Self-sterilizing products
Self-sterilising products, and in particular novel products comprising phthalocyanine derivatives bound to polymers, a process for the preparation of said products and their use for preparing self-sterilising industrial and medical articles or devices, are described.
1. A polymeric product comprising a polymer bound, directly or through a spacer, to a phthalocyanine derivative of general formula (I):
wherein said phthalocyanine derivative of general formula (I) is selected from the group of compounds consisting of:
Diiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 2 =R 3 =H, and R=1,3-bis-(trimethylammonium)-2-propyloxy in position 2 [Compound 1];
Octaiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 2 =H, and R=R 3 =1,3-bis-(dimethyl-ethylacetate-ammonium)-2-propyloxy in positions 2, 9(10), 16(17), 23(24) [Compound 2];
Diiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 2 =R 3 =H, and R=1,3-bis-(dimethyl-ethylacetate-ammonium)-2-propyloxy in position 2 [Compound 3];
Octaiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 2 =H, and R=R 3 =1,3-bis-(dimethyl-(2-hydroxycarbonyl)ethyl-ammonium)-2-propyloxy in positions 2, 9(10), 16(17), 23(24) [Compound 4];
Diiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 2 =R 3 =H, and R=1,3-bis-(dimethyl-(2-hydroxycarbonyl)ethyl-ammonium)-2-propyloxy in position 2 [Compound 5];
Triiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=4-hydroxycarbonylphenoxy in position 2, and R 2 =[3-(N,N,N-trimethylammonium) phenoxy] in positions 9(10), 16(17), 23(24) [Compound 6];
Triiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=4-hydroxycarbonylphenoxy in position 2, and R 2 =[3-(N,N,N-trimethylammonium) phenoxy]iodide in positions 8(11), 15(18), 22(25) [Compound 7];
Tetraiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=R 2 =[3-(N,N,N-trimethylammonium)phenoxy] in positions 2,9(10), 16(17), 23(24) [Compound 8];
Tetrachloride of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=R 2 =[3-(N,N,N-trimethylammonium)phenoxy] in positions 1, 8(11), 15(18), 22(25) [Compound 9];
Tetrachloride of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=R 2 =[4-(N,N,N-trimethylammonium)phenoxy] in positions 1, 8(11), 15(18), 22(25) [Compound 10];
Octachloride of phthalocyanine derivative of formula (I) in which M is Zn, R=R 1 =R 2 =R 3 =[3-(N,N,N-trimethylammonium)phenoxy] in positions 2,3,9,10,16,17,23,24 [Compound 11]; and
Octachloride of the phthalocyanine derivative of formula (I) in which M is Zn, R=R 1 =R 2 =R 3 =[3-(N,N,N-methyldiethylammonium)phenoxy] in positions 2,3,9,10,16,17,23,24 [Compound 12].
2. The polymeric product according to claim 1 , wherein said polymer is mixed with or coated with a polymer soluble in water or in biological fluids.
3. The polymeric product according to claim 2 , wherein said polymer is selected from the group consisting of viscose, polystyrene, polyethylene, polypropylene, polyacrylamide, polyamide, polyvinyl alcohol, polysaccharides, cellulose esters, cellulose acetate, silicon derivatives and mixtures thereof.
4. The polymeric product according to claim 2 , wherein said soluble polymer is selected from the group consisting of dextrans and their derivatives, proteins and their methylated derivatives, and protein hydrolysates.
5. The polymeric product according to claim 1 , wherein said spacer comes from the linkage of said phthalocyanine derivative and said polymer by a suitable bifunctional agent selected from the group consisting of carbodiimides, glutaraldehyde, 1,1′-carbonyldiimidazole chlorotriazine, cyanogen bromide, mixed anhydrides, imidoesters and maleimido derivatives.
6. Self-sterilizing industrial and medical articles and devices produced or coated with the polymeric product as defined in claim 1 .
7. Articles and devices according to claim 6 in combination with one or more pharmaceutically active substances.
8. Articles and devices according to claim 6 having at least one surface coated with the polymeric product.
9. Articles and devices according to claim 6 , selected from the group consisting of catheters, guide tubes, probes, cardiac valves, prostheses for soft tissues, prostheses of animal origin, artificial tendons, bone and cardiovascular replacements, contact lenses, blood oxygenators, artificial kidneys, hearts, pancreases and livers, blood bags, syringes, surgical instruments, filter systems, laboratory instruments, containers for cultures and for cellular and tissue regeneration, supports for peptides, proteins and antibodies, clinical aids for domestic and hospital use, containers and instruments for cosmetic use.
10. The polymeric product according to claim 1 , wherein said polymer is selected from the group consisting of viscose, polystyrene, polyethylene, polypropylene, polyacrylamide, polyamide, polyvinyl alcohol, polysaccharides, cellulose esters, cellulose acetate, silicon derivatives and mixtures thereof.
11. The polymeric product of claim 1 , wherein said phthalocyanine derivative of formula I is selected from the group of compounds consisting of:
Diiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 2 =R 3 =H, and R=1,3-bis-(trimethylammonium)-2-propyloxy in position 2[Compound 1];
Tetraiodide of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=R 2 =[3-(N,N,N-trimethylammonium)phenoxy] in positions 2, 9(10), 16(17), 23(24) [Compound 8]; and
Tetrachloride of the phthalocyanine derivative of formula (I) in which M is Zn, R 1 =R 3 =H, R=R 2 =[3-(N,N,N-trimethylammonium)phenoxy] in positions 1, 8(11), 15(18), 22(25) [Compound 9].