Granted Patent B2

US 12,465,558 · App. 17/789,379 · Granted Nov 11, 2025

Inventors: Yizhong Wang (Woodbury, MN); Richard P. Rusin (Woodbury, MN); Jie J. Liu (Cottage Grove, MN); Tiffany T. Ton (Woodbury, MN); Carola A. Carrera Vidal (Plymouth, MN); Joel D. Oxman (Minneapolis, MN)

Assignee: Solventum Intellectual Properties Company

A61K6/20A61K6/70A61K6/887

Abstract

Claims (99)

1 . A dental composition comprising:

a silver-fluoride composition comprising:

a source of silver cations,

a source of fluoride anions,

a source of iodide or thiocyanate anions, and water; and

a curable resin composition comprising:

at least one (meth) acrylate monomer.

2 . The dental composition of claim 1 , wherein silver cations are present in an amount of 13-17 wt % with respect to the weight of the silver-fluoride composition.

3 . The dental composition of claim 1 , wherein the fluoride anions are present in an amount of 2.25-3.0 wt % with respect to the weight of the silver-fluoride composition.

4 . The dental composition of claim 1 , comprising:

silver cations and iodide anions in a molar ratio of less than 0.42:1, and

water present in an amount less than 41.2 wt % with respect to the weight of the dental composition.

5 . The dental composition of claim 1 , comprising:

silver cations and thiocyanate anions in a molar ratio of less than 0.37:1, and

water present in an amount less than 57.1 wt % with respect to the weight of the dental composition.

6 . The dental composition of claim 1 , wherein water is present in an amount less than of 45 wt % with respect to the weight of the silver-fluoride composition.

7 . The dental composition of claim 1 , wherein the source of silver cations is selected from silver fluoride, silver chloride, silver nitrate, silver iodide, silver diamine fluoride, and a combination thereof.

8 . The dental composition of claim 1 , wherein the source of fluoride anions is selected from silver fluoride, silver diamine fluoride, sodium fluoride, ammonium fluoride, potassium fluoride, an organic ammonium fluoride, and a combination thereof.

9 . The dental composition of claim 1 , wherein the source of iodide anions is selected from ammonium iodide, sodium iodide, potassium iodide, silver iodide, and a combination thereof, or the source of thiocyanate anions is selected from ammonium thiocyanate, sodium thiocyanate, guanidinium thiocyanate, potassium thiocyanate, silver thiocyanate, and a combination thereof.

10 . The dental composition of claim 1 , the silver-fluoride composition comprising silver iodide, ammonium iodide, and ammonium fluoride.

11 . The dental composition of claim 1 , further comprising a photoinitiator.

12 . The dental composition of claim 11 , wherein the photoinitiator is bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide.

13 . The dental composition of claim 1 , the at least one (meth) acrylate selected from the formulae:

(R a )(R b )C═CH(R 1 )-C(O)—OR 2 (Ib),(R a )(R b )C═CH(R 1 )-C(O)-R 3 -C(O)—CH(R 1 )=C(R a )(R b )(IIb), and (R a )(R b )C═CH(R 1 )-C(O)-R 3 -C(O)-R 4 (IIIb),

wherein:

each R a and each R b is independently —H, or C 1-6 alkyl,

each R 1 is independently —H, C 1-6 alkyl, halogen, or —CN,

R 2 is —H or C 1-12 alkyl,

wherein the C 1-12 alkyl is optionally substituted with one or more-OH, —C(O)OH, and —O—P(O)(OH) 2 ;

each R 3 is independently-O-[R 5 -O-] m -R 6 -[R 5 -O-] m —, —O-[R 5 —O-] n —C(O)N(R 1 )-R 7 —N(R 1 ) C(O)—O-[R 5 —O-] n —, or —O-[R 5 —O-] n —C(O)N(R 1 )-R 7 -N(R 1 ) C(O)—O-R 7 —O—C(O)N(R 1 )-R 7 —N(R 1 ) C(O)—O-[R 5 —O-] n —;

R 4 is —(CH 2 ) n —(CH═CH) p —(CH 2 ) q —C(O)—OR 1 ;

each R 5 is independently a C 2-8 alkylene,

wherein the C 2-8 alkylene is optionally substituted with C 1-4 alkyl, —OH, —OC(O)CH(R 1 )═C(R a )(R b ), or —OC(O)-R 8 ;

R 6 is a bond, C 2-8 alkylene, —Cy-O—, —Ar-O—, or —Ar-R 9 -Ar 2 —O—;

each R 7 is independently C 2-8 alkylene, —Cy-, —Ar 1 —, or —Ar 1 -R 9 -Ar 2 —,

wherein the C 2-8 alkylene is optionally substituted with one or more C 1-4 alkyl and —OH;

R 8 is C 1-12 alkyl, wherein the C 1-12 alkyl is optionally substituted with one or more —OH, —C(O)OH, and —O—P(O)(OH) 2 ;

R 9 is a bond or C 1-6 alkylene optionally substituted with C 1-4 alkyl;

Cy is C 3-8 cycloalkylenyl optionally substituted with one or more C 1-4 alkyl;

Ar 1 is C 6-14 arylene;

Ar 2 is a bond or Ar 1 ;

each m is independently an integer from 0-12;

each n is independently an integer from 1-10; and

o, p, and q are each independently an integer from 0-4.

14 . The dental composition of claim 1 , the at least one (meth) acrylate selected from the formulae:

H 2 C═CH(R 1 )-C(O)—OR 2 (Ia),H 2 C═CH(R 1 )-C(O)-R 3 -C(O)—CH(R 1 )—CH 2 (IIa), and H 2 C═CH(R 1 )-C(O)-R 3 -C(O)-R 4 (IIIa),

wherein:

each R 1 is independently-H or C 1-6 alkyl,

R 2 is —H or C 1-12 alkyl,

wherein the C 1-12 alkyl is optionally substituted with one or more-OH, —C(O)OH, and —O—P(O)(OH) 2 ;

each R 3 is independently-O—[R 5 —O—] m -R 6 -[R 5 —O—] m —, —O—[R 5 —O—] n —C(O)N(R 1 )-R 7 —N(R 1 ) C(O)—O—[R 5 —O—] n —, or —O—[R 5 —O—] n —C(O)N(R 1 )-R 7 -N(R 1 ) C(O)—O-R 7 —O—C(O)N(R 1 )-R 7 —N(R 1 ) C(O)—O—[R 5 —O—],—;

R 4 is —(CH 2 ) n —(CH═CH) p —(CH 2 ) q —C(O)—OR 1 ;

each R 5 is independently a C 2-8 alkylene,

wherein the C 2-8 alkylene is optionally substituted with C 1-4 alkyl, —OH, —OC(O)CH(R 1 )═CH 2 , or —OC(O)-R 8 ;

R 6 is a bond, C 2-8 alkylene, —Cy-O—, —Ar 1 —O—, or —Ar 1 -R 9 -Ar 2 —O—;

each R 7 is independently C 2-8 alkylene, —Cy-, —Ar 1 —, or —Ar 1 -R 9 -Ar 2 —,

wherein the C 2-8 alkylene is optionally substituted with one or more C 1-4 alkyl and —OH;

R 8 is C 1-12 alkyl, wherein the C 1-12 alkyl is optionally substituted with one or more —OH, —C(O)OH, and —O—P(O)(OH) 2 ;

R° is a bond or C 1-6 alkylene optionally substituted with C 1-4 alkyl,

Cy is C 3-8 cycloalkylene optionally substituted with one or more C 1-4 alkyl;

Ar 1 is C 6-14 arylene;

Ar 2 is a bond or Ar 1 ;

each m is independently an integer from 0-12;

each n is independently an integer from 1-10; and

o, p, and q are each independently an integer from 0-4.

15 . The dental composition of claim 1 , the one or more (meth) acrylate monomer is selected from HEMA, Bis —GMA, TEGDMA, GDMA, GDMA succinate, DDMA, PEG400DMA, UDMA, HDMA, and Bis —EMA.

16 . The dental composition of claim 1 , further comprising a resin-modified glass ionomer or a glass ionomer.

17 . The dental composition of claim 1 , further comprising at least one acid-modified (meth) acrylate monomer.

18 . The dental composition of claim 17 , wherein the at least one acid-modified (meth) acrylate monomer is selected from:

(R a )(R b )C-CH(R 1 )-C(O)—OR 2 (Ic),(R a )(R b )C═CH(R 1 )-C(O)-R 3 -C(O)—CH(R 1 )-C(R a )(R b )(IIc), and (R a )(R b )C═CH(R 1 )-C(O)-R 3 -C(O)-R 4 (IIIc),

wherein:

each R a and each R b is independently —H, C 1-6 alkyl, and C 1-6 alkyl substituted with one or more —C(O)OH,

each R 1 is independently —H, C 1-6 alkyl, halogen, —CN, or C 1-6 alkyl substituted with one or more —C(O)OH,

wherein at least one of R 1 , R a , and R b is C 1-6 alkyl substituted with one or more —C(O)OH,

R 2 is —H or C 1-12 alkyl,

wherein the C 1-12 alkyl is optionally substituted with one or more-OH, —C(O)OH, and —O—P(O)(OH) 2 ;

each R 3 is independently-O—[R 5 —O—] m -R 6 -[R 5 —O—] m —, —O—[R 5 —O—] n —C(O)N(R 1 )-R 7 , N(R 1 ) C(O)—O—[R 5 —O—] n —, or —O—[R 5 —O—] n —C(O)N(R 1 )-R 7 -N(R 1 ) C(O)—O-R 7 —O—C(O)N(R 1 )-R 7 —N(R 1 ) C(O)—O—[R 5 —O—] n —;

R 4 is —(CH 2 ) n —(CH═CH) p —(CH 2 ) q —C(O)—OR 1 ;

each R 5 is independently a C 2-8 alkylene,

wherein the C 2-8 alkylene is optionally substituted with C 1-4 alkyl, —OH, —OC(O)CH(R 1 )-C(R a )(R b ), or —OC(O)-R 8 ;

R 6 is a bond, C 2-8 alkylene, —Cy-O—, —Ar 1 —O—, or —Ar 1 -R 9 -Ar 2 —O—;

each R 7 is independently C 2-8 alkylene, —Cy-, —Ar 1 —, or —Ar 1 -R 9 -Ar 2 —,

wherein the C 2-8 alkylene is optionally substituted with one or more C 1-4 alkyl and —OH;

R 8 is C 1-12 alkyl, wherein the C 1-12 alkyl is optionally substituted with one or more —OH, —C(O)OH, and —O—P(O)(OH) 2 ;

R 9 is a bond or C 1-6 alkylene optionally substituted with C 1-4 alkyl;

Cy is C 3-8 cycloalkylenyl optionally substituted with one or more C 1-4 alkyl;

Ar 1 is C 6-14 arylene;

Ar 2 is a bond or Ar 1 ;

each m is independently an integer from 0-12;

each n is independently an integer from 1-10; and

o, p, and q are each independently an integer from 0-4.

19 . A kit comprising:

a dental composition of claim 1 ; and

a set of instructions directing a user to:

contact the dental composition to a tooth surface, and apply light at a wavelength from about 250 nm to about 700 nm to the dental composition on the tooth surface.

20 . A method of repairing a tooth surface, the method comprising:

providing a dental composition of claim 1 ;

contacting the dental composition to the tooth surface; and

applying light at a wavelength from about 250 nm to about 700 nm to the dental composition on the tooth surface.

Assignments (2)

Continuity (3)

References Cited (27)