Pressure-sensitive adhesive compositions suitable for medical uses

Claim 2

An adhesive composition comprising a polymer adhesive that is soluble or dispersible in water and is low-temperature curable to form a solid which is single-phase at ambient temperature, pressure-sensitive, dermatologically acceptable, moisture vapor-permeable, and resistant to dissolution when exposed to water.

Claim 3

An adhesive composition as claimed in claim 1, wherein said adhesive, after curing, swells without dissolving when exposed to water.

Claim 4

An adhesive composition as claimed in claim 1, wherein said polymer adhesive is the product of a process comprising the step of subjecting a water-soluble derivatized capped prepolymer which comprises a plurality of first terminal groups and a plurality of low-temperature curable groups to chain extension in the presence of a chain extension agent reactive with said first terminal groups, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with said first terminal groups.

Claim 5

An adhesive composition as claimed in claim 3, wherein said derivatized capped prepolymer is reacted with an excess, based on the content of said first terminal group of said derivatized capped prepolymer, of said chain extension agent.

Claim 6

An adhesive composition as claimed in claim 3, wherein said first terminal group is an isocyanate group.

Claim 7

An adhesive composition as claimed in claim 5, wherein said chain extension agent is water, a polyol or a polyamine.

Claim 8

An adhesive composition as claimed in claim 3, wherein said first terminal group is an ester group.

Claim 9

An adhesive composition as claimed in claim 7, wherein said chain extension agent is ammonia or a polyamine.

Claim 10

An adhesive composition as claimed in claim 5, wherein said chain termination agent is ammonia.

Claim 11

An adhesive composition as claimed in claim 3, wherein said derivatized capped prepolymer is formed by reacting a water-soluble capped prepolymer comprising a plurality of said first terminal groups with a derivatizing agent comprising a first functional group which is reactive with said first terminal groups and a second functional group which is low-temperature curable, whereby a portion of said first terminal groups of said capped prepolymer are reacted with said first functional group of said derivatizing agent.

Claim 12

An adhesive composition as claimed in claim 10, wherein said second functional group is capable of low-temperature cure under the action of actinic radiation, pH shift or free radicals.

Claim 13

An adhesive composition as claimed in claim 11, wherein said second functional group is an ethylenically unsaturated group.

Claim 14

An adhesive composition as claimed in claim 10, wherein about 5 to 80% of said first terminal groups of said capped prepolymer are reacted with said first functional group of said derivatizing agent.

Claim 15

An adhesive composition as claimed in claim 13, wherein about 5 to 50% of said first terminal groups of said capped prepolymer are reacted with said first functional group of said derivatizing agent.

Claim 16

An adhesive composition as claimed in claim 10, wherein said first terminal group is an isocyanate group and said first functional group is a hydroxyl group or an amine group.

Claim 17

An adhesive composition as claimed in claim 15, wherein said derivatizing agent is a hydroxyalkyl acrylate, methacrylate, crotonate or itaconate.

Claim 18

An adhesive composition as claimed in claim 10, wherein said first terminal group is an ester group and said first functional group is an amine group.

Claim 19

An adhesive composition as claimed in claim 17, wherein said derivatizing agent is an aminoalkyl amide of a (C 1 -C 6 )-α,β-unsaturated carboxylic acid.

Claim 20

An adhesive composition as claimed in claim 3, wherein said derivatized capped prepolymer is formed by reacting a water-soluble prepolymer with one or more siloxane compounds comprising a low-temperature curable group.

Claim 21

An adhesive composition as claimed in claim 10, wherein said capped prepolymer is formed by reacting a water-soluble prepolymer comprising a plurality of a second terminal group which is reactive with said first terminal group, with a polyfunctional capping agent comprising a plurality of said first terminal group.

Claim 22

An adhesive composition as claimed in claim 20, wherein said first terminal group is an isocyanate group and said second terminal group is a hydroxyl group.

Claim 23

An adhesive composition as claimed in claim 21, wherein said prepolymer is a polyoxyalkylene polyol.

Claim 24

An adhesive composition as claimed in claim 20, wherein said first terminal group is an ester group and said second terminal group is an amine group.

Claim 25

An adhesive composition as claimed in claim 23, wherein said prepolymer is a polyaminoalkylene polyamine.

Claim 26

An adhesive composition as claimed in claim 20, wherein said prepolymer is formed by reacting a first water-soluble monomer comprising a plurality of said second terminal group with a second water-soluble monomer reactive with said second terminal group.

Claim 27

An adhesive composition as claimed in claim 25, wherein said second terminal group is a hydroxyl group.

Claim 28

An adhesive composition as claimed in claim 26, wherein said first water-soluble monomer is a polyol and said second water-soluble monomer is an epoxide compound.

Claim 29

An adhesive composition as claimed in claim 27, wherein said polyol is ethylene glycol, glycerol, trimethylolpropane or pentaerythritol.

Claim 30

An adhesive composition as claimed in claim 28, wherein said first water-soluble monomer is ethylene glycol, glycerol or a mixture of ethylene glycol and glycerol and said second water-soluble monomer is ethylene oxide.

Claim 31

An adhesive composition as claimed in claim 28, wherein said prepolymer has a molecular weight of about 3 to 15 kilodaltons.

Claim 32

An adhesive composition as claimed in claim 27, wherein said prepolymer is a copolymer which comprises at least 20% by weight of ethylene oxide moieties.

Claim 33

An adhesive composition as claimed in claim 25, wherein said second terminal group is an amine group.

Claim 34

An adhesive composition as claimed in claim 32, wherein said first water-soluble monomer is a polyamine and said second water-soluble monomer is an aziridene compound.

Claim 35

An adhesive composition as claimed in claim 20, wherein said prepolymer is a copolymer.

Claim 36

An adhesive composition as claimed in claim 34, wherein said copolymer comprises polyvinylpyrrolidone.

Claim 37

An adhesive composition as claimed in claim 1, wherein said polymer adhesive is the product of a process comprising the steps of i) reacting a compound comprising a plurality of hydroxyl groups and a polyisocyanate compound to form an isocyanate-terminated polyurethane capped prepolymer, ii) reacting a portion of the terminal isocyanate groups of said polyurethane capped prepolymer with a derivatizing agent comprising a group reactive with isocyanate and a low-temperature curable group to form a derivatized capped prepolymer, and iii) reacting said derivatized capped prepolymer with a chain extension agent reactive with isocyanate to effect chain extension of said derivatized capped prepolymer, whereby a polymer is formed, until said polymer attains a determined level of tackiness, wherein said chain extension is halted by addition of a chain termination agent reactive with isocyanate.

Claim 38

An adhesive composition as claimed in claim 1, further comprising a bioactive agent dissolved therein.

Claim 39

A adhesive composition as claimed in claim 37, wherein said bioactive agent is soluble in or miscible with water.

Claim 40

An adhesive composition as claimed in claim 37, wherein said bioactive agent is a protein, an enzyme, a growth factor, a hormone, a biocidal agent, an antiseptic agent, an antibacterial agent, an antifungal agent, an antiviral agent, an anti-histamine, an anti-inflammatory agent, an anti-pruritic agent, a keratolytic agent, an skin-protective agent, a rubefacient, a topical anesthetic, a hemostatic agent, an anti-anginal agent, a vitamin, a nutritional mineral, a water-soluble cellulose compound, collagen or nicotine.

Claim 41

A dermatologically-acceptable, moisture vapor-permeable, pressure-sensitive adhesive composition that is a single-phase solid at ambient temperature and resists dissolution when exposed to water, comprising a polymer adhesive which is the product of a process comprising the steps of i) providing a water-soluble derivatized capped prepolymer which comprises a first terminal group and a low-temperature curable group, ii) subjecting said water-soluble derivatized capped prepolymer to chain extension in the presence of a chain extension agent reactive with said first terminal group, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with said first terminal groups, and iii) subjecting said polymer to low-temperature curing.

Claim 42

A dermatologically-acceptable, moisture vapor-permeable, pressure-sensitive adhesive composition that is a single-phase solid at ambient temperature and resists dissolution when exposed to water, comprising a polymer adhesive which is the product of a process comprising the steps of i) providing a water-soluble derivatized capped prepolymer which comprises a first terminal group and a low-temperature curable group, ii) subjecting said water-soluble derivatized capped prepolymer to chain extension in the presence of a chain extension agent reactive with said first terminal group, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with said first terminal groups, and iii) subjecting said polymer to low-temperature curing.

Claim 43

An adhesive composition as claimed in claim 40, wherein in step iii, said low-temperature curing is effected by exposure to ultraviolet radiation or an electron beam.

Claim 44

An adhesive composition as claimed in claim 40, further comprising a bioactive agent dissolved therein.

Claim 45

An adhesive composition as claimed in soluble.

Claim 46

A water vapor-permeable, pressure-sensitive adhesive wound dressing, comprising a flexible backing coated with a pressure-sensitive adhesive layer provided on at least a portion of the surface of said backing, wherein said adhesive layer comprises an adhesive composition as claimed in claim 40.

Claim 47

A wound dressing as claimed in claim 44, wherein a bioactive agent is dissolved in said adhesive layer.

Claim 48

A wound dressing as claimed in claim 45, wherein said bioactive agent is water-soluble.

Claim 49

A wound dressing as claimed in claim 44, wherein said adhesive layer has moisture vapor permeability of about 6700 g/m 2 /24 hours.

Claim 50

A wound dressing as claimed in claim 44, wherein said flexible backing is a polyurethane film.

Claim 51

A process for producing a water vapor-permeable, pressure-sensitive adhesive wound dressing which comprises the steps of i) providing a flexible backing, ii) applying to at least a portion of the surface of said backing an adhesive composition as claimed in claim 3, and iii) subjecting said adhesive composition to low-temperature cure.

Claim 52

A process for producing a polymer adhesive that is soluble or dispersible in water and is low-temperature curable to form a solid which is single-phase at ambient temperature, pressure-sensitive, dermatologically acceptable, moisture vapor-permeable, and resistant to dissolution when exposed to water, which comprises the steps of i) providing a derivatized capped prepolymer comprising a plurality of first terminal groups, and ii) reacting said derivatized capped prepolymer with a chain extension agent reactive with said first terminal groups to effect chain extension of said derivatized capped prepolymer, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with said first terminal groups.

Claim 53

A process for producing a polymer adhesive that is soluble or dispersible in water and is low-temperature curable to form a solid which is single-phase at ambient temperature, pressure-sensitive, dermatologically acceptable, moisture vapor-permeable, and resistant to dissolution when exposed to water, which comprises the steps of i) providing a derivatized capped prepolymer comprising a plurality of first terminal groups, and ii) reacting said derivatized capped prepolymer with a chain extension agent reactive with said first terminal groups to effect chain extension of said derivatized capped prepolymer, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with said first terminal groups.

Claim 54

A process for producing a polymer adhesive that is soluble or dispersible in water and is low-temperature curable to form a solid which is single-phase at ambient temperature, pressure-sensitive, dermatologically acceptable, moisture vapor-permeable, and resistant to dissolution when exposed to water, which comprises the steps of i) reacting a compound comprising a plurality of hydroxyl groups and a polyisocyanate compound to form an isocyanate-terminated polyurethane capped prepolymer, ii) reacting a portion of the terminal isocyanate groups of said polyurethane capped prepolymer with a derivatizing agent comprising a group reactive with isocyanate and a low-temperature curable group to form a derivatized capped prepolymer, and iii) reacting said derivatized capped prepolymer with a chain extension agent reactive with isocyanate to effect chain extension of said derivatized capped prepolymer, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with isocyanate.

Claim 55

A process for producing a polymer adhesive that is soluble or dispersible in water and is low-temperature curable to form a solid which is single-phase at ambient temperature, pressure-sensitive, dermatologically acceptable, moisture vapor-permeable, and resistant to dissolution when exposed to water, which comprises the steps of i) reacting a compound comprising a plurality of hydroxyl groups and a polyisocyanate compound to form an isocyanate-terminated polyurethane capped prepolymer, ii) reacting a portion of the terminal isocyanate groups of said polyurethane capped prepolymer with a derivatizing agent comprising a group reactive with isocyanate and a low-temperature curable group to form a derivatized capped prepolymer, and iii) reacting said derivatized capped prepolymer with a chain extension agent reactive with isocyanate to effect chain extension of said derivatized capped prepolymer, whereby a polymer is formed, until said polymer attains a determined level of tackiness, when said chain extension is halted by addition of a chain termination agent reactive with isocyanate.

Claim 56

A process for producing a dermatologically-acceptable, moisture vapor-permeable, pressure-sensitive adhesive composition that is a single-phase solid at ambient temperature and resists dissolution when exposed to water, which comprises the step of subjecting a polymer adhesive produced by a process as claimed in claim 50 to low-temperature cure.

Claim 57

A process for producing a dermatologically-acceptable, moisture vapor-permeable, pressure-sensitive adhesive composition that is a single-phase solid at ambient temperature and resists dissolution when exposed to water, which comprises the step of subjecting a polymer adhesive produced by a process as claimed in claim 51 to low-temperature cure.