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US 11,141,357 B2Granted
Dental adhesive
AssigneeDENTSPLY SIRONA Inc.
InventorsChristoph P. Fik, Sven Pohle, Huaibing Liu, Joachim Klee
Life of this patent
Estimating the term…
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.
Claims13
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)
- X1 is CO, CS, CH2, or a group [X′Z]k, wherein X′ is an oxygen atom, a sulfur atom or NH, Z is a straight chain or branched C1-4 alkylene group, and k is an integer of from 1 to 10;
- R1 is a hydrogen atom,
- —COOM,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M,
- R2 is a hydrogen atom,
- —COOM
- a straight chain or branched C1-16 alkyl group which may be substituted by a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 and —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M, or
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 and —SO3M,
- L is a divalent C2-12 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 C6-14 aryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M, 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)
- X2 independently has the same meaning as defined for
- X1 in formula (II),
- R1′ and R2′ are independent from each other and independently have the same meaning as defined for R1 and R2 in formula (II),
- R is a hydrogen atom,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M,
- (iii) a group of the following formula (IV)
- wherein
- X3 is CO, —CH2CO—, CS, or —CH2CS—,
- R1″ and R2″ which are independent from each other and independently have the same meaning as defined for R1 and R2 in formula (II), or
- (iv) a group [Z′X″]mE, wherein
- Z′ is a straight chain or branched C1-4 alkylene group,
- X″ is an oxygen atom, a sulfur atom or NH,
- E is a hydrogen atom,
- PO3M2,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M, and
- m is an integer of from 1 to 10;
- and
- wherein M of any one R1, R2, 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
- X2* independently has the same meaning as defined for X1 in formula (II),
- R1* and R2* are independent from each other and independently have the same meaning as defined for R1 and R2 in formula (II),
- R* is a hydrogen atom,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M,
- L′ is a divalent C2-12 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 C6-14 aryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M, wherein M is a hydrogen atom or a metal atom;
- wherein M of any one R1*, R2*, 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.
57 more elements
A method of using a composition for the preparation of an aqueous dental composition having a pH of at most 7;
- said method comprising the step of mixing the composition 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)
- X1 is CO, CS, CH2, or a group [X′Z]k, wherein X′ is an oxygen atom, a sulfur atom or NH, Z is a straight chain or branched C1-4 alkylene group, and k is an integer of from 1 to 10;
- R1 is a hydrogen atom,
- —COOM,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M,
- R2 is a hydrogen atom,
- —COOM
- a straight chain or branched C1-16 alkyl group which may be substituted by a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 and —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M, or
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 and —SO3M,
- L is a divalent C2-12 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 C6-14 aryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M, 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)
- X2 independently has the same meaning as defined for
- X1 in formula (II),
- R1′ and R2′ are independent from each other and independently have the same meaning as defined for R1 and R2 in formula (II),
- R is a hydrogen atom,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M,
- (iii) a group of the following formula (IV)
- wherein
- X3 is CO, —CH2CO—, CS, or —CH2CS—,
- R1″ and R2″ which are independent from each other and independently have the same meaning as defined for R1 and R2 in formula (II), or
- (iv) a group [Z′X″ ]mE,
- wherein
- Z′ is a straight chain or branched C1-4 alkylene group,
- X″ is an oxygen atom, a sulfur atom or NH,
- E is a hydrogen atom,
- PO3M2,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M, and
- m is an integer of from 1 to 10;
- and
- wherein M of any one R1, R2, 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
- X2* independently has the same meaning as defined for X1 in formula (II),
- R1* and R2* are independent from each other and independently have the same meaning as defined for R1 and R2 in formula (II),
- R* is a hydrogen atom,
- a straight chain or branched C1-16 alkyl group which may be substituted by a C3-6 cycloalkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C3-6 cycloalkyl group which may be substituted by a C1-16 alkyl group, a C6-14 aryl or C3-14 heteroaryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M,
- a C6-14 aryl or C3-14 heteroaryl group which may be substituted by —COOM, —PO3M, —O—PO3M2 or —SO3M,
- L′ is a divalent C2-12 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 C6-14 aryl group, —COOM, —PO3M, —O—PO3M2 or —SO3M, wherein M is a hydrogen atom or a metal atom;
- wherein M of any one R1*, R2*, L′ and R*, which M are independent from each other, each represent a hydrogen atom or a metal atom;
- and
- (c) 0.001 to 1 percent by weight based on the total weight of the composition of a stabilizer;
- to form the aqueous dental composition having a pH of at most 7;
- wherein the aqueous dental composition has storage stability for 30 days at 50° C.
57 more elements
Dependencies are inferred from the claim text.