EP0269071A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Chain extended urethane diacrylate and dental impression formation
Assignee: Dentsply Sirona Inc
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Filing: 1987-11-24
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Granted: —
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Expires: 2007-11-24
Abstract
Abstract Disclosed is a new urethane polyacrylate having at least one terminal isocyanato acrylic pendent radical. Preferably the molecular chain within the acrylate caps has been extended with a polyhydroxy compound just before final end capping with isocyanato acrylic. The isocyanato acrylic is preferably isocyanato ethyl methacrylate and the urethane is diisocyanate capped polyether and the polyether radical is oxyalkylene. The method for producing the urethane polyacrylate involves end capping a polyol with diisocyanate yielding a reaction product with two reactive equivalents of isocyanate and then capping less than all of the isocyanate with a hydroxyacrylate, after which the remaining isocyanate is reacted with polyol to provide chain extension. The chain extending polyol is then capped with a isocyanato acrylic. Also disclosed is a new impression material for application to mammalian tissue and curing in contact therewith; the impression material including a free radical polymerizable resin, alkyl benzensulfonyl titanate, polymerization initiator, and filler; and a method of use.
Inventors
- 👤 Pamela H. Hare
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-10 01:00
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/81; C08G18/8108; C08G18/8116; A; A61; A61K; A61K6/00; A61K6/90; C08F; C08F299/00; C08F299/02; C08F299/06; C08G18/08; C08G18/10; C08G18/28; C08G18/67; C08G18/671; C08G18/672; H; H04; H04R; H04R25/00; H04R25/65; H04R25/658; Y; Y10; Y10S; Y10S522/00; Y10S522/908; Y10S525/00; Y10S525/92
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
90 words
A new composition of matter comprising a compound of the general formula wherein R₁ may be the same or different R₃ is H, alkyl of 2-10 carbons, sub alkyl of 2-10 carbons, aryl of 6-14 carbon, sub aryl of 6-14 carbons, F, CN and R₃ may be the same or different in each position; R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof from 2-10 carbons; and [A] is a polyurethane, polyether or polyester backbone.
Claim 2
Dependent Claim
90 words
A new composition of matter comprising a compound of the general formula wherein R₁ may be the same or different R₃ is H, alkyl of 2-10 carbons, sub alkyl of 2-10 carbons, aryl of 6-14 carbon, sub aryl of 6-14 carbons, F, CN and R₃ may be the same or different in each position; R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof from 2-10 carbons; and [A] is a polyurethane, polyether or polyester backbone.
Claim 3
Dependent Claim
57 words
The new composition of matter of Claim 1 wherein said compounds provides that general formula A is [R₅ X R₆] R₅ and R₆ are each divalent hydrocarbon radicals or divalent sub hydrocarbon radicals, X is a polyurethane and R₅-X and R₆-X are joined by a urethane linkage and R₅ and R₆ have from 2 to 100 carbons.
Claim 4
Dependent Claim
26 words
The composition of claim 1 in which [A] is where R and R₈ are alkyl of 2 to 25 carbons and x is 10 to 100.
Claim 5
Dependent Claim
38 words
A new composition of matter of claim 1 comprising a compound of the general formula where R₈ is alkyl of 2 to 8 carbons, R is alkyl of 2 to 25 carbons, and x = 10 to 100.
Claim 6
Dependent Claim
27 words
The new composition of matter of Claim 1 comprising an initiator activated by actinic light within the visible light range of about 360 to about 600 nanometers.
Claim 7
Dependent Claim
71 words
The new composition of matter of Claim 1 wherein said composition is a dental impression material, non-toxic in use in the oral cavity, stable in storage for at least one (1) month as a one-component composition when actinic light free, and assumes a permanent elastomeric memory when exposed to light filtered to limited wavelengths substantially within the visible light range for one (1) minute to a depth of one (1) inch.
Claim 8
Dependent Claim
97 words
A new impression material for application to mammalian tissue and curing in contact therewith to set the impression thereof; said impression material comprising free radical initiated polymerizable resin present in an amount of about 5 to 95% by weight of the total composition; alkyl benzensulfonyl titanate present in an amount of about 0.001 to about 2% by weight of the total composition; a polymerization initiator present in an amount of about 0.001 to about 10% by weight of polymerizable resin; and filler present in an amount of about 5 to 95% by weight of the total composition.
Claim 9
Dependent Claim
97 words
A new impression material for application to mammalian tissue and curing in contact therewith to set the impression thereof; said impression material comprising free radical initiated polymerizable resin present in an amount of about 5 to 95% by weight of the total composition; alkyl benzensulfonyl titanate present in an amount of about 0.001 to about 2% by weight of the total composition; a polymerization initiator present in an amount of about 0.001 to about 10% by weight of polymerizable resin; and filler present in an amount of about 5 to 95% by weight of the total composition.
Claim 10
Dependent Claim
97 words
The new impression material of Claim 7 wherein said free radical initiated polymerizable resin is present in an amount of about 10 to 80% by weight of the total composition; said alkyl benzensulfonyl titanate is titanium IV neoalkoxy, tris (dodecylbenzene) sulfonato and is present in an amount of about 0.005 to about 1% by weight of the total composition; said polymerization initiator is present in an amount of about 0.01 to about 5% by weight of polymerizable resin; and filler is present in an amount of about 20 to about 90% by weight of the total composition.
Claim 11
Dependent Claim
20 words
The new impression material of Claim 8 wherein said polymerization initiator is a photoinitiator and said filler comprising silicon dioxide.
Claim 12
Dependent Claim
126 words
The new impression material of Claim 9 wherein said free radical initiated polymerizable resin comprises a composition of the general formula wherein R₁ may be the same or different R₃ is H, alkyl of 2-10 carbons, sub alkyl of 2-10 carbons, aryl of 6-14 carbons, sub aryl of 6-14 carbons, F, CN, and R₃ may be the same or different in each position, R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof and has from 2-10 carbons and [A] is a polyurethane, polyether or polyester backbone in which, where R is alkyl of 2 to 25 carbons, R₈ is alkyl of 2 to 25 carbons, and x is 10 to 100.
Claim 13
Dependent Claim
44 words
The new impression material of Claim 10 wherein said free radical initiated polymerizable resin comprises a composition of the general formula where R₈ is alkyl of 2 to 8 carbons, R is alkyl of 2 to 25 carbons, and x = 10 to 100.
Claim 14
Independent Claim
122 words
A method for forming a dental impression of a portion of the oral cavity comprising (a) cleaning the surfaces to be taken by impression; (b) applying to said surfaces a dental impression material comprising a composition of the general formula wherein, R₃ is H, alkyl, sub alkyl, aryl, sub aryl, F, CN, and R₃ may be the same or different in each position, R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof; [A] is a polyurethane, polyether or polyester backbone; (c) curing said dental impression material while it is engaged with said surfaces to be taken; and (d) removing said cured dental impression material from said surfaces.
Claim 15
Independent Claim
122 words
A method for forming a dental impression of a portion of the oral cavity comprising (a) cleaning the surfaces to be taken by impression; (b) applying to said surfaces a dental impression material comprising a composition of the general formula wherein, R₃ is H, alkyl, sub alkyl, aryl, sub aryl, F, CN, and R₃ may be the same or different in each position, R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof; [A] is a polyurethane, polyether or polyester backbone; (c) curing said dental impression material while it is engaged with said surfaces to be taken; and (d) removing said cured dental impression material from said surfaces.
Claim 16
Dependent Claim
119 words
The method of Claim 12 wherein said free radical initiated polymerizable resin comprises a compound of the general formula where, R is alkyl of 2 to 25 carbons, and x = 10 to 100, and wherein said free radical initiated polymerizable resin is present in an amount of about 10 to 80% by weight of the total composition; said composition further comprising titanium IV neoalkoxy, tris (dodecylbenzene) sulfonato present in an amount of about 0.005 to about 1% by weight of the total composition; polymerization initiator present in an amount of about 0.01 to about 5% by weight of polymerizable resin; and filler present in an amount of about 20 to about 90% by weight of the total composition.
Claim 17
Dependent Claim
20 words
The new impression material of Claim 13 wherein said polymerization initiator is a photoinitiator and said filler comprises silicon dioxide.
Claim 18
Dependent Claim
91 words
A soft denture liner comprising a compound of the general formula wherein R₁ may be the same or different R₃ is H, alkyl of 2-10 carbons, sub alkyl of 2-10 carbons, aryl of 6-14 carbons, sub aryl of 6-14 carbons, F, CN and R₃ may be the same or different in each position, R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof and less from 2-10 carbons and [A] is a polyurethane, polyether or polyester backbone.
Claim 19
Dependent Claim
91 words
A soft denture liner comprising a compound of the general formula wherein R₁ may be the same or different R₃ is H, alkyl of 2-10 carbons, sub alkyl of 2-10 carbons, aryl of 6-14 carbons, sub aryl of 6-14 carbons, F, CN and R₃ may be the same or different in each position, R₄ is a divalent hydrocarbon radical or divalent sub hydrocarbon radical and may be straight or branched chain or cyclic or a combination thereof and less from 2-10 carbons and [A] is a polyurethane, polyether or polyester backbone.
Claim 20
Dependent Claim
34 words
The soft denture liner of claim 15 in which [A] is where R is alkyl of 2 to 25 carbons, R₈ is alkyl of 2 to 25 carbons, and x is 10 to 100.
Claim 21
Dependent Claim
69 words
The soft denture liner of claim 16 in which the new composition of matter of Claim 1 wherein said compounds provides that general formula A is [R₅ X R₆] R₅ and R₆ are each divalent hydrocarbon radicals or divalent sub hydrocarbon radicals, X is a polyurethane, polyether, or polyester and R₅-X and R₆-X are joined by a urethane linkage and R₅ and R₆ have from 2 to 100 carbons.
Claim 22
Dependent Claim
37 words
The soft denture liner of Claim 17 comprising a compound of the general formula where, R₈ is alkyl of 2 to 8 carbons, R is alkyl of 2 to 25 carbons, and x = 10 to 100.
Claim 23
Independent Claim
189 words
A method for making a compound having the formula: HMA-(OCN--NCO)-[O-PE-O]-(NCO-NCO)-BD-[OCN--OCN-HMA] wherein O-PE-O represents hydroxy substituted polyether, polyurethane or polyester, OCN and NCO represent isocyanate groups, and -(OCN-NCO)- represents polyisocyanate, HMA represents an unsaturated hydroxy substituted organic acid ester BD represents lower-alkyl-diol, comprising sequentially the steps of (a) reacting about 1 equivalent of hydroxy substituted oligomer with about 2 equivalents of diisocyanate to form a polyurethane chain having 2 isocyanate end groups (b) reacting the polyurethane formed in step (a) with about 1/2 equivalent of an unsaturated hydroxy substituted organic acid ester to predominantly form a polyurethane having an isocyanate group on one end and an unsaturated organic acid ester at another end thereof (c) reacting the product of step (b) with a lower alkyl diol to react with said isocyanate group to form a polyurethane having an unsaturated organic acid ester at one end and a hydroxy at another end thereof (d) reacting the reaction product of an unsaturated organic acid ester and a diisocyanate with the polyurethane formed in step (c) to form a polyurethane having an unsaturated hydroxysubstituted organic acid ester on at least 2 ends thereof.
Claim 24
Independent Claim
189 words
A method for making a compound having the formula: HMA-(OCN--NCO)-[O-PE-O]-(NCO-NCO)-BD-[OCN--OCN-HMA] wherein O-PE-O represents hydroxy substituted polyether, polyurethane or polyester, OCN and NCO represent isocyanate groups, and -(OCN-NCO)- represents polyisocyanate, HMA represents an unsaturated hydroxy substituted organic acid ester BD represents lower-alkyl-diol, comprising sequentially the steps of (a) reacting about 1 equivalent of hydroxy substituted oligomer with about 2 equivalents of diisocyanate to form a polyurethane chain having 2 isocyanate end groups (b) reacting the polyurethane formed in step (a) with about 1/2 equivalent of an unsaturated hydroxy substituted organic acid ester to predominantly form a polyurethane having an isocyanate group on one end and an unsaturated organic acid ester at another end thereof (c) reacting the product of step (b) with a lower alkyl diol to react with said isocyanate group to form a polyurethane having an unsaturated organic acid ester at one end and a hydroxy at another end thereof (d) reacting the reaction product of an unsaturated organic acid ester and a diisocyanate with the polyurethane formed in step (c) to form a polyurethane having an unsaturated hydroxysubstituted organic acid ester on at least 2 ends thereof.
Claim 25
Dependent Claim
22 words
The method of claim 19 in which PE is polyether, polyisocyanate is trimethyl hexamethylene diisocyanate, HMA is hydroxyethylmethacrylate, and BD is butanediol.
References Cited (Backward Citations)
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