Dental adhesive

Patent metadata

Field	Value
Publication number	US-2018214351-A1
Application number	US-201615747803-A
Country	US
Kind code	A1
Filing date	Jul 27, 2016
Priority date	Jul 27, 2015
Publication date	Aug 2, 2018
Grant date	—

Abstract

The present invention relates to an aqueous dental composition having a pH of at most 7. Furthermore, the present invention relates to the use of a specific composition for the preparation of an aqueous dental composition.

First claim

1 . An aqueous dental composition having a pH of at most 7, comprising:
(a) 1 to 70 percent by weight based on the total weight of the composition of a polymerizable compound of the following formula (I):
A-L-B  (I)

wherein
A is a group of the following formula (II)

X 1 is CO, CS, CH 2 , or a group [X′Z] k , wherein X′ is an oxygen atom, a sulfur atom or NH, Z is a straight chain or branched C 1-4 alkylene group, and k is an integer of from 1 to 10;
R 1 is a hydrogen atom,
—COOM,
a straight chain or branched C 1-16 alkyl group which may be substituted by a C 3-6 cycloalkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
a C 3-6 cycloalkyl group which may be substituted by a C 1-16 alkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
a C 6-14 aryl or C 3-14 heteroaryl group which may be substituted by —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,

R 2 is a hydrogen atom,
—COOM
a straight chain or branched C 1-16 alkyl group which may be substituted by a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 and —SO 3 M,
a C 3-6 cycloalkyl group which may be substituted by a C 1-16 alkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, or
a C 6-14 aryl or C 3-14 heteroaryl group which may be substituted by —COOM, —PO 3 M, —O—PO 3 M 2 and —SO 3 M,

L is a divalent C 2-12 alkenylene linker group, which may contain 1 to 3 carbonyl groups or heteroatoms selected from oxygen, nitrogen and sulfur, and which may be substituted by a hydroxyl group, a C 6-14 aryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, wherein M is a hydrogen atom or a metal atom;
B is selected from
(i) a group according to the definition of A,
(ii) a group of the following formula (III)

X 2 independently has the same meaning as defined for X′ in formula (II),
R 1′ and R 2′ are independent from each other and independently have the same meaning as defined for R 1 and R 2 in formula (II),
R is a hydrogen atom,
 a straight chain or branched C 1-16 alkyl group which may be substituted by a C 3-6 cycloalkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
 a C 3-6 cycloalkyl group which may be substituted by a C 1-16 alkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
 a C 6-14 aryl or C 3-14 heteroaryl group which may be substituted by —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,

(iii) a group of the following formula (IV)

wherein
X 3 is CO, —CH 2 CO—, CS, or —CH 2 CS—,
R 1′ and R 2″ which are independent from each other and independently have the same meaning as defined for R 1 and R 2 in formula (II), or

(iv) a group [Z′X″] m E, wherein
Z′ is a straight chain or branched C 1-4 alkylene group,
X″ is an oxygen atom, a sulfur atom or NH,
E is a hydrogen atom,
 PO 3 M 2 ,
 a straight chain or branched C 1-16 alkyl group which may be substituted by a C 3-6 cycloalkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
 a C 3-6 cycloalkyl group which may be substituted by a C 1-16 alkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
 a C 6-14 aryl or C 3-14 heteroaryl group which may be substituted by —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, and
m is an integer of from 1 to 10; and

wherein M of any one R 1 , R 2 , L, R and E, which M are independent from each other, each represent a hydrogen atom or a metal atom;

(b) 2 to 20 percent by weight based on the total weight of the composition of a polymerizable compound of the following formula (V):
A′-L′-A′   (V)

wherein the
A′ which are independent from each other, each represent a group of the following formula (VI)

wherein
X 2 * independently has the same meaning as defined for X 1 in formula (II),
R 1 * and R 2 * are independent from each other and independently have the same meaning as defined for R 1 and R 2 in formula (II),
R* is a hydrogen atom,
a straight chain or branched C 1-16 alkyl group which may be substituted by a C 3-6 cycloalkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
a C 3-6 cycloalkyl group which may be substituted by a C 1-16 alkyl group, a C 6-14 aryl or C 3-14 heteroaryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,
a C 6-14 aryl or C 3-14 heteroaryl group which may be substituted by —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M,

L′ is a divalent C 2-12 alkylene linker group, which may contain 1 to 3 carbonyl groups or heteroatoms selected from oxygen, nitrogen and sulfur, and which may be substituted by a hydroxyl group, a C 6-14 aryl group, —COOM, —PO 3 M, —O—PO 3 M 2 or —SO 3 M, wherein M is a hydrogen atom or a metal atom;
wherein M of any one R 1′ , R 2 *, L′ and R*, which M are independent from each other, each represent a hydrogen atom or a metal atom;

(c) 1 to 20 percent by weight based on the total weight of the composition of one or more polymerizable monomers having one or more acidic groups;
(d) 0.001 to 5 percent by weight based on the total weight of the composition of an initiator system;
(e) 0.001 to 1 percent by weight based on the total weight of the composition of a stabilizer; and
(f) 25 to 50 percent by weight based on the total weight of the composition of a solvent mixture comprising water and an organic solvent.

2 . The aqueous dental composition according to claim 1 , wherein B is a group according to the definition of A.

3 . The aqueous dental composition according to claim 1 or 2 , wherein X 1 in formula (II) is CO.

4 . The aqueous dental composition according to any one of the preceding claims, wherein X 2 in formula (VI) is CO.

5 . The aqueous dental composition according to any one of the preceding claims wherein L is —CH 2 CH═CHCH 2 —.

6 . The aqueous dental composition according to any one of the preceding claims, comprising a polymerizable phosphoric acid ester as a polymerizable monomer having one or more acidic groups.

7 . The aqueous dental composition according to any one of the preceding claims, which further comprises a polymerizable monomer having at least three polymerizable double bonds.

8 . The aqueous dental composition according to any one of the preceding claims, wherein the stabilizer is a compound of the following formula (VII) and/or (VIII):

wherein
the R 3 , which may be the same or different, independently represent a branched C 3-8 alkyl or alkenyl group or a C 3-8 cycloalkyl or cycloalkenyl group,
R 4 represents

Assignees

• Dentsply Detrey Gmbh
• Dentsply Sirona Inc

Inventors

• Fik Christoph P
• Pohle Sven
• Liu Huaibing
• Klee Joachim

Classifications

• A61K6/77

  Glass · CPC title

• A61K6/71

  Fillers · CPC title

• A61K6/818

  comprising zirconium oxide · CPC title

• A61K6/813

  comprising iron oxide · CPC title

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title