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    Composition containing naphthoquinone diazide sulfonic acid mixed esters and radiation-sensitive recording material prepared therewith
    2.
    发明授权
    Composition containing naphthoquinone diazide sulfonic acid mixed esters and radiation-sensitive recording material prepared therewith 失效
    含有萘醌二叠氮磺酸混合酯和用其制备的辐射敏感记录材料的组合物

    公开(公告)号：US5306595A

    公开(公告)日：1994-04-26

    申请号：US862603

    申请日：1992-04-01

    Applicant: Siegfried Scheler ,  Wolfgang Zahn ,  Axel Schmitt ,  Gerhard Buhr

    Inventor： Siegfried Scheler ,  Wolfgang Zahn ,  Axel Schmitt ,  Gerhard Buhr

    IPC: G03F7/00 ,  G03F7/022 ,  H01L21/027 ,  G03C1/52

    CPC classification number: G03F7/022

    Abstract: The present invention relates to a radiation-sensitive composition containing a resinous binder which is insoluble in water, but soluble or at least swellable in aqueous alkaline solutions, at least one radiation-sensitive compound and optionally a crosslinking agent. The radiation-sensitive compound is an ester composed of a) a compound containing 2 to 6 aromatic hydroxyl groups, b) a ring-substituted (o-naphthoquinone 2-diazide)-4-sulfonic acid (diazo compound D.sub.1) and c) an (o-naphthoquinone 2-diazide)-4- or -5-sulfonic acid which is not further substituted (diazo compound D.sub.2) and/or a non-radiation-sensitive organic acid (compound D.sub.0) , where the D.sub.1 :(D.sub.2 and/or D.sub.0) molar ratio is between about 0.1:1 and 30:1.

    Abstract translation: 本发明涉及一种含有树脂粘合剂的辐射敏感性组合物，其不溶于水，但在碱性水溶液，至少一种辐射敏感化合物和任选的交联剂中可溶或至少可溶胀。 辐射敏感性化合物是由a）含有2-6个芳族羟基的化合物，b）环取代的（邻 - 萘醌-2-二叠氮化物）-4-磺酸（重氮化合物D1）和c） （重氮化合物D2）和/或非辐射敏感性有机酸（化合物D0）的（邻 - 萘醌-2-二叠氮化物）-4-或-5-磺酸（化合物D0），其中D1：（D2和 /或D0）摩尔比为约0.1:1至30:1。

    Radiation-sensitive compounds, radiation-sensitive mixture prepared therewith and copying material
    3.
    发明授权
    Radiation-sensitive compounds, radiation-sensitive mixture prepared therewith and copying material 失效
    辐射敏感性化合物，其制备的辐射敏感性混合物和复制材料

    公开(公告)号：US5114816A

    公开(公告)日：1992-05-19

    申请号：US431221

    申请日：1989-11-03

    Applicant: Siegfried Scheler ,  Gerhard Buhr ,  Helmut Lenz ,  Klaus Bergmann ,  Herbert Siegel

    Inventor： Siegfried Scheler ,  Gerhard Buhr ,  Helmut Lenz ,  Klaus Bergmann ,  Herbert Siegel

    IPC: C07C309/26 ,  C07C309/52 ,  C07C309/73 ,  C07C311/37 ,  C07C323/66 ,  G03F7/022

    CPC classification number: G03F7/022 ,  C07C309/26 ,  C07C2101/16

    Abstract: The invention relates to novel radiation-sensitive compounds which are esters or amides of a 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid of the general formula ##STR1## in which R.sub.1 and R.sub.2 are identical or different and denote hydrogen, an alkyl group, an alkyl ether group or an alkyl thioether group whose carbon chains may be interrupted by ether oxygen atoms, an acylamino group, carboxylic acid ester group, sulfonic acid ester group or sulfonamide group,R.sub.1 and R.sub.2 not being hydrogen at the same time.The compounds are used as radiation-sensitive components in radiation-sensitive mixtures with which corresponding copying materials can be produced. The compounds have an absorption which is directed towards longer wavelengths matching the emission range of commercially available radiation sources. They also make it possible, in a reliable and practical manner, to carry out negativeworking image reversal processes.

    Abstract translation: 本发明涉及新的辐射敏感化合物，它们是通式为（I）的1,2-萘醌 - （2） - 二叠氮-4-磺酸的酯或酰胺，其中R 1和R 2相同或 不同的表示氢，烷基，烷基醚基或其碳链可被醚氧原子间隔的烷基硫醚基，酰氨基，羧酸酯基，磺酸酯基或磺酰胺基，R1和R2不是 同时是氢。 这些化合物用作辐射敏感性混合物中的辐射敏感组分，可以制备相应的复印材料。 这些化合物具有吸收，该吸收指向与市售辐射源的发射范围匹配的较长波长。 它们也使得以可靠和实际的方式实现负面的图像反转过程成为可能。

    Process for preparing substituted 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters and their use in a radiation-sensitive mixture
    5.
    发明授权
    Process for preparing substituted 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters and their use in a radiation-sensitive mixture 失效
    制备取代的1,2-萘醌 - （2） - 二硫代-4-磺酸酯的方法及其在辐射敏感性混合物中的用途

    公开(公告)号：US5082932A

    公开(公告)日：1992-01-21

    申请号：US431182

    申请日：1989-11-03

    Applicant: Herbert Siegel ,  Siegfried Scheler

    Inventor： Herbert Siegel ,  Siegfried Scheler

    IPC: C07C303/28 ,  C07C309/26 ,  C07C309/27 ,  C07C309/71 ,  G03F7/022

    CPC classification number: C07C309/26 ,  C07C309/27 ,  G03F7/022

    Abstract: The invention relates to a process for preparing 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters of the general formula I ##STR1## which are substituted in at least one of the positions 5, 6, 7 or 8 by R=halogen, alkoxy groups or alkoxycarbonyl groups and in which X denotes an aryl group. The process comprises steps in whicha) suitably substituted .beta.-naphthol is nitrosated,b) sulfonation with alkali hydrogensulfite and acid in position 4 and reduction are carried out,c) the naphthalenesulfonic acid derivative is oxidized,d) the 1,2-naphthoquinone-4-sulfonic acid formed is reacted with toluenesulfonohydrazide in an organic solvent at temperatures from 20.degree. to 100.degree. C.,e) the naphthoquinonediazide compound is converted with chlorosulfonic acid or chlorosulfonic acid/thionyl chloride into the sulfonyl chloride, and f) the sulfonyl chloride is condensed with a phenolic component, a purification of the respective intermediate product by reprecipitation or recrystallization being unnecessary.The process makes a simple technical procedure possible with good yield. The compounds prepared, in particular the 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters substituted by 6-alkoxycarbonyl groups or by 7-alkoxy groups, are used as radiation-sensitive components in radiation-sensitive mixtures.

    Abstract translation: 本发明涉及一种制备通式I（I）的1,2-萘醌 - （2） - 二叠氮-4-磺酸酯的方法，它在至少一个位置5,6， 7或8，其中R =卤素，烷氧基或烷氧基羰基，其中X表示芳基。 该方法包括以下步骤：a）适当取代的β-萘酚被亚硝化，b）用碱性亚硫酸氢盐和酸在4位磺化并进行还原，c）萘磺酸衍生物被氧化，d）1,2-萘醌 形成的4-磺酸与甲苯磺酰肼在有机溶剂中在20〜100℃的温度下反应，e）萘醌二叠氮化合物用氯磺酸或氯磺酸/亚硫酰氯转化成磺酰氯，f） 磺酰氯与酚成分缩合，通过再沉淀或重结晶不需要纯化各中间产物。 该过程使得一个简单的技术程序可以获得良好的收益。 制备的化合物，特别是被6-烷氧基羰基或7-烷氧基取代的1,2-萘醌 - （2） - 二叠氮-4-磺酸酯被用作辐射敏感性混合物中的辐射敏感成分。

    Diazotype materials with 2-hydroxy-naphthalene having sulfonamide substituent as coupler
    6.
    发明授权
    Diazotype materials with 2-hydroxy-naphthalene having sulfonamide substituent as coupler 失效
    具有磺酰胺取代基的2-羟基 - 萘的二嗪类材料作为偶联剂

    公开(公告)号：US4492749A

    公开(公告)日：1985-01-08

    申请号：US532302

    申请日：1983-09-15

    Applicant: Siegfried Scheler

    Inventor： Siegfried Scheler

    IPC: C09B29/15 ,  C07C67/00 ,  C07C301/00 ,  C07C311/29 ,  C07D295/18 ,  C07D295/26 ,  G03C1/58

    CPC classification number: C07D295/26 ,  G03C1/58

    Abstract: This invention relates to a derivative of 2-hydroxy-naphthalene of the general formula ##STR1## wherein A is ##STR2## and X is --OH or ##STR3## and R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are identical or different and are hydrogen, cycloalkyl having up to eight carbon atoms, which is optionally substituted by lower alkyl groups, aralkyl having up to 10 carbon atoms or aryl which is substituted by lower alkyl, lower alkoxy, halogenalkyl or alkyl-substituted amino groups or by halogen, or R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 in each case are, conjointly with the nitrogen atom to which they are attached, identical or different heterocyclic groups which are optionally substituted by lower alkyl.

    Abstract translation: 本发明涉及通式为“IMAGE”的2-羟基 - 萘的衍生物，其中A为X和X为-OH或R 1，且R 1，R 2，R 3和R 4为相同或不同的并且为氢 ，具有至多8个碳原子的环烷基，其任选被低级烷基取代，具有至多10个碳原子的芳烷基或被低级烷基，低级烷氧基，卤代烷基或烷基取代的氨基或卤素取代的芳基，或R1 并且R 2或R 3和R 4各自与它们所连接的氮原子结合，相同或不同的任选被低级烷基取代的杂环基。

    Two-component diazotype material
    7.
    发明授权
    Two-component diazotype material 失效
    双组分重氮型材料

    公开(公告)号：US4457997A

    公开(公告)日：1984-07-03

    申请号：US337277

    申请日：1982-01-05

    Applicant: Klaus Thoese ,  Hans-Dieter Frommeld ,  Siegfried Scheler

    Inventor： Klaus Thoese ,  Hans-Dieter Frommeld ,  Siegfried Scheler

    IPC: G03C1/52 ,  G03C1/60 ,  G03C1/54

    CPC classification number: G03C1/60 ,  Y10S430/11 ,  Y10S430/111 ,  Y10S430/112

    Abstract: A two-component diazotype material, composed of a support and a light-sensitive layer which is applied thereto and contains a polymeric binder, a diazonium salt, a coupler, an acid stabilizer and conventional additives, wherein the support is a biaxially oriented polyester film and the polymeric binder comprises a mixture of about 10-60 percent by weight of a polymer or copolymer of vinyl acetate, for example, a copolymer of vinyl acetate and crotonic acid, and about 40-90 percent by weight of a cellulose ester, such as cellulose acetopropionate, cellulose acetobutyrate, cellulose propionate or cellulose butyrate.

    Abstract translation: 双组分重氮型材料，由支撑体和施加于其上的光敏层组成并含有聚合物粘合剂，重氮盐，偶合剂，酸稳定剂和常规添加剂，其中载体是双轴取向的聚酯膜 聚合物粘合剂包括约10-60重量％的乙酸乙烯酯的聚合物或共聚物，例如乙酸乙烯酯和巴豆酸的共聚物和约40-90重量％的纤维素酯的混合物， 作为纤维素乙酰丙酸酯，乙酰丁酸纤维素，丙酸纤维素或丁酸纤维素。

    Light-sensitive mixture containing an 0-naphthoquinonediazide-sulfonic acid ester and recording material produced therewith wherein the 0-naphthoquinone diazides are partial esters
    9.
    发明授权
    Light-sensitive mixture containing an 0-naphthoquinonediazide-sulfonic acid ester and recording material produced therewith wherein the 0-naphthoquinone diazides are partial esters 失效
    含有O-萘醌二叠氮化物 - 磺酸酯的光敏混合物及其制备的记录材料，其中O-萘醌二叠氮化物为偏酯

    公开(公告)号：US5413899A

    公开(公告)日：1995-05-09

    申请号：US254500

    申请日：1994-06-06

    Applicant: Siegfried Scheler ,  Andreas Elsaesser ,  Gerhard Buhr ,  Klaus Bergmann ,  Wolfgang Zahn

    Inventor： Siegfried Scheler ,  Andreas Elsaesser ,  Gerhard Buhr ,  Klaus Bergmann ,  Wolfgang Zahn

    IPC: G03F7/00 ,  G03F7/022 ,  H01L21/027 ,  H01L21/30 ,  G03F7/021 ,  G03F7/30

    CPC classification number: G03F7/022

    Abstract: A light-sensitive mixture which contains a resinous binder which is insoluble in water but soluble or at least swellable in aqueous-alkaline solutions, and an o-naphthoquinonediazide-sulfonic acid ester, the o-naphthoquinonediazide-sulfonic acid ester being of the formula I ##STR1## in which R is hydrogen or an alkyl or aryl radical andR.sub.1 is hydrogen or a 1,2-naphthoquinone-2-diazide-4-sulfonyl, 1,2-naphthoquinone-2-diazide-5-sulfonyl or 7-methoxy-1,2-naphthoquinone-2-diazide-4-sulfonyl radical,and the number of the identical or different naphthoquinonediazide-sulfonyl radicals, defined as R.sub.1, in the molecule being 1 to 5; is useful in the preparation of light-sensitive resist materials. The resist material produced using the light-sensitive mixture has a high light sensitivity and very good developer resistance to alkaline developers and can be developed without any problems with aqueous, weakly alkaline solutions.

    Abstract translation: 含有不溶于水但在碱性水溶液中至少溶胀或至少可溶胀的树脂粘合剂和邻萘醌二叠氮化物 - 磺酸酯的光敏混合物，该邻萘醌二叠氮化物 - 磺酸酯为式I 其中R为氢或烷基或芳基，R1为氢或1,2-萘醌-2-重氮-4-磺酰基，1,2-萘醌-2-重氮基-5-磺酰基 或7-甲氧基-1,2-萘醌-2-二叠氮-4-磺酰基，分子中定义为R1的相同或不同的萘醌二叠氮基 - 磺酰基的数目为1〜5; 可用于制备光敏抗蚀剂材料。 使用感光性混合物制造的抗蚀剂材料具有高的光敏感性和对碱性显影剂非常好的显影剂抗性，并且可以在没有水性弱碱性溶液的问题的情况下开发。

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