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US 5,596,025 AGranted
Dental impression material with cure-indicating dye
AssigneeMinnesota Mining and Manufacturing Company
InventorsJoel D. Oxman, Mark S. Konings, George V. D. Tiers, Kim M. Vogel, Dennis E. Vogel
Life of this patent
Estimating the term…
Abstract
The present invention provides novel dental impression materials, the cure of which can be monitored visually, comprising: (1) a curable silicone polymer; (2) a crosslinker compound containing silicon-bonded-hydrogen groups; (3) a hydrosilation catalyst; and (4) one or more cure-indicating dyes that exhibit a color change in the presence of a silicon-bonded-hydrogen compound and a hydrosilation catalyst. The cure-indicating dye provides the composition with an initial pre-cure color and a different post-cure color. As a result of this change in color, the state of cure of the impression material can be visually monitored.
Claims53
A dental impression material, comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst;
- a crosslinker compound containing at least two SiH groups;
- a catalyst capable of catalyzing a hydrosilation reaction;
- and
- one or more cure-indicating dyes, wherein, in a dye evaluation test, said dye exhibits a color change within about 10 minutes at 25.degree. C. when 500 .mu.g of said dye, 500 .mu.l of dichloromethane, 100 .mu.l of pentamethyldisiloxane and 10 .mu.l of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together,
- wherein said dye is represented by the formula ##STR31## wherein each of R.sup.48, R.sup.49, and R.sup.50, is independently selected from the group consisting of:
- hydrogen, halogen and an acyclic, alicyclic or aromatic hydrocarbyl group optionally interrupted with one or more heteroatoms,
- each of R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, and R.sup.56 is independently selected from the group consisting of hydrogen and an acyclic, alicyclic or aromatic hydrocarbyl group optionally interrupted with one or more heteroatoms, and optionally, any two of R.sup.51, R.sup.52, R.sup.53, R.sup.54, R.sup.55, and R.sup.56 may together form an alicyclic or aromatic ring.
5 more elements
A dental impression material, comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst;
- a crosslinker compound containing at least two SiH groups;
- a catalyst capable of catalyzing a hydrosilation reaction;
- and one or more cure-indicating dyes, wherein said dye exhibits a color change within about 10 minutes at 25.degree. C. when 500 .mu.g of said dye, 500 .mu.l of dichloromethane, 100 .mu.l of pentamethyldisiloxane and 10 .mu.l of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together,
- wherein said dye is represented by the formula ##STR32## wherein X.sup.4 is N--R.sup.67 R.sup.68, O--R.sup.69, S--R.sup.70 or CR.sup.71 R.sup.72 R.sup.73 and wherein each of R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, is independently selected from the group consisting of hydrogen, halogen, a hydrocarbyl group optionally interrupted with one or more heteroatoms and an acyclic, alicyclic or aromatic heterocyclic group, and each of R.sup.67, R.sup.68, R.sup.69, R.sup.70, R.sup.71, R.sup.72, and R.sup.73 is independently selected from the group consisting of hydrogen, a hydrocarbyl group optionally interrupted with one or more heteroatoms and an acyclic, alicyclic or aromatic heterocyclic group.
2 more elements
A dental impression material, comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst;
- a crosslinker compound containing at least two SiH groups;
- a catalyst capable of catalyzing a hydrosilation reaction;
- and
- one or more cure-indicating dyes, wherein said dye exhibits a color change within about 10 minutes at 25.degree. C. when 500 .mu.g of said dye, 500 .mu.l of dichloromethane, 100 .mu.l of pentamethyldisiloxane and 10 .mu.l of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together, wherein said dye is selected from compounds of the formula ##STR33##
2 more elements
A dental impression material, comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst;
- a crosslinker compound containing at least two SiH groups;
- a hydrosilation catalyst comprising a complex of platinum and an unsaturated organosilicon material;
- and
- one or more cure-indicating dyes, wherein, in a dye evaluation test, said dye exhibits a color change within about 10 minutes at 25.degree. C. when 500 .mu.g of said dye, 500 .mu.l of dichloromethane, 100 .mu.l of pentamethyldisiloxane and 10 .mu.l of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together and wherein said impression material exhibits a color change upon curing.
2 more elements
A dental impression material, comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst;
- a crosslinker compound containing at least two SiH groups;
- a hydrosilation catalyst comprising a complex of platinum and a complexing material in the form of an unsaturated organosilicon material selected from the group consisting of:
- unsaturated silanes having the empirical formula,
- R.sub.a R'.sub.b Si.sub.c X.sub.z
- where R is free of aliphatic unsaturation and selected from monovalent hydrocarbon radicals, R' is selected from monovalent aliphatically unsaturated hydrocarbon radicals, X is a hydrolyzable radical, c is an integer having a value of at least 1, b is an integer having a value greater than or equal to 2 and the sum of a, b and z equals the sum of 2 and two times c for a linear or branched silane and wherein c is an integer having a value from 4 to 18 and the sum of a, b and z equals two times c for a cyclic silane;
- unsaturated linear or branched siloxanes of the empirical formula,
- R.sub.d R'.sub.e Si.sub.f O.sub.(f-1)
- where R and R' are as defined above, f is an integer having a value of between 2 and 10,000, e is an integer having a value greater than or equal to 2 and the sum of d and e equals the sum of 2 and two times f;
- and
- unsaturated cyclic siloxanes of the empirical formula,
- R.sub.d R'.sub.e Si.sub.f O.sub.f
- where R and R' are as defined above, e is an integer having a value greater than or equal to 2, f is an integer having a value from 3 to 18, and the sum of d and e equals two times f, and wherein said catalyst complex is formed using a platinum halide selected from the group consisting of H.sub.2 PtCl.sub.6.nH.sub.2 O, NaHPtCl.sub.6.nH.sub.2 O, KHPtCl.sub.6.nH.sub.2 O, Na.sub.2 PtCl.sub.6.nH.sub.2 O, K.sub.2 PtCl.sub.6.nH.sub.2 O, PtCl.sub.4.nH.sub.2 O, PtCl.sub.2, Na.sub.2 PtCl.sub.4.nH.sub.2 O, H.sub.2 PtCl.sub.4.nH.sub.2 O, NaHPtCl.sub.4.nH.sub.2 O, KHPtCl.sub.4.nH.sub.2 O, K.sub.2 PtBr.sub.4, ((CH.sub.2 .dbd.CH.sub.2).PtCl.sub.2).sub.2, (PtCl.sub.2.C.sub.3 H.sub.6).sub.2, and the reaction product of chloroplatinic acid hexahydrate and octyl alcohol;
- and
- one or more cure-indicating dyes, wherein said impression material exhibits a color change upon curing, wherein said dye exhibits a color change within about 10 minutes at 25.degree. C. when 500 .mu.g of said dye, 500 .mu.l of dichloromethane, 100 .mu.l of pentamethyldisiloxane and 10 .mu.l of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together, and wherein said cure-indicating dye is present in an amount between 0.0003 and 0.03 weight percent.
12 more elements
A dental impression material, comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst;
- a crosslinker compound containing at least two SiH groups;
- a hydrosilation catalyst comprising a complex of platinum and a complexing material in the form of an unsaturated organosilicon material selected from the group consisting of:
- unsaturated silanes having the empirical formula,
- R.sub.a R'.sub.b Si.sub.c X.sub.z
- where R is free of aliphatic unsaturation and selected from monovalent hydrocarbon radicals, R' is selected from monovalent aliphatically unsaturated hydrocarbon radicals, X is a hydrolyzable radical, c is an integer having a value of at least 1, b is an integer having a value greater than or equal to 2 and the sum of a, b and z equals the sum of 2 and two times c for a linear or branched silane and wherein c is an integer having a value from 4 to 18 and the sum of a, b and z equals two times c for a cyclic silane;
- unsaturated linear or branched siloxanes of the empirical formula,
- R.sub.d R'.sub.e Si.sub.f O.sub.(f-1)
- where R and R' are as defined above, f is an integer having a value of between 2 and 10,000, e is an integer having a value greater than or equal to 2 and the sum of d and e equals the sum of 2 and two times f;
- and
- unsaturated cyclic siloxanes of the empirical formula,
- R.sub.d R'.sub.e Si.sub.f O.sub.f
- where R and R' are as defined above, e is an integer having a value greater than or equal to 2, f is an integer having a value from 3 to 18, and the sum of d and e equals two times f, and wherein said catalyst complex is formed using a platinum halide selected from the group consisting of H.sub.2 PtCl.sub.6.nH.sub.2 O, NaHPtCl.sub.6.nH.sub.2 O, KHPtCl.sub.6.nH.sub.2 O, Na.sub.2 PtCl.sub.6.nH.sub.2 O, K.sub.2 PtCl.sub.6.nH.sub.2 O, PtCl.sub.4.nH.sub.2 O, PtCl.sub.2, Na.sub.2 PtCl.sub.4.nH.sub.2 O, H.sub.2 PtCl.sub.4.nH.sub.2 O, NaHPtCl.sub.4.nH.sub.2 O, KHPtCl.sub.4.nH.sub.2 O, K.sub.2 PtBr.sub.4, ((CH.sub.2 .dbd.CH.sub.2).PtCl.sub.2).sub.2, (PtCl.sub.2.C.sub.3 H.sub.6).sub.2, and the reaction product of chloroplatinic acid hexahydrate and octyl alcohol, and wherein said catalyst is a Karstedt catalyst and has available inorganic halogen of less than about 0.1 gram atoms of halogen per gram atom of platinum;
- and
- one or more cure-indicating dyes having a molar extinction coefficient of at least 10,000 M.sup.-1 cm.sup.-1, wherein said impression material exhibits a color change upon curing of at least 10 .DELTA.E* units.
12 more elements
A dental impression material comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a catalyst;
- a crosslinker compound containing at least two SiH groups;
- a hydrosilation catalyst;
- and
- one or more cure-indicating dyes selected from the group consisting of neutral dyes represented by the following general formula:
- ##STR46## wherein:
- each R.sup.1, R.sup.2, R.sup.3, and R.sup.4 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group, and wherein R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 may be connected to form a saturated or unsaturated ring;
- A is O, S, or NR.sup.22, wherein
- R.sup.22 is hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group;
- and
- B is any group capable of providing extended conjugation thereby rendering the dye capable of absorbing visible, near-UV, or near-infrared radiation including groups of formula D, E, F, H, or J, wherein
- D is represented by formula:
- ##STR47## each R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group and wherein any two adjacent R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 groups may be connected to form a ring;
- E is represented by formula:
- ##STR48## wherein:
- X.sup.1 is C(R.sup.12).sub.2, S, NR.sup.12, or O;
- X.sup.2 is C(R.sup.12).sub.2, S, NR.sup.12, or O;
- and
- each R.sup.10, R.sup.11 and R.sup.12 group is independently hydrogen, a hydrocarbyl-containing group, or a heterocyclic group and wherein R.sup.10 and R.sup.11 may be connected to form a ring;
- F is represented by the formula:
- ##STR49## wherein:
- X.sup.3 is N or CR.sup.16 ;
- and
- each R.sup.13, R.sup.14, R.sup.15, and R.sup.16 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group and wherein any two adjacent R.sup.13, R.sup.14, R.sup.15, and R.sup.16 groups may be connected to form a ring;
- H is represented by formula:
- ##STR50## wherein:
- each R.sup.20 and R.sup.21 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group and wherein R.sup.15, and R.sup.16 may be connected to form a ring;
- and
- J is represented by formula:
- ##STR51## wherein:
- each R.sup.5, R.sup.6, R.sup.7 and R.sup.8 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group and wherein any two R.sup.5, R.sup.6, R.sup.7 and R.sup.8 groups may be connected to form a ring;
- and
- R.sup.23 is hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group;
- sulfonyl dyes represented by the following general formula:
- ##STR52## wherein:
- each R.sup.24 and R.sup.25 group is independently hydrogen, a hydrocarbyl-containing group, or a heterocyclic group with the proviso that at least one of R.sup.24 and R.sup.25 is or contains a substituted aryl, aminoaryl or heterocyclic group;
- each R.sup.26 and R.sup.27 group is independently a --(CF.sub.2).sub.m F group wherein m is a number between 0 and 20;
- and
- n is an integer less than 5;
- neutral dyes represented by the following general formula:
- ##STR53## wherein:
- each R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.29 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group, and wherein any two adjacent R.sup.1, R.sup.2, R.sup.3, R.sup.4, or R.sup.29 groups may be connected to form a ring;
- and
- R.sup.30 is hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group and n is an integer less than 5;
- anionic dyes having the following general formula:
- ##STR54## wherein:
- Z represents the non-metallic atoms necessary to complete a substituted or unsubstituted nitrogen-containing heterocyclic ring;
- each R.sup.28 is independently hydrogen, a hydrocarbyl-containing group, or a heterocyclic group;
- n is an integer less than 5;
- and wherein
- M+ is selected from any suitable cation;
- cationic dyes having the following general formula:
- ##STR55## wherein:
- each R.sup.31, R.sup.32, R.sup.33, and R.sup.34 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group, and wherein any two adjacent R.sup.31, R.sup.32, R.sup.33, or R.sup.34 groups may be connected to form a ring;
- R.sup.35 and R.sup.36 are as defined above for R.sup.33 and R.sup.34 ;
- X is O, S, or NR.sup.37 ;
- Y is N or CR.sup.38 ;
- R.sup.37 and R.sup.38 are as defined above for R.sup.33 ;
- and wherein
- M- is any suitable anion;
- cationic dyes having the following general formula:
- ##STR56## wherein:
- each R.sup.31, R.sup.32, R.sup.33, R.sup.34 and R.sup.40 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group, and wherein any two adjacent R.sup.31, R.sup.32, R.sup.33, or R.sup.34 groups may be connected to form a ring;
- R.sup.39 is independently hydrogen, a hydrocarbyl-containing group, or a heterocyclic group;
- X is C.dbd.R.sup.48, C(R.sup.38).sub.2, O, S, or NR.sup.37, wherein
- R.sup.37 is as defined above for R.sup.39,
- R.sup.38 is as defined above for R.sup.40,
- R.sup.48 is an oxo group, a divalent hydrocarbyl-containing group or a divalent heterocyclic group, and wherein R.sup.48 and R.sup.34 may be connected to form an unsaturated ring, and R.sup.37 and R.sup.34 may be connected to form a ring;
- and wherein
- M- is any suitable anion;
- and
- cationic dyes having the following general formula:
- cationic dyes having the following general formula:
- ##STR57## wherein:
- each R.sup.42 to R.sup.47 group is independently hydrogen, halogen, a hydrocarbyl-containing group, or a heterocyclic group;
- each R.sup.40, R.sup.41, R.sup.46, and R.sup.47 group is indepedently hydrogen, a hydrocarbyl-containing group, or a heterocyclic group and wherein any two adjacent R.sup.41 to R.sup.43 groups may be connected to form a ring and wherein R.sup.44 and R.sup.45 may be connected to form a ring;
- n is an integer less than 5;
- and wherein
- M- is any suitable anion, and wherein said dental impression material exhibits a color change upon curing of at least 10 .DELTA.E* units.
76 more elements
A method of monitoring the curing of a dental impression material, comprising the steps of:
- placing against the teeth of a patient an impression material comprising a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a hydrosilation catalyst, a crosslinker compound containing at least two SiH groups, a hydrosilation catalyst comprising a complex of platinum and an unsaturated organosilicon material, and one or more cure-indicating dyes;
- and
- visually observing said impression material, wherein said impression material has a first color before the cure reaction is effected and a second color after the cure reaction has been effected to an indication point, and wherein said first and second colors differ by at least 5 .DELTA.E* units.
A dental impression material comprising:
- a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a catalyst;
- a crosslinker compound containing at least two SiH groups;
- a hydrosilation catalyst;
- between 20 and 90 weight percent filler;
- a surfactant;
- and
- one or more cure-indicating dyes selected from the group consisting of indoaniline dyes, indophenol dyes, quinone monoimine dyes, quinone diimine dyes, cyanine dyes, merocyanine dyes, cyclohexadienone dyes, iminocyclohexadienone dyes, imidazolylidinecyclohexadienone dyes, dihydronaphthalenone dyes, iminodihydronaphthalenone dyes, imidazolylidinedihydronaphthalenone dyes, cyclohexadienimine dyes, aryl substituted bis (trifluoromethylsulfonyl)hexatrienyl dyes, aryl substituted bis (trifluoromethylsulfonyl)butadienyl dyes, aryl substituted bis (fluorosulfonyl)hexatrienyl dyes, aryl substituted bis (fluorosulfonyl)butadienyl dyes, oxazolone dyes, cationic dyes, anionic dyes and amphoteric dyes, wherein said impression material exhibits a color change upon curing of at least 10 .DELTA.E* units.
4 more elements
Dependencies are inferred from the claim text.