CN1678791A - 释放生物活性物质的方法 - Google Patents
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Abstract
本申请涉及含羟基的生物学活性物质在底物上受控释放和/或缓释的方法,其包括使所述含羟基的物质依次与卤素取代的脂肪族酰卤,和包含至少一个叔氨基的二胺或者杂环芳香胺反应,并将这样得到的水溶性酯施用于底物上,最后使酯在底物上水解。
Description
本发明涉及一种在底物上释放含羟基的生物活性物质的方法,和包含有含羟基的生物活性物质、卤素取代的脂肪族酰卤和叔二胺或杂环芳香胺的反应产物的水溶液。
美国专利4,083,847描述了瞬间水溶性(transiently water-soluble)的分散染料,这种分散染料包含有能够在印模条件下脱除的基团,该基团带有至少一种水溶性基团。这样可以避免加入大量的分散剂和稳定剂。
出人意料的是,现在已经发现,通过施用呈水溶液形式的嵌段化合物(blocked compound)并随后在水解条件下脱模(deblocking),这一原理可以用于任何种类的生物活性化合物在各种类型底物上的受控释放。
本发明涉及含羟基的生物活性物质在底物上受控释放的方法,其包括使所述含羟基的物质依次与卤素取代的脂肪族酰卤,和包含至少一个叔氨基的二胺或者杂环芳香胺反应,并将这样得到的水溶性酯施用于底物上,最后使酯在底物上水解。
适当的含羟基的生物活性物质是任何类型的药物,例如止痛药如扑热息痛和乙酰水杨酸,维生素如抗坏血酸,激素如睾丸激素和雌二醇。
植物防护剂如除草剂、杀真菌剂、杀虫剂和杀菌剂也可以用于本发明的方法中。
其他适当的生物活性物质是调味剂(如薄荷醇)和化妆品。
可用于所要求方法中的其他优选的生物活性物质是杀虫剂或抗微生物剂如二氯苯氧氯酚。
所要求方法的第一个步骤是,使含羟基的物质R-OH与卤素取代的脂肪族酰卤反应,形成相应的卤素取代的酸酯。
之后,通过使卤素取代的酯与含至少一个叔氨基的二胺或杂环芳香胺反应而制备水溶性铵盐。
优选的含至少一个叔氨基的二胺是通式R1R2N-A-NR3R4的二胺,其中,R1和R2独立地为C1-C7烷基,R3和R4独立地为H或C1-C7烷基,A是C1-C7直链或支化烷基链。
适当的式R1R2N-A-NR3R4二胺的实例是:
1,2-二(二甲氨基)乙烷,1,3-二(二甲氨基)丙烷,
1,2-二(二甲氨基)丙烷,1,4-二(二甲氨基)丁烷,
1,3-二(二甲氨基)丁烷,2,3-二(二甲氨基)丁烷,
1,5-二(二甲氨基)-2-戊烯,1,5-二(二甲氨基)戊烷,
1,6-二(二甲氨基)己烷,1,7-二(二甲氨基)庚烷,
1,2-二(二乙基氨基)乙烷,1,3-二(二乙基氨基)丙烷,
1,2-二(二乙基氨基)丙烷,1,4-二(二乙基氨基)丁烷,
1,3-二(二乙基氨基)丁烷,2,3-二(二乙基氨基)丁烷,
1,5-二(二乙基氨基)-2-戊烯,1,5-二(二乙基氨基)戊烷,
1,6-二(二乙基氨基)己烷,1,7-二(二乙基氨基)庚烷,
1,4-二(二甲氨基)-1,3-丁二烯和1-二甲氨基-2-甲基辛基氨基-乙烷。
优选的二胺是1,2-二(二甲氨基)乙烷。
可以用于本发明方法中的杂环芳香族胺可以是吡咯类,咪唑类,噁唑类,吡啶类,1,2-、1,3-和1,4-二嗪类,1,2、1,3-和1,4-三嗪类以及苯并吡咯类,苯并咪唑类,喹啉类,异喹啉类和联吡啶类。
上述杂环芳香族胺可以是未取代的或者可以被一个或多个卤素原子、氰基、烷基、烷氧基或二烷基氨基基团取代。
优选,杂环芳香胺是未取代或取代的吡啶、联吡啶、咪唑或噁唑。
特别优选的是吡啶,4-二甲基氨基吡啶,4-甲氧基吡啶,4-氰基吡啶和4,4′-联吡啶。
嵌段化合物在冷水中显示出高溶解度,因此可以以水溶液的形式用于许多底物如木材、塑料、纸张和纺织品上。
优选,本发明的方法用于装饰纸(furnishing paper)或织物上。
适当的底物是,例如下述物质,如聚丙烯腈,丙烯腈与其他乙烯系化合物如丙烯酸酯、丙烯酰胺、乙烯基吡啶、氯乙烯或1,1-二氯乙烯的共聚物,二氰基乙烯与醋酸乙烯酯的共聚物,以及丙烯腈嵌段共聚物,聚氨酯,合成聚酰胺如聚(亚己基己二酸酰胺)或聚酰胺66、聚(ε-己内酰胺)或聚酰胺6、聚(亚己基癸二酸酰胺)或聚酰胺610和聚(11-氨基十一酸)或聚酰胺11,纤维素三醋酸酯和纤维素2.5醋酸酯,聚酯,特别是所有的纤维素基底物如棉和粘胶,以及含纤维素的混合纤维。这些物质可以呈相差很大的加工形式,例如短纤纱,针织物,机织织物,纱或纤维。
本发明的方法操作容易,并且可以通过纺织品印模领域已知的通用方法,例如尽染工艺(exhaust process)或轧染工艺进行。
酯化合物的这一施用工艺通常在提高的温度下,例如在60℃-130℃的温度下,如果适当的话在加压下,在pH值为3-8,优选4-7,特别是4.5-6的弱酸性、弱碱性或中性的染浴中进行。包含例如磷酸盐或羧酸盐的缓冲体系可以加入到染浴中。
本发明的另一个目的是,包含有含羟基的生物活性物质、卤素取代的脂肪族酰卤和含至少一个叔氨基的二胺或杂环芳香胺的反应产物的水溶液。
在用酯化合物水溶液处理之后,生物学活性羟基化合物在底物上的缓释通过水解开始。该过程的速度可以很容易地通过pH值和/或温度的变化进行控制。
以下实施例举例说明本发明。
I.合成实施例
I.1.化合物(101)
使薄荷醇首先与氯乙酰氯在甲基乙基酮/吡啶中反应,随后与N,N,N′,N′-四甲基乙二胺根据通用的方法反应,生成薄荷醇衍生物(101)。
NMR(D2O)δ0.72(d,3H,-CH3),0.81-0.87(m,7H),1.02-1.13(m,2H),1.35-1.55(m,2H),1.57-1.80(m,3H),1.90-2.00(m,1H),2.27(s,6H,-N(CH3)2),2.75-2.92(m,2H,-CH2-N),3.26(d,6H,+N(CH3)2),3.60-3.80(m,2H,+N-CH2-),4.65(s,2H,-(C=O)-CH2-N+),4.81(s,1H,-CH-O)
I.2.化合物(102)
使二氯苯氧氯酚首先与氯乙酰氯在甲基乙基酮/吡啶中反应,随后与N,N,N′,N′-四甲基乙二胺根据通用的方法反应,生成二氯苯氧氯酚衍生物(102)。
NMR(CDCl3)δ2.22(s,6H,-N(CH3)2),2.76(m,2H,-CH2-N),3.70(s,6H,+N(CH3)2),3.98(m,2H,+N-CH2-),5.25(s,2H,-(C=O)-CH2-N+),6.71(d,1H,Ar-H),6.94(d,1H,Ar-H),7.16-7.22(m,2H,Ar-H),7.29(d,1H,Ar-H),7.46(d,1H,Ar-H).
以同样的方式,根据通用的方法制备化合物(103)-(129):
I.3.化合物(103)
NMR(DMSO-d6)δ0.73(d,3H,-CH3),0.88(m,7H),0.90-1.15(m,2H),1.25-1-58(m,2H),1.60-1.70(m,2H),1.80-1.95(m,2H),4.31(m,2H,-(C=O)-CH2-Cl),4.65(m,1H,-CH-O).
I.4.化合物(104)
NMR DMSO-d6δ0.72(d,3H,-CH3),0.87(m,7H),0.90-1.15(m,2H),1.25-1-55(m,2H),1.55-1.70(m,2H),1.70-1.92(m,2H),1.97(q,2H,-CH2-),2.43(t,2H,-CH2-Cl),3.63(t,2H,-(C=O)-CH2-),4.59(m,1H,-CH-O).
I.5.化合物(105)
NMR(CDCl3)δ0.78(d,3H,-CH3),0.91(m,7H),0.99-1.15(m,2H),1.35-1-55(m,2H),1.60-1.74(m,2H),1.86-1.98(m,1H),2.04-2.14(m,1H),5.58(m,1H,-CH-O),5.70(m,2H,-O-CH2-Cl).
I.6.化合物(106)
NMR(DMSO-d6)δ1.14(d,6H,-CH3),2.27(s,3H,-CH3),3.00(q,1H,-CH),4.69(s,2H,-(C=O)-CH2-Cl),6.90(s,1H,Ar-H),7.05(d,1H,Ar-H),7.24(d,1H,Ar-H).
分析:C12H15ClO2
计算值:C 63.58,H 6.67,O 14.11,Cl 15.64.测量值:C 64.08,H 7.01,O 13.98,Cl 15.0.
I.7.化合物(107)
NMR(DMSO-d6)δ1.13(d,6H,-CH3),2.10(q,2H,-CH2-),2.26(s,3H,-CH3),2.76(t,2H,-CH2-Cl),2.92(q,1H,-CH),3.72(t,2H,-(C=O)-CH2-),6.84(s,1H,Ar-H),7.01(d,1H,Ar-H),7.21(d,1H,Ar-H).
分析:C14H19ClO2
计算值:C 66.01,H 7.52,O 12.56,Cl 13.92.测量值:C 65.97,H 7.57,O 12.51,Cl 13.9.
I.8.化合物(108)
NMR(CDCl3)δ1.26-1.28(d,6H,-CH3),2.38(s,3H,-CH3),3.05-3.18(m,1H,-CH),5.85(s,2H,O-CH2-Cl),6.94(s,1H,Ar-H),7.10(d,1H,Ar-H),7.26(d,1H,Ar-H).
I.9.化合物(109)
NMR(DMSO-d6)δ3.03(t,2H,-CH2-Cl),3.79(t,2H,-(C=O)-CH2-),6.95(d,1H,Ar-H),7.08(d,1H,Ar-H),7.30-7.39(m,2H,Ar-H),7.46(s,1H,Ar-H),7.71(s,1H,Ar-H).
分析:C15H10Cl4O3
计算值:C 47.41,H 2.65,O 12.63,Cl 37.31.测量值:C 47.62,H 2.86,O 12.69,Cl 37.0
I.10.化合物(110)
NMR(DMSO-d6)δ1.96(q,2H,-CH2-),2.62(t,2H,-CH2-Cl),3.62(t,2H,-(C=O)-CH2-),6.92(d,1H,Ar-H),7.09(d,1H,Ar-H),7.31-7.38(m,2H,Ar-H),7.50(s,1H,Ar-H),7.71(s,1H,Ar-H).
分析:C16H12Cl4O3
计算值:C 48.44,H 3.07,O 12.18,Cl 35.99.测量值:C 48.70,H 3.09,O 12.48,Cl 36.5.
I.11.化合物(111)
NMR(DMSO-d6)δ0.72(d,3H,-CH3),0.86-0.89(m,7H),1.00(m,2H),1.24-1.40(m,2H),1.50-1.70(m,2H),1.80-2.00(m,2H),3.29(s,6H,N(CH3)2),4.65(m,1H,-CH-O),5.19(m,2H,-(C=O)-CH2-N+),7.07(d,2H,Ar-H),8.22(d,2H,Ar-H).
I.12.化合物(112)
NMR(DMSO-d6)δ0.72(d,3H,-CH3),0.88-0.90(m,7H),1.00-1.08(m,2H),1.28-1.55(m,2H),1.55-1.70(m,2H),1.80-2.10(m,2H),4.12(s,3H,O-CH3),4.68(m,1H,-CH-O),5.50(m,2H,-(C=O)-CH2-N+),7.69(d,2H,Ar-H),8.85(d,2H,Ar-H).
I.13.化合物(113)
I.14.化合物(114)
I.15.化合物(115)
NMR(CDCl3)δ0.74(d,3H,-CH3),0.90(m,7H),0.92-1.18(m,2H),1.30-1.53(m,2H),1.60-1.75(m,2H),1.76-1.92(m,1H),1.94-2.10(m,1H),4.78(m,1H,-CH-O),6.27(m,2H,-(C=O)-CH2-N+),7.67(d,2H,Ar-H),8.26(d,2H,Ar-H),8.85(d,2H,Ar-H),9.46(d,2H,Ar-H).
I.16.化合物(116)
NMR(CDCl3)δ0.72(d,3H,-CH3),0.88(m,7H),0.92-1.15(m,2H),1.28-1.55(m,2H),1.58-1.70(m,2H),1.72-1.92(m,1H,-CH),1.94-2.08(m,1H,-CH),4.75(m,1H,-CH-O),6.29(m,2H,-(C=O)-CH2-),8.04(t,2H,Ar-H),8.50(t,1H,Ar-H),9.45(d,2H,Ar-H).
分析:C17H26NO2Cl
计算值:C 65.48,H 8.40,N 4.49,O 10.26,Cl 11.37.测量值:C 65.40,H 8.47,N 4.46,O10.27,Cl 11.5.
I.17.化合物(117)
NMR(CDCl3)δ1.17(d,6H,-CH3),,2.28(s,6H,N(CH3)2),2.29(s,3H,-CH3),2.82-2.87(m,2H,-CH2-),2.96(q,1H,-CH),3.81(s,6H,+N(CH3)2),4.05-4.10(m,2H,+N-CH2-),5.43(s,2H,-(C=O)-CH2-N+),6.80(s,1H,Ar-H),7.03(d,1H,Ar-H),7.18(d,1H,Ar-H).
分析:C18H34N2O2Cl
计算值:C 62.50,H 9.91,N 8.10,O 9.25,Cl 10.25.测量值:C 62.49,H 9.13,N 8.10,O9.45,Cl 10.5.
I.18.化合物(118)
I.19.化合物(119)
I.20.化合物(120)
I.21.化合物(121)
I.22.化合物(122)
I.23.化合物(123)
I.24.化合物(124)
I.25.化合物(125)
I.26.化合物(126)
I.27.化合物(127)
I.28.化合物(128)
I.29.化合物(129)
II.应用实施例
II.1将15克在60℃下,在10分钟的时间内用市售润湿剂(TINOVETIN JU,由Ciba Specialty Chemicals公司提供)预处理并用冷水冲洗的聚丙烯腈(PAN)织物(Dralon 5-4301)样品固定在载体材料上,并在Ahiba型尽染机中用以下组合物进行处理:
7.5毫升硫酸钠水溶液(100g/l)
2.25毫升乙酸钠水溶液(100g/l)
2.25毫升80%的乙酸
233.5毫升水
3.0毫升阳离子阻滞剂(TINEGAL MR,Ciba Specialty Chemicals)(100g/l)
1.5毫升式(101)化合物的水溶液(100g/l)
在98℃下保温20分钟;冷却到室温后,染浴的pH值是4.7。将PAN织物样品用冷水冲洗,随后晾干。所得PAN织物包含有隐匿(latent)的薄荷醇。薄荷醇从该织物中逐渐再生;薄荷醇的释放速度通过pH值进行控制。
II.2如实施例II.1中所述,用以下组合物处理PAN织物(14.9g):
7.5毫升硫酸钠水溶液(100g/l)
2.25毫升乙酸钠水溶液(100g/l)
2.25毫升80%的乙酸
232.75毫升水
1.5毫升阳离子阻滞剂(TINEGAL MR,Ciba Specialty Chemicals)(100g/l)
3.75毫升式(101)化合物的水溶液(100g/l)
在98℃下保温20分钟;冷却到室温后,染浴的pH值是4.7。将PAN织物样品用冷水冲洗,随后晾干。所得PAN织物包含有隐匿的薄荷醇。薄荷醇从该织物中逐渐再生;薄荷醇的释放速度通过pH值进行控制。
II.3如实施例II.1中所述,用以下组合物处理PAN织物(15g):
7.5毫升硫酸钠水溶液(100g/l)
2.25毫升乙酸钠水溶液(100g/l)
2.25毫升80%的乙酸
230.5毫升水
7.5毫升式(101)化合物的水溶液(100g/l)
在98℃下保温20分钟;冷却到室温后,染浴的pH值是5.0。将PAN织物样品用冷水冲洗,随后晾干。所得PAN织物包含有隐匿的薄荷醇。薄荷醇从该织物中逐渐再生;薄荷醇的释放速度通过pH值进行控制。
II.4如实施例II.1中所述,用以下组合物处理PAN织物(14.8g):
2.25毫升乙酸钠水溶液(100g/l)
2.25毫升80%的乙酸
220毫升水
25.5毫升式(101)化合物的水溶液(100g/l)
在98℃下保温20分钟;冷却到室温后,染浴的pH值是5.2。将PAN织物样品用冷水冲洗,随后晾干。所得PAN织物包含有隐匿的薄荷醇。薄荷醇从该织物中逐渐再生;薄荷醇的释放速度通过pH值进行控制。
II.5制备包含有20g/l化合物(101)的轧染液并在20-25℃下以70-80%的吸浆率施用于棉织品上。干燥后(在70-130℃下干燥65-15秒),所得织物包含有隐匿的薄荷醇。薄荷醇从该织物中逐渐再生;薄荷醇的释放速度通过pH值进行控制。
II.6在棉织品上使用化合物(102)代替(101)进行相同的处理。处理后,二氯苯氧氯酚在纤维上慢慢地释放,从而确保随着时间的推移有充分的抗微生物保护作用。
II.7类似地,用式(101)和(102)化合物的水溶液配方处理棉织物。处理后,薄荷醇和二氯苯氧氯酚在纤维上慢慢地释放,从而确保随着时间的推移既有清新的芳香味,又有充分的抗微生物保护作用。
II.8将浓缩的化合物(101)的水溶液配方喷涂在纤维性底物(如纸张,棉织品)上。风干后,包含有隐匿薄荷醇的底物在水解时释放出薄荷醇。
II.9将浓缩的化合物(102)的水溶液配方喷涂在纤维性底物(如纸张,棉织品)上。风干后,包含有隐匿二氯苯氧氯酚的底物在水解时释放出二氯苯氧氯酚。
Claims (11)
1.含羟基的生物活性物质在底物上受控释放的方法,其包括使所述含羟基的物质依次与卤素取代的脂肪族酰卤,和包含至少一个叔氨基的二胺或者杂环芳香胺反应,并将这样得到的水溶性酯施用于底物上,最后使酯在底物上水解。
2.根据权利要求1的方法,其中含羟基的生物活性物质是药物,植物防护剂,杀虫剂,抗微生物剂,调味剂或化妆品。
3.根据权利要求2的方法,其中含羟基的生物活性物质是杀虫剂或抗微生物剂。
4.根据权利要求1的方法,其中底物选自木材,塑料,纸张或纺织材料。
5.根据权利要求5的方法,其中底物是纸张或织物。
6.根据权利要求1的方法,其中卤素取代的脂肪族酰卤是乙酰氯或4-氯丁酰氯。
7.根据权利要求1的方法,其中含至少一个叔氨基的二胺是通式R1R2N-A-NR3R4的二胺,其中R1和R2独立地为C1-C7烷基,R3和R4独立地为H或C1-C7烷基,A是C1-C7直链或支链烷基链。
8.根据权利要求7的方法,其中含至少一个叔氨基的二胺是1,2-二(二甲氨基)乙烷。
9.根据权利要求1的方法,其中杂环芳香胺是未取代或取代的吡啶、联吡啶、咪唑或噁唑。
10.根据权利要求1的方法,其中杂环芳香胺是吡啶,4-二甲基氨基吡啶,4-甲氧基吡啶,4-氰基吡啶或4,4′-联吡啶。
11.一种水溶液,其包含有含羟基的生物活性物质、卤素取代的脂肪族酰卤和含至少一个叔氨基的二胺或杂环芳香胺的反应产物。
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EP (1) | EP1532310A1 (zh) |
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KR (1) | KR20050056990A (zh) |
CN (1) | CN1311122C (zh) |
AU (1) | AU2003255460A1 (zh) |
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AR207771A1 (es) * | 1974-03-07 | 1976-10-29 | Ciba Geigy Ag | Nuevos colorantes de dispersion hidrosulobles en estado intermedio para materiales textiles sinteticos |
US4026945A (en) * | 1974-10-03 | 1977-05-31 | Millmaster Onyx Corporation | Anti-microbial quaternary ammonium co-polymers |
ES2179850T3 (es) * | 1993-09-30 | 2003-02-01 | Procter & Gamble | Sistema de liberacion de sustancia activa. |
EP0752465A1 (en) * | 1995-06-01 | 1997-01-08 | The Procter & Gamble Company | Betaine esters for delivery of alcohols |
EP0771785B1 (en) * | 1995-11-02 | 2002-01-09 | The Procter & Gamble Company | Amino ester compounds of perfume alcohols and their use in cleaning or laundry compositions |
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EP0799885A1 (en) * | 1996-04-01 | 1997-10-08 | The Procter & Gamble Company | Betaine ester compounds of active alcohols |
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WO2004020729A1 (en) | 2004-03-11 |
CN1311122C (zh) | 2007-04-18 |
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