Provisional crown-and-bridge resin containing tetrahydrofuryl methacrylate

{
  "publication_number": "US4264489A",
  "country": "US",
  "kind": "A",
  "title": "Provisional crown-and-bridge resin containing tetrahydrofuryl methacrylate",
  "abstract": "A provisional crown-and-bridge resin comprising a liquid resin component and a powder component. The liquid resin component contains tetrahydrofurfuryl methacrylate as a major ingredient and is free from methyl methacrylate. It also contains an anti-oxidant and an accelerator. The powder component contains poly (ethyl methacrylate) as a major ingredient and a curing agent for the resin component. The powder is mixed with the resin shortly before application at a ratio of about two to about five parts of powder to one part of liquid resin by weight, to give a suitably flowing mixture. The resin component may also contain ethyl methacrylate as a major ingredient and may contain ethoxylated bisphenol A dimethacrylate as a major ingredient. The powder may include a substantial proportion of amorphous silica and preferably incorporates a substantial amount of X-ray opaque barium glass.",
  "claims": [
    "1. A provisional crown-and-bridge resin comprising: a liquid resin component and a powder component, said liquid resin component containing tetrahydrofurfuryl methacrylate as a major ingredient and being free from methyl methacrylate and also containing an anti-oxidant and an accelerator, said powder component containing poly (ethyl methacrylate) as a major ingredient and a curing agent for the resin component, said powder being mixed with said resin shortly before application at a ratio of about two to about five parts of powder to one part of liquid resin by weight, to give a suitably flowing mixture.",
    "2. The provisional crown-and-bridge resin of claim 1, wherein said resin component also contains ethyl methacrylate as a major ingredient.",
    "3. The provisional crown-and-bridge resin of claim 2 wherein said resin component also contains ethoxylated bisphenol A dimethacrylate as a major component.",
    "4. The provisional crown-and-bridge resin of claim 1 wherein said powder includes a substantial proportion of amorphous silica.",
    "5. The provisional crown-and-bridge resin of claim 1 wherein said powder incorporates a substantial amount of X-ray opaque barium glass.",
    "6. A provisional crown-and-bridge resin comprising: a liquid resin component, containing as its major ingredients ethyl methacrylate and tetrahydrofurfuryl methacrylate and, as minor ingredients, an anti-oxidant and a cure accelerator, and, a powder component, containing as its major ingredients poly (ethyl methacrylate) and X-ray opaque filler and, as a minor ingredient, a curing agent for said liquid resin component, said resin and powder components being mixed to a desired consistency with the powder present in amounts by weight from about two to about five times the amount by weight of the resin.",
    "7. The resin of claim 6 having, as a minor ingredient of the liquid resin component, an ultra-violet-light absorbing material.",
    "8. A provisional crown-and-bridge resin comprising an intimate mixture of: a liquid resin component containing as its major ingredient a blend of ethyl methacrylate, tetrahydrofurfuryl methacrylate, and ethoxylated bisphenol A dimethacrylate, and, as minor ingredients an anti-oxidant and a cure accelerator, and a powder component having as its principal ingredient poly (ethyl methacrylate) and, as a minor ingredient, a curing agent for the liquid resin component, the powder component being present in an amount of about two to about five times as much, by weight, as the liquid resin component.",
    "9. The provisional crown-and-bridge resin of claim 8 wherein the powder component also includes a substantial amount of barium glass.",
    "10. The provisional crown-and-bridge resin of claim 8 wherein the powder compound also includes a substantial amount of amorphous silica.",
    "11. The provisional crown-and-bridge resin of claim 8 wherein said liquid resin compound also includes an ultra-violet-light absorbing agent.",
    "12. A provisional crown-and-bridge resin consisting essentially of a liquid resin component and a powder component mixed to a desired consistency, said liquid resin consisting essentially of: ______________________________________ Ingredient Parts by weight ______________________________________ Ethyl methacrylate 0-70.0 Ethoxylated bisphenol A dimethacrylate 40.0 Tetrahydrofurfuryl methacrylate 60.0 Anti-oxidant sufficient to prevent oxida- tion Cure accelerator as desired ______________________________________ said powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) 39-100 Amorphous silica 0-39 Curing agent enough to cure the curable resin in liquid resin component ______________________________________",
    "13. The provisional crown-and-bridge resin of claim 12 wherein said anti-oxidant is chosen for the group consisting of: ______________________________________ Ingredient Parts by Weight ______________________________________ Butylated hydroxytoluene 0.01 to 1.0 Hydroquinone 0.1 to 2.5 Methyl ether of hydroquinone 0.1 to 5.0 ______________________________________",
    "14. The provisional crown-and-bridge resin of claim 12 wherein the cure accelerator is chosen for the group consisting of: ______________________________________ Ingredient Parts by Weight ______________________________________ 2-hydroxyethyl-p-toluidine 0.3 to 1.94 N,N-3,5-tetramethylaniline 0.15 to.97 N,N-dimethyl-p-toluidine 0.07 to.97 ______________________________________",
    "15. The provisional crown-and-bridge resin of claim 12 wherein the curing agent is benzoyl peroxide at quantities from about 0.17% to about 5%, the amount increasing with decrease in the amount of tertiary amine in the liquid resin.",
    "16. The provisional crown-and-bridge resin of claim 12 containing an effective amount of ultra-violet-light absorbing agent.",
    "17. The provisional crown-and-bridge resin of claim 16 wherein said absorbing agent is 2-hydroxy-4-methoxybenzophenone, up to 2.0 parts by weight.",
    "18. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 60 Ethoxylated bisphenol A dimethacrylate 40 Butylated hydroxytoluene 0.1 2-hydroxy-4-methoxybenzophenone 2.0 2-hydroxyethyl-p-toluidine 2.0 ______________________________________ and a powder component consisting essentially of poly (ethyl methacrylate) with 1.5% benzoyl peroxide, the powder-to-resin ratio being about 3.5:1.0.",
    "19. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 60 Ethoxylated bisphenol A dimethacrylate 40 Butylated hydroxytoluene 0.1 2-hydroxy-p-toluidine 1.0 2-hydroxy-4-methoxybenzophenone 2.0 ______________________________________ and a powder component consisting essentially of poly (ethyl methacrylate) with 1.5% benzoyl peroxide, the powder-to-resin ratio being about 3.5:1.0.",
    "20. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 60 Ethyl methacrylate 40 Butylated hydroxytoluene 0.1 2-hydroxy-4-methoxybenzophenone 2.0 2-hydroxyethyl-p-toluidine 1.0 and a powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) with 1.5% benzoyl peroxide 50 a 90 to 10 mixture of poly (ethyl methacrylate) and poly (methyl methacrylate) without added benzoyl peroxide 50, the powder-to-resin ratio being about 3.5:1.0. ______________________________________",
    "21. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 40 Ethyl methacrylate 60 2-hydroxyethyl-p-toluidine 0.5 and a powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) with 1.5% benzoyl peroxide 50 a 90 to 10 mixture of poly (ethyl methacrylate) and poly (methyl methacrylate) without added benzoyl peroxide 50, ______________________________________ the powder-to-resin ratio being about 3.5:1.0.",
    "22. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 50 Ethyl methacrylate 50 2-hydroxyethyl-p-toluidine 0.3 2-hydroxy-4-methoxybenzophenone 2.0 ______________________________________ and a powder component consisting essentially of poly (ethyl methacrylate) with 1.5% added benzoyl peroxide, the powder-to-resin ratio being about 3.5:1.0.",
    "23. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 30 Ethyl methacrylate 70 2-hydroxyethyl-p-toluidine 1.0 2-hydroxy-4-methoxybenzophenone 2.0 Butylated hydroxytoluene 0.1 ______________________________________ and a powder component consisting essentially of poly (ethyl methacrylate) with 1.5% added benzoyl peroxide, the powder-to-resin ratio being about 3.5:1.0.",
    "24. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 56 Ethyl methacrylate 85 N,N-3,5-tetramethyl aniline 1.0 Butylated hydroxytoluene 0.14 ______________________________________ and a powder component consisting essentially of poly (ethyl methacrylate) with 1.5% added benzoyl peroxide, the powder-to-resin ratio being about 3.5:1.0.",
    "25. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Tetrahydrofurfuryl methacrylate 56 Ethyl methacrylate 85 N,N-3,5-tetramethyl aniline 2.0 Butylated hydroxytoluene 0.14 ______________________________________ and a powder component consisting essentially of poly (ethyl methacrylate) with 1.5% added benzoyl peroxide, the powder-to-resin ratios from about 2:1 to about 5:1.",
    "26. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Ethyl methacrylate 40 Tetrahydrofurfuryl methacrylate 60 2-hydroxy-4-methoxybenzophenone 2.0 and a powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) with 1.5% benzoyl peroxide 70 Barium glass coated with silane 30, ______________________________________ the powder-to-resin ratio being about 4:1.",
    "27. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Ethyl methacrylate 34.83 Tetrahydrofurfuryl methacrylate 52.25 Ethoxylated bisphenol A dimethacrylate 9.68 Butylated hydroxytoluene 0.10 2-hydroxyethyl-p-toluidine 1.12 2-hydroxy-4-methoxybenzopherine 1.94 ______________________________________ and a powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) with added benzoyl peroxide 70.0 Barium glass coated with silane 30.0 the powder-to-resin ratio being about 3.5:1.0. ______________________________________",
    "28. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Part I Ethyl methacrylate 40 Tetrahydrofurfuryl methacrylate 60 2-hydroxy-4-methoxybenzophenone 2.0 Butylated hydroxytoluene 0.1 2-hydroxyethyl-p-toluidine 1.0 Part II Ethoxylated bisphenol A dimethacrylate 100.0 2-hydroxy-4-methoxybenzophenone 2.0 Butylated hydroxytoluene 0.1 2-hydroxyethyl-p-toluidine 2.0 ______________________________________ the ratio of Part I and Part II lying in the range of 1:9 to 9:1, and a powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) with 1.5% benzoyl peroxide 70 Barium glass coated with silane 30 ______________________________________ the powder-to-resin ratio being about 3.5:1.0.",
    "29. A provisional crown-and-bridge resin, consisting essentially of a liquid resin component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Ethyl methacrylate 36 Tetrahydrofurfuryl methacrylate 54 Ethoxylated bisphenol A dimethacrylate 10 Butylated hydroxytoluene 0.10 2-hydroxyethyl-p-toluidine 1.25 2-hydroxy-4-methoxybenzophenone 2.0 ______________________________________ and a powder component consisting essentially of: ______________________________________ Ingredient Parts by Weight ______________________________________ Poly (ethyl methacrylate) with 1.5% benzoyl peroxide 70 Barium glass 30 Silane 0.45 ______________________________________ the powder-to-resin ratio being about 3.5:1.0."
  ],
  "description_excerpt": "This invention relates to a provisional crown-and-bridge resin comprising a powder-liquid restorative system.\n\nProvisional crown-and-bridge resins are used in the mouth after a dentist has prepared the tooth, as a short-term filling-like structure for the patient to use during the time the laboratory is manufacturing the permanent crown or other prosthesis. Typically these resins are supposed to remain in place for several weeks, but may, in some cases, remain for as long as two years or more.\n\nFor some time the materials that have been used for temporary crown-to-bridge resins have been based on systems employing methyl methacrylate, for example, systems bases on methyl methacrylate resin and poly (methyl methacrylate) powder in conjunction with a peroxide and amine curing system. These systems have had high cure shrinkages, so that they have tended to pull away from the tooth as they cure.\n\nA more serious difficulty has been that these prior art systems have tended to cause tissue irritation, apparently due to traces of the methyl methacrylate monomer remaining in the cured polymer. These traces may be due to the difficulty of getting an exactly stoichiometric amount of curing agent mixed with the resin or to less-than-perfect mixture of ingredients.\n\nA recent system from Germany described as epimine has very low cure shrinkage, but it also has exhibited gingival irritation, apparently due to some toxic curing agent. This German material has also been somewhat weaker in impact strength than the materials previously used and is very translucent.",
  "cpc": [
    "C08F 265/06",
    "A61K 6/887",
    "Y10S 528/92"
  ],
  "ipc": [
    "A61C 5/08",
    "A61K 6/083",
    "A61K 6/884",
    "C08F 2/44",
    "C08F 20/00",
    "C08F 20/10",
    "C08F 20/22",
    "C08F 20/26",
    "C08F 220/10",
    "C08F 220/18",
    "C08F 220/28",
    "C08F 220/30",
    "C08F 265/06",
    "C08L 33/10"
  ],
  "assignees": [
    "Den Mat Inc"
  ],
  "inventors": [
    "Robert L. Ibsen",
    "William R. Glace"
  ],
  "filing_date": "1980-01-14",
  "publication_date": "1981-04-28",
  "grant_date": "1981-04-28",
  "priority_date": "1980-01-14",
  "application_number": "US-11167780-A",
  "family_id": "22339858",
  "cited_by_count": 41,
  "citations": [
    "US3265768A",
    "US3468977A",
    "US4001939A"
  ]
}