Surgical adhesive

• US 4,740,534 A
• Filed: 08/21/1986
• Issued: 04/26/1988
• Est. Priority Date: 08/30/1985
• Status: Expired due to Fees

• Current Assignee: Sanyo Chemical Industries Limited 11-1 Ichinohashi Nomoto-Cho Higashiyama-Ku Kyoto Japan
• Original Assignee: Sanyo Chemical Industries Limited
• Inventors: Iwata, Hiroo, Matsuda, Takehisa, Itoh, Tetsuo
• Primary Examiner(s): Welsh, Maurice J.
• Application Number:
  US06/898,710
• Time in Patent Office: 614 Days
• Field of Search: 523/111, 523/118, 524/710, 524/783, 524/785, 524/791, 525/127, 528/76, 528/77, 528/78, 528/79, 528/904
• US Class Current: 523/111
• CPC Class Codes: A61L 24/046 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043 takes precedence
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• 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 18/302 Water
• CPC Class Codes: C08L 75/08 from polyethers
• CPC Class Codes: C09J 175/08 from polyethers
• CPC Class Codes: Y10S 528/904 Isocyanate polymer having stated hydrophilic or hydrophobic property

Abstract

Elastomeric or flexible surgical adhesives, comprising [A] NCO-terminated hydrophilic urethane prepolymer derived from hydrophilic polyether polyol of higher oxyethylene content, or combination of [A] with [B] unsaturated cyano compound containing cyano group attached to a carbon atom constituting the polymerizable double bond, are used for bonding of tissues, with rapid cure rate and sufficient bonding power.

Claims

1. A surgical adhesive, which comprises:

(A) at least one NCO-terminated hydrophilic urethane prepolymer, derived from at least one organic polyisocyanate and a polyol component comprising at least one hydrophilic polyether polyol having an oxyethylene content of at least 30%; and

(B) at least one unsaturated cyano compound containing a cyano group attached to a carbon atom constituting the polymerizable double bond.

2. The adhesive of claim 1, wherein said prepolymer has an isocyanate-content of 1-10% by weight.

3. The adhesive of claim 1, wherein said polyol component has an oxyethylene content of at least 30%.

4. The adhesive of claim 1, wherein said polyol component has an equivalent weight (average) of 100-5,000 and a functionality (average) of 2-8.

5. The adhesive of claim 1, wherein said polyisocyanate is at least one selected from the group consisting of aromatic polyisocyanates containing 6-20 carbon atoms, aliphatic polyisocyanates containing 2-18 carbon atoms, alicyclic polyisocyanates containing 4-15 carbon atoms, araliphatic polyisocyanates containing 8-15 carbon atoms, except carbon atoms in NCO groups, and modified polyisocyanates of these polyisocyanates containing one or more of urethane, carbodiimide, allophanate, urea, biuret, urethdione, urethimine, isocyanurate and oxazolidone groups.

6. The adhesive of claim 1, wherein said polyisocyanate is p-phenylene diisocyanate, or a combination thereof with one or more other polyisocyanates.

7. The adhesive of claim 1, wherein said hydrophilic polyether polyol is at least one adduct of ethylene oxide or a combination thereof with one or more other alkylene oxides to at least one compound containing two or more active hydrogen atoms.

8. The adhesive of claim 7, wherein said compound containing two or more active hydrogen atoms is at least one selected from the group consisting of polyhydric alcohols, polyhydric phenols, amines, polycarboxylic acids and phosphorous acids.

9. The adhesive of claim 1, wherein said hydrophilic polyether polyol is at least one selected from the group consisting of polyoxyethylene polyols, polyoxyethylene/oxypropylene polyols and polyoxyethylene/oxybutylene polyols.

10. The adhesive of claim 1, wherein said said polyol component comprises said hydrophilic polyether polyol and at least one other polyol selected from the group consisting of low molecular weight polyols, hydrophobic polyether polyols and polyester polyols.

11. The adhesive of claim 1, wherein said prepolymer is obtained by reacting said polyisocyanate with said polyol component in such an amount providing NCO/OH ratio of 1.5-5.0.

12. The adhesive of claim 1, which comprises 20-90% by weight of said prepolymer and 10-80% by weight of said cyano compound.

13. The adhesive of claim 1, wherein said cyano compound is at least one compound selected from the group consisting of cyanoacrylic acid, cyanomethacrylic acid, cyanoacrylates, cyanomethacrylates, acrylonitrile, methacrylonitrile, cyanoacrylonitrile and cyanomethacrylonitrile.

14. The adhesive of claim 1, wherein said cyano compound is at least one cyanoacrylic ester selected from the group consisting of methyl cyanoacrylate, ethyl cyanoacrylate nd iso-butyl cyanoacrylate.

15. The adhesive of claim 1, which contains up to 20% by weight of at least one additive selected from the group consisting of carbon black, metal oxides, silicates, acrylic resin powders, ceramic powders, softening agents, and stabilizers.