Dental adhesive composites

Claim 2

An adhesive dental restorative composite coating material to be coated over a dry tooth surface by flowing it onto the surface and that is easily rearranged on the tooth surface without pressure after application and prior to curing, comprising a suspension consisting essentially of from 40% to 70% inorganic filler fibers having a hardness on the Mohs scale of 3.5 to 6 by weight of said composite in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity of less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and having (a) diameters of from 1/20 to 1/5 their said lengths, respectively, and a peroxide catalyst and an accelerator for said resin, said composite coating material being selfcuring in place to form a cured hardened coating.

Claim 3

An adhesive dental restorative composite coating material comprising a suspension consisting essentially of from 40% to 70% filler fibers of calcium silicate by weight of said composite in a liquid acrylate or substituted acrylate resin composition, said resin composition having a viscosity of less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and having diameters of from 1/20 to 1/5 their lengths, respectively, and a peroxide catalyst and an accelerator for said resin.

Claim 4

An adhesive dental restorative composite coating material comprising a suspension consisting essentially of from 40% to 70% filler fibers of calcium silicate by weight of said composite in a liquid acrylate or substituted acrylate resin composition, said resin composition having a viscosity of less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and having diameters of from 1/20 to 1/5 their lengths, respectively, and a peroxide catalyst and an accelerator for said resin.

Claim 5

An adhesive dental restorative composite coating material to be coated over a dry tooth surface that has been roughened by a conditioning treatment, by flowing it onto the surface, comprising a suspension that is easily rearranged on the tooth surface without pressure after application and prior to curing, consisting essentially of from 40% to 70% by weight of the coating material of filler fibers having a hardness on the Mohs scale of 3.5 to 6 in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and (a) having diameters of from 1/20 to 1/5 their said lengths respectively, said resin composition comprising from about 25% to about 90% by weight of (A) a compound of the formula: ##STR22## wherein R 1 is hydrogen or alkyl of 1 to 4 carbons; R is: ##STR23## wherein x is an integer of 1 to 5, and R 2 is hydrogen or an alkyl of 1 to 4 carbon atoms; (b) -- CH 2 (CH 2 ) y CH 2 O -- wherein y is an integer of 1 or 2; ##STR24## ##STR25## wherein R 3 is OH or ##STR26## and R 1 has the same meaning as above; and 10% to 75% by weight of (B), an aromatic or alicyclic polyacrylate, and small but effective amounts of a peroxide-type catalyst and of an accelerator, said coating material being self-curing in place to form a cured hardened coating.

Claim 6

An adhesive dental restorative composite coating material to be coated over a dry tooth surface that has been roughened by a conditioning treatment, by flowing it onto the surface, comprising a suspension that is easily rearranged on the tooth surface without pressure after application and prior to curing, consisting essentially of from 40% to 70% by weight of the coating material of filler fibers having a hardness on the Mohs scale of 3.5 to 6 in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and (a) having diameters of from 1/20 to 1/5 their said lengths respectively, said resin composition comprising from about 25% to about 90% by weight of (A) a compound of the formula: ##STR22## wherein R 1 is hydrogen or alkyl of 1 to 4 carbons; R is: ##STR23## wherein x is an integer of 1 to 5, and R 2 is hydrogen or an alkyl of 1 to 4 carbon atoms; (b) -- CH 2 (CH 2 ) y CH 2 O -- wherein y is an integer of 1 or 2; ##STR24## ##STR25## wherein R 3 is OH or ##STR26## and R 1 has the same meaning as above; and 10% to 75% by weight of (B), an aromatic or alicyclic polyacrylate, and small but effective amounts of a peroxide-type catalyst and of an accelerator, said coating material being self-curing in place to form a cured hardened coating.

Claim 7

A composite coating material in accordance with claim 3 wherein R is (a), R 1 is methyl, and R 2 is hydrogen.

Claim 8

A composite coating material in accordance with claim 3 wherein B is a diaromatic diacrylate.

Claim 9

A composite coating material in accordance with claim 4 wherein B is a diaromatic diacrylate.

Claim 10

A composite coating material in accordance with claim 3 wherein B is bisphenol-A-bis(3-methacrylato-2-hydroxypropyl) ether.

Claim 11

A composite coating material in accordance with claim 4 wherein B is bisphenol-A-bis(3-methacrylato-2-hydroxypropyl) ether.

Claim 12

A composite coating material in accordance with claim 4 wherein A is triethyleneglycol dimethacrylate.

Claim 13

A composite coating material in accordance with claim 8 wherein A is triethyleneglycol dimethacrylate.

Claim 14

An adhesive dental restorative composite coating material comprising a suspension consisting essentially of from 40% to 70% by weight of calcium silicate filler fibers in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and having diameters of from 1/20 to 1/5 their said lengths, respectively, said resin composition comprising from about 25% to about 90% by weight of (A) a compound of the formula: ##STR27## wherein R 1 is hydrogen or alkyl of 1 to 4 carbons; R is: ##STR28## wherein x is an integer of 1 to 5, and R 2 is hydrogen or an alkyl of 1 to 4 carbon atoms; (b)--CH 2 (CH 2 ) y CH 2 O-- wherein y is an integer of 1 or 2; ##STR29## ##STR30## wherein R 3 is OH or ##STR31## and R 1 has the same meaning as above; and 10% to 75% by weight of (B), an aromatic or alicyclic polyacrylate, and small but effective amounts of a peroxide-type catalyst and of an accelerator, said coating material being self-curing in place to form a cured hardened coating.

Claim 15

An adhesive dental restorative composite coating material comprising a suspension consisting essentially of from 40% to 70% by weight of calcium silicate filler fibers in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity less than 5,000 centipoises, said fibers being from 1 to 100 microns in length and having diameters of from 1/20 to 1/5 their said lengths, respectively, said resin composition comprising from about 25% to about 90% by weight of (A) a compound of the formula: ##STR27## wherein R 1 is hydrogen or alkyl of 1 to 4 carbons; R is: ##STR28## wherein x is an integer of 1 to 5, and R 2 is hydrogen or an alkyl of 1 to 4 carbon atoms; (b)--CH 2 (CH 2 ) y CH 2 O-- wherein y is an integer of 1 or 2; ##STR29## ##STR30## wherein R 3 is OH or ##STR31## and R 1 has the same meaning as above; and 10% to 75% by weight of (B), an aromatic or alicyclic polyacrylate, and small but effective amounts of a peroxide-type catalyst and of an accelerator, said coating material being self-curing in place to form a cured hardened coating.

Claim 16

An adhesive dental restorative composite coating material comprising a suspension consisting essentially of 40% to 70% by weight calcium silicate filler fibers in a liquid resin composition, said fibers being 1 to 100 microns in length and from 1/20 to 1/5 said length in diameter, said fibers having an average length of 5.5 microns, 97% by weight of said fibers having a length less than 20 microns, and 94% by weight of said fibers having a length less than 10 microns, said resin composition comprising from 30% to 70% by weight triethyleneglycol dimethacrylate and from 70% to 30% by weight of bisphenol-A-bis(3-methacrylato-2-hydroxpropyl) ether and having a viscosity not greater than 5,000 centipoises, and a peroxide catalyst and amine accelerator for said composition.

Claim 17

An adhesive dental restorative composite coating material comprising a suspension consisting essentially of 40% to 70% by weight calcium silicate filler fibers in a liquid resin composition, said fibers being 1 to 100 microns in length and from 1/20 to 1/5 said length in diameter, said fibers having an average length of 5.5 microns, 97% by weight of said fibers having a length less than 20 microns, and 94% by weight of said fibers having a length less than 10 microns, said resin composition comprising from 30% to 70% by weight triethyleneglycol dimethacrylate and from 70% to 30% by weight of bisphenol-A-bis(3-methacrylato-2-hydroxpropyl) ether and having a viscosity not greater than 5,000 centipoises, and a peroxide catalyst and amine accelerator for said composition.

Claim 18

A composite coating material in accordance with claim 12 wherein said fibers comprise about 55% by weight of said composite, said resin composition comprises about 40% by weight of triethyleneglycol dimethacrylate and 60% by weight of bisphenol-A-bis(3-methacrylato-2-hydroxypropyl) ether, and said accelerator is N-bis(2-hydroxyethyl)-p-toluidine and said catalyst is benzoyl peroxide.

Claim 19

A dental restorative coating material to be coated over a dry tooth surface that has been roughened by a conditioning treatment, by flowing it onto the surface, that can be easily rearranged without the use of pressure after application and prior to curing, and that consists essentially of a flowable suspension of from 40% to 70% by weight of said suspension of filler fibers in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity of less than 5,000 centipoises, said resin comprising from about 25% to about 90% by weight of (A) a compound of the formula: ##STR32## wherein R 1 is hydrogen or alkyl of 1 to 4 carbons; R is: ##STR33## wherein x is an integer of 1 to 5, and R 2 is hydrogen or an alkyl of 1 to 4 carbon atoms; (b) -- CH 2 (CH 2 ) y CH 2 O -- wherein y is an integer of 1 or 2; ##STR34## and R 1 has the same meaning as above; and 10% to 75% by weight of (B), an aromatic or alicyclic polyacrylate selected from the group consisting of ##STR35## wherein each of X and X 1 may independently be hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms, or halogen: ##STR36## where X has the meaning above: ##STR37## wherein X 1 , X 2 , and X 3 are either hydrogen or lower alkyl groups comprising 4 or less carbon atoms; ##STR38## where, in the three preceding formulae, X is hydrogen, lower alkyl, or halogen; ##STR39## where X is selected from ##STR40## and X 1 is hydrogen, lower alkyl, or halogen; said fibers being from 1 to 100 microns in length and having diameters of from 1/20 to 1/5 their lengths, respectively, said coating material also containing small but effective amounts of a peroxide-type catalyst and of an accelerator, and being capable of flowing onto the roughened tooth surface to form tag-like extensions in openings in the roughened tooth surface, and being self-curing in place to form a cured, hardened coating on the tooth surface.

Claim 20

A dental restorative coating material to be coated over a dry tooth surface that has been roughened by a conditioning treatment, by flowing it onto the surface, that can be easily rearranged without the use of pressure after application and prior to curing, and that consists essentially of a flowable suspension of from 40% to 70% by weight of said suspension of filler fibers in a liquid acrylate or substituted acrylate resin composition, said resin having a viscosity of less than 5,000 centipoises, said resin comprising from about 25% to about 90% by weight of (A) a compound of the formula: ##STR32## wherein R 1 is hydrogen or alkyl of 1 to 4 carbons; R is: ##STR33## wherein x is an integer of 1 to 5, and R 2 is hydrogen or an alkyl of 1 to 4 carbon atoms; (b) -- CH 2 (CH 2 ) y CH 2 O -- wherein y is an integer of 1 or 2; ##STR34## and R 1 has the same meaning as above; and 10% to 75% by weight of (B), an aromatic or alicyclic polyacrylate selected from the group consisting of ##STR35## wherein each of X and X 1 may independently be hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms, or halogen: ##STR36## where X has the meaning above: ##STR37## wherein X 1 , X 2 , and X 3 are either hydrogen or lower alkyl groups comprising 4 or less carbon atoms; ##STR38## where, in the three preceding formulae, X is hydrogen, lower alkyl, or halogen; ##STR39## where X is selected from ##STR40## and X 1 is hydrogen, lower alkyl, or halogen; said fibers being from 1 to 100 microns in length and having diameters of from 1/20 to 1/5 their lengths, respectively, said coating material also containing small but effective amounts of a peroxide-type catalyst and of an accelerator, and being capable of flowing onto the roughened tooth surface to form tag-like extensions in openings in the roughened tooth surface, and being self-curing in place to form a cured, hardened coating on the tooth surface.

Claim 21

A method for repairing a defect in the surface of a tooth which comprises flowing on the tooth surface where said defect occurs an initially liquid, settable adhesive dental restorative composite as defined in claim 1 that is easily rearranged on the tooth surface without pressure after application and prior to curing, and permitting said composite to harden in situ on the tooth surface.

Claim 22

A method as claimed in claim 15 wherein a portion of said liquid resin composition and fibers containing the peroxide catalyst and free of accelerator, is applied to the tooth surface including said defect first, and the remaining portion of said liquid resin composition and fibers, with said accelerator, is then applied over said catalyst-containing portion.

Claim 23

A method of repairing a defect in the surface of a tooth which comprises flowing on the tooth surface including said defect an initially liquid, settable adhesive dental restorative composite as defined in claim 3 that is easily rearranged on the tooth surface without pressure after application and prior to curing, and permitting said composite to harden in situ on the tooth.

Claim 24

A method for repairing a defect in the surface of a tooth that comprises flowing on the tooth surface where said defect occurs an initially liquid, self-curing adhesive dental restorative composite as defined in claim 2, that is easily rearranged on the tooth surface without pressure after application and prior to curing, and then permitting the composite to harden in situ on the tooth surface.

Claim 25

A method for repairing a defect in the surface of a tooth that comprises flowing on the tooth surface where said defect occurs an initially liquid, self-curing adhesive dental restorative composite in accordance with claim 11, that is easily rearranged on the tooth surface without pressure after application and prior to curing, and permitting said composite to harden in situ on the tooth surface.

Claim 26

A method for repairing a defect in the surface of a tooth that comprises flowing on the tooth surface where the defect occurs an initially liquid, self-curing adhesive dental restorative composite in accordance with claim 12, that is easily rearranged on the tooth surface without pressure after application and prior to using, and permitting said composite to harden in situ on the tooth surface.

Claim 27

A method in accordance with claim 20, wherein said fibers comprise about 55% by weight of said composite, said resin composition comprises about 40% by weight of triethyleneglycol dimethacrylate and 60% by weight of bisphenol-A-bis(3-methacrylate-2-hydroxypropyl) ether, and said accelerator is N-bis(2-hydroxyethyl)-p-toluidine and said catalyst is benzoyl peroxide.

Claim 28

A method for repairing a defect in the surface of a tooth that comprises flowing on the tooth surface where the defect occurs an initially liquid, self-curing adhesive dental restorative composite in accordance with claim 14, and permitting said composite to harden in situ on the tooth surface.

Claim 31

A method as claimed in claim 23 wherein said accelerator is N-bis(hydroxyethyl)-p-toluidine and said catalyst is benzoyl peroxide.

Claim 32

A method as claimed in claim 24 wherein 0.70% benzoyl peroxide is employed and about 3% of N-bis(hydroxyethyl)-p-toluidine.

Claim 33

A method as claimed in claim 24 wherein said resin composition comprises about 40% by weight triethyleneglycol dimethacrylate and about 60% by weight bisphenol-A-bis(3-methacrylato-2-hydroxypropyl) ether.