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US4626310A Expired / Lapsed US ⏱️ 0.0 years remaining

Surgical adhesive systems for hard body tissues

Assignee: Henkel AG and Co KGaA
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Filing: 1985-05-10
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Granted: 1986-12-02
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Expires: 2005-05-10
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Abstract

Abstract Surgical adhesive systems for the bonding of hard body tissues which contain as a polymerization initiating starter an organoboron compound and a resorbable (meth)acrylate component which is liquid to solid at room temperature and which consists of (meth)-acrylic acid esters with (meth)-acrylate groups on polyester oligomer chains from hydroxycarboxylic acids, preferably having 2 (meth)-acrylate groups in the alpha , omega positions on the oligomer chains, and wherein the polyester oligomers are preferably formed from monohydroxymonocarboxylic acids.

Inventors

  • 👤 Wolfgang Ritter

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 12:27
CPC Classifications
C; C08; C08F; C08F299/00; C08F299/02; C08F299/04; A; A61; A61L; A61L27/00; A61L27/14; A61L27/16

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 94 words
A method of bonding hard body tissues to each other or to a metal or to a synthetic material comprising the steps of: (A) applying to one or both surfaces to be joined together a surgical bonding system comprising: (a) a polymerization initiating starter component which contains at least one organoboron compound; and (b) a polymerizable adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having more than one (meth)-acrylate group on a polyester oligomer chain that contains hydroxy-carboxylic acid segments; and (B) joining together said surfaces.
Claim 2
Independent Claim 94 words
A method of bonding hard body tissues to each other or to a metal or to a synthetic material comprising the steps of: (A) applying to one or both surfaces to be joined together a surgical bonding system comprising: (a) a polymerization initiating starter component which contains at least one organoboron compound; and (b) a polymerizable adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having more than one (meth)-acrylate group on a polyester oligomer chain that contains hydroxy-carboxylic acid segments; and (B) joining together said surfaces.
Claim 3
Dependent Claim 17 words
A method in accordance with claim 1 wherein components (a) and (b) are mixed together before application.
Claim 4
Dependent Claim 41 words
A method in accordance with claim 1 wherein component (a) is applied first to at least one of the surfaces to be joined together and thereafter component (b) is applied to at least one of the surfaces to be joined together.
Claim 5
Dependent Claim 14 words
A method in accordance with claim 1 wherein the hard body tissues are bones.
Claim 6
Dependent Claim 64 words
A two-component surgical bonding system for the bonding of hard body tissues which comprises (a) a polymerization initiating starter component which contains at least one organoboron compound; and (b) a polymerization adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having more than one (meth) acrylate group on a polyester oligomer chain that contains hydroxycarboxylic acid segments.
Claim 7
Dependent Claim 64 words
A two-component surgical bonding system for the bonding of hard body tissues which comprises (a) a polymerization initiating starter component which contains at least one organoboron compound; and (b) a polymerization adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having more than one (meth) acrylate group on a polyester oligomer chain that contains hydroxycarboxylic acid segments.
Claim 8
Dependent Claim 30 words
A surgical bonding system in accordance with claim 5 wherein at least one (meth)-acrylate group in the resorbable (meth)-acrylate compound is on a terminal position of the polyester oligomer chain.
Claim 9
Dependent Claim 31 words
A surgical bonding system in accordance with claim 5 wherein the resorbable (meth)-acrylate compound contains a (meth)-acrylate group in both the α and the ω position of the polyester oligomer chain.
Claim 10
Dependent Claim 31 words
A surgical bonding system in accordance with claim 5 wherein each hydroxycarboxylic acid segment in the polyester oligomer chain of the resorbable (meth)-acrylate compound contains from 2 to 10 carbon atoms.
Claim 11
Dependent Claim 21 words
A surgical bonding system in accordance with claim 5 wherein each hydroxycarboxylic acid segment contains from 2 to 6 carbon atoms.
Claim 12
Dependent Claim 35 words
A surgical bonding system in accordance with claim 8 wherein the hydroxycarboxylic acid segments are formed from at least one of the following acids: glycolic acid, lactic acid, hydroxypropionic acid, hydroxybutyric acid, and hydroxybenzoic acid.
Claim 13
Dependent Claim 33 words
A surgical bonding system in accordance with claim 5 wherein the polyester oligomer chain in the resorbable (meth)-acrylate compound has a mean molecular weight in the range of about 200 to about 600.
Claim 14
Dependent Claim 28 words
A surgical bonding system in accordance with claim 11 wherein the polyester oligomer chain has a mean molecular weight in the range of about 300 to about 500.
Claim 15
Dependent Claim 38 words
A surgical bonding system in accordance with claim 5 wherein the resorbable (meth)-acrylate compound also contains at least one moiety derived from the following: a difunctional alcohol, and a difunctional carboxylic acid or a functionally reactive derivative thereof.
Claim 16
Dependent Claim 66 words
A surgical bonding system in accordance with claim 13 wherein a mixture of a monofunctional compound and a difunctional compound is employed in the formation of the (meth)-acrylate compound, and wherein the monofunctional compound is used in quantities not over 50 mole percent of said mixture said monofunctional compound being a monofunctional alcohol, a monofunctional carboxylic acid or functionally reactive derivative thereof, or a monofunctional amine.
Claim 17
Dependent Claim 25 words
A surgical bonding system in accordance with claim 14 wherein the monofunctional compound is used in quantities not over 10 mole percent of said mixture.
Claim 18
Dependent Claim 28 words
A surgical bonding system in accordance with claim 5 wherein the resorbable (meth)-acrylate compound has a viscosity at room temperature of from about 2000 to about 70,000 mPas.
Claim 19
Dependent Claim 23 words
A surgical bonding system in accordance with claim 16 wherein the viscosity at room temperature is from about 3,000 to about 50,000 mPas.
Claim 20
Dependent Claim 38 words
A surgical bonding system in accordance with claim 5 wherein the starter component (a) does not self-ignite when exposed to air yet will initiate polymerization of polymerizable adhesive component (b) at mammalian body temperatures when exposed to air.
Claim 21
Dependent Claim 44 words
A surgical bonding system in accordance with claim 18 wherein the organoboron compound in starter component (a) contains at least one substituent group selected from the group consisting of alkyl and aryl groups, and which can also optionally contain at least one B-H bond.
Claim 22
Dependent Claim 37 words
A surgical bonding system in accordance with claim 19 wherein the starter component (a) contains at least one alkyl boron compound selected from the group consisting of a trialkyl boron compound and an alkyl boron hydride compound.
Claim 23
Dependent Claim 123 words
A surgical bonding system in accordance with claim 5 wherein polymerization initiating starter component (a) contains at least one of the following: (i) a homogeneous mixture of an organic oligomer or polymer, and at least one organoboron compound which is activated by exposure to air and is compatible with polymerizable adhesive component (b) and is inert toward the organic oligomer or polymer; (ii) at least one polymeric organoboron compound which has, on a stable polymer matrix, boron hydride groups or organoboron groups, or a mixture of such groups, which are stable in the presence of oxygen; and (iii) at least one boronalkyl compound which contains boron hydride groups, or organoboron groups, or a combination thereof, on a fatty acid or fatty alcohol ester.
Claim 24
Dependent Claim 31 words
A surgical bonding system in accordance with claim 21 wherein in the homogeneous mixture in (i) the organic oligomer or polymer is a polymer based on a derivative of (meth)-acrylic acid.
Claim 25
Dependent Claim 21 words
A surgical bonding system in accordance with claim 22 wherein the derivative of (meth)-acrylic acid is an ester or amide thereof.
Claim 26
Dependent Claim 78 words
A two component surgical bonding system for the bonding of hard body tissues which comprises (a) a polymerization initiating starter component which contains at least one organoboron compound; and (b) a polymerization adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having a (meth)-acrylate group on a polyester oligomer chain that contains hydroxycarboxylic acid segments and which also contains a moiety derived from a monocarboxylic acid or functionally reactive derivative thereof.
Claim 27
Dependent Claim 78 words
A two component surgical bonding system for the bonding of hard body tissues which comprises (a) a polymerization initiating starter component which contains at least one organoboron compound; and (b) a polymerization adhesive component which contains at least one resorbable (meth)-acrylate compound which is a (meth)-acrylic acid ester having a (meth)-acrylate group on a polyester oligomer chain that contains hydroxycarboxylic acid segments and which also contains a moiety derived from a monocarboxylic acid or functionally reactive derivative thereof.
Claim 28
Dependent Claim 36 words
A two component surgical bonding system in accordance with claim 24 wherein the (meth)-acrylate group is obtained by reaction of the terminal carboxy group of the polyester oligomer chain with the glycidyl ester of (meth)-acrylic acid.

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-12-01 1990-06-02 1990-12-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-12-01 1994-06-02 1994-12-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-12-01 1998-06-02 1998-12-02 $7700.00 Window Closed / Lapsed

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