IP Library Granted Patent US 9,018,254
Granted Patent B2
US 9,018,254 · App. 14/087,693 · Granted Apr 28, 2015

Cyanoacrylate tissue adhesives with desirable permeability and tensile strength

Inventors: Sheng Zhang (Hickory, NC); Rafael Ruiz, Sr. (Hudson, NC); Max Azevedo (Alpharetta, GA)
Assignee: Adhezion Biomedical, LLC
A61K31/785A61L15/24
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Quick Facts
Patent No.
US 9,018,254
App. No.
14/087,693
Granted
Apr 28, 2015
Kind
B2
Abstract

A sterilized cyanoacrylate adhesive composition including a cyanoacrylate composition and a cure speed enhancer, wherein said sterilized cyanoacrylate adhesive composition does not cure upon sterilization, and wherein the composition when cured to form a film on a patient's tissue has water vapor transmission rate from about 950 to about 3000 g/m 2 /day.

Claims (24)

1. A sterilized cyanoacrylate adhesive composition comprising

99% or more by weight, based on the weight of the adhesive composition, of 2-octyl cyanoacrylate, mixed together with

a free radical stabilizer,

an anionic vapor phase stabilizer, and

100 to 1000 parts per million, based on the weight of the adhesive composition, of a 18-crown-6 crown ether,

wherein said composition is sterilized by irradiation, and wherein the sterilized composition has a viscosity of 5 to 70 cp following storage for twelve days at 80° C.; and

wherein the composition when cured on a patient's tissue has a water vapor transmission rate from about 950 to about 3000 g/m 2 /day.

2. The sterilized cyanoacrylate adhesive composition of claim 1 , wherein the sterilized composition has a viscosity of 5 to 30 cp following storage for twelve days at 80° C.

3. The sterilized cyanoacrylate adhesive composition of claim 1 , wherein said free radical stabilizer is butylated hydroxyl anisole and said anionic vapor phase stabilizer is sulfur dioxide.

4. The sterilized cyanoacrylate adhesive composition of claim 1 , wherein the composition has been treated with a particulate agent selected from the group consisting of vinyl pyrrolidone polymers and co-polymers.

5. The sterilized cyanoacrylate adhesive composition of claim 1 wherein the water vapor transmission rate is from about 1000 to about 2500 g/m 2 /day.

6. The sterilized cyanoacrylate adhesive composition of claim 5 wherein the water vapor transmission rate is from about 1500 to about 2200 g/m 2 /day.

7. The sterilized cyanoacrylate adhesive composition of claim 1 wherein the cured composition on the patient's tissue has a T-peel loading value of from about 34 to about 48 lbs.

8. The sterilized cyanoacrylate adhesive composition of claim 1 wherein the cured composition on the patient's tissue has a lap-shear tensile strength of from about 12 to about 18 lbs/in 2 .

9. The sterilized cyanoacrylate adhesive composition of claim 1 wherein the cured composition on the patient's tissue has a tension loading strength of from about 12 to about 16 lbs/in 2 .

10. The sterilized cyanoacrylate adhesive composition of claim 1 wherein the cured composition on the patient's tissue has a wound closure strength of from about 2 to about 4 lbs.

11. A method of sealing tissue comprising

applying the sterilized cyanoacrylate adhesive composition of claim 1 to a patient's tissue to be sealed; and

allowing the sterilized cyanoacrylate adhesive composition to cure.

12. The method of claim 11 wherein the free radical stabilizer is butylated hydroxyl anisole and the anionic vapor phase stabilizer is sulfur dioxide.

13. The sterilized cyanoacrylate adhesive composition of claim 1 , wherein the anionic vapor phase stabilizer is present in the composition at a concentration of less than 50 parts per million.

14. The sterilized cyanoacrylate adhesive composition of claim 13 , wherein the anionic vapor phase stabilizer is sulfur dioxide.

15. The sterilized cyanoacrylate adhesive composition of claim 3 , wherein the butylated hydroxyl anisole is present in the composition at a concentration of about 200 to about 15000 ppm.

16. A kit, comprising the sterilized cyanoacrylate adhesive composition of claim 1 and an applicator.

Assignments (1)
CHANGE OF NAME Recorded Jul 23, 2024
From: ADHEZION BIOMEDICAL, LLC
To: H.B. FULLER MEDICAL ADHESIVE TECHNOLOGIES, LLC.
Reel/Frame 068506/0455 →
Continuity (4)
Continuation 13000799
Continuation In Part 11767565 · Jun 25, 2007
Provisional Application 61132844 · Jun 23, 2008
Related Publication 20140186289A1 · Jul 3, 2014