Wound dressing membrane

• US 4,846,165 A
• Filed: 12/19/1986
• Issued: 07/11/1989
• Est. Priority Date: 11/26/1986
• Status: Expired due to Fees

• Current Assignee: Dentsply Management Corporation
• Original Assignee: Dentsply Research & Development Corporation (Astrazeneca PLC)
• Inventors: Jefferies, Steven R., Hare, Pamela H.
• Primary Examiner(s): NOT, DEFINED
• Assistant Examiner(s): Rose, Sharon
• Application Number:
  US06/944,476
• Time in Patent Office: 935 Days
• Field of Search: 433/229, 433/215, 433/229, 433/80, 433/201.1, 433/9, 604/890, 604/48, 604/49, 604/54, 604/57, 604/77, 604/304, 604/310, 604/311, 128/82.1, 128/155, 128/156, 128/787, 424/425, 424/434, 424/435, 424/443, 424/486, 424/487, 514/964, 514/965, 523/111, 523/109, 523/118, 523/116, 525/920, 525/937, 522/908
• US Class Current: 228/156
• CPC Class Codes: A61K 6/40 Primers for dental adhesives A61K6/30
• CPC Class Codes: A61K 6/69 Medicaments
• CPC Class Codes: C08F 299/06 from polyurethanes
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/8116 esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: Y10S 522/908 Dental utility

Abstract

Disclosed is a method for producing an intra-oral dental bandage membrane and/or therapeutic membrane containing therapeutic agent. Actinic light is used to polymerize the membrane composition material to fix the composition in position locked with rigid dental structure such as teeth. The polymerizable substance is manipulated and shaped in a fluid state and then set, as shaped very rapidly in situ. Also disclosed is a new treatment membrane that in a preferred form is a non-symetrical oligomer that is a urethane polyacrylate.

Claims

1. A method of producing an elastomeric bandage in situ in the oral cavity of a mammal comprising:

applying a fluid actinic light polymerizable composition comprising polymerizable organic compound and visible actinic light initiator to tissue in the oral cavity in need of the protection of a bandage,

flowing said fluid polymerizable composition in direct contact with rigid dentition to provide a direct mechanical locking with said rigid dentition upon the setting of said fluid polymerizable composition, causing said fluid polymerizable composition to set by exposing said polymerizable composition to actinic light to form a elastomeric dental bandage mechanically locked to said rigid dentition.

2. The method of producing a dental bandage in the oral cavity of claim 1 wherein said polymerizable organic compound has a reaction functionality of two, said setting is at least in part in response to engagement of a surface of said fluid polymerizable composition by actinic light and said setting forms an elastomeric oral cavity dental bandage.

3. The method of producing a dental bandage in the oral cavity of claim 2 wherein said fluid actinic light polymerizable composition retains its fluid form for a period of at least two months as a one component composition when stored actinic light free, is applied from a syringe and is flowed to completely surround at least one tooth in direct contact with said tooth to provide said mechanical locking and is set completely surrounding said at least one tooth.

4. The method of producing a dental bandage in the oral cavity of claim 2 wherein said fluid actinic light polymerizable composition retains its fluid form for a period of at least two months as one component composition when stored actinic light free is applied from a syringe and is flowed to a wedged position in an embrasure between two teeth in direct contact with said teeth to provide said mechanical locking and is set in wedged position in said embrasure between said two teeth.

5. The method of producing a dental bandage in the oral cavity of claim 2 wherein said polymerizable organic compound is an oligomer that is a urethane acrylate and said actinic light initiator is activated by actinic light having a wave length of about 360-600 nm.

6. The method of producing a dental bandage in the oral cavity of claim 1 wherein said fluid actinic light polymerizable composition comprises therapeutic substance homogeneously mixed throughout, and after said setting said therapeutic substance is leachable in said oral cavity for a period of at least one week.

7. The method of producing a dental bandage in the oral cavity of claim 1, wherein said polymerizable organic compound comprises a compound of the general formula:

space="preserve" listing-type="equation">R.sub.1 --A]R.sub.2

R₁ is ##STR4## R₂ is ##STR5## wherein R₃ is H, F, CN or methyl

R₃ may be the same or different in each position

R₄ is a divalent hydrocarbon radical or benzene substituted divalent hydrocarbon radical having 2-100 carbon atoms and may be straight or branched chain or cyclic or a combination thereof, and is a polyurethane oligomer having a molecular weight of at least 600 said method comprising

(a) cleaning and drying said rigid dental structure;

(b) thereafter flowing said fluid polymerizable composition directly against said rigid dental structure,

(c) curing said fluid dental polymerizable composition while it is directly engaged with said rigid dental structure to mechanically lock it therewith.

8. The method of producing a dental bandage in the oral cavity of claim 7 wherein said organic compound comprises a composition of the general formula:

##STR6## R₇ =Alkylene, and x=10 to 100 wherein.

9. The method of producing a dental bandage of claim 8 wherein said fluid actinic light curable composition includes said polymerizable organic compound in an amount of about 5 to 95% by weight of the total weight of said fluid actinic light curable composition;

said actinic light initiator in an amount of about 0.001 to about 10% by weight of said polymerizable organic compound; and

filler in an amount of about 5 to 95% by weight of the total weight of said fluid actinic light curable composition.

10. The method of producing a dental bandage in the oral cavity of claim 1 wherein said fluid actinic light polymerizable composition comprises therapeutic agent.

11. A method for producing an interoral drug delivery device in situ in a mammal comprising:

positioning a fluid polymerizable composition comprising polymerizable organic compound, polymerization initiator and therapeutic agent inter-orally by delivering said composition from a syringe into direct contact with rigid dentition,

modeling said fluid polymerizable composition to conform to the shape and position of said right dentition while it is interoral, and

polymerizing said fluid polymerizable composition in situ by the application of visible actinic light to produce an elastomeric drug delivery device which is mechanically interlocked with said rigid dentition.

12. The method of claim 11, wherein said fluid polymerizable composition comprises solid leachable material chosen from the group consisting of microcapsules, prepolymerized polymer microparticles including therapeutic agent and mixtures thereof having a particle size of less than about 250 microns chosen from the group consisting of water soluble and water disperable prepolymerized polymers and mixtures thereof.

13. The method of claim 11, wherein said polymerizable organic compound comprising comprises a compound of the general formula:

space="preserve" listing-type="equation">R.sub.1 --A]R.sub.2

R₁ is ##STR7## R₂ is ##STR8## wherein R₃ is H, F, CN or methyl

R₃ may be the same or different in each position

R₄ is a divalent hydrocarbon radical or benzene substituted divalent hydrocarbon radical having 2-100 carbon atoms and may be straight or branched chain or cyclic or a combination thereof, and is a polyurethane oligomer having a molecular weight of at least 600;

wherein in said method said modeling includes forming said fluid polymerizable composition in sufficient juxtaposition to rigid dental structure to provide a mechanical locking with said rigid dental structure upon the polymerizing of said fluid polymerizable composition, and said polymerizing in situ bringing about a locking with said rigid dental structure,

and said method comprising cleaning and drying said rigid dental structure before positioning said fluid polymerizable composition.

14. A method of claim 13 wherein said fluid polymerizable includes said polymerizable organic compound in an amount of about 5 to 95% by weight of the total weight of said fluid actinic light curable composition;

said actinic light initiator in an amount of about 0.001 to about 10% by weight of said polymerizable organic compound; and

filler in an amount of about 5 to 95% by weight of the total weight of said fluid actinic light curable composition.

15. The method of claim 11 wherein said therapeutic substance is homogeneously mixed throughout said fluid polymerizable composition and after said setting is leachable in said oral cavity for a period of at least one week.

16. A method of producing a dental bandage in the oral cavity of a mammal comprising:

acid etching the enamel of at least one tooth in the oral cavity

applying a fluid visible actinic light polymerizable composition comprising a polymerizable organic compound and actinic light initiator to damaged tissue in the oral cavity,

flowing said fluid polymerizable composition in sufficient juxtaposition to said at least one acid etched tooth to provide attachment of said polymerizable composition on setting thereof,

setting said fluid polymerizable composition to attach to said at least one tooth and producing said oral cavity dental bandage.

17. The method of claim 16 in which said attachment of said polymerizable material to said at least one acid etched tooth is a mechanical locking thereof.

18. The method of claim 16 in which said attachment of said polymerizable material to said at least one acid etched tooth is an adhesive bonding thereto.