Hydrophilic biodegradable adhesives

FIELD: chemistry.

SUBSTANCE: moisture-curable and biodegradable adhesive which contains a reaction product of: (a) an isocyanate component having an average functionality of at least 2, the isocyanate component being selected from a group consisting of lysine diisocyanate and derivatives thereof, lysine triisocyanate and derivatives thereof, and combinations thereof; (b) an active hydrogen component having an average functionality greater than 2.1, the active hydrogen component containing a component with a hydroxyl functional group; and (c) an ionic salt component having an average hydroxyl or amino functionality, or combination thereof, of at least 1, selected from a group consisting of ammonium salts, halides, sulphonates, phosphonates, carboxylates and combinations thereof.

EFFECT: obtaining a moisture-curable and biodegradable adhesive.

18 cl, 1 dwg, 17 ex

 

The reference to related applications

This application is related to the application U.S.S.N. 12/123927, filed may 20, 2008, which is partly continuing application under review application Beckman et al., “Hydrophilic Biodegradable Adhesives”, U.S.S.N. 11/781539, filed July 23, 2007, owned by the same assignee as this application, and incorporated herein by reference.

The technical field to which the invention relates

The present invention relates to the bonding of biological tissues.

The level of technology

Biological and synthetic tissue adhesives have been developed for bonding biological tissue as an alternative suture material and brackets. Examples of biological tissue adhesives include fibrin glues. Examples of synthetic tissue adhesives include cyanoacrylate, urethane prepolymers and gelatin-resorcinol-formaldehyde. The possibility of applying adhesives to join biological tissues are in the range from soft (connective) bonding to hard (calcined) bonding. Soft tissue glue is used both externally and internally for suturing wounds and sealing. Hard tissue adhesives are used where the connection material of the denture teeth and bones.

The invention

Described adhesive, which include the AET the reaction product of: (a) isocyanate component, having an average functionality of at least 2; (b) an active hydrogen component having an average functionality of more than 2.1; and (C) component, which represents an ionic salt, with an average hydroxyl or amine functionality, or a combination of at least 1. This adhesive is a moisture curing and biodegradable and can be applied to soft or hard biological tissue.

The term "component" refers to the individual compounds and mixtures of different compounds.

This adhesive may also include a catalyst, a solvent, a volatile solvent, non-volatile diluent, or a combination of both. The term "volatile" solvent refers to a solvent having a boiling point at atmospheric pressure which is less than or equal to 40°C. in Contrast, the term "non-volatile" solvent refers to a solvent having a boiling point at atmospheric pressure of more than 40°C. In some embodiments of the invention, the adhesive may take the form of a sprayable composition.

The inclusion of ionic salts, which interacts with the isocyanate component of this composition and, thus, forms a covalent bond with the adhesive, increases the hydrophilicity of the adhesive compared to the adhesive, in which the ionic salt is missing. Due to increased hydrophilicity in turn may increase about the ability of adhesion of the adhesive and the biological tissue. It can also improve the solubility of other hydrophilic agents, such as compounds containing hydroxyl group, what more could increase the overall hydrophilicity of the adhesive.

The following descriptions detail in relation to one or more embodiments of the invention. Other features, objectives and advantages will become apparent from the description, drawing and claims.

Brief description of drawings

Figure 1 presents a schematic of the test device used to measure the bonding strength.

Detailed description of the invention

Describes adhesives suitable for use on soft and hard biological tissue, comprising the reaction product of: (a) isocyanate component having an average functionality of at least 2; (b) an active hydrogen component having an average functionality of more than 2.1; and (C) component, which represents an ionic salt, with an average hydroxyl or amine functionality, or a combination of at least 1. When applied to the biological tissue in the presence of moisture in the adhesive is cross-stitching with the formation of the polymer network. Over time, this Poperechnaya mesh biodegradable. For example, biological laid out what may happen in that time, within which healing. The grid may, for example, to remain whole and glue tissue lacerations or incised wounds as long as the degree of healing will not be sufficient to wound remained closed. It may take some time, for example, a few days or months, depending on the glue.

Isocyanate component has an average isocyanate functionality of at least 2, maybe at least 3. The term "average" reflects the fact that the multi-functional isocyanate component, as explained in the section "summary of the invention"described above, may include numerous types of isocyanates, including isocyanates with different functional groups. Suitable are hydrophilic isocyanates, which include isocyanates derived from amino acids and derivatives of amino acids. Specific examples include liaindizecign (LDI) and its derivatives (for example, a complex alkalemia esters, such as complex methyl or ethyl ester) and disinclination (LTI) and its derivatives (for example, a complex alkalemia esters, such as complex methyl or ethyl ester). Can also be used dipeptide derivatives. For example, the lysine may be combined in the dipeptide with another amino acid (e.g., valine or glycine).

Active hydrogen whom onent includes one or more active hydrogen reactants. This component has an average functionality of more than 2.1. In this case, the term "average" reflects the fact that the active hydrogen component, as explained in the section "summary of the invention"described above, may include numerous types of active hydrogen reagents, including reagents with different functional groups. Some or all of the active hydrogen reactants can have an equivalent weight less than 100. The term "equivalent weight" refers to the molecular weight divided by functionality. So, for example, glycerol, molecular weight which is equal to 92, and a hydroxyl functionality "f" is equal to 3, has an equivalent weight of approximately 31.

Examples of suitable active hydrogen components include components with a hydroxyl functional group components with amine functional group components with tylenol functional group components with the functional group of carboxylic acid, and combinations thereof. In some embodiments of the invention some or all of the functional groups can be primary groups.

One class of suitable active hydrogen component comprises a multifunctional alcohol selected from glycerol, diglycerin, eritria, pentaerythritol, xylitol, Arabica, fuzeta, ribit, sorbitol, mannitol and their combinazione are suitable hydroxyalkyl derivatives and esters of any of these alcohols, such as ethoxylated pentaerythritol.

Another class of suitable active hydrogen component comprises hydroxyalkyl derivatives of carboxylic or dicarboxylic acids With3-C10(for example, dimethylolpropionic acid, dimethylaniline acid and combinations thereof, and hydroxyalkyl derivatives of hydrocarbons With3-C10(for example, trimethylolpropane).

The active hydrogen component can also be hydroxyalkylated (e.g., triethanolamine), di-, tri - or tetraalkyllead or a combination thereof. Also suitable are compounds with a hydroxyl functional group selected from saccharides (e.g. glucose, fructose, sucrose or lactose), oligosaccharides, polysaccharides, their esters and combinations thereof.

Ionic salt contains one or more hydroxyl and/or amine functional groups. Therefore, it is able to react with a component of this reaction mixture containing isocyanate functional group, in consequence of which forms a covalent bond with the adhesive. Examples of suitable salts include ammonium salts, halides, sulfonates, phosphonates, carboxylates, and combinations thereof. Specific examples include ammonium halides (such as chloride of ethyldiethanolamine and chloride bis(2-hydroxyethyl)dimethylammonio), halides hall is on (for example, choline chloride), and combinations thereof.

The adhesive may optionally include a catalyst. Examples of suitable catalysts include tertiary amines (for example, aliphatic tertiary amines and ORGANOMETALLIC compounds (for example, salts of bismuth and zirconium chelates). Specific examples include 1,4-diazabicyclo[2.2.2]octane (DABCO), 2,2'-demoralization ether (DMDEE), dilaurate dibutyrate (DBTDL), 2-ethylhexanoate, bismuth, and combinations thereof. The amount of catalyst is chosen depending on the particular reagents.

The adhesive may also include a rheology modifier in the form of solvent, non-volatile diluent and/or volatile diluent. Examples of suitable solvents include dimethylsulfoxide (DMSO), dimethylformamide (DMF), tetrahydrofuran (THF), glyme, and combinations thereof. Examples of suitable non-volatile solvents include dimethylsulfoxide (DMSO), propylene carbonate, diglyme, diacetate of polyethylene glycol, dicarbamate of polyethylene glycol, dimetridazole and combinations thereof. Examples of suitable volatile solvents include hydrocarbons, perftoran, hydrofluroalkane, carbon dioxide, and combinations thereof. One agent can perform many functions. So, for example, DMSO can act as both solvent and non-volatile diluent. The amount of rheology modifier is chosen dependent on the STI from the constituents of this adhesive and certain application, for which the adhesive is intended.

Adhesives can also include one or more stabilizers. Examples thereof include antioxidants (such as BHT and BHA), the sinks of water (for example, acylhomoserine and aryl halides and anhydrides, acid of Branstad etc.

The curing time of the adhesive can be modified to meet the requirements of the specific application for which the adhesive is intended. For example, the curing time in the range of from about 1 minute to about 45 minutes can be achieved by combining this glue with some water alkaline solution (such as aqueous NaOH or KOH) immediately before use. Usually, the amount of water added to this glue is from 50 to 200% of the number required for the interactions with all the free isocyanate groups in the adhesive, while the amount of base is from about 100 to 200% of the amount required to neutralize the acid (for example, N2SO4), which is part of the glue.

In some embodiments of the invention, the adhesive has the form of a sprayable composition. Such adhesives typically have a viscosity, measured at 25°C. of the order of not more than 5000 CPs (for example, from 1 to 3000 CP).

These adhesives are suitable in different applications. They can be used in owani for bonding substances with materials of the following General categories, and for bonding these materials with each other:

(1) soft tissue (e.g. muscle, fat, skin, skin muscles, tendons and the like);

(2) hard tissue (e.g. bone, cartilage, etc.);

(3) materials of biological origin (e.g., extracellular matrix, submucosal membrane of the small intestine, collage, frames, obtained by the methods of tissue engineering, and the like);

(4) synthetic materials (for example, films and nets made from polymers such as polyester, polypropylene and the like);

(5) metal and inorganic implants (e.g., orthopedic metal joint prostheses, hydroxyapatite bone substitutes and the like);

(6) tissue grafts (e.g., allografts, xenografts, autotransplants and so on).

For example, these adhesives can be used instead of the suture material and brackets to connect with each other soft tissues during surgery or as part of the Protocol of wound healing. Alternatively, these adhesives can be used for adhesion of the polymer film or mesh (e.g., mesh polypropylene) to the tissue, for example, in order to restore tearing of soft tissues, such as hernia repair. In the case of this application, the adhesive may be designed to provide a fast curing (e.g., within 5 mi the ut after the application), for example, by combining this adhesive with an aqueous alkaline solution immediately before use. This adhesive replaces suture material and brackets, traditionally used for bonding synthetic mesh with muscles.

Glue and mesh or film can be obtained separately (for example, in the form of a set) and then the joint during use. For example, during use, the adhesive may be applied to the entire surface or part of the surface of the mesh or film on one or both sides, and the resulting product is then placed on the fabric. Alternatively, adhesive may be applied to the fabric with the subsequent imposition of mesh or film. Can also be used multiple layers of mesh or film, glued to each other using this glue. You can also combine glue and mesh or film before use. For example, the adhesive can be introduced into the mesh or film, or applied to the entire surface or part of the surface of the mesh or film on one or both sides.

EXAMPLES

Example 1

Choline chloride (CC), trimethylolpropane (TSR) and ethoxylated pentaerythritol (EP) in dimethyl sulfoxide (DMSO) 2-argentinita bismuth (BIS) and demoralization ether (DMDEE)

1,96 g TSR (14.6 mmol, HE is 43.8 mmol), 0,60 g SS (4.3 mmol, HE 4.3 mmol), and 0.46 g EP (1.7 mmol, HE 6,8 mmol) and 7,34 g of DMSO was stirred in n is a large glass tank high pressure at 60°C until complete dissolution of all components. Then added 11,88 g LDI (56.0 mmol, -NCO 112,0 mmol) and stirred the contents at 60°C for 30 minutes. The tank was kept in an ice bath for 15 minutes, then was added 33.3 mg BIS, 222 μl DMDEE and 1.9 mg of dye FD&C blue No. 1. The tank was kept in an ice bath with stirring for 30 minutes and then at room temperature for 1.5 hours. After this was added to 11.1 μl of sulfuric acid and 20.8 mg of butyric acid hydroxytoluene to increase shelf life and was stirred for 15 minutes. Viscous liquid (~500 CPS (at 25°C) was kept at room temperature. The glue was sprayed on bovine muscle tissue using a device powered by compressed air. After standing for 1 minute pieces of tissue were clasped in each other. After ~5-10 minutes these fabrics are firmly held together.

Example 2

TSR, CP and EP in DMSO and 1,1,1,3,3-pentafluoropropane (F-245fa) with BIS and DMDEE

1,96 g TSR (14.6 mmol, HE is 43.8 mmol), 0,60 g SS (4.3 mmol, HE 4.3 mmol), and 0.46 g EP (1.7 mmol, HE 6,8 mmol) and 2.70 g of DMSO were mixed in a small glass tank high pressure at 60°C until complete dissolution of all components. Then added 11,88 g LDI (56.0 mmol, -NCO 112,0 mmol) and stirred the contents at 60°C for 30 minutes. The closed vessel was kept in an ice bath for 15 minutes, then added 9,49 mg F-245fa and stirred until the tank Homo the military mix. Still in an ice bath was added 26,4 mg BIS, 176 μl of DMDEE and 1.5 mg of dye FD&C blue No. 1, stirring for 30 minutes, then stirred at room temperature for 1.5 hours. The tank was kept in an ice bath for 15 minutes, then added to 7.3 μl of sulfuric acid and 13.7 mg of butyric acid hydroxytoluene to increase shelf life. The contents of the vessel were stirred for 30 minutes at room temperature and a viscous liquid was stored at 4°C. a Viscous liquid (<5000 CPS (at 25°C) was distributed on bovine muscle tissue and after standing for 1 minute pieces of fabric glued to each other.

Example 3

Xylitol and SS in DMSO and F-245fa with BIS and DMDEE

Xylitol and SS in a mass ratio of xylitol:SS 2:1 was stirred at 70°C as long as they do not form a homogeneous liquid phase. This liquid was cooled and 1.50 g of a mixture of xylitol/SS (xylitol: 6.6 mmol, HE 32,9 mmol; SS: 4.3 mmol, HE 4.3 mmol) was combined with 7,73 g LDI cases (36.4 mmol, -NCO of 72.9 mmol) and 2.52 g of DMSO in a closed small glass tank high pressure. The tank was heated up to 70°C and the contents were stirred for 30 minutes. The tank was kept in an ice bath for 15 minutes, then added 5,04 g F-245fa and stirred at room temperature for 10 minutes. The tank was kept in an ice bath for 10 minutes. Added BIS 3 aliquot of the total number to 35.3 mg, PE is anesiva within 10 minutes between additions. During recent additions BIS was added DMDEE (111 μl). The contents of the vessel were stirred at room temperature for 1.5 hours and then kept at 4°C. the Adhesive is distributed on bovine muscle tissue. After standing for one minute pieces of cloth pressed to each other. After ~5-10 minutes these fabrics are firmly held together.

Example 4

TSR, CP and EP in propylene carbonate (PC) and F-245fa with BIS and DMDEE

0,98 g TSR (7,3 mmol, HE 21.9 mmol), 0,30 g SS (2.2 mmol, HE 2.2 mmol), 0,23 g EP (0.9 mmol, HE 3,4 mmol) and 2.24 g RS mixed in a small glass tank high pressure at 70°C until complete dissolution of all components. Then added 5,94 g LDI (28,0 mmol, -NCO 56.0 mmol) and stirred the contents at 70°C for 30 minutes. The tank was kept in an ice bath for 15 minutes. Added F-245fa two equal aliquot total number total of 5.21 g under stirring between additions for approximately 10 minutes. BIS was added 3 aliquot of the total number of 29.1 mg with stirring between additions within 10 minutes. During recent additions BIS was added DMDEE (97 μl). The contents of the vessel were stirred at room temperature for 30 minutes and then kept at 4°C. the Adhesive is distributed on bovine muscle tissue. After standing for one minute pieces of cloth pressed to each other. the via several minutes, the pieces of fabric were firmly glued together.

Example 5

TSR, CP and EP in diethyl ether of isosorbide (IDE) and F-245fa with BIS and DMDEE

0,98 g TSR (7,3 mmol, HE 21.9 mmol), 0,30 g SS (2.2 mmol, HE 2.2 mmol), 0,23 g EP (0.9 mmol, HE 3,4 mmol) and 2.24 g IDE mixed in a small glass tank high pressure at 70°C until complete dissolution of all components. Then added 5,94 g LDI (28,0 mmol, -NCO 56.0 mmol) and stirred the contents at 70°C for 30 minutes. The tank was kept in an ice bath for 15 minutes. Added F-245fa two equal aliquot total number total of 5.21 g under stirring between additions for approximately 10 minutes. Added BIS 3 aliquot of the total number of 29.1 mg with stirring between additions within 10 minutes. During recent additions BIS was added DMDEE (97 μl). The contents of the vessel were stirred at room temperature for 30 minutes and then kept at 4°C. the Adhesive is distributed on bovine muscle tissue. After standing for one minute pieces of cloth pressed to each other. After ~5-10 minutes these fabrics are firmly held together.

Example 6

TSR, xylitol, CP and EP in DMSO and F-245fa with BIS and DMDEE

Xylitol and SS in a mass ratio of xylitol:SS 2:1 was stirred at 70°C as long as they do not form a homogeneous liquid phase. This liquid was cooled, 0,38 g of a mixture of xylitol/SS (xylitol: 1.6 mmol, HE 8,2 mmol; SS: 0.9 mmol, -is N 0.9 mmol) was combined with 1,14 g TSR (8.5 mmol, HE 25.5 mmol), 7,27 g LDI (34,3 mmol, -NCO and 68.5 mmol) and 0.74 g of DMSO in a small glass tank high pressure at 60°C and was stirred for 30 minutes. The tank was kept in an ice bath for 15 minutes, then added 5,14 g F-245fa and stirred at room temperature for 20 minutes. The tank was kept in an ice bath for 10 minutes. Added BIS 3 aliquot of the total number 28.5 mg under stirring for 10 minutes between additions. During recent additions BIS was added DMDEE (90 μl). The contents of the vessel were stirred at room temperature for 30 minutes and kept at 4°C. the Adhesive is distributed on bovine muscle tissue and after standing for one minute pieces of cloth pressed to each other. After a few minutes, these fabrics are firmly glued to each other.

Example 7

Glycerin, xylitol and SS in DMSO and F-245fa with BIS and DMDEE

of 0.77 g of glycerin (8.4 mmol, HE is 25.1 mmol), 0.55 g of xylitol (3.6 mmol, HE 18,1 mmol), 0.27 g SS (1.9 mmol, HE is 1.9 mmol), 9.60 g LDI (45,2 mmol, -NCO 90,5 mmol) and of 1.87 g of DMSO were mixed in a small glass tank high pressure at 70°C for 30 minutes. The tank was kept in an ice bath for 15 minutes, was added 5,64 g F-245fa and stirred in an ice bath to obtain a homogeneous mixture. After this was added to 32.9 mg BIS and 89 μl DMDEE. The contents of the reservoir is of Varos was stirred in an ice bath for 1 hour and then kept at 4°C. The adhesive is distributed on bovine muscle tissue. After standing for one minute pieces of cloth pressed to each other. After a few minutes, these fabrics are firmly glued to each other.

Example 8

Triethanolamine (tea) and the SS in DMSO with BIS and DMDEE

1,00 g TEM (6.7 mmol, HE 20,1 mmol), 0.31 g SS (2.2 mmol, HE 2.2 mmol) and of 4.00 g of DMSO was stirred at 70°C in a test tube with a volume of 20 ml to obtain a homogeneous phase. The solution was cooled to room temperature, then added 4,74 g LDI. The solution was stirred for 10 minutes and then transferred to an ice bath. Added BIS two equal aliquot total of 15.1 mg under stirring for 10 minutes in an ice bath between additions. During recent additions BIS was added DMDEE (50 μl). The composition was stirred in an ice bath for an additional 10 minutes, then at room temperature for 40 minutes. Viscous liquid distributed on bovine muscle tissue. After standing for one minute pieces of cloth pressed to each other. After ~5-10 minutes these fabrics are firmly glued to each other.

Example 9

TSR and chloride bis(hydroxyethyl)dimethylammonio (BHDMAC) in DMSO and pentafluorobutane + heptadecene (F-365 + F-227) with BIS and DMDEE

0,93 g TSR (7,3 mmol) and 0.36 g BHDMAC (2.1 mmol) was dissolved in 1.27 g DMSO at 50°C in a glass tube of a high pressure volume 75 cm3 with screw-on lid made of Teflon®. Then the solution was cooled to room temperature and with stirring was added 49,7 ml solution of 0.1 g/ml BIS in DMSO. Then added 5,67 g methyl ester LDI (26,75 mmol), after which the temperature was rapidly increased to 70-80°C, and then decreased. After 10 additional minutes were added 24,8 μl of a solution of BIS. 10 minutes after the last addition of BIS study product by the method of IR spectroscopy showed the characteristic bands of the secondary urethane NH (3250 cm-1), NCO group (2245-2255 cm-1), bands of amides I and II (1714 and 1533 cm-1) and ether LDI (1741 cm-1). The product was cooled to about 7°C in an ice bath, and then added of 4.45 g of a mixture of 93:7 F-365 and F-227. The resulting mixture was stirred with a magnetic stirrer to obtain a homogeneous transparent phase. Then under stirring was added 82,8 ál DMDEE. Finally, added 128 μl of solution 0,216 cm3/3,79 cm3sulfuric acid in DMSO to obtain glue.

This glue in the number 0,5335 g) was combined with 10.1 μl of solution 0,1446 g KOH in 10,7327 g deionized water for the purpose of curing of the adhesive. Measured time of curing, which accounted for 37 minutes.

Example 10

Repeating example 9, except that 1,0095 g glue combined from 19.1 μl of solution 0,2048 g KOH in 5,0878 g of deionized water for curing of the adhesive. Measured time of curing, which accounted for the ILO 13 minutes.

Example 11

Repeating example 9, except that 0,999 g glue combined with 18.9 μl of solution 0,2057 g KOH in 3,8263 g of deionized water for curing of the adhesive. Measured time of curing, which amounted to 7 minutes.

Example 12

Repeating example 9, except that 1,099 g glue combined with 38,1 μl of solution 0,2057 g KOH in 3,8263 g of deionized water for curing of the adhesive. Measured time of curing, which amounted to 1.5 minutes.

Example 13

Repeating example 9, except that 1,0968 g glue combined from 41.5 μl of a solution 0,1446 g KOH in 10,7327 g of deionized water for curing of the adhesive. Measured time of curing, which amounted to 4 minutes.

Example 14

Repeating example 9, except that 0,9979 g glue combined with 37,7 μl of solution 0,0463 g KOH in 6,9065 g of deionized water for curing of the adhesive. Measured time of curing, which amounted to 7 minutes.

Example 15

In the local grocery store bought piece bistensee part of the flank, from which universal knife cut a round sample of 12.5, see this sample the same knife or scalpel made 3-cm incision. A sample of polypropylene Prolen mesh (Ethicon, Inc.) the size of 3 cm × 5 cm was placed on the incision (5 cm parallel to the slit).

At this time, approximately 2 grams of the adhesive of example 9 weigh-in & m what does plastic saucer weights, added a quantity of a solution 0,2057 g KOH in 3,8263 g of deionized water, corresponding to 19 µl/g glue. The mixture was stirred for 15 seconds, then smeared around the edges of the grid with the help of a spatula. After 30 minutes, the adhesive strength of the adhesive, mesh and a piece of meat was investigated as follows.

Bond strength was measured using the test device, played by mechanized test bench Mark-10 ESM, equipped with a digital dynamometer with maximum load of 200 pounds (90,7 kg). The dynamometer was attached to the movable upper frame of the test bench so that directed downwards force applied by the device for the application of force (round rubber hemisphere, approximately 2 inches (5 cm) in diameter), can be measured. The testing device is shown schematically in figure 1.

The meat block/grid/adhesive mesh down was placed on a tripod ring, which was attached to the bottom plate of the test stand. Ring tripod provided six points of attachment along the edge of the piece of meat, leaving the Central part of sagging down under the action of the device for the application of force. Device for application of force was moved down at a speed of 2 inches/min (5 cm/min) up until at least one attached with glue area was not separated from the meat tissue Attached at that time the force was measured and recorded. In this experiment, when a force of 25 N. the grid is separated from the meat by breaking the adhesive connection.

Example 16

Repeating the procedure of example 15, using instead polypropylene Prolen mesh soft mesh Soft Mesh) from Bard, Inc. To separate the grid from the meat by breaking the adhesive connection required force 30 N.

Example 17

Repeating the procedure of example 16, except that the adhesive was applied only to the four corners of the grid. To separate the grid from the meat by breaking the adhesive connection required strength 35 N.

This document describes a number of embodiments of the invention. However, it should be understood that various modifications may be made without departure from the essence and scope of the invention. Therefore, other embodiments of the invention are included in the scope defined by the following claims.

1. Adhesive comprising the reaction product of:
(a) an isocyanate component having an average functionality of at least 2; where the isocyanate component is selected from the group consisting of lizenzierte and its derivatives, disinclination and its derivatives and their combinations
(b) an active hydrogen component having an average functionality of more than 2.1; where the active hydrogen component comprises a component with a hydroxyl functional group, and
(c) whom Oneonta, represents an ionic salt with an average hydroxyl or amine functionality, or a combination of at least 1, which is selected from the group consisting of ammonium salts, halides, sulfonates, phosphonates, carboxylates, and combinations thereof, which adhesive is a moisture curing and biodegradable.

2. The adhesive according to claim 1, in which each active hydrogen component has an equivalent weight less than 100.

3. The adhesive according to claim 1, in which the active hydrogen component consists essentially of components with primary hydroxyl groups, primary aminovymi groups and their combinations.

4. The adhesive according to claim 1, in which the active hydrogen component is selected from the group consisting of glycerol, diglycerin, eritria, pentaerythritol, xylitol, Arabica, fuzeta, ribit, sorbitol, mannitol, hydroxyalkyl derivatives, their esters and combinations thereof.

5. The adhesive according to claim 1, in which the active hydrogen component comprises hydroxyalkyl derivatives of carboxylic or dicarboxylic acids With3-C10.

6. The adhesive according to claim 1, in which the active hydrogen component comprises hydroxyalkyl derivatives of hydrocarbons With3-C10.

7. The adhesive according to claim 1, in which the active hydrogen component comprises hydroxyalkylated.

8. The adhesive according to claim 1, in which the active hydrogen component comprises di-, tri - is whether tetraalkyllead or a combination of both.

9. The adhesive according to claim 1, in which the active hydrogen component is selected from the group consisting of saccharides, oligosaccharides, polysaccharides, their esters and combinations thereof.

10. Adhesive of claim 1, wherein the adhesive additionally contains a catalyst, solvent, non-volatile or volatile diluent diluent, individually or in combination.

11. The adhesive according to claim 1, including
(A) reaction product:
(a) an isocyanate component having an average functionality of at least 2;
(b) component with a hydroxyl functional group having an average functionality of more than 2.1; and
(c) a component representing the ionic salt, with an average hydroxyl or amine functionality, or a combination of at least 1;
(B) a solvent, non-volatile diluent, or a combination of the
(C) a volatile diluent selected from the group consisting of hydrofluroalkane, performancenow and their combinations.

12. The method for bonding biological tissue, comprising applying the adhesive according to claim 1 or 11 on the cloth.

13. The method according to item 12, in which the fabric comprises a soft biological tissue.

14. The method according to item 12, which includes the Association of the adhesive with an aqueous alkaline solution prior to applying the adhesive to the fabric.

15. The method according to item 12, which includes the gluing data of glue to the fabric of polymeric mesh or film.

16. The method according to item 12, including the reduction of Olenye tearing of the soft tissue by sticking this adhesive polymer mesh or foil to the soft tissue near the gap.

17. The kit includes (a) a polymer mesh or film and (b) moisture curing and biodegradable adhesive according to claim 1 or claim 11.

18. The product, including (a) a polymer mesh or film and (b) moisture curing and biodegradable adhesive according to claim 1 or 11, located on or within the polymeric mesh or film.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: adhesive polyurethane composition consists of a prime coat and polyurethane adhesive, comprising urethane rubber and ethyl acetate, applied on its surface. The prime coat consists of a solution of polyurethane thermoplastic elastomer with ethyl acetate in ratio: polyurethane thermoplastic elastomer 10-18 wt % and ethyl acetate - the balance. The polyurethane adhesive contains a solution of polyurethane thermoplastic elastomer and a mixture of polar organic solvents consisting of ethyl acetate and methylene chloride, with the following ratio of components: polyurethane thermoplastic elastomer 17-27 wt %; methylene chloride 7-10 wt % and ethyl acetate - the balance. The polyurethane adhesive can contain perchlorovinyl resin as a target additive in amount of 0-10% to the total weight of the adhesive.

EFFECT: low cost and improved adhesion properties of the adhesive composition and cohesion strength characteristics of the adhesive joints.

2 cl, 2 tbl

FIELD: chemistry.

SUBSTANCE: composition contains the following in pts.wt: 100 bifunctional prepolymer with terminal isocyanate groups, 10.6-12.8 - 3,3'-dichloro-4,4'-diaminodiphenylmethane, 15.9-19.2 dioctylsebacate, 1.2-1.4 - 1,4-butanediol, 0.31-0.35 - para-phenylenediamine and 0.015-0.030 - Agidol 51,52,53 (mixture of 2-dimethylaminomethylphenol, 4-dimethylaminophenol, 2,6-bis (dimethylaminomethyl)phenol, 2,4-bis-(dimethylaminomethyl)phenol,2,4,6-tris-dimethylaminomethyl)phenol.

EFFECT: obtaining a fixing composition which, after prolonged storage, retains strength and adhesion parameters vital for operation of charges of antitank grenades at both high and low temperatures, and also prevents accidental exposure to substances which are harmful to health of personnel, in cases of technical faults and emergencies.

3 tbl

FIELD: transport.

SUBSTANCE: invention relates to method for covering light airplanes with polyester sheathing fabric, as well as to dispersive hot-gluing glue and its application for covering. For covering, polyester sheathing fabric with longitudinal shrinkage of 7% and transversal shrinkage of 5% at 160-180°C is used. In the process of covering light airplanes and/or their parts consisting of frame system, sheathing fabric in the area of its overhangs and frame parts is covered by dispersive hot-gluing glue and wrapped around longeron part of frame so that when connection between sheathing fabric and frame produced by glue is destructed the fabric could be held on frame carcass. Dispersive hot-gluing glue contains 80-88% of adhesive, 12-15% of hardener and 0.15-0.3% thickener, and the glue is polymerised at temperatures >40°C. The hardener contains 54-60% of solvent, 0.35-0.5% of naphthalensulfonic acid sodium salt-based stabiliser, 0.25-0.35% of propoxylated spirit-based emulsifier, 1.7-1.9% of polyetheramines-based hardener, 37-41% of polyisocyanate.

EFFECT: reliability and durability of light airplanes and/or their parts covering.

15 cl, 3 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to aldimines of formula (I)

where A does not contain active hydrogen and a primary amine group, or together with R7 denotes a (n+2)-valent hydrocarbon radical containing 3-20 carbon atoms and, if necessary, at least one heteroatom in form of oxygen of an ether group or nitrogen or a tertiary amine group; n equals 1, 2, 3 or 4; m equals 0,1, 2, 3 or 4; R1 and R2 each denotes a univalent hydrocarbon residue with 1-12 carbon atoms or together denote a divalent hydrocarbon radical which is part of a carbocyclic ring with 5-8 carbon atoms; R3 denotes H or alkyl; R4 and R5 independently denote CH3 or a univalent aliphatic radical containing 2-12 carbon atoms and optionally hydroxy groups; X denotes O, S, N-R6, or N-R7, where R6 denotes a univalent hydrocarbon radical containing 1-20 carbon atoms and having at least one hydroxy group; as well as curable compositions containing such aldimines and use of said compositions.

EFFECT: obtaining novel aldimines which can be used as curing agents in curable compositions.

22 cl, 18 ex, 6 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to a polyisocyanurate based adhesive which is obtained by reacting an organic polyisocyanate with a compound containing hydrogen atoms which are reactive towards isocyanate, in the presence of a trimerisation catalyst. The organic polyisocyanate is a polymer or prepolymer polyisocyanate, and content of the soft block in the adhesive ranges from 40 to 60 wt %. A reaction mixture for producing said adhesive is also described.

EFFECT: obtaining an adhesive capable of withstanding high maximum stress, having extremely fast setting and having a good and strong bond with the base, as well as high thermal stability, resistance to salty water and creep.

9 cl, 4 ex, 6 tbl

Gluing method // 2451040

FIELD: chemistry.

SUBSTANCE: method involves applying a UV curable adhesive resin composition, containing a photolatent base, onto at least one transparent surface of at least one of a first and a second substrate. The substrates are then brought together so that said adhesive composition lies in between. The adhesive composition is then exposed to actinic radiation for curing. The UV curable adhesive is a OH/NCO system or SH/NCO system. In another version of the gluing method, the first and second substrates are brought together after exposing the adhesive composition in between to actinic radiation.

EFFECT: disclosed gluing method enables faster curing of the adhesive.

5 cl, 10 tbl, 6 ex

FIELD: chemistry.

SUBSTANCE: composition contains one or more urethane prepolymers, having isocyanate residues, one or more compounds which catalyse the reaction of isocyanate residues with water or a compound which contains active hydrogen and one or more alpha-hydrocarbyl silane compounds. The urethane propolymer additionally contains a silane functional group. The composition additionally contains a compound or a polymer, containing silane residues. The composition additionally contains one or more compounds which catalyse silanol condensation. The composition is deposited onto the surface of glass or plastic with a coating or onto the surface of a substrate to obtain a sealant, then brought into contact and the composition is then hardened. The composition is placed between the glass or plastic with coating and the substrate. The sealing composition is used for binding an unprimed surface with a coating, such as a window lintel with glass with a transparent plastic, coated with an abrasive-resistant coating or with glass or plastic with a coating, additionally coated with glass cement, such as ceramic or organic glass cement.

EFFECT: improved composition properties.

10 cl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing dispersions of blocked polyurethane prepolymers, use of dispersions obtained using said method to produce coating agents, adhesive substances and sealants and elastomers, said application products themselves, as well as substrates provided with coating agents. The method involves the following: I) a blocked polyurethane prepolymer is obtained first by reacting a) 100 equivalent % of at least one polyisocyanate with b) 50-90 equivalent %, in terms of isocyanate reactive groups, of a thermally split blocking agent, c) 5-45 equivalent %, in terms of isocyanate reactive groups, monohydroxycarboxylic acid as a hydrophilic agent and d) 0-25 equivalent %, in terms of isocyanate reactive groups, of polyhydroxycarboxylic acid as a hydrophilic agent and e) 0-15 equivalent %, in terms of isocyanate reactive groups, of at least one, in terms of isocyanate reactive groups, di- or polyfunctional component of a chain extender with molecular weight from 32 to 350 g/mol, where i) this takes place using (partially) water-miscible organic solvents which are inert to NCO-groups and have boiling point lower than 120°C (at 1013 mbar), ii) and they are used in such an amount that the polyurethane prepolymer contained in the reaction solution after complete conversion ranges from 70 to 98 wt %. Further, II) the polyurethane prepolymer solution obtained at step (I) is dispersed in water, where before, during or after dispersion, deprotonation of carboxylic acid groups with a base takes place at least partially, and then III) if needed, the contained organic solvent is completely removed during dispersion via distillation.

EFFECT: obtaining polyurethane dispersions which are stable during storage, endow said products of their application with good optical properties, high resistance to chemical reagents and pendulum hardness.

13 cl, 10 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: adhesive composition contains perchlorovinyl resin and an organic solvent. The composition contains dichloroethane as an organic solvent, as well as dibutyl phthalate and a modifier in form of epoxy diane resin ED-20 and N-nitrosodiphenylamine, with the following ratio of components in pts.wt: perchlorovinyl resin 20, organic solvent 80.0, dibutyl phthalate 1.0, epoxy diane resin ED-20 10.0-15.0, N-nitrosodiphenylamine 0.33-1.11.

EFFECT: invention increases strength when gluing together vulcanised rubber.

2 tbl

FIELD: chemistry.

SUBSTANCE: adhesive composition contains polychloroprene rubber nairit DP, butyl phenol formaldehyde resin 101 K, water, zinc oxide, magnesium oxide and an organic solvent which is a mixture of ethyl acetate and nefras. The composition additionally contains a modifier obtained first as a result of room temperature-reaction of an aliphatic amine - triethanolamine or polyethylene polyamine and silica filler Rosil R-175, with the following ratio of components, wt %: polychloroprene rubber nairit DP - 90.0, butyl phenol formaldehyde resin 101K - 90.0, water - 3.0, zinc oxide - 5.0, magnesium oxide - 11.0, organic solvent - 800.0, aliphatic amine - 0.1-0.2, silica filler Rosil R-175 - 10.0.

EFFECT: invention increases strength when gluing together vulcanised rubber.

2 tbl

FIELD: medicine.

SUBSTANCE: invention relates to medicine. Described is medication in form of plaster, which has glue layer, at least, on one surface of bottom layer, in which glue layer contains glue, badly soluble medication, first organic liquid component, second organic liquid component, third organic liquid component and linked polyvinylpyrrolidone. Solubility of badly soluble medication in first organic liquid component is not less than solubility of badly soluble medication in second organic liquid component, and solubility of badly soluble medication in second organic liquid component is not less, than solubility of badly soluble medication in third organic liquid component.

EFFECT: medicine in form of plaster has small area and ensures adhesion during long time.

4 cl, 1 dwg, 10 ex

FIELD: medicine.

SUBSTANCE: invention refers to medicine. What is described is a biodegradable plaster containing at least one bioadhesive layer, and at least one non-bioadhesive layer with the bioadhesive layer containing at least one polyarphon dispersion, and at least one bioadhesive polymer with the polyarphon dispersion containing at least one pharmacologically active substance.

EFFECT: biodegradable plaster can deliver drugs, including poorly water soluble ones.

21 cl, 8 ex

FIELD: medicine.

SUBSTANCE: invention refers to medicine. What is described is a therapeutic plaster for local application of natural drugs applicable for oral administration and/or for injection, containing the following components: - a pillow made of a bearing material, at least for one natural drug either fluid, or introduced in a solution, a coating completely covering the pillow and projecting at least from two sides with a skin-adhesive layer, and at least one natural drug either fluid, or introduced in a solution either in the bearing material, or in a reservoir opening to the bearing material, and is used for stimulating or treating, particularly, in trigger and acupuncture points, as well as for meridian therapy.

EFFECT: substances inactive or low-effective percutaneously if applied in certain skin regions, particularly for a long period of time, can exhibit previously unused action ensured by slow release from the bearing material.

10 cl, 4 dwg

FIELD: medicine.

SUBSTANCE: invention refers to medicine. What is described is a therapeutic system for introduction of a pharmaceutically active substance, nonvolatile at least at room temperature, with a daily dose max. 30 mg, comprising a skin non-contact and active substance impenetrable external layer, an adjacent skin distant polymeric layer of polyisobutylene of the coating weight at least 80 g/m2, an adjoining skin contact adhesive polymeric layer of acrylate copolymers of the coating weight max. 50 g/m2, and also an active substance impenetrable protective layer (easily) removed from the skin contact layer.

EFFECT: transdermal therapeutic system has a high level of using the active ingredient and a higher dose accuracy.

18 cl, 2 ex

FIELD: medicine.

SUBSTANCE: invention refers to medicine, namely oncology, and can be used for treating cervical cancer. That is ensured by radiation teletherapy and brachytherapy. Each brachytherapy session is preceded by bringing the Hydrogel Coletex-M Tissue 3-5 ml to the tumour before 12-18 hours. Before gel contact, the Coletex-M Tissue is introduced. Further,1-1,5 hours prior to the brachytherapy session, the textile tissue is removed, and Hydrogel Coletex-ADL Tissue 4-6 ml is brought to the tumour. Preliminary, the Hydrogel Coletex-ADL Tissue is added with lidocaine to achieve the gel concentration 4-6%.

EFFECT: method provides reduced total toxicity and drug load ensured by the required concentration of metronidazole maintained in the tumour before the radiation session, and also analgesia without using narcotic preparations, optimised time and geometry of centring introduction that allows intensifying the damage exposure on the tumour.

2 ex

Corn plaster // 2454249

FIELD: medicine.

SUBSTANCE: invention refers to medical and chemical-pharmaceutical industry and is applicable in healthcare facilities and domiciliary for external application as a remedy in skin diseases: corns, plantar callosities, callules. A corn plaster contains salicylic acid, precipitated sulphur, anhydrous lanolin, pine rosin, lump rubber, dimethylsulphoxide, pine resion, petrolatum and agidol with salicylic acid used as micronised particles sized max. 30 mcm, and the ingredients taken in certain proportions. The experimental clinical findings have shown that the leukocytic mass applied on corns has an effect on adjoining skin areas causing no allergy, irritation or redness if the plaster is applied on healthy skin.

EFFECT: corn plaster improves keratolytic, antiseptic and antimycotic properties ensured by qualitative and quantitative composition of the ingredients.

FIELD: medicine.

SUBSTANCE: invention refers to medicine. What is described is a haemostatic device for blood coagulation improvement which contains a gauze base, a clay material located thereon, and also polyol, such as glycerol or similar placed on the gauze base for binding the clay material. The device for bleeding wound management comprises at least a portion of the clay material contacting to blood flowing from the wound to cause coagulation. A dressing applicable on the bleeding wound for blood coagulation improvement comprises a flexible base and a gauze base located thereon. The gauze base comprises the clay material and polyol. Ahaemostatic sponge also contains a gauze basis and a disperse system of the haemostatic material and polyol on the first base surface. The invention also refers to N-substituted monomers and polymers, methods for producing such monomers and polymers and to methods for using for various medical purposes, e.g. in medical devices. In the preferential versions, a medical device represents a stent.

EFFECT: haemostatic device improves blood coagulation.

43 cl, 1 tbl, 9 dwg, 2 ex

FIELD: medicine.

SUBSTANCE: invention refers to medicine. There are described Transdermal Therapeutic Systems having a silicone adhesive layer, and a method for producing and using them.

EFFECT: transdermal therapeutic systems provide achieving a certain plasma concentration.

23 cl, 3 tbl, 4 dwg, 1 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to medicine and pharmaceutical industry, namely to composition for transcutaneous delivery of medication, which is realised from mixture, which contains: therapeutically efficient amount of medication, including initial medication and promedicine, as well as pharmaceutically acceptable carrier, both initial medication and promedicine being present in amount sufficient for manifestation of pharmacologic activity.

EFFECT: in preferable version of invention implementation mixture includes therapeutically efficient amount of pharmaceutically active agent, which contains ACE inhibitor, such as ramipril, promedicine being promedicine of ACE inhibitor, such as ethyl ester of ramipril and/or methyl ester of ramipril.

5 cl, 10 ex, 9 dwg

FIELD: medicine.

SUBSTANCE: invention refers to medicine. What is disclosed is a dosage form containing a base and a self-adhesive layer which contains a medicinal agent and covers at least one of the base sides; wherein the base consists of a polyester film of the thickness of 0.5 to 6.0 mcm, and a polyester non-woven material directly coupled with the film. The base is coated with the self-adhesive layer either directly or through an intermediate layer from the non-woven material.

EFFECT: adhesive preparation have sufficient elasticity for the purpose of tracking of the skin shape, as well as shows low ability to irritate the skin and high stability.

7 cl, 5 tbl, 7 ex

FIELD: medicine.

SUBSTANCE: material has two layers - the first one and the second one. The first one has staple viscose fibers. The second one is manufactured from staple easily fusible thermoplastic synthetic fibers. Both layers are joined to each other under water jet treatment. The second layer fibers partially penetrate into the first layer and fixed therein. The second layer surface is melted and turned outward. It becomes smooth under temperature and pressure treatment. The non-woven material has high absorbing capacity.

EFFECT: low risk of traumatic complications.

5 cl, 2 dwg

Up!