Abstract: A method for producing an oxidized cyclic phenol sulfide which comprises the step of oxidizing a cyclic phenol sulfide of the following formula (1) as a raw material: wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 8, in a solvent(s) other than a halogenated hydrocarbon in an amount of 2 or more and less than 10 parts by weight per 1 part by weight of the cyclic phenol sulfide, with an oxidizing agent(s) to obtain an oxidized cyclic phenol sulfide of the following formula (2): wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 8, and n is 1 or 2.

Abstract: The present invention provides a positive-charge control agent containing, as an active substance(s), one or two or more rhodanine compounds represented by the following formula (1). wherein R1 represents a hydrogen atom, etc.; R2 represents a hydrogen atom, etc.; and R3 to R7, which may be identical to or different from each other, represent a hydrogen atom, a cyano group, a trifluoromethyl group, a nitro group, etc. R2 to R7 may be joined to each other to form a ring. V, W, X, Y and Z represent a carbon atom or a nitrogen atom and 0 to 3 of V, W, X, Y and Z are nitrogen atoms, with the proviso that at least one of R3 to R7 is a linear or branched alkyl group having 1 to 4 carbon atoms substituted with three or more fluorine atoms etc.

Abstract: The present invention provides a charge control agent containing, as an active substance(s), one or two or more rhodanine compounds represented by the following formula (1). where R1 represents a hydrogen atom, etc.; R2 represents a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent, a substituted or unsubstituted heterocyclic group, etc.; R3 to R7, which may be identical to or different from each other, represent a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, a linear or branched alkyloxy group having 1 to 20 carbon atoms which may have a substituent, etc., and may be joined to each other to form a ring; and V, W, X, Y and Z represent a carbon atom or a nitrogen atom, and 0 to 3 of any of V, W, X, Y and Z are nitrogen atoms which do not have the substituents of R3 to R7.

Abstract: A method for producing an oxidized cyclic phenol sulfide which comprises the step of oxidizing a cyclic phenol sulfide of the following formula (1) as a raw material: wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 8, in a solvent(s) other than a halogenated hydrocarbon in an amount of 2 or more and less than 10 parts by weight per 1 part by weight of the cyclic phenol sulfide, with an oxidizing agent(s) to obtain an oxidized cyclic phenol sulfide of the following formula (2): wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 8, and n is 1 or 2.

Abstract: The object of the present invention is, in methods for producing cyclic phenol sulfides, to provide methods for producing a number of more macrocyclic products, which comprise the steps of producing a mixture of cyclic phenol sulfides from an inexpensive raw material in one step without inducing the reduction in yield of a cyclic quatromer; and easily separating and purifying a single component from the mixture of cyclic phenol sulfides. The present invention discloses methods for producing a cyclic phenol sulfide which comprises the step of reacting a phenol compound as a raw material, in a one-step reaction, with 1.7 to 2.5 molar equivalent of sulfur and 0.25 to 0.75 molar equivalent of an alkali metal reagent per 1 mol of the phenol compound to obtain a mixture of cyclic phenol sulfide wherein m=4 and at least one kind(s) of cyclic phenol sulfide wherein m=5 to 9, or each separate cyclic phenol sulfide comprised in the mixture.

Abstract: A method for producing an oxidized cyclic phenol sulfide which comprises the step of oxidizing a cyclic phenol sulfide of the following formula (1) as a raw material: wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 8, in a solvent(s) other than a halogenated hydrocarbon in an amount of 2 or more and less than 10 parts by weight per 1 part by weight of the cyclic phenol sulfide, with an oxidizing agent(s) to obtain an oxidized cyclic phenol sulfide of the following formula (2): wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 8, and n is 1 or 2.

Abstract: The present invention discloses a method for continuously producing an oxidized cyclic phenol sulfide which comprises the continuous steps of reacting a para-alkyl phenol compound as a raw material with 1.7 to 2.5 molar equivalent of sulfur and 0.25 to 0.75 molar equivalent of an alkali metal reagent per 1 mol of the phenol compound (the first step); and oxidizing a cyclic phenol sulfide of the formula (2) produced by the above reaction with an oxidizing agent(s) in the same reactor as that of the first step and without taking the cyclic phenol sulfide out of the reactor: wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 8, to obtain an oxidized cyclic phenol sulfide of the formula (3) (the second step): wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 8, and n is 1 or 2.

Abstract: A negatively charged polymerized toner having high charging performance, which comprises a charge control agent particularly useful for color toners and polymerized toners, the charge control agent comprising a cyclic phenol sulfide as an active ingredient, which speeds up charging risetime, has a high charge amount and charging characteristics particularly excellent in environmental stability, and is safe since it does not have any problem with the waste regulations.

Abstract: The present invention provides a process for producing N,N?-carbonyldiimidazole, comprising: reacting phosgene, diphosgene, or triphosgene with imidazole in an inert solvent to produce N,N?-carbonyldiimidazole; to imidazole hydrochloride yielded as a by-product in the above step, adding a gaseous or liquid basic compound represented by the below-shown general formula (1) in an inert solvent to conduct neutralization reaction; and circulating the imidazole thus generated to use it as a starting material for N,N?-carbonyldiimidazole production. In the general formula (1), R1, R2, and R3 each independently represents a hydrogen atom, a methyl group, or an ethyl group. The CDI produced by the production process of the invention is a compound useful in the fields of synthesis of pharmaceutical agents, synthesis of agricultural chemicals, peptide synthesis, and the like, e.g.

Abstract: The present invention discloses a mixed cyclic phenol sulfide which is a mixture of the cyclic phenol sulfide wherein m is 8 and the cyclic phenol sulfide wherein m is an integer other than 8, the cyclic phenol sulfide being represented by the following formula (1): wherein R is a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 9; or a cyclic phenol sulfide of formula (1) wherein m is 8. The present invention also discloses a charge control agent which comprises the above sulfide(s) as the active ingredient; and a toner which comprises the charge control agent, a coloring agent and a binder resin. This charge control agent is particularly useful for color toners, and it speeds up charging risetime, and has a high charge amount and charging characteristics excellent in the environmental stability. Further, the charge control agent is safe since it does not have any problem with the waste regulations.

Abstract: The present invention discloses a charge control agent which comprises a metal compound of a cyclic phenol sulfide of the following formula (1) as an active ingredient: wherein at least one of several Y is a metal atom. The present invention also discloses a toner which comprises one or more kinds of said metal compound, a coloring agent and a binder resin. The charge control agent of the present invention overcomes disadvantages such as lack of sharpness of first copied images and instability of the quality of the copied images in continuously copying, and it is those applicable to recent high speed printers, which have a quick charging rise time, an excellent environmental stability since the charge amount thereof less varies depending on the changes of temperature and humidity, and a high frictional charge amount. In addition, by using said charge control agent, a toner having a negative electric with high charging performance can be provided.

Abstract: The present invention discloses a method for continuously producing an oxidized cyclic phenol sulfide which comprises the continuous steps of reacting a para-alkyl phenol compound as a raw material with 1.7 to 2.5 molar equivalent of sulfur and 0.25 to 0.75 molar equivalent of an alkali metal reagent per 1 mol of the phenol compound (the first step); and oxidizing a cyclic phenol sulfide of the formula (2) produced by the above reaction with an oxidizing agent(s) in the same reactor as that of the first step and without taking the cyclic phenol sulfide out of the reactor; wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 8, to obtain an oxidized cyclic phenol sulfide of the formula (3) (the second step): wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 8, and n is 1 or 2.

Abstract: The present invention discloses an oxidized mixed cyclic phenol sulfide which is a mixture of the oxidized cyclic phenol sulfide wherein m is 8 and the oxidized cyclic phenol sulfide wherein m is an integer other than 8, the oxidized cyclic phenol sulfide being represented by the following formula (1): wherein R is a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 9, and n is 1 or 2; or an oxidized cyclic phenol sulfide of formula (1) wherein m is 8. The present invention also discloses a charge control agent which comprises the above sulfide(s) as the active ingredient; and a toner which comprises the charge control agent, a coloring agent and a binder resin. This charge control agent is particularly useful for color toners, and it speeds up charging risetime, and has a high charge amount and charging characteristics excellent in environmental stability. Further, the charge control agent is safe since it does not have any problem with the waste regulations.

Abstract: The present invention discloses an oxidized mixed cyclic phenol sulfide which is a mixture of the oxidized cyclic phenol sulfide wherein m is 8 and the oxidized cyclic phenol sulfide wherein m is an integer other than 8, the oxidized cyclic phenol sulfide being represented by the following formula (1): wherein R is a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 9, and n is 1 or 2; or an oxidized cyclic phenol sulfide of formula (1) wherein m is 8. The present invention also discloses a charge control agent which comprises the above sulfide(s) as the active ingredient; and a toner which comprises the charge control agent, a coloring agent and a binder resin. This charge control agent is particularly useful for color toners, and it speeds up charging risetime, and has a high charge amount and charging characteristics excellent in environmental stability. Further, the charge control agent is safe since it does not have any problem with the waste regulations.

Abstract: A method for producing an oxidized cyclic phenol sulfide which comprises the step of oxidizing a cyclic phenol sulfide of the following formula (1) as a raw material: wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 8, in a solvent(s) other than a halogenated hydrocarbon in an amount of 2 or more and less than 10 parts by weight per 1 part by weight of the cyclic phenol sulfide, with an oxidizing agent(s) to obtain an oxidized cyclic phenol sulfide of the following formula (2): wherein R represents a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 8, and n is 1 or 2.

Abstract: The object of the present invention is, in methods for producing cyclic phenol sulfides, to provide methods for producing a number of more macrocyclic products, which comprise the steps of producing a mixture of cyclic phenol sulfides from an inexpensive raw material in one step without inducing the reduction in yield of a cyclic quatromer; and easily separating and purifying a single component from the mixture of cyclic phenol sulfides. The present invention discloses methods for producing a cyclic phenol sulfide which comprises the step of reacting a phenol compound as a raw material, in a one-step reaction, with 1.7 to 2.5 molar equivalent of sulfur and 0.25 to 0.75 molar equivalent of an alkali metal reagent per 1 mol of the phenol compound to obtain a mixture of cyclic phenol sulfide wherein m=4 and at least one kind(s) of cyclic phenol sulfide wherein m=5 to 9, or each separate cyclic phenol sulfide comprised in the mixture.

Abstract: The present invention discloses an oxidized mixed cyclic phenol sulfide which is a mixture of the oxidized cyclic phenol sulfide wherein m is 8 and the oxidized cyclic phenol sulfide wherein m is an integer other than 8, the oxidized cyclic phenol sulfide being represented by the following formula (1): wherein R is a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 9, and n is 1 or 2; or an oxidized cyclic phenol sulfide of formula (1) wherein m is 8. The present invention also discloses a charge control agent which comprises the above sulfide(s) as the active ingredient; and a toner which comprises the charge control agent, a coloring agent and a binder resin. This charge control agent is particularly useful for color toners, and it speeds up charging risetime, and has a high charge amount and charging characteristics excellent in environmental stability. Further, the charge control agent is safe since it does not have any problem with the waste regulations.

Abstract: The present invention provides a process for producing N,N?-carbonyldiimidazole, comprising: reacting phosgene, diphosgene, or triphosgene with imidazole in an inert solvent to produce N,N?-carbonyldiimidazole; to imidazole hydrochloride yielded as a by-product in the above step, adding a gaseous or liquid basic compound represented by the below-shown general formula (1) in an inert solvent to conduct neutralization reaction; and circulating the imidazole thus generated to use it as a starting material for N,N?-carbonyldiimidazole production. In the general formula (1), R1, R2, and R3 each independently represents a hydrogen atom, a methyl group, or an ethyl group. The CDI produced by the production process of the invention is a compound useful in the fields of synthesis of pharmaceutical agents, synthesis of agricultural chemicals, peptide synthesis, and the like, e.g.

Abstract: The present invention discloses an oxidized mixed cyclic phenol sulfide which is a mixture of the oxidized cyclic phenol sulfide wherein in is 8 and the oxidized cyclic phenol sulfide wherein m is an integer other than 8, the oxidized cyclic phenol sulfide being represented by the following formula (1): wherein R is a straight or branched alkyl group having 1 to 6 carbon atoms, m is an integer from 4 to 9, and n is 1 or 2; or an oxidized cyclic phenol sulfide of formula (1) wherein m is 8. The present invention also discloses a charge control agent which comprises the above sulfide(s) as the active ingredient; and a toner which comprises the charge control agent, a coloring agent and a binder resin. This charge control agent is particularly useful for color toners, and it speeds up charging risetime, and has a high charge amount and charging characteristics excellent in environmental stability. Further, the charge control agent is safe since it does not have any problem with the waste regulations.

Abstract: The present invention discloses a mixed cyclic phenol sulfide which is a mixture of the cyclic phenol sulfide wherein m is 8 and the cyclic phenol sulfide wherein m is an integer other than 8, the cyclic phenol sulfide being represented by the following formula (1): wherein R is a straight or branched alkyl group having 1 to 6 carbon atoms, and m is an integer from 4 to 9; or a cyclic phenol sulfide of formula (1) wherein m is 8. The present invention also discloses a charge control agent which comprises the above sulfide(s) as the active ingredient; and a toner which comprises the charge control agent, a coloring agent and a binder resin. This charge control agent is particularly useful for color toners, and it speeds up charging risetime, and has a high charge amount and charging characteristics excellent in the environmental stability. Further, the charge control agent is safe since it does not have any problem with the waste regulations.