Dental composition

Patent metadata

Field	Value
Publication number	US-2020046612-A1
Application number	US-201816485548-A
Country	US
Kind code	A1
Filing date	Feb 8, 2018
Priority date	Feb 13, 2017
Publication date	Feb 13, 2020
Grant date	—

Abstract

The present invention relates to a dental composition comprising
(i) a polymerizable composition containing a compound having repeating units of the following formula (I):

wherein
R 1 represents a hydrogen atom or a linear C 1-6 alkyl group, or a branched or cyclic C 3-6 alkyl group;
L represents a divalent organic linker group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups;
n is an integer of at least 1; and

(ii) one or more vinyl compounds selected from vinyl ethers, vinyl esters, vinylsiloxanes, (meth) acrylamides and 1-alkenes having from 4 to 20 carbon atoms, said vinyl compounds being copolymerizable with the compound having repeating units of formula (I); and
(iii) a polymerization initiator system.

First claim

1 . A dental composition comprising
(i) a polymerizable composition containing a compound having repeating units of the following formula (I):

wherein
R 1 represents a hydrogen atom or a linear C 1-6 alkyl group, or a branched or cyclic C 3-6 alkyl group;
L represents a divalent organic linker group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups; and
n is an integer of at least 1;

(ii) one or more vinyl compounds selected from vinyl ethers, vinyl esters, vinylsiloxanes, (meth) acrylamides and 1-alkenes having from 4 to 20 carbon atoms, said vinyl compounds being copolymerizable with the compound having repeating units of formula (I); and
(iii) a polymerization initiator system.

2 . The dental composition according to claim 1 , wherein the polymerizable composition containing a compound having repeating units of formula (I) is obtainable by reacting a mixture comprising:
(a) x equivalents of one or more compounds of the following formula (I):

wherein
R 1 is as defined in claim 1 ;

(b) y equivalents of a compound of the following formula (II):
HO-L-OH   (III)

wherein
L is as defined in claim 1 ; and

(c) optionally z equivalents of one or more compounds of the following formula (IV) or (V):
R 2 —COOH   (IV)

R 2 —OH   (V)

wherein
R 2 independently is an organic group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups, and/or one or more polymerizable groups selected from (meth)acryloyl groups, (meth)acrylamido groups, vinyl ether groups, vinyl ester groups, aziridine, epoxide groups and oxetane groups,

wherein 0.05≤x/y≤0.66, and 2y−2x≤z≤1.5(2y−2x), wherein x, y, and z are the molar equivalents of components (a), (b) and (c).

3 . The dental composition according to claim 1 , wherein R 1 is a hydrogen atom.

4 . The dental composition according to claim 1 , wherein L is a divalent hydrocarbyl group.

5 . The dental composition according to claim 1 , wherein L is a divalent organic linker group containing a divalent organopolysiloxane group.

6 . The dental composition according to claim 1 , wherein the organopolysiloxane group contains a polymerizable group selected from vinylether, vinylester, oxetane, and aziridine groups.

7 . The dental composition according to claim 1 , which is adapted to form an interpenetrating network (IPN) by a combination of a free radical polymerization and a cationic polymerization.

8 . The dental composition according to claim 1 , wherein the polymerizable composition (i) has a refractive index of from 1.450 to 1.540.

9 . The dental composition according to claim 1 which is selected from a dental impression material and a dental composite.

10 . A process for the preparation of a polymerizable composition for use in a dental composition, which comprises reacting a mixture comprising:
(a) x equivalents of one or more compounds of the following formula (I):

wherein
R 1 represents a hydrogen atom or a linear C 1-6 alkyl group, or a branched or cyclic C 3-6 alkyl group;

(b) y equivalents of a compound of the following formula (II):
HO-L-OH   (III)

wherein
L represents a divalent organic linker group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups; and

(c) optionally z equivalents of one or more compounds of the following formula (IV) or (V):
R 2 —COOH   (IV)

R 2 —OH   (V)

wherein
R 2 independently is an organic group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups, and/or one or more polymerizable groups selected from (meth)acryloyl groups, (meth)acrylamido groups, vinylether groups, vinylester groups, aziridine, epoxide groups and oxetane groups,

wherein 0.05≤x/y≤0.66, and 2y−2x≤z≤1.5(2y−2x), wherein x, y, and z are the molar equivalents of components (a), (b) and (c).

11 . A polymerizable composition obtained by a process of comprising reacting a mixture comprising:
(a) x equivalents of one or more compounds of the following formula (I):

wherein
R 1 represents a hydrogen atom or a linear C 1-6 alkyl group, or a branched or cyclic C 3-6 alkyl group;

(b) y equivalents of a compound of the following formula (II):
HO-L-OH   (III)

wherein
L represents a divalent organic linker group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups; and

(c) optionally z equivalents of one or more compounds of the following formula (IV) or (V):
R 2 —COOH   (IV)

R 2 —OH   (V)

wherein
R 2 independently is an organic group which may contain one or more monovalent or divalent organopolysiloxane groups and/or one or more monovalent or divalent perfluorohydrocarbyl groups, and/or one or more polymerizable groups selected from (meth)acryloyl groups, (meth)acrylamido groups, vinylether groups, vinylester groups, aziridine, epoxide groups and oxetane groups,

wherein 0.05≤x/y≤0.66, and 2y−2x≤z≤1.5(2y−2x), wherein x, y, and z are the molar equivalents of components (a), (b) and (c).

12 . The polymerizable composition according to claim 11 , which comprises polymerizable macromonomers of one of the following formula (VI):

wherein
m is an integer of from 0 to 20,
o is an integer of from 0 to 20,
p is an integer of from 1 to 40,
R 1 represents a hydrogen atom or a linear C 1-6 , branched C 2-6 or cyclic C 3-6 alkyl group,
R 3 represents a linear C 1-6 , or a branched or cyclic C 3-6 alkyl group,
R 4 represents a vinyl group, a vinylether group, a vinylester group, an aziridine group, an oxetane group or a represents a linear C 1-6 , or a branched or cyclic C 3-6 alkyl group, and
wherein n is an average chain length which is in the range of from 1 to 50.

13 . A method of using a polymerizable macromonomer of the formula (VI)

wherein
m is an integer of from 0 to 20,
o is an integer of from 0 to 20,
p is an integer of from 1 to 40,
R 1 represents a hydrogen atom or a linear C 1-6 , branched C 2-6 or cyclic C 3-6 alkyl group,
R 3 represents a linear C 1-6 , or a branched or cyclic C 3-6 alkyl group,
R 4 represents a vinyl group, a vinylether group, a vinylester group, an aziridine group, an oxetane group or a represents a linear C 1-6 , or a branched or cyclic C 3-6 alkyl group, and
wherein n is an average chain length which is in

Assignees

• Dentsply Detrey Gmbh
• Dentsply Sirona Inc

Inventors

• Klee Joachim
• Wörner Melissa
• Szillat Florian
• Ritter Helmut

Classifications

• A61K6/76

  comprising silicon-containing compounds · CPC title

• A61K6/20 Primary

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title

• A61K6/896 Primary

  Polyorganosilicon compounds · CPC title

• A61K6/79

  Initiators · CPC title

• A61K6/0097

  Human Necessities · mapped topic