AU2014240240B2 - Adhesive composition for soft tissue, adhesive composition for covering wounds, or wound covering agent composition - Google Patents

Abstract

Disclosed is an adhesive composition for a soft tissue, an adhesive composition for covering a wound, or a wound covering agent composition which comprises (A) a monomer, (B) a polymer and (C) a polymerization initiator composition containing an organic boron compound and is characterized in that a mixture of the components (A), (B) and (C) has a viscosity ranging from 0.4 to 75,000 cp within 30 seconds after the components are mixed together. The composition has low toxicity, low hazardousness, high adhesion properties, and excellent workability upon application, and enables the production of a film having excellent properties. SF-2299 Drawings (Fig. 1] 1 i +-1 2 +- 1 3 %%89% MftMM& -1 1 Fig.2] ~- 22 +- 23 +- 2 3 +- 22

Description

H:\sxn\ntenvoen\NRPortbl\DCC\SXN\6843589_.docx-1/10/2014 ADHESIVE COMPOSITION FOR SOFT TISSUES, ADHESIVE COMPOSITION FOR WOUND DRESSING OR WOUND DRESSING COMPOSITION This is a divisional of Australian Patent Application No. 2010320137, the entire contents of which are incorporated herein by reference. Technical Field [0001] The present invention relates to an adhesive composition for soft tissues, an adhesive composition for wound dressing or a wound dressing composition. Background Art [0002] As soft tissue adhesives, adhesives for wound dressing or wound dressings, various compositions, e.g., compositions containing cyanoacrylate and compositions using materials derived from organisms, such as compositions containing fibrin and compositions containing albumin, have been studied in the past (see, for example, patent literature 1 and patent literature 2). [0003] The compositions containing cyanoacrylate are excellent in view of high adhesive strength, but they have poor biocompatibility, and there is a serious problem that formaldehyde generated by hydrolysis of cured products of the compositions exhibits high toxicity to organisms and inhibits healing. Particularly in parts that come into direct contact with central nervous system, blood vessels, etc., these compositions cannot be used. Moreover, since the curing time is extremely short, they are sometimes difficult to SF-2299 2 use. [0004] The compositions containing materials derived from organisms are excellent in that the biocompatibility is high and healing is rarely inhibited, but they have low adhesive strength. 5 Further, when the composition containing fibrin is used as an adhesive or the like, there is a side view that fibrin glue contained in the composition becomes a culture medium for bacteria, so that there is the risk of infection after operation or treatment and there is a fear of harmfulness. 10 (0005] When an adhesive is used for a wound of the skin or a soft tissue, or when a wound dressing is used for a wound, it is a usual way that the components are mixed in advance in a container or the like to prepare a composition and then the composition is applied to the surface of the soft tissue, the wound dressing part or the 15 like, taking into consideration workability, prevention of infection, etc. However, the state of the composition after mixing sometimes has influence on the workability during the application of the composition, that is, for example, if the viscosity of the composition is too high, the composition is hard to apply, or if the viscosity 20 is too low, the composition runs out of the necessary area. Moreover, if properties, such as elasticity and tensile elongation, of a film obtained by polymerization and solidification of the adhesive or the wound dressing are not proper, there sometimes occurs a problem that the film peels off from the skin after application because the skin 3 or the soft tissue is a flexible adherend. [00O6] Since acrylic adhesives using an initiator containing an organoboron compound have low toxicity and low harmfulness and have high adhesive strength, development of them to dental applications has been promoted (see, for example, patent literature 3) . However, if other medical applications, such as surgical applications, soft tissue adhesion applications and wound dressing applications, are intended, further improvement in handling stability or workability of the composition between mixing of the components and application to the application area has been sometimes required. Citation List Patent Literature [0007] Patent literature 1: Japanese Patent Laid-Open Publication No. 061658/2007 Patent Literature 2: Japanese Patent Laid-Open Publication No. 051121/2006 Patent literature 3: Japanese Patent Laid-Open Publication No. 110913/1997 Summary of Invention [00081 The present invention seeks to provide 4 a composition which not only has low toxicity, low harmfulness and high adhesive strength but also is excellent in workability during application and is capable of forming a film having properties that are preferable for an adhesive for soft tissues, an adhesive for wound dressing or a wound dressing. [0009] in order to deal with the above problems, the present inventors have earnestly studied compositions which are preferable as adhesives for soft tissues, adhesives for wound dressing or wound dressings. As a result, they have found that the above problems may be solved by an adhesive composition or a wound dressing composition comprising a monomer, a polymer and a specific polymerization initiator composition and having a viscosity of a specific range after mixing of these components, and they have accomplished the present invention. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention means a composition of materials, with which wounds made in soft tissues, such as skins, muscles, internal organs and blood vessels of organisms, by operations, accidents, etc., i.e., disconnected tissues, are surface-covered to carry out adhesion of skins of the wounds or temporary dressing of the wounds. [0010] Accordingly, the present invention provides adhesive composition for soft tissues, an adhesive composition for wound dressing or a wound dressing composition, comprising a monomer (A), a polymer (B) and a polymerization initiator composition (C) containing an organoboron compound, with the amount of the polymer (B) being in the range of 33 to less than 68 parts by weight, based on the total amount of the monomer (A), the polymer (E) and the polymerization 5 initiator composition (C) being 100 parts by weight; and having a viscosity of 30 10 to 1,000,000 cp 60 seconds after mixing of the components (A), (B) and (C), wherein the polymer (B) is a polymer mixture comprising polymer particles (bi) having a weight-average molecular weight of 30x104 to 60x10 4 and a specific surface area of 1.5 to 4.5 (mW/g), polymer particles (b2) having a weight-average molecular weight of 5x104 to 20x10 4 and a specific surface area of 0.51 to 1.2 (m 2 /g) and polymer particles (b3) having a weight-average molecular weight of 5x10 4 to 20x10 4 and a specific surface area of 0. to 0. 5 (m 2 /g) ; said polymer mixture comprising the polymer particles (bJ) in an amount of 0 to less than 10% by weight based on the total weight of the polymer particles (bli) , (b2) and (b3), and the polymer particles (b2) and the polymer particles (b3) in a total amount of more than 90 to 100% by weight based on the total weight of the polymer particles (bl), (b2) and (b3). [0011] Also described is polymer (B) being a polymer mixture which comprises polymer particles (bI) having a weight-average molecular weight of 30x10 4 to 60x10 4 and a specific surface area of 1.5 to 4.5 (m 2 /g), polymer particles (b2) having a weight-average molecular weight of 5x10 4 to 20x10 4 and a specific surface area. of 0.51 to 1.2 (m 2 /g) and polymer particles (b3) having a weight-average molecular weight of 5x10 4 to 20x10 4 and a specific surface area of 0.1 to 0,5 (m?/g) , contains the polymer particles (bl) in an amount of 0 to 98% by weight, and contains the polymer particles (b2) and the polymer particles (b3) in the total amount of not less than 2% by weight based on the total weight of the polymer particles (bl), (b2) and (b3), with the proviso that the total amount of the polymer particles (bl), (b2) and (b3) is 100% by weight.

5A [0012j A film, which is obtained from the above adhesive composition or wound dressing composition, is given 24 hours after the preparation of the composition and has a thickness of not less than 0.1 pm, a length of not less than 25 mm and a width of not less than 2 mm, preferably has a flexural elastic modulus, as measured under the conditions of a test rate of 2 mm/min, of not more than 750 MPa and a tensile elongation, as measured under the conditions SF-2299 6 of a test rate of 1 mm/min, of not less than 5%. [0013] The adhesive composition or the wound dressing composition may further comprise, for example, a polymerization inhibitor (D), an ultraviolet light absorber, and a plasticizer. 5 [0014] In a preferred embodiment, the content of the polymerization inhibitor (D) in the composition is in the range of 10 to 5000 ppm based on the monomer (A). [0015] The polymerization inhibitor (D) is preferably at least one substance selected from hydroquinone, 10 dibutylhydroquinone, hydroquinone monomethyl ether, 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-p-cresol, catechol, pyrogallol, benzoquinone, 2-hydroxybenzoquinone, p-methoxyphenol, t-butylcatechol, butylated hydroxyanisole, butylatedhydroxytoluene and t-butylhydroquinone. 15 [0016] The adhesive composition or the wound dressing composition may further comprise at least one substance selected from: anti-infectious agents, antibiotics, antibacterial agents, anti-virus agents, analgesics, compositions of analgesics, anorectic drugs, antihelmintic drugs, antiarthritic agents, antiasthmatic 20 drugs, anticonvulsants, antidepressants, antidiuretics, antidiarrheal agents, antihistamine drugs, anti-inflammatory drugs, antimigraine drugs, antiemetic agents, antineoplastic drugs, antiparkinsonian agents, antipruritic drugs, antipsychotics, antipyretic drugs, antispasmodic drugs, anticholinergic agents, SF-2299 7 sympathomimetic agents, cardiovascular drugs, antiarrhythmic drugs, antihypertensive drugs, diuretics, vasodilators, immunosuppressant drugs, muscle-relaxant drugs, parasympatholytic drugs, stimulants, sedative drugs, tranquilizers, cholinergic agents, chemotherapeutic 5 drugs, radio pharmaceuticals, bone inductive drugs, heparin neutralizer agents of static bladder, procoagulants, hemostatic agents, xanthine derivatives, hormones, proteins of natural origin or proteins synthesized by genetic engineering, polysaccharides, glycoproteins, lipoproteins, oligonucleotides, antibody, antigen, 10 vasopressin, vasopressin analogs, epinephrine, selectin, clot promoting toxicants, plasminogen activating factor inhibitors, platelet activators, synthetic peptides having hemostatic action, and perfumes, such as orange oil, grapefruit oil, lemon oil, lime 15 oil, clove oil, wintergreen oil, peppermint oil, peppermint spirit, banana distillate, cucumber distillate, honey distillate, rose water, menthol, anethole, alkyl salicylate, benzaldehyde, monosodium glutamate, ethylvanillin, thymol and vanillin. [0017] The kit of thepresent inventionusedas an adhesive 20 for soft tissues, an adhesive for wound dressing or a wound dressing has members in which the components of the monomer (A), the polymer (B) and the polymerization initiator composition (C) containing an organoboron compound, which are contained in the adhesive composition or the wound dressing composition, are encased in two or more divided SF-2299 8 groups in an optional combination. [0018] The above kit preferably has constitution in which the monomer (A), the polymer (B) and the polymerization initiator composition (C) are each independently encased, and the monomer (A) 5 is first mixed with the polymerization initiator composition (C) containing an organoboron compound and subsequently mixed with the polymer (B). [0019) When the above kit contains the polymerization inhibitor (D), the kit has members in which the components of the 10 monomer (A), the (meth)acrylate polymer (B), the polymerization initiator composition (C) containing an organoboron compound and the polymerization inhibitor (D), which are contained in the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition, are encased in two or 15 more divided groups in an optional combination. [0020] The kit containing the polymerization inhibitor preferably has constitution in which a mixture of the monomer (A) and the polymerization inhibitor (D), the polymer (B) and the polymerization initiator composition (C) are each independently 20 encased, and the mixture of the monomer (A) and the polymerization inhibitor (D) is first mixed with the polymerization initiator composition (C) containing an organoboron compound and subsequently mixed with the polymer (B). [0021] In the kit, a jig that is used for applying a SF-2299 9 composition obtained by mixing adhesive components or wound dressing components containing the components (A) , (B) and (C) and the components added when needed may be further included. [0022] The jig is, for example, a brush, a fiber ball, 5 a cloth, a sponge ball or a piece of sponge. [0023] In the above kit, an aqueous solution for adhesion pretreatment containing 1 to 15% by weight of citric acid and 1 to 5% by weight of iron(III) chloride may be further contained. 10 Advantageous Effects of Invention [0024) The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention not only has low toxicity, low harmfulness and high adhesive strength but also is excellent in 15 workability during application and is capable of forming a film having properties that are preferable for an adhesive for soft tissues, an adhesive for wound dressing or a wound dressing. When the composition is applied to a wound, the wound can be strongly bonded with the adhesive. Especially when the composition of the invention is applied to a wound 20 of the outer skin, the wound of the outer skin can be joined with the adhesive, and after healing, the adhesive can be naturally separated from the outer skin. Brief Description of Drawings SF-2299 10 (00251 Fig. 1 is a schematic view showing an example of a process for preparing a sample film used in the examples of the present invention. Fig. 2 is a schematic view showing an example of a process for 5 preparing -an evaluation sample for evaluating adhesive strength in Examples 14A to 17A of the present invention. Fig. 3 is a schematic view showing an example of a process for preparing an evaluation sample for evaluating adhesive strength in Examples 1C, 3C, 4C and 17C of the present invention. 10 Description of Embodiments [0026] In the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention, a monomer (A) is contained. 15 As the monomer (A) , any monomer can be used without speci fic restriction as long as it can be polymerized by the later-described polymerization initiator composition (C) . As the monomer (A), any of a monofunctional monomer and a polyfunctional monomer can be used depending upon the use purpose. 20 [0027] Examples of themonomers (A) includemethacrylates, acrylates and other vinyl compounds. Of such monomers, acrylates and methacrylates are preferable from the viewpoint of relatively low irritation of the human body. Hereinafter, (meth)acrylates may be used to refer to acrylates and SF-2299 11 methacrylates. [00283 Of the monomers, monomers having an acidic group are preferable from the viewpoint of excellent adhesion properties. [0029] Therefore, use of a combination of a (meth) acrylate 5 (having no acidic group) and a monomer having an acidic group as the monomer (A) is also a preferred embodiment. [0030] Examples of monofunctional (meth)acrylates (having no acidic group) include: alkyl (meth)acrylates, such as methyl (meth)acrylate, ethyl 10 (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate and isobornyl (meth)acrylate; hydroxyalkyl esters of (meth)acrylic acid, such as 15 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 1, 2-dihydroxypropyl mono (meth) acrylate, 1, 3-dihydroxypropyl mono(meth)acrylate and erythritol mono(meth)acrylate; 20 polyalkylene glycol mono(meth)acrylates, such as diethylene glycol mono(meth)acrylate, triethylene glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate and polypropylene glycol mono (meth) acrylate; (poly)alkylene glycol monoalkyl ether (meth)acrylates, such SF-2299 12 as ethylene glycol monomethyl ether (meth) acrylate, ethylene glycol monoethyl ether (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, triethylene glycol monomethyl ether (meth) acrylate, polyethylene glycol monomethyl ether (meth)acrylate and 5 polypropylene glycol monoalkyl ether (meth)acrylate; fluoroalkyl esters of (meth)acrylic acid, such as perfluorooctyl (meth)acrylate and hexafluorobutyl (meth)acrylate; silane compounds having a (meth)acryloxyalkyl group, such as y- (meth) acryloxypropyltrimethoxysilane and 10 y- (meth) acryloxypropyltri (trimethylsiloxy) silane; and (meth)acrylates having a heterocyclic ring, such as tetrahydrofurfuryl (meth)acrylate. [0031) Examples of the polyfunctional (meth)acrylates (having no acidic group) include: 15 poly (meth) acrylates of alkanepolyols, such as ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butyleneglycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hexylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate and pentaerythritol tetra(meth)acrylate; 20 polyoxyalkane polyol poly(meth)acrylates, such as diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, dibutylene glycol di (meth) acrylate and dipentaerythritol hexa (meth) acrylate; SF-2299 13 alicyclic or aromatic di(meth)acrylates represented by the following formula (1): (00321

CH

2 CH 2

C-C-O-(CH

2

CH

2 0)j-R'-(OCH 2

CH

2 )n-O-C-C 1 I II I RO OR (1) 5 [0033] wherein R is a hydrogen atom or a methyl group, m and n are numbers of 0 to 10 which may be the same or different, and R1 is any one of the following: [0034] Q CH 2 Q CH2H

CH

3 CH 3

CH

3

CH

3 QS QD H S H SF-2299 14 (0035] alicyclic or aromatic epoxy di(meth)acrylates represented by the following formula (2): [0036]

CH

2 H HH H HH H H H CH 2 11 I I I I I I II - I I 11 C-- -C-C-C-0-R -0-C-C-C- 0-R -- C-C-C O- -C R O HOH HOH HOH OR I I I H H H (2) 5 [0037) wherein R is a hydrogen atom or a methyl group, n is a number of 0 to 10, and R' is any one of the following: [0038)

CH

2 0 H CH 2 H CH3

CH

3 H C H

CH

3 CH3 Q 0 ,H 0 H QsQH S H SF-2299 15 [0039] and polyfunctional (meth)acrylates having a urethane bond in a molecule, which are represented by the following formula (3): [0040]

CH

2 CH 2

C-C-O-CH

2

CH

2 -O-C-N--R2-N-C-0-CH 2

CH

2 -0-C-C I Il I1 I | || || 5 RO O H HO O R (3) [0041] wherein R is a hydrogen atom or a methyl group, and R 2 is any one of the following: [0042]

H

3 C

CH

3

CH

3

H

3 C C H 3

CH

3 I CH2 -Lr-CH 2 - -CH 2 -C- CH 2

-CH

2 CH 3 H

CH

3

CH

3 CH3 CH3 10 [0043] [0044] Of these (meth)acrylates, preferred monofunctional (meth)acrylates include: SF-2299 16 alkyl (meth) acrylates, such as methyl (meth) acrylate and ethyl (meth)acrylate; hydroxyalkyl esters of (meth)acrylic acid, such as 2-hydroxyethyl (meth) acrylate, 1, 3-dihydroxypropyl 5 mono(meth)acrylate and erythritol mono (meth)acrylate; and polyethylene glycol mono (meth) acrylates, such as triethylene glycol monomethyl ether (meth)acrylate and triethylene glycol mono(meth)acrylate. [0045) Preferred polyfunctional (meth)acrylates 10 include: di (meth) acrylateshavinganethyleneglycolchaininamolecule, such as triethylene glycol di (meth) acrylate and polyethylene glycol di (meth) acrylate; compounds represented by the following formula (1)-a: 15 [0046]

CH

2

CH

3

CH

2 C-C-0-(CH 2

CH

2 0)i Q -(UO (OCH 2

CH

2 )n-O-C-C R O CH 3 0I (1)-a [0047] wherein R is a hydrogen atom or a methyl group, and m and n are numbers of 0 to 10 which may be the same or different; compounds represented by the following formula (2)-a: 20 [0048)

CH

2 H H H CH 3 H H H CH 2 C-C-O-c c-c-O O-c-c-c-O-c-c R O H O H CH 3 H O H O R H H (2)-a SF-2299 17 [0049) wherein R is a hydrogen atom or a methyl group; and compounds represented by the following formula (3)-a: [0050)

CH

2 CH3 CH CH 2 C-C-0-CH2CH2o-C-N--CH 2

-C-CH

2

-C-CH

2

-CH

2 -N-C-o-CH 2

CH

2 -o-C-C 5 O CH H H OK (3)-a [0051) wherein R is a hydrogen atom or a methyl group. [0052] These (meth)acrylates can be used singly or in combination of two or more kinds. [0053] Examples of the monomers having an acidic group 10 include: monomers having a carboxylic acid group or its anhydride group, such as (meth)acrylic acid and its anhydride, 1,4-di(meth)acryloxyethylpyromellitic acid, 6-(meth)acryloxyethylnaphthalene-1,2,6-tricarboxylic acid, 15 N- (meth) acryloyl-p-aminobenzoic acid, N- (meth) acryloyl-o-aminobenzoic acid, N- (meth) acryloyl-m-aminobenzoic acid, N-(meth)acryloyl-5-aminosalicylic acid, N-(meth)acryloyl-4-aminosalicylic acid, 20 4-(meth)acryloxyethyltrimellitic acid and its anhydride, 4-(meth)acryloxybutyltrimellitic acid and its anhydride, 4-(meth)acryloxyhexyltrimellitic acid and its anhydride, 4-(meth)acryloxydecyltrimellitic acid and its anhydride, SF-2299 18 2- (meth) acryloyloxybenzoic acid, 3- (meth) acryloyloxybenzoic acid, 4- (meth) acryloyloxybenzoic acid, P- (meth) acryloyloxyethyl hydrogensuccinate, p- (meth) acryloyloxyethyl hydrogenmaleate, 3- (meth) acryloyloxyethyl hydrogenphthalate, 5 11-(meth)acryloyloxy-1,1-undecanedicarboxylic acid, and p-vinylbenzoic acid; monomers having a phosphoric acid group, such as (2-(meth)acryloxyethyl)phosphoric acid, (2-(meth)acryloxyethylphenyl)phosphoric acid and 10 10- (meth) acryloxydecylphosphoric acid; and monomers having a sulfonic acid group, such as p-styrenesulfonic acid and 2-acrylamido-2-methylpropanesulfonic acid. [0054] Of these monomers having an acidic group, 4-methacryloxyethyltrimellitic acid and its anhydride are 15 preferable. (0055] These monomers having an acidic group can be used singly or in combination of two or more kinds. By the use of these monomers having an acidic group, the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound 20 dressing composition tends to have more improved adhesion properties. [00561 The monomer having an acidic group is preferably contained in an amount of 1 to 20 parts by weight, more preferably 1 to 10 parts by weight, still more preferably 1 to 8 parts by weight, based on 100 parts by weight of the total amount of the (meth) acrylate SF-2299 19 (having no acidic group) and the monomer having an acidic group. If the amount thereof is out of the above range, an evil influence is sometimes exerted on the adhesive strength or the biocompatibility. [0057) The amount of the monomer (A) is preferably in 5 the range of 10 to 98.95 parts by weight, more preferably 25 to 89.5 parts by weight, still more preferably 37 to 86 parts by weight, based on 100 parts by weight of the total amount of the monomer (A), the later-described polymer (B) and the later-described polymerization initiator composition (C). 10 [0058] If the amount of the monomer (A) is less than the lower limit of the above range, the viscosity is increased, and application tends to be difficult. If the amount of the monomer (A) exceeds the upper limit of the above range, the adhesive strength is poor, and there is a possibility that the mixture runs out of the 15 desired area to obstruct the treatment. [0059] In some cases, the amount of the monomer (A) is preferably in the range of 5 to 98.95 parts by weight, more preferably 17 to 98.5 parts by weight, still more preferably 20 to 85 parts by weight, particularly preferably 24 to 85 parts by weight, much more 20 preferably 24 to 48 parts by weight, based on 100 parts by weight of the total amount of the monomer (A), the later-described polymer (B) and the later-described polymerization initiator composition (C) . [0060] If the amount of the monomer (A) is less than the lower limit of the above range, the viscosity is increased, and SF-2299 20 operations such as application tend to become dif ficult. Iftheamount of the monomer (A) exceeds the upper limit of the above range, adhesive strength and other properties, such as flexural elastic modulus, tensile strength and flexural strength, tend to become poor. Moreover, 5 there is a possibility that the mixture runs out of the desired area to obstruct the treatment. [0061] In the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention, a polymer (B) is further 10 contained. [00621 Examples of the polymers (B) include methacrylate polymers, acrylate polymers, styrene-based elastomers, vinyl chloride-based elastomers, olefin-based elastomers, polyester-based elastomers, polyamide-based elastomers, urethane-based elastomers, 15 an ethylene/vinyl acetate copolymer and a silicon polymer. These polymers can be used singly or in combination of two or more kinds. [00631 Of these polymers (B) , preferable are methacrylate polymers and acrylate polymers from the viewpoint of homogeneity in the mixing process. The methacrylate polymers and the acrylate 20 polymers are sometimes generically referred to as "(meth)acrylate polymers" hereinafter. [0064] Examples of the (meth) acrylate polymers include: uncrosslinked polymers, such as polymethyl (meth)acrylate, polyethyl (meth) acrylate, a methyl (meth) acrylate/ethyl SF-2299 21 (meth)acrylate copolymer, a methyl (meth)acrylate/butyl (meth)acrylate copolymer and a methyl (meth)acrylate/styrene copolymer: and crosslinked polymers, such as a methyl (meth) acrylate/ethylene 5 glycol di(meth)acrylate copolymer, a methyl (meth) acrylate/triethylene glycol di (meth) acrylate copolymer and a copolymer of methyl (meth) acrylate and a butadiene-based monomer. [0065] When the rubbers, such as natural rubbers and synthetic rubbers, and the elastomers, such as thermoplastic 10 elastomers, among the above polymers are used by mixing them with the (meth)acrylate polymer, they function as flexibilizers and can enhance flexibility of the composition. Examples of the synthetic rubbers include EPT (ethylene/propylene/terpolymer) . Examples of the thermoplastic elastomers include styrene-based elastomers, vinyl 15 chloride-basedelastomers, olefin-based elastomers, polyester-based elastomers, polyamide-based elastomers, urethane-based elastomers, an ethylene/vinyl acetate copolymer and a silicon polymer. [0066] The molecular weight of the above elastomer is usuallyintherangeof 1,000 tol,000, 000, preferably2,000 to500, 000. 20 The glass transition point (Tg) of the elastomer is usually not higher than 20 0 C, preferably not higher than 0*C. [0067] In the (meth)acrylate polymers, organic or inorganic composites in which metal oxides or metal salts are coated with above-mentioned uncrosslinked polymers or crosslinked polymers SF-2299 22 are further included. [0068] The weight-average molecular weight of the polymer, typically, the (meth) acrylate polymer, is preferably in the range of 1,000 to 1,000,000, more preferably 50,000 to 500,000, still more 5 preferably 100,000 to 500,000. The above molecular weight is a molecular weight in terms of standard polymethyl methacrylate, as determined by gel permeation chromatography (GPC). [0069] Thepolymer (B) maybe composedof polymer particles. When the polymer (B) is composed of polymer particles, they may be 10 polymer particles of plural kinds. [0070] Examples of such polymer particles include polymer particles (bl) having a weight-average molecular weight of 30x10 4 to 60x104 and a specific surface area of 1.5 to 4.5 (m 2 /g), polymer particles (b2) having a weight-average molecular weight of 5x104 to 15 20x104 and a specific surface area of 0.51 to 1.2 (m 2 /g), and polymer particles (b3) having a weight-average molecular weight of 5x104 to 20x104 and a specific surface area of 0.1 to 0.5 (m 2 /g) [0071] The specific surface area of the polymer particles (bl) is preferably in the range of 1.5 to 4.5 (m 2 /g), more preferably 20 2.0 to 4.0 (m 2 /g). [0072] The specific surface area of the polymer particles (b2) is preferably in the range of 0.51 to 1.2 (m 2 /g), more preferably 0.6 to 1.0 (m 2 /g). [0073] The specific surface area of the polymer particles SF-2299 23 (b3) is preferably in the range of 0.1 to 0.5 (m 2 /g), more preferably 0.2 to 0.45 (m 2 /g). [0074] The volume mean particle diameter of the polymer particles (bl) is usually in the range of 1 to 50 (pm), preferably 5 5to40 (pm) . The volume mean particle diameter of the polymer particles (b2) is usually in the range of 0.1 to 40 (pm), preferably 1 to 20 (pm) . The volume mean particle diameter of the polymer particles (b3) is usually in the range of 1 to 50 (pm), preferably 5 to 40 (pm) . [0075] When the polymer (B) is a polymer mixture composed 10 of the polymer particles (b2) and the polymer particles (b3), and if necessary, the polymer particles (b1), the total amount of the polymer particles (b2) and the polymer particles (b3) is preferably not less than 2% by weight, more preferably not less than 5% by weight, based on the total weight of the polymer (bl), the polymer (b2) and 15 the polymer (b3). The polymer mixture is sometimes composed of the polymer particles (b2) and the polymer particles (b3) in the total amount of 100% by weight. [0076) When the total amount of the polymer particles (b2) and the polymer particles (b3) is not less than the lower limit 20 of the above range, the polymer (B) is apt to be homogeneously dispersed in the monomer (A) and is more excellent in solubility in the monomer (A) . Moreover, application of the composition to a wound or a soft tissue is made easier, and spreading of the composition over the surf ace of a wound or a soft tissue after the application tends to become SF-2299 24 smaller. [0077] When the polymer (bl) is contained in the polymer particles, the total amount of the polymer (b2) and the polymer (b3) is preferably not more than 99% by weight, more preferably not more 5 than 95% by weight, still more preferably not more than 90% by weight, based on the total weight of the polymer (bl), the polymer (b2) and the polymer (b3). [0078] When the polymer (bl) is contained in the polymer particles, the content of the polymer (bl) is preferably not more 10 than 98% by weight, more preferably not more than 95% by weight, based on the total weight of the polymer (b1) , the polymer (b2) and the polymer (b3) . The content of the polymer (bl) is preferably not less than 1% by weight, more preferably not less than 5% by weight, still more preferably not less than 10% by weight, based on the total weight 15 of the polymer (bl), the polymer (b2) and the polymer (b3). [0079] The amount of the polymer (B) is preferably in the range of 1 to 70 parts by weight, more preferably 10 to 65 parts by weight, still more preferably 13 to 65 parts by weight, much more preferably 13 to 60 parts by weight, based on 100 parts by weight 20 of the total amount of the monomer (A), the polymer (B) and the polymerization initiator composition (C). [0080] If the amount of the polymer (B) is less than the lower limit of the above range, progress of polymerization becomes difficult, adhesion ef fect is poor, and besides, there is a possibility SF-2299 25 that the mixture runs out of the desired area to obstruct the treatment. If the amount of the polymer (B) exceeds the upper limit of the above range, mixing with the monomer (A) becomes difficult. Further, because of rapid increase of viscosity, extrusion of the mixture from 5 the container tends to become di f ficult. Furthermore, polymerization proceeds to immediately form a polymerization cured product in some cases, so that the composition tends to be not excellent in operability as an adhesive or a wound dressing. [0081] When the polymer (B) is a (meth) acrylate polymer, 10 the amount of the (meth) acrylate polymer is sometimes in the range of preferably 1 to 75 parts by weight, more preferably 1 to 73 parts by weight, still more preferably 10 to 73 parts by weight, much more preferably 15 to 73 parts by weight, particularly preferably 13 to 68 parts by weight, most preferably 21 to 64 parts by weight, based 15 on 100 parts by weight of the total amount of the monomer (A) , the (meth)acrylate polymer and the later-described polymerization initiator composition (C). [0082] If the amount of the (meth)acrylate polymer is less than the lower limit of the above range, adhesive strength and 20 other properties, such as flexural elastic modulus, tensile strength, compression strength and flexural strength, tend to become poor. If the amount of the (meth)acrylate polymer exceeds the upper limit of the above range, the viscosity is increased, and operations, such as application and injection, tend to become difficult.

SF-2299 26 (0083] When the polymer (B) is a (meth)acrylate polymer and is a mixture of the polymer particles (bl), (b2) and (b3), the following embodiments are preferable under the conditions that the total amount of the polymer particles (bl), (b2) and (b3) is 100% 5 by weight and the total amount of the polymer particles (b2) and (b3) is not less than 2% by weight, preferably not less than 5% by weight. (0084] When the amount of the polymer (B) is not less than 13 parts by weight but less than 28 parts by weight based on 100 parts by weight of the total amount of the monomer (A), the polymer 10 (B) and the polymerization initiator composition (C), the amount of the polymer particles (b1) is preferably in the range of 10% by weight to 95% by weight, more preferably 15% by weight to 95% by weight, still more preferably 38% by weight to 95% by weight, the amount of the polymer particles (b2) is preferably not more than 90% by weight, 15 more preferably not more than 85% by weight, still more preferably not more than 62% by weight, and the amount of the polymer particles (b3) is preferably not more than 90% by weight, more preferably not more than 85% by weight, still more preferably not more than 62% by weight; 20 when the amount of the polymer (B) is not less than 28 parts by weight but less than 68 parts by weight based on 100 parts by weight of the total amount of the monomer (A) , the polymer (B) and the polymerization initiator composition (C), the amount of the polymer particles (bIl) is preferably in the range of 10% by weight to 95% SF-2299 27 by weight, more preferably 10% by weight to 80% by weight, still more preferably 10% by weight to 60% by weight, the amount of the polymer particles (b2) is preferably not more than 90% by weight, and the amount of the polymer particles (b3) is preferably not more than 80% 5 by weight, more preferably not more than 75% by weight; and when the amount of the polymer (B) is not less than 33 parts by weight but less than 68 parts by weight based on 100 parts by weight of the total amount of the monomer (A), the polymer (B) and the polymerization initiator composition (C), the amount of the polymer 10 particles (b1) is preferably less than 10% by weight, more preferably not more than 8% by weight, still more preferably not more than 5% by weight, the amount of the polymer particles (b2) is preferably not more than 100% by weight, more preferably 20% by weight to 100% by weight, and the amount of the polymer particles (b3) is preferably 15 not more than 100% by weight, more preferably not more than 80% by weight. [0085) The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention is characterized by using the 20 later-described organoboron compound (cl) as the initiator composition (C) contained, and when the organoboron compound is added to a composition containing a monomer, polymerization reaction begins slowly in a relatively early stage and proceeds. This greatly differs from a case of using.a peroxide as a polymerization initiator where SF-2299 28 a relatively long time is required for the beginning of polymerization even if the polymerization initiator is added, and if the polymerization reaction once begins, the, reaction proceeds rapidly and is completed in a relatively short time. In order to prepare 5 a composition that is preferably used for wounds, soft tissues, etc., therefore, it is important to use such a polymer (B) of the present invention in such an amount as described above based on the monomer (A) . By the use of such a polymer (B), not only can workability be ensured over a long time but also fluidity and application properties 10 that are preferable in use for wounds, soft tissues, etc. can be ensured. [0086) The polymerization initiator composition (C) contained in the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention contains an oragnoboron compound (cl) as an 15 essential component, and can contain an aprotic solvent (c2) and an alcohol (c3), when needed. Since the polymerization initiator composition (C) containing the organoboron compound (cl) is contained in the composition of the present invention, a residue of the monomer (A) tends to be smaller when the whole composition is cured after 20 application of the composition to a wound, a soft tissue or the like, as compared with a composition using a peroxide as a polymerization initiator. Further, a part of it penetrates into the epithelium and begins to undergo polymerization. Hence, the composition of the present invention is favorably used for organisms.

SF-2299 29 [0087) Examples of the organoboron compounds (c1) include trialkylboron, alkoxyalkylboron, dialkylborane and partially oxidized trialkylboron. (0088] Examples of the trialkylborons include 5 trialkylborons having an alkyl group of 2 to 8 carbon atoms, such as triethylboron, tripropylboron, triisopropylboron, tributylboron, tri-sec-butylboron, triisobutylboron, tripentylboron, trihexylboron, triheptylboron, trioctylboron, tricyclopentylboron and tricyclohexylboron. The alkyl group maybe any of a straight-chain 10 alkyl group, a branched alkyl group and a cycloalkyl group, and three alkyl groups contained in the trialkylboron may be the same or different. [0089) The alkoxyalkylboron is, for example, monoalkoxydialkylboron or dialkoxymonoalkylboron. Specifically, 15 the alkoxyalkylboron is, for example, monoalkoxydialkylboron such as butoxybutylboron. The alkyl group of the alkoxyalkylboron may be the same as or different from the alkyl part of the alkoxy group. [0090] Examples of the dialkylboranes include dicyclohexylborane and diisoamylborane. Two alkyl groups of the 20 dialkylborane maybe the same or dif ferent. Two alkyl groups contained in the dialkylborane may be bonded to form a monocyclic structure or a bicyclo structure. Examples of such compounds include 9-borabicyclo (3.3.11 nonane. [0091] The partially oxidized trialkylboron is a SF-2299 30 partially oxidized product of the above trialkylboron. As the partially oxidized trialkylboron, partially oxidized tributylboron is preferable. As the partially oxidized trialkylboron, partially oxidized trialkylboron obtained by the addition of oxygen in an amount 5 of preferably 0.3 to 0.9 mol, more preferably 0.4 to 0.6 mol, based on 1 mol of the trialkylboron can be used. (0092) Of the above organoboron compounds, tributylboron or partially oxidized tributylboron is preferable, and partially oxidized tributylboron is more preferable. When tributylboron or 10 partially oxidized tributylboron is used as the organoboron compound (cl), not only is the operability of the composition improved but also the composition tends to have proper reactivity to organisms having moisture content. When tributylboron or partially oxidized tributylboron is used as the organoboron compound (cl), further, the 15 reaction is initiated and proceeds even in a place of high moisture content such as an organism, so that the monomer rarely remains on the interface between the adhesive or the wound dressing and an organism. Hence, the injurious properties to the organism are extremely little. Such organoboron compounds (c1) can be used singly or in combination 20 of two or more kinds. [0093] In the polymerization initiator composition (C), an aprotic solvent (c2) may be contained. Since the aprotic solvent is contained in the polymerization initiator composition (C) as above and the organoboron compound is diluted, exothermic properties of SF-2299 31 the organoboron compound (cl) having ignition properties become gentler to suppress ignition properties, and hence, handling of the composition during transportation, storage andmixing is facilitated. In the case where an extremely large amount of an adhesive or a wound 5 dressing is used, rapid generation of heat can be inhibited because of proper lowering of the exothermic properties, and consequently, damage of an organism that is in contact with the adhesive or the wound dressing of the present invention tends to be decreased. The boiling point of the aprotic solvent (c2) at 1 atm is usually in the 10 range of 30 0 C to 150 0 C, preferably 50 0 C to 120 0 C. If the boiling point is lower than the lower limit of the above range, the aprotic solvent is evaporated or scattered from the polymerization initiator composition during transportation or storage, and the ignition property suppressing effect of the organoboron compound (cl) tends 15 to be lowered. If the boiling point exceeds the upper limit of the above range, a residue of the aprotic solvent in a cured product formed from the adhesive composition or the wound dressing composition of the present invention is increased, and consequently, the adhesion performance of the composition tends to be lowered. 20 [0094] As the aprotic solvent (c2), a solvent that is unreactive to the organoboron compound (c1) and is capable of forming a homogeneous solution is preferable. (0095] Examples of the aprotic solvents (c2) include: hydrocarbons, such as pentane, hexane, cyclohexane, heptane, SF-2299 32 benzene and toluene; halogenated hydrocarbons, such as fluorobenzene, 1,1-dichloroethane, 1,2-dichloroethane and so-called flons; ethers, such as diethyl ether, diisopropyl ether, ethylene 5 glycol dimethyl ether and tetrahydrofuran; ketones, such as acetone, methyl ethyl ketone and diethyl ketone; and esters, such as methyl acetate, ethyl acetate and isopropyl acetate. 10 [0096] Of these, saturated aliphatic hydrocarbons, such as pentane, hexane and heptane, ethers and esters are preferable, and hexane, diisopropyl ether and ethyl acetate are more preferable. (0097] These aprotic solvents (c2) can be used singly or in combination of two or more kinds. 15 [0098] The content of the aprotic solvent (c2) in the polymerization initiator composition (C) is preferably in the range of30to80partsbyweightbasedon100partsbyweightoftheorganoboron compound (ci). [0099) If the content of the aprotic solvent (c2) is less 20 than the lower limit of the above range, satisfactory dilution effect is not obtained, and the effect to suppress generation of heat or ignition tends to be insufficient. On the other hand, if the content of the aprotic solvent (c2) exceeds the upper limit of the above range, polymerization initiation ability of the polymerization initiator SF-2299 33 composition (C) tends to become lower than needed. (0100] In the polymerization initiator composition (C), an alcohol (c3) may be further contained in addition to the aprotic solvent (c2) . By adding a small amount of the alcohol (c3) to the 5 polymerization initiator composition (C), the reaction by the oragnoboron compound (cl) is made still gentler without lowering the polymerization activity, and even if the composition is brought into contact with paper or the like in air, burning or ignition tends to be suppressed. 10 [0101] Examples of the alcohols (c3) include methanol, ethanol, n-propanol and its isomers, n-butanol and its isomers, n-pentanol and its isomers, n-hexanol and its isomers, and n-heptanol and its isomers. (0102] Of these alcohols (c3) , alcohols of 4 or less carbon 15 atoms, namely, methanol, ethanol, n-propanol and its isomers, and n-butanol and its isomers are preferable, and ethanol and n-propanol are more preferable. [0103] These alcohols (c3) can be used singly or in combination of two or more kinds. 20 [0104) The content of the alcohol (c3) in the polymerization initiator composition (C) is preferably in the range of 0.2 to 5 parts by weight, more preferably 0.3 to 4. 5 parts by weight, still more preferably 0.5 to 4 parts by weight, based on 100 parts by weight of the organoboron compound (bl).

SF-2299 34 [0105] If the content of the alcohol (c3) is less than the lower limit of the above range, satisfactory dilution effect is not obtained, and the effect to suppress generation of heat or ignition tends to be insufficient. On the other hand, if the content of the 5 alcohol (c3) exceeds the upper limit of the above range, polymerization initiation ability of the polymerization initiator composition (C) tends to become lower than needed. [0106] When the alcohol (c3) and the aprotic solvent (c2) are used in combination, the content of the aprotic solvent (c2) in 10 the polymerization initiator composition (C) is preferably in the range of 5 to 40 parts by weight, more preferably 10 to 30 parts by weight, still more preferably 10 to 25 parts by weight, based on 100 parts by weight of the organoboron compound (c1). [0107] If the content of the aprotic solvent (c2) is less 15 than the lower limit of the above range based on 100 parts by weight of the organoboron compound (cl), the effect to suppress generation of heat or ignition tends to be insufficient. On the other hand, if the content of the aprotic solvent (c2) exceeds the upper limit of the above range based on 100 parts by weight of the organoboron 20 compound (cl), polymerization initiation ability of the polymerization initiator composition (C) tends to be lowered. [0108] The amount of the polymerization initiator composition (C) is preferably in the range of 0.05 to 20 parts by weight, morepreferably0.5to 10 parts byweight, stillmore preferably SF-2299 35 1 to 3 parts by weight, based on 100 parts by weight of the total amount of the monomer (A), the polymer (B) and the polymerization initiator composition (C). [0109] If the amount of the polymerization initiator 5 composition (C) is less than the lower limit of the above range, progress of polymerization is difficult, and the adhesion effect tends to become poor. If the amount of the polymerization initiator composition (C) exceeds the upper limit of the above range, there is a possibility of lowering viscosity because of dilution or a possibility of exerting 10 evil influence on safety. Moreover, it is presumed that rapid polymerization proceeds to form a polymerization product immediately, and therefore, the composition tends to be not excellent in operability as an adhesive or a wound dressing. (0110] In the adhesive composition or the wound dressing 15 composition, other components may be further contained when needed, as long as they do not exert evil influence on the performance of the composition. [0111] As one of the other components, a polymerization inhibitor (D) can be mentioned. Examples of the polymerization 20 inhibitors (D) include hydroquinone compounds, such as hydroquinone and dibutylhydroquinone, hydroquinone monomethyl ether, phenols, such as 2,6-di-tert-butylphenol and 2,6-di-tert-butyl-p-cresol, catechol, pyrogallol, benzoquinone, 2-hydroxybenzoquinone, p-methoxyphenol, t-butylcatechol, butylated hydroxyanisole, SF-2299 36 butylated hydroxytoluene and t-butylhydroquinone. Of these, a mixture of hydroquinone monomethyl ether and 2,6-di-tert-butyl-p-cresol is preferably used. [0112] Of these polymerization inhibitors (D), 5 hydroquinone monomethyl ether is sometimes preferable from the viewpoint of good stability of the hydroquinone monomethyl ether itself. [0113] The above polymerization inhibitors (D) can be used singly or in combination of two or more kinds. 10 [0114] When the polymerization inhibitor (D) is added, the amount thereof is preferably in the range of 10 to 5000 ppm, more preferably 50 to 1000 ppm, still more preferably 50 to 500 ppm, based on the whole amount of the adhesive composition or the wound dressing composition. 15 (0115] It is also preferable to add the polymerization inhibitor (D) in an amount of 10 to 5000 ppm based on the monomer (A) . [0116] By preparing such a composition, for example, when an adhesive is applied to an adherend, such as the affected part 20 (affected part that is not dried because of exudate from the incised part) in the surgical operation, a wound or a soft tissue, the composition becomes more excellent in ensuring application properties and a proper curing time and can be more stably handled as an adhesive or a dressing than before. Moreover, the composition is excellent SF-2299 37 in workability. [0117] Although the .amount of the polymerization inhibitor (D) is as described above, the polymerization inhibitor (D) is more preferably added in an amount of 50 to 1000 ppm, still 5 more preferably 50 to 500 ppm, based on the monomer (A). By preparing such a composition, for example, the composition can be not only handled stablyduringapplicationbutalsocuredefficientlyafterapplication. If the content of the polymerization inhibitor (D) is less than the lower limit of the above range, curing takes place immediately after 10 mixing of the monomer (A), the polymer (B) and the polymerization initiator composition (C), and hence, application tends to become difficult. On the other hand, if the content of the polymerization inhibitor (D) exceeds the upper limit of the above range, polymerization initiation ability of the polymerization initiator 15 composition (C) is lowered, and the curing time becomes longer than needed. Hence, medical use of the composition tends to become difficult. [0118] As one of the other components, an ultraviolet light absorber can be further mentioned. Examples of the ultraviolet 20 light absorbers include: benzotriazole compounds, such as 2- (2' -hydroxy-5' -methylphenyl)benzotriazole, 2- (3', 5' -di-tert-butyl-2' -hydroxyphenyl)benzotriazole, 2- (5' -tert-butyl-2' -hydroxyphenyl)benzotriazole, SF-2299 38 2- (2' -hydroxy-5' - (1, 1, 3, 3-tetramethylbutyl) phenyl) benzotriazole, 2- (3' , 5' -di-tert-butyl-2' -hydroxyphenyl) -5-chlorobenzotriazole, 2- (3' -tert-butyl-2' -hydroxy-5' -methylphenyl) -5-chlorobenzotriazo le, 2- (3' -sec-butyl-5' -tert-butyl-2' -hydroxyphenyl) benzotriazole, 5 2-(2'-hydroxy-4'-octoxyphenyl)benzotriazole, 2- (3',5' -di-tert-amyl-2' -hydroxyphenyl) benzotriazole, 2- (3', 5' -bis (a, a-dimethylbenzyl) -2' -hydroxyphenyl) benzotriazole, 2- (3' -tert-butyl-2' -hydroxy-5' - (2-octyloxycarbonylethyl) phenyl) 5-chlorobenzotriazole, 10 2- (3' -tert-butyl-5' -[2- (2-ethylhexyloxy) carbonylethyl] -2' -hydrox yphenyl) -5-chlorobenzotriazole, 2- (3' -tert-butyl-2' -hydroxy-5' - (2-methoxycarbonylethyl) phenyl) -5 -chlorobenzotriazole, 2- (3' -tert-butyl-2'-hydroxy-5'- (2-methoxycarbonylethyl) phenyl) be 15 nzotriazole, 2- (3' -tert-butyl-2' -hydroxy-5'- (2-octyloxycarbonylethyl)phenyl) b enzotriazole, 2- (3' -tert-butyl-5'- [2- (2-ethylhexyloxy) carbonylethyl] -2' -hydrox yphenyl) benzotriazole, 20 2- (3' -dodecyl-2' -hydroxy-5' -methylphenyl) benzotriazole, a mixture of 2- (3' -tert-butyl-2'-hydroxy-5'- (2-isooctyloxycarbonylethyl)pheny 1)benzotriazole and 2,2' -methylene-bis [4- (1, 1,3, 3-tetramethylbutyl) -6-benzotriazol-2 SF-2299 39 -ylphenol), an ester interchange reaction product of 2- [3' -tert-butyl-5' - (2-methoxycarbonylethyl) -2' -hydroxyphenyl] be nzotriazole with polyethylene glycol 300, and [ [R-CH 2

CH

2

-COOCH

2

]

3

]

2 (wherein R is 5 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl); benzophenone compounds, such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 10 2-hydroxy-4-benzyloxybenzophenone, 2, 2' , 4, 4' -tetrahydroxybenzophenone, and 2,2'-dihydroxy-4,4'-dimethoxybenzophenone; 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, 15 bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl benzoate, and 20 3,5-di-tert-butyl-4-hydroxybenzyl benzoate; hindered amine compounds, such as bis(2,2,6,6-tetramethylpiperidyl)sebacate, bis (2,2,6, 6-tetramethylpiperidyl) succinate, bis(1,2,2,6,6-pentamethylpiperidyl)sebacate, SF-2299 40 bis(1,2,2,6,6-pentamethylpiperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, a condensation product of 1-hydroxyethyl-2, 2,6, 6-tetramethyl-4-hydroxypiperidine and succinic acid, a condensation product of 5 N,N' -bis (2,2,6, 6-tetramethyl-4-piperidyl) hexamethylenediamineand 4-tert-octylamino-2,6-dichloro-1,3,5-s-triazine, tris (2,2, 6, 6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6, 6-tetramethyl-4-piperidyl) -1,2,3, 4-butanetetraoat e, 1,1'-(1,2-ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 10 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1,2,2,6,6-pentamethyl-4-piperidyl)-2-n-butyl-2-(2-hydroxy-3, 5-di-tert-butylbenzyl)malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-d 15 ione, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, a condensation product of N,N' -bis (2,2, 6, 6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2, 6-dichloro-1, 3, 5-triazine, a condensation product of 20 2-chloro-4, 6-di- (4-n-butylamino-2,2,6, 6-tetramethylpiperidyl) -1, 3, 5-triazine and 1, 2-bis (3-aminopropylamino) ethane, a condensation product of 2-chloro-4, 6-di- (4-n-butylamino-1,2,2, 6, 6-pentamethylpiperidyl) 1,3,5-triazine and 1,2-bis(3-aminopropylamino) ethane, SF-2299 41 8-acetyl-3-dodecyl-7, 7, 9, 9-tetramethyl-1, 3, 8-triazaspiro [4.5] dec ane-2,4-dione, 3-dodecyl-1- (2,2, 6, 6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dio ne, and 5 3-dodecyl-1- (1, 2,2,6, 6-pentamethyl-4-piperidyl) pyrrolidine-2, 5-d ione; oxalamide compounds, such as 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butyloxanilide, 10 2,2' -didodecyloxy-5, 5' -di-tert-butyloxanilide, 2-ethoxy-2'-ethyloxanilide, N, N' -bis (3-dimethylaminopropyl) oxalamide, a mixture of 2-ethoxy-5-tert-butyl-2'-ethyloxanilide and 2-ethoxy-2' -ethyl-5, 4' -di-tert-butyloxanilide, a mixture of 15 o-methoxy- and p-methoxy-di-substituted oxanilides, and a mixture of o-ethoxy- and p-ethoxy-di-substituted oxanilides; 2- (2-hydroxyphenyl) -1,3, 5-triazine compounds, such as 2,4, 6-tris (2-hydroxy-4-octyloxyphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1,3,5 20 -triazine, 2- (2, 4-dihydroxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1, 3, 5-triazi ne, 2, 4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1, 3, 5-triazine, SF-2299 42 2- (2-hydroxy-4-octyloxyphenyl) -4, 6-bis (4-methylphenyl) -1, 3, 5-tri azine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4, 6-bis (2, 4-dimethylphenyl) -1, 3 ,5-triazine, 5 2- [2-hydroxy-4- (2-hydroxy-3-butyloxypropyloxy)phenyl] -4,6-bis (2, 4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4- (2-hydroxy-3-octyloxypropyloxy)phenyl]-4, 6-bis (2, 4-dimethylphenyl)-1,3,5-triazine, and 2- [4-dodecyl/tridecyloxy- (2-hydroxypropyl) oxy-2-hydroxyphenyl]-4 10 , 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine; and phosphite compounds or phosphonite compounds, such as triphenyl phosphite, diphenylalkyl phosphite, phenyldialkyl phosphite, tris (nonylphenylphosphite) , trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythrytyl diphosphite, 15 tris(2,4-di-tert-butylphenyl)phosphite, diisodecyl pentaerythrityl diphosphite, bis (2, 4-di-tert-butylphenyl) pentaerythrityl diphosphite, bis (2, 6-di-tert-butyl-4-methylphenyl) pentaerythrityl diphosphite, bisisodecyloxypentaerythrityl diphosphite, 20 bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythrityldiphosphite, bis (2,4, 6-tri-tert-butylphenyl)pentaerythrityl diphosphite, tristearyl sorbityl triphosphite, tetrakis (2, 4-di-tert-butylphenyl) -4,4' -biphenylene diphosphonite, 6-isooctyloxy-2, 4,8, 10-tetra-tert-butyl-12H-dibenzo[d.g]-1,3,2-d SF-2299 43 ioxaphosphocine, 6-fluoro-2, 4,8, 10-tetra-tert-butyl-12-methyldibenzo [d, g]l-1, 3,2-d ioxaphosphocine, bis (2, 4-di-tert-butyl-6-methylphenyl) methyl phosphite, and bis (2, 4-di-tert-butyl-6-methylphenyl) ethyl 5 phosphite. [0119] As the ultraviolet light absorber, abenzotriazole compound is preferable. [0120] When the ultraviolet light absorber is added, the amount thereof is preferably in the range of 10 to 1,000 ppm, more 10 preferably 100 to 800 ppm, based on the monomer (A) . By adding the ultraviolet light absorber as above, coloring of a liquid containing a monomer is suppressed, and storage stability of the monomer itself tends to be enhanced. [0121] As one of the other components, a plasticizer can 15 be further mentioned. [0122] Examples of the plasticizers include hydroxycarboxylic acid esters, such as citrate esters, isocitrate esters, tartrate esters, malate esters, lactate esters, glycerate esters and glycolate esters; trimethyl trimellitate esters, 20 diethylene glycol dibenzoate esters, diethyl malonate esters, triethyl o-acetylcitrate esters, benzyl butyl phthalate esters, dipropylene glycol dibenzoate esters, diethyl adipate esters, tributyl o-acetylcitrate esters, dimethyl sebacate esters, and alkylene glycol diesters.

SF-2299 44 [0123] Although the amount of the plasticizer is properly selected according to the type of the material, the plasticizer is used so that it may be usually contained in an amount of 0 to 30% by weight, preferably 0 to 20% by weight, more preferably 0 to 10% 5 by weight, in the whole adhesive composition or wound dressing composition. [0124] As one of the other components, a preservative can be further mentioned. [0125] Examples of the preservatives include: 10 methylparaben, methylparaben sodium, ethylparaben, propylparaben, propylbaraben sodium, butylparaben; cresol, chlorocresol; resorcinol, 4-n-hexylresorcinol, 3a, 4, 7, 7a-tetrahydro-2- ( (trichloromethyl) thio) -1H-isoindole-1, 3 15 2H)dione; benzalkonium chloride, benzalkonium sodium chloride, benzethonium chloride; benzoic acid, benzyl alcohol, cetylpyridinium chloride, chlorobutanol, dehydroacetic acid, o-phenylphenol, phenol, 20 phenylethyl alcohol, potassium benzoate, potassium sorbate, sodium benzoate, sodium dehydroacetate, sodium propionate, sorbic acid, thimerosal, thymol, phenylmercuric compounds, such as phenylmercuric borate, phenylmercuric nitrate and phenylmercuric acetate, and formaldehyde.

SF-2299 45 [0126] As examples of the other components, there can be further mentioned anti-infectious agents, antibiotics, antibacterial agents, anti-virus agents, analgesics, compositions of analgesics, anorectic drugs, antihelmintic drugs, antiarthritic 5 agents, antiasthmatic drugs, anticonvulsants, antidepressants, antidiuretics, antidiarrheal agents, antihistamine drugs, anti-inflammatory drugs, antimigraine drugs, antiemetic agents, antineoplastic drugs, antiparkinsonian agents, antipruritic drugs, antipsychotics, antipyretic drugs, antispasmodic drugs, 10 anticholinergic agents, sympathomimetic agents, cardiovascular drugs, antiarrhythmic drugs, antihypertensive drugs, diuretics, vasodilators, immunosuppressant drugs, muscle-relaxant drugs, parasympatholytic drugs, stimulants, sedative drugs, tranquilizers, cholinergic agents, chemotherapeutic drugs, radio pharmaceuticals, 15 bone inductive drugs, heparin neutralizer agents of static bladder, procoagulants, hemostatic agents, xanthine derivatives, hormones, proteins of natural origin or proteins synthesized by genetic engineering, polysaccharides, glycoproteins, lipoproteins, oligonucleotides, antibody, antigen, vasopressin, vasopressin 20 analogs, epinephrine, selectin, clot promoting toxicants, plasminogen activating factor inhibitors, platelet activators, and synthetic peptides having hemostatic action. Since these components are contained, the composition of the present invention can be used for the drug delivery system or the purpose of regenerative medicine.

SF-2299 46 [0127] Examples of the antibacterial agents include: element iodine, solid polyvinylpyrrolidone iodine, polyvinylpyrrolidone iodine; phenol compounds, such as tribromophenol, trichlorophenol, 5 tetrachlorophenol, nitrophenol, 3-methyl-4-chlorophenol, 3, 5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, 2,4-dichloro-3,5-dimethylphenol, 4-chlorothymol, chlorophene, triclosan, fenticlor, phenol, 10 2-methylphenol, 3-methylphenol, 4-methylphenol, 4-ethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 3,4-dimethylphenol, 2,6-dimethylphenol, 4-n-proylphenol, 4-n-butylphenol, 4-n-aminophenol, 4-tert-amylphenol, 4-n-hexylphenol, 4-n-heptylphenol, monoalkylhalophenol, polyalkylhalophenol, 15 aromatic halophenol, and ammonium salts, alkali metal salts and alkaline earth metal salts of these substances; silver nitrate, hexachlorophene, merbromin, tetracycline -HCl, tetracycline hydrate and erythromycin. [0128] In the adhesive composition or the wound dressing 20 composition, angiogeneric factor, basic fibloblast growth factor, epidermal growth factor, etc. may be contained as the above proteins for the purpose of accelerating tissue reparation. [0129] As examples of the other components, there can be further mentioned perfumes, such as orange oil, grapefruit oil, SF-2299 47 lemon oil, lime oil, clove oil, wintergreen oil, peppermint oil, peppermint spirit, banana distillate, cucumber distillate, honey distillate, rose water, menthol, anethole, alkyl salicylate, benzaldehyde, monosodium glutamate, ethylvanillin, thymol and 5 vanillin. [0130] Furthermore, an inorganic filler, an organic filler, an organic composite filler, a filler colorant, etc. may be contained as the other components. [0131] Examples of the inorganic fillers include: 10 metal oxide powders, such as zirconium oxide, bismuth oxide, titanium oxide, zinc oxide and aluminum oxide particles; metal salt powders, such as bismuth carbonate, zirconium phosphate and barium sulfate; glass fillers, such as silica glass, aluminum-containing glass, 15 barium-containing glass, strontium-containing glass and zirconium silicate glass; fillers having silver sustained-release property; and fillers having fluorine sustained-release property. [0132] From the viewpoint of formation of strong bonding 20 between an inorganic filler and the monomer (A) after curing, it is preferable to use an inorganic filler having been subjected to surface treatment such as silane treatment or polymer coating. [0133] These inorganic fillers can be used singly or in combination of two or more kinds.

48 [01341 As examples of the other components, X-ray contrast media, such as barium sulfate and zirconium oxide, can be further mentioned. In the present invention, zirconium oxide is preferable as the X-ray contrast medium. [0135] The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition described herein may be characterized by having a viscosity of 0.4 to 75,000 cp within 30 seconds after mixing of the components (A), (B) and (C) and the components to be contained when needed. [01361 Since the viscosity is in the above range, the composition is easily applied as an adhesive or a wound dressing. [0137] From the viewpoints of operability and fluidity, the viscosity is also described as being in the range of 0.4 to 10,000 op, more preferably 1 to 10,000 cp. [01381 The adhesive composition or the wound messing composition of the present invention preferably has a viscosity of 10 to 1,000,000 ep, more preferably 20 to 1,000,000 cp, still more preferably 30 to 800,000 cp, 60 seconds after mixing of the components (A), (B) and (C) and the components to be contained when needed [0139] Since the viscosity is in the above range, the composition can be easily extruded from a container as an adhesive or a wound dressing, and has excellent operability such as ease of applicat ion,.

SF-2299 49 [0140] The composition of the present invention is excellent in operability as an adhesive or a wound dressing, namely, application properties such as fluidity. Even if the composition of the present invention is compared with a composition using a peroxide 5 as an initiator component, the operator tends to be able to ensure a longer time than the time necessary for the mixing operation, and also from this viewpoint, the composition of the present invention is excellent in operability. [0141) A film, which is obtained from the adhesive 10 composition or the wound dressing composition of thepresent invention, is given 24 hours after the preparation of the composition and has a thickness of not less than 1 pm (preferably not more than 1 cm), a length of not less than 25 mm and a width of not less than 2 mm, preferably has a flexural elastic modulus, as measured under the 15 conditions of a test rate of 2 mm/min, of not more than 750 MPa, more preferably not more than 740 MPa, still more preferably not more than 730 MPa. A film, which is obtained from the composition, is given 24 hours after the preparation of the composition and has a thickness of not less than 1 pm (preferably not more than 1 cm), a length of 20 not less than 25 mm and a width of not less than 2 mm, may preferably have a flexural elastic modulus, as measured under the conditions of a test rate of 2 mm/min, of not more than 750 MPa, more preferably not more than 600 MPa, still more preferably not more than 550 MPa. [0142] The flexural elastic modulus of the above cured SF-2299 50 product may be preferably not less than 100 MPa, more preferably not less than 150 MPa, still more preferably not less than 200 MPa. [0143] A film, which is obtained from the adhesive composition or the wound dressing composition of the present invention, 5 is given 24 hours after the preparation of the composition and has a thickness of not less than 1 pm (preferably not more than 1 cm), a length of not less than 25 mm and a width of not less than 2 mm, preferably has a tensile elongation, as measured under the conditions of a test rate of 1 mm/min, of not less than 5%, more preferably not 10 less than 15%, still more preferably not less than 25%. [01443 The tensile elongation may be preferably not less than 5%, more preferably not less than 7%, still more preferably not less than 9%. The tensile elongation may be preferably not less than 30%, more preferably not less than 40%, still more preferably not 15 less than 50%. [0145] A cured product obtained from the adhesive composition or the wound dressing composition of the present invention provides a coating film having properties excellent for soft tissues or the skin, and is excellent in adhesion to the skin on the bending 20 portions, namely, portions where flexing or bending of a joint or the like is made. [0146] In the present invention, the monomer (A), the polymer (B) , the polymerization initiator composition (C) and the components to be contained when needed are previously mixed to prepare SF-2299 51 an adhesive composition or a wound dressing composition, and the composition can be used by applying it to a wound (affected part in the surgical operation, wound to be dressed), a soft tissue or the like. 5 [0147] When these components are mixed, the order of mixing is not specifically restricted, but it is preferable that the monomer (A) is first mixed with the polymerization initiator composition (C) and subsequently mixed with the polymer (B) , from the viewpoint that the components can be homogeneously and stably mixed. 10 [0148] When the adhes ive compos ition or the wound dres sing composition contains the polymerization inhibitor (D), it is preferable that a mixture of the monomer (A) and the polymerization inhibitor (D) is first mixed with the polymerization initiator composition (C) and subsequently mixed with the polymer (B) . 15 [0149) Prior to or during curing of the adhesive composition or the wound dressing composition of the present invention, the composition may be irradiated with electromagnetic waves, such as visible light, ionizing radiation (e.g., y-rays) or electron rays, toperformsterilization. Irradiationwithvisiblelightissometimes 20 desirable because the visible light does not greatly change the curing conditions. Sterilization may be carried out by treatment with gas, such as dry heat, steam, ethylene oxide (EO) or hydrogen peroxide, filtration, treatment with liquid, autoclave sterilization, or the like.

SF-2299 52 (0150] Prior to application of the adhesive composition or the wound dressing composition of the present invention to a wound, a soft tissue or the like, the surface of the wound, the soft tissue or the like may be disinfected with a disinfectant such as alcohol. 5 [0151] Prior to application of the adhesive composition or the wound dressing composition of the present invention to a wound, a soft tissue or the like, pretreatment may be further carried out for the purpose of improving adhesion properties. The pretreatment liquid is, for example, an aqueous solution containing 1 to 15% by 10 weight of citric acid and 1 to 5% by weight of iron(III) chloride. [0152] When the adhesive composition or the wound dressing composition of the present invention is applied to a wound, the composition is polymerized and cured to form a film, and therefore, the composition can be used for bonding the wound or covering the 15 surface of the wounded area (that is, after the wound edges are put together, the adhesive is applied to the surface of the wounded area, and it adheres to the surface and is cured) . For the purpose of fixing or protecting the edge or the whole of the cured film or maintaining or increasing the adhesive force, covering articles, such as film, 20 sheet, paper, plaster, bondage and gauze, may be used during or after application of the composition to a wound, a soft tissue surface or the like. These covering articles may have adhesiveness, or may have tackiness. [0153] The adhesive composition or the wound dressing SF-2299 53 composition can be applied to a wound during or after application of an alginate dressing material, a hydrogel or a hydropolymer to the wound. [0154] If there is a fear that the form or the performance 5 of the adhesive composition or the wound dressing composition of the present invention varies because of preservation or storage of a long time, thereby impairing the effect of the present invention, it is possible that the components comprising the monomer (A), the polymer (B) , the polymerization initiator composition (C) and the components 10 to be contained when needed, such as the polymerization inhibitor (D), are stored in the form of a kit which is used as an adhesive for soft tissues, an adhesive for wound dressing or a wound dressing and has two or more members in which the above components are encased independently or in groups divided in an optional combination, and 15 prior to use, the components are mixed to form the adhesive composition or the wound dressing composition. The members for encasing the components therein are, for example, sealable resin containers having gas barrier properties in order to prevent evaporation or scattering of the monomer (A) and the polymerization initiator composition (C) , 20 or glass syringes. The members for encasing the polymer (B) therein are, for example, resin containers having good sealing properties or glass containers in order to prevent moisture absorption. As for the quantity to be encased, there is a case where the quantity that is used up one time is encased or a case where the quantity that is SF-2299 54 used plural times is encased. [0155] Examples of manners to store the components include a manner in which the components are divided into three groups consisting of a mixture of the component (A) and the components to 5 be contained when needed, a mixture of the component (B) and the components to be contained when needed, and a mixture of the component (C) and the components to be contained when needed, followed by storing them; a manner in which the components are divided into two groups consisting of a mixture of the component (A), the component (B) and 10 the components to be contained when needed, and the component (C), followed by storing them; a manner in which the components are divided into two groups consisting of a mixture of the component (A) and the component (B) , and a mixture of the component (C) and the components to be contained when needed, followed by storing them; a manner in 15 which the components are divided into two groups consisting of a mixture of the component (A) , the component (B) and a part of the components to be contained when needed, and a mixture of the component (C) and a residue of the components to be contained when needed, followed by storing them; a manner in which the components are divided into 20 two groups consisting of a mixture of the component (A) and the components to be contained when needed, and a mixture of the component (B) and the component (C) , followed by storing them; a manner in which the components are divided into two groups consisting of the component (A) , and a mixture of the component (B) , the component (C) and the SF-2299 55 components to be contained when needed, followed by storing them; and a manner in which the components are divided into two groups consisting of a mixture of the component (A) and apart of the components to be contained when needed, and a mixture of the component (B), the 5 component (C) and a residue of the components to be contained when needed, followed by storing them. [0156) When the polymerization inhibitor (D) is contained, examples of manners to store the components include a manner in which the components are divided into three groups consisting of a mixture 10 of the component (A) and the components to be contained when needed, a mixture of the component (B) and the components to be contained when needed, and a mixture of the component (C) and the components to be contained when needed, followed by storing them; a manner in which the components are divided into two groups consisting of a mixture 15 of the component (A) , the component (B) , the component (D) and the components to be contained when needed, and the component (C) , followed by storing them; a manner in which the components are divided into two groups consisting of a mixture of the component (A) , the component (B) and the component (D), and a mixture of the component (C) and 20 the components to be contained when needed, followed by storing them; a manner in which the components are divided into two groups consisting of a mixture of the component (A), the component (B), the component (D) and a part of the components to be contained when needed, and a mixture of the component (C) and a residue of the components to SF-2299 56 be contained when needed, followed by storing them; a manner in which the components are divided into two groups consisting of a mixture of the component (A), the component (D) and the components to be contained when needed, and a mixture of the component (B) and the 5 component (C) , followed by storing them; a manner in which the components are divided into two groups consisting of a mixture of the component (A) and the component (D) , and a mixture of the component (B) , the component (C) and the components to be contained when needed, followed by storing them; and a manner in which the components are 10 divided into two groups consisting of a mixture of the component (A), the component (D) and a part of the components to be contained when needed, and a mixture of the component (B) , the component (C) and a residue of the components to be contained when needed, followed by storing them. 15 [0157] When a mixture of a monomer having an acidic group and a monomer having no acidic group is used as the monomer (A), the components may be stored in such a manner that the monomer having an acidic group is not in contact with the polymerization initiator composition, in addition to the above manners. Examples of such 20 manners include a manner in which the components are divided into two groups consisting of a mixture of the monomer having an acidic group, the component (B) and the components to be contained when needed, and a mixture of the monomer having no acidic group and the component (C), followed by storing them; a manner in which the components are SF-2299 57 divided into two groups consisting of a mixture of the monomer having an acidic group and the component (B), and a mixture of the monomer having no acidic group, the component (C) and the components to be contained when needed, followed by storing them; a manner in which 5 the components are divided into two groups consisting of a mixture of the monomer having an acidic group and the components to be contained when needed, and a mixture of the monomer having no acidic group, the component (B) and the component (C), followed by storing them; and a manner in which the components are divided into two groups 10 consisting of the monomer having an acidic group, and a mixture of the monomer having no acidic group, the component (B), the component (C) and the components to be contained when needed, followed by storing them. [0158] The components divided into two groups are placed 15 in separate members, e.g., containers such as syringes, and the members are encased in a kit that is used as an adhesive for soft tissues, an adhesive for wound dressing or a wound dressing, and the kit can be provided as an article. [0159) The constitution of the kit is not specifically 20 restricted as long as there is no fear that the form or the performance is changed by the storage to impair the ef fect of the present invention, but the kit preferably has constitution in which the monomer (A), the polymer (B) and the polymerization initiator composition (C) are each independently encased, and the monomer (A) is first mixed with SF-2299 58 the polymerization initiator composition (C) containing an organoboron compound and subsequently mixed with the polymer (B). By virtue of such constitution, an adhesive composition or a wound dressing composition having more stable performance tends to be 5 obtained. [0160] Examples of such kits include: a kit having members (e.g., containers, syringes) in which the monomer (A), the polymer (B) and the polymerization initiator composition (C) are each independently encased and having a member 10 (e.g., mixing container, mixing dish) for taking out the encased components from the members and mixing them; and a kit having one container which has three or more chambers separated by partitions, in said chambers the monomer (A) , the polymer (B) and the polymerization initiator composition (C) being each 15 independently encased, and having a stirring unit for mixing the monomer (A) and the polymerization initiator composition (C) with the polymer (B), said components (A) and (C) having passed through a bypass formed in a syringe owing to rapture of the partitions or shifting of the partitions. 20 [0161) When the kit contains the polymerization inhibitor (D), the kit preferably has constitution in which a mixture containing the monomer (A) and the polymerization inhibitor (D), the polymer (B) and the polymerization initiator composition (C) are each independently encased, and the mixture containing the monomer (A) SF-2299 59 and the polymerization inhibitor (D) is first mixed with the polymerization initiator composition (C) containing an organoboron compound and subsequently mixed with the polymer (B) . By virtue of such constitution, an adhesive for soft tissues, an adhesive for wound 5 dressing or a wound dressing having more stable performance tends to be obtained. [0162] Examples of such kits include: a kit having members (e.g., containers, syringes) in which a mixture containing the monomer (A) and the polymerization inhibitor 10 (D) , the polymer (B) and the polymerization initiator composition (C) are each independently encased and having a member (e.g., mixing container, mixing dish) for taking out the encased components from the members and mixing them; and a kit having one container which has three or more chambers 15 separated by partitions, in said chambers a mixture containing the monomer (A) and the polymerization inhibitor (D), the polymer (B) and the polymerization initiator composition (C) being each independently encased, and having a stirring unit for mixing the mixture containing the monomer (A) and the polymerization inhibitor 20 (D) and the polymerization initiator composition (C) with the polymer (B) , said mixture and said component (C) having passed through a bypass formed in a syringe owing to rapture of the partitions or shifting of the partitions. [0163] The kit having one container wherein the components SF-2299 60 are encased in the separated three or more chambers requires less labor as compared with a means wherein the composition of the present invention is divided, placed in two or more members, typically containers, and mixed immediately before use. Moreover, this kit 5 uses no mixing container or the like and can be economically used by taking a necessary amount of the composition out of the container and bringing it into contact with a jig such as sponge. [0164) It is also possible that a jig that is used for applying the adhesive composition or the wound dressing composition 10 to a wound, a soft tissue or the like is allowed to contain a part or the whole of the polymerization initiator composition (C) in advance, and the jig is brought into contact with the monomer (A) or a mixture containing the monomer (A) and the polymerization inhibitor (D), the polymer (B) and the components to be contained when needed to prepare 15 the adhesive composition or the wound dressing composition of the present invention in situ, followed by applying it to a wound, a soft tissue or the like. [0165] Examples of the jigs for applying the composition to a wound, a soft tissue or the like include a brush, a fiber ball, 20 a cloth, a sponge ball and a piece of sponge. [0166] In the kit, the aforesaid disinfectant liquid such as alcohol, the aforesaid pretreatment liquid for improving adhesion properties, the aforesaid covering article, etc. may be included. [0167] When the components of the composition are stored SF-2299 61 in the kit, they may be subjected to sterilization treatment with electromagnetic waves such as visible light preferably under the conditions that the components are not modified (e.g., monomer is not cured). 5 [0168] The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of the present invention can be used for, for example, adhesion of organism tissues, such as closure, protection or obstruction of wounds, fixing (adhesion) of soft tissue graft, 10 hemostasis, vascular anastomosis, vascular obstruction, bronchial anastomosis, bronchial obstruction and ophthalmologic operations. [0169] By directly applying the composition of thepresent invention to a wound formed in the outer skin of an organism such as skin or mucous membrane, the opening of the wound can be easily 15 closed. Moreover, the composition of the present invention can be used also for fixing a graft to the skin transplantation area in the skin transplantation. [0170] When the composition of the present invention is used as a wound dressing, the adhesive is not applied to the wound 20 surface usually, but the adhesive is applied to the surface of the wounded area after the wound edges are put together, and it adheres to the surface and is cured. In the case of a wound having no incised surface, such as scratch, crush wound or contused wound, the composition may be directly applied to the affected part in order SF-2299 62 to dress the wound. Examples (0171] The present invention is further described with 5 reference to the following examples, but it should be construed that the present invention is in no way limited to those examples. Examples 1A to 18A Reagents In the examples, the following compounds and composition were 10 used as the monomer (A) , the polymer (B) and the polymerization initiator composition (C). (0172] Monomer (A): 4-META/MMA, methyl methacrylate solution of 4-methacryloxyethyltrimellitic anhydride (weight ratio: about 5%) 15 Polymer (B) : mixture of three kinds of the following PMMA (polymethyl methacrylates) (bl) to (b3) and pigment The weight ratios of these components are as follows: in 100 parts by weight of the total amount of the three kinds of PMMA and the pigment, (bl) is contained in an amount of 20.03 parts by 20 weight, (b2) is contained in an amount of 62.5 parts by weight, (b3) is contained in an amount of 12.5 parts by weight, and the pigment is contained in the residual amount. Molecular weights and properties of the PMMA (1) to (3) are as follows.

SF-2299 63 (bl) weight-average molecular weight: 450,000, volume mean particle diameter: 26.7 pm, specific surface area: 2.913 m 2 /g (b2) weight-average molecular weight: 140,000, volume mean particle diameter: 8.2 pm, specific surface area: 0.827 m 2 /g 5 (b3) weight-average molecular weight: 140,000, volume mean particle diameter: 24.6 pm, specific surface area: 0.371 m 2 /g The volume mean particle diameter of PMMA (refractive index: 1. 49) was measured in the following manner. As a dispersion medium, special grade reagent methanol (refractive index: 1.33, available 10 from Wako Pure Chemical Industries, Ltd.) was used. The PMMA was dispersed in the dispersion medium by an ultrasonic homogenizer integrated in the apparatus for 5 minutes (output: 25 W), and the measurement was carried out under the concentration conditions of the proper range of the apparatus Loading Index at a circulation rate 15 of 50% (100%: 65 ml/sec) by the use ofMicrotracMT3300EXII (particle size distribution meter manufactured by Microtrac Inc.). [0173] The specific surface area is a value determined by nitrogen gas adsorption at the liquid nitrogen temperature (77 K) using Autosorb 3 (manufactured by Quantachrome Instruments) , and 20 is a value measured by BET method. (0174] Polymerization initiator composition (C): TBB A type, namely, partially oxidized tributylboron: 80 parts by weight, hexane: 19 parts by weight, ethanol: 1 part by weight Evaluation of viscosity SF-2299 64 In a sample tube, the polymer (B) was weighed in accordance with a blending ratio described in Examples 1A to 9A of the following Table 1. In the sample tube in which the polymer (B) had been weighed, the monomer (A) and the polymerization initiator composition (C), 5 which had been mixed together in a dif ferent sample tube in accordance with a blending ratio described in Examples 1A to 9A of the following Table 1 similarly to the above, were injected, and they were mixed together at 25 0 C to prepare an adhesive composition or a wound dressing composition of the present invention. 30 seconds after the 10 preparation, viscosity of the composition was measured. The viscosity at the time of preparation was not less than 0. 4 cp, and it was confirmed that the viscosity increased with time. The viscosity was measured by an E type viscometer (manufactured by Tokyo Keiki Inc., EHP type) at 25*C. The evaluation results are set forth in Table 1. 15 [0175] Evaluation of application properties In a syringe having a cap at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Examples 1A to 9A of the following Table 1. In this syringe, the monomer (A) and the polymerization initiator composition (C); which had been mixed 20 together in a sample tube in accordance with a blending ratio described in Examples 1A to 9A of the following Table 1 similarly to the above, were injected, and they were mixed together at 25 0 C. Thereafter, the cap of the syringe was removed, then a nozzle having a width of 1 cm and a thickness of 1 mm was fitted, and 1 ml of the composition SF-2299 65 mixed was applied by 4 cm onto a polyethylene sheet. The application properties were evaluated based on the 5-grade evaluation of 1 to 5. That is to say, a case where the width of the applied composition was not less than 1 cm but less than 1.2 cm was evaluated to be 5; 5 a case where the width of the applied composition was not less than 1.2 cm but less than 1.4 cm was evaluated to be 4; a case where the width of the applied composition was not less than 1.4 cm but less than 1. 6 cm was evaluated to be 3; a case where the width of the applied composition was not less than 1.6 cm was evaluated to be 2; and a 10 case where application was impossible was evaluated to be 1. The evaluation results are set forth in Table 1. [0176] It was confirmed that in the case of the adhesive composition or the wound dressing composition containing the components (A), (B) and (C) and having a viscosity of less than 0.4 15 cp after 30 seconds, the width of the applied composition was too large, and in the case of the composition having a viscosity of more than 75000 cp after 30 seconds, application using a syringe was impossible.

O U) -H 0) 4i-J -H <04 -4 0 04 P o-'O < (N L O LO LO U) U) o 0) >0 a U) c)0) -H U) O M4 00) C0 U)4LO N W -H 4- . ( N D r t > o H oN o N (N N N N N - H 4 413 -d o o o o o El 0 ty ko OO L O L Ln i OL U)U U - - - u u u u u U U l --- r- O OO O O) 0 0 0 0 0 0 0 0 0 En l H N OH ON O . O Oo O. 40)4 4J 4- ) 4 4) 41) 4.) H - o r-rotn t q- VU) U) U) co U) U) U) U) ul 0 0 0 0 0 0 0 0 -0 0 -- 0 0 0 0 0 -0--- 0 o 0 -d - -- -. v - --- -U - -- - - -- 0u'- ' o,-- 0 - - .0 CD o 0 0 .0 - , 0 0 o*0 S- 0 IV - L -( 0- . C- - Om o-w00- wr- 0 U. O - C o - 0 P - 0 o - C ) WH - - P . CO 0 f -- 1 0 - 0 r - 0 N - o r - 0 m - o 0o 0 0 0 o -H H o -'-4H * H - w H L*CH r*CH -'- C H H C *TCH r-d O 0 O O O O O O O L O V 4 O ---- N ------ ----- -- 9 -----N -- ~-N-------' u Q< m ro r- m o r m to N c rd m r 4d m a to4 o 4O m --- -N - '-- to-- N -- r-- N - - -N - -- N - -H -H 0) 0) 0 0) 0) 0 0 0 0 0) 00 0 0 0 0 0) 0 0 0 0 0 0 0 0) 0H 0 0 .0 0 1 -4 H CH m H v r H H HHr- H H c H H c HH C H H V 00. 0 0 0. .. 0 0. . A 0 4 0 03 a N N -N N 1 r-I H ri r-l ~ H rl r- jA en oD r) (1 x x x SF-2299 67 [0178] Preparation of polymerized and solidified film In a 5 ml sample tube, the polymer (B) was weighed in accordance with a blending ratio described in Examples 10 to 13 of the following Table 2. In the sample tube in which the polymer (B) had been weighed, 5 a mixture of the monomer solution (A) and the polymerization initiator composition (C), which had been prepared in a different 1 ml sample tube in accordance with a blending ratio described in Examples 10A to 13A of the following Table 1 similarly to the above, was introduced, and they were mixed together at 25 0 C for about 5 seconds using a glass 10 bar so that the mixture might become homogeneous. [0179] The resulting adhesive composition or wound dressing composition was injected into a syringe and immediately filled in a frame to prepare a sample film in accordance with the following procedure, as illustrated in Fig. 1. 15 (0180] On a glass plate, a sheet of PE Lumirror (trade mark) and a fluororesin frame having a thickness of 0.5 mm (internal size of frame: 25 mm (length) x 2 mm (width)) were superposed in this order. In this frame, the adhesive composition or the wound dressing composition prepared was filled. The filling work was carefully 20 carried out so that bubbles should not be formed. After the filling was completed, a sheet of PE Lumirror (trade mark) and a glass plate were further superposed thereon in this order, and the four corners of the outermost two glass plates were fixed with clips. Thereafter, they were allowed to stand for 24 hours at 25 0 C (room temperature), SF-2299 68 and then the film was taken out of the frame. When the resulting film had irregularities on the surfaces, the surfaces were abraded with a waterproof abrasive paper #600 to remove irregularities, whereby a sample film was prepared. The resulting sample film had a size 5 of a length of 25 mm, a width of 2 mm and a thickness of 0.5 mm. [01811 Flexural elastic modulus (test rate: 2 mm/min) and tensile elongation (test rate: 1 mm/min) (SS properties of film) of the sample film were determined by EzTest/CE manufactured by Shimadzu Corporation. The SS property values of the film are each 10 a mean of values measured on four sample film strips. The evaluation results are set forth in Table 2.

o)P 0 H -- )a . V) V C0 Q) 1- 03 CDO 1) r~0 0 0 0 OY) LO o (N N -0 0 0 0 4-1 U) 0 0m (o (Y) o o o 0 * U U U U U)0 0 0 0 .1- H H -H 4-).j 41 4-) 4-) rA r-q rq *rq SU) C C) U) 0 0 0 0 E E 0 0 0 S u u u u -D N 0 0 0 MN0 - N - N -4 r- -4 N v- . 0 0 .0 . .0 . * 0 om 4r--) 4 .O 4 H o 4J -'H (T -N r(to0( L()'to r o.- HN 0 u -1)(N L -J 4 r- 5 0 F 0r 05 0 0F -4 U) MnV -H - o N -H * HO -H n -d w H V N O 00 N 0 w N v r. H LO C: L N 1: in inO 04 0 0 0N u .Q 4 d4 M 4 t 9 Q CQ (0 N NN )N N 0-(1 X 4: -. >Cz M) C 4 A E .) on4 (a r. H <C0 - -- tX 12 D4X0 UX0 3 X 4a SF-2299 70 [0183] Examples l4A to 17A (evaluation of adhesive strength using skin of Yucatan miniature pig (YMP) In a 5 ml sample tube, the polymer (B) was weighed in accordance with a blending ratio described in Examples 14A to 17A of the following 5 Table 3. In this sample tube, a mixture of the monomer (A) and the polymerization initiator composition (C), which had been prepared in a different 1 ml sample tube in accordance with a blending ratio described in Examples 14A to 17A of the following Table 3 similarly to the above, was introduced, and they were mixed together at 25 0 C 10 for about 5 seconds using a glass bar so that the mixture might become homogeneous. [0184] The resulting composition was injected into a syringe, and a sample for evaluating adhesive strength was prepared in accordance with the following procedure, as illustrated in Fig. 15 2. On a glass plate, a sheet of PE lumirror (trade mark), YMP skin of 2 cm x 2 cm, from which fat tissue had been cut off and which had been degreased with 70% aqueous ethanol (upper side: outer skin), and a fluororesin sheet frame having a thickness of 0.5 mm, from which a complete round having a diameter of 4.8 mm (area: 18.1 mm 2 ) had 20 been removed, were superposed, and in the fluororesin sheet frame, the adhesive composition or the wound dressing composition shown in Examples 14 to 17 was filled. The filling work was carefully carried out so that bubbles should not be formed. After the filling was completed, YMP skin (lower side: outer skin), a sheet of PE Lumirror SF-2299 71 (trade mark) and a glass plate were further superposed thereon in this order, and they were allowed to stand for 24 hours at about room temperature of 250C under a load of 150 g. Thereafter, the glass plates and the PE lumirror (trade mark) on the both sides were removed 5 to obtain a sample for evaluating adhesive strength. Tension (test rate: 1 mm/min) and adhesive strength of the sample filmwere determined by EzTest/CE manufactured by Shimadzu Corporation. The value is a mean of values measured on four test strips. The evaluation results measured as above are set forth in Table 3.

-J C S-I 4 1J U) a) a)-. O0) H a) 0 (N m N N O- - 41) U) 0 O D 0 0 (N U)0 0 0. o - o o C C C C U) 0 0 0 0 - 00- 0 o L - o -W - - - - o ( H - H C -C-O - - OD O o 04 . o n . 0o . r 0 DrO -) r- LO - LO 0) 4- L-O 4J O -e mt m Lf -. y 0 0J 0J 4- -o -) t-. 0 m -H 0) M" .4-) & C E C E E C E E r -d- CD N r- -dl r- r- -r LO LO -ri my r -rd Oto $N( C) 0 C we a)rC e $4 H -OH . - . .. ,- .0 ..

o C~r4JC-If4JcO 4-) 4~4-) ..u (( 4 m C <m (O4 m N -N--HN -- N 0O - -dO *di -d -H -( r- -H o o-- LCLr--4m-- S0OD OO o k H a C H a C a a)-. C a) () a to N0 0S 0 0 Co I HH *H *H o N '- '- N E- M E-4 H wQ w SF-2299 73 (0186] Example 18A (evaluation of tissue-injurious properties using guinea pig The back skin of a Hartley type guinea pig of 5 weeks old, whose hair had been clipped and removed, was incised by 3 cm to 4 cm under 5 anesthesia. In a syringe whose discharge opening had been closed with a cap, the polymer (B) was weighed in accordance with a blending ratio described in Example 18 of the following Table 4. Then, the monomer solution (A) and the polymerization initiator composition (C) were mixed in a sample tube in accordance with a blending ratio 10 described in Example 18 similarly to the above, and the mixture was injected into the syringe in which the polymer (B) had been introduced, and they were mixed together at 25 0 C. Thereafter, the cap of the syringe in which the three components of (A) , (B) and (C) had been placed was removed, then a nozzle having an opening of a width of 15 1 cm and a thickness of 1 mm was fitted, and within 10 seconds, the adhesive composition mixed was extruded through the opening of the syringe nozzle to apply the composition to the incised wound of the guinea pig, said incised wound having been sealed by pressing down it with a finger. 20 [0187] 30 minutes, 2 hours, 6 hours, 24 hours, 72 hours and 168 hours after the treatment, properties of the wound, degree of redness and degree of expansion were examined, then the animal was subjected to mercy killing, and the skin of 1 cm x 1 cm was cut out from the applied part and fixed in formalin. Thereafter, a tissue SF-2299 74 slice was prepared in a conventional manner, then subjected to hematoxylin-eosin staining and observed by an optical microscope. (0188] As a result, there was no problem with the properties of the skin, and redness and expansion were not detected. 5 In the observation of the tissue slice, inflammation caused by application of the adhesive composition or the wound dressing composition was not observed, and harmfulness to the skin tissue was not confirmed. (0189] 10 Table 4 Adhesive composition or wound dressing composition parts() by weight) Ex. 18A Monomer (A): 192mg (52.6) Polymer (B): 166mg (45.5) Polymerization initiator composition (C) : 7mg (1. 9) [0190J Examples 1B to 7B, Reference Examples 1B to 4B In the following examples and comparative examples, the same monomer (A) , the same polymer (B) and the same polymerization initiator 15 composition (C) as in the above examples were used. Asa polymerization inhibitor (D), the following one was used. (0191] Polymerization inhibitor (D) : hydroquinone monomethyl ether In the monomer (A) , this polymerization inhibitor was dissolved 20 in an amount described in the following Table 5, Table 6 and Table 7.

SF-2299 75 [0192] Evaluation of application properties In a syringe whose discharge opening had been closed with a cap, 1156 mg (40.0 parts by weight) of the polymer (B) was weighed. Separately, 1680 mg (58.1 parts by weight) of the monomer (A), in 5 which the polymerization inhibitor (D) had been dissolved in an amount (based on the polymer (A) ) described in Examples 1B to 3B and Reference Examples 1B and 2B of the following Table 5, and 54 mg (1. 9 parts by weight) of the polymerization initiator composition (C) were weighed in a sample tube and mixed together, then the mixture was injected 10 into the syringe in which the polymer (B) had been placed, and they were mixed together at 25 0 C. Thereafter, the cap of the syringe in which three components of (A), (B) and (C) had been placed was removed, then a nozzle having an opening of a width of 1 cm and a thickness of 1 mm was fitted, and 1 ml of the adhesive composition mixed was 15 applied by 4 cm onto a polyethylene sheet. The application properties were evaluated based on the 5-grade evaluation of 1 to 5. That is to say, a case where the width of the applied composition was not less than 1 cm but less than 1.2 cm was evaluated to be 5; a case where the width of the applied composition was not less than 1.2 cm 20 but less than 1.4 cm was evaluated to be 4; a case where the width of the applied composition was not less than 1.4 cm but less than 1.6 cm was evaluated to be 3; a case where the width of the applied composition was not less than 1.6 cm was evaluated to be 2; and a case where application was impossible was evaluated to be 1. The SF-2299 76 evaluation results are set forth in Table 5. [0193] Evaluation of curing time In a syringe whose discharge opening had been closed with a cap, 1156 mg (40.0 parts by weight) of the polymer (B) was weighed. 5 Separately, 1680 mg (58.1 parts by weight) of the monomer (A), in which the polymerization inhibitor (D) had been dissolved in an amount (based on the monomer (A) ) described in Examples 1B to 3B and Reference Examples 1B and 2B of the following Table 1, and 54 mg (1.9 parts byweight) of the polymerization initiator composition (C) were weighed 10 in a sample tube and mixed together, then the mixture was injected into the syringe in which the polymer (B) had been placed, and they were mixed together at 25 0 C. Thereafter, the cap of the syringe in which three components of (A), (B) and (C) had been placed was removed, then a nozzle having a width of 1 cm and a thickness of 1 mm was fitted, 15 and 1 ml of the adhesive composition mixed was applied by 4 cm onto a polyethylene sheet. Then, the adhesive composition was held as it was, and a fluororesin bar was touched with the surface of the applied composition to examine the time at the end of which tacking (cobwebbing) stopped. This time was regarded as a curing time. The 20 evaluation results are set forth in Table 5.

SF-2299 77 [0194] Table 5 Polymerization Application Curing time inhibitor (D) properties (second(s)) (ppm) Ref. Ex. 1B 0 1 0 Ex. 1B 10 5 5 Ex. 2B 200 5 60 Ex. 3B 5000 3 750 Ref. Ex. 2B 10000 2 1800 [0195) Evaluation of storage stability 5 In a sample tube of 5 ml, 3000 mg of the monomer (A), in which the polymerization inhibitor (D) had been dissolved in an amount (based on the monomer (A) ) described in Examples 4B to 6B and Reference Examples 3B and 4B of the following Table 6, was weighed, and it was stored for 10 days in a constant temperature container at 60*C. After 10 10 days, the sample tube was opened to examine curing of the contents. The evaluation results are set forth in Table 6. [0196) Table 6 Polymerization Storage stability inhibitor (D) (ppm) Ref. Ex. 3B 0 cured Ex. 4B 100 not cured Ex. 5B 200 not cured Ex. 6B 5000 not cured Ref. Ex. 4B 10000 not cured 15 [0197] Evaluation of tissue-injurious properties using guinea SF-2299 78 The back skin of a Hartley type guinea pig of 5 weeks old, whose hair had been clipped and removed, was incised by 3 cm to 4 cm under anesthesia. In a syringe having a cap at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Example 5 7B of Table 3. In this syringe, the monomer (A) having been mixed with the polymerization inhibitor (D) in a sample tube in accordance with a blending ratio described in Example 7 of Table 3 similarly to the above, and the polymerization initiator composition (C) were injected, and they were mixed together at 25 0 C. Thereafter, the cap 10 of the syringe was removed, then a nozzle having an opening of a width of 1 cm and a thickness of 1 mm was fitted, and the adhesive composition mixed was applied to the incised part. 30 minutes, 2 hours, 6 hours, 24 hours, 72 hours or 168 hours after the treatment, properties of the skin, presence or absence of redness and presence or absence of 15 expansion were examined, then the animal was subjected to mercy killing, and the skin of 1 cm x 1 cm was cut out from the applied part and fixed in formalin. Thereafter, the sample was subjected to H-E staining, and a tissue slice prepared was observed by an optical microscope. 20 [0198] As a result, there was no problem with the properties of the skin, and redness and expansion were not detected. In the observation of the tissue slice, inflammation caused by application of the adhesive composition was not observed, and harmfulness to the skin tissue was not confirmed.

SF-2299 79 [0199] Table 7 Adhesive composition (part(s) by weight) Ex. 7B Monomer (A): 166mg (45.5) Polymerization inhibitor (D) (based onmonomer (A)) : 200ppm Polymer (B): 192mg (52.6) Polymerization initiator composition (C): 7mg (1.9) [0200) Examples 1C to 31C, Comparative Examples 1C to 4C 5 In the following examples and comparative examples, the same monomer (A) and the same polymerization initiator composition (C) as in the above examples were used. As a polymer (B), a mixture of the aforesaid polymers (bl), (b2) and (b3) in a mixing ratio described in the following Table 8 was used. 10 Evaluation of viscosity In a 5 ml latex-free luer lock syringe (manufactured by HENKE SASS WOLF) having a plastic cap (manufactured by Osaka Chemical Co., Ltd.) at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Example 1C, Example 3C, Example 15 4C, Example 9C, Example 10C, Example 15C, Example 17C, Example 19C, Example 22C, Example 23C and Example 27C of the following Tables 8 to 13. In this syringe, the monomer (A) and the polymerization initiator composition (C), which had been mixed together in a 10 ml glass sample tube in accordance with a blending ratio described in 20 the examples similarly to the above, were injected, and the syringe was vigorously shaken with hand at 25*C for 20 seconds to stir and SF-2299 80 mix the contents. Thereafter, the cap of the syringe was removed, then an 18G needle available from Terumo Corporation was fitted, and 60 seconds after the preparation, the viscosity was measured at 35 0 C by the use of a rheometer (manuf actured by HAAKE, RS150) . The viscosity 5 at the time of preparation was not less than 0. 4 cp, and it was confirmed that the viscosity increased with time. The evaluation results are set forth in Tables 8 to 15. [0201) Evaluation of solubility In a 5 ml latex-free luer lock syringe (manufactured by HENKE 10 SASS WOLF) having a plastic cap (manufactured by Osaka Chemical Co., Ltd.) at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Examples 1C to 31C and Comparative Examples 1C to 4C of the following Tables 8 to 15. In this syringe, the monomer (A) and the polymerization initiator composition (C), 15 which had been mixed together in a 10 ml glass sample tube in accordance with a blending ratio described in Examples 1C to 31C and Comparative Examples 1C to 4C similarly to the above, were injected, and the syringe was vigorously shaken with hand at 25"C for 20 seconds to stir and mix the contents. Thereafter, the state of the mixture in the syringe 20 was confirmed by visual observation. A case where a powder of the polymer (B) was not detected was evaluated to be 3; a case where a powder of the polymer (B) was slightly detected was evaluated to be 2; and a case where a powder of the polymer (B) was detected in a large amount was evaluated to be 1. The evaluation results are set SF-2299 81 forth in Tables 8 to 15. [02021 Evaluation of application properties In a 5 ml syringe (manufactured by HENKE SASS WOLF) having a plastic cap (manufactured by Osaka Chemical Co., Ltd.) at the luer 5 part, the polymer (B) was weighed in accordance with a blending ratio described in Examples 1C to 31C and Comparative Examples 1C to 4C of the following Tables 8 to 15. In this syringe, the monomer (A) and the polymerization initiator composition (C), which had been mixed together in a sample tube in accordance with a blending ratio described 10 in Examples 1C to 31C and Comparative Examples IC to 4C similarly to the above, were injected, and the syringe was vigorously shaken with hand at 25*C for 20 seconds to mix the contents. Thereafter, the cap of the syringe was removed, then a nozzle having an opening of a width of 1 cm and a thickness of 1 mm was fitted, and 1 ml of 15 the composition mixed was applied by 4 cm onto a polyethylene sheet. Extrusion from the container was evaluated as follows. That is to say, a case where extrusion could be easily carried out was evaluated to be 3; a case where extrusion could be carried out by applying a pressure with hand was evaluated to be 2; and a case where extrusion 20 was impossible was evaluated to be 1. Spreading of the applied composition was evaluated as follows. That is to say, a case where the width of the applied composition was not less than 1 cm but less than 1.2 cm was evaluated to be 5; a case where the width of the applied composition was not less than 1.2 cm but less than 1. 4 cm was evaluated SF-2299 82 to be 4; a case where the width of the applied composition was not less than 1.4 cm but less than 1.6 cm was evaluated to be 3; a case where the width of the applied composition was not less than 1.6 cm but less than 1.8 cm was evaluated to be 2; a case where the width 5 of the applied composition was not less than 1.8 cm but less than 3 cm was evaluated to be 1; and a case where the width of the applied composition was not less than 3 cmwas evaluated to be 0. The evaluation results are set forth in Tables 8 to 15. [0203] Preparation of polymerized and solidified film 10 In a 5 ml latex-free luer lock syringe (manufactured by HENKE SASS WOLF) having a plastic cap (manufactured by Osaka Chemical Co., Ltd.) at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Example 1C, Example 3C, Example 4C, Example 10C, Example 15C, Example 17C, Example 19C, Example 22C, 15 Example 23C, Example 27C and Example 28C of the following Tables 8 to 13. In this syringe, the monomer (A) and the polymerization initiator composition (C) , which had been mixed together in a sample tube in accordance with a blending ratio described in Example 1C, Example 3C, Example 4C, Example 10C, Example 15C, Example 17C, Example 20 19C, Example 22C, Example 23C, Example 27C and Example 28C similarly to the above, were injected, and the syringe was vigorously shaken with hand at 25 0 C for 20 seconds to mix the contents. The resulting composition was immediately filled in a frame to prepare a sample film in accordance with the following procedure, as illustrated in SF-2299 83 Fig. 1. On a glass plate, a sheet of PE Lumirror (trade mark) and a fluororesin frame having a thickness of 0.5 mm (internal size of frame: 25 mm (length) x 2 mm (width) ) were superposed in this order. In this frame, the adhesive composition or the wound dressing 5 composition prepared was filled. The filling work was carefully carried out so that bubbles should not be formed. After the filling was completed, a sheet of PE Lumirror (trade mark) and a glass plate were further superposed thereon in this order, and the four corners of the outermost two glass plates were fixed with clips. Thereafter, 10 they were allowed to stand for 24 hours at 25 0 C (room temperature), and then the film was taken out of the frame. When the resulting film had irregularities on the surfaces, the surfaces were abraded with a waterproof abrasive paper #600 to remove irregularities, whereby a sample film was prepared. The resulting sample film had a size 15 of a length of 25 mm, a width of 2 mm and a thickness of 0.5 mm. [0204] Flexural elastic modulus (test rate: 2 mm/min) and tensile elongation (test rate: 1 mm/min) of the sample film were determinedby anAutograph (EZ-S manufacturedby Shimadzu Corporation) . The values of the flexural elastic modulus and the tensile elongation 20 of the film are each a mean of values measured on four sample film strips. The evaluation results are set forth in Tables 8 to 13. [0205] Evaluation of adhesive strength using YMP skin Testof adhesive strength was carried out based onASTM F2255-05 using YMP skin (available fromCharles River Laboratories Japan, Inc.) .

SF-2299 84 That is to say, YMP skin having a thickness of 2 to 3 mm, from which a fat layer had been removed, was cut into a size of 25 mm (width) x 20 mm (length) , and both surfaces of the skin were wiped with paper. Then, the width of the skin was set to the edges of an acrylic plate 5 having a size of 25 mm (weight) x 80 mm (length), and the dermis side of the skin was bonded to the plate withAron Alpha (trademark, available from TOAGOSEI CO., LTD.) in such a manner that the outer skin was on the upper side. Thereafter, to the skin (outer skin) of an area having a length of not less than 10 mm from the edge of the acrylic 10 plate in the longitudinal direction and to the side surface of the skin, Teflon Grease (trade mark) was applied to define an "adhesive application surface (25 mm (width) x 10 mm (length))", whereby an adherend was formed. This adherend was wrapped up in gauze having been soaked with a physiological saline solution, then placed in a 15 closed container and kept warm at 37*C for 30 minutes. Thereafter, in a 5 ml latex-free luer lock syringe (manufactured by HENKE SASS WOLF) having a plastic cap (manufactured by Osaka Chemical Co., Ltd.) at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Example 1C, Example 3C, Example 4C and 20 Example 17C of the following Table 8 and Table 11. In this syringe, the monomer (A) and the polymerization initiator composition (C), which had been mixed together in a sample tube in accordance with a blending ratio described in Example 1C, Example 3C, Example 4C and Example 17C similarly to the above, were injected, and the syringe SF-2299 85 was vigorously shaken with hand at 25*C for 20 seconds to mix the contents, whereby an adhesive composition or a wound dressing composition was prepared. The adhesive composition or the wound dressing composition was applied to the adhesive application surface 5 (25 mm x 10 mm) . Two of such samples were prepared, and these were laid one upon the other in such a manner that the adhesive applied surfaces faced each other, and allowed to stand still for 1 hour under a load of 140 g. Thereafter, the resulting sample was wrapped up in gauze having been soaked with a physiological saline solution, 10 placed in a container and allowed to stand still at 37 0 C for 24 hours to prepare an adhesive strength evaluation sample. [02061 The evaluation sample was subjected to tensile test using an Autograph (EZ-S manufactured by Shimadzu Corporation) at a test rate of 5 mm/min. A mean of values measured on four test 15 strips was determined as adhesive strength. The evaluation results are set forth in Table 8 and Table 11. [0207) Overall evaluation A case where the points of solubility and application properties (extrusion from container, spreading of applied composition) were 20 each 3 or more was evaluated to be AA; a case where the points of solubility and application properties (extrusion from container, spreading of applied composition) were each 2 or more was evaluated tobeA; acasewherethepointsofsolubilityandapplicationproperties (extrusion from container) were each 2 or more and the point of SF-2299 86 application properties (spreading of applied composition) was 1 or more was evaluated to be B; and any of a case where the point of solubility was 1, a case where the point of application properties (extrusion from container) was 1, and a case where the point of application 5 properties (spreading of applied composition) was 0 was evaluated to be C. The evaluation results are set forth in Tables 8 to 15.

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-1 W* N(NN( CJN *H 4.J 0 r,. (J (N CV C(N to4-4 _ _ __ _ 44I C 0 - 4 (N mN .- I -44 C)C 0) 0 0 0 4-q 4-i4 0 0 0 H R- 0 0 0 0) 0 0 ) o o CCl $ 0. LAD 0 0 .0 U) CDtn 04-) 4-I . Hr 4j 0~* m . o )C r 0o L oi dP dP dP dn 4 PdP Ln M CPd Pr 0.- 0~f LA L)A~ 0 u n N N -1 N4C *H N4 C- 0 w 4J r 0 t> -4 4 $4-4. Q 00 0~0 L) 0 0 0 0N 0) 0N 0-H 00m 1 r- H-4iL 44N Q 0.14-) C n o E C: _ 00) 0 E-4 u zu SF-2299 105 [0220] Confirmation of healing of incised part using rat A male SD rat of 5 weeks old was anesthetized with Somnopentyl and then subjected to hair shearing. A penetrating skin cut wound of 30 mm was made at the position of 5 mm from the xiphoid process 5 toward the tail. In a5 ml latex-free luer lock syringe (manufactured by HENKE SASS WOLF) having a plastic cap (manufactured by Osaka Chemical Co., Ltd.) at the luer part, the polymer (B) was weighed in accordance with a blending ratio described in Example 34C of Table 16. In this syringe, the monomer (A) and the polymerization initiator composition 10 (C), which had been mixed together in a 10 ml glass sample tube in accordance with a blending ratio described in Example 34C of Table 16 similarly to the above, wereinjected, and the syringe was vigorously shaken with hand at 25"C for 20 seconds to stir and mix the contents. Thereafter, the plastic capwas removed, then a nozzle having an opening 15 of a width of 1 cm and a thickness of 1 mm was fitted. Bleeding at the cut wound was stopped using gauze, and then, with tightly pressing down the joined surface, 500 pl of the adhesive was applied thereto. 1 week, 2 weeks or 3 months after the treatment, the rat was subjected to mercy killing, and the abdominal tissue (skin and subcutaneous 20 tissue) having a size of 3 cm (length) x 2 cm (width) was extracted and fixed in formalin. After the fixation, a paraffin embedded block wasprepared, anditwassubjectedtohematoxylin-eosin (H-E) staining, followed by evaluation of the degree of healing by microscopic observation.

106 [0221] As a result, it was confirmed that the incised part where the adhesive for skins or the wound dressing composition had been applied did not differ from a non-incised tissue, and it had healed sufficiently. Reference Signs List [0222] 11: glass plate, 12 Lumirror (trade mark), 13; fluororesin frame (the central white part indicates a space of 25 mm (length) x 2 mm (width), and this part, is filled with the adhesive composition or the wound dressing composition.) 21: glass plate, 22; Lumirror (trade mark), 23: YMP skin (outer skin: lower side) , 24. fluororesin frame (the central white part indicates a complete round having a diameter of 4.8 mm, and this part is filled with the adhesive composition or the wound dressing composition. ) 31: Teflon Grease applied part, 32: YMP skin (outer skin: upper side), 33: acrylic plate [0223] Throughout this specification and the claims which follow, unless the context requires otherwise, the word c omprisee, and variations such as "comprises" and "comprising, will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. [02241 The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common 106A general knowledge in the field of endeavour to which this specification relates,

Claims (17)

1. An adhesive composition for soft tissues, an adhesive composition for wound dressing or a wound dressing composition, comprising a: monomer (A), a polymer (B) and a polymerization initiator composition (C) containing an organoboron compound, with the amount of the polymer (B) being in the range of 33 to less than 68 parts by weight, based on the total amount of the monomer (A), the polymer (B) and the polymerization initiator composition (C) being 100 parts by weight; and having a viscosity of 10 to 1,000,000 cp 60 seconds after mixing of the components (A), (B) and (C), wherein the polymer (B) is a polymer mixture comprising polymer particles (bl) having a weight average molecular weight of 30x104 to 60x10 4 and a specific surface area of 1.5 to 4.5 (mpg polymer particles (b2) having a weight-average molecular weight of 5x10 4 to 20x10 4 and a specific surface area of 0.51 to 1.2 (m/g) and polymer particles (b3) having a weight-average molecular weight of Sx0 to 20x10* and a specific surface area of 0.1 to 0.5 (m 2 /g) said polymer mixture comprising the polymer particles (bi) in an amount of 0 to less than 10% by weight based on the total weight of the polymer particles (bl), (b2) and (b3), and the polymer particles (b2) and the polymer particles (b3) in a total amount of more than 90 to 100% by weight based on the total weight of the polymer particles (bl) , (b2) and (b3) H:\EFHl~ntrwoven\NRPentblnDCC\E~F706359_1 idoc-9/12/2014 - 108

2. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in claim 1, wherein a film obtained from said adhesive composition or wound dressing composition, 24 hours after preparation of said composition, having a thickness of not less than 0.1 pm, a length of not less than 25 mm and a width of not less than 2 mm, has: a flexural elastic modulus, as measured under the conditions of a test rate of 2 mm/min, of not more than 750 MPa; and a tensile elongation, as measured under the conditions of a test rate of 1 mm/min, of not less than 5%.

3. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in claims 1 or 2, further comprising a polymerization inhibitor (D).

4. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in claim 3, wherein: the content of the polymerization inhibitor (D) is in the range of 10 to 5000 ppm based on the amount of monomer (A).

5. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in claim 3 or 4, wherein the polymerization inhibitor (D) is at least one substance selected from hydroquinone, dibutylhydroquinone, PM:trl-ilIucIflcYCfl'hKriiuLR t~ritAKAJ,b.OC-Iw/I/J~44 - 109 hydroquinone monomethyl ether, 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-p-cresol, catechol, pyrogallol, benzoquinone, 2-hydroxybenzoquinone, p-methoxyphenol, t-butylcatechol, butylated hydroxyanisole, butylated hydroxytoluene and t-butylhydroquinone.

6. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in any one of claims 1 to 5, which further comprises an ultraviolet light absorber.

7. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in any one of claims 1 to 6, which further comprises a plasticizer.

8. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in any one of claims 1 to 7, which further comprises at least one substance selected from: anti-infectious agents, antibiotics, antibacterial agents, anti-virus agents, analgesics, compositions of analgesics, anorectic drugs, antihelmintic drugs, antiarthritic agents, antiasthmatic drugs, anticonvulsants, antidepressants, antidiuretics, antidiarrheal agents, antihistamine drugs, anti inflammatory drugs, antimigraine drugs, antiemetic agents, antineoplastic drugs, antiparkinsonian agents, antipruritic drugs, antipsychotics, antipyretic drugs, antispasmodic drugs, anticholinergic agents, - 110 sympathomimetic agents, cardiovascular drugs, antiarrhythmic drugs, antihypertensive drugs, diuretics, vasodilators, immunosuppressant drugs, muscle-relaxant drugs, parasympatholytic drugs, stimulants, sedative drugs, tranquilizers, cholinergic agents, chemotherapeutic drugs, radio pharmaceuticals, bone inductive drugs, heparin neutralizer agents of static bladder, procoagulants, hemostatic agents, xanthine derivatives, hormones, proteins of natural origin or proteins synthesized by genetic engineering, polysaccharides, glycoproteins, lipoproteins, oligonucleotides, antibody, antigen, vasopressin, vasopressin analogs, epinephrine, selectin, clot promoting toxicants, plasminogen activating factor inhibitors, platelet activators, synthetic peptides having hemostatic action, and perfumes.

9. The adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition of claim 8, further comprising at least one perfume selected from orange oil, grapefruit oil, lemon oil, lime oil, clove oil, wintergreen oil, peppermint oil, peppermint spirit, banana distillate, cucumber distillate, honey distillate, rose water, menthol, anethole, alkyl salicylate, benzaldehyde, monosodium glutamate, ethylvanillin, thymol and vanillin.

10. An adhesive kit for soft tissues, an adhesive agent kit for wound dressing or a wound dressing kit when used to produce the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound H TFH.nimcwoo NRPrlbl\DCCaEF7HI6358 _l doc-l1/,21.14 -111 dressing composition as claimed in claim 1, said kit having members in which the monomer (A), the polymer (B) and the polymerization initiator composition (C) containing an organoboron compound are encased in two or more divided groups so that none of the two or more divided groups comprise the monomer (A) , the polymer (B) and the polymerization initiator composition (C).

11. The adhesive kit for soft tissues, the adhesive agent kit for wound dressing or the wound dressing kit as claimed in claim 10, in which the monomer (A), the polymer (B) and the polymerization initiator composition (C) are each independently encased, and, when used, the monomer (A) is first mixed with the polymerization initiator composition (C) containing an organoboron compound and subsequently mixed with the polymer (B).

12. An adhesive kit for soft tissues, an adhesive agent kit for wound dressing or a wound dressing kit when used to produce the adhesive composition for soft tissues, the adhesive composition for wound dressing or the wound dressing composition as claimed in claim 3, said kit having members in which the monomer (A) , the polymer (B) , the polymerization initiator composition (C) containing an organoboron compound and the polymerization inhibitor (D) are encased in two or more divided groups so that none of the two or more divided groups comprise the monomer (A) , the polymer (B) and the polymerization initiator composition (C). H:\EFHinIc veCi\NRPortbIDCCEFH\7006358_L do-19/12/2014 - 112

13. The adhesive kit for soft tissues, the adhesive agent kit for wound dressing or the wound dressing kit as claimed in claim 12, in which a mixture of the monomer (A) and the polymerization inhibitor (D) , the polymer (B) and the polymerization initiator composition (C) are each independently encased, and, when used, the mixture of the monomer (A) and the polymerization inhibitor (D) is first mixed with the polymerization initiator composition (C) containing an organoboron compound and subsequently mixed with the polymer (B).

14. The adhesive kit for soft tissues, the adhesive agent kit for wound dressing or the wound dressing kit as claimed in claim 10 or 11 including a jig for applying a composition obtained by mixing adhesive components or wound dressing components containing the components (A), (B) and (C).

15. The adhesive kit for soft tissues, the adhesive agent kit for wound dressing or the wound dressing kit as claimed in claim 12 or 13, including a jig for applying a composition obtained by mixing adhesive components or wound dressing components containing the components (A), (B), (C) and (D).

16. The adhesive kit for soft tissues, the adhesive agent kit for wound dressing or the wound dressing kit as claimed in claim 14 or 15, wherein the jig is at least one jig selected from a brush, a fiber ball, a cloth, a sponge ball and a piece of sponge. H \EFH\IlnenoenNRPorib]DCC\EFHU7 63S_I doc-19/12U2014 -113

17. The adhesive kit for soft tissues, the adhesive agent kit for wound dressing or the wound dressing kit as claimed in any one of claims 10 to 16, which further contains an aqueous solution for adhesion pretreatment containing 1 to 15% by weight of citric acid and 1 to 5% by weight of iron(III) chloride.