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US5496581A Expired / Lapsed US ⏱️ 0.0 years remaining

Polymeric coating

Assignee: Abbott Vascular Devices Ltd
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Filing: 1992-06-05
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Granted: 1996-03-05
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Expires: 2012-06-05
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Abstract

Abstract PCT No. PCT/GB92/01012 Sec. 371 Date Nov. 10, 1993 Sec. 102(e) Date Nov. 10, 1993 PCT Filed Jun. 5, 1992 PCT Pub. No. WO92/21386 PCT Pub. Date Dec. 10, 1992.A process for coating a surface comprising applying a solution containing a polymer obtained by polymerizing a phospholipid of the following formula (I): <IMAGE> (I)

Inventors

  • 👤 Yiannakis P. Yianni
  • 👤 Martin C. Wiles

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 10:14
CPC Classifications
C; C08; C08F; C08F38/00; A; A61; A61L; A61L29/00; A61L29/08; A61L29/085; A61L33/00; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/10

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 253 words
A process for coating a surface comprising applying to the surface a solution of a polymer, in an organic solvent and removing the solvent, wherein the polymer is obtained by polymerizing a phospholipid of formula (I): ##STR7## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other of B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms; wherein said polymer contains repeating units of the following formula (III) ##STR8## wherein one of Z 1 and Z 2 is Y 1 as defined above, and one of Z 3 and Z 4 are Y 1 as defined above, and wherein the other one of Z 1 and Z 2 and the other one of Z 3 and Z 4 are the formula --X 1 --(CO) p --G, wherein X 1 and p are as defined above, and G is a corresponding remaining portion of the phospholipid of formula (I).
Claim 2
Dependent Claim 253 words
A process for coating a surface comprising applying to the surface a solution of a polymer, in an organic solvent and removing the solvent, wherein the polymer is obtained by polymerizing a phospholipid of formula (I): ##STR7## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other of B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms; wherein said polymer contains repeating units of the following formula (III) ##STR8## wherein one of Z 1 and Z 2 is Y 1 as defined above, and one of Z 3 and Z 4 are Y 1 as defined above, and wherein the other one of Z 1 and Z 2 and the other one of Z 3 and Z 4 are the formula --X 1 --(CO) p --G, wherein X 1 and p are as defined above, and G is a corresponding remaining portion of the phospholipid of formula (I).
Claim 3
Dependent Claim 14 words
A process according to claim 1 in which the surface is a blood-contacting surface.
Claim 4
Dependent Claim 17 words
A process according to claim 1 in which the surface is subject to non-specific adsorption of protein.
Claim 5
Dependent Claim 27 words
A process according to claim 1, wherein in the phospholipid of formula (I), B 1 and B 2 are identical or different groups of the formula (II).
Claim 6
Dependent Claim 35 words
A process according to claim 1 wherein in the phospholipid of formula (I), each group B 1 and/or B 2 of formula (II) contains from 20 to 26 carbon atoms excluding any carbonyl carbon atoms.
Claim 7
Dependent Claim 39 words
A process according to claim 1 wherein in the phospholipid of formula (I), the number of carbon atoms in each X 1 is such that the di-yne will undergo both intramolecular and intermolecular polymerisation on exposure to actinic radiation.
Claim 8
Dependent Claim 32 words
A process according to claim 1 wherein in the phospholipid of formula (I) B 1 and B 2 each represent --CO--(CH.sub.2).sub.8 --C.tbd.C--C.tbd.C--Y.sup.1 wherein the groups Y 1 are the same or different.
Claim 9
Dependent Claim 21 words
A process according to claim 1 wherein in the phospholipid of formula (I) m is 2 and each R is methyl.
Claim 10
Dependent Claim 14 words
A process according to claim 1 wherein the phospholipid of formula (I) is: ##STR9##
Claim 11
Dependent Claim 14 words
A process according to claim 1 wherein the phospholipid of formula (I) is: ##STR10##
Claim 12
Dependent Claim 17 words
A process according to claim 1 wherein said solution also contains said phospholipid of said formula (I).
Claim 13
Dependent Claim 30 words
A process according to claim 1 wherein a mixture comprising a polymer obtained from a phospholipid of formula (I) and a diester of phosphatidyl choline is applied to the surface.
Claim 14
Dependent Claim 23 words
A process according to claim 12 wherein the diester of phosphatidyl choline is dipalmitoyl phosphatidyl choline, dimyristoyl phosphatidyl choline or distearoyl phosphatidyl choline.
Claim 15
Dependent Claim 24 words
A process according to claim 1 which comprises treating the surface to increase the hydrophobicity of the surface, prior to coating with the polymer.
Claim 16
Dependent Claim 30 words
A process according to claim 14 wherein said treating the surface is effected by a reactive alkyl silane or plasma polymerized in the presence of an alkane or alkyl silane.
Claim 17
Dependent Claim 28 words
A process according to claim 1 wherein the surface is coated with said solution of said polymer in a lower alkanol or halogenated alkane or a mixture thereof.
Claim 18
Dependent Claim 18 words
A process according to claim 1 wherein said solution comprises from 0.5 to 35 mg/ml of said polymer.
Claim 19
Dependent Claim 24 words
A process according to claim 1 wherein said solution is coated upon said surface by immersion in a coating bath, spraying, or spin coating.
Claim 20
Dependent Claim 18 words
A process according to claim 1 wherein the coating has a thickness of from 3 to 1000 nm.
Claim 21
Dependent Claim 218 words
A process for coating a surface comprising the steps of (a) treating said surface with a reactive alkyl silane or plasma polymerizing said surface in the presence of an alkane or alkylsilane, (b) after step (a) coating said surface with a solution of a polymer in a solvent selected from the group comprising lower alkanols, halogenated alkanes and mixtures thereof containing from 0.5 to 35 mg/ml of said polymer, by immersion in a coating bath, spraying, or spin coating and (c) removing said solvent, wherein said polymer is a phospholipid of formula (I) ##STR11## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms.
Claim 22
Dependent Claim 218 words
A process for coating a surface comprising the steps of (a) treating said surface with a reactive alkyl silane or plasma polymerizing said surface in the presence of an alkane or alkylsilane, (b) after step (a) coating said surface with a solution of a polymer in a solvent selected from the group comprising lower alkanols, halogenated alkanes and mixtures thereof containing from 0.5 to 35 mg/ml of said polymer, by immersion in a coating bath, spraying, or spin coating and (c) removing said solvent, wherein said polymer is a phospholipid of formula (I) ##STR11## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms.
Claim 23
Dependent Claim 22 words
The process according to claim 1 wherein said process forms a coating having a thickness of 10-500 nm by applying said solution.
Claim 24
Dependent Claim 307 words
A process for coating a surface comprising applying to said surface a solution of a polymer, in an organic solvent and then removing the solvent, wherein the polymer is obtained by polymerizing a phospholipid of formula (I): ##STR12## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other of B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms; wherein said polymer contains repeating units of the following formula (III): ##STR13## wherein one of Z 1 and Z 2 is Y 1 , and one of Z 3 and Z 4 are Y 1 , wherein the other one of Z 1 and Z 2 and the other one of Z 3 and Z 4 are the formula --X 1 --(CO) p --G, wherein X 1 and p are as defined above, and G is a corresponding remaining portion of the phospholipid of formula (I), wherein said solution comprises from 0.5 to 35 mg/ml of said polymer, wherein said process forms a coating having a thickness of from 3 to 1000 nm by application of said solution, wherein in said phospholipid of formula (I), B 1 and B 2 each represent --CO--(CH.sub.2).sub.8 --C.tbd.C--C.tbd.C--Y.sup.1 wherein the groups Y 1 are the same or different.
Claim 25
Dependent Claim 307 words
A process for coating a surface comprising applying to said surface a solution of a polymer, in an organic solvent and then removing the solvent, wherein the polymer is obtained by polymerizing a phospholipid of formula (I): ##STR12## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other of B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms; wherein said polymer contains repeating units of the following formula (III): ##STR13## wherein one of Z 1 and Z 2 is Y 1 , and one of Z 3 and Z 4 are Y 1 , wherein the other one of Z 1 and Z 2 and the other one of Z 3 and Z 4 are the formula --X 1 --(CO) p --G, wherein X 1 and p are as defined above, and G is a corresponding remaining portion of the phospholipid of formula (I), wherein said solution comprises from 0.5 to 35 mg/ml of said polymer, wherein said process forms a coating having a thickness of from 3 to 1000 nm by application of said solution, wherein in said phospholipid of formula (I), B 1 and B 2 each represent --CO--(CH.sub.2).sub.8 --C.tbd.C--C.tbd.C--Y.sup.1 wherein the groups Y 1 are the same or different.
Claim 26
Dependent Claim 24 words
The process according to claim 22 wherein said process forms a coating having a thickness of 10 to 500 nm by applying said solution.
Claim 27
Dependent Claim 264 words
A process for coating a surface comprising: pre-treating said surface by plasma polymerization, covering said surface with a coating comprising a polymer in a solution in an organic solvent, wherein said polymer is obtained by polymerizing a phospholipid of formula (I): ##STR14## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other of B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms; wherein said polymer contains repeating units of the following formula (III): ##STR15## wherein one of Z 1 and Z 2 are Y 1 as defined above, and one of Z 3 and Z 4 are Y 1 as defined above, and wherein the other one of Z 1 and Z 2 and the other one of Z 3 and Z 4 are the formula --X 1 --(CO) p --G, wherein X 1 and p are as defined above, and G is a corresponding remaining portion of the phospholipid of formula (I), and then removing said organic solvent.
Claim 28
Dependent Claim 264 words
A process for coating a surface comprising: pre-treating said surface by plasma polymerization, covering said surface with a coating comprising a polymer in a solution in an organic solvent, wherein said polymer is obtained by polymerizing a phospholipid of formula (I): ##STR14## wherein at least one of B 1 and B 2 is a group of the formula (II): --(CO).sub.p --X.sup.1 --C.tbd.C--C.tbd.C--Y.sup.1 (II) wherein p is 0 or 1, X 1 is an aliphatic or cycloaliphatic group, Y 1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X 1 and Y 1 in each B 1 and/or B 2 being 8 to 26, and the other of B 1 and B 2 is either (a) the same or a different group of the formula (II) or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms; wherein said polymer contains repeating units of the following formula (III): ##STR15## wherein one of Z 1 and Z 2 are Y 1 as defined above, and one of Z 3 and Z 4 are Y 1 as defined above, and wherein the other one of Z 1 and Z 2 and the other one of Z 3 and Z 4 are the formula --X 1 --(CO) p --G, wherein X 1 and p are as defined above, and G is a corresponding remaining portion of the phospholipid of formula (I), and then removing said organic solvent.

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