Patent number: 8604232
Abstract: The invention relates to method for producing mono amino-functionalised dialkylphosphonic acids esters and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, the salt or ester thereof (II), b) the alkylphosphonous acid, the salt or ester thereof (II) produced above is reacted with an allylamine of formula (V) in the presence of a catalyst B to give mono amino-functionalised dialkylphosphinic acid derivatives (III) where, R1, R2, R3, R4, R5, R6, R7, R8, R9 independently=amongst others, H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X?H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base and Y=a mineral acid, a carboxylic acid, a Lewis acid or organic acid, where n=a whole or fractional number from 0 to 4, catalyst A is a transition metal and/or transition metal compound a
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
December 10, 2013
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20130190432
Abstract: A novel flame retardant-stabilizer combination for thermoplastic polymers, comprising as component A 20 to 99% by weight of a dialkylphosphinic salt of the formula (I) and/or of a diphosphinic salt of the formula (II) and/or polymers thereof in which R1, R2 are the same or different and are each C1-C6-alkyl, linear or branched; R3 is C1-C10-alkylene, linear or branched, C6-C10-arylene, C7-C20-alkylarylene or C7-C20-arylalkylene; M is Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base; m is 1 to 4; n is 1 to 4; x is 1 to 4, as component B 1 to 80% by weight of a salt of the phosphorous acid with the general formula (III) [HP(?O)O2]2?Mm+ (III) in which M is Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na and/or K and m is 1 to 4, as component C 0 to 30% by weight of a nitrogen-containing synergist and/or of a phosphorus/nitrogen flame retardant, as component D 0 to 10% by weight of a zinc salt and/or of a basic or amphoteric oxide, hydroxide, carbo
Type:
Application
Filed:
September 30, 2011
Publication date:
July 25, 2013
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Werner Krause, Harald Bauer, Martin Sicken, Sebastian Hoerold, Wolfgang Wanzke, Elke Schlosser
Publication number: 20130131239
Abstract: The invention relates to a method for producing mixtures of alkylphosphonous acid and dialkylphosphinic acid salts, characterised in that a) a phosphinic acid source (I) is reacted with olefins (II) in the presence of a catalyst A to obtain a mixture of alkylphosphonous acid (III) and dialkylphosphinic acid (IV) or salts or esters thereof, and b) the thus obtained mixture of alkylphosphonous acid (III) and dialkylphosphinic acid (IV) or the salts or esters thereof is reacted with metal compounds of Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base to obtain the corresponding mixtures of alkylphosphonous acid salt (V) and dialkylphosphinic acid salt (VI) of said metals and/or a nitrogen compound, (V) (VI), wherein Y represents Mg, Ca, AI, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na; K and/or a nitrogen compound and n represents ¼, ?, ½, 1.
Type:
Application
Filed:
April 20, 2011
Publication date:
May 23, 2013
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Sebastian Hoerold, Werner Krause, Martin Sicken
Publication number: 20130126805
Abstract: The invention relates to a method for producing alkylphosphonous acid salts, characterised in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salts or esters thereof (II), b) the thus obtained alkylphosphonous acid, the salts or esters thereof (II) are reacted with metal compounds of Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na, K and/or a protoned nitrogen base to obtain the corresponding alkylphosphonous acid salts (III) of said metals and/or a nitrogen compound, wherein R1, R2, R3, R4 are the same or different and independently of each other represent H, C1-C18-alkyl, C6-C18-aryl, C7-C18-arylalkyl, C7-C18-alkylaryl and Y represents Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na, K and/or a nitrogen compound and n represents ¼, ?, ½, 1 and the catalyst A is a transition metal and/or transition metal compound and/or catalyst systems which are composed of a transition metal and/or a tran
Type:
Application
Filed:
April 20, 2011
Publication date:
May 23, 2013
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20110281983
Abstract: The invention relates to a method for producing monohydroxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, b) the, obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with alkylene oxides of formula (V) in the presence of a catalyst B to obtain a monofunctionalized dialkylphosphinic acid derivative (III), wherein R1, R2, R3, R4, R5, R6, R7, R8 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, and X represents H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, catalyst A represents transition metals and/or transition metal compounds and/or catalyst systems composed of a transiti
Type:
Application
Filed:
October 6, 2009
Publication date:
November 17, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20110251315
Abstract: The invention relates to a method for producing monofunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester thereof, whereupon said alkylphosphonous acid, the salt or ester (II) thereof is reacted with compounds containing C?C, C?O, or C?N double bonds to obtain compounds of type (III), wherein R1, R2, R3, R4, R5, R6 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, X represents, inter alia, H, C1-C18-alkyl, C6-C18-aryl, and/or Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, and wherein A represents OH, NH2, NHR, NR2, or O—CO—R8, and W represents a mineral acid, carboxylic acid, Lewis acid, or organic acid, wherein n is a whole or a fractional number from 0 to 4, and catalyst A represents transition metals and/or transition metal compo
Type:
Application
Filed:
October 6, 2009
Publication date:
October 13, 2011
Applicant:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
Publication number: 20110251312
Abstract: The invention relates to a process for preparing ethylenedialkylphosphinic acids, ethylenedialkylphosphinic esters and ethylenedialkylphosphinic salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with an acetylenic compound (V) in the presence of a catalyst B, to give the ethylenedialkylphosphinic acid derivative (III), where R1, R2, R3, R4, R5, R6, R11, R12, R13 and R14 are identical or different and independently of one another inter alia are H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl and X is H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base, and the catalyst A comprises transition metals and/or transition-metal compounds and/or catalyst systems which are composed of
Type:
Application
Filed:
December 15, 2009
Publication date:
October 13, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20110251310
Abstract: The invention relates to addition compounds of a) alkylphosphonous acid derivatives of the formula A-P(?O)(OX)—H (I) in which A represents C2-C18-alkyl, C2-C18-alkylene, C6-C18-arylalkyl, C6-C18-arylalkyl, optionally substituted, and X represents H, C1-C18-alkyl, C6-C18-aryl, C6-C18-arylalkyl, C6-C18-alkylaryl, optionally substituted C2-C18-alkylene, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H and/or a protonated nitrogenous base, and b) diester-forming olefins of formula (II) in which R2, R4 are identical or different from each other and represent CO2H, CO2R5, R6—CO2H, R6—CO2R5 and R1, R3 are identical or different from each other and represent H, R5; or R1, R4 are identical or different from each other and represent CO2H, CO2R5, R6—CO2H, R6—CO2R5 and R2, R3 are identical or different from each other and represent H, R5; or R2, R4 are identical or different from each other and represent —CO—O—CO—, —CO—S—CO—, —CO—NR1—CO—, —CO—PR1—CO— and R1, R3 are identical or different f
Type:
Application
Filed:
October 6, 2009
Publication date:
October 13, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
Publication number: 20110251314
Abstract: The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R1, R2, R3, R4 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X and Y are identical or different from each other and independently represent H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition met
Type:
Application
Filed:
October 6, 2009
Publication date:
October 13, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20110245386
Abstract: The invention relates to a method for producing mixed-substituted dialkyiphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an olefin (IV) in the presence of a catalyst B to obtain the mixed-substituted dialkylphosphinic acid derivative (III), wherein R1, R2, R3, R4, R11, R12, R13, R14 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X represents H, C1-C18-alkyl, C8-C18-aryl, C6-C18-aralkyl, C8-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, catalyst A represents transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transit
Type:
Application
Filed:
October 6, 2009
Publication date:
October 6, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken