Filler containing composition and process for production and use thereof
View Patent ↗The invention relates to a composition comprising an ethylenically unsaturated acidic compound, water, a functionalized silane, an initiator, optionally comprising a sensitising agent, a non-surface treated filler, optionally a solvent, optionally an ethylenically unsaturated compound, optionally additives selected from the group consisting of stabilizer(s), photobleachable colorant(s), fluoride release agent(s), pigments. The invention also relates to a process of producing such a composition by in-situ silanization of the non-surface treated filler.
1. A method for producing a dental composition comprising the steps of
(i) providing the following components:
(a) about 3 to about 80 parts by weight of an ethylenically unsaturated acidic compound,
(b) about 5 to about 40 parts by weight water,
(c) about 1 to 10 parts by weight of a functionalized silane compound,
(d) about 0.5 to about 10 parts by weight of an initiator,
(e) from about 2 to about 20 wt % of a non-surface treated filler, and not more than about 20 wt % of other fillers
(f) about 5 to about 40 parts by weight of a solvent other than water, and
(g) about 0 to about 80 parts by weight, of a second ethylenically unsaturated compound being different from component (a);
(ii) mixing the components of step (i) in a manner such that the functionalized silane compound reacts with the non-surface treated filler in-situ in the presence of the ethylenically unsaturated acidic compound to form an acidic dental composition; and
(iii) applying the acidic dental composition to a surface of a tooth.
2. The method of claim 1 , wherein the initiator comprises a sensitising agent.
3. The method of claim 1 , wherein the dental composition further comprises an additive selected from the group consisting of stabilizers, photobleachable colorants, fluoride release agents, and pigments.
4. The method of claim 3 , wherein the additive is present in an amount from about 0 to about 5 parts by weight.
5. The method according to claim 1 , wherein step ii) is continued until a homogeneous dispersion is obtained.
6. The method according to claim 1 , wherein step ii) takes place within a temperature range of about 10° C. to 80° C.
7. The method according to claim 1 , wherein the ethylenically unsaturated acidic compound is characterized by formula (I):
A n -B-C m (I)
wherein A comprises an ethylenically unsaturated group,
B comprises a spacer group, and
C comprises an acidic group, where m and n are each independently selected from 1, 2, 3, 4, 5 or 6, and
wherein the acidic group comprises at least one carboxylic acid residue, phosphoric acid residue, or sulphonic acid residue.
8. The method according to claim 1 , wherein the functionalized silane compound is characterized by formula (II)
A m -B-Si(R 1 ) n (OR 2 ) 3-n (II)
wherein A comprises a polymerizable group,
B comprises a spacer group,
R 1 comprises a C 1 to C 6 alkyl group or a C 6 to C 12 aryl group, and
R 2 comprises a C 1 to C 6 alkyl group,
m is 1, 2, 3 or 4,
and n is 0, 1 or 2.
9. The method according to claim 1 , wherein the functionalized silane compound is selected from the group consisting of 3-(meth)acryloxypropyl trimethoxysilane, 3-(meth)acryloxypropyl triethoxysilane, 3-(meth)acryloxypropyl tris(methoxyethoxy)silane, 3-(meth)acryloxypropenyl trimethoxysilane, (meth)acryloxyethyldimethyl(3-trimethoxysilylpropyl)ammonium chloride, N-(3-(meth)acryloxy-2-hydroxypropyl)-3-aminopropyltriethoxysilane, O-((meth)acryloxyethyl)-N-(triethoxysilylpropyl)urethane, (meth)acryloxymethyl trimethoxysilane, (meth)acryloxymethyl triethoxysilane, methyltrimethoxysilane, ethyltrimethoxysilane, methoxytripropylsilane, propyltriethoxysilane, hexyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri(beta-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, methyltrichlorosilane, phenyltrichlorosilane, trimethylsilyl isocyanate, vinylsilyl triisocyanate and phenylsilyl triisocyanate.
10. The method according to claim 1 , wherein the non-surface treated filler is selected from the group consisting of fumed or precipitated silica, zirconia, titania, silica-zirconia and silica-titania.
11. The method according to claim 1 , wherein the non-surface treated filler has a primary particle size in the range of about 5 nm to about 100 nm.
12. The method according to claim 1 , wherein the dental composition is used for adhering dental restoratives, orthodontic appliances, and/or orthodontic adhesives.
13. The method according to claim 1 , wherein the dental composition is a self-adhesive or self-etching dental material.
14. The method according to claim 1 , wherein a finely dispersed filler is prepared in-situ by reaction of the functionalized silane compound and the non-surface treated filler.
15. The method according to claim 1 , wherein the dental composition has at least one of the following properties:
a) a viscosity below about 3 Pa*s when measured at 23° C. at a shear rate of 1 s −1 24 hours after preparation, or
b) a bond strength to bovine dentin above about 10 MPa when hardened.
16. The method according to claim 1 , wherein the filler is not isolated from the reaction mixture during the silanization.
17. A method using an in-situ silanization process, the method comprising:
(i) providing the following components:
(a) about 3 to about 80 parts by weight of an ethylenically unsaturated acidic compound,
(b) about 5 to about 40 parts by weight water,
(c) about 1 to about 10 parts by weight of a functionalized silane compound,
(d) about 0.5 to about 10 parts by weight of an initiator,
(e) from about 2 to about 20 wt % of a non-surface treated filler, and not more than about 20 wt % of other fillers
(f) about 5 to about 40 parts by weight of a solvent other than water,
(g) about 0 to about 80 parts by weight, of a secong ethylenically unsaturated compound being different from component (a);
(ii) mixing the components of step (i) in a manner such that the functionalized silane compound reacts with the non-surface treated filler in-situ to form an acidic dental composition; and
(iii) applying the acidic dental composition to a surface of a tooth.
18. The method according to claim 17 , wherein the acidic dental composition has at least one of the following properties:
a) a viscosity below about 3 Pa*s when measured at 23° C. at a shear rate of 1 s −1 24 hours after preparation, or
b) a bond strength to bovine dentin above about 10 MPa.
19. The method according to claim 17 , wherein the acidic dental composition is a self-adhesive and/or self-etching composition.