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1. 发明授权

US5726296A Process for preparing photoactive coumarin derivatives 失效
标题翻译：制备光活性香豆素衍生物的方法
公开(公告)号：US5726296A
公开(公告)日：1998-03-10
申请号：US813098
申请日：1997-03-07
申请人： Mohammad Aslam , Michael T. Sheehan , Debasish Kuila
发明人： Mohammad Aslam , Michael T. Sheehan , Debasish Kuila
IPC分类号： C07C49/825 , C07C323/22 , C07D311/56 , C07D335/06 , G03F7/022 , C07D311/20
CPC分类号： G03F7/022 , C07D311/56
摘要： Novel processes for the preparation of a new class of coumarin derivatives, which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications, are disclosed and claimed. The process involves a multi-step synthetic method for the preparation of ether, ester, carbonate, or sulfonate derivative of 5-hydroxy, 6-hydroxy, or 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarin starting from the corresponding dihydroxyacetophenone. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
摘要翻译：新的制备新型香豆素衍生物的新方法被公开并要求保护，其可用作各种应用中的光敏化合物，包括光致抗蚀剂和其它光电子应用。该方法涉及一种用于制备5-羟基，6-羟基或7-羟基-3-重氮基-4-氧代-3,4-二氢香豆素的醚，酯，碳酸酯或磺酸酯衍生物的多步合成方法从相应的二羟基苯乙酮。由本发明方法形成的化合物在深紫外（DUV）区域（约250nm）中表现出非常高的光敏性，因此可用作DUV光致抗蚀剂制剂中的光活性化合物。

2. 发明授权

US5726295A Photoactive coumarin derivatives 失效
标题翻译：光敏香豆素衍生物
公开(公告)号：US5726295A
公开(公告)日：1998-03-10
申请号：US813097
申请日：1997-03-07
申请人： Mohammad Aslam , Michael T. Sheehan , Debasish Kuila
发明人： Mohammad Aslam , Michael T. Sheehan , Debasish Kuila
IPC分类号： G03F7/031 , C07D311/12 , C07D311/56 , C07D335/06 , G03F7/022 , C07D311/20
CPC分类号： C07D335/06 , C07D311/12 , C07D311/56 , G03F7/022
摘要： A new class of 3,4-dihydrocoumarin derivatives which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include ether, ester, carbonate, and sulfonate derivatives of 5-hydroxy, 6-hydroxy, and 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarins. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
摘要翻译：公开和要求保护的新一类3,4-二氢香豆素衍生物，其可用作各种应用中的光活性化合物，包括光刻胶和其它光电应用。优选的实施方案包括5-羟基，6-羟基和7-羟基-3-重氮基-4-氧代-3,4-二氢香豆素的醚，酯，碳酸酯和磺酸酯衍生物。这些化合物在深紫外（DUV）区域（约250nm）中表现出非常高的光敏性，因此可用作DUV光致抗蚀剂制剂中的光活性化合物。

3. 发明授权

US5438142A Functionalized tris(hydroxyphenyl) compounds 失效
标题翻译：功能化的三（羟基苯基）化合物
公开(公告)号：US5438142A
公开(公告)日：1995-08-01
申请号：US105824
申请日：1993-08-10
申请人： John R. Fritsch , Olan S. Fruchey , Debasish Kuila , George Kvakovszky , Mark A. Murphy , Michael T. Sheehan , James R Sounik , Richard Vicari
发明人： John R. Fritsch , Olan S. Fruchey , Debasish Kuila , George Kvakovszky , Mark A. Murphy , Michael T. Sheehan , James R Sounik , Richard Vicari
IPC分类号： C07C37/20 , C07C39/15 , C07C39/16 , C07C43/23 , C07C45/00 , C07C45/54 , C07C45/68 , C07C45/69 , C07C49/825 , C07C49/84 , C07C255/32 , C07C255/41 , C07D211/22 , C07D211/46 , C07D249/20 , C07D295/185 , C08G18/38 , C08G59/24 , C08G59/26 , C08G75/20 , C08G75/23 , C08K5/00 , C08K5/07 , C08K5/3432 , C08K5/3435 , C08K5/3472 , C08K5/3475 , C08L101/00 , C09B69/10 , C09K3/00 , C09K15/08 , C09K15/24 , C09K15/30 , C07D249/16 , C08F26/06 , C08K5/34
CPC分类号： C07D295/185 , C07C255/41 , C07C37/14 , C07C37/20 , C07C39/15 , C07C39/16 , C07C39/367 , C07C45/008 , C07C45/54 , C07C45/68 , C07C45/69 , C07D211/46 , C07D249/20 , C08G18/3851 , C08G59/245 , C08G59/26 , C08G75/20 , C08G75/23 , C08K5/0008
摘要： Compounds useful as polymer stabilizers which are polymerizable into condensation polymer systems are disclosed and claimed. A particularly preferred embodiment is 1-(3'-(benzotriazol-2"-yl)-4'-hydroxyphenyl)-1,1-bis(4-hydroxyphenyl)ethane.
摘要翻译：公开并要求保护作为可聚合成缩聚物体系的聚合物稳定剂的化合物。特别优选的实施方案是1-（3' - （苯并三唑-2“ - 基）-4'-羟基苯基）-1,1-双（4-羟基苯基）乙烷。

4. 发明授权

US5773591A Process for preparing coumarin sulfonates 失效
标题翻译：香豆素磺酸盐的制备方法
公开(公告)号：US5773591A
公开(公告)日：1998-06-30
申请号：US813106
申请日：1997-03-07
申请人： Mohammad Aslam , Michael T. Sheehan , George Kvakovszky
发明人： Mohammad Aslam , Michael T. Sheehan , George Kvakovszky
IPC分类号： G03F7/004 , C07D311/56 , C07D335/06 , C07D311/20
CPC分类号： C07D311/56
摘要： A novel process for preparing sulfonic acid esters and amides of benzo-heterocyclic diazo diketo compounds, such as substituted diazo-4-oxo-3,4-dihydrocoumarins, which are useful synthetic intermediates in a wide variety of applications including photoresists, opto-electronics, agricultural, and pharmaceutical applications is disclosed and claimed. The process comprises the steps of (a) subjecting a substituted benzo-heterocyclic .beta.-keto-enol compound to suitable diazo transfer conditions in the presence of a diazo transfer agent; (b) subjecting the so formed diazo diketo compound to suitable halosulfonation conditions in the presence of a halosulfonation agent; and (c) subjecting the so formed halosulfonyl aromatic compound to suitable substitution reaction in the presence of an alcohol or an amine to form the corresponding sulfonic acid ester or amide of benzo-heterocyclic diazo diketo compound. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
摘要翻译：一种用于制备苯并杂环重氮二酮化合物的磺酸酯和酰胺的新方法，例如取代的重氮-4-氧代-3,4-二氢香豆素，其在各种应用中是有用的合成中间体，包括光致抗蚀剂，光电子，农业和药物应用被公开和要求保护。该方法包括以下步骤：（a）在重氮转移剂存在下使取代的苯并杂环的β-酮 - 烯醇化合物进行合适的重氮转移条件; （b）在卤代磺化剂的存在下使如此形成的重氮二酮化合物进行适当的卤代磺化条件; 和（c）使这样形成的卤代磺酰基芳族化合物在醇或胺的存在下进行适当的取代反应，形成相应的苯并杂环重氮二酮化合物的磺酸酯或酰胺。由本发明方法形成的化合物在深紫外（DUV）区域（约250nm）中表现出非常高的光敏性，因此可用作DUV光致抗蚀剂制剂中的光活性化合物。

5. 发明授权

US5739295A Photoactive coumarin sulfonate compounds 失效
标题翻译：光敏香豆素磺酸盐化合物
公开(公告)号：US5739295A
公开(公告)日：1998-04-14
申请号：US813099
申请日：1997-03-07
申请人： Mohammad Aslam , Michael T. Sheehan , George Kvakovszky , Kenneth G. Davenport , Douglas J. Gordon
发明人： Mohammad Aslam , Michael T. Sheehan , George Kvakovszky , Kenneth G. Davenport , Douglas J. Gordon
IPC分类号： C07D311/56 , C07D335/06 , C08F12/30 , C08G8/28 , C07D311/20
CPC分类号： C07D335/06 , C07D311/56
摘要： A new class of 3-diazo-3,4-dihydrocoumarin compounds which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include 6-sulfonyl-3-diazo-4-oxo-3,4-dihydrocoumarin esters. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
摘要翻译：公开和要求保护的新类型的可用作光活性化合物的3-重氮-3,4-二氢香豆素化合物，包括光致抗蚀剂和其他光电子应用。优选的实施方案包括6-磺酰基-3-重氮基-4-氧代-3,4-二氢香豆素酯。这些化合物在深紫外（DUV）区域（约250nm）中表现出非常高的光敏性，因此可用作DUV光致抗蚀剂制剂中的光活性化合物。

6. 发明授权

US07897697B2 Epoxy resin, blocked polyisocyanate or polymers with polyhydroxystyrenes having novolak structure 有权
标题翻译：环氧树脂，封端多异氰酸酯或具有酚醛清漆结构的聚羟基苯乙烯的聚合物
公开(公告)号：US07897697B2
公开(公告)日：2011-03-01
申请号：US12456895
申请日：2009-06-24
申请人： Michael T. Sheehan , Edward G. Zey
发明人： Michael T. Sheehan , Edward G. Zey
IPC分类号： C08G61/02 , C08L63/00 , C08L87/00
CPC分类号： C09D125/18 , C08G61/04 , C08G2261/312 , G03F7/023 , G03F7/038 , Y02P20/582
摘要： A process for preparing derivatized poly(4-hydroxystryrene) having a novolak type structure which comprises the steps of (i) supplying a solution of methanol containing 4-hydroxyphenylmethylcarbinol, (ii) subjecting said solution to an acid catalyzed displacement reaction for a sufficient period of time and under suitable conditions of temperature and pressure to convert substantially all of said carbinol to 4-hydroxyphenylmethylcarbinol methyl ether in solution, (iii) polymerizing said ether containing solution in the presence of a suitable acid catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form a novolak type polymer. New compositions of matter which comprise the derivatized poly(4-hydroxystyrene) prepared in the above manner and which have application in the electronic chemicals market such as in a photoresist composition, and in other areas such as in varnishes, printing inks, epoxy resins, copying paper, tackifiers for rubber, crude oil separators, and the like.
摘要翻译：一种制备具有酚醛清漆型结构的衍生化聚（4-羟基苯乙烯）的方法，其包括以下步骤：（i）提供含4-羟基苯基甲基甲醇的甲醇溶液，（ii）使所述溶液进行酸催化置换反应足够的时间的时间和温度和压力的合适条件下将基本上所有的甲醇转化为溶液中的4-羟基苯基甲基甲醇甲醚，（iii）在合适的酸催化剂存在下将所述含醚溶液聚合足够的时间和在合适的温度和压力条件形成酚醛清漆型聚合物。包含以上述方式制备并且适用于电子化学品市场的衍生聚（4-羟基苯乙烯）的物质的新组合物，例如在光致抗蚀剂组合物中，以及其它领域如清漆，印刷油墨，环氧树脂，复印纸，橡胶增粘剂，原油分离器等。

7. 发明授权

US07662538B2 Derivatized polyhydroxystyrenes (DPHS) with a novolak type structure and blocked DPHS (BDPHS) and processes for preparing the same 有权
标题翻译：具有酚醛清漆型结构并封闭DPHS（BDPHS）的衍生多羟基苯乙烯（DPHS）及其制备方法
公开(公告)号：US07662538B2
公开(公告)日：2010-02-16
申请号：US11250014
申请日：2005-10-13
申请人： Michael T. Sheehan , Edward G. Zey , Hiroshi Okazaki
发明人： Michael T. Sheehan , Edward G. Zey , Hiroshi Okazaki
IPC分类号： G03F7/039
CPC分类号： C08F8/00 , C08G61/04 , G03F7/0392 , G03F7/091 , C08F8/14 , C08F112/14
摘要： A process for preparing a blocked derivatized poly(4-hydroxystryrene)-DPHS having a novolak type structure which comprises the steps of (i) supplying a solution of methanol containing 4-hydroxyphenylmethylcarbinol, (ii) subjecting said solution to an acid catalyzed displacement reaction for a sufficient period of time and under suitable conditions of temperature and pressure to convert substantially all of said carbinol to 4-hydroxyphenylmethylcarbinol methyl ether in solution, (iii) polymerizing said ether containing solution in the presence of a suitable acid catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form a novolak type polymer; and (iv) reacting said polymer with a vinyl ether, a dialkyl dicarbonate, or a mixture of vinyl ether and a dialkyl dicarbonate to form the blocked DPHS. New compositions of matter which comprise the blocked derivatized poly(4-hydroxystyrene) prepared in the above manner and which have application in the electronic chemicals market such as in a photoresist composition and MEMS, and in other areas such as in varnishes, printing inks, epoxy resins, copying paper, tackifiers for rubber, crude oil separators, toner resins for photocopying, antireflective coatings, and the like.
摘要翻译：一种制备具有酚醛清漆型结构的封端衍生的聚（4-羟基苯乙烯）-DPHS的方法，其包括以下步骤：（i）提供含有4-羟基苯基甲基甲醇的甲醇溶液，（ii）使所述溶液进行酸催化置换反应在适当的温度和压力条件下，将基本上所有的所述甲醇转化为溶液中的4-羟基苯基甲基甲醇甲醚，（iii）在合适的酸催化剂存在下将所述含醚溶液聚合足够的时间的时间和在合适的温度和压力条件下形成酚醛清漆型聚合物; 和（iv）使所述聚合物与乙烯基醚，二碳酸二烷基酯或乙烯基醚和二碳酸二烷基酯的混合物反应以形成封端的DPHS。包含以上述方式制备并且适用于电子化学品市场的封闭的衍生化聚（4-羟基苯乙烯）的物质的新组合物，例如在光致抗蚀剂组合物和MEMS中，以及其它领域如清漆，印刷油墨，环氧树脂，复印纸，橡胶增粘剂，原油分离器，复印用调色剂树脂，抗反射涂料等。

8. 发明授权

US07632896B2 Derivatized novolak polyhydroxystyrene 有权
标题翻译：衍生的酚醛清漆多羟基苯乙烯
公开(公告)号：US07632896B2
公开(公告)日：2009-12-15
申请号：US12080871
申请日：2008-04-07
申请人： Michael T. Sheehan , Edward G. Zey
发明人： Michael T. Sheehan , Edward G. Zey
IPC分类号： C08G59/62 , C08G83/00
CPC分类号： C09D125/18 , C08G61/04 , C08G2261/312 , G03F7/023 , G03F7/038 , Y02P20/582
摘要： A process for preparing derivatized poly(4-hydroxystryrene) having a novolak type structure which comprises the steps of (i) supplying a solution of methanol containing 4-hydroxyphenylmethylcarbinol, (ii) subjecting said solution to an acid catalyzed displacement reaction for a sufficient period of time and under suitable conditions of temperature and pressure to convert substantially all of said carbinol to 4-hydroxyphenylmethylcarbinol methyl ether in solution, (iii) polymerizing said ether containing solution in the presence of a suitable acid catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form a novolak type polymer. New compositions of matter which comprise the derivatized poly(4-hydroxystyrene) prepared in the above manner and which have application in the electronic chemicals market such as in a photoresist composition, and in other areas such as in varnishes, printing inks, epoxy resins, copying paper, tackifiers for rubber, crude oil separators, and the like.
摘要翻译：一种制备具有酚醛清漆型结构的衍生化聚（4-羟基苯乙烯）的方法，其包括以下步骤：（i）提供含4-羟基苯基甲基甲醇的甲醇溶液，（ii）使所述溶液进行酸催化置换反应足够的时间的时间和温度和压力的合适条件下将基本上所有的甲醇转化为溶液中的4-羟基苯基甲基甲醇甲醚，（iii）在合适的酸催化剂存在下将所述含醚溶液聚合足够的时间和在合适的温度和压力条件形成酚醛清漆型聚合物。包含以上述方式制备并且适用于电子化学品市场的衍生聚（4-羟基苯乙烯）的物质的新组合物，例如在光致抗蚀剂组合物中，以及其它领域如清漆，印刷油墨，环氧树脂，复印纸，橡胶增粘剂，原油分离器等。

9. 发明授权

US06759483B2 Preparation of homo-, co- and terpolymers of substituted styrenes 有权
标题翻译：取代苯乙烯的均聚物，共聚物和三元共聚物的制备
公开(公告)号：US06759483B2
公开(公告)日：2004-07-06
申请号：US10126719
申请日：2002-04-19
申请人： Michael T. Sheehan , James R. Sounik
发明人： Michael T. Sheehan , James R. Sounik
IPC分类号： C08F21602
CPC分类号： C08F6/04 , C08F6/02 , C08F8/14 , C08F2800/10 , C08F2800/20 , G03F7/0045 , G03F7/039 , C08L25/18 , C08L25/00 , C08F212/14
摘要： A novel one-pot cost efficient process for the preparation of homo-, co- and terpolymers of p-hydroxystyrene or substituted p-hydroxystyrene and alkyl acrylates. The process involves polymerization of esters of p-hydroxystyrene (or its substituted analogs), alkyl acrylate monomers and/or one or more of ethylenically unsaturated monomers in an alcohol solvent in the presence of a free radical initiator. The reaction mixture containing the so formed polymer is subjected to transesterification conditions using a catalytic amount of catalyst to result in co- and/or terpolymers of p-hydroxystyrene without cleavage of the alkyl ester in the acrylate repeat unit, and then removing the catalyst from the system. Preferred embodiments include homopolymers of p-hydroxystyrene, copolymer of p-hydroxystyrene and tert-butyl acrylate and terpolymer of p-hydroxystyrene, tert-butyl acrylate and styrene. These polymers have a wide variety of applications including as photoresists in microelectronics industry.
摘要翻译：用于制备对羟基苯乙烯或取代的对羟基苯乙烯和丙烯酸烷基酯的均聚物，共聚物和三元共聚物的新型一锅成本有效的方法。该方法包括在自由基引发剂存在下，在醇溶剂中聚合对羟基苯乙烯（或其取代的类似物），丙烯酸烷基酯单体和/或一种或多种烯属不饱和单体的酯。将含有如此形成的聚合物的反应混合物用催化量的催化剂进行酯交换反应，得到对羟基苯乙烯的共聚和/或三元共聚物而不裂解丙烯酸酯重复单元中的烷基酯，然后将催化剂从系统。优选的实施方案包括对羟基苯乙烯的均聚物，对羟基苯乙烯和丙烯酸叔丁酯的共聚物和对羟基苯乙烯，丙烯酸叔丁酯和苯乙烯的三元共聚物。这些聚合物具有广泛的应用，包括微电子工业中的光致抗蚀剂。

10. 发明授权

US5347049A Processes for preparing diamino compounds 失效
标题翻译：制备二氨基化合物的方法
公开(公告)号：US5347049A
公开(公告)日：1994-09-13
申请号：US179796
申请日：1994-01-11
申请人： Michael T. Sheehan , James R. Sounik , Bret F. Hann , William W. Wilkison, III
发明人： Michael T. Sheehan , James R. Sounik , Bret F. Hann , William W. Wilkison, III
IPC分类号： C07C45/70 , C07C45/71 , C07C49/825 , C07C49/84 , C07C217/58 , C08G18/32 , C08G18/50 , C08G65/26 , C08G65/325 , C07C209/26
CPC分类号： C08G65/3255 , C07C217/58 , C07C45/70 , C07C45/71 , C07C49/825 , C07C49/84 , C08G18/324 , C08G18/329 , C08G18/5024 , C08G65/2603 , C08G65/2612
摘要： Di-amines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1, R.sub.2, R.sub.5, and R.sub.6 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH; R.sub.3 =R.sub.4, and R.sub.3 and R.sub.4 are from the group --CH.sub.2 CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3) H--CH.sub.2 --; and the diasteromeric salts thereof.
摘要翻译：公开了赋形剂如聚脲和聚氨酯的赋链链延伸活性的二胺，其具有以下通式：其中n为0-1000; R 1，R 2，R 5和R 6各自独立地选自H，-CH 3，-CH 2 CH 3，-CH 2 OH和-CH 2 -CH 2 -OH; R3 = R4，R3和R4来自基团-CH2CH2-; -CH2-C（CH3）H-; 和-C（CH 3）H-CH 2 - ; 及其非对映盐。

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