US 6,756,485 B2 · Process for preparing a monoazo metal complex salt compound for charge control agent and toner for developing electrostatic images · patentgrep

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Abstract

Charge control agent comprising a metal complex salt compound of Formula (I) containing substantially no monoazo compound constituting the ligand thereof, toner containing the charge control agent, and process for manufacturing a metal complex salt compound of Formula (I), which comprises a metallizing reaction for metallizing a monoazo compound of Formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound, in which metallizing reaction a monohydric or dihydric alcohol is used as a reaction-promoting solvent: R: alkyl (C4 to 12); Y: halogen or alkyl (C 1 to 5); p and q: number of monoazo compounds coordinated to the metal M; p: 1, 2, 3 or 4; q: 0, 1, 2 or 3; p+q: 1 to 6; L1 and L2 is —O—; one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion; M is iron, nickel, aluminum, titanium or zirconium; (Mx+)m: m number of metals of atomic valence x; m: 1 to 4; x: 2 or more; Z−: the negative charge in the parentheses; (A+)n is a hydrogen ion or an alkali metal ion, n=Z;

Claims38

Dependent claims

A process for preparing a metal complex salt compound of formula (I):

wherein
R is a normal or branched alkyl group having 4-12 carbon atoms;
Y is a halogen atom or a normal or branched alkyl group having 1-5 carbon atoms;
each of p and q shows the number of corresponding monoazo compounds coordinated to the metal M;
such that p is 1, 2, 3 or 4;
q is 0, 1, 2 or 3;
and the sum of p+q is an integer of 1-6;
each of L1 and L2 is —O—;
one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion;
M is iron, nickel, aluminum, titanium or zirconium;
(Mx+)m represents an m number of metals of atomic valence x;
such that m is an integer of 1-4;
and x is an integer of 2 or more;
Z− is the negative charge in the parentheses;
and (A+)n is a hydrogen ion or an alkali metal ion;
and n=Z;
which comprises a step of metallizing a monoazo compound of formula (II):
wherein R and Y are the same as defined above;
with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound in a metallizing reaction in which a monohydric alcohol is used as solvent, whereby to obtain a metal complex salt compound of not less than about 90% purity.

16 more elements

A process for preparing a metal complex salt compound of formula (I):

wherein
R is a normal or branched alkyl group having 4-12 carbon atoms;
Y is a halogen atom or a normal or branched alkyl group having 1-5 carbon atoms;
each of p and q shows the number of corresponding monoazo compounds coordinated to the metal M;
such that p is 1, 2, 3 or 4;
q is 0, 1, 2 or 3;
and the sum of p+q is an integer of 1-6;
each of L1 and L2 is —O—;
one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion;
M is iron, nickel, aluminum, titanium or zirconium;
(Mx+)m represents an m number of metals of atomic valence x;
such that m is an integer of 1-4;
and x is an integer of 2 or more;
Z− is the negative charge in the parentheses;
and (A+)n is a hydrogen ion or an alkali metal ion;
and n=Z;
which comprises an initial step of diazotizing coupling reaction to produce a monoazo compound of formula (II):
wherein R and Y are the same as defined above;
in which a corresponding 4-Y-2-aminophenol wherein Y is the same as defined above is diazotized to the corresponding diazonium salt and the diazonium salt is in turn coupled with a corresponding 6-R-2-naphthol wherein R is the same as defined above to form the monoazo compound of formula (II);
in which a monohydric alcohol is used as solvent in the diazotizing coupling reaction;
which comprises a subsequent step of metallizing the resulting monoazo compound of formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound in a metallizing reaction in which a monohydric alcohol is used as solvent, whereby to obtain a metal complex salt compound of not less than about 90% purity;
and
after the metallizing reaction is carried out, the process comprises a further step of cooling the reaction mixture and separating the resulting precipitated metal complex salt compound from the cooled reaction mixture wherein, after the further step of cooling the reaction mixture and separating the precipitated metal complex salt compound, the attendant remaining monohydric alcohol is recovered in the form of an azeotrope with water and at least a portion of the azeotrope is recycled for reusing the monohydric alcohol of the azeotrope in the metallizing reaction.

20 more elements

A process for preparing a metal complex salt compound of formula (I):

wherein
R is a normal or branched alkyl group having 4-12 carbon atoms;
Y is a halogen atom or a normal or branched alkyl group having 1-5 carbon atoms;
each of p and q shows the number of corresponding monoazo compounds coordinated to the metal M;
such that p is 1, 2, 3 or 4;
q is 0, 1, 2 or 3;
and the sum of p+q is an integer of 1-6;
each of L1 and L2 is —O—;
one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion;
M is iron, nickel, aluminum, titanium or zirconium;
(Mx+)m represents an m number of metals of atomic valence x;
such that m is an integer of 1-4;
and x is an integer of 2 or more;
Z− is the negative charge in the parentheses;
and (A+)n is a hydrogen ion or an alkali metal ion;
and n=Z;
which comprises an initial step of diazotizing coupling reaction to produce a monoazo compound of formula (II):
wherein R and Y are the same as defined above;
in which a corresponding 4-Y-2-aminophenol wherein Y is the same as defined above is diazotized to the corresponding diazonium salt and the diazonium salt is in turn coupled with a corresponding 6-R-2-naphthol wherein R is the same as defined above to form the monoazo compound of formula (II);
in which a monohydric alcohol is used as solvent in the diazotizing coupling reaction;
and
which comprises a subsequent step of metallizing the resulting monoazo compound of formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound in a metallizing reaction in which a monohydric alcohol is used as solvent, whereby to obtain a metal complex salt compound of not less than about 90% purity wherein, after the initial step of diazotizing coupling reaction is carried out, the process comprises an intermediate step of separating the resulting precipitated monoazo compound from the reaction mixture, recovering the attendant remaining monohydric alcohol in the form of an azeotrope with water, and recycling at least a portion of the azeotrope for reusing the monohydric alcohol of the azeotrope in the metallizing reaction.

19 more elements

A process for preparing a metal complex salt compound of formula (I):

wherein
R is a normal or branched alkyl group having 4-12 carbon atoms;
Y is a halogen atom or a normal or branched alkyl group having 1-5 carbon atoms;
each of p and q shows the number of corresponding monoazo compounds coordinated to the metal M;
such that p is 1, 2, 3 or 4;
q is 0, 1, 2 or 3;
and the sum of p+q is an integer of 1-6;
each of L1 and L2 is —O—;
one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion;
M is iron, nickel, aluminum, titanium or zirconium;
(Mx+)m represents an m number of metals of atomic valence x;
such that m is an integer of 1-4;
and x is an integer of 2 or more;
Z− is the negative charge in the parentheses;
and (A+)n is a hydrogen ion or an alkali metal ion;
and n=Z;
which comprises an initial step of diazotizing coupling reaction to produce a monoazo compound of formula (II):
wherein R and Y are the same as defined above;
in which a corresponding 4-Y-2-aminophenol wherein Y is the same as defined above is diazotized to the corresponding diazonium salt and the diazonium salt is in turn coupled with a corresponding 6-R-2-naphthol wherein R is the same as defined above to form the monoazo compound of formula (II);
in which a monohydric alcohol is used as solvent in the diazotizing coupling reaction;
and
which comprises a subsequent step of metallizing the resulting monoazo compound of formula (II) with iron, nickel, aluminum, titanium or zirconium to produce a metal complex salt compound in a metallizing reaction in which a monohydric alcohol is used as solvent, whereby to obtain a metal complex salt compound of not less than about 90% purity wherein, after the initial step of diazotizing coupling reaction is carried out, the process comprises an intermediate step of separating the resulting precipitated monoazo compound from the reaction mixture, recovering the attendant remaining monohydric alcohol in the form of an azeotrope with water, and recycling at least a portion of the azeotrope for reusing the monohydric alcohol of the azeotrope in the diazotizing coupling reaction.

19 more elements

A process for preparing a metal complex salt compound of formula (I):

wherein
R is a normal or branched alkyl group having 4-12 carbon atoms;
Y is a halogen atom or a normal or branched alkyl group having 1-5 carbon atoms;
each of p and q shows the number of corresponding monoazo compounds coordinated to the metal M;
such that p is 1, 2, 3 or 4;
q is 0, 1, 2 or 3;
and the sum of p+q is an integer of 1-6;
each of L1 and L2 is —O—;
one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion;
M is iron, nickel, aluminum, titanium or zirconium;
(Mx+)m represents an m number of metals of atomic valence x;
such that m is an integer of 1-4;
and x is an integer of 2 or more;
Z− is the negative charge in the parentheses;
and (A+)n is a hydrogen ion or an alkali metal ion;
and n=Z;
which comprises metallizing a monoazo compound of formula (II):
wherein R and Y are the same as defined above;
with a metallizing agent containing a metal M as defined above in a monohydric alcohol as solvent, sufficiently to react substantially completely the monoazo compound of formula (II) and to produce a reaction mixture containing substantially no unreacted monoazo compound and containing the metal complex salt compound of formula (I) in high yield and in a high purity of not less than about 90%.

16 more elements

A process for preparing a metal complex salt compound of formula (I):

wherein
R is a normal or branched alkyl group having 4-12 carbon atoms;
Y is a halogen atom or a normal or branched alkyl group having 1-5 carbon atoms;
each of p and q shows the number of corresponding monoazo compounds coordinated to the metal M;
such that p is 1, 2, 3 or 4;
q is 0, 1, 2 or 3;
and the sum of p+q is an integer of 1-6;
each of L1 and L2 is —O—;
one of L3 and L4 is —O—, while the other is an —OH group or an —O− ion;
M is iron, nickel, aluminum, titanium or zirconium;
(Mx+)m represents an m number of metals of atomic valence x;
such that m is an integer of 1-4;
and x is an integer of 2 or more;
Z− is the negative charge in the parentheses;
and (A+)n is a hydrogen ion or an alkali metal ion;
and n=Z;
which comprises preparing a monoazo compound of formula (II):
wherein R and Y are the same as defined above;
by a diazotizing coupling reaction in which a corresponding 4-Y-2-aminophenol wherein Y is the same as defined above is diazotized to the corresponding diazonium salt and the diazonium salt is in turn coupled with a corresponding 6-R-2-naphthol wherein R is the same as defined above to form the monoazo compound of formula (II), the diazotizing coupling reaction being carried out in a monohydric alcohol as solvent;
recovering the monoazo compound of formula (II) from the resulting reaction mixture of the diazotizing coupling reaction, and recovering the attendant remaining monohydric alcohol in the form of an azeotrope with water;
metallizing the recovered monoazo compound of formula (II) with a metallizing agent containing a metal M as defined above in a monohydric alcohol as solvent, sufficiently to react substantially completely the monoazo compound of formula (II) and to produce a reaction mixture containing substantially no unreacted monoazo compound and containing the metal complex salt compound of formula (I) in high yield and in a high purity of not less than about 90%;
recovering the metal complex salt compound of formula (I) as a precipitate from the resulting reaction mixture of the metallizing reaction, and recovering the attendant remaining monohydric alcohol in the form of an azeotrope with water;
and
recycling at least a portion of the azeotrope from at least one of (a) the diazotizing coupling reaction, or (b) the metallizing reaction for reusing the monohydric alcohol of the azeotrope as solvent in at least one of (a) the diazotizing coupling reaction, or (b) the metallizing reaction.

21 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/364,443Filed 11 Feb 2003 · division
Priority: JP 11-20025014 Jul 1999
Published: US 2003/0187234 A12 Oct 2003
Granted: 29 Jun 2004
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

Family

Application09/615,199Parent of this division · filed 13 Jul 2000
US 2003/0187234 A1Pre-grant publication · published 2 Oct 2003
US 6,548,648 B1Parent of this division
US 6,756,485 B2This patent

From the US filing history. Foreign family members aren’t listed.

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