公开(公告)号：US11104643B2

公开(公告)日：2021-08-31

申请号：US16930397

申请日：2020-07-16

Applicant: UNITIKA LTD.

Inventor： Yuki Yamada ,  Tatsuya Morikita ,  Takeshi Yoshida ,  Akira Shigeta ,  Yoshiaki Echigo

IPC: C07D207/448

Abstract: An object of the present invention is to provide a bismaleimide (D-BMI) modified product in which an amino group of dimer diamine (DDA) is maleimidized, which has the good heat resistance, and has the sufficiently enhanced processability, and a method for producing the same. There are provided: A bismaleimide (D-BMI) modified product in which an amino group of dimer diamine is maleimidized, the bismaleimide modified product having the following characteristics: 1) An acid value of the D-BMI modified product is 2 mg-KOH/g or less. 2) In 1H-NMR, when quantitative comparison is performed using an integrated value (A) of a peak corresponding to a proton of a methylene group directly bound to a nitrogen atom of a maleimide group and an integrated value (B) of a peak corresponding to a vinyl proton of a maleimide group, A/B is 1.25 or more and 2.00 or less. A method for producing D-BMI, the method including the following steps: 1) A step of preparing a crude D-BMI solution having an acid value of more than 2 mg-KOH/g. 2) A step of lowering an acid value of D-BMI to 2 mg-KOH/g or less by reacting an acid component in the solution with a carbodiimide compound. 3) A step of reacting the solution without a catalyst at 110 to 200° C. in a solvent.

公开(公告)号：US10759753B2

公开(公告)日：2020-09-01

申请号：US16011077

申请日：2018-06-18

Applicant: UNITIKA LTD.

Inventor： Yuki Yamada ,  Tatsuya Morikita ,  Takeshi Yoshida ,  Akira Shigeta ,  Yoshiaki Echigo

IPC: C07D207/448

Abstract: An object of the present invention is to provide a bismaleimide (D-BMI) modified product in which an amino group of dimer diamine (DDA) is maleimidized, which has the good heat resistance, and has the sufficiently enhanced processability, and a method for producing the same. There are provided: A bismaleimide (D-BMI) modified product in which an amino group of dimer diamine is maleimidized, the bismaleimide modified product having the following characteristics: 1) An acid value of the D-BMI modified product is 2 mg-KOH/g or less. 2) In 1H-NMR, when quantitative comparison is performed using an integrated value (A) of a peak corresponding to a proton of a methylene group directly bound to a nitrogen atom of a maleimide group and an integrated value (B) of a peak corresponding to a vinyl proton of a maleimide group, A/B is 1.25 or more and 2.00 or less. A method for producing D-BMI, the method including the following steps: 1) A step of preparing a crude D-BMI solution having an acid value of more than 2 mg-KOH/g. 2) A step of lowering an acid value of D-BMI to 2 mg-KOH/g or less by reacting an acid component in the solution with a carbodiimide compound. 3) A step of reacting the solution without a catalyst at 110 to 200° C. in a solvent.

公开(公告)号：US11958806B2

公开(公告)日：2024-04-16

申请号：US17037164

申请日：2020-09-29

Applicant: UNITIKA LTD.

Inventor： Yuki Yamada ,  Tatsuya Morikita ,  Yosuke Sugimoto ,  Takeshi Yoshida ,  Akira Shigeta ,  Yoshiaki Echigo

IPC: C07D207/448 ,  B01D9/00 ,  B01D11/04 ,  C07C267/00

CPC classification number: C07D207/448 ,  B01D9/005 ,  B01D11/0492 ,  C07C267/00

Abstract: An object is to provide a method for easily producing maleimide (MI) in which trace amounts of residual acid components as impurities in a crude MI are efficiently reduced, that is, the acid value is sufficiently reduced.



A method for producing purified MI, comprising reducing an acid value of crude MI by 50% or more, by adding carbodiimide (CDI) to a solution comprising the crude MI to react an acid component in the crude MI with the CDI.
The method for producing purified MI, comprising adding 0.5% by mass or more and 8% by mass or less of the CDI with respect to a mass of the crude MI for reaction.
The method for producing purified MI, wherein the CDI is N,N′-diisopropyl carbodiimide (DIC).
The method for producing purified MI, comprising removing a urea derivative of the CDI (CDI-U) by-produced when reacting the acid component in the crude MI with the CDI.

公开(公告)号：US20210009516A1

公开(公告)日：2021-01-14

申请号：US17037164

申请日：2020-09-29

Applicant: UNITIKA LTD.

Inventor： Yuki Yamada ,  Tatsuya Morikita ,  Yosuke Sugimoto ,  Takeshi Yoshida ,  Akira Shigeta ,  Yoshiaki Echigo

IPC: C07D207/448 ,  B01D11/04 ,  B01D9/00

Abstract: An object is to provide a method for easily producing maleimide (MI) in which trace amounts of residual acid components as impurities in a crude MI are efficiently reduced, that is, the acid value is sufficiently reduced. A method for producing purified MI, comprising reducing an acid value of crude MI by 50% or more, by adding carbodiimide (CDI) to a solution comprising the crude MI to react an acid component in the crude MI with the CDI. The method for producing purified MI, comprising adding 0.5% by mass or more and 8% by mass or less of the CDI with respect to a mass of the crude MI for reaction. The method for producing purified MI, wherein the CDI is N,N′-diisopropyl carbodiimide (DIC). The method for producing purified MI, comprising removing a urea derivative of the CDI (CDI-U) by-produced when reacting the acid component in the crude MI with the CDI.