Patent US6054504A successfully refreshed from Google Patents.
US6054504A
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US
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Biostatic coatings for the reduction and prevention of bacterial adhesion
Assignee: Hydromer Inc
•
Filing: 1997-12-31
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Granted: 2000-04-25
•
Expires: 2017-12-31
Abstract
Abstract The present invention relates to biostatic compositions, as well as coatings and methods for preparing biostatic articles using the same. The compositions contain a hydrophilic polymer possessing a functional group which covalently bonds to an amine, thiol, carboxyl, or hydroxyl active group of an antimicrobial agent. The functional group is capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of the antimicrobial agent below its capability of acting as a biostatic agent and without releasing the antimicrobial agent into a solution.
Inventors
- 👤 Joan M. Dalla Riva Toma
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 08:19
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/48; A01N43/54; A01N25/00; A01N25/08; A01N25/10; A01N25/24; C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10
Claims Analysis
Total Claims: 52
Claim 1
Independent Claim
105 words
A biostatic composition for reducing and preventing bacterial and microbial adhesion which comprises: (a) a hydrophilic polymer possessing a functional group which reacts with and covalently bonds to an active group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl, said functional group capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of said antimicrobial agent below its capability of acting as a biostatic agent and without releasing said antimicrobial agent into a solution; (b) an antimicrobial agent covalently bound to said functional group of said hydrophilic polymer; (c) a compatible polymer; and (d) a solvent.
Claim 2
Dependent Claim
105 words
A biostatic composition for reducing and preventing bacterial and microbial adhesion which comprises: (a) a hydrophilic polymer possessing a functional group which reacts with and covalently bonds to an active group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl, said functional group capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of said antimicrobial agent below its capability of acting as a biostatic agent and without releasing said antimicrobial agent into a solution; (b) an antimicrobial agent covalently bound to said functional group of said hydrophilic polymer; (c) a compatible polymer; and (d) a solvent.
Claim 3
Dependent Claim
43 words
The biostatic composition according to claim 1, wherein said functional group of said hydrophilic polymer is selected from the group consisting of isocyanates, isothiocyanates, esters, aldehydes, N-hydroxysuccinimide esters, epoxides, carboxylic esters, tresylates, anhydrides, alkyl halides, carboxylic acids, haloketones, alkenes, alkynes, and acyl chlorides.
Claim 4
Dependent Claim
26 words
The biostatic composition according to claim 1, wherein said hydrophilic polymer reacts with and covalently bonds to said antimicrobial agent to form a polymer-bound antimicrobial moiety.
Claim 5
Dependent Claim
50 words
The biostatic composition according to claim 1, wherein said hydrophilic polymer is selected from the group consisting of a polyurethane polymer, a maleic anhydride polymer, a maleic anhydride copolymer, a polyol, a polyamine, an acrylate polymer, an acrylate copolymer, an ethylene oxide modified polymer, and an ethylene oxide modified copolymer.
Claim 6
Dependent Claim
28 words
The biostatic composition according to claim 4, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyether polyol.
Claim 7
Dependent Claim
28 words
The biostatic composition according to claim 4, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyester polyol.
Claim 8
Dependent Claim
27 words
The biostatic composition according to claim 4, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyamine.
Claim 9
Dependent Claim
36 words
The biostatic composition according to claim 4, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyether polyol that has been modified with an antimicrobial agent.
Claim 10
Dependent Claim
36 words
The biostatic composition according to claim 4, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyester polyol that has been modified with an antimicrobial agent.
Claim 11
Dependent Claim
35 words
The biostatic composition according to claim 4, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyamine that has been modified with an antimicrobial agent.
Claim 12
Dependent Claim
26 words
The biostatic composition according to claim 1, wherein said antimicrobial agent has a reactive group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl.
Claim 13
Dependent Claim
25 words
The biostatic composition according to claim 1, wherein said antimicrobial is selected from the group consisting of 1,3-bis(1-methyl-3,5-dioxacyclohexyl)-5-amino-5-methylhexahydropyrimidine, 1,3-bis(1-methyl-3,5-dioxacyclohexyl)-5-amino-5-propylhexahydropyrimidine, 5-nitro-1,3-bis(1,3-diisopropyl)5-hydroxymethylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl)-5-hydroxymethylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl-5methylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl)-hexahydropyrimidine, and 5-nitro-1,3-bis(methyl)-5-hydroxymethylhexahydropyrimidine.
Claim 14
Dependent Claim
12 words
The biostatic composition according to claim 1, wherein said antimicrobial is 5-amino-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine.
Claim 15
Dependent Claim
59 words
The biostatic composition according to claim 1, wherein said compatible polymer is a homopolymer or copolymer derived from the group consisting of α-olefins, vinyl chlorides, vinylidene chlorides, ethyleneoxides, propyleneoxides, pyrrolidones, vinylpyrrolidones, hydroxyethylmethacrylates, methacrylates, polysaccharides, acrylamides, methacrylamides, peptides, proteins, nylons, silicone derivatives, acrylic acids, methacrylic acids, vinyl acetates, vinyl alcohols, vinyl ethers, celluloses, aromatic diisocyanates, aliphatic diisocyanates, and mixtures thereof.
Claim 16
Dependent Claim
48 words
The biostatic composition according to claim 1, wherein said solvent is selected from the group consisting of methyl ethyl ketones, N-methylpyrrolidinones, tetrahydrofurans, ethyl lactates, dichloromethanes, chloroforms, ethyl acetates, propylene glycol methyl ethers, propylene glycol methyl ether acetates, alcohols, ethers, esters, aromatics, chlorinated hydrocarbons, hydrocarbons, water and mixtures thereof.
Claim 17
Dependent Claim
50 words
The biostatic composition according to claim 1, further comprising at least one additive selected from the group consisting of chemically non-reactive antibiotics, chemically non-reactive antiseptics, chemically non-reactive antimicrobial agents, surfactants, metal complexes, anti-foam agents, pigments, visualization aids, dyes, lubricants, rheology modifiers, fragrances, plasticizers, anti-thrombogenic agents, bioeffecting agents, and mixtures thereof.
Claim 18
Dependent Claim
101 words
A coating for reducing and preventing bacterial and microbial adhesion which comprises: (a) a hydrophilic polymer possessing a functional group which reacts with and covalently bonds to an active group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl, said functional group capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of said antimicrobial agent below its capability of acting as a biostatic agent and without releasing said antimicrobial agent into a solution; (b) an anitmicrobial agent covalently bound to said functional group of said hydrophilic polymer; and (c) a compatible polymer.
Claim 19
Dependent Claim
101 words
A coating for reducing and preventing bacterial and microbial adhesion which comprises: (a) a hydrophilic polymer possessing a functional group which reacts with and covalently bonds to an active group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl, said functional group capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of said antimicrobial agent below its capability of acting as a biostatic agent and without releasing said antimicrobial agent into a solution; (b) an anitmicrobial agent covalently bound to said functional group of said hydrophilic polymer; and (c) a compatible polymer.
Claim 20
Dependent Claim
42 words
The coating according to claim 17, wherein said functional group of said hydrophilic polymer is selected from the group consisting of isocyanates, isothiocyanates, esters, aldehydes, N-hydroxysuccinimide esters, epoxides, carboxylic esters, tresylates, anhydrides, alkyl halides, carboxylic acids, haloketones, alkenes, alkynes, and acyl chlorides.
Claim 21
Dependent Claim
25 words
The coating according to claim 17, wherein said hydrophilic polymer reacts with and covalently bonds to said antimicrobial agent to form a polymer-bound antimicrobial moiety.
Claim 22
Dependent Claim
49 words
The coating according to claim 17, wherein said hydrophilic polymer is selected from the group consisting of a polyurethane polymer, a maleic anhydride polymer, a maleic anhydride copolymer, a polyol, a polyamine, an acrylate polymer, an acrylate copolymer, an ethylene oxide modified polymer, and an ethylene oxide modified copolymer.
Claim 23
Dependent Claim
27 words
The coating according to claim 20, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyether polyol.
Claim 24
Dependent Claim
27 words
The coating according to claim 20, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyester polyol.
Claim 25
Dependent Claim
26 words
The coating according to claim 20, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyamine.
Claim 26
Dependent Claim
35 words
The coating according to claim 20, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyether polyol that has been modified with an antimicrobial agent.
Claim 27
Dependent Claim
35 words
The coating according to claim 20, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyester polyol that has been modified with an antimicrobial agent.
Claim 28
Dependent Claim
34 words
The coating according to claim 20, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyamine that has been modified with an antimicrobial agent.
Claim 29
Dependent Claim
25 words
The coating according to claim 17, wherein said antimicrobial agent has a reactive group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl.
Claim 30
Dependent Claim
24 words
The coating according to claim 17, wherein said antimicrobial is selected from the group consisting of 1,3-bis(1-methyl-3,5-dioxa-cyclohexyl)-5amino-5-methylhexahydropyrimidine, 1,3-bis(1-methyl-3,5-dioxa-cyclohexyl)-5amino-5-propylhexahydropyrimidine, 5-nitro-1,3-bis(1,3-diisopropyl)-5-hydroxymethylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl)-5hydroxymethylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl-5-methylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl)-hexahydropyrimidine, and 5-nitro-1,3-bis(methyl)-5-hydroxymethylhexahydropyrimidine.
Claim 31
Dependent Claim
11 words
The coating according to claim 17, wherein said antimicrobial is 5amino-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine.
Claim 32
Dependent Claim
58 words
The coating according to claim 17, wherein said compatible polymer is a homopolymer or copolymer derived from the group consisting of α-olefins, vinyl chlorides, vinylidene chlorides, ethyleneoxides, propyleneoxides, pyrrolidones, vinylpyrrolidones, hydroxyethylmethacrylates, methacrylates, polysaccharides, acrylamides, methacrylamides, peptides, proteins, nylons, silicone derivatives, acrylic acids, methacrylic acids, vinyl acetates, vinyl alcohols, vinyl ethers, celluloses, aromatic diisocyanates, aliphatic diisocyanates, and mixtures thereof.
Claim 33
Dependent Claim
50 words
The coating according to claim 17, further comprising at least one additive selected from the group consisting of chemically non-reactive antibiotics, chemically non-reactive antiseptics, chemically non-reactive antimicrobial agents, anti-foam agents, pigments, visualization aids, fragrances, dyes, stabilizers, lubricants, rheology modifiers, surfactants, metal complexes, plasticizers, anti-thrombogenic agents, bioeffecting agents, and mixtures thereof.
Claim 34
Independent Claim
131 words
A method for preparing a biostatic article which comprises: (a) preparing a composition which comprises: (i) a hydrophilic polymer possessing a functional group which reacts with and covalently bonds to an active group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl, said functional group capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of said antimicrobial agent below its capability of acting as a biostatic agent and without releasing said antimicrobial agent into a solution; (ii) an antimicrobial agent covalently bound to said functional group of said hydrophilic polymer; (iii) a compatible polymer; and (iv) a solvent; (b) applying said composition to the surface of said article; (c) allowing said solvent of the composition to dry; and (d) curing said article.
Claim 35
Independent Claim
131 words
A method for preparing a biostatic article which comprises: (a) preparing a composition which comprises: (i) a hydrophilic polymer possessing a functional group which reacts with and covalently bonds to an active group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl, said functional group capable of reacting with and covalently bonding to an antimicrobial agent without effectively reducing antimicrobial property of said antimicrobial agent below its capability of acting as a biostatic agent and without releasing said antimicrobial agent into a solution; (ii) an antimicrobial agent covalently bound to said functional group of said hydrophilic polymer; (iii) a compatible polymer; and (iv) a solvent; (b) applying said composition to the surface of said article; (c) allowing said solvent of the composition to dry; and (d) curing said article.
Claim 36
Dependent Claim
13 words
The method according to claim 32, wherein said article is a medical device.
Claim 37
Dependent Claim
48 words
The method according to claim 32, wherein said medical device is selected from a group consisting of catheters, guidewires, gloves, contraceptives, wound dressings, drainage tubes, feeding tubes, myringotomy tubes, wound clips, implants, sutures, foams, ophthamalic lens, prostheses, blood bags, ultrafiltration or dialysis membranes, blood oxygenators, and vascular grafts.
Claim 38
Dependent Claim
42 words
The method according to claim 32, wherein said functional group of said hydrophilic polymer is selected from the group consisting of isocyanates, isothiocyanates, esters, aldehydes, N-hydroxysuccinimide esters, epoxides, carboxylic esters, tresylates, anhydrides, alkyl halides, carboxylic acids, haloketones, alkenes, alkynes, and acyl chlorides.
Claim 39
Dependent Claim
25 words
The method according to claim 32, wherein said hydrophilic polymer reacts with and covalently bonds to said antimicrobial agent to form a polymer-bound antimicrobial moiety.
Claim 40
Dependent Claim
49 words
The method according to claim 32, wherein said hydrophilic polymer is selected from the group consisting of a polyurethane polymer, a maleic anhydride polymer, a maleic anhydride copolymer, a polyol, a polyamine, an acrylate polymer, an acrylate copolymer, an ethylene oxide modified polymer, and an ethylene oxide modified copolymer.
Claim 41
Dependent Claim
27 words
The method according to claim 32, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyether polyol.
Claim 42
Dependent Claim
27 words
The method according to claim 37, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyester polyol.
Claim 43
Dependent Claim
26 words
The method according to claim 37, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyamine.
Claim 44
Dependent Claim
35 words
The method according to claim 37, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyether polyol that has been modified with an antimicrobial agent.
Claim 45
Dependent Claim
35 words
The method according to claim 37, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyester polyol that has been modified with an antimicrobial agent.
Claim 46
Dependent Claim
34 words
The method according to claim 37, wherein said polyurethane polymer is polyurethane polyisocyanate derived from reacting (i) an aromatic or aliphatic polyisocyanate with (ii) a polyamine that has been modified with an antimicrobial agent.
Claim 47
Dependent Claim
25 words
The method according to claim 32, wherein said antimicrobial agent having a reactive group selected from the group consisting of amine, thiol, carboxyl, and hydroxyl.
Claim 48
Dependent Claim
24 words
The method according to claim 32, wherein said antimicrobial is selected from the group consisting of 1,3-bis(1-methyl-3,5-dioxa-cyclohexyl)-5amino-5-methylhexahydropyrimidine, 1,3-bis(1-methyl-3,5-dioxa-cyclohexyl)-5-amino-5-propylhexahydropyrimidine, 5-nitro-1,3-bis(1,3-diisopropyl)-5-hydroxymethylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl)-5-hydroxymethylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl-5-methylhexahydropyrimidine, 5-amino-1,3-bis(1,3-diisopropyl)-hexahydropyrimidine, and 5-nitro-1,3-bis(methyl)-5-hydroxymethylhexahydropyrimidine.
Claim 49
Dependent Claim
11 words
The method according to claim 32, wherein said antimicrobial is 5-amino-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine.
Claim 50
Dependent Claim
58 words
The method according to claim 32, wherein said compatible polymer is a homopolymer or copolymer derived from the group consisting of α-olefins, vinyl chlorides, vinylidene chlorides, ethyleneoxides, propyleneoxides, pyrrolidones, vinylpyrrolidones, hydroxyethylmethacrylates, methacrylates, polysaccharides, acrylamides, methacrylamides, peptides, proteins, nylons, silicone derivatives, acrylic acids, methacrylic acids, vinyl acetates, vinyl alcohols, vinyl ethers, celluloses, aromatic diisocyanates, aliphatic diisocyanates, and mixtures thereof.
Claim 51
Dependent Claim
47 words
The method according to claim 32, wherein said solvent is selected from the group consisting of methyl ethyl ketones, N-methylpyrrolidinones, tetrahydrofurans, ethyl lactates, dichloromethanes, chloroforms, ethyl acetates, propylene glycol methyl ethers, propylene glycol methyl ether acetates, alcohols, ethers, esters, aromatics, chlorinated hydrocarbons, hydrocarbons, water and mixtures thereof.
Claim 52
Dependent Claim
50 words
The method according to claim 32, further comprising at least one additive selected from the group consisting of chemically non-reactive antibiotics, chemically non-reactive antiseptics, chemically non-reactive antimicrobial agents, anti-foam agents, pigments, visualization aids, lubricants, stabilizers, rheology modifiers, fragrances, dyes, surfactants, metal complexes, plasticizers, antithrombogenic agents, bioeffecting agents, and mixtures thereof.
References Cited (Backward Citations)
US4973493A
Cited
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