US6007833A
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Crosslinkable macromers bearing initiator groups
Assignee: Surmodics Coatings LLC
•
Filing: 1998-07-23
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Granted: 1999-12-28
•
Expires: 2018-07-23
Abstract
Abstract A crosslinkable macromer system that includes two or more polymer-pendent polymerizable groups and one or more polymer-pendent initiator groups. The polymerizable groups and the initiator group(s) can be pendent on the same or different polymeric backbones. The macromer system provides advantages over the use of polymerizable macromers and separate, low molecular weight initiators, including advantages with respect to such properties as nontoxicity, efficiency, and solubility.
Inventors
- 👤 Stephen J. Chudzik
- 👤 Aron B. Anderson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 13:55
CPC Classifications
C; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0072; A; A61; A61K; A61K38/00; A61K38/16; A61K38/17; A61K38/18; A61K38/1875; A61K9/00; A61K9/14; A61K9/16; A61K9/1605; A61K9/1629; A61K9/1641; A61K9/1647; A61L; A61L24/00; A61L24/001; A61L24/0031; A61L24/0042; A61L24/04; A61L24/046; A61L27/00; A61L27/28; A61L27/34; A61L29/00; A61L29/08; A61L29/085; A61L31/00; A61L31/14; A61L31/148; C08F; C08F251/00; C08F251/02; C08F290/00; C08L; C08L51/00; C08L51/02; A61K35/00; A61K35/12; A61K2035/126; A61K2035/128; A61K47/00; A61K47/30; A61K47/32; A61K47/34; A61K9/0012; A61K9/0019; A61K9/0024; Y; Y10; Y10S; Y10S522/00; Y10S522/904; Y10S522/905
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
374 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for iin vivo application, and wherein either: (a) the polymerizable groups and initiator group(s) are pendent on different polymers and the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, or (b) the polymerizable groups and the initiator group(s) are pendent on the same polymer and the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups; or (c) the polymerizable groups and the initiator group(s) are pendent on the same polymer and the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythirosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups.
Claim 2
Dependent Claim
374 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for iin vivo application, and wherein either: (a) the polymerizable groups and initiator group(s) are pendent on different polymers and the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, or (b) the polymerizable groups and the initiator group(s) are pendent on the same polymer and the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups; or (c) the polymerizable groups and the initiator group(s) are pendent on the same polymer and the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythirosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups.
Claim 3
Dependent Claim
24 words
A macromer system according to claim 1 wherein the pendent initiator groups are bonded to one or more monomers used to prepare the polymer.
Claim 4
Dependent Claim
18 words
A macromer system according to claim 1 wherein the pendent initiator groups are bonded to the polymer itself.
Claim 5
Dependent Claim
28 words
A macromer system according to claim 1 wherein the system comprises polymers bearing both initiator groups and polymerizable groups in combination with polymers providing only pendent polymerizable groups.
Claim 6
Dependent Claim
17 words
A macromer system according to claim 1 wherein photoinitiation occurs by means of a hydrogen abstraction reaction.
Claim 7
Dependent Claim
20 words
A macromer system according to claim 5 wherein the system further comprises one or more polymer-pendent energy transfer acceptor molecules.
Claim 8
Dependent Claim
21 words
A macromer system according to claim 6 wherein the energy transfer molecule is selected from the group consisting of tertiary amines.
Claim 9
Dependent Claim
25 words
A macromer system according to claim 1 wherein the groups are pendent upon polymers selected from the group consisting of synthetic polymers and naturally-occurring polymers.
Claim 10
Dependent Claim
22 words
A macromer system according to claim 8 wherein the polymer is selected from the group consisting of biodegradable polymers and biostable polymers.
Claim 11
Dependent Claim
30 words
A macromer system according to claim 9 wherein the polymer is selected from the group consisting of polymers adapted to form hydrogel matricies and polymers adapted to form non-hydrogel matrices.
Claim 12
Dependent Claim
19 words
A macromer system according to claim 10 wherein the polymer comprises a biodegradable polymer adapted to form hydrogel matrices.
Claim 13
Dependent Claim
24 words
A macromer system according to claim 11 wherein the polymer is a naturally-occurring polymer selected from the group consisting of polysaccharides and polyamino acids.
Claim 14
Dependent Claim
45 words
A macromer system according to claim 12 wherein the polysaccharides are selected from the group consisting of hyaluronic acid, starch, dextran, heparin, and chitosan, and the polyamino acids are selected from the group consisting of gelatin, collagen, fibronectin, laminin, albumin and active peptide domains thereof.
Claim 15
Dependent Claim
23 words
A macromer system according to claim 8 wherein the polymer comprises a synthetic polymer prepared via condensation polymerization of one or more monomers.
Claim 16
Dependent Claim
41 words
A macromer system according to claim 9 wherein the polymers are hydrophobic, biodegradable polymers selected from the group consisting of polylactides, polyglycolides, polycaprolactones, and copolymers of any combination of lactides, glycolides and caprolactones, and further consisting of polyanhydrides and polyortho esters.
Claim 17
Dependent Claim
27 words
A macromer system according to claim 9 wherein the polymers are biostable, hydrophilic polymers selected from the group consisting of polyvinylpyrrolidone, polyethylene glycol, polyacrylamide, and polyvinyl alcohol.
Claim 18
Dependent Claim
34 words
A macromer system according to claim 9 wherein the polymers are synthetic, biostable polymers formed by the polymerization of hydrophobic monomers selected from the group consisting of methyl methacrylate, butyl methacrylate, and dimethyl siloxanes.
Claim 19
Dependent Claim
18 words
A macromer system according to claim 1 wherein the polymers further comprise pendent reactive groups or affinity groups.
Claim 20
Dependent Claim
26 words
A macromer system according to claim 18 herein the reactive groups or affinity groups are adapted to bind to target groups on a surface of interest.
Claim 21
Dependent Claim
44 words
A method of forming a polymeric matrix adapted for in vivo application, the method comprising the steps of providing a macromer system according to claim 1, applying the system to a substrate, and cross-linking the system by free radical polymerization to form a matrix.
Claim 22
Dependent Claim
34 words
A method according to claim 20, wherein the in vivo application is selected from the group consisting of cellular encapsulation, adhesives/sealants, barriers, controlled release carriers, tissue replacement, wound dressing, and in situ device formation.
Claim 23
Dependent Claim
19 words
A method according to claim 20 wherein photoinitiation of the system occurs by means of a hydrogen abstraction reaction.
Claim 24
Dependent Claim
19 words
A method according to claim 22 wherein the system further comprises one or more polymer-pendent energy transfer acceptor molecules.
Claim 25
Dependent Claim
21 words
A method according to claim 23 wherein the energy transfer acceptor molecules are selected from the group consisting of tertiary amines.
Claim 26
Dependent Claim
21 words
A method according to claim 22 wherein photoinitiation results in the formation of covalent bonds between the matrix and the substrate.
Claim 27
Dependent Claim
36 words
A polymeric matrix adapted for in vivo application the matrix comprising a macromer system according to claim 1, the system having bean applied to a substrate and cross-linked by free radical polymerization to form a matrix.
Claim 28
Dependent Claim
34 words
A matrix according to claim 26, wherein the in vivo application is selected from the group consisting of cellular encapsulation, adhesives/sealants, barriers, controlled release carriers, tissue replacement, wound dressing, and in situ device formation.
Claim 29
Dependent Claim
19 words
A matrix according to claim 26 wherein photoinitiation of the system occurs by means of a hydrogen abstraction reaction.
Claim 30
Dependent Claim
19 words
A matrix according to claim 28 wherein the system further comprises one or more polymer-pendent energy transfer acceptor molecules.
Claim 31
Dependent Claim
21 words
A matrix according to claim 29 wherein the energy transfer acceptor molecules are selected from the group consisting of tertiary amines.
Claim 32
Dependent Claim
21 words
A matrix according to claim 28 wherein photoinitiation results in the formation of covalent bonds between the matrix and the substrate.
Claim 33
Dependent Claim
30 words
A macromer system according to claim 1 wherein the thioxanthones are selected from the group consisting of [(9-oxo-2-thioxanthanyl)-oxy]acetic acid and 2-hydroxy thioxanthone, and the benzoin ethers comprise vinyloxymethylbenzoin methyl ether.
Claim 34
Dependent Claim
29 words
A method according to claim 20 wherein the thioxanthones are selected from the group consisting of [(9-oxo-2-thioxanthanyl)-oxy]acetic acid and 2-hydroxy thioxanthone, and the benzoin ethers comprise vinyloxymethylbenzoin methyl ether.
Claim 35
Dependent Claim
30 words
A polymeric matrix according to claim 26 wherein the thioxanthones are selected from the group consisting of [(9-oxo-2-thioxanthanyl)-oxy]acetic acid and 2-hydroxy thioxanthone, and the benzoin ethers comprise vinyloxymethylbenzoin methyl ether.
Claim 36
Dependent Claim
73 words
A method of forming a polymeric matrix adapted for in vivo application, the method comprising the steps of providing a macromer system according to claim 1, applying the system to a substrate, and cross-linking the system by free radical polymerization to form a matrix, wherein photoinitiation of the system occurs by means of a hydrogen abstraction reaction, and wherein photoinitiation results in the formation of covalent bonds between the matrix and the substrate.
Claim 37
Dependent Claim
65 words
A polymeric matrix adapted for in vivo application, the matrix comprising a macromer system according to claim 1, the system having been applied to a substrate and cross-linked by free radical polymerization to form a matrix, wherein photoinitiation of the system occurs by means of a hydrogen abstraction reaction, and wherein photoinitiation results in the formation of covalent bonds between the matrix and the substrate.
Claim 38
Dependent Claim
73 words
A polymeric matrix adapted for in vivo application, the matrix comprising a macromer system according to claim 1, the system having been applied to a substrate and cross-linked by free radical polymerization to form a matrix, wherein photoinitiation of the system occurs by means of a hydrogen abstraction reaction, and wherein the thioxanthones are selected from the group consisting of [(9-oxo-2-thioxanthanyl)-oxy]acetic acid and 2-hydroxy thioxanthone, and the benzoin ethers comprise vinyloxymethylbenzoin methyl ether.
Claim 39
Dependent Claim
156 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the system comprises polymers bearing both initiator groups and polymerizable groups in combination with polymers providing only pendent polymerizable groups.
Claim 40
Dependent Claim
156 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the system comprises polymers bearing both initiator groups and polymerizable groups in combination with polymers providing only pendent polymerizable groups.
Claim 41
Dependent Claim
148 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the groups are pendent upon biodegradable polymers adapted to form hydrogel matrices.
Claim 42
Dependent Claim
148 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the groups are pendent upon biodegradable polymers adapted to form hydrogel matrices.
Claim 43
Dependent Claim
24 words
A macromer system according to claim 39 wherein the polymer is a naturally-occurring polymer selected from the group consisting of polysaccharides and polyamino acids.
Claim 44
Dependent Claim
45 words
A macromer system according to claim 40 wherein the polysaccharides are selected from the group consisting of hyaluronic acid, starch, dextran, heparin, and chitosan, and the polyamino acids are selected from the group consisting of gelatin, collagen, fibronectin, laminin, albumin and active peptide domains thereof.
Claim 45
Dependent Claim
151 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the polymer comprises a synthetic polymer prepared via condensation polymerization of one or more monomers.
Claim 46
Dependent Claim
151 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the polymer comprises a synthetic polymer prepared via condensation polymerization of one or more monomers.
Claim 47
Dependent Claim
41 words
A macromer system according to claim 42 wherein the polymers are hydrophobic, biodegradable polymers selected from the group consisting of polylactides, polyglycolides, polycaprolactones, and copolymers of any combination of lactides, glycolides and caprolactones, and further consisting of polyanhydrides and polyortho esters.
Claim 48
Dependent Claim
166 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the polymers further comprise pendent reactive groups or affinity groups, and wherein the reactive groups or affinity groups are adapted to bind to target groups on a surface of interest.
Claim 49
Dependent Claim
166 words
A crosslinkable macromer system comprising one or more polymers providing pendent polymerizable and pendent initiator groups wherein the system is adapted to be polymerized in order to form a matrix suitable for in vivo application, and wherein the initiator groups are independently selected from the group consisting of long wave ultraviolet activatable molecules selected from the group consisting of benzophenone, thioxanthones, and benzoin ethers; visible light activatable molecules selected from the group consisting of ethyl eosin, eosin Y, rose bengal, camphorquinone and erythrosin; and thermally activatable molecules selected from the group consisting of 4,4' azobis(4-cyanopentanoic) acid, and 2,2-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride, and benzoyl peroxide; and the pendent polymerizable groups are selected from the group consisting of vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups, wherein the polymers further comprise pendent reactive groups or affinity groups, and wherein the reactive groups or affinity groups are adapted to bind to target groups on a surface of interest.
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