Polymerizable polyacidic polymer

Patent metadata

Field	Value
Publication number	US-10899861-B2
Application number	US-201615754303-A
Country	US
Kind code	B2
Filing date	Sep 9, 2016
Priority date	Sep 9, 2015
Publication date	Jan 26, 2021
Grant date	Jan 26, 2021

Abstract

The present invention relates to a polymerizable polyacidic polymer and to a process for preparing the polymerizable polyacidic polymer. Furthermore, the present invention relates to an aqueous dental composition comprising the polymerizable polyacidic polymer, to a use of the polymerizable polyacidic polymer for the preparation of a dental composition and to an acrylic acid derivative copolymer.

First claim

The invention claimed is:

1. A polymerizable polyacidic polymer having repeating units of the following formula (I):

wherein R 1 represents a group of the following formula (II):

wherein
Ar is an aromatic group which may be further substituted,
R 2 and R 3 ,
which may be the same or different, independently represent a hydrogen atom, or a C 1-6 alkyl group which may be substituted with a carboxylic acid group;

R which may be the same or different when more than one R is present, represents a hydrogen atom, a carboxylic acid group, a COOR a group, a CONHR b group, or a CONR c 2 group, wherein R a , R b , and R c represent a C 1-6 alkyl group;
R 8 represents a halogen atom or a group selected from —OH, —OR d , —NR e H, —NR e R f , —SH, and —SR g , wherein R d , R e , R f , and R g , represent a C 1-6 alkyl group;
o is an integer of 1 or 2;
n is an integer of 1 to 4;
provided that when o is 2, the R 8 cannot be both OH.

2. The polymerizable polyacidic polymer according to claim 1 , wherein R 1 represents a group of the following formula (II′):

wherein R 2 , R 3 and n are as defined in claim 1 .

3. The polymerizable polyacidic polymer according to claim 1 , which further comprises acidic repeating units of the following formula (III):

wherein
R 4 represents a hydrogen atom, or a C 1-6 alkyl group which may be substituted with a carboxylic acid group.

4. The polymerizable polyacidic polymer according to claim 3 , wherein a molar ratio of repeating units of formula (III) and repeating units of formula (I) ([formula (III)]/[formula (I)]) is in a range of 1000:1 to 1:1.

5. The polymerizable polyacidic polymer according to claim 1 , which has a molecular weight M w in a range of 10,000 to 250,000.

6. The polymerizable polyacidic polymer according to claim 1 , wherein R 1 is a group of the following formula (II″ a ) or (II″ b ):

7. A process for preparing a polymerizable polyacidic polymer having repeating units of the following formula (I):

wherein R 1 represents a group of the following formula (II):

wherein
n is an integer of 1 to 4, wherein the process comprises reacting a polyacidic polymer having repeating units of formula (IV):

wherein R 5 represents a group of formula (V):

wherein
Ar is an aromatic group which may be further substituted;
R 8 represents a halogen atom or a group selected from OH, —OR d , —NR e H, —NR e R f , —SH, and —SR g , wherein R d , R e , R f , and R g , represent a C 1-6 alkyl group; and
o is an integer of 1 or 2, provided that when o is 2, the R 8 cannot be both OH, with a compound of the following formula (VI)

wherein X is a leaving group
R 2 and R 3 ,
which may be the same or different, independently represent a hydrogen atom, or a C 1-6 alkyl group which may be substituted with a carboxylic acid group; and

R which may be the same or different when more than one R is present, represents a hydrogen atom, a carboxylic acid group, a COOR a group, a CONHR b group, or a CONR c 2 group, wherein R a , R b , and R c represent a C 1-6 alkyl group.

8. The process according to claim 7 , wherein
(a) X is a hydroxyl group, and/or
(b) the reaction is carried out in the presence of an organic acid.

9. An aqueous dental composition comprising a polymerizable polyacidic polymer, wherein the polymerizable polyacidic polymer has repeating units of the following formula (I):

wherein R 1 represents a group of the following formula (II):

wherein
Ar is an aromatic group which may be further substituted,
R 2 and R 3 ,
which may be the same or different, independently represent a hydrogen atom, or a C 1-6 alkyl group which may be substituted with a carboxylic acid group;

R which may be the same or different when more than one R is present, represents a hydrogen atom, a carboxylic acid group, a COOR a group, a CONHR b group, or a CONR c 2 group, wherein R a , R b , and R c represent a C 1-6 alkyl group;
R 8 represents a halogen atom or a group selected from —OH, —OR d , —NR e R f , —SH, and —SR g , wherein R d , R e , R f and R g , represent a C 1-6 alkyl group;
o is an integer of 1 or 2;
n is an integer of 1 to 4;
provided that when o is 2, the R 8 cannot be both OH.

10. The aqueous dental composition according to claim 9 , which further comprises a particulate glass filler.

11. The aqueous dental composition according to claim 9 , comprising a polymerizable monomer, a polymerisation initiator and optionally a stabilizer.

Assignees

• Dentsply Sirona Inc

Inventors

• Klee Joachim
• Renn Caroline
• Szillat Florian
• Elsner Oliver
• Scheufler Christian
• Lampe Ulrich
• Ritter Helmut

Classifications

• C08F220/56 Primary

  Acrylamide; Methacrylamide · CPC title

• C07C233/20 Primary

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08F8/30

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C08F2800/20

  as weight or mass percentages · CPC title