Patent US4383826A successfully refreshed from Google Patents.
US4383826A
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Adducts of diisocyanates and methacryloyl alkyl ethers, alkoxybenzenes or alkoxycycloalkanes, compositions containing such compounds, and method of use thereof
Assignee: Blendax GmbH
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Filing: 1981-06-23
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Granted: 1983-05-17
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Expires: 2001-06-23
Abstract
Abstract Polymerizable adducts of diisocyanates and methacryloyl alkyl ethers, alkoxybenzenes, or alkoxycycloalkanes are disclosed. The compounds of the present invention are formed into compositions which are useful as bone cement, fillings for cavities, and orthodontic adhesives. The compositions have improved mechanical properties, low water absorption, and excellent color and discoloration stability, coupled with a high filler content.
Inventors
- 👤 David V. Butler
- 👤 Patrick D. Kidd
- 👤 Jan A. Orlowski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 11:33
CPC Classifications
C; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; A; A61; A61K; A61K6/00; A61K6/20; A61K6/30; A61K6/80; A61K6/884; A61K6/887; A61K6/891; A61K6/896
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
60 words
A compound of the formula: ##STR2## wherein R 1 and R 2 are individually straight or branched chain, substituted or unsubstituted alkyl groups having 1 to 14 carbon atoms, a substituted or unsubstituted aryl group, or a substituted or unsubstituted cycloalkyl group, and R x is a divalent, aliphatic, cycloaliphatic, araliphatic, or aromatic radical having 2 to 14 carbon atoms.
Claim 2
Dependent Claim
60 words
A compound of the formula: ##STR2## wherein R 1 and R 2 are individually straight or branched chain, substituted or unsubstituted alkyl groups having 1 to 14 carbon atoms, a substituted or unsubstituted aryl group, or a substituted or unsubstituted cycloalkyl group, and R x is a divalent, aliphatic, cycloaliphatic, araliphatic, or aromatic radical having 2 to 14 carbon atoms.
Claim 3
Dependent Claim
39 words
A compound of claim 1 wherein R 1 and R 2 are taken from the class consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, lauryl, phenyl, benzyl, tolyl, xylyl, and cyclohexyl.
Claim 4
Dependent Claim
32 words
A compound of claim 1 wherein R x is taken from the class consisting of ethylene, propylene, butylene, pentamethylene, hexamethylene, octamethylene, 2-ethylhexamethylene, phenylene, phenoxyphenylene, tolylene, methylene bisphenyl, propylene-bisphenyl, cyclohexylene, methylene-biscyclohexyl, and propylenebiscyclohexyl.
Claim 5
Dependent Claim
13 words
A compound of claim 1 wherein R 1 and R 2 are 2-ethylhexyl.
Claim 6
Dependent Claim
24 words
A compound of claim 1 wherein R 1 and R 2 are alkyls having 2 to 8 carbon atoms, and R x is hexamethylene.
Claim 7
Dependent Claim
25 words
A compound of claim 1 wherein R 1 and R 2 are alkyls having 2 to 8 carbons, and R x is phenylene or tolylene.
Claim 8
Dependent Claim
25 words
A compound of claim 1 wherein R 1 and R 2 are alkyls having 2 to 8 carbons, and R x is cycloalkylene or methylenebiscycloalkyl.
Claim 9
Dependent Claim
13 words
A compound of claim 5 wherein R 1 and R 2 are 2-ethylhexyl.
Claim 10
Dependent Claim
21 words
A compound of claim 1 wherein R 1 and R 2 are substituted or unsubstituted phenyl, and R x is hexamethylene.
Claim 11
Dependent Claim
23 words
A compound of claim 1 wherein R 1 and R 2 are substituted or unsubstituted phenyl, and R x is phenylene or tolylene.
Claim 12
Dependent Claim
23 words
A compound of claim 1 wherein R 1 and R 2 are substituted or unsubstituted phenyl, and R x is cycloalkylene or methylenebiscycloalkyl.
Claim 13
Dependent Claim
21 words
A compound of claim 1 wherein R 1 and R 2 are substituted or unsubstituted cycloalkyl, and R x is hexamethylene.
Claim 14
Dependent Claim
13 words
A compound of claim 2 wherein R 1 and R 2 are cyclohexyl.
Claim 15
Dependent Claim
23 words
A compound of claim 1 wherein R 1 and R 2 are substituted or unsubstituted cycloalkyl, and R x is phenylene or tolylene.
Claim 16
Dependent Claim
13 words
A compound of claim 14 wherein R 1 and R 2 are cyclohexyl.
Claim 17
Dependent Claim
23 words
A compound of claim 1 wherein R 1 and R 2 are substituted or unsubstituted cycloalkyl, and R x is cycloalkylene or methylenebiscycloalkyl.
Claim 18
Dependent Claim
13 words
A compound of claim 16 wherein R 1 and R 2 are cyclohexyl.
Claim 19
Dependent Claim
11 words
A composition comprising a compound of claim 1 and a filler.
Claim 20
Dependent Claim
28 words
A composition of claim 18 containing a filler, 10 to 50% by weight of said compound and 0,1 to 5% by weight of a polymerization initiator or accelerator.
Claim 21
Dependent Claim
22 words
A composition of claim 18 wherein there are also present at least one UV absorber, dye, adhesion improver, or additional polymerizable substances.
Claim 22
Dependent Claim
26 words
A method of filling cavities in teeth comprising introducing a composition containing a compound of claim 1 into said cavities and causing said composition to set.
Claim 23
Dependent Claim
28 words
A method of producing prosthetic teeth comprising forming a composition containing a compound of claim 1 into the shape of a tooth, and causing said composition to set.
Claim 24
Dependent Claim
17 words
A method of claim 21 or 22 wherein said composition is set by application of UV radiation.
Claim 25
Dependent Claim
14 words
A compound of claim 1 wherein R x is alkylene, cycloalkylene, aralkylene, or aromatic.
Claim 26
Dependent Claim
19 words
A composition of claim 18 or 19 wherein said filler has a particle size of 0.01 to 100 microns.
Claim 27
Dependent Claim
13 words
A composition of claim 25 wherein said size is 0.05 to 50 microns.
Claim 28
Dependent Claim
15 words
A composition of claim 19 wherein said initiator is activated by UV or laser radiation.
Claim 29
Dependent Claim
16 words
A composition of claim 27 wherein said initiator is a dicarbonyl or a metal carbonyl compound.
Claim 30
Dependent Claim
19 words
A composition of claim 28 wherein said initiator is benzil or derivatives thereof, diacetyl, 2,3-pentadione, quinone, or quinone derivatives.
Claim 31
Dependent Claim
11 words
A composition of claim 29 wherein said benzil derivative is 4,4-oxybenzil.
Claim 32
Dependent Claim
19 words
A composition of claim 19 wherein said initiator is about 0.01 to about 5.0% by weight of said composition.
Claim 33
Dependent Claim
14 words
A composition of claim 19 wherein said accelerator is p-toluidine, dimethyl-p-toluidine, trialkylamines, or polyamines.
Claim 34
Dependent Claim
11 words
A composition of claim 32 wherein said polyamines are N,N,N',N'-tetraalkylalkylene diamines.
Claim 35
Dependent Claim
18 words
A composition of claim 19 wherein said accelerator is about 0.01 to 5.0% by weight of said composition.
Claim 36
Dependent Claim
39 words
A composition comprising a first mixture containing a polymerization initiator, a second mixture containing a polymerization accelerator, a compound of claim 1 in at least one of said mixtures, and a filler in at least one of said mixtures.
Claim 37
Dependent Claim
11 words
A composition of claim 35 wherein said initiator is a peroxide.
Claim 38
Dependent Claim
14 words
A composition of claim 35 wherein said initiator is aryl peroxide or silyl peroxide.
Claim 39
Dependent Claim
22 words
A composition of claim 36 wherein said peroxide is benzoyl peroxide, cumene hydroperoxide, urea peroxide, t-butyl hydroperoxide, t-butylperbenzoate, or a silyl peroxide.
Claim 40
Dependent Claim
17 words
A composition of claim 36 wherein said peroxide is 0.01 to 5.0% by weight of said composition.
Claim 41
Dependent Claim
17 words
A composition of claim 39 wherein said peroxide is 0.5 to 2.5% by weight of said composition.
Claim 42
Dependent Claim
22 words
A composition is claim 35 wherein at least one of said first mixture and said second mixture contains a polymerizable organo-silicon compound.
Claim 43
Dependent Claim
15 words
A composition of claim 41 wherein said organo-silicon compound are methacryloyl-alkyltrihydroxy silanes or methacryloyl-trimethoxy silane.
Claim 44
Dependent Claim
12 words
A composition of claim 26 wherein said size is about 30 microns.
References Cited (Backward Citations)
US3425988A
Cited
US3629187A
Cited
US3801344A
Cited
US3975203A
Cited
US3979426A
Cited
US4017649A
Cited
US4065627A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-05-16 | 1986-11-15 | 1987-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-05-16 | 1990-11-15 | 1991-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-05-16 | 1994-11-15 | 1995-05-17 | $7700.00 | Window Closed / Lapsed |