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1. 发明授权

US06326517B1 Method of producing benzamides 失效
标题翻译：生产苯甲酰胺的方法
公开(公告)号：US06326517B1
公开(公告)日：2001-12-04
申请号：US09458079
申请日：1999-12-10
申请人： Takashi Kume , Michio Ishida , Satoru Narizuka , Yuzuru Morino , Makoto Koide
发明人： Takashi Kume , Michio Ishida , Satoru Narizuka , Yuzuru Morino , Makoto Koide
IPC分类号： C07C23100
CPC分类号： C07C231/10 , C07C233/65
摘要： A method of producing benzamides represented by the following general formula (1): where R is trifluoromethyl group, trifluoromethyloxy group, halogen (fluorine, chlorine, bromine or iodine), nitro group, acetyl group, cyano group, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or a alkoxycarbonyl group having 2 to 5 carbon atoms; and n is 0 or an integer ranging from 1 to 3. The method comprises the step of allowing an aromatic compound represented by the following general formula (2) to react with carbon monoxide and ammonia in the presence of a metal of the group VIII of the periodic table and phosphine: where X is halogen (fluorine, chlorine, bromine or iodine), trifluoromethanesulfonate group, alkylsulfonate group having 1 to 4 carbon atoms, or substituted or unsubstituted arylsulfonate group; R is trifluoromethyl group, trifluoromethyloxy group, halogen (fluorine, chlorine, bromine or iodine), nitro group, acetyl group, cyano group, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, or alkoxycarbonyl group having 2 to 5 carbon atoms; and n is 0 or an integer ranging from 1 to 3.
摘要翻译：一种生产由以下通式（1）表示的苯甲酰胺的方法：其中R是三氟甲基，三氟甲氧基，卤素（氟，氯，溴或碘），硝基，乙酰基，氰基，具有1-4个碳原子数1〜4的烷氧基或碳原子数2〜5的烷氧基羰基。并且n为0或1至3的整数。该方法包括以下通式（2）表示的芳族化合物与一氧化碳和氨在VIII族金属存在下反应的步骤：周期表和膦：其中X是卤素（氟，氯，溴或碘），三氟甲磺酸酯基，具有1至4个碳原子的烷基磺酸酯基或取代或未取代的芳基磺酸酯基; R为三氟甲基，三氟甲氧基，卤素（氟，氯，溴或碘），硝基，乙酰基，氰基，碳原子数1〜4的烷基，碳原子数1〜4的烷氧基， 2至5个碳原子; n为0或1〜3的整数。

2. 发明授权

US06175041B1 Process for producing trifluoromethylbenzylamines 失效
标题翻译：制备三氟甲基苄胺的方法
公开(公告)号：US06175041B1
公开(公告)日：2001-01-16
申请号：US09521009
申请日：2000-03-07
申请人： Seiji Takasaki , Takahiro Koizumi , Takashi Kume , Michio Ishida , Satoru Narizuka , Eri Tsukada
发明人： Seiji Takasaki , Takahiro Koizumi , Takashi Kume , Michio Ishida , Satoru Narizuka , Eri Tsukada
IPC分类号： C07C20900
CPC分类号： C07C209/48 , C07C211/29
摘要： The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1). This process includes hydrogenating a trifliuoromethylbenzonitrile represented by the following general formula (2) by hydrogen in an organic solvent in the presence of ammonia, using a Raney catalyst, where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4, where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine easily and inexpensively at an extremely high yield.
摘要翻译：本发明涉及一种由以下通式（1）表示的三氟甲基苄胺的制备方法。该方法包括使用阮内催化剂，在氨的存在下，在有机溶剂中，用氢气氢化由以下通式（2）表示的三氟甲基苄腈，其中每个R独立地表示选自氟，氯，溴的卤素和碘，碳原子数为1-4的烷基，碳原子数为1-4的烷氧基，氨基，羟基或三氟甲基，n为0-4的整数其中R和n如上定义。通过该方法，可以以极高的收率容易且廉价地得到三氟甲基苄基胺。

3. 发明授权

US08580486B2 Salt having fluorine-containing carbanion structure, derivative thereof, photoacid generator, resist material using the photoacid generator, and pattern forming method 有权
标题翻译：具有含氟碳负离子结构的盐，其衍生物，光酸产生剂，使用光酸产生剂的抗蚀剂材料和图案形成方法
公开(公告)号：US08580486B2
公开(公告)日：2013-11-12
申请号：US12922300
申请日：2009-03-10
申请人： Masashi Nagamori , Satoru Narizuka , Susumu Inoue , Takashi Kume
发明人： Masashi Nagamori , Satoru Narizuka , Susumu Inoue , Takashi Kume
IPC分类号： G03F7/039 , G03F7/20 , G03F7/30 , G03F7/38 , G03F7/029
CPC分类号： C07C381/12 , C07C317/18 , C07C2603/74 , C08F220/28 , G03F7/0045 , G03F7/0046 , G03F7/0397 , C08F220/18 , C08F220/24 , C08F232/08
摘要： There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.
摘要翻译：提供具有含氟碳负离子结构的酸或具有含氟碳负离子结构的盐，其由以下通式（1）表示。通过使用产生该酸的化学放大抗蚀剂材料的光酸产生剂，可以提供对ArF准分子激光等具有高灵敏度的光酸产生剂，其中产生的酸（光产生酸）具有具有足够高的酸度，并且在抗蚀剂溶剂中具有高溶解性和与树脂的优异的相容性，以及含有这种光致酸产生剂的抗蚀剂材料。

4. 发明申请

US20110070544A1 Novel Salt Having Fluorine-Containing Carbanion Structure, Derivative Thereof, Photoacid Generator, Resist Material Using the Photoacid Generator, and Pattern Forming Method 有权
标题翻译：具有含氟碳酸盐结构的新型盐，其衍生物，光酸发生剂，使用光致酸发生剂的抗蚀材料和图案形成方法
公开(公告)号：US20110070544A1
公开(公告)日：2011-03-24
申请号：US12922300
申请日：2009-03-10
申请人： Masashi Nagamori , Satoru Narizuka , Susumu Inoue , Takashi Kume
发明人： Masashi Nagamori , Satoru Narizuka , Susumu Inoue , Takashi Kume
IPC分类号： G03F7/004 , C07C315/00 , C07D327/04 , C07C69/00 , C07C69/74 , C07C309/00 , C07C261/00 , G03F7/20
CPC分类号： C07C381/12 , C07C317/18 , C07C2603/74 , C08F220/28 , G03F7/0045 , G03F7/0046 , G03F7/0397 , C08F220/18 , C08F220/24 , C08F232/08
摘要： There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.
摘要翻译：提供具有含氟碳负离子结构的酸或具有含氟碳负离子结构的盐，其由以下通式（1）表示。通过使用产生该酸的化学放大抗蚀剂材料的光酸产生剂，可以提供对ArF准分子激光等具有高灵敏度的光酸产生剂，其中产生的酸（光产生酸）具有具有足够高的酸度，并且在抗蚀剂溶剂中具有高溶解性和与树脂的优异的相容性，以及含有这种光致酸产生剂的抗蚀剂材料。

5. 发明授权

US06506951B1 Process for producing brominated trifluoromethylbenzenes 失效
标题翻译：溴化三氟甲基苯的制备方法
公开(公告)号：US06506951B1
公开(公告)日：2003-01-14
申请号：US09551912
申请日：2000-04-19
申请人： Eri Tsukada , Mikio Ujiie , Shozo Kaneda , Satoru Narizuka , Takashi Kume
发明人： Eri Tsukada , Mikio Ujiie , Shozo Kaneda , Satoru Narizuka , Takashi Kume
IPC分类号： C07C2200
CPC分类号： B01J27/135 , B01J27/10 , B01J27/128 , C07C17/12 , C07C25/13
摘要： The invention relates to a process for producing a brominated trifluoromethylbenzene represented by the general formula (1). This process includes brominating in a liquid or gas phase a trifluoromethylbenzene, represented by the general formula (2), by bromine in the presence of a catalyst under a condition that the bromine is coexistent with chlorine, where n is an integer of 1-2, and m is an integer of 1-3 where n is an integer of 1-2. The catalyst is preferably iron chloride in the case of the bromination in a liquid phase. It is preferably activated carbon carrying thereon iron chloride in the case of the bromination in a gas phase. The trifluoromethylbenzene is turned to the brominated trifluoromethylbenzene with high reactivity and high yield.
摘要翻译：本发明涉及由通式（1）表示的溴代三氟甲基苯的制备方法。该方法包括在液相或气相中溴在溴中与氯共存的条件下，在溴存在下，用溴在通式（2）表示的三氟甲基苯中溴化，其中n为1-2的整数，m为1-3的整数，其中n为1-2的整数。在液相中溴化的情况下，催化剂优选为氯化铁。在气相溴化的情况下，优选载有氯化铁的活性炭。三氟甲基苯转化为溴化三氟甲基苯，反应性高，产率高。

6. 发明授权

US06268527B1 Method for producing benzoic acid derivatives 失效
标题翻译：苯甲酸衍生物的制备方法
公开(公告)号：US06268527B1
公开(公告)日：2001-07-31
申请号：US09452945
申请日：1999-12-02
申请人： Makoto Koide , Michio Ishida , Yuzuru Morino , Seiji Hasegawa , Satoru Narizuka , Takashi Kume
发明人： Makoto Koide , Michio Ishida , Yuzuru Morino , Seiji Hasegawa , Satoru Narizuka , Takashi Kume
IPC分类号： C07C5110
CPC分类号： C07C51/10 , C07C63/70
摘要： The invention relates to a method for producing a benzoic acid derivative represented by the general formula (1). The method includes the step of reacting an aromatic compound represented by the general formula (2), with carbon monoxide and a hydroxy compound (i.e., water or an alcohol), in the presence of (a) a metal compound containing a metal of 8, 9 and 10 groups of periodic table, (b) a first phosphine derivative represented by the general formula (R1)2P—Q—P(R1)2, and (c) a base, It is possible to easily and efficiently produce the benzoic acid derivative by the method.
摘要翻译：本发明涉及通式（1）表示的苯甲酸衍生物的制造方法。该方法包括在（a）含有金属8的金属化合物的存在下使由通式（2）表示的芳族化合物与一氧化碳和羟基化合物（即水或醇）反应的步骤，9组和10组周期表，（b）由通式（R1）2P-QP（R1）2表示的第一膦衍生物和（c）碱，可以容易且有效地制备苯甲酸衍生的方法。

7. 发明授权

US06362372B1 Process for producing trifluoromethylbenzylamines 有权
公开(公告)号：US06362372B1
公开(公告)日：2002-03-26
申请号：US09833210
申请日：2001-04-12
申请人： Satoru Narizuka , Takashi Kume
发明人： Satoru Narizuka , Takashi Kume
IPC分类号： C07C20900
摘要： The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1), where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4. The process includes hydrogenating a trifluoromethylbenzonitrile by hydrogen in an organic solvent in the presence of ammonia and a catalyst containing a platinum group element. This trifluoromethylbenzonitrile is represented by the following general formula (2), where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine at an extremely high yield.

8. 发明授权

US06878663B2 Method for producing palladium complex compound 失效
标题翻译：钯配合物的制造方法
公开(公告)号：US06878663B2
公开(公告)日：2005-04-12
申请号：US10116057
申请日：2002-04-05
申请人： Takashi Kume , Satoru Narizuka , Makoto Koide , Koichi Mikami , Manabu Hatano , Masahiro Terada
发明人： Takashi Kume , Satoru Narizuka , Makoto Koide , Koichi Mikami , Manabu Hatano , Masahiro Terada
IPC分类号： C07F15/00 , C07F17/02
CPC分类号： C07F15/006 , C07F15/0066
摘要： An aromatic compound represented by the general formula Ar1X is reacted with a palladium compound and a phosphine derivative, in the presence of a first basic substance, thereby producing a palladium-complex compound represented by the general formula Ar1—PdL2X. This palladium-complex compound is reacted with a benzoic acid represented by the general formula Ar2—COOH, in the presence of a second basic substance, thereby producing another palladium-complex compound represented by the following general formula. The above palladium-complex compounds are useful as catalysts and can be produced easily by the above reactions. In the above general formulas, Ar1 is an aryl group; and X is a halogen that is fluorine, chlorine, bromine or iodine, trifluoromethanesulfonate group, an alkylsulfonate group having a carbon atom number of 1-4, or a substituted or unsubstituted arylsulfonate group; each L is independently a phosphine ligand; and Ar2 is an aryl group.
摘要翻译：在通式Ar 1 X表示的芳香族化合物与钯化合物和膦衍生物在第一碱性物质的存在下反应，由此制备由通式Ar 1〜 PdL2X。在第二碱性物质的存在下，使该钯络合物与通式为Ar 2 -COOH表示的苯甲酸反应，由此生成由以下通式表示的另一种钯络合物。复合化合物可用作催化剂，并且可以通过上述反应容易地制备。在上述通式中，Ar 1是芳基; X是氟，氯，溴或碘的卤素，三氟甲磺酸酯基，碳原子数为1-4的烷基磺酸酯基或取代或未取代的芳基磺酸酯基; 每个L独立地是膦配体; Ar 2为芳基。

9. 发明授权

US06706905B1 Method for producing palladium complex compound 失效
标题翻译：钯配合物的制造方法
公开(公告)号：US06706905B1
公开(公告)日：2004-03-16
申请号：US09458080
申请日：1999-12-10
申请人： Takashi Kume , Satoru Narizuka , Makoto Koide , Koichi Mikami , Manabu Hatano , Masahiro Terada , Michio Ishida , Yuzuru Morino
发明人： Takashi Kume , Satoru Narizuka , Makoto Koide , Koichi Mikami , Manabu Hatano , Masahiro Terada , Michio Ishida , Yuzuru Morino
IPC分类号： C07F1702
CPC分类号： C07F15/006 , C07F15/0066
摘要： An aromatic compound represented by the general formula Ar1X is reacted with a palladium compound and a phosphine derivative, in the presence of a first basic substance, thereby producing a palladium-complex compound represented by the general formula Ar1—PdL2X. This palladium-complex compound is reacted with a benzoic acid represented by the general formula Ar2—COOH, in the presence of a second basic substance, thereby producing another palladium-complex compound represented by the following general formula. The above palladium-complex compounds are useful as catalysts and can be produced easily by the above reactions. In the above general formulas, Ar1 is an aryl group; and X is a halogen that is fluorine, chlorine, bromine or iodine, trifluoromethanesulfonate group, an alkylsulfonate group having a carbon atom number of 1-4, or a substituted or unsubstituted arylsulfonate group; each L is independently a phosphine ligand; and Ar2 is an aryl group.
摘要翻译：在通式Ar 1 X表示的芳香族化合物与钯化合物和膦衍生物在第一碱性物质的存在下反应，由此制备由通式Ar 1〜 PdL2X。在第二碱性物质的存在下，使该钯络合物与通式为Ar 2 -COOH表示的苯甲酸反应，由此生成由以下通式表示的另一种钯络合物。复合化合物可用作催化剂，并且可以通过上述反应容易地制备。在上述通式中，Ar 1是芳基; X是氟，氯，溴或碘的卤素，三氟甲磺酸酯基，碳原子数为1-4的烷基磺酸酯基或取代或未取代的芳基磺酸酯基; 每个L独立地是膦配体; Ar 2为芳基。

10. 发明授权

US06376712B2 Process for producing trifluoromethylbenzylamines 失效
标题翻译：制备三氟甲基苄胺的方法
公开(公告)号：US06376712B2
公开(公告)日：2002-04-23
申请号：US09833211
申请日：2001-04-12
申请人： Satoru Narizuka , Eri Tsukada , Takashi Kume
发明人： Satoru Narizuka , Eri Tsukada , Takashi Kume
IPC分类号： C07C21100
CPC分类号： C07C209/40 , C07C211/29
摘要： The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1), where R1 represents hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, or trifluoromethyl group. This process includes the step of reducing an oxime by hydrogen in an organic solvent in the presence of a catalyst and ammonia. The oxime is represented by the general formula (2), where R1 is defined as above, and R2 represents hydrogen atom, an alkyl group or an aralkyl group. With this process, the trifluoromethylbenzylamine can be produced with high yield.
摘要翻译：本发明涉及由通式（1）表示的三氟甲基苄胺的制备方法，其中R1表示氢原子，选自氟，氯，溴和碘的卤素原子或三氟甲基。该方法包括在催化剂和氨的存在下，通过有机溶剂中的氢还原肟的步骤。肟由通式（2）表示，其中R 1如上定义，R 2表示氢原子，烷基或芳烷基。通过该方法，可以高产率制备三氟甲基苄胺。

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