公开(公告)号：US07166659B2

公开(公告)日：2007-01-23

申请号：US10812728

申请日：2004-03-30

申请人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

发明人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

IPC分类号： C08K5/3475

CPC分类号： C07D401/04 ,  C07D249/20 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C07D409/14

摘要： Compounds of formula I or II where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and E1 and E2 are independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

摘要翻译： 式I或II的化合物，其中R是芳基部分，例如苯基，萘基或联苯基，或被一个或多个三氟甲基，溴或氰基取代的苯基，和E 1和 2个独立地是氢，烷基，芳烷基等通过在苯并环的5-位被卤素原子取代的苯并三唑与芳基硼酸或酯在过渡金属 催化剂，如二乙酸钯（II）。 式I的苯并三唑化合物作为汽车涂料和蜡烛蜡的稳定剂是特别有效的。

公开(公告)号：US06649770B1

公开(公告)日：2003-11-18

申请号：US09722876

申请日：2000-11-27

申请人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

发明人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

IPC分类号： C07D24920

CPC分类号： C07D401/04 ,  C07D249/20 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C07D409/14

摘要： Compounds of formula I or II where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and E1 and E2 are independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

摘要翻译： 式I或II的化合物，其中R是芳基部分，例如苯基，萘基或联苯基，或被一个或多个三氟甲基，溴或氰基取代的苯基，E1和E2独立地是氢，烷基，芳烷基等 通过在过渡金属催化剂如二乙酸钯（II）的存在下，将苯并环的5-位被卤素原子取代的苯并三唑与芳基硼酸或酯反应。 式I的苯并三唑化合物作为汽车涂料和蜡烛蜡的稳定剂是特别有效的。

公开(公告)号：US06605727B2

公开(公告)日：2003-08-12

申请号：US10315692

申请日：2002-12-10

申请人： Mervin G. Wood ,  Deborah DeHessa ,  Joseph Suhadolnik ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

发明人： Mervin G. Wood ,  Deborah DeHessa ,  Joseph Suhadolnik ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

IPC分类号： C07D24920

CPC分类号： C07D249/20 ,  C07C245/08

摘要： Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, for example a trifluoromethyl group, which involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

公开(公告)号：US06353113B1

公开(公告)日：2002-03-05

申请号：US09632217

申请日：2000-08-03

申请人： Mervin G. Wood ,  Deborah DeHessa ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

发明人： Mervin G. Wood ,  Deborah DeHessa ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

IPC分类号： C07D24920

CPC分类号： C07C245/08 ,  C07D249/20

摘要： A process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, preferably a trifluoromethyl group, involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or preferably nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means.

摘要翻译： 制备苯并三唑UV吸收剂的方法，其在苯环的5-位，优选三氟甲基基团中含有全氟烷基部分，包括使用浓硫酸加亚硝酸钠或优选亚硝酰基硫酸使全氟烷基取代的邻硝基苯胺重氮化，形成 通过重氮盐中间体相应的单偶氮苯中间体，其通过常规还原方法还原成相应的5-全氟烷基取代的2H-苯并三唑UV吸收剂化合物。

公开(公告)号：US06815550B2

公开(公告)日：2004-11-09

申请号：US10315693

申请日：2002-12-10

申请人： Mervin G. Wood ,  Deborah DeHessa ,  Joseph Suhadolnik ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

发明人： Mervin G. Wood ,  Deborah DeHessa ,  Joseph Suhadolnik ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

IPC分类号： C07D24920

CPC分类号： C07D249/20 ,  C07C245/08

摘要： Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzoic ring, for example a trifluoromethyl group, which involves digitizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

摘要翻译： 提供了制备在苯甲酸环的5位上含有全氟烷基部分的2H-苯并三唑UV吸收剂的方法，例如三氟甲基，其涉及使用浓硫酸加亚硝酸钠或亚硝酰基硫酸将全氟烷基取代的邻硝基苯胺数字化 通过重氮盐中间体形成相应的单偶氮苯中间体，其通过常规还原方法还原成相应的5-全氟烷基取代的2H-苯并三唑UV吸收剂化合物。 还提供了用于制备2（2-硝基苯基偶氮）取代的酚的新颖的一锅多相反应，其是2H-苯并三唑UV吸收剂的前体。

公开(公告)号：US06703510B2

公开(公告)日：2004-03-09

申请号：US10417999

申请日：2003-04-17

申请人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

发明人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

IPC分类号： C07D24920

CPC分类号： C07D401/04 ,  C07D249/20 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C07D409/14

摘要： Compounds of formula I or II where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and E1 and E2 are independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

摘要翻译： 式I或II的化合物，其中R是芳基部分，例如苯基，萘基或联苯基，或被一个或多个三氟甲基，溴或氰基取代的苯基，E1和E2独立地是氢，烷基，芳烷基等 通过在过渡金属催化剂如二乙酸钯（II）的存在下，将苯并环的5-位被卤素原子取代的苯并三唑与芳基硼酸或酯反应。 式I的苯并三唑化合物作为汽车涂料和蜡烛蜡的稳定剂是特别有效的。

公开(公告)号：US06566507B2

公开(公告)日：2003-05-20

申请号：US09871369

申请日：2001-05-31

申请人： Mervin G. Wood ,  Deborah DeHessa ,  Joseph Suhadolnik ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

发明人： Mervin G. Wood ,  Deborah DeHessa ,  Joseph Suhadolnik ,  Andrew B. Naughton ,  Jerome Sanders ,  Jacqueline Lau ,  Rong Xiong ,  Joseph Babiarz

IPC分类号： C09B4100

CPC分类号： C07D249/20 ,  C07C245/08

摘要： Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, for example a trifluoromethyl group, which involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

公开(公告)号：US07148274B2

公开(公告)日：2006-12-12

申请号：US10764960

申请日：2004-01-26

申请人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

发明人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

IPC分类号： C08K5/3492 ,  C10L5/00

CPC分类号： C07D401/04 ,  C07D249/20 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C07D409/14

摘要： where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and E1 and E2 are independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

摘要翻译： 其中R是芳基部分，例如苯基，萘基或联苯基，或被一个或多个三氟甲基，溴或氰基取代的苯基，和E 1和E 2是 独立地，氢，烷基，芳烷基等通过在苯并环的5-位被卤素原子取代的苯并三唑与芳基硼酸或酯在过渡金属催化剂如钯（ II）二乙酸酯。 式I的苯并三唑化合物作为汽车涂料和蜡烛蜡的稳定剂是特别有效的。

公开(公告)号：US06774238B2

公开(公告)日：2004-08-10

申请号：US10602094

申请日：2003-04-17

申请人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

发明人： Stephen D. Pastor ,  Andrew B. Naughton ,  Robert Detlefsen ,  Mervin G. Wood ,  Joseph Suhadolnik ,  Anthony DeBellis ,  Deborah DeHessa

IPC分类号： C07D24920

CPC分类号： C07D401/04 ,  C07D249/20 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C07D409/14

摘要： Compounds of formula I or II where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and E1 and E2 are independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium(II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

摘要翻译： 式I或II的化合物，其中R是芳基部分，例如苯基，萘基或联苯基，或被一个或多个三氟甲基，溴或氰基取代的苯基，E1和E2独立地是氢，烷基，芳烷基等 通过在过渡金属催化剂如二乙酸钯（II）的存在下，将苯并环的5-位被卤素原子取代的苯并三唑与芳基硼酸或酯反应。 式I的苯并三唑化合物作为汽车涂料和蜡烛蜡的稳定剂是特别有效的。