Adhesive sealant composition

a technology of adhesive sealant and composition, which is applied in the field of adhesive sealant composition, can solve the problems of limited adhesive composition, inability to use suitable tissue adhesive or sealant, and inability to meet the needs of paper after-treatment, powder delivery,

Inactive Publication Date: 2005-10-11
NEOMEND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0042]Two component adhesives were prepared according to the process described in Example 6 except that the pH of the buffer in the protein solution was changed as listed in Table 2. The data indicate that a preferred pH range is about 8.44-10.0.
[0043]TABLE 2CrosslinkingagentCureProteinPEG-SS2TimeConsistencyHSA130 mg/ml10minInitially softerBaxter3400 mwadhesive, hardnessLot 2837A238AAwith aging40% 0.1 M pH 7.4Carb/BicarbHSA130 mg/ml20secVery elastic, goodSigma3400 mwadhesive strength,Lot 63H9041not sticky40% 0.1 M pH 8.44Carb/BicarbHSA130 mg/ml10secHard gel, no stickySigma3400 mwLot 63H904140% 0.15 M pH 9.07Carb/BicarbHSA130 mg/ml5secHard gel, no stickySigma3400 mwLot 63H904140% 0.2 M pH 9.52Carb/BicarbHSA260 mg/ml5secHard gel, no stickySigma3400 mwLot 63H904140% 0.2 M pH 9.52Carb/BicarbHSA130 mg/ml7secElastic to hard gel,Sigma10,000 mwslightly stickyLot 63H904140% 0.2 M pH 9.52Carb/BicarbHSA260 mg/ml7secElastic to hard gel,Sigma10,000 mwslightly stickyLot 63H904140% 0.2 M pH 9.52Carb/BicarbHSA130 mg/ml25secVery elastic, notBaxter3400 mwstickyLot 2837A238AA40% 0.1 M pH 10Carb/BicarbHSA130 mg/ml25secVery elastic, notSigma3400 mwstickyLot 63H904140% 0.1 M pH 10Carb/Bicarbmw = weight average molecular weight
[0044]A 30% HSA (Human Serum Albumin) solution from Sigma Chemical Co. and a 25% HSA solution from Baxter Healthcare, Inc. were dialyzed against 0.1M carbonate/bicarbonate pH 10 buffer at 4° C. overnight and concentrated to about 40% by ultra-filtration through a 50,000 molecular weight cut-off cellulose ester disc membrane (Spectrum Medical Industries, Inc.) in a pressure filtration cell under nitrogen at 60 psig. The final concentration was calculated based on the volume of collected filtrate. The maximum concentration obtained under these conditions during overnight ultra-filtration was typically 42-45%. The RSA (Rabbit Serum Albumin) from Sigma and RSA crystallized protein from ICN Biomedical, Inc. were dissolved in 0.1M pH 10 carbonate/bicarbonate buffer and concentrated to 40% by the same method used for HSA.
[0045]Various concentrations of PEG-SS2 (3,400 mw and 10,000 mw) were prepared in deionized water. The albumins and crosslinking agent solutions were delivered in equal volume using a 1 ml dual syringe. The syringe tips were fitted with a Y connector which connected to a specially machined TEFLQN adaptor inserted into a 1.8 in.×0.187 in. (4.57 cm×0.475 cm) dia. spiral mixer nozzle (TAH Industries, Inc., Robbinsville, N.J., part no. 150-312). The adhesive mixture was injected through the mixer directly onto the test substrate for adhesion testing.
[0046]F...

Problems solved by technology

In sum, there are few available adhesive compositions that have sufficient strength, biocompatibility and bioabsorbability as well as other desired properties that would allow such compositions to be re...

Method used

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Examples

Experimental program
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example 1

Synthesis Of Polyethylene Glycol Disuccinimidyl Succinate PEG-SS2

[0033]Polyethylene glycol, PEG, (50 g, Aldrich Chemical Company, Milwaukee, Wis., sold as 3,400 average molecular weight, GPC analysis Mn was 2,980, Mw, was 3,480) was dissolved in 1,2-dichloroethane (250 ml) containing succinic arthydride (14.7 g) and anhydrous pyridine (12 ml). The mixture was refluxed under nitrogen for three days. After filtration and evaporation of the solvent, the residue was dissolved in 100 ml water and treated with the cation exchange resin Dowex™ 50 (H+) (50 g) for 30 minutes. The mixture was then filtered and the Dowex™ 50 was washed with water (50 ml 1×). The combined filtrate was washed with anhydrous diethyl ether (50 ml 2×). The PEG-disuccinate was then extracted from the water phase with two 100 ml chloroform washes. Evaporation of chloroform yielded about 49 g of PEG-disuccinate.

[0034]The PEG-disuccinate was dissolved in 200 ml N,N-dimethylformamide (DMF) at 37° C. and 4.23 g of N-hydr...

example 2

Synthesis of N-hydroxysuccinimide Ester of Dicarboxymethyl Polyethylene Glycol

[0035]Dicarboxymethyl poly(ethylene glycol) (mol. wt. 3400) purchased from Shearwater Polymers, Inc., Huntsville, Ala. (5 g) and N-hydroxysuccinimide purchased from Sigma Chemical Co., St. Louis, Mo. (1 g) were dissolved in 30 ml of anhydrous DMF with mechanical stirring under nitrogen. The solution was cooled to 0° C. and a solution of dicyclohexylcarbodiimide (1.79 g) in 5 ml DMF was added dropwise. The stirring was continued in the cold for 3 hours then at room temperature overnight (16 hrs). Dicyclohexylurea which precipitated was removed by filtration. Toluene (100 ml) was added to the filtrate and cooled to 0° C. The product was then precipitated by addition of petroleum ether. The precipitate was collected on a sintered glass filter. Dissolution in toluene and reprecipitation with petroleum ether was repeated three times. The product was dried under vacuum in a desiccator.

example 3

Synthesis of Polyethylene Glycol-di-oligoglycolide Disuccinimidyl Succinate

[0036]A 500 ml three neck round bottom flask was flame dried under nitrogen. 50 g of PEG (mol. wt. 3400), 300 ml of xylene, and 1 drop of 0.33M stannous ottoate solution in xylene were charged into the flask with a continuous nitrogen purge. The flask was heated to boil the solution and 50 ml of xylene were removed by distillation. The solution was then cooled to room temperature. 17 g of glycolide (Boehfinger Ingleheim KG, Ingleheim, Germany) was added to the flask and the reaction mixture was refluxed under nitrogen for 16 hours. The copolymer reaction mixture was filtered hot to remove polyglycolide homopolymer. The copolymer then precipitated from the filtrate upon cooling and collected by filtration. The copolymer was placed in a flask with 500 ml of dichloromethane and 7 g of succinyl chloride. The solution was refluxed under nitrogen overnight (16 hours). 8.5 g of N-hydroxysuccinimide was added to the ...

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Abstract

This invention is related to an adhesive composition which may be used to bond or seal tissue in vivo. The adhesive composition is readily formed from a two component mixture which includes a first part of a protein, preferably a serum albumin protein, in an aqueous buffer having a pH in the range of about 8.0-11.0 and a second part of a water-compatible or water-soluble bifunctional crosslinking agent. When the two parts of the mixture are combined, the mixture is initially a liquid which cures in vivo on the surface of tissue in less than about one minute to give a strong, flexible, pliant substantive composition which bonds to the tissue and is absorbed in about four to sixty days. The adhesive composition may be used either to bond tissue, to seal tissue or to prevent tissue adhesions caused by surgery.

Description

[0001]Notice: More than one reissue application has been filed for the reissue of U.S. Pat. No. 5,583,114. The reissue applications are application Ser. No. 10 / 293,989, filed Nov. 14, 2002, and application Ser. No. 09 / 185,732, filed Nov. 4, 1998, now U.S. Pat. Re 38,158, all of which are reissues of U.S. Pat. No. 5,583,114.[0002]This application is a continuation of reissue application Ser. No. 09 / 185,732, filed Nov. 4, 1998, now U.S. Pat. No. RE 38,158, issued Jun. 24, 2003, which is a reissue of U.S. Pat. No. 5,583,114.[0003]The present invention is generally related to an adhesive sealant composition which may be used to bond or seal tissue in vivo and is particularly related to a two component, liquid adhesive composition which is mixed together as it is applied to tissue and then cured in vivo in order to bond tissue, to seal tissue to prevent or control pulmonary system air leaks, or to prevent tissue adhesions caused by surgery.BACKGROUND[0004]A variety of techniques have bee...

Claims

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Application Information

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IPC IPC(8): A61L24/00A61L24/04C09J189/00
CPCA61L24/043A61L24/046C09J189/00C08L89/00
Inventor BARROWS, THOMAS H.LEWIS, TERRY W.TRUONG, MYHANH T.SCHOLZ, MATTHEW T.
Owner NEOMEND INC
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