Compound and synthesis method therefor

Patent metadata

Field	Value
Publication number	US-10835895-B2
Application number	US-201716090405-A
Country	US
Kind code	B2
Filing date	Mar 30, 2017
Priority date	Apr 1, 2016
Publication date	Nov 17, 2020
Grant date	Nov 17, 2020

Abstract

An acetylacetone derivative is useful for capturing a metal element by complexation. A convenient and very versatile synthesis method can be used to synthesize the derivative. The derivative can have the following formula:

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein
M is a hydrogen ion, or a monovalent or higher valent metal ion which may have a ligand;
R 1 and R 2 are, each independently, a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, aryl group, or heterocyclic group, and these groups may include a polymerizable group,
at least one of R 1 and R 2 is a trifluoromethyl group;
R 3 and R 4 are, each independently, a hydrogen atom, a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group, and these groups include a polymerizable group;
R 5 is a alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylamino group, or arylamino group, and these groups include a polymerizable group and may also include a substituent; and
p is 1 or 0, with a proviso that when p=0, R 5 is not an alkoxy group having 4 or less carbon atoms.

2. The compound according to claim 1 , wherein both of R 1 and R 2 are a trifluoromethyl group.

3. The compound according to claim 1 , wherein a divalent residue represented by formula (2) is included in the inside of a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylamino group, arylamino group, alkylthio group, or arylthio group defined as R 5 :
—{O(CH 2 )k}m-  (2)

wherein k is 2 or 3; and m is an integer of 1 to 20.

4. The compound according to claim 1 , wherein M is a lithium ion.

5. The compound according to claim 1 , wherein the compound represented by formula (1) has pKa of 3 to 6.

6. The compound according to claim 1 , wherein the compound represented by formula (1) expresses liquid crystallinity.

7. A composition comprising the compound according to claim 1 , wherein M is a monovalent or higher valent metal ion which may have a ligand.

8. The composition according to claim 7 , wherein the composition has a cumulative structure by self-organization.

9. A composition comprising the compound according to claim 1 , and a compound represented by formula (3):

wherein
R 6 , R 7 , and R 8 are, each independently, a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group, which may include a polymerizable group;
any two of R 6 , R 7 , and R 8 may form a 5 to 7-membered ring containing a phosphorus atom to which the two are bonded together; or
said compound may form a dimer through any one of R 6 , R 7 , and R 8 ; and
each of R 6 to R 8 does not include a polymerizable group, or at least one of R 6 to R 8 includes a polymerizable group.

10. The composition according to claim 9 , wherein at least one of the compound represented by formula (1) and the compound represented by formula (3) includes the polymerizable group, and a polymer including a repeating unit derived from the compound including the polymerizable group is included in the composition.

11. The composition according to claim 9 , wherein in formula (1), M is a monovalent or higher valent metal ion which may have a ligand.

12. The composition according to claim 9 , wherein the composition has a cumulative structure by self-organization.

13. A process for preparing a polymer composition, comprising: polymerizing a composition according to claim 9 comprising a compound represented by formula (1) wherein M is a monovalent or higher valent metal ion which may have a ligand, and a compound represented by formula (3), in which at least one of both compounds has a polymerizable group; eluting a metal salt thereof; and substituting M with a hydrogen atom.

14. A process for preparing a polymer composition, comprising: polymerizing a composition comprising a compound represented by formula (1) according to claim 1 wherein M is a monovalent or higher valent metal ion which may have a ligand; and at least one of R 1 to R 5 includes a polymerizable group; eluting a metal salt thereof; and substituting M with a hydrogen atom.

15. A process for preparing a compound represented by formula (1) according to claim 1 , comprising reacting a compound represented by following formula (4) and a compound represented by following formula (5):

wherein R 9 and R 10 are a substituted or unsubstituted alkyl group, aryl group, heterocyclic group, alkenyl group or alkynyl group, which may include a polymerizable group, and at least one of R 9 and R 10 is a trifluoromethyl group;

wherein R is a halogen element; R 12 and R 13 are a hydrogen atom, a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group; R 14 is a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylamino group, or arylamino group; groups defined as R 12 to R 14 may include a polymerizable group; and p is 0 or 1, with a proviso that when p=0, R 14 is not an alkoxy group having 4 or less carbon atoms.

16. The process according to claim 15 , wherein the compound represented by formula (4) and the compound represented by formula (5) are reacted in the coexistence of an iodine salt of an organic compound.

Assignees

• Univ Tokyo

Inventors

• Kato Takashi
• Kawata Ken

Classifications

• C07C269/02

  from isocyanates with formation of carbamate groups · CPC title

• C08F236/045

  conjugated hydrocarbons other than butadiene or isoprene · CPC title

• C07C49/825

  all hydroxy groups bound to the ring · CPC title

• C07F9/5329

  Polyphosphine oxides or thioxides · CPC title

• C07F9/5325

  Aromatic phosphine oxides or thioxides (P-C aromatic linkage) · CPC title