Substituted saccharide compounds and dental compositions
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A61K-006/083
C07C-233/20
출원번호
US-0813673
(2011-08-19)
등록번호
US-8557893
(2013-10-15)
국제출원번호
PCT/US2011/048383
(2011-08-19)
§371/§102 date
20130201
(20130201)
국제공개번호
WO2012/036838
(2012-03-22)
발명자
/ 주소
Yang, Jie
Mitra, Sumita B.
He, Yi
Shukla, Brian A.
Karim, Naimul
Falsafi, Afshin
Ross, Richard B.
Klaiber, Paul R.
Griesgraber, George W.
출원인 / 주소
3M Innovative Properties Company
대리인 / 주소
Fischer, Carolyn A.
인용정보
피인용 횟수 :
0인용 특허 :
26
초록▼
Substituted saccharide compounds, dental compositions comprising substituted saccharide compounds, and methods of using dental compositions are described. In one embodiment, the substituted saccharide amide compound comprises a hydrophobic group and at least one free-radically polymerizable group wi
Substituted saccharide compounds, dental compositions comprising substituted saccharide compounds, and methods of using dental compositions are described. In one embodiment, the substituted saccharide amide compound comprises a hydrophobic group and at least one free-radically polymerizable group with the proviso that the hydrophobic group is not bonded to the ethylenically unsaturated carbon atom of the free-radically polymerizable group. The hydrophobic group is typically bonded to a nitrogen atom of a saccharide amine residue or a carbonyl moiety of saccharide amide residue.
대표청구항▼
1. A substituted saccharide amide compound having the formula R3OCHH2CHOR3CH2NR1R2 wherein R1 is a hydrophobic group;R2 is a free-radically polymerizable group;R3 is independently hydrogen or an acidic group and at least one of the R3 groups is an acidic group; andand n is an integer ranging from 1
1. A substituted saccharide amide compound having the formula R3OCHH2CHOR3CH2NR1R2 wherein R1 is a hydrophobic group;R2 is a free-radically polymerizable group;R3 is independently hydrogen or an acidic group and at least one of the R3 groups is an acidic group; andand n is an integer ranging from 1 to 4. 2. The substituted saccharide compound of claim 1 wherein hydrophobic group renders the substituted saccharide compound sufficiently lipophilic such that the substituted saccharide amide compound has an HLB decrease of at least 2 relative to the same unsubstituted saccharide amide compound. 3. A substituted saccharide compound having the general formula wherein R1 is a hydrophobic group;R4 is independently hydrogen, an acidic group, or -L-R2 wherein L is a linking group and R2 is a free-radically polymerizable group with the proviso that at least one R4 is -L-R2;R5 is hydrogen or a C1-C4 alkyl group; andand n is an integer ranging from 1 to 4. 4. The substituted saccharide compound of claim 3 wherein at least two R4 groups are -L-R2. 5. A substituted saccharide compound having the general formula wherein one of R6-R10 is wherein R5 is hydrogen or a C1-C4 alkyl group and R1 is a hydrophobic group; at least one of R6-R10 is O-L-R2, wherein O is oxygen, L is a linking group, and R2 is a free-radically polymerizable group; andthe remaining R6-R10 are OH or an acidic group. 6. The substituted saccharide compound of claim 5 wherein at least two of R6-R10 are O-L-R2. 7. The substituted saccharide compound of claim 5 wherein the remaining R6—R10 are OH. 8. The substituted saccharide compound of claim 1 wherein the hydrophobic group is a C5 to C26 alkyl group. 9. The saccharide compound of claim 1 wherein the free-radically polymerizable group is a (meth)acrylate group. 10. The saccharide compound of claim 3 wherein at least one R4 is an acidic groups selected from phosphoric, phosphonic, sulfuric, and carboxylic acidic groups. 11. A polymerizable dental composition comprising the substituted saccharide amide compound according to claim 1. 12. The polymerizable dental composition of claim 11 wherein the dental composition further comprises at least one other ethylenically unsaturated monomer selected from ethylenically unsaturated compounds with acid functionality, ethylenically unsaturated compounds without acid functionality, and combinations thereof. 13. The polymerizable dental composition of claim 11 wherein the dental composition is free of ethylenically unsaturated monomer derived from bisphenol A. 14. The polymerizable dental composition of claim 11 wherein the composition is suitable for use as a sealant, adhesive, cement, flowable composite restoration, or dental restoration material. 15. The dental restoration material of claim 14 further comprising at least 40 wt-% of nanocluster filler. 16. The substituted saccharide compound of claim 3 wherein the substituted saccharide compound comprises at least two free-radically polymerizable groups. 17. A substituted saccharide compound of claim 3 wherein the compound is 18. The substituted saccharide compound of claim 8 wherein the hydrophobic group is an alkyl group comprising at least 6 carbon atoms. 19. The substituted saccharide compound of claim 9 wherein the (meth)acrylate group is bonded to the saccharide amide via a urethane linkage. 20. The saccharide compound of claim 5 wherein at least one R6-R10 is an acidic group selected from phosphoric, phosphonic, sulfuric, and carboxylic acidic groups. 21. The saccharide compound of claim 1 wherein the acidic group is selected from phosphoric, phosphonic, sulfuric, and carboxylic acidic groups. 22. The saccharide compound of claim 1 wherein the compound is 23. The substituted saccharide compound of claim 3 wherein hydrophobic group renders the substituted saccharide compound sufficiently lipophilic such that the substituted saccharide amide compound has an HLB decrease of at least 2 relative to the same unsubstituted saccharide amide compound. 24. The substituted saccharide compound of claim 3 wherein the hydrophobic group is a C5 to C26 alkyl group. 25. The substituted saccharide compound of claim 24 wherein the hydrophobic group is an alkyl group comprising at least 6 carbon atoms. 26. The saccharide compound of claim 3 wherein the free-radically polymerizable group is a (meth)acrylate group. 27. The substituted saccharide compound of claim 26 wherein the (meth)acrylate group is bonded to the saccharide amide via a urethane linkage. 28. A polymerizable dental composition comprising the substituted saccharide amide compound according to claim 3. 29. The polymerizable dental composition of claim 28 wherein the dental composition further comprises at least one other ethylenically unsaturated monomer selected from ethylenically unsaturated compounds with acid functionality, ethylenically unsaturated compounds without acid functionality, and combinations thereof. 30. The polymerizable dental composition of claim 28 wherein the dental composition is free of ethylenically unsaturated monomer derived from bisphenol A. 31. The polymerizable dental composition of claim 28 wherein the composition is suitable for use as a sealant, adhesive, cement, flowable composite restoration, or dental restoration material. 32. The dental restoration material of claim 31 further comprising at least 40 wt-% of nanocluster filler. 33. The substituted saccharide compound of claim 5 wherein hydrophobic group renders the substituted saccharide compound sufficiently lipophilic such that the substituted saccharide amide compound has an HLB decrease of at least 2 relative to the same unsubstituted saccharide amide compound. 34. The substituted saccharide compound of claim 5 wherein the hydrophobic group is a C5 to C26 alkyl group. 35. The substituted saccharide compound of claim 34 wherein the hydrophobic group is an alkyl group comprising at least 6 carbon atoms. 36. The saccharide compound of claim 5 wherein the free-radically polymerizable group is a (meth)acrylate group. 37. The substituted saccharide compound of claim 36 wherein the (meth)acrylate group is bonded to the saccharide amide via a urethane linkage. 38. The substituted saccharide compound of claim 5 wherein the substituted saccharide compound comprises at least two free-radically polymerizable groups. 39. A polymerizable dental composition comprising the substituted saccharide amide compound according to claim 5. 40. The polymerizable dental composition of claim 39 wherein the dental composition further comprises at least one other ethylenically unsaturated monomer selected from ethylenically unsaturated compounds with acid functionality, ethylenically unsaturated compounds without acid functionality, and combinations thereof. 41. The polymerizable dental composition of claim 39 wherein the dental composition is free of ethylenically unsaturated monomer derived from bisphenol A. 42. The polymerizable dental composition of claim 39 wherein the composition is suitable for use as a sealant, adhesive, cement, flowable composite restoration, or dental restoration material. 43. The dental restoration material of claim 42 further comprising at least 40 wt-% of nanocluster filler. 44. A substituted saccharide compound of claim 5 wherein the compound is
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