US2020108171A1PendingUtilityA1
Biocompatible Polycaprolactone Fumarate Formulations
Assignee: MAYO FOUND MEDICAL EDUCATION & RESPriority: Apr 8, 2011Filed: Sep 27, 2019Published: Apr 9, 2020
Est. expiryApr 8, 2031(~4.7 yrs left)· nominal 20-yr term from priority
A61L 27/18A61L 27/26C08G 63/08C08G 63/60
62
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Claims
Abstract
A polycaprolactone fumarate polymer useful as a matrix material for a biocompatible scaffold for tissue engineering applications is disclosed. The polycaprolactone fumarate polymer can be prepared by reacting caprolactone with an alkane polyol to prepare a polycaprolactone precursor, and then reacting the polycaprolactone precursor with fumaric acid or a salt thereof to prepare the polycaprolactone fumarate polymer. The use of an alkane diol, such as 1,2-propanediol, provides a linear polycaprolactone diol precursor. The use of an alkane triol, such as glycerol, provides a branched polycaprolactone triol precursor. The biocompatible polycaprolactone fumarate formulation releases no diethylene glycol or other undesirable byproducts during degradation.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A polymer having the Formula (I)
H-A 1 -B-A 2 -C-A 1 -B-A 2 -H (I)
wherein
A 1 is
A 2 is
B is —O—X—O— wherein X is selected from the group consisting of ethylene, trimethylene, tetramethylene, pentamethylene, C 1 -C 5 alkylethylene, C 1 -C 5 alkyltrimethylene, C 1 -C 5 alkyltetramethylene, and C 1 -C 5 alkylpentamethylene;
C is
and geometric isomers thereof; and
n is an integer from 1 to 50.
2 . The polymer of claim 1 wherein:
n is an integer from 1 to 20.
3 . The polymer of claim 1 wherein:
n is an integer from 1 to 10.
4 . The polymer of claim 1 wherein:
X is methylethylene.
5 . The polymer of claim 1 wherein the polymer has a number average molecular weight in the range of 5,000 to 15,000 g mol −1 .
6 . The polymer of claim 1 wherein the polymer has a polydispersity index in the range of 1 to 6.
7 . A crosslinkable, biodegradable material comprising:
the polymer of claim 1 ; and a free radical initiator.
8 . The material of claim 7 wherein:
the material does not include a crosslinking agent.
9 . A scaffold for tissue regeneration, the scaffold comprising:
a biodegradable matrix comprising the polymer of claim 1 .
10 . The scaffold of claim 9 wherein:
diethylene glycol is not released during hydrolysis of the scaffold.
11 . The scaffold of claim 9 wherein:
the scaffold maintains its geometrical structure and dimensions throughout an autoclave sterilization process.
12 . The scaffold of claim 9 wherein:
the scaffold maintains mechanical properties within an order of magnitude during an autoclave sterilization process.
13 . A polymer having the Formula (II)
wherein
A 1 is
A 2 is
A 3 is
B is —O—X—O— wherein X is selected from the group consisting of propanetriyl, butanetriyl, pentanetriyl, C 1 -C 5 alkyl propanetriyl, C 1 -C 5 alkyl butanetriyl, and C 1 -C 5 alkyl pentanetriyl;
C is
and geometric isomers thereof; and
n is an integer from 1 to 50.
14 . The polymer of claim 13 wherein:
n is an integer from 1 to 20.
15 . The polymer of claim 13 wherein:
n is an integer from 1 to 10.
16 . The polymer of claim 13 wherein:
X is propanetriyl.
17 . The polymer of claim 13 wherein the polymer has a number average molecular weight in the range of 5,000 to 15,000 g mol −1 .
18 . The polymer of claim 13 wherein the polymer has a polydispersity index in the range of 1 to 6.
19 . A crosslinkable, biodegradable material comprising:
the polymer of claim 13 ; and a free radical initiator.
20 . The material of claim 19 wherein:
the material does not include a crosslinking agent.
21 . A scaffold for tissue regeneration, the scaffold comprising:
a biodegradable matrix comprising the polymer of claim 13 .
22 . The scaffold of claim 21 wherein:
diethylene glycol is not released during hydrolysis of the scaffold.
23 . The scaffold of claim 21 wherein:
the scaffold maintains its geometrical structure and dimensions throughout an autoclave sterilization process.
24 . The scaffold of claim 21 wherein:
the scaffold maintains mechanical properties within an order of magnitude during an autoclave sterilization process.
25 . A polymer prepared by a process comprising:
(a) reacting caprolactone with an alkane polyol to prepare a polycaprolactone precursor; and (b) reacting the polycaprolactone precursor with fumaric acid or a salt thereof.
26 . The polymer of claim 25 wherein:
step (b) comprises reacting the polycaprolactone precursor with fumaryl chloride.
27 . The polymer of claim 25 wherein:
the alkane polyol is selected from the group consisting of C 2 -C 5 alkane diols.
28 . The polymer of claim 25 wherein:
the alkane polyol is selected from the group consisting of C 2 -C 5 alkane triols.
29 . The polymer of claim 25 wherein:
the alkane polyol is glycerol.
30 . The polymer of claim 25 wherein:
the polycaprolactone precursor has a number average molecular weight in the range of 1,000 to 5,000 g mol −1 .
31 . The polymer of claim 25 wherein:
the polymer is prepared by a process involving two separate reactions, wherein the polycaprolactone precursor is isolated.
32 . The polymer of claim 25 wherein:
both the polycaprolactone precursor and the polymer are prepared in one reaction vessel without isolation of the polycaprolactone precursor.Cited by (0)
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