US2008064845A9PendingUtilityA9
Compounds containing quaternary carbons, medical devices, and methods
Est. expiryNov 14, 2021(expired)· nominal 20-yr term from priority
Inventors:Michael Eric BenzEdward DidomenicoChristopher M. HobotRandall V. SparerKenneth B. WagenerJohn E. Schwendeman
C08F 236/20C08G 18/6204A61L 27/18
52
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Claims
Abstract
Compounds that include diorgano groups having quaternary carbons and optionally urethane groups, urea groups, or combinations thereof (i.e., polyurethanes, polyureas, or polyurethane-ureas), as well as materials and methods for making such compounds.
Claims
exact text as granted — not AI-modified1 . A medical device comprising a polymer comprising a group of the formula:
—(R 1 ) n -(-Z-(R 2 ) m —) p —
wherein:
n=0 or 1;
m=0 or 1;
p=1-100,000;
R 1 and R 2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, with the proviso that R 2 includes at least two carbon atoms; and
Z is —C(R 3 ) 2 — wherein each R 3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring.
2 . The medical device of claim 1 wherein p=1-5000.
3 . The medical device of claim 2 wherein p=2-12.
4 . The medical device of claim 1 wherein R 1 and R 2 are each independently a straight chain alkylene group, an arylene group, or combinations thereof.
5 . The medical device of claim 4 wherein R 1 and R 2 are each independently a straight chain alkylene group.
6 . The medical device of claim 1 wherein R 1 and R 2 are each independently groups containing up to 100 carbon atoms.
7 . The medical device of claim 6 wherein R 1 and R 2 are each independently groups containing up to 20 carbon atoms.
8 . The medical device of claim 7 wherein R 1 and R 2 are each independently groups containing 2 to 20 carbon atoms.
9 . The medical device of claim 1 wherein each R 3 is independently a straight chain alkyl group, an aryl group, or combinations thereof, optionally including heteroatoms.
10 . The medical device of claim 9 wherein each R 3 is independently a straight chain alkyl group, optionally including heteroatoms.
11 . The medical device of claim 10 wherein each R 3 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
12 . The medical device of claim 1 wherein the polymer further comprises a urethane group, a urea group, or combinations thereof.
13 . The medical device of claim 12 wherein the polymer comprises a segmented polyurethane.
14 . The medical device of claim 1 wherein the polymer is a biomaterial.
15 . The medical device of claim 14 wherein the polymer is substantially free of ether, ester, and carbonate linkages.
16 . The medical device of claim 1 wherein the polymer is linear, branched, or crosslinked.
17 . A medical device comprising a polymer prepared from a compound of the formula:
Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y
wherein:
each Y is independently OH or NR 4 H;
n=0 or 1;
m=0 or 1;
p=1-2000;
R 1 and R 2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
Z is —C(R 3 ) 2 — wherein each R 3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring; and
each R 4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof; with the proviso that at least one of the repeat units -Z-(R 2 ) m — is not a —C(CH 3 ) 2 CH 2 — group when both Y groups are OH.
18 . The medical device of claim 17 wherein p=1-100.
19 . The medical device of claim 18 wherein p=2-12.
20 . The medical device of claim 17 wherein the number average molecular weight of the compound of the formula Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y is no greater than about 100,000.
21 . The medical device of claim 20 wherein the number average molecular weight of the compound of the formula Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y is about 1000 to about 1500.
22 . The medical device of claim 17 wherein R 1 and R 2 are each independently a straight chain alkylene group, an arylene group, or combinations thereof.
23 . The medical device of claim 22 wherein R 1 and R 2 are each independently a straight chain alkylene group.
24 . The medical device of claim 17 wherein R 1 and R 2 are each independently groups containing up to 100 carbon atoms.
25 . The medical device of claim 24 wherein R 1 and R 2 are each independently groups containing up to 20 carbon atoms.
26 . The medical device of claim 25 wherein R 1 and R 2 are each independently groups containing 2 to 20 carbon atoms.
27 . The medical device of claim 17 wherein each R 2 includes at least two carbon atoms.
28 . The medical device of claim 17 wherein each R 3 is independently a straight chain alkyl group, an aryl group, or combinations thereof, optionally including heteroatoms.
29 . The medical device of claim 28 wherein each R 3 is independently a straight chain alkyl group, optionally including heteroatoms.
30 . The medical device of claim 29 wherein each R 3 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
31 . The medical device of claim 17 wherein the polymer further comprises a urethane group, a urea group, or combinations thereof.
32 . The medical device of claim 31 wherein the polymer comprises a segmented polyurethane.
33 . The medical device of claim 17 wherein the polymer is a biomaterial.
34 . The medical device of claim 33 wherein the polymer is substantially free of ether, ester, and carbonate linkages.
35 . The medical device of claim 17 wherein each Y is OH.
36 . The medical device of claim 17 wherein each R 4 is independently H or a straight chain alkyl group.
37 . The medical device of claim 36 wherein each R 4 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
38 . The medical device of claim 36 wherein each R 4 is H.
39 . The medical device of claim 17 wherein the polymer is linear, branched, or crosslinked.
40 - 44 . (canceled)
45 . A copolymer comprising a group of the formula:
—(R 1 ) n -(-Z-(R 2 ) m —) p —
wherein:
n=0 or 1;
m=0 or 1;
p=1-100,000;
R 1 and R 2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, with the proviso that R 2 includes at least two carbon atoms; and
Z is —C(R 3 ) 2 — wherein each R 3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring.
46 . The copolymer of claim 45 wherein p=1-5000.
47 . The copolymer of claim 46 wherein p=2-12.
48 . The copolymer of claim 45 wherein R 1 and R 2 are each independently a straight chain alkylene group, an arylene group, or combinations thereof.
49 . The copolymer of claim 48 wherein R 1 and R 2 are each independently a straight chain alkylene group.
50 . The copolymer of claim 45 wherein R 1 and R 2 are each independently groups containing 2 to 20 carbon atoms.
51 . The copolymer of claim 45 wherein each R 3 is independently a straight chain alkyl group, an aryl group, or combinations thereof, optionally including heteroatoms.
52 . The copolymer of claim 51 wherein each R 3 is independently a straight chain alkyl group, optionally including heteroatoms.
53 . The copolymer of claim 52 wherein each R 3 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
54 . The copolymer of claim 45 wherein the coplymer is linear, branched, or crosslinked.
55 - 61 . (canceled)
62 . A copolymer prepared from a compound of the formula:
Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y
wherein:
each Y is independently OH or NR 4 H;
n=0 or 1;
m=0 or 1;
p=1-2000;
R 1 and R 2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
Z is —C(R 3 ) 2 — wherein each R 3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring; and
each R 4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
with the proviso that at least one of the repeat units -Z-(R 2 ) m — is not a —C(CH 3 ) 2 CH 2 — group when both Y groups are OH.
63 . The copolymer of claim 62 wherein p=1-100.
64 . The copolymer of claim 63 wherein p=2-12.
65 . The copolymer of claim 62 wherein the number average molecular weight of the compound of the formula Y—(R 1 ) n —(-Z-(R 2 ) m —) p —Y is no greater than about 100,000.
66 . The copolymer of claim 62 wherein R 1 and R 2 are each independently a straight chain alkylene group, an arylene group, or combinations thereof.
67 . The copolymer of claim 66 wherein R 1 and R 2 are each independently groups containing up to 100 carbon atoms.
68 . The copolymer of claim 67 wherein R 1 and R 2 are each independently groups containing up to 20 carbon atoms.
69 . The copolymer of claim 68 wherein R 1 and R 2 are each independently groups containing 2 to 20 carbon atoms.
70 . The copolymer of claim 62 wherein each R 2 includes at least two carbon atoms.
71 . The copolymer of claim 62 wherein each R 3 is independently a straight chain alkyl group, an aryl group, or combinations thereof, optionally including heteroatoms.
72 . The copolymer of claim 71 wherein each R 3 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
73 . The copolymer of claim 62 wherein each Y is OH.
74 . The copolymer of claim 62 wherein each R 4 is independently H or a straight chain alkyl group.
75 . The copolymer of claim 62 wherein the copolymer is linear, branched, or crosslinked.
76 - 87 . (canceled)
88 . A copolymer prepared from a compound of the formula:
Y—R 5 —(—R 6 -Z-R 7 —) q —R 8 —Y
wherein:
each Y is independently OH or NH 2 ;
q=1-2000;
Z is —C(R 9 ) 2 —;
R 5 , R 6 , R 7 , and R 8 are each independently a straight chain alkylene group having 1-20 carbon atoms; and
each R 9 is independently a straight chain alkyl group having 1-20 carbon atoms.
89 . The copolymer of claim 88 wherein q=1-100.
90 . The copolymer of claim 89 wherein q=2-12.
91 . The copolymer of claim 88 wherein each Y is OH.
92 . The copolymer of claim 91 wherein each R 9 is methyl.
93 . A compound of the formula:
Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y
wherein:
each Y is independently OH, NR 4 H, or protected forms thereof;
n=0 or 1;
m=0 or 1;
p=1-2000;
R 1 and R 2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
Z is —C(R 3 ) 2 — wherein each R 3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring; and
each R 4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof;
with the proviso that at least one of the repeat units -Z-(R 2 ) m — is not a —C(CH 3 ) 2 CH 2 — group when both Y groups are OH.
94 . The compound of claim 93 wherein p=1-100.
95 . The compound of claim 94 wherein p=2-12.
96 . The compound of claim 93 wherein the number average molecular weight of the compound of the formula Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y is no greater than about 100,000.
97 . The compound of claim 93 wherein R 1 and R 2 are each independently a straight chain alkylene group, an arylene group, or combinations thereof.
98 . The compound of claim 93 wherein R 1 and R 2 are each independently groups containing up to 100 carbon atoms.
99 . The compound of claim 98 wherein R 1 and R 2 are each independently groups containing 2 to 20 carbon atoms.
100 . The compound of claim 93 wherein each R 2 includes at least two carbon atoms.
101 . The compound of claim 93 wherein each R 3 is independently a straight chain alkyl group, an aryl group, or combinations thereof, optionally including heteroatoms.
102 . The compound of claim 101 wherein each R 3 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
103 . The compound of claim 93 wherein each Y is OH.
104 . The compound of claim 93 wherein each R 4 is independently a straight chain alkyl group containing 1 to 20 carbon atoms.
105 . The compound of claim 93 wherein each R 4 is H.
106 . A compound of the formula:
Y—R 5 —(—R 6 -Z-R 7 —) q —R 8 —Y
wherein:
each Y is independently OH, NH 2 , or protected forms thereof;
q=1-2000;
Z is —C(R 9 ) 2 —;
R 5 , R 6 , R 7 , and R 8 are each independently a straight chain alkylene group having 1-20 carbon atoms; and
each R 9 is independently a straight chain alkyl group having 1-20 carbon atoms.
107 . The compound of claim 106 wherein q=1-100.
108 . The compound of claim 107 wherein q=2-12.
109 . The compound of claim 106 wherein each Y is OH.
110 . The compound of claim 109 wherein each R 9 is methyl.
111 - 116 . (canceled)
117 . A method of making a compound of the formula:
Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y
wherein:
each Y is independently OH or NR 4 H;
n=0 or 1;
m=0 or 1;
p=1-2000;
R 1 and R 2 are each independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
Z is —C(R 3 ) 2 — wherein each R 3 is independently a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring; and
each R 4 is independently H or a saturated or unsaturated aliphatic group, an aromatic group, or combinations thereof,
with the proviso that at least one of the repeat units -Z-(R 2 ) m — is not a —C(CH 3 ) 2 CH 2 — group when both Y groups are OH;
the method comprising:
polymerizing a diene compound having a quaternary carbon in the presence of a metathesis catalyst to form an intermediate polymer;
depolymerizing the intermediate polymer in the presence of a chain transfer agent to form an unsaturated telechelic polymer; wherein the chain transfer agent comprises protecting groups; and
converting the unsaturated telechelic polymer to a compound of the formula Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y.
118 . The method of claim 117 wherein converting the unsaturated telechelic polymer to a compound of the formula Y—(R 1 ) n -(-Z-(R 2 ) m ) p —Y comprises:
hydrogenating the unsaturated telechelic polymer to form a saturated telechelic polymer; and deprotecting the saturated telechelic polymer.
119 . The method of claim 117 wherein converting the unsaturated telechelic polymer to a compound of the formula Y—(R 1 ) n -(-Z-(R 2 ) m —) p —Y comprises:
deprotecting the unsaturated telechelic polymer; and hydrogenating the unsaturated telechelic polymer to form a saturated telechelic polymer.
120 . The method of claim 117 wherein polymerizing the diene compound comprises polymerizing the diene compound in the presence of a chain extender and a metathesis catalyst to form an intermediate polymer.
121 . A method of making an alcohol and/or an amine comprising a quaternary carbon, the method comprising:
polymerizing a compound having a quaternary carbon in the presence of a metathesis catalyst to form an intermediate polymer, wherein the compound having a quaternary carbon has the formula: R 10 HC═CH—(R 11 ) r -Z-(R 12 ) s —CH═CHR 13 wherein:
r=0 or 1;
s=0 or 1;
Z is —C(R 3 ) 2 —, wherein each R 3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring;
R 10 and R 13 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms; and
R 11 and R 12 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms; depolymerizing the intermediate polymer in the presence of a chain transfer agent to form an unsaturated telechelic polymer; wherein the chain transfer agent comprises protecting groups and has the formula: Y—R 17 —HC═CH—R 18 —Y wherein:
each Y is independently a protected form of OH or NR 4 H; and
R 17 and R 18 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof; and
converting the unsaturated telechelic polymer to an alcohol and/or an amine.
122 . The method of claim 121 wherein converting the unsaturated telechelic polymer to an alcohol and/or an amine comprises:
hydrogenating the unsaturated telechelic polymer to form a saturated telechelic polymer; and deprotecting the saturated telechelic polymer.
123 . The method of claim 121 wherein converting the unsaturated telechelic polymer to an alcohol and/or an amine comprises:
deprotecting the unsaturated telechelic polymer; and hydrogenating the unsaturated telechelic polymer to form a saturated telechelic polymer.
124 . The method of claim 121 wherein polymerizing the compound having a quaternary carbon comprises polymerizing the compound having a quaternary carbon in the presence of a chain extender and a metathesis catalyst to form an intermediate polymer.
125 . The method of claim 124 wherein the chain extender is a compound having the formula:
R 14 HC═CH—R 15 —CH═CHR 16
wherein:
R 14 and R 16 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms; and
R 15 is a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms.
126 . A method of making an alcohol and/or an amine comprising a quaternary carbon, the method comprising:
polymerizing a compound having a quaternary carbon in the presence of a chain transfer agent and a metathesis catalyst to form an unsaturated telechelic polymer; wherein the compound having a quaternary carbon has the formula: R 10 HC═CH—(R 11 ) r -Z-(R 12 ) s —CH═CHR 13 wherein:
r=0 or 1;
s=0 or 1;
Z is —C(R 3 ) 2 —, wherein each R 3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring;
R 10 and R 13 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms; and
R 11 and R 12 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms;
wherein the chain transfer agent comprises protecting groups and has the formula: Y—R 17 —HC═CH—R 18 —Y wherein:
each Y is independently a protected form of OH or NR 4 H; and
R 17 and R 18 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof;
and
converting the unsaturated telechelic polymer to an alcohol and/or an amine.
127 . The method of claim 126 wherein converting the unsaturated telechelic polymer to an alcohol and/or an amine comprises:
hydrogenating the unsaturated telechelic polymer to form a saturated telechelic polymer; and deprotecting the saturated telechelic polymer.
128 . The method of claim 126 wherein converting the unsaturated telechelic polymer to an alcohol and/or an amine comprises:
deprotecting the unsaturated telechelic polymer; and hydrogenating the unsaturated telechelic polymer to form a saturated telechelic polymer.
129 . The method of claim 126 wherein polymerizing the compound having a quaternary carbon comprises polymerizing the compound having a quaternary carbon in the presence of a chain transfer agent, a chain extender, and a metathesis catalyst to form an unsaturated telechelic polymer.
130 . The method of claim 129 wherein the chain extender is a compound having the formula:
R 14 HC═CH—R 15 —CH═CHR 16
wherein:
R 14 and R 16 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms; and
R 15 is a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms.
131 . A method of making an alcohol and/or an amine comprising a quaternary carbon, the method comprising:
polymerizing a compound having a quaternary carbon in the presence of a metathesis catalyst to form an intermediate polymer, wherein the compound having a quaternary carbon has the formula: R 10 HC═CH—(R 11 ) r -Z-(R 12 ) s —CH═CHR 13 wherein:
r=0 or 1;
s=0 or 1;
Z is —C(R 3 ) 2 —, wherein each R 3 is independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms, wherein the two R 3 groups within —C(R 3 ) 2 — can be optionally joined to form a ring;
R 10 and R 13 are each independently hydrogen or straight chain, branched, or cyclic alkyl groups containing up to 6 carbon atoms; and R 11 and R 12 are each independently a saturated aliphatic group, an aromatic group, or combinations thereof, optionally including heteroatoms; depolymerizing the intermediate polymer by reaction with a compound of the following formula to form an unsaturated telechelic polymer: CH 2 ═CH—R 21 —Y wherein:
each Y is independently a protected form of OH or NR 4 H; and
R 21 is a saturated aliphatic group, an aromatic group, or combinations thereof; and
converting the unsaturated telechelic polymer to an alcohol and/or an amine.Cited by (0)
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