IP Library Granted Patent US 8,148,571
Granted Patent B2
US 8,148,571 · App. 12/443,620 · Granted Apr 3, 2012

Compound, composition comprising the same, and process for production of polymerizable amide

Assignee: Kuraray Medical Inc.
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Quick Facts
Patent No.
US 8,148,571
App. No.
12/443,620
Granted
Apr 3, 2012
Kind
B2
Abstract

A novel compound (I) represented by the following formula (1) is provided which is suitable for a dental composition and has a polymerizable group, a carboxyl group and a phosphoric acid group. A method for producing a polymerizable amide is provided, which method can make a condensation reaction of a carboxylic acid with an amine to proceed easily and is excellent in safety: wherein R 1 , R 2 and R 3 each independently are a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; (A) and (B) are each any constituent unit; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R 4 is an organic group having 1 to 40 carbon atoms which may have a substituent; R 5 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a metal atom.

Claims (98)

1. A compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms;

A is —CONH— or —COO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom.

2. The compound (I) of claim 1 , wherein R 1 and R 2 are each a hydrogen atom and R 3 is a hydrogen atom or a methyl group.

3. The compound (I) of claim 1 , wherein A is —CONH—.

4. The compound (I) of claim 1 , wherein B is —CONH—.

5. The compound (I) of claim 1 , wherein R 5 is one selected from the group consisting of —CH 2 -Ph-, —CH(CH 3 )— and —CH 2 —.

6. A composition comprising a compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms;

A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH 2 O—, —CH 2S—, —C 6 H 4 O—, —C 6 H 4 CONH—, —C 6 H 4 NHCO—, —C 6 H 4 COO—, —C 6 H 4 OCO— and —CONHCO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom,

and a polymerizable monomer (II) which is other than the compound (I) and which can be copolymerized with the compound (I).

7. A composition comprising compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms;

A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH 2 O—, —CH 2 S—, —C 6 H 4 O—, —C 6 H 4 CONH—, —C 6 H 4 NHCO—, —C 6 H 4 COO—, —C 6 H 4 OCO— and —CONHCO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom,

said composition further comprising at least one of the following:

a polymerization initiator (III),

a polymerization accelerator (IV),

and a filler (V).

8. The composition of claim 6 , wherein the polymerizable monomer (II) is a (meth)acrylate compound.

9. The composition of claim 7 , which comprises said polymerization initiator (III).

10. The composition of claim 7 , which comprises said polymerization accelerator (IV).

11. The composition of claim 7 , which comprises said filler (V).

12. The composition of claim 7 , which comprises said solvent (VI).

13. The composition of claim 12 , wherein the solvent (VI) comprises water (VII).

14. A primer comprising the composition of claim 6 , a compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms;

A is one selected from the group consisting of —CONH—, —COO—,—OCO—, —O—, —S—, —CH 2 O—, —CH 2 S—, —C 6 H 4 O—, —C 6 H 4 CONH—, 13 C 6 H 4 NHCO—, —C 6 H 4 COO—, —C 6 H 4 OCO— and —CONHCO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom.

15. A bonding material comprising the composition of claim 6 , a compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms:

A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH 2 O—, —CH 2 S—, —C 6 H 4 O—, —C 6 H 4 CONH—, —C 6 H 4 NHCO—, —C 6 COO—, —C 6 H 4 OCO— and —CONHCO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom.

16. A cement comprising the composition of claim 6 , a compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms;

A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH 2 O—, —CH 2 S—, —C 6 H 4 O—, —C 6 H 4 CONH—, —C 6 H 4 NHCO—, —C 6 H 4 COO—, —C 6 H 4 OCO— and —CONHCO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom.

17. A composite resin comprising the composition of claim 6 , a compound (I) represented by formula (1):

wherein

R 1 , R 2 and R 3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms;

A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH 2 O—, —CH 2 S—, —C 6 H 4 O—, C 6 H 4 CONH—, —C 6 H 4 NHCO—, —C 6 H 4 COO—, —C 6 H 4 OCO— and —CONHCO—;

B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—;

m is an integer of from 1 to 3;

n is an integer of from 1 to 3;

R 4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms;

R 5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms;

R 6 and R 7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom.

18. A method for producing the compound (I) of claim 4 , comprising reacting a carboxylic acid represented by formula (2) by condensation reaction with an amine represented by formula (3):

wherein R 1 , R 2 , R 3 , R 4 , (A), m and n are the same as those of the formula (1),

wherein R 5 , R 6 and R 7 are the same as those of the formula (1).

19. The method for producing the compound (I) of claim 18 , wherein the carboxylic acid contains a (meth)acryl group.

20. The method for producing the compound (I) of claim 18 , wherein a condensing agent present during said reacting is a triazine compound.

21. A method for producing the compound (I) of claim 4 , comprising reacting an acid halide represented by formula (4) with an amine represented by formula (3):

wherein R 1 , R 2 , R 3 , R 4 , (A), m and n are the same as those of the formula (1), and X is a halogen atom,

wherein R 5 , R 6 and R 7 are the same as those of the formula (1).

22. The method for producing the compound (I) of claim 21 , wherein the acid halide contains a (meth)acryl group.

23. The method for producing the compound (I) claim 18 , wherein the amine is a phosphate of an amino acid.

24. The method for producing the compound (I) of claim 23 , wherein the amine is one selected from the group consisting of phosphoserine, phosphothreonine and phosphotyrosine.

25. The method for producing the compound (I) claim 21 , wherein the amine is a phosphate of an amino acid.

26. The compound (I) of claim 1 , wherein A is —COO—.

Assignments (2)
CHANGE OF NAME Recorded Aug 20, 2012
From: KURARAY MEDICAL INC.
To: KURARAY NORITAKE DENTAL INC.
Reel/Frame 028813/0704 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2009
From: SEKIGUCHI, TAKAHIRO; HINAMOTO, AI
To: KURARAY MEDICAL INC.
Reel/Frame 022495/0304 →
Priority Claims (2)
JP 2006-266500 · Sep 29, 2006 · national
JP 2006-266501 · Sep 29, 2006 · national
Continuity (1)
Related Publication 20100076157A1 · Mar 25, 2010