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US 6,284,898 B1Granted
Hydrolysable and polymerizable oxetane silanes
AssigneeIvoclar AG
InventorsNorbert Moszner, Thomas Voelkel, Sabine Stein, Volker Rheinberger
Life of this patent
Estimating the term…
Abstract
Polymerizable and hydrolysable oxetane silanes and in particular silicic acid condensates which can be prepared therefrom are described, which exhibit only a low volume shrinkage on polymerization and produce polymers with high mechanical strength and therefore can be used above all as dental material or constituent thereof.
Claims5
A dental material comprising a polymer of an oxetane silane of the general formula (I) and stereoisomers thereof
- in which the variables R0, R1, R2, R3, R4, R5, R6, X, Y, a, b, c, and x, unless otherwise stated, independently of one another have the following meanings:
- R0=hydrogen or substituted or unsubstituted C1 to C10 alkyl;
- R1=missing or represents substituted or unsubstituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R2=missing or represents substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or C7 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, thioester, carbonyl, amide, and urethane groups or being able to bear these in the terminal position;
- R3=missing or represents substituted or unsubstitituted C1 to C18 alkyl, C2 to C18 alkenyl, C6 to C18 aryl, C7 to C18 alkylaryl, or C7 to C18 arylalkyl, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R4=missing or represents substituted or unsubstituted —CHR6—CHR6, —CHR6—CHR6—S—R5—, —S—R5—, —Y—CO—NH—R5—, or —CO—O—R5—;
- R5=substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C6 to C18 alkylenearylene, or C6 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R6=hydrogen or substituted or unsubstituted C1 to C18 alkyl or C6 to C10 aryl;
- X=a hydrolysable group, namely halogen, hydroxy, alkoxy, or acyloxy;
- Y=O or S;
- a=1, 2, or 3;
- b=1, 2, or 3;
- c=1 or 2;
- and
- x=1, 2, or 3;
- and with the proviso that
- (i) a+x=2, 3, or 4 and
- (ii) a and/or b 1.
15 more elements
A dental material comprising a polymerizable silicic acid condensate of a hydrolysable and polymerizable oxetane silane of the general formula (I) and stereoisomers thereof
- in which the variables R0, R1, R2, R3, R4, R5, R,6, X, Y, a, b, c, and x, unless otherwise stated, independently of one another have the following meanings:
- R0=hydrogen or substituted or unsubstituted C1 to C10 alkyl;
- R1=missing or represents substituted or unsubstituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R2=missing or represents substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or C7 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, thioester, carbonyl, amide, and urethane groups or being able to bear these in the terminal position;
- R3=missing or represents substituted or unsubstitituted C1 to C18 alkyl, C2 to C18 alkenyl, C6 to C18 aryl, C7 to C18 alkylaryl, or C7 to C18 arylalkyl, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R4=missing or represents substituted or unsubstituted —CHR6—CHR6—, —CHR6—CHR6—S—R5—, —S—R5—, —Y—CO—NH—R5—, or —CO—O—R5—;
- R5=substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C6 to C18 alkylenearylene, or C6 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R6=hydrogen or substituted or unsubstituted C1 to C18 alkyl or C6 to C10 aryl;
- X=a hydrolysable group, namely halogen, hydroxy, alkoxy, or acyloxy;
- Y=O or S;
- a=1, 2, or 3;
- b=1, 2, or 3;
- c=1 or 2;
- and
- x=1, 2, or 3;
- and with the proviso that
- (i) a+x=2, 3, or 4 and
- (ii) a and/or b=1.
15 more elements
A method of producing a dental material comprising:
- providing a hydrolysable and polymerizable oxetane silane of the general formula (I) and stereoisomers thereof
- in which the variables R0, R1, R2, R3, R4, R5, R6, X, Y, a, b, c, and x, unless otherwise stated, independently of one another have the following meanings:
- R0=hydrogen or substituted or unsubstituted C1 to C10 alkyl;
- R1=missing or represents substituted or unsubstituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R2=missing or represents substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or C7 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, thioester, carbonyl, amide, and urethane groups or being able to bear these in the terminal position;
- R3=missing or represents substituted or unsubstitituted C1 to C18 alkyl, C2 to C18 alkenyl, C6 to C18 aryl, C7 to C18 alkylaryl, or C7 to C18 arylalkyl, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R4=missing or represents substituted or unsubstituted —CHR6—CHR6—, —CHR6—CHR6—S—R5—, —S—R5—, —Y—CO—NH—R5—, or —CO—O—R5—;
- R5=substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C6 to C18 alkylenearylene, or C6 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R6=hydrogen or substituted or unsubstituted C1 to C18 alkyl or C6 to C10 aryl;
- X=a hydrolysable group, namely halogen, hydroxy, alkoxy, or acyloxy;
- Y=O or S;
- a=1, 2, or 3;
- b=1, 2, or 3;
- c=1 or 2;
- and
- x=1, 2, or 3;
- and with the proviso that
- (i) a+x=2, 3, or 4 and
- (ii) a and/or b=1 and
- polymerizing the oxetane silane under conditions effective to produce the dental material.
17 more elements
A method of producing a dental material comprising:
- providing a polymerizable silicic acid condensate of a hydrolysable and polymerizable oxetane silane of the general formula (I) and stereoisomers thereof
- in which the variables R0, R1, R2, R3, R4, R5, R6, X, Y, a, b, c, and x, unless otherwise stated, independently of one another have the following meanings:
- R0=hydrogen or substituted or unsubstituted C1 to C10 alkyl;
- R1=missing or represents substituted or unsubstituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R2=missing or represents substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C7 to C18 alkylenearylene, or C7 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, thioester, carbonyl, amide, and urethane groups or being able to bear these in the terminal position;
- R3=missing or represents substituted or unsubstitituted C1 to C18 alkyl, C2 to C18 alkenyl, C6 to C18 aryl, C7 to C18 alkylaryl, or C7 to C18 arylalkyl, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R4=missing or represents substituted or unsubstituted —CHR6—CHR6—, —CHR6—CHR6—S—R5—, —S—R5—, —Y—CO—NH—R5—, or —CO—O—R5—;
- R5=substituted or unsubstitituted C1 to C18 alkylene, C6 to C18 arylene, C6 to C18 alkylenearylene, or C6 to C18 arylenealkylene, these radicals being able to be interrupted by at least one group selected from the group consisting of ether, thioether, ester, carbonyl, amide, and urethane groups;
- R6=hydrogen or substituted or unsubstituted C1 to C18 alkyl or C6 to C10 aryl;
- X=a hydrolysable group, namely halogen, hydroxy, alkoxy, or acyloxy;
- Y=O or S;
- a=1, 2, or 3;
- b=1, 2, or 3;
- c=1 or 2;
- and
- x=1, 2, or 3;
- and with the proviso that
- (i) a+x=2, 3, or 4 and
- (ii) a and/or b=1 and
- polymerizing the silicic acid condensate under conditions effective to produce the dental material.
17 more elements
Dependencies are inferred from the claim text.