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US 8,513,326 B2Granted
Carbamate-methacrylate monomers and their use in dental applications
AssigneeSeptodont Confi-Dental
InventorsMarianela Trujillo-Lemon, Kristin Lindsay Wall, Kristina Esquibel, Jordan Boulden, Amy J. Docktor, Zachary R. Shelton, Cora Bracho-Troconis
Life of this patent
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Abstract
The present invention relates, generally, to monomers containing carbamate-methacrylates or derivatives of carbamate-methacrylates, processes for making the monomers, and compositions comprising the monomers. The present invention also relates to methods of using the monomers, such as in dental applications, and in particular, dental restorative resins.
Claims26
A compound of formula (I):
- wherein:
- the ring structure of formula (I) is saturated or contains up to three unsaturations;
- Y1-Y6, each independent from each other, is selected from the group consisting of:
- C, O, N, and S, wherein at least one of Y1-Y6 is O, N, or S, with the proviso that at least two of Y1-Y6 is C, and wherein:
- (i) when any one of Y1-Y6 is O, S, or an unsaturated nitrogen, then the corresponding H, X1-X6 and Z1-Z6 are absent, and
- ii) when any one of Y1-Y6 is a saturated nitrogen or an unsaturated carbon, then the corresponding H is absent;
- X1-X6, each independent from each other, is a direct bond, or is selected from the group consisting of:
- ═O, ═S, and Rx,
- wherein Rx is a C1-C10 group optionally having at least one unsaturation, branch and/or cycle, which is substituted up to 4 times or unsubstituted, and which may be interrupted by at least one O or S, wherein the substituents are each independently selected from the group consisting of —OH, —OR, ═O, ═S, —O2CR, —SH, —SR, —SOCR, —NH2, —NHR, —N(R)2, —NHCOR, —NRCOR, l, —Br, —Cl, —F, —CN, —CO2H, —CO2R, —CHO, —COR, —CONH2, —CONHR, —CON(R)2, —COSH, —COSR, —NO2, —SO3H, —SOR, and —SO2R, wherein R is a linear, branched or cyclic alkyl of one to ten carbon atoms,
- Z1-Z6, each independent from each other, is selected from the group consisting of:
- (a) H;
- (b) a radical of formula (II):
- wherein:
- R1 is selected from the group consisting of:
- H and Rx, as described above,
- R2 is Rx, as described above;
- n is an integer from 1 to 10,
- A1 is a direct bond or Rx, as described above;
- and
- A2 is selected from the group consisting of O and NH;
- (c) a radical of formula (V)
- wherein Ry is selected from the group consisting of H, CH3, CH2CH3, C(CH3)3, OH, COOH, anhydride, O═P(OH)2, and ═P(CH2)m(OH)2, wherein m=1 to 4;
- and
- (d) a radical of formula (VI):
- wherein Ry is as described above;
- with the proviso that at least two of Z1-Z6 is independently a radical of formula, (V) or (VI);
- and wherein when any one of X1-X6 is H, ═O, or ═S, then the respective Z1-Z6 is absent.
24 more elements
A compound of formula (III):
- R1 is selected from the group consisting of:
- H and Rx, wherein Rx is a C1-C10 group optionally having at least one unsaturation, branch or cycle, which is substituted up to 4 times or unsubstituted and which may be interrupted by at least one O or S, wherein the substituents are each independently selected from the group consisting of —OH, —OR, ═O, ═S, —O2CR, —SH, —SR, —SOCR, —NH2, —NHR, —N(R)2, —NHCOR, —NRCOR, —I, —Br, —Cl, —F, —ON, —CO2H, —CO2R, —CHO, —COR, —CONH2, —CONHR, —CON(R)2, —COSH, —COSR, —NO2, —SO3H, —SOR, and —SO2R, wherein R is a linear, branched or cyclic alkyl of one to ten carbon atoms,
- and wherein each R1 in formula (III) may be the same or different;
- R2 is Rx, as defined above, or a C9-C25 group optionally having at least one unsaturation, branch or cycle, which is substituted up to 4 times or unsubstituted and which may be interrupted by at least one O or S, wherein the substituents are each independently selected from the group consisting of —OH, —OR, ═O, ═S, —O2CR, —SH, —SR, —SOCR, —NH2, —NHR, —N(R)2, —NHCOR, —NRCOR, —I, —Br, —Cl, —F, —ON, —CO2H, —CO2R, —CHO, —COR, —CONH2, —CONHR, —CON(R)2, —COSH, —COSR, —NO2, —SO3H, SOR, and —SO2R, wherein R is a linear, branched or cyclic alkyl of one to ten carbon atoms, wherein each R2 in formula (III) may be the same or different, and wherein at least one R2 group comprises an aromatic group;
- R3 is a C6-C50 group optionally having at least one unsaturation, branch or cycle, which is substituted up to 4 times or unsubstituted and which may be interrupted by at least one O or S, wherein the substituents are each independently selected from the group consisting of —OH, —OR, ═O, ═S, —O2CR, —SH, —SR, —SOCR, —NH2, —NHR, —N(R)2, —NHCOR, —NRCOR, —I, —Br, —Cl, —F, —ON, —CO2H, —CO2R, —CHO, —COR, —CONH2, CONHR, —CON(R)2, —COSH, —COSR, —NO2, —SO3H, —SOR, and —SO2R, wherein R is a linear, branched or cyclic alkyl of one to ten carbon atoms
- n is an integer from 1 to 10;
- A1 is a direct bond or Rx, as described above;
- and
- A2 is selected from the group consisting of O and NH,
- wherein the compound of formula (III) is selected from the group consisting of
7 more elements
Dependencies are inferred from the claim text.