Patents by Inventor Ralph Dammel

Ralph Dammel has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5843319
    Abstract: A process for producing a solution of a basic or non-basic sulfonium compound (A) of formulae II-V: ##STR1## wherein R.sup.5, R.sup.6 and R.sup.7 each independently represent a C.sub.1 -C.sub.18 alkyl, aryl or heteroaryl group or an aryl group mono-, di- or tri-substituted with an alkyl, an alkylaryl, an aryl, a halogen, an alkoxy, a phenoxy, a thiophenol, a phenylsulfonyl or a phenylsulphenyl;Y represents (CH.sub.2).sub.n (wherein n is 0 or 1), O or S;R.sup.8 and R.sup.9 represent a C.sub.1 -C.sub.4 alkyl, alkoxy or a halogen;R.sup.10 and R.sup.11 represent a C.sub.1 -C.sub.4 alkyl, alkoxy or a halogen;n is 5 or 6; andX.sub.2.sup.- represents a basic anion having a pK.sub.B value of -3 to +5; comprising the steps of:(a) dissolving a sulfonium salt (B) in a metal-ion free polar or non-polar solvent to form a solution, said sulfonium salt (B) being selected from said formulae II-V, wherein R.sup.5 to R.sup.11, Y and n of said sulfonium salt (B) have the sane meaning as above and X.sub.2.sup.
    Type: Grant
    Filed: July 29, 1997
    Date of Patent: December 1, 1998
    Assignee: Hoechst Japan Limited
    Inventors: Klaus Juergen Przybilla, Takanori Kudo, Seiya Masuda, Yoshiaki Kinoshita, Natsumi Suehiro, Munirathna Padmanaban, Hiroshi Okazaki, Hajime Endo, Ralph Dammel, Georg Pawlowski
  • Patent number: 5807947
    Abstract: A polymer of (a) an unsubstituted 4-hydroxystyrene monomer and (b) a substituted 4-hydroxystyrene monomer of the formula ##STR1## wherein A, B, C, and D are independently H or C.sub.1 to C.sub.4 alkyl wherein at least one of B and D is C.sub.1 to C.sub.4 alkyl; and wherein said copolymer has a molecular weight of from about 800 to about 100,000; and wherein the mol ratio of monomer (a) to monomer (b) ranges from about 3:1 to about 1:3.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: September 15, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Richard Vicari, Douglas J. Gordon, William D. Hinsberg, Dennis R. McKean, Carlton G. Willson, Ralph Dammel
  • Patent number: 5614351
    Abstract: A radiation-curable mixture is disclosed which contains a compound which forms an acid under the action of high-energy radiation, and contains an acid-curable compound, wherein the compound which forms an acid contains aliphatically bound halogen (chlorine or bromine) and has a pK.sub.a value of less than about 12. A radiation-curable recording material and a process for recording high-energy radiation using the material are also disclosed. The mixture, and in particular the recording material produced therefrom, has relatively high sensitivity and improved resolution and, in addition, does not exhibit image fogging after development.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: March 25, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralph Dammel, Juergen Lingnau, Georg Pawlowski, Juergen Theis
  • Patent number: 5541036
    Abstract: A negative photoresist composition comprising:(A) a compound represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.2 which are different from each other represent a hydrogen atom or a group represented by the following formula (II): ##STR2## (B) an alkoxymethylated melamine, and (C) a novolak resin.The photoresist composition has resolution below submicron, and can form resist patterns with an ideal rectangular profile.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: July 30, 1996
    Assignee: Hoechst Japan Limited
    Inventors: Akihiko Igawa, Masato Nishikawa, Georg Pawlowski, Ralph Dammel
  • Patent number: 5525453
    Abstract: A novel positive-working radiation-sensitive mixture having a high sensitivity to radiation in a short-wavelength UV region is provided which can be developed in an aqueous alkaline solution, has a stable acid latent image and is used for the production of a semiconductor. The mixture comprises, as indispensable components, a) a binder insoluble in water but soluble in an aqueous alkaline solution, b) a compound having at least one bond cleavable with an acid, c) a compound capable of producing an acid upon radiation, and d.sub.1) a basic ammonium compound or d.sub.2) a basic sulfonium compound.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: June 11, 1996
    Assignee: Hoechst Japan Limited
    Inventors: Klaus J. Przybilla, Takanori Kudo, Seiya Masuda, Yoshiaki Kinoshita, Natumi Suehiro, Munirathna Padmanaban, Hiroshi Okazaki, Hajime Endo, Ralph Dammel, Georg Pawlowski
  • Patent number: 5424166
    Abstract: A negative-working radiation-sensitive mixture which comprisesa) a compound, which forms a strong acid on irradiation, of the general formula ##STR1## in which R.sup.1 is a radical R.sup.2 --SO.sub.2 -- or R.sup.3 --C(O)-- andR.sup.2 and R.sup.3 independently of one another are an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical,b) a compound containing at least two reactive groups which can be crosslinked by an acid andc) a water-insoluble binder which is soluble or at least swellable in aqueous-alkaline solutions, is described.The radiation-sensitive mixture according to the invention is distinguished by a high sensitivity over a wide spectral range. It likewise exhibits a high heat stability and forms no corrosive photolysis products on exposure to light.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: June 13, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Winfried Meier
  • Patent number: 5403697
    Abstract: A positive radiation-sensitive mixture is disclosed comprising a compound which forms an acid under the action of high-energy radiation and an acid-cleavable compound, wherein the compound which forms an acid contains aromatically bound chlorine or bromine and has a pK.sub.a value of less than about 12 or is a derivative of a compound having such a pK.sub.a value. The mixture and the recording material produced therefrom have a relatively high-sensitivity and improved resolution and, in addition, exhibit no scumming after development.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: April 4, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Friedrich Doessel, Ralph Dammel, Juergen Lingnau
  • Patent number: 5401608
    Abstract: A negative-working radiation-sensitive mixture containinga) a compound which contains at least one --CBr.sub.3 group bound to an atom not linked in turn to a hydrogen atom,b) an alkoxymethylated melamine andc) a water-insoluble polymeric binder which is soluble, or at least swellable, in aqueous alkaline solutions and contains phenolic OH groups,wherein(1) the mixture has an absorption of <0.4 .mu.m.sup.-1 at 248 nm,(2) the CBr.sub.3 group of the compound a) is bound to the sulfur atom of a sulfonyl group and the compound a) is contained in the mixture in an amount of 0.2 to 10% by weight, based on the total amount of the components b) and c),(3) the ratio by mass of the components b) and c) is between 50:50 and 5:95 and(4) the component c) is a homopolymer or copolymer of hydroxystyrene or a derivative thereof, the homopolymer or copolymer having a removal rate of 200 to 3,000 nm/min at 21.degree. C. in an aqueous alkaline developer containing 2.
    Type: Grant
    Filed: July 23, 1992
    Date of Patent: March 28, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Winfried Meier, Walter Spiess, Klaus-Juergen Przybilla
  • Patent number: 5346806
    Abstract: Ligomeric sulfonic acid derivatives having repeating units of the formula I ##STR1## in which R.sup.1 is an alkyl, haloalkyl or aryl radical,R.sup.2 is a hydrogen atom, an alkyl, alkenyl or aryl radical or the group (R.sup.1 --SO.sub.2 --O--).sub.n X--,R.sup.3 is a cycloalkylenedialkyl, cycloalkenylenedialkyl, arylenedialkyl, heteroarylenedialkyl group, alkylene, alkenylene, alkynylene, cycloalkylene or arylene group,X is an alkylene, cycloalkylene or arylene group Y is O, S, CO, CO--O, SO.sub.2, SO.sub.2 --O, NR.sup.4, CO--NH, O--CO--NR.sup.5, NH--CO--NR.sup.5 or NR.sup.5 --CO--O,Z is O, CO--NR.sup.6, O--CO--NR.sup.6 or NH--CO--NR.sup.6,R.sup.4 is an acyl radical,R.sup.5 is a hydrogen atom or an alkyl-, cycloalkyl, alkenyl, alkynyl or aryl radical,R.sup.6 is an alkyl, cycloalkyl, alkenyl, alkynyl or aryl radical,k is 0, 1, 2, 3 or 4,m is an integer greater than 1 andn is 1, 2 or 3,generate sulfonic acids under irradiation and are cleavable by the latter.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: September 13, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Charlotte Eckes
  • Patent number: 5346804
    Abstract: A radiation-sensitive mixture which contains compounds of the formula I which generate under irradiation sulfonic acids and are cleavable by the latter ##STR1## in which R.sup.1 is an unsubstituted or substituted alkyl, fluorinated alkyl, perfluoroalkyl or aryl radical,R.sup.2 is a hydrogen atom, an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical, (R.sup.1 --SO.sub.2 --O--).sub.n X--, or R.sub.3 O--,R.sup.3 and R.sup.4 are identical or different and are unsubstituted or substituted alkyl, cycloalkylalkyl, cycloalkenylalkyl or aralkyl radicals, in which 1 to 3 aliphatic CH.sub.2 or CH groups are optionally replaced by one or more of NR.sup.5, O, S, CO, CO--O, CO--NH, O--CO--NH, CO--NH--CO, NH--CO--NH, SO.sub.2, SO.sub.2 --O or SO.sub.2 --NH, or unsubstituted or substituted alkenyl, alkynyl, cycloalkyl or cycloalkenyl radicals, or R.sup.3 and R.sup.4 are mutually linked to form an unsubstituted or substituted heterocyclic ring,R.sup.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: September 13, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Geog Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Charlotte Eckes
  • Patent number: 5342727
    Abstract: A copolymer of (a) an unsubstituted 4-hydroxystyrene monomer and (b) a substituted 4-hydroxystyrene monomer of the formula ##STR1## wherein A, B, C, and D are independently H or C.sub.1 to C.sub.4 alkyl and wherein at least one of B and D is C.sub.1 to C.sub.4 alkyl; and wherein said copolymer has a molecular weight of from about 800 to about 100,000; and wherein the mol ratio of monomer (a) to monomer (b) ranges from about 3:1 to about 1:3.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: August 30, 1994
    Assignees: Hoechst Celanese Corp., IBM Corp.
    Inventors: Richard Vicari, Douglas J. Gordon, William D. Hinsberg, Dennis R. McKean, Carlton G. Willson, Ralph Dammel
  • Patent number: 5340682
    Abstract: A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents:a) an .alpha.-carbonyl-.alpha.-sulfonyl-diazomethane, which forms a strong acid on irradiation, of the general formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, denote an alkyl-, cycloalkyl-, aryl- or heteroaryl radicalb) a compound having at least one C--O--C or C--O--Si bond which can be cleaved by acid, andc) a water-insoluble binder which is soluble or at least swellable in aqueous-alkaline solutions.The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photoylsis products on exposure to light.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: August 23, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Joachim Merrem, Juergen Lingnau, Ralph Dammel, Horst Roeschert
  • Patent number: 5338641
    Abstract: A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents:a) an .alpha.,.alpha.-bis(sulfonyl)diazomethane, which forms a strong acid on irradiation, of the general formula ##STR1## in which R is an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical,b) a compound having at least one C--O--C or C--O--Si--bond which can be cleaved by acid, andc) a water-insoluble binder which is soluble or at least swellable in aqueous alkaline solutions.The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photolysis products on exposure to light.
    Type: Grant
    Filed: March 4, 1993
    Date of Patent: August 16, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Joachim Merrem, Juergen Lingnau, Ralph Dammel, Horst Roeschert
  • Patent number: 5326826
    Abstract: Radiation-sensitive polymers, a mixture containing these radiation-sensitive polymers as binder, and a process for the preparation of the radiation-sensitive polymer binders are disclosed. A positive radiation-sensitive recording material containing the radiation-sensitive polymer is also disclosed.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: July 5, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Hans-Joachim Merrem, Georg Pawlowski, Juergen Fuchs, Ralph Dammel
  • Patent number: 5302488
    Abstract: A radiation-sensitive polymer and a mixture containing this radiation-sensitive polymer as a binder are disclosed. A process for the preparation of the radiation-sensitive polymer binder and a positive-working radiation-sensitive recording material which is prepared using the radiation-sensitive mixture are also disclosed.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: April 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Hans-Joachim Merrem, Georg Pawlowski, Juergen Fuchs, Ralph Dammel
  • Patent number: 5286602
    Abstract: Compounds having repeating units of the formula I ##STR1## in which R.sup.1 is an alkylene, cycloalkylene, alkenylene, alkynylene, or arylenebisalkyl group, in which one or more aliphatic CH.sub.2 groups may be replaced by oxygen or sulfur atoms,R.sup.2 is an alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, aryl, aralkyl or aryloxyalkyl radical,R.sup.3 is an alkyl or aryl radical,X is --CO--, --O--CO-- or --NH--CO--, andn is an integer greater than 1, especially from 3 to 50.are cleavable by acid and, in combination with photolytic acid donors and alkali-soluble binders, are constituents of positive-working mixtures which are used especially in recording materials for UV radiation and high-energy radiation. The materials are distinguished by a high resolution in conjunction with high image contrast.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: February 15, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Horst Roeschert, Walter Spiess, Ralph Dammel
  • Patent number: 5256517
    Abstract: A positive-working radiation-sensitive mixture is described which essentially contains a photoactive component and a water-insoluble binder which is soluble, or at least swellable, in aqueous alkaline solution, wherein a compound is used, as photoactive component, which contains .alpha.-diazo-.beta.-keto ester units and sulfonate units of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having 4 to 20 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by N or NH groups and/or contain keto groups,X is an unsubstituted or substituted aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by the groups --NR.sup.3 --, --C(O)--0--, --C(O)--NR.sup.3 --, ##STR2## --NR.sup.3 --C(O)--NR.sup.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: October 26, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel, Walter Spiess
  • Patent number: 5247096
    Abstract: A process is described for preparing N-tert-butoxycarbonylmaleimide from maleimide and di-tert-butyl dicarbonate which comprises reacting maleimide with di-tert-butyl dicarbonate in the presence of a basic compound of the general formula I ##STR1## in which A represents the ring members required to complete a five- or six-membered saturated ring and R is (C.sub.1 -C.sub.4)alkyl, in one stage to give the end product.In a preferred embodiment, the compound of the general formula I is N-methylmorpholine.The product is useful as a monomer for polymerization, with the styrene copolymers being particularly suitable for chemically reinforced radiation-sensitive mixtures.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: September 21, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Ralph Dammel, Georg Pawlowski, Klaus-Juergen Przybilla
  • Patent number: 5234791
    Abstract: A radiation-curable composition which comprises a compound that forms an acid under the action of high-energy radiation and an acid-hardening substance, wherein the compound forming an acid contains aromatically linked chlorine or bromine and has a pK.sub.a value below 12. The composition and the recording material prepared therefrom display increased sensitivity, improved resolution and a high etch resistance after development.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: August 10, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralph Dammel, Karl-Friedrich Doessel, Juergen Lingnau, Juergen Theis
  • Patent number: 5217843
    Abstract: A positive radiation-sensitive mixture is disclosed which contains a compound which forms an acid under the action of high-energy radiation, and an acid-cleavable compound, wherein the compound which forms an acid contains aliphatically bound halogen (chlorine or bromine) and has a pK.sub.a value of less than about 12 or is a derivative of a compound having such a pK.sub.a value which can be converted into the free compound by acid catalysis. A positive recording material and a process for recording high-energy radiation using the material are also disclosed. The mixture, and in particular the recording material produced therefrom, has relatively high sensitivity and improved resolution and, in addition, does not exhibit image fogging after development.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: June 8, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralph Dammel, Juergen Lingnau, Georg Pawlowski, Juergen Theis