Polymers

Details Polymers Polymers

1999-11-18

2002-10-29

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...

C526S302000, C526S317100

Reexamination Certificate

active

06472489

ABSTRACT:

The present invention relates to novel polyallyl amine based polymers, a process for their manufacture and their use for the preparation of mouldings, in particular ophthalmic mouldings, or surface coatings.
The polymers of the invention are preferably a derivative of a polyallyl amine having a weight average molecular weight of at least 2000 that, based on the number of amino groups of the polyallyl amine, comprises from approximately 1 to 99% of units of formula
wherein R is C
2
-C
6
-alkyl which is substituted by two or more same or different substituents selected from the group consisting of hydroxy, C
2
-C
5
-alkanoyloxy and C
2
-C
5
-alkylamino-carbonyloxy.
R is preferably linear C
3
-C
6
-alkyl, more preferably linear C
4
-C
5
-alkyl, and most preferably n-pentyl which is in each case substituted as defined above.
Suitable substituents of the alkyl radical R are —OH, a radical —O—C(O)—R
1
and/or a radical —O—C (O)—NH—R
1
′ wherein R
1
and R
1
′ are each independently of the other C
1
-C
4
-alkyl, preferably methyl, ethyl or n- or iso-propyl, and more preferably methyl or ethyl.
Preferred substituents of the alkyl radical R are hydroxy, acetyloxy, propionyloxy, n- or iso-butanoyloxy, methylaminocarbonyloxy or ethylaminocarbonyloxy, especially hydroxy, acetyloxy or propionyloxy and in particular hydroxy.
A preferred embodiment of the invention relates to polyallyl amines comprising units of the above formula (1), wherein R is a radical of formula
wherein p is 1, 2, 3, 4 or 5, preferably 3 or 4 and in particular 4, each R* is independently hydrogen or a radical —C(O)—R
1
or —C(O)—NH—R
1
′, and for R
1
and R
1
′ the above meanings and preferences apply. R is even more preferred a radical of the above formula (2) wherein p is 3 or 4, in particular 4, and each group —OR* independently is hydroxy or hydroxy which is partly or completely acetylated, in particular hydroxy. Particular preferred radicals R are 1,2,3,4,5-pentahydroxy-n-pentyl or 1,2,3,4,5-pentahydroxy-n-pentyl wherein the hydroxy groups are partly or completely acetylated.
The polymers of the invention are derivatives of a polyallyl amine that, based on the number of amino groups of the polyallyl amine, comprise from about 1 to 99%, preferably from 10 to 80%, more preferably, from 15 to 75%, even more preferably 20 to 70% and in particular 40 to 60%, of units of formula (1). The polymers of the invention are advantageously water-soluble.
The term units of formula (1) or of another formula number below is always to be understood as encompassing one or more different species falling under the respective formula; preferably the term means one single species.
In addition to the units of formula (1), the novel polyallyl amines may comprise further modifier units. Of the many possibilities for such modifiers, the following may be mentioned by way of example:
wherein R
2
is C
1
-C
12
-alkyl which is unsubstituted or substituted by an amino, hydroxy or carboxy group;
wherein X is —O— or —NH— and R
3
is C
1
-C
12
-alkyl;
wherein R
4
is hydrogen, C
1
-C
6
-alkyl which is unsubstituted or substituted by hydroxy, or is C
5
-C
7
-cycloalkyl or phenyl;
wherein R
5
is C
1
-C
12
-alkyl and R
5
′ is hydrogen or C
1
-C
12
-alkyl; or
wherein R
6
is a radical comprising an ethylenically unsaturated group, for example a C
3
-C
12
-alkenyl radical which may be further substituted by hydroxy, or 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
8
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
7
and R
7
′ independently of the other is hydrogen, C
1
-C
4
alkyl or halogen,
each of m and n independently of the other is the number 0 or 1, and
Z″ is C
1
-C
6
alkylene.
In the above formulae, the following meanings and preferences apply:
R
2
is preferably C
1
-C
6
-alkyl, especially C
1
-C
4
-alkyl and even more preferably C
1
-C
3
-alkyl which may be substituted in each case as mentioned above. Preferred substituents of the alkyl radical R
2
are a hydroxy or carboxy group, in particular a hydroxy group.
Preferred meanings of R
2
are (i) C
1
-C
3
-alkyl, in particular methyl or ethyl; (ii) hydroxy-C
2
-C
5
-alkyl, especially hydroxy-C
2
-C
3
-alkyl and in particular &bgr;-hydroxyethyl, &bgr;-hydroxypropyl or &ggr;-hydroxypropyl; or (iii) carboxy-C
1
-C
6
-alkyl, especially carboxy-C
2
-C
4
-alkyl and in particular —(CH
2
)
2-3
-COOH.
X is —O— or preferably —NH—. R
3
is preferably C
1
-C
6
-alkyl, more preferably C
1
-C
3
-alkyl and in particular methyl, ethyl or n- or isopropyl.
R
4
is preferably hydrogen, hydroxy-substituted C
2
-C
4
-alkyl or cyclohexyl, and in particular hydrogen, 2-hydroxyethyl or 2-hydroxypropyl.
R
5
is preferably C
1
-C
6
-alkyl, more preferably C
1
-C
3
-alkyl and in particular methyl or ethyl. R
5
′ is preferably hydrogen or C
1
-C
3
-alkyl, in particular hydrogen.
R
6
as an alkenyl radical is preferably a C
3
-C
6
-alkenyl radical which is optionally substituted by hydroxy and more preferably hydroxy-substituted C
3
-C
5
-alkenyl. Examples of preferred alkenyl radicals R
6
are allyl or in particular the radical —CH
2
—CH(OH)—CH
2
—CH═CH
2
.
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
8
are, for example, C
1
-C
4
alkoxy, halogen, phenyl or carboxy.
R
8
is, for example, a radical of formula
wherein
q is the number 0 or 1,
R
9
is hydrogen, C
1
-C
4
alkyl or halogen,
each of R
10
and R
11
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.
q is the number 1 or, preferably, the number 0.
R
9
is preferably hydrogen, methyl or chlorine and most preferably hydrogen or methyl.
Each of R
10
and R
11
independently of the other is preferably hydrogen, carboxy, chlorine, methyl or phenyl. In a preferred embodiment of the invention, R
10
is hydrogen, chlorine, methyl or phenyl and R
11
is hydrogen or carboxy. Most preferably, R
10
and R
11
are each hydrogen.
Examples of suitable radicals R
8
are vinyl, 2-propenyl, allyl, 2-butenyl, o-, m- or p-vinylphenyl, 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
8
correspond to formula (5) wherein q is 0, R
9
is hydrogen or methyl, R
10
is hydrogen, methyl, chlorine or phenyl and R
11
is hydrogen or carboxy.
Other especially preferred radicals R
8
correspond to the above formula (5) wherein q is 1, Z′ is 1,3- or 1,4-phenylene or C
1
-C
6
alkylene, especially C
1
-C
2
alkylene, R
9
is hydrogen or methyl and R
10
and R
11
are each hydrogen.
Z″ is preferably C
1
-C
4
alkylene, especially m

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