Stock material or miscellaneous articles – Composite – Of silicon containing
Reexamination Certificate
2002-10-04
2004-12-07
Peng, Kuo-Liang (Department: 1712)
Stock material or miscellaneous articles
Composite
Of silicon containing
C623S004100, C528S028000, C528S026000, C525S479000, C525S404000, C427S384000, C427S387000
Reexamination Certificate
active
06828029
ABSTRACT:
Phospholipids are phosphate diester compounds, naturally found in the cell membrane, in which one of the alcohol residues is generally a glycerol derivative, and the other is a derivative of a different alcohol which may include a non-ionic, cationic or even an anionic functionality. Phospholipid and phospholipid analogues are of increasing interest, for example to impart the useful properties of biocompatibility, haemocompatibility and to influence the interaction of surfaces with biomolecules such as proteins or enzymes.
Our previous disclosures such as EP-A 0032622, EP-A-0157469, EP-A-0555295, EP-A-0601041, EP-A-0593561, EP-A-00639989, WO-A-9416748 and WO-A-9416749 describe various synthetic zwitterionic compounds including phospholipid analogues and their application in devices having biocompatible and haemocompatible surfaces. The present invention extends this methodology to new polymer systems comprising monomers and macromers produced by a Michael-type addition.
It is well known in the literature that amines undertake nucleophilic attack on the a, unsaturated carbonyl of an acrylate functionality, resulting in a Michael-type 1,4-adduct (Recent stereoselective synthetic approaches to -amino acids. Cole, Derek C.,
Tetrahedron
(1994), 50(32), 9517-82).
This technology has been applied in the preparation of a range of curable coatings (Addition products, radiation-curable surface coating compositions based on the addition products, and their use for wood coating and paper coating, Hintze-Bruning, Horst; Cibura, Klaus; Baltus, Wolfgang, U.S. Pat. No. 5,792,827; High-solids coatings—formulation aspects. Nowak, Michael T. USA. High Solids Coat. (1982), 7(3), 23-8) or resins (Curing agents for liquid epoxy resins, and curable polymer compositions containing them. Shiono, Kenji; Suzuki, Takehiro. JP 09291135; A process for preparation of room-temperature-curable resins. Furukawa, Hisao; Kawamura, Jo., EP 274112).
It has also been used extensively in polymer science, for example, to produce a variety of polymer hybrids (Conductive wire coating based on a curable acrylate-modified amine-terminated polyamide. Frihart, Charles R.; Kliwinski, Joseph. WO 9724191; A polylactone having amino groups, its preparation, and coating and printing ink compositions containing it. Matsui, Hideki, EP 713894; Grafting of amine-functional polymers onto functionalized oxymethylene polymers and the resulting graft polymers thereof. Auerbach, Andrew B.; Broussard, Jerry A.; Yang, Nan L.; Paul, James L. EP 400827) or to build dendrimer structures (Dense star polymers. Tomalia, Donald A.; Dewald, James R. WO 8402705).
It can also be used to functionalise biologically active amine-bearing compounds (A synthesis of N-substituted-alanines: Michael addition of amines to trimethylsilyl acrylate. Kwiatkowski, Stefan; Jeganathan, Azhwarsamy; Tobin, Thomas; Watt, David S. Maxwell H.
Synthesis
(1989), Issue 12, 946-9). In EP-A-0933399 polysiloxane compounds having at least one aminoalkyl substituent on a silicon atom are cross-linked by reaction with di- or oligo-acrylate compounds, optionally in the presence of other acrylic compounds. One example of a substituted acrylic compound which could be incorporated is N,N-dimethyl-N-methacryloxyethyl-N-3-sulphopropyl)-ammonium betaine.
In some of the prior art the reaction may be carried out with either acrylate or methacrylate, although the former is generally preferred in the literature on reactivity grounds. The reaction proceeds usually without catalysis, although there are reports of catalysts to promote solely 1,4 addition in good yields (Catalysis of the specific Michael addition: the example of acrylate acceptors. Cabral, Jose; Laszlo, Pierre; Mahe, Loic; Montaufier, Marie Therese; Randriamahefa, S. Lalatiana.,
Tetrahedron Lett
. (1989), 30(30), 3969-72).
The present invention relates to new polymers, processes for producing them, processes for coating surfaces with them and polymer compositions. The invention also provides new prepolymers and processes for their production.
Such polymers are particularly useful in the manufacture or coating of devices with medical applications such as blood contacting devices, contact and intraocular lenses, and other devices which are used in contact with protein-containing or biological fluids.
The present invention provides a zwitterion containing Michael-type adduct having the formula (I)
wherein
Z is a zwitterionic group;
X is an electron withdrawing group selected from the group consisting of carbonyl and sulphone groups, sulphonium and phosphonium salts;
R is selected from the group consisting of linear and branched alkanediyl, alkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl, cycloalkynediyl, arylene, alkarylene, aralkylene, alkoxyarylene, alkoxyalkyl, oligo(alkoxy)alkyl, mono- and di-alkylaminoalkyl N-arylaminoalkyl, N-aryl-N-alkylaminoalkyl;
R
1
and R
2
are independently selected from hydrogen and C
1
-C
12
alkyl groups;
A is O or NR
6
, where R
6
is selected from the group consisting of hydrogen and C
1-6
alkyl.
R
3
is selected from the group consisting hydrogen, linear and branched alkyl, alkenyl, and alkynyl groups, alkoxycarbonyl, alkylaminocarbonyl, cycloalkyl, cycloalkenyl, cycloalkynyl, haloaryl, haloalkyl, aryl, alkaryl, aralkyl, alkoxyaryl, alkoxyalkyl, oligoalkoxyalkyl, aminoalkyl, mono- and di-alkylaminoalkyl, arylaminoalkyl, N-aryl-N-alkylaminoalkyl and -aminoaryl, acyloxy, acyloxyalkyl, acylaminoalkyl, N-diacyl-iminoalkyl groups, mono- and di-alkylaminocarbonyl, organosilyl, arylamino carbonyl, aryl(alkyl)amino carbonyl, and organosiloxyl groups and any of the above groups substituted with
a reactive group,
a group NHCOOR
5
in which R
5
is selected from the group consisting hydrogen, linear and branched alkyl, alkenyl, and alkynyl groups, cycloalkyl, cycloalkenyl, cycloalkynyl, haloaryl, haloalkyl, aryl, alkaryl, aralkyl, alkoxyaryl, alkoxyalkyl, oligoalkoxyalkyl, aminoalkyl, mono- and di-alkylaminoalkyl, arylaminoalkyl, N-aryl-N-alkylaminoalkyl and aminoaryl, acyloxyalkyl, acylaminoalkyl, N-diacyl-iminoalkyl groups, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, hydroxyaryl, hydroxyalkoxyalkyl and hydroxy(oligoalkoxy)alkyl;
a group —NHCONR
7
R
8
in which R
7
and R
8
are selected from the group consisting hydrogen, linear and branched alkyl, alkenyl, and alkynyl groups, cycloalkyl, cycloalkenyl, cycloalkynyl, haloaryl, haloalkyl, aryl, alkaryl, aralkyl, alkoxyaryl, alkoxyalkyl, oligoalkoxyalkyl, aminoalkyl, mono- and di-alkylaminoalkyl, arylaminoalkyl, N-aryl-N-alkylaminoalkyl and aminoaryl, acyloxyalkyl, acylaminoalkyl, N-diacyl-iminoalkyl groups, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, hydroxyaryl, hydroxyalkoxyalkyl and hydroxy(oligoalkoxy)alkyl; or
a polymeric moiety; and
R
4
is selected from the group consisting hydrogen, linear and branched alkyl, alkenyl, and alkynyl groups, alkoxycarbonyl, alkylaminocarbonyl, cycloalkyl, cycloalkenyl, cycloalkynyl, haloaryl, haloalkyl, aryl, alkaryl, aralkyl, alkoxyaryl, alkoxyalkyl, oligoalkoxyalkyl, aminoalkyl, mono- and di-alkylaminoalkyl, arylaminoalkyl, N-aryl-N-alkylaminoalkyl and -aminoaryl, acyloxy, acyloxyalkyl, acylaminoalkyl, N-diacyl-iminoalkyl groups, mono- and di-alkylaminocarbonyl, organosilyl, arylamino carbonyl, aryl(alkyl)amino carbonyl, and organosiloxyl groups and any of the above groups substituted with
a group II
in which the groups R, R
1
, R
2
. R
4
, Z and A are the same as in (I);
a group III
in which
A
1
is O or NR
13
where R
13
is hydrogen or C
1-4
alkyl;
X
1
is an electron withdrawing group selected from carbonyl, sulphonyl, sulphonium and phosphonium groups;
R
12
is H or C
1-6
alkyl;
R
10
and R
11
are independently selected from H and C
1-4
alkyl; and
R
9
is optionally substituted alkyl or aryl;
a reactive group; or.
a polymeric moiety.
In the definition of R
3
, and R
4
, and any of the groups below any alkyl group or moiety is preferably C
1-18
alkyl, any alkenyl group or moiety is preferably C
2-18
alkenyl, any alkynyl group or moiety is preferably C
2-12
alkynyl, any aryl group or
Lewis Andrew Lennard
Redman Richard Paul
Biocompatibles UK Limited
Peng Kuo-Liang
Sughrue & Mion, PLLC
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