Polymers with crosslinkable pendent groups

Details Polymers with crosslinkable pendent groups Polymers with crosslinkable pendent groups

1999-03-26

2002-12-10

Wu, David W. (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S260000, C526S266000, C526S227000, C526S273000, C526S323100

Reexamination Certificate

active

06492478

ABSTRACT:

The present invention relates to novel water-soluble block copolymers comprising polyoxyalkylene units and having crosslinkable side groups, to processes for their preparation, and to their use in the production of mouldings, especially contact lenses.
Polymers comprising polyalkylene oxide and having polymerisable end groups and their use in the production of contact lenses are already known, for example from EP-A-273 763.
Furthermore, there are known, for example from A. Kameyama et al. Macromol. 25, 2307 (1992), H. Itoh et al. Macromol. 28, 883 (1995) or H. Itoh et al. J. Pol. Sci. A, Pol. Chem. 34, 217 (1996), polyesters having chloromethyl side groups, polymers derived therefrom that have side groups comprising carboxy groups, and polyesters having vinyl ether side groups.
Surprisingly, novel crosslinkable polyether-polyester copolymers have now been found, which are suitable especially for the production of contact lenses.
The present invention relates to prepolymers comprising structural units of the formula
Z is straight-chained or branched C
1
-C
12
alkylene or unsubstituted or C
1
-C
4
alkyl- or C
1
-C
4
-alkoxy-substituted phenylene or C
7
-C
12
aralkylene,
x and t are each independently of the other the number 0 or 1,
R
5
is hydrogen, C
1
-C
4
alkyl or halogen,
R
6
is hydrogen, C
1
-C
4
alkyl, phenyl, carboxy or halogen,
R
7
is hydrogen when R
6
is phenyl or carboxy, or is hydrogen or carboxy when R
6
is hydrogen, C
1
-C
4
alkyl or halogen,
R
8
is a C
2
-C
12
alkylene radical, a phenylene radical or a C
7
-C
12
aralkylene radical,
R
9
and R
9
′ are each independently of the other hydrogen, C
1
-C
4
alkyl or halogen,
R
1
is a radical of the formula
—[CH
2
—CHR″—O]
n
—CH
2
—CHR″—  (3a) or
—[CH
2
—CH
2
—CH
2
—CH
2
—O]
n
—CH
2
—CH
2
—CH
2
—CH
2
—  (3b);
 or an alkylene radical having up to 20 carbon atoms which may be interrupted by one or more ester, urethane or ureido groups and/or may be substituted by hydroxy; or a cycloalkylene radical having from 6 to 20 carbon atoms; or an arylene radical having from 6 to 20 carbon atoms; or an arylenealkylene, alkylenearylene, alkylenearylenealkylene or arylenealkylenearylene radical,
R
2
is a radical of the formula
—CH
2
—[CH
2
—CHR*—O]
p
—CH
2
—  (4) or
—R
3
—C(O)—[O—CHR*—CH
2
]
p
—O—(O)C—R
3
—  (5);
 or an alkylene radical having up to 20 carbon atoms which may be interrupted by one or more ester, urethane or ureido groups and/or may be substituted by hydroxy; or a cycloalkylene radical having from 6 to 20 carbon atoms; or an arylene radical having from 6 to 20 carbon atoms; or an arylenealkylene, alkylenearylene, alkylenearylenealkylene or arylenealkylenearylene radical,
R′, R″ and R* are each independently of the others hydrogen or C
1
-C
4
alkyl,
R
3
is an alkylene radical having up to 20 carbon atoms; or a cycloalkylene radical having from 6 to 20 carbon atoms; or an arylene radical having from 6 to 20 carbon atoms, and n, m, p and q are each independently of the others a number from 1 to 30,
with the proviso that at least one of the radicals R
1
and R
2
is a radical of formula (3a), (3b), (4) or (5).
Z as an alkylene radical is preferably linear or branched C
1
-C
8
alkylene, especially linear C
1
-C
4
alkylene and more especially linear C
1
-C
2
alkylene. In a preferred embodiment of the invention, Z is methylene.
Z as a phenylene radical is, for example, unsubstituted or methyl- or methoxy-substituted 1,2-, 1,3- or 1,4-phenylene. Z as a phenylene radical is preferably 1,3- or 1,4-phenylene.
Z as an aralkylene radical is, for example, unsubstituted or methyl- or methoxy-substituted benzylene, the methylene group in each case being bonded to the amine nitrogen. Z as an aralkylene radical is preferably the 1,3- or 1,4-phenylenemethylene radical, the methylene group in each case being bonded to the amine nitrogen —NH—.
Z is preferably unsubstituted or methyl- or methoxy-substituted phenylene or phenylenemethylene or C
1
-C
8
alkylene, especially 1,3- or 1,4-phenylene or C
1
-C
4
alkylene, more especially C
1
-C
2
alkylene and most especially methylene.
x is preferably the number 0. t is preferably the number 1.
R
5
is preferably hydrogen, C
1
-C
4
alkyl or chlorine, especially hydrogen or C
1
-C
4
alkyl, more especially hydrogen, methyl or ethyl and most especially hydrogen or methyl.
R
6
is preferably hydrogen, methyl or phenyl and especially hydrogen.
R
7
is preferably hydrogen.
R
8
is preferably a C
2
-C
6
alkylene radical or a 1,3- or 1,4-phenylene radical, especially a C
2
-C
3
alkylene radical. R
9
and R
9
′ are each independently of the other preferably hydrogen, methyl or chlorine. R
9
and R
9
′ are each independently of the other especially hydrogen or methyl.
Each of R′, R″ and R* as C
1
-C
4
alkyl is preferably methyl or ethyl and especially methyl.
R′ and R″ are each independently of the other preferably hydrogen, methyl or ethyl and especially hydrogen or methyl.
R* is especially hydrogen or methyl and more especially hydrogen.
m is preferably a number from 1 to 6 and especially a number from 1 to 4. q is, for example, a number from 1 to 6, preferably a number from 2 to 4 and especially the number 2.
R in formula (1) is preferably a radical of the formula
—O—(O)C—CR
5
═CH
2
  (2a′) or
—O—(O)C—(CH
2
)
m
—O—(O)C—NH—(CH
2
)
q
—O—(O)C—CR′═CH
2
  (2b′),
wherein the variables contained therein each have the meanings and preferred meanings indicated above.
In an especially preferred embodiment of the invention, R in formula (1) is a radical of formula (2a′) indicated above wherein R
5
is hydrogen or methyl.
In formulae (3a) and (3b), n is, for example, a number from 5 to 30, advantageously from 5 to 25, preferably from 8 to 25 and especially from 10 to 25.
When R
1
is an alkylene radical it is, for example, straight-chained or branched C
1
-C
20
-alkylene which is unsubstituted or substituted, for example by hydroxy, and/or, with the exception of methylene, may be interrupted by one or more groups —COO—, —OCO—, —NHCO—O—, —OCONH— or —NHCONH—. R
1
as an alkylene radical is preferably unsubstituted or hydroxy-substituted C
1
-C
20
alkylene, especially unsubstituted C
1
-C
12
alkylene and more especially unsubstituted C
1
-C
6
alkylene. Examples of alkylene radicals R
1
that are very especially preferred are methylene, 1,2-ethylene, 1,3-propylene and 1,4-butylene.
R
1
as cycloalkylene is, for example, 1,2-, 1,3- or 1,4-cyclohexylene which may be substituted by C
1
-C
4
alkylene, or is a radical of the formula
R
1
as arylene is, for example, 1,2-, 1,3- or 1,4-phenylene which is unsubstituted or is substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy or by halogen, or is a radical of the formula
wherein B is, for example, a group —O—, —NH—, —OCO—, —CONH— or —NHCONH—. R
1
as arylene is preferably 1,2-, 1,3- or 1,4-phenylene.
R
1
as arylenealkylene, alkylenearylene or alkylenearylenealkylene is, for example, a radical —C
6
H
5
—C
1
-C
4
alkylene—, —C
1
-C
4
alkylene-C
6
H
5
— or —C
1
-C
4
alkylene-C
6
H
5
—C
1
-C
4
alkylene, preferably the radical —C
6
H
5
—CH
2
—, —CH
2
—C
6
H
5
— or —CH
2
—C
6
H
5
—CH
2
—.
R
1
as arylenealkylenearylene is, for example, a radical of the formula
wherein B
1
is straight-chained or branched C
1
-C
6
alkylene which is unsubstituted or is substituted by hydroxy, preferably straight-chained or branched C
1
-C
4
alkylene. Examples of suitable radicals B
1
are —CH
2
—, —C(CH
3
)
2
— and —CH
2
—CH
2
—.
R
1
is advantageously a radical of formula (3a) or (3b) indicated above, or C
1
-C
20
alkylene, 1,2-, 1,3- or 1,4-phenylene or a radical of the formula
wherein B
1
is straight-chained or branched C
1
-C
4
alkylene.
R
1
is preferably a radical of formula (3a) indicated above, or C
1
-C
20
alkylene, especially a radical of formula (3a) indicated above wherein n is a number from 5 to 25 and R″ is hydrogen or methyl, or C
1
-C
12
alkylene, and more especially a

Affiliated with

Also associated with

Rating

Polymers with crosslinkable pendent groups does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Polymers with crosslinkable pendent groups, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polymers with crosslinkable pendent groups will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2930212