Dental adhesive

Patent metadata

Field	Value
Publication number	US-11141357-B2
Application number	US-202016882997-A
Country	US
Kind code	B2
Filing date	May 26, 2020
Priority date	Jul 27, 2015
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

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

The invention claimed is:

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 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,

(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;
wherein the aqueous dental composition has storage stability for 30 days at 50° C.

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 claim 1 , wherein X 2 in formula (VI) is CO.

5. The aqueous dental composition according to claim 1 , wherein L is —CH 2 CH═CHCH 2 —.

6. The aqueous dental composition according to claim 1 , comprising a polymerizable phosphoric acid ester as a polymerizable monomer having one or more acidic groups.

7. The aqueous dental composition according to claim 1 , which further comprises a polymerizable monomer having at least three polymerizable double bonds.

8. The aqueous dental composition according to claim 1 , 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,

Assignees

• Fik Christoph P
• Pohle Sven
• Liu Huaibing
• Klee Joachim
• Dentsply Sirona Inc

Inventors

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

Classifications

• C08F220/54

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• A61K6/813

  comprising iron oxide · CPC title

• C07D295/185 Primary

  from aliphatic carboxylic acids · CPC title

• C08L33/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• A61K6/77

  Glass · CPC title