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1. 发明申请

US20120253054A1 METHODS FOR PRODUCING OXIDIZED CYCLIC PHENOL SULFIDES 有权
标题翻译：生产氧化环丙醇硫化物的方法
公开(公告)号：US20120253054A1
公开(公告)日：2012-10-04
申请号：US13523420
申请日：2012-06-14
申请人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
发明人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
IPC分类号： C07D341/00
CPC分类号： C07D341/00
摘要： 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.
摘要翻译：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。

2. 发明授权

US07820832B2 Oxidized mixed cyclic phenol sulfides, and charge control agents and toners using the same 有权
标题翻译：氧化混合环状苯酚硫化物，以及使用其的电荷控制剂和调色剂
公开(公告)号：US07820832B2
公开(公告)日：2010-10-26
申请号：US12481112
申请日：2009-06-09
申请人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
发明人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
IPC分类号： C07D339/08
CPC分类号： G03G9/09775 , C07D341/00 , G03G9/08748 , G03G9/08771
摘要： 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.
摘要翻译：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。

3. 发明申请

US20090035678A1 MIXED CYCLIC PHENOL SULFIDES, AND CHARGE CONTROL AGENTS AND TONERS USING THE SAME 有权
标题翻译：混合循环酚醛硫酸盐，以及充电控制剂和使用它的调色剂
公开(公告)号：US20090035678A1
公开(公告)日：2009-02-05
申请号：US12240520
申请日：2008-09-29
申请人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
发明人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
IPC分类号： G03G9/00 , C07D341/00
CPC分类号： G03G9/09733 , C07D341/00 , G03G9/08711 , G03G9/0904 , G03G9/09758 , G03G9/09775
摘要： 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.
摘要翻译：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。

4. 发明授权

US08232429B2 Methods for producing oxidized cyclic phenol sulfides 有权
标题翻译：氧化环状苯酚硫化物的制备方法
公开(公告)号：US08232429B2
公开(公告)日：2012-07-31
申请号：US12503895
申请日：2009-07-16
申请人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
发明人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
IPC分类号： C07C315/00
CPC分类号： C07D341/00
摘要： 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.
摘要翻译：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。

5. 发明申请

US20090275783A1 METHODS FOR PRODUCING OXIDIZED CYCLIC PHENOL SULFIDES 有权
标题翻译：生产氧化环丙醇硫化物的方法
公开(公告)号：US20090275783A1
公开(公告)日：2009-11-05
申请号：US12503895
申请日：2009-07-16
申请人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
发明人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
IPC分类号： C07C319/02
CPC分类号： C07D341/00
摘要： 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.
摘要翻译：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。

6. 发明申请

US20090042120A1 OXIDIZED MIXED CYCLIC PHENOL SULFIDES, AND CHARGE CONTROL AGENTS AND TONERS USING THE SAME 有权
标题翻译：氧化的混合循环硫醇，以及充电控制剂和使用它的调色剂
公开(公告)号：US20090042120A1
公开(公告)日：2009-02-12
申请号：US12249766
申请日：2008-10-10
申请人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
发明人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
IPC分类号： G03G9/00 , C07D341/00 , C09K3/00
CPC分类号： G03G9/09775 , C07D341/00 , G03G9/08748 , G03G9/08771
摘要： 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.
摘要翻译：本发明公开了氧化型环状苯酚硫化物，其中在8中的氧化环状苯酚硫化物和其中m为8以外的整数的氧化型环状苯酚硫化物的混合物，氧化的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。

7. 发明授权

US08624065B2 Methods for producing oxidized cyclic phenol sulfides 有权
标题翻译：氧化环状苯酚硫化物的制备方法
公开(公告)号：US08624065B2
公开(公告)日：2014-01-07
申请号：US13523420
申请日：2012-06-14
申请人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
发明人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
IPC分类号： C07C315/00
CPC分类号： C07D341/00
摘要： 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.
摘要翻译：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。

8. 发明授权

US07709172B2 Oxidized mixed cyclic phenol sulfides, and charge control agents and toners using the same 有权
公开(公告)号：US07709172B2
公开(公告)日：2010-05-04
申请号：US12249766
申请日：2008-10-10
申请人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
发明人： Masateru Yasumura , Masami Ito , Naohiro Tarumoto , Yoshikazu Aoki , Masafumi Umekawa , Masaki Okubo , Hideyuki Otsuka , Jun Watanabe
IPC分类号： G03G9/08
CPC分类号： G03G9/09775 , C07D341/00 , G03G9/08748 , G03G9/08771
摘要： 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.

9. 发明申请

US20090264661A1 METHODS FOR PRODUCING CYCLIC PHENOL SULFIDES 有权
标题翻译：生产循环酚醛硫化物的方法
公开(公告)号：US20090264661A1
公开(公告)日：2009-10-22
申请号：US12439121
申请日：2007-08-29
申请人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
发明人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
IPC分类号： C07D337/16
CPC分类号： C07D341/00
摘要： 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.
摘要翻译：本发明的目的在于提供环状苯酚硫化物的制造方法，提供多种大环化合物的制造方法，其特征在于，在一个步骤中，从一价廉的原料制造环状苯酚硫化物的混合物，循环四聚体的产率降低; 并且容易地从环状苯酚硫化物的混合物中分离和纯化单一组分。本发明公开了一种环状苯酚硫化物的制造方法，其特征在于，在一步反应中，使作为原料的酚化合物与1.7〜2.5摩尔当量的硫和0.25〜0.75摩尔当量的碱金属试剂，每1mol酚化合物，得到m = 4的环状苯酚硫化物和m = 5〜9的至少一种环状苯酚硫化物或混合物中所含的各自分离的环状苯酚硫化物的混合物。

10. 发明授权

US08263786B2 Methods for producing cyclic phenol sulfides 有权
标题翻译：环状苯酚硫化物的制备方法
公开(公告)号：US08263786B2
公开(公告)日：2012-09-11
申请号：US12439121
申请日：2007-08-29
申请人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
发明人： Masateru Yasumura , Yoshikazu Aoki , Masami Ito , Masafumi Umekawa , Naohiro Tarumoto
IPC分类号： C07D341/00
CPC分类号： C07D341/00
摘要： 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.
摘要翻译：本发明的目的在于提供环状苯酚硫化物的制造方法，提供多种大环化合物的制造方法，其特征在于，在一个步骤中，从一价廉的原料制造环状苯酚硫化物的混合物，循环四聚体的产率降低; 并且容易地从环状苯酚硫化物的混合物中分离和纯化单一组分。本发明公开了一种环状苯酚硫化物的制造方法，其特征在于，在一步反应中，使作为原料的酚化合物与1.7〜2.5摩尔当量的硫和0.25〜0.75摩尔当量的碱金属试剂，每1mol酚化合物，得到m = 4的环状苯酚硫化物和m = 5〜9的至少一种环状苯酚硫化物或混合物中所含的各自分离的环状苯酚硫化物的混合物。

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