Crosslinkable polyurea polymers

Details Crosslinkable polyurea polymers Crosslinkable polyurea polymers

2000-03-16

2002-11-12

Seidleck, James J. (Department: 1711)

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

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S123000, C525S128000, C525S903000, C523S106000, C264S002600, C522S173000, C522S174000, C522S150000, C522S151000, C522S152000

Reexamination Certificate

active

06479587

ABSTRACT:

The present invention relates to novel crosslinkable polyureas, to a process for the preparation thereof and to the use thereof in the manufacture of mouldings, especially ophthalmic mouldings, for example contact lenses.
The present invention relates to prepolymers of formula
Q—CP—Q  (1),
wherein
Q is an organic radical that comprises at least one crosslinkable group, and
CP is a bivalent copolymer fragment consisting of the segments A, B and T, wherein:
A is a bivalent radical of formula
—RN—A
1
—NR′—  (2a),
 wherein A
1
is the bivalent radical of a polyalkylene glycol or is a linear or branched alkylene radical having from 2 to 24 carbon atoms and each of R and R′ independently of the other is hydrogen or unsubstituted or substituted C
1
-C
6
alkyl or, in the case of the amino group that terminates the copolymer fragment, may also be a direct, ring-forming bond;
T is a bivalent radical of formula
 wherein X is a bivalent aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, aromatic, araliphatic or aliphatic-heterocyclic radical; and
B is a radical of formula
—R
1
N—B
1
—NR
1
′—  (2b),
 wherein each of R
1
and R
1
′ independently of the other has the meanings given above for R, B
1
is a bivalent aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, aromatic or araliphatic hydrocarbon radical that is interrupted by at least one amine group of formula
 and R
2
is hydrogen, a radical Q mentioned above or a radical of formula
Q—CP′—  (4),
 wherein
Q is as defined above, and CP′ is a bivalent copolymer fragment independently consisting of at least two of the above-mentioned segments A, B and T; with the provisos
that in the copolymer fragments CP and CP′ a segment A or B is followed by a segment T in each case;
that in the copolymer fragments CP and CP′ a segment T is followed by a segment A or B in each case;
that the radical Q in formulae (1) and (4) is bonded to a segment A or B in each case; and that the N atom in formula (3) is bonded to a segment T when R
2
is a radical of formula (4).
Q is, for example, an olefinically unsaturated, copolymerisable radical that is bonded to the amine nitrogen —NR—, —NR′—, —NR
1
— or —NR
1
′— in a suitable manner, for example directly, by way of a functional group or by way of a bridge member, or that together with —NR—, —NR′—, —NR
1
— or —NR
1
′— forms a cyclic ring; in the latter case, R, R′, R
1
or R
1
′ is a direct, ring-forming bond.
The radical Q corresponds, for example, to a radical R
3
mentioned hereinbelow or to a radical of formula
wherein Q
1
is, for example, a radical of formula
and wherein
Z is linear or branched C
2
-C
12
alkylene,
R
3
is an olefinically unsaturated copolymerisable radical having from 2 to 24 carbon atoms which may be further substituted,
W is a C
2
-C
12
alkylene radical, phenylene radical or C
7
-C
12
aralkylene radical, each of R
4
and R
4
′ independently of the other is hydrogen, C
1
-C
4
alkyl or halogen,
R
5
is a bivalent aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, aromatic or araliphatic hydrocarbon radical,
R
6
is hydrogen or C
1
-C
4
alkyl,
each of alk and alk′ independently of the other is a linear or branched C
1
-C
12
alkylene radical,
each of m and n independently of the other is the number 0 or 1,
Z″ is C
1
-C
6
alkylene and
P
1
independently is a radical of the above-mentioned formula (5) wherein Q
1
is a radical of the above formula (5a), (5b), (5c) or (5e) and n independently is as defined above.
Z is preferably linear or branched C
2
-C
8
alkylene, more preferably linear C
2
-C
6
alkylene and most preferably linear C
2
-C
4
alkylene. In a preferred embodiment of the invention, Z is 1,3-propylene or, especially, 1,2-ethylene.
Suitable substituents on the olefinic C
2
-C
24
radical R
3
are, for example, C
1
-C
4
alkoxy, halogen, phenyl or carboxy.
R
3
is, for example, a radical of formula
wherein p is the number 0 or 1,
R
7
is hydrogen, C
1
-C
4
alkyl or halogen,
each of R
8
and R
9
independently of the other is hydrogen, C
1
-C
4
alkyl, phenyl, carboxy or halogen, and
Z′ is linear 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.
When Z′ is a phenylene radical, it is, for example, unsubstituted or methyl- or methoxy-substituted 1,2-, 1,3- or 1,4-phenylene. Preferably, Z′ as a phenylene radical is 1,3- or 1,4-phenylene.
When Z′ is an aralkylene radical, it is, for example, unsubstituted or methyl- or methoxy-substituted benzylene, wherein the methylene group is bonded to the amine nitrogen in each case. Preferably, Z′ as an aralkylene radical is the 1,3- or 1,4-phenylenemethylene radical, wherein the methylene group is bonded to the amine nitrogen —NH— in each case.
Z′ is preferably unsubstituted or methyl- or methoxy-substituted phenylene or phenylene-methylene or C
1
-C
12
alkylene, more preferably 1,3- or 1,4-phenylene or C
1
-C
6
alkylene, especially C
1
-C
2
alkylene and most preferably methylene.
p is the number 1 or, preferably, the number 0.
R
7
is preferably hydrogen, methyl or chlorine and most preferably hydrogen or methyl.
Each of R
8
and R
9
independently of the other is preferably hydrogen, carboxy, chlorine, methyl or phenyl. In a preferred embodiment of the invention, R
8
is hydrogen, chlorine, methyl or phenyl and R
9
is hydrogen or carboxy. Most preferably, R
8
and R
9
are each hydrogen.
Examples of suitable radicals R
3
are vinyl, 2-propenyl, allyl, 2-butenyl, o-, m- or p-vinyl-phenyl, styryl, 2-carboxyvinyl, 2-chloro-2-carboxyvinyl, 1,2-dichloro-2-carboxyvinyl, 1,2-dimethyl-2-carboxyvinyl and 2-methyl-2-carboxyvinyl.
Especially preferred radicals R
3
correspond to formula (6) wherein p is 0, R
7
is hydrogen or methyl, R
8
is hydrogen, methyl, chlorine or phenyl and R
9
is hydrogen or carboxy.
Other especially preferred radicals R
3
correspond to the above formula (6) wherein p is 1, Z′ is 1,3- or 1,4-phenylene or C
1
-C
6
alkylene, especially C
1
-C
2
alkylene, R
7
is hydrogen or methyl and R
8
and R
9
are each hydrogen.
Z″ is preferably C
1
-C
4
alkylene, especially methylene or 1,1-dimethylmethylene.
One group of suitable radicals Q corresponds to the above formula (5) wherein n is 0 and Q
1
is a radical of the above formula (5a) wherein m is 0 and for R
3
the meanings and preferences given above apply.
A second group of suitable radicals Q corresponds to the above formula (5) wherein n is 1 and Q
1
is a radical of the above formula (5a) wherein m is 0 and for R
3
and Z the meanings and preferences given above apply.
A further group of suitable radicals Q corresponds to the above formula (5) wherein n is 1 and Q
1
is a radical of the above formula (5a) wherein m is 1 and for R
3
and Z the meanings and preferences given above apply.
A further group of suitable radicals Q corresponds to the above formula (5) wherein n is 0 and Q
1
is a radical of the above formula (5e) wherein for R
3
and Z″ the meanings and preferences given above apply.
In formulae (5b) and (5c), the variable W is preferably a C
2
-C
6
alkylene radical or a 1,3- or 1,4-phenylene radical and most preferably a C
2
-C
3
alkylene radical. Each of R
4
and R
4
′ independently of the other is preferably hydrogen, methyl or chlorine. Most preferably, each of R
4
and R
4
′ independently of the other is hydrogen or methyl.
In formula (5d), R
5
is, for example, linear or branched C
3
-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, C
1
-C
6
alkylene-C
3
-C
8
cycloalkylene-C
1
-C
6
alkylene or an aliphatic-heterocyclic radical comprising at least one hydantoin group.
R
5
as alkylene is pref

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