ja) | 2003-05-27 |
WO2000018366A1 (en) | 2000-04-06 |
ATE290848T1 (de) | 2005-04-15 |
EP1115373A1 (en) | 2001-07-18 |
AU1033400A (en) | 2000-04-17 |
ATE285221T1 (de) | 2005-01-15 |
CA2342976A1 (en) | 2000-03-30 |
ZA200101499B (en) | 2002-02-22 |
DE69924265T2 (de) | 2005-08-25 |
AU6089599A (en) | 2000-04-10 |
DE69922817T2 (de) | 2005-06-16 |
PL346875A1 (en) | 2002-03-11 |
AU742428B2 (en) | 2002-01-03 |
US6287541B1 (en) | 2001-09-11 |
EP1115371A1 (en) | 2001-07-18 |
DE69922817D1 (de) | 2005-01-27 |
BR9913890B1 (pt) | 2010-10-19 |
HUP0103667A2 (hu) | 2002-02-28 |
CN1178642C (zh) | 2004-12-08 |
WO2000016736A1 (en) | 2000-03-30 |
EP1115371B1 (en) | 2005-03-16 |
PL194985B1 (pl) | 2007-07-31 |
TR200100846T2 (tr) | 2002-03-21 |
HUP0103667A3 (en) | 2007-10-29 |
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