公开(公告)号：US08232429B2

公开(公告)日：2012-07-31

申请号：US12503895

申请日：2009-07-16

Applicant: Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

Inventor： Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

IPC: C07C315/00

CPC classification number: C07D341/00

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 translation: 一种氧化环状苯酚硫化物的制造方法，其特征在于，将下述式（1）所示的环状苯酚硫化物氧化为原料，其中，R表示碳原子数1〜6的直链或支链烷基，m表示 4至8的整数，相对于每1重量份环状苯酚硫化物，其量为2重量份以上且小于10重量份的卤代烃类溶剂，以及氧化剂， 得到下述式（2）所示的氧化型环状苯酚硫化物：式中，R表示碳原子数1〜6的直链或支链烷基，m为4〜8的整数，n为1或2。

公开(公告)号：US20090275783A1

公开(公告)日：2009-11-05

申请号：US12503895

申请日：2009-07-16

Applicant: Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

Inventor： Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

IPC: C07C319/02

CPC classification number: C07D341/00

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 translation: 一种氧化环状苯酚硫化物的制造方法，其特征在于，将下述式（1）所示的环状苯酚硫化物氧化为原料，其中，R表示碳原子数1〜6的直链或支链烷基，m表示 4至8的整数，相对于每1重量份环状苯酚硫化物，其量为2重量份以上且小于10重量份的卤代烃类溶剂，以及氧化剂， 得到下述式（2）所示的氧化型环状苯酚硫化物：式中，R表示碳原子数1〜6的直链或支链烷基，m为4〜8的整数，n为1或2。

公开(公告)号：US20130177844A1

公开(公告)日：2013-07-11

申请号：US13822723

申请日：2011-11-22

Applicant: Masateru Yasumura ,  Masami Ito ,  Ikuo Kimura ,  Masaya Tojo ,  Kanae Hiraishi ,  Masaki Okubo

Inventor： Masateru Yasumura ,  Masami Ito ,  Ikuo Kimura ,  Masaya Tojo ,  Kanae Hiraishi ,  Masaki Okubo

IPC: G03G9/097

CPC classification number: G03G9/09766 ,  C07D277/20 ,  C07D277/36 ,  C07D417/06 ,  G03G9/0914 ,  G03G9/09758 ,  G03G9/09775

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 translation: 本发明提供一种含有下述式（1）表示的一种或两种以上的绕丹宁化合物作为活性物质的正电荷控制剂。 其中R1表示氢原子等; R2表示氢原子等; R 3〜R 7可以相同或不同，表示氢原子，氰基，三氟甲基，硝基等。R 2〜R 7可以相互结合形成环。 V，W，X，Y和Z表示碳原子或氮原子，V，W，X，Y和Z的0〜3为氮原子，条件是R3〜R7中的至少一个为直链或 被3个以上氟原子取代的碳原子数为1〜4的支链烷基等

公开(公告)号：US20120253054A1

公开(公告)日：2012-10-04

申请号：US13523420

申请日：2012-06-14

Applicant: Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

Inventor： Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

IPC: C07D341/00

CPC classification number: C07D341/00

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 translation: 一种氧化环状苯酚硫化物的制造方法，其特征在于，将下述式（1）所示的环状苯酚硫化物氧化为原料，其中，R表示碳原子数1〜6的直链或支链烷基，m表示 4至8的整数，相对于每1重量份环状苯酚硫化物，其量为2重量份以上且小于10重量份的卤代烃类溶剂，以及氧化剂， 得到下述式（2）所示的氧化型环状苯酚硫化物：式中，R表示碳原子数1〜6的直链或支链烷基，m为4〜8的整数，n为1或2。

公开(公告)号：US20110028737A1

公开(公告)日：2011-02-03

申请号：US12867207

申请日：2009-02-16

Applicant: Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito

Inventor： Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito

IPC: C07D341/00

CPC classification number: C07D341/00

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 translation: 本发明公开了一种连续生产氧化环状苯酚硫化物的方法，该方法包括以对数烷基酚化合物为原料与1.7〜2.5摩尔当量硫和0.25〜0.75摩尔当量碱金属试剂的连续步骤 每1mol酚化合物（第一步）; 和在与第一步骤相同的反应器中用氧化剂氧化由上述反应产生的式（2）的环状苯酚硫化物，而不将环状苯酚硫化物从反应器中取出; 其中R表示具有1至6个碳原子的直链或支链烷基，m为4至8的整数，以获得式（3）（第二步）的氧化环状苯酚硫化物：其中R表示直链 或碳原子数为1〜6的支链烷基，m为4〜8的整数，n为1或2。

公开(公告)号：US07820832B2

公开(公告)日：2010-10-26

申请号：US12481112

申请日：2009-06-09

Applicant: Masateru Yasumura ,  Masami Ito ,  Naohiro Tarumoto ,  Yoshikazu Aoki ,  Masafumi Umekawa ,  Masaki Okubo ,  Hideyuki Otsuka ,  Jun Watanabe

Inventor： Masateru Yasumura ,  Masami Ito ,  Naohiro Tarumoto ,  Yoshikazu Aoki ,  Masafumi Umekawa ,  Masaki Okubo ,  Hideyuki Otsuka ,  Jun Watanabe

IPC: C07D339/08

CPC classification number: G03G9/09775 ,  C07D341/00 ,  G03G9/08748 ,  G03G9/08771

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 translation: 本发明公开了氧化型环状苯酚硫化物，其为m为8的氧化型环状苯酚硫化物和m为8以外的整数的氧化型环状苯酚硫化物的混合物，氧化型环状苯酚硫化物由下式 （1）表示：其中R是具有1-6个碳原子的直链或支链烷基，m是4至9的整数，n是1或2; 或式（1）的氧化环状苯酚硫化物，其中m为8.本发明还公开了一种电荷控制剂，其包含上述硫化物作为活性成分; 以及包含电荷控制剂，着色剂和粘合剂树脂的调色剂。 该电荷控制剂对于彩色调色剂特别有用，并且其加速时间上升，并且具有高的电荷量和环境稳定性优良的充电特性。 此外，充电控制剂是安全的，因为废物规定没有任何问题。

公开(公告)号：US20090088575A1

公开(公告)日：2009-04-02

申请号：US11547524

申请日：2005-03-29

Applicant: Yoshikazu Aoki ,  Norimasa Yokoyama ,  Masateru Yasumura

Inventor： Yoshikazu Aoki ,  Norimasa Yokoyama ,  Masateru Yasumura

IPC: C07D403/06

CPC classification number: C07D233/54 ,  Y02P20/582

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., intermolecular condensation reactions, intramolecular condensation reactions for synthesizing N-carboxylic anhydrides, production of activated esters, and the like. The compound is especially suitable for use in applications where colorlessness is required.

Abstract translation: 本发明提供了制备N，N'-羰基二咪唑的方法，其包括：将光气，二光气或三光气与咪唑在惰性溶剂中反应以产生N，N'-羰基二咪唑; 在上述步骤中作为副产物产生的咪唑盐酸盐，在惰性溶剂中加入由下述通式（1）表示的气态或液态碱性化合物进行中和反应; 并使由此产生的咪唑循环使用其作为N，N'-羰基二咪唑生产的起始原料。 在通式（1）中，R 1，R 2和R 3各自独立地表示氢原子，甲基或乙基。 通过本发明的制造方法制备的CDI是可用于药物合成，农药合成，肽合成等领域的化合物，例如分子间缩合反应，用于合成N-羧酸酐的分子内缩合反应 ，活性酯的制备等。 该化合物特别适用于需要无色性的应用。

公开(公告)号：US20090035678A1

公开(公告)日：2009-02-05

申请号：US12240520

申请日：2008-09-29

Applicant: Masateru Yasumura ,  Masami Ito ,  Naohiro Tarumoto ,  Yoshikazu Aoki ,  Masafumi Umekawa ,  Masaki Okubo ,  Hideyuki Otsuka ,  Jun Watanabe

Inventor： Masateru Yasumura ,  Masami Ito ,  Naohiro Tarumoto ,  Yoshikazu Aoki ,  Masafumi Umekawa ,  Masaki Okubo ,  Hideyuki Otsuka ,  Jun Watanabe

IPC: G03G9/00 ,  C07D341/00

CPC classification number: G03G9/09733 ,  C07D341/00 ,  G03G9/08711 ,  G03G9/0904 ,  G03G9/09758 ,  G03G9/09775

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 translation: 本发明公开了一种混合环状苯酚硫化物，其中m为8的环状苯酚硫化物和m为8以外的环状苯酚硫化物的混合物，环状苯酚硫化物由下式（1）表示： 其中R是具有1至6个碳原子的直链或支链烷基，m是4至9的整数; 或式（1）的环状苯酚硫化物，其中m为8.本发明还公开了一种电荷控制剂，其包含上述硫化物作为活性成分; 以及包含电荷控制剂，着色剂和粘合剂树脂的调色剂。 该电荷控制剂对于彩色调色剂特别有用，并且其加速电荷上升时间，并且具有高的电荷量和环境稳定性优良的充电特性。 此外，充电控制剂是安全的，因为废物规定没有任何问题。

公开(公告)号：US08624065B2

公开(公告)日：2014-01-07

申请号：US13523420

申请日：2012-06-14

Applicant: Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

Inventor： Masateru Yasumura ,  Yoshikazu Aoki ,  Masami Ito ,  Masafumi Umekawa ,  Naohiro Tarumoto

IPC: C07C315/00

CPC classification number: C07D341/00

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 translation: 一种氧化环状苯酚硫化物的制造方法，其特征在于，将下述式（1）所示的环状苯酚硫化物氧化为原料，其中，R表示碳原子数1〜6的直链或支链烷基，m表示 4至8的整数，相对于每1重量份环状苯酚硫化物，其量为2重量份以上且小于10重量份的卤代烃类溶剂，以及氧化剂， 得到下述式（2）所示的氧化型环状苯酚硫化物：式中，R表示碳原子数1〜6的直链或支链烷基，m为4〜8的整数，n为1或2。

公开(公告)号：US20120315576A1

公开(公告)日：2012-12-13

申请号：US13581226

申请日：2011-02-21

Applicant: Masateru Yasumura ,  Masami Ito ,  Masaya Tojo ,  Kanae Hiraishi ,  Masaki Okubo ,  Hideyuki Otsuka

Inventor： Masateru Yasumura ,  Masami Ito ,  Masaya Tojo ,  Kanae Hiraishi ,  Masaki Okubo ,  Hideyuki Otsuka

IPC: C07D413/06 ,  C07D277/36 ,  G03G9/16

CPC classification number: G03G9/09758 ,  C09B23/0008 ,  C09B23/0025 ,  C09B23/0091 ,  C09B23/04 ,  G03G9/0806 ,  G03G9/081 ,  G03G9/08711 ,  G03G9/0904 ,  G03G9/0914 ,  G03G9/09775

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 translation: 本发明提供一种电荷控制剂，其含有作为活性物质的一种或两种以上由下式（1）表示的绕丹宁化合物。 其中R1表示氢原子等; R2表示氢原子，可具有取代基的碳原子数1〜8的直链或支链烷基，取代或未取代的杂环基等。 可以相同或不同的R 3〜R 7表示氢原子，可以具有取代基的碳原子数1〜10的直链或支链烷基，碳原子数1〜20的直链或支链烷氧基 其可以具有取代基等，并且可以彼此连接形成环; V，W，X，Y和Z表示碳原子或氮原子，V，W，X，Y和Z中的任一个中的0〜3为不具有R 3〜R 7的取代基的氮原子。