Reactive polymers

Details Reactive polymers Reactive polymers

2001-03-09

2004-03-30

Berman, Susan (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Compositions to be polymerized by wave energy wherein said...

C522S050000, C522S057000, C522S062000, C522S063000, C522S065000, C522S167000, C522S173000, C522S180000, C522S008000, C522S001000, C522S011000, C522S012000, C534S560000, C568S038000, C568S041000, C568S044000, C568S045000, C568S301000

Reexamination Certificate

active

06713524

ABSTRACT:

The present invention relates to novel highly reactive polymer derivatives, articles such as biomedical articles, especially contact lenses, which are at least partly coated with said polymer derivatives and a process for coating inorganic or organic substrates using the novel polymer derivatives.
A variety of different types of processes for preparing polymeric coatings on a substrate have been disclosed in the prior art. For example, U.S. Pat. No. 5,527,925 describes functionalized photoinitiators and also organic substrates such as contact lenses containing said photoinitiators covalently bound to their surface. In one embodiment of said disclosure, the so modified surface of the contact lens is further coated with a photopolymerizable ethylenically unsaturated monomer which is then polymerized by irradiation thus forming a novel substrate surface. With this method, however, it is not always possible to obtain the desired coating characteristics, for example wettability characteristics which are necessary for the surface of biomedical devices including contact lenses. Most important, the known surface modification process is applicable only to articles having a functionalized surface, that is to say, the surface of the article either inherently contains functional groups or the functional groups have to be introduced previously by a plasma treatment or the like. However, it would be highly desirable to initiate the covalent binding of a hydrophilic layer on an “inert” surface and thereby avoiding a previous plasma treatment or the like.
Surprisingly, now there have been found novel reactive polymer derivatives which are able to react with the surface of articles that is devoid of functional groups. By means of said novel polymers it is possible to obtain articles, particularly biomedical devices such as, for example contact lenses, with an improved wettability, water-retention ability and biocompatibility.
The present invention therefore in one aspect relates to a compound of formula
wherein R
1
is an electron-withdrawing substituent and n is an integer from 0 to 2,
Z is a group which functions as a precursor for carbene or nitrene formation;
A is a radical of formula
X and X
1
are each independently of the other a group —O— or —NR
2
—, wherein R
2
is hydrogen or C
1
-C
4
-alkyl;
A
1
is C
2
-C
30
-alkyl which may be interrupted by —O—;
R is linear or branched C
1
-C
18
-alkylene or unsubstituted or C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted C
6
-C
10
-arylene, C
7
-C
18
-aralkylene, C
6
-C
10
-arylene-C
1
-C
2
-alkylene-C
6
-C
10
-arylene, C
3
-C
8
-cycloalkylene, C
3
-C
8
-cycloalkylene-C
1
-C
6
-alkylene, C
3
-C
8
-cycloalkylene-C
1
-C
2
-alkylene-C
3
-C
8
-cycloalkylene or C
1
-C
6
-alkylene-C
3
-C
8
-cycloalkylene-C
1
-C
6
-alkylene; and
(oligomer) is
(i) the radical of a telomer of formula
wherein (alk) is C
2
-C
12
-alkylene,
Q is a monovalent group that is suitable to act as a polymerization chain-reaction terminator,
p and q are each independently of another an integer from 0 to 750, wherein the total of (p+q) is an integer from 2 to 750,
and B and B′ are each independently of the other a 1,2-ethylene radical derivable from a copolymerizable vinyl monomer by replacing the vinylic double bond by a single bond, at least one of the radicals B and B′ being substituted by a hydrophilic substituent; or
(i—i) the radical of a telomer of formula
wherein (alk*) Q*, p1 and q1 each independently have the meaning of (alk), Q, p and q,
B
1
is a 1,2-ethylene radical derivable from a copolymerizable vinyl monomer by replacing the vinylic double bond by a single bond, which is substituted by a radical —T-(oligomer
1
),
wherein (oligomer
1
) independently is a radical of formula (3a) above and T is a direct bond or a radical of formula
T
1
is —O—C
2
-C
12
-alkylene which is unsubstituted or substituted by hydroxy, or is
—O—C
2
-C
12
-alkylene-NH—C(O)— or —O—C
2
-C
12
-alkylene-O—C(O)—NH—R
13
—NH—C(O)—, wherein
R
13
independently has the meaning of R above;
T
2
is C
1
-C
8
-alkylene; phenylene or benzylene;
X
3
and X
4
are each independently of the other a bivalent group —O— or —NR
2
′, wherein R
2
′ is hydrogen or C
1
-C
6
-alkyl;
(alk**) is C
1
-C
6
-alkylene and (alk***) is C
2
-C
12
-alkylene, and
m and x are each independently of the other the number 0 or 1; and
B
1
′ independently has the meaning of B
1
or B;
(ii) the radical of an oligomer of the formula
wherein R
3
is hydrogen or unsubstituted or hydroxy-substituted C
1
-C
12
-alkyl, u is an integer from 2 to 750 and Q′ is a radical of a polymerization initiator; or
(iii) the radical of formula
wherein X
2
independently has the meaning of X above, and R
3
and u are as defined above, or
(iv) the radical of an oligomer of formula
wherein R
4
and R
4
′ are each independently C
1
-C
4
-alkyl, An
−
is an anion, v is an integer from 2 to 750, and Q″ is a monovalent group that is suitable to act as a polymerization chain-reaction terminator;
subject to the proviso that A is not a radical of formula (2b) if (oligomer) is a radical of formula (3b) or (3c).
The following preference apply to the variables contained in the definition of the compounds of formula (1):
Z is, for example, a group of formula
wherein R
5
is an electron-withdrawing substituent, for example, fluorinated C
1
-C
6
-alkyl, for example a radical —C
2
F
5
or preferably a radical —CF
3
.
R
1
is, for example, hydroxy, C
1
-C
4
-alkoxy, nitro, trifluoromethyl or halogen such as, for example, fluorine or chlorine.
The variable n is for example the number 1 or preferably 0.
X and X
1
are each independently preferably a group —O— or —NH— and in particular a group —NH— each.
A
1
is preferably linear C
2
-C
12
-alkyl radical witch may be interrupted by —O—, for example a branched or preferably linear C
2
-C
12
-alkyl radical or in particular a radical —(CH
2
CH
2
O)
1-5
—CH
2
CH
2
—.
The radicals A of formulae (2a)-(2g) and the radicals of formulae (2a*)-(2e*) are in each case to be understood that the left bond is directed to the phenyl ring or B
1
and the right bond is directed to (oligomer) or (oligomer
1
), respectively.
R as alkylene in formula (2g) is preferably linear or branched C
1
-C
12
-alkylene, more preferably C
1
-C
6
-alkylene and most preferably C
1
-C
4
-alkylene.
R as alkylene in formula (2f) is preferably a linear or branched C
3
-C
14
alkylene radical, more preferably a linear or branched C
4
-C
12
alkylene radical and most preferably a linear or branched C
6
-C
10
-alkylene radical.
When R is arylene, it is, for example, naphthylene or especially phenylene, each of which may be substituted, for example, by C
1
-C
4
-alkyl or by C
1
-C
4
-alkoxy. Preferably, R as arylene is 1,3- or 1,4-phenylene that is unsubstituted or substituted by C
1
-C
4
-alkyl or by C
1
-C
4
-alkoxy in the ortho-position to at least one linkage site.
R as aralkylene is preferably naphthylalkylene and most preferably phenylalkylene. The alkylene group in aralkylene contains preferably from 1 to 12, more preferably from 1 to 6 and most preferably from 1 to 4 carbon atoms. Most preferably, the alkylene group in aralkylene is methylene or ethylene.
When R is cycloalkylene, it is preferably C
5
-C
6
-cycloalkylene and most preferably cyclohexylene that is unsubstituted or substituted by methyl.
When R is cycloalkylene-alkylene, it is preferably cyclopentylene-C
1
-C
4
-alkylene and especially cyclohexylene-C
1
-C
4
-alkylene, each unsubstituted or mono- or poly-substituted by C
1
-C
4
-alkyl, especially methyl. More preferably, the group cycloalkylene-alkylene is cyclohexylene-ethylene and, most preferably, cyclohexylene-methylene, each unsubstituted or substituted in the cyclohexylene radical by from 1 to 3 methyl groups.
When R is alkylene-cycloalkylene-alkylene, it is preferably C
1
-C
4
-alkylene-cyclopentylene-C
1
-C
4
-alkylene and especially C
1
-C
4
-alkylene-cyclohexylene-C
1
-C
4
-alkylene, each unsubstituted or mono- or poly-substituted by C
1
-C
4
-alkyl, especially methyl. More

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