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US 11,446,215 B2Granted
Macromonomer based light-curable dental impression material
AssigneeDENTSPLY SIRONA Inc.
InventorsXiaoming Jin, Yi Liu, Stefano Gulmini, Stefano Cavaliere, Zhaonan Zhang
Life of this patent
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Abstract
A light-curable dental impression material comprising (a) a polymerizable polysiloxane resin composition comprising compounds of formula (I) E−(L1−Z)n−L2−E (I) (b) a particulate filler; and (c) a photoinitiator.
Claims6
A light-curable dental impression material having improved shore hardness and improved tear strength, said impression material comprising:
- A. a polymerizable polysiloxane resin mixture obtained by a process comprising steps of:
- (a) treating an impure diol compound of formula (Xa)
- HO-L4(OH) (Xa)
- wherein
- L4 is a polysiloxane group of the formula (VIIIa)
- wherein
- R1# is an alkylene having 1 to 8 carbon atoms;
- R2# is an alkyl having from 1 to 4 carbon atoms;
- and
- y# is an integer from 5 to 20;
- with a solid acid absorbent material to obtain purified compound of formula (Xa),
- wherein the purified compound of formula Xa has a total acid value of from 0.02-0.06 mg KOH/g,
- (b) reacting a mixture comprising:
- (i) x equivalents of purified compound of formula (Xa) and one or more di or polyol compounds of the following formula
- HO—L4″(OH)l″ (Xa′)
- wherein
- L4″ is an (l″+1)-valent linker group;
- and
- I″ is an integer of from 1 to 5,
- (ii) y equivalents of one or more compounds of a following formula (XI):
- OCN−L3NCO (XI)
- wherein
- L3 is a divalent linker group of Formula (VI)
- wherein
- Ra1 and Ra2 which may be a same or different, independently represent a hydrogen atom, a C1-6 linear or branched alkyl group, a C4-10 aryl group, a polymerizable double bond containing organic residue, a group of the following formula [−X″L″]mRa3, wherein X″ represents O, S, or NRa4 wherein Ra4 represents a hydrogen atom, an organic residue containing a polymerizable double bond, a linear or branched C1-6 alkyl group, or a C4-10 aryl group, L″ represents a C1-6 linear or branched alkyl group, a C4-10 aryl group, or a SiRa52 group wherein Ra5 which may be a same or different, independently represent an organic residue containing a polymerizable double bond, or a C1-4 alkyl group, m is an integer from 1 to 20, and Ra3 is an organic residue containing a polymerizable double bond, a C1-4 alkyl group, or a C4-10 aryl group ;
- and
- (iii) z equivalents of one or more compounds of a following formula (XII):
- wherein
- R1 represents a hydrogen atom or a C1-12 alkyl group;
- X3 represents an oxygen atom, a sulfur atom or a group NR2, wherein R2 is a hydrogen atom, C1-12 alkyl group, or an allyl group;
- L5 is a divalent hydrocarbon linker group;
- X4 represents an oxygen atom, a sulfur atom or a group NR3, wherein R3 is a hydrogen atom, or a C1-12 alkyl group;
- and
- a represents an integer of from 1 to 20,
- wherein 0.05≤x/y≤0.66,
- wherein x, y and z are the molar equivalents of component (a), (b) and (c);
- to form the polymerizable polysiloxane resin mixture;
- B. a particulate filler;
- and
- C. a photoinitiator.
37 more elements
A polymerizable polysiloxane resin mixture obtained by a process comprising steps of:
- (a) treating an impure diol compound of formula (Xa)
- HO-L4(OH) (Xa)
- wherein
- L4 is a polysiloxane group of the formula (VIIIa)
- wherein
- R1# is an alkylene having 1 to 8 carbon atoms;
- R2# is an alkyl having from 1 to 4 carbon atoms;
- and
- y# is an integer from 5 to 20;
- with a solid acid absorbent material to obtain purified compound of formula (Xa),
- wherein the purified compound of formula Xa has a total acid value of from 0.02-0.06 mg KOH/g,
- (b) reacting a mixture comprising:
- (i) x equivalents of purified compound of formula (Xa) and one or more di or polyol compounds of the following formula
- HO-L4″(OH)l″ (X)
- wherein
- L4″ is an (l″+1)-valent linker group;
- and
- l″ is an integer of from 1 to 5,
- (ii) y equivalents of one or more compounds of a following formula (XI):
- OCN-L3NCO (XI)
- wherein
- L3 is a divalent linker group of Formula (VI)
- wherein
- Ra1 and Ra2 which may be a same or different, independently represent a hydrogen atom, a C1-6 linear or branched alkyl group, a C4-10 aryl group, a polymerizable double bond containing organic residue, a group of the following formula [—X″L″]mRa3, wherein X″ represents O, S, or NRa4 wherein Ra4 represents a hydrogen atom, an organic residue containing a polymerizable double bond, a linear or branched C1-6 alkyl group, or a C4-10 aryl group, L″ represents a C1-6 linear or branched alkyl group, a C4-10 aryl group, or a SiRa52 group wherein Ra5 which may be a same or different, independently represent an organic residue containing a polymerizable double bond, or a C1-4 alkyl group, m is an integer from 1 to 20, and Ra3 is an organic residue containing a polymerizable double bond, a C1-4 alkyl group, or a C4-10 aryl group ;
- and
- (iii) z equivalents of one or more compounds of a following formula (XII):
- wherein
- R1 represents a hydrogen atom or a C1-12 alkyl group;
- X3 represents an oxygen atom, a sulfur atom or a group NR2, wherein R2 is a hydrogen atom, C1-12 alkyl group, or an allyl group;
- L5 is a divalent hydrocarbon linker group;
- X4 represents an oxygen atom, a sulfur atom or a group NR3, wherein R3 is a hydrogen atom, or a C1-12 alkyl group;
- and
- a represents an integer of from 1 to 20,
- wherein 0.05≤x/y≤0.66,
- wherein x, y and z are the molar equivalents of component (a), (b) and (c);
- to form the polymerizable polysiloxane resin mixture for use in a light-curable dental impression material.
33 more elements
Dependencies are inferred from the claim text.