Hydrolysis stable self-etching, self-priming adhesive
OwnerJoachim Klee, Uwe Walz +1inventors
InventorsJoachim Klee, Uwe Walz, Uwe Lehman
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Abstract
An aqueous one-pack self-etching and self-priming dental adhesive composition having a pH of at most 2, which comprises: (i) a polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety, and (ii) a curing system.
Claims25
An aqueous one-pack self-etching and self-priming dental adhesive composition having a pH of at most 2, which comprises:
- (i) a polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety, and (ii) a curing system.
The composition of any of the preceding claims, which comprises an organic or inorganic acid.
The composition of any of the preceding claims, which contains beside water an organic water-soluble solvent, preferably selected from alcohols and ketones.
The composition of any of the preceding claims, wherein the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety (i) is hydrolysis-stable according to the following test:
- 1.5 mmol of the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer (i), and in case the monomer does not contain an acidic moiety 1 equivalent of ethanesulfonic acid per alkylacrylamide or acrylamide group, are solved in 5 g of a solvent mixture consisting of 50 wt.-% ethanol and 50 wt.-% water to obtain a mixture which is stored in a closed vial in an oven at 50.degree. C.;
- and after 2 weeks of such a storage the hydrolysis of the tested monomer is less than 50% according to a HPLC-analysis of the absolute amount of the alkylacrylic or acrylic acid formed by hydrolysis of the tested monomer.
The composition of any of the preceding claims, wherein the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer containing at least an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety (iii) is hydrolysis-stable according to the following test:
- 1.5 mmol of the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer containing at least an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety (iii) are solved in 5 g of a solvent mixture consisting of 50 wt.-% ethanol and 50 wt.-% water to obtain a mixture which is stored in a closed vial in an oven at 50.degree. C.;
- and after 2 weeks of such a storage the hydrolysis of the tested polymerizable N-substituted alkylacrylic or acrylic acid amide monomer is less than 50% according to a HPLC-analysis of the absolute amount of the alkylacrylic or acrylic acid formed by hydrolysis of the tested polymerizable N-substituted alkylacrylic or acrylic acid amide monomer.
The composition of any of the preceding claims, wherein the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety or the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer containing at least an inorganic acidic moiety contains at least two polymerizable groups.
The composition of any of the preceding claims, which further contains a nanofiller.
The composition of any of the preceding claims wherein the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety is selected from the group consisting of compounds represented by the following formulas:
- wherein R.sub.1, R.sub.1″ and R.sub.3 independently are hydrogen or a substituted or unsubstituted C.sub.1 to C.sub.18 alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C.sub.5 to C.sub.18 aryl or heteroaryl group, a substituted or unsubstituted C.sub.5 to C.sub.18 alkylaryl or alkylheteroaryl group, a substituted or unsubstituted C.sub.7 to C.sub.30 aralkyl group, provided that in case one of R.sub.1 and R.sub.1″ is hydrogen in formula (F1) the other is not hydrogen;
- R.sub.2 is a difunctional substituted or unsubstituted C.sub.1 to C.sub.18 alkylene, difunctional substituted or unsubstituted cycloalkylene, a difunctional substituted or unsubstituted C.sub.5 to C.sub.18 aryl or heteroaryl group, a difunctional substituted or unsubstituted C.sub.5 to C.sub.18 alkylaryl or alkylheteroaryl group, a difunctional substituted or unsubstituted C.sub.7 to C.sub.30 aralkyl group, R.sub.4 is a mono- or polyfunctional substituted or unsubstituted C.sub.1 to C.sub.18 carbon chain group, a mono- or polyfunctional substituted or unsubstituted cycloalkyl group, a mono- or polyfunctional substituted or unsubstituted C.sub.5 to C.sub.18 aryl or heteroaryl group, a mono- or polyfunctional substituted or unsubstituted C.sub.5 to C.sub.18 alkylaryl or alkylheteroaryl group, a mono- or polyfunctional substituted or unsubstituted C.sub.7 to C.sub.30 aralkyl group, and n is an integer, preferably from 1 to 10, more preferably from 3 to 4.
The composition according to one of the preceding claims, characterized in that the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety is selected from the group consisting of compounds represented by the following formulas:
- wherein n is an integer of from 2 to 6;
- x, y, and z independently is an integer of from 1 to 10;
- and Z is H or a substituted or unsubstituted C.sub.1 to C.sub.18 alkyl group.
The composition according to one of the preceding claims, characterized in that the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety is selected from (meth)acrylamide monomers, preferably from the type of secondary amides.
The composition according to one of the preceding claims, characterized in that the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer containing at least an inorganic acidic moiety is selected from the group consisting of compounds represented by the following formulas:
- wherein R.sub.1′ and R.sub.2′ represent independently from each other a hydrogen atom or a substituted or unsubstituted C.sub.1 to C.sub.18 alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C.sub.5 to C.sub.18 aryl or heteroaryl group, a substituted or unsubstituted C.sub.5 to C.sub.18 alkylaryl or alkylheteroaryl group, a substituted or unsubstituted C.sub.7 to C.sub.30 aralkyl group, R.sub.3′ and R.sub.4′ represent independently from each other a difunctional substituted or unsubstituted C.sub.1 to C.sub.18 carbon chain group, a difunctional substituted or unsubstituted cycloalkylene, a difunctional substituted or unsubstituted C.sub.5 to C.sub.18 aryl or heteroaryl group, a difunctional substituted or unsubstituted C.sub.5 to C.sub.18 alkylaryl or alkylheteroaryl group, a difunctional substituted or unsubstituted C.sub.7 to C.sub.30 aralkyl group, R.sub.5′ represents H or a substituted or unsubstituted C.sub.1 to C.sub.18 alkyl group n is an integer, preferably from 1 to 18 or 1 to 4 and m is an integer, preferably from 1 to 3.
The composition according to one of the preceding claims, characterized in that the polymerizable N-substituted alkylacrylic or acrylic acid amide monomer containing at least an inorganic acidic moiety is selected from (meth)acrylamide monomers, preferably from the type of secondary amides, more preferably from acrylamide monomers from the type of secondary amides.
The composition according to one of the preceding claims, characterized in that the curing system comprises a polymerization initiator, an inhibitor or stabilizer, preferably the curing system is a light-curing system.
A method for the preparation of an aqueous one-pack self-etching and self-priming dental adhesive composition according to any one of the preceding claims, characterized by mixing (A) a polymerizable N-substituted alkylacrylic or acrylic acid amide monomer which optionally contains an inorganic acidic moiety selected from a phosphonic acid moiety or a sulfonic acid moiety, (B) a curing system, and (C) a water containing solvent.
Dependencies are inferred from the claim text.