Patents by Inventor Hans-Helmut Friedrich

Hans-Helmut Friedrich 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: 4863621
    Abstract: Compositions containing a lubricant, a hydraulic fluid or a metal-working fluid and at least one compound of the formula I ##STR1## in which R, R.sup.4, R.sup.5 and n are as defined in claim 1, are described. The compounds of the formula I are suitable for use as anti-wear agents and as extreme-pressure additives for lubricants, hydraulic fluids and metal-working fluids. Novel compounds of the formula I are also described.
    Type: Grant
    Filed: January 9, 1987
    Date of Patent: September 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4835310
    Abstract: 1. Compounds of the formula I ##STR1## in which n is a number from 1 to 100, Y is --N(R.sup.3)--, --S-- or --S--R.sup.4 --S--, R.sup.1 is C.sub.2 -C.sub.8 -alkylene, which can be interrupted by 1 to 3 ether oxygen atoms, R.sup.2 is hydrogen, unsubstituted or hydroxyl-monosubstituted to -pentasubstituted C.sub.1 -C.sub.8 -alkyl, which can be interrupted one or more times by --O--, --S-- or --N(R.sup.5)-- as long as R.sup.2 is not unsubstituted C.sub.1 -C.sub.8 -alkyl when Y is --S-- and n is 1, R.sup.3 is hydrogen unsubstituted or hydroxylmonosubstituted to -pentasubstituted C.sub.1 -C.sub.8 -alkyl, which can be interrupted one or more times by --O--, --N(R.sup.5)-- or --S--, R.sup.4 is unsubstituted or OH-monosubstituted or -polysubstituted C.sub.2 -C.sub.8 -alkylene, which can be interrupted one or more times by --O-- or --S--, are very highly suitable for use as high pressure and antiwear additives for polar functional fluids.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: May 30, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Rainer Schneider, Hans-Helmut Friedrich
  • Patent number: 4830770
    Abstract: The invention relates to compositions comprising a lubricant or a hydraulic fluid and at least one compound of the general formula ##STR1## wherein n is 2, 3 or 4, X is --S--, --O--, --O--CO-- or --CH.sub.2 --, R.sup.1 is C.sub.1 -C.sub.22 alkyl, C.sub.5 -C.sub.6 cycloalkyl or phenyl, and R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.4 alkyl which is substituted by an --OH group, or a group of the formula --CH.sub.2 --CH(OH)--CH.sub.2 --X--R.sup.1, wherein X and R.sup.1 have the given meanings, and to novel compounds of the formula indicated above. The glucamine derivatives of formula I are especially suitable for use as antiwear agents and as extreme pressure additives for mineral and synthetic lubricant oils and hydraulic fluids, and also as amphipolar ligands for imparting lipophilic properties to intrinsically hydrophilic metal salts, metal oxides, metal hydroxides and to protic acids. The complex compounds so obtained of the formulaM.sub.n.sup.m. X.sub.m.sup.n. pY.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: May 16, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4808755
    Abstract: The invention relates to compositions comprising a lubricant or a hydraulic fluid and at least one compound of the general formula ##STR1## wherein n is 2, 3 or 4, X is --S--, --O--, --O--CO-- or --CH.sub.2 --, R.sup.1 is C.sub.1 -C.sub.22 alkyl, C.sub.5 -C.sub.6 cycloalkyl or phenyl, and R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.4 alkyl which is substituted by an --OH group, or a group of the formula --CH.sub.2 --CH(OH)--CH.sub.2 --X--R.sup.1, wherein X and R.sup.1 have the given meanings, and to novel compounds of the formula indicated above. The glucamine derivatives of formula I are especially suitable for use as antiwear agents and as extreme pressure additives for mineral and synthetic lubricant oils and hydraulic fluids, and also as amphipolar ligands for imparting lipophilic properties to intrinsically hydrophilic metal salts, metal oxides, metal hydroxides and to protic acids. The complex compounds so obtained of the formulaM.sub.n.sup.m.X.sub.m.sup.n.pY.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: February 28, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4737300
    Abstract: The invention relates to material containing aldosemarcaptals of the formula I ##STR1## wherein n can be an integer from 2 to 6, and wherein R.sup.1 and R.sup.2 are identical or different, and in each case are C.sub.1 -C.sub.18 -alkyl, which is unsubstituted, substituted or interrupted by --O-- or --S--, or are --(CH.sub.2).sub.r --CO--N(C.sub.1 -C.sub.17 -alkyl).sub.2, r being 1 or 2, or are phenyl, benzyl or --(CH.sub.2).sub.r --CO--O--R.sup.3, in which r can be 1 or 2 and R.sup.3 is an alkali metal or C.sub.1 -C.sub.14 -alkyl; also wherein R.sup.1 and R.sup.2 are --CH.sub.2 --CH(OH)--R.sup.4, in which R.sup.4 is hydrogen, or C.sub.1 -C.sub.16 -alkyl, unsubstituted or substituted by --OH, or --CH.sub.2 --Y--(C.sub.1 -C.sub.15 -alkyl), in which Y is --O-- or --S--; or wherein R.sup.1 and R.sup.2 together form --(CH.sub.2).sub.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4732691
    Abstract: The invention relates to compositions comprising a lubricant or a hydraulic fluid and at least one compound of the general formula ##STR1## wherein n is 2, 3 or 4, X is --S--, --O--, --O--CO-- or --CH.sub.2 --, R.sup.1 is C.sub.1 -C.sub.22 alkyl, C.sub.5 -C.sub.6 cycloalkyl or phenyl, and R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.4 alkyl which is substituted by an --OH group, or a group of the formula --CH.sub.2 --CH(OH)--CH.sub.2 --X--R.sup.1, wherein X and R.sup.1 have the given meanings, and to novel compounds of the formula indicated above. The glucamine derivatives of formula I are especially suitable for use as antiwear agents and as extreme pressure additives for mineral and synthetic lubricant oils and hydraulic fluids, and also as amphipolar ligands for imparting lipophilic properties to intrinsically hydrophilic metal salts, metal oxides, metal hydroxides and to protic acids. The complex compounds so obtained of the formulaM.sub.n.sup.m.X.sub.m.sup.n.pY.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: March 22, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4689162
    Abstract: Compounds of the formula I ##STR1## wherein R and R.sup.1 are identical or different, and are cyclohexyl or a radical ##STR2## in which R.sup.2 is hydrogen or C.sub.1 -C.sub.12 -alkyl, and R.sup.3 and R.sup.4 independently of one another are each C.sub.1 -C.sub.12 -alkyl, and the radicals R.sup.2, R.sup.3 and R.sup.4 together contain 3-20 C atoms.These compounds are suitable as high-pressure and anti-wear additives for lubricants and hydraulic fluids.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: August 25, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Klaus Muller, Hans-Helmut Friedrich
  • Patent number: 4425278
    Abstract: A complex compound of a metal salt or metalloid salt and an ansolvo-acid or proton-acid, of the general formula IM.sub.n.sup.m.X.sub.m.sup.n.pY.qZ (I)in which M is a m-valent cation of a metal or metalloid, a metal-oxy or metal-dioxy cation or a hydrogen atom, X is a n-valent anion of a n-basic inorganic proton-acid or of a n-basic organic acid selected from the group of the aliphatic and cycloaliphatic carboxylic acids with up to 8 C atoms, which can be substituted by halogen and/or hydroxyl groups, the aromatic monocarboxylic, dicarboxylic and tricarboxylic acids, which may be substituted by hydroxyl, halogen and/or nitro groups, the organic oxyacids of phosphorus and sulphur, the organic thioacids of phosphorus, and the mercaptans, the inorganic or organic acid having a pK.sub.a value of at most 15.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: January 10, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4404408
    Abstract: Metal or metalloid salts, ansolvo-acids and proton-acids can be so complexed with 1,2,3-triols, glycerol ethers or glycerol thioethers containing at least 6 C atoms in the molecule that they are in the form of compositions which are soluble in organic solvents, especially non-polar, aprotic solvents, such as hydrocarbons. These stable compositions display an outstanding anti-static action and, because of their spectrum of properties, are especially suitable for imparting anti-static characteristics to polymers, lubricants, fuels and also solvents based on hydrocarbons.
    Type: Grant
    Filed: September 7, 1977
    Date of Patent: September 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4385147
    Abstract: Chlorine-containing thermoplastics which contain, as a stabilizer, a compound of the formula I ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are as defined in the description.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: May 24, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Jurgen Bussing, Hans-Helmut Friedrich
  • Patent number: 4369277
    Abstract: Chlorine-containing thermoplastics containing a pyrrole of one of the formulae I to V ##STR1## the substituents being as defined in the patent specification. The pyrroles are used to stabilize chlorine-containing thermoplastics.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: January 18, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Jurgen Bussing, Hans-Helmut Friedrich
  • Patent number: 4369276
    Abstract: Chlorine-containing thermoplastics, containing a pyrrole of the formula I ##STR1## in which R.sub.1 is hydrogen, alkyl, cycloalkyl, aryl, alkoxycarbonylmethyl, free or esterified .alpha.-hydroxyalkyl, free or esterified .alpha.-hydroxycycloalkylmethyl, free or esterified .alpha.-hydroxyaralkyl, alkoxymethyl, alkylthiomethyl, aryloxymethyl, arylthiomethyl, cycloalkoxymethyl, cycloalkylthiomethyl, aralkoxymethyl, aralkylthiomethyl, alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, aralkoxy, arylalkylthio, aryloxy, arylthic, halogen, mercapto, mercaptomethyl or hydroxyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, free or esterified .alpha.-hydroxyalkyl, in which the alkyl moiety together with R.sub.1 can be alkylene, or free or esterified .alpha.-hydroxycycloalkylmethyl, free or esterified .alpha.
    Type: Grant
    Filed: May 26, 1981
    Date of Patent: January 18, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Jurgen Bussing, Hans-Helmut Friedrich
  • Patent number: 4336148
    Abstract: A complex compound of a metal salt or metalloid salt and an ansolvo-acid or proton-acid, of the general formula IM.sub.n.sup.m.X.sub.m.sup.n.pY.qZ (I)in which M is a m-valent cation of a metal or metalloid, a metal-oxy or metal-dioxy cation or a hydrogen atom, X is a n-valent anion of a n-basic inorganic proton-acid or of a n-basic organic acid selected from the group of the aliphatic and cycloaliphatic carboxylic acids with up to 8 C atoms, which can be substituted by halogen and/or hydroxyl groups, the aromatic monocarboxylic, dicarboxylic and tricarboxylic acids, which may be substituted by hydroxyl, halogen and/or nitro groups, the organic oxyacids of phosphorus and sulphur, the organic thioacids of phosphorus, and the mercaptans, the inorganic or organic acid having a pK.sub.a value of at most 15.
    Type: Grant
    Filed: August 30, 1978
    Date of Patent: June 22, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4290940
    Abstract: Chlorine-containing thermoplastics, containing a pyrrole of the formula I ##STR1## in which R.sub.1 is hydrogen, alkyl, cycloalkyl, aryl, alkoxycarbonylmethyl, free or esterified .alpha.-hydroxyalkyl, free or esterified .alpha.-hydroxycycloalkylmethyl, free or esterified .alpha.-hydroxyaralkyl, alkoxymethyl, alkylthiomethyl, aryloxymethyl, arylthiomethyl, cycloalkoxymethyl, cycloalkylthiomethyl, aralkoxymethyl, aralkylthiomethyl, alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, aralkoxy, arylalkylthio, aryloxy, arylthio, halogen, mercapto, mercaptomethyl or hydroxyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, free or esterified .alpha.-hydroxyalkyl, in which the alkyl moiety together with R.sub.1 can be alkylene, or free or esterified .alpha.-hydroxycycloalkylmethyl, free or esterified .alpha.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: September 22, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Jurgen Bussing, Hans-Helmut Friedrich
  • Patent number: 4245125
    Abstract: Compounds of the formula IA.multidot.m B (I)whereinA is a compound of the formula II or III ##STR1## m is a rational number between 0.1 and 4.0, and B is H.sub.2 O.sub.2, N.sub.2 H.sub.4 or NH.sub.2 OH, andR.sub.1 is an unsubstituted or substituted aliphatic or aromatic hydrocarbon radical which has 3-30 C atoms and which can be interrupted by oxygen or sulfur atoms,R.sub.2 is hydrogen or C.sub.1 -C.sub.30 alkyl,X is --O-- or --SO.sub.2 -- and, in the case where B is N.sub.2 H.sub.4 or NH.sub.2 OH, also --S-- or --SO--,Y is the direct bond, ##STR2## Q is --CH.sub.2, --CH(OH)--CH.sub.2 -- or --CH(CH.sub.2 --OH)--, and n is 1, 2, 3, 4, 5, 6, 7 or 8.
    Type: Grant
    Filed: May 10, 1979
    Date of Patent: January 13, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 3988378
    Abstract: Reaction products of mercaptans, ethylene oxide and/or propylene oxide with glycidol are effective antistatic agents when added to thermoplastics, and often also act as processing stabilisers.
    Type: Grant
    Filed: July 31, 1975
    Date of Patent: October 26, 1976
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich, Helmut Linhart
  • Patent number: 3936422
    Abstract: Reaction products of mercaptans, ethylene oxide and/or propylene oxide with glycidol are effective antistatic agents when added to thermoplastics, and often also act as processing stabilisers.
    Type: Grant
    Filed: January 7, 1975
    Date of Patent: February 3, 1976
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich, Helmut Linhart
  • Patent number: 3933877
    Abstract: New triorganotin and triorganolead compounds which are hydrophilic and difficultly volatile are used as biocides.
    Type: Grant
    Filed: July 31, 1974
    Date of Patent: January 20, 1976
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Otto Wirth, Hans Joachim Lorenz, Hans-Helmut Friedrich
  • Patent number: 3931262
    Abstract: New triorganotin compounds which are hydrophilic and difficultly volatile are used as biocides.
    Type: Grant
    Filed: July 31, 1974
    Date of Patent: January 6, 1976
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Otto Wirth, Hans Joachim Lorenz, Hans-Helmut Friedrich