Patent EA-004863-B1 (EA)
Title: Hydrophilic macromolecular compounds
Inventor: HODD KENNETH A
IPC: C08F218/10
Filed: 2000-03-16
Abstract: 1. Macromolecular hydrophilic photocrosslinkers having a general formula (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and the unit C carries a photoactive group; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; and the photoactive group is linked to the ethylene groups of units C by a linking group comprising a group having the structure -O-C(O)-NH-, wherein said photoactive groups are exposed to light of determined wavelengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 2. Macromolecular hydrophilic photocrosslinkers according to claim 1 wherein the linking group has the structure of -O-C(O)-NH-Ph-, wherein Ph denotes an optionally substituted phenylene group. 3. Macromolecular hydrophilic photocrosslinkers having a general formula (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and the unit C carries a photoactive group; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; wherein the ethylene units A, B, C of the macromolecular structure comprises substituents in accordance with: A=-CH2-C(R<1>R<2>)-, B=-CH2-C(R<1>R<3>)-, C=-CH2-C(R<1>R<4>)-, wherein R<1> is hydrogen or methyl; R<2> and R<3> is-CON(Me)2, -CO2CH2CH2OH, -OCOCH3, -OCOCH2CH2Ph, -OH or a lactam group; with the proviso that R<2> and R<3> are not the same unless R<2> and R<3> is -OH; and R<4> is -R<5>P(O)R<6>OC(O)R<7>, wherein R<5>, R<6> and R<7> are selected among same or different aryl groups comprising phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, methylolphenyl, dimethylolphenyl, trimethylolphenyl or styryl radicals, wherein said photoactive groups are exposed to light of determined wavelengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 4. Photocrosslinkers according to claim 3, wherein R<2> and R<3> are selected so as to form a water-soluble molecule. 5. Photocrosslinkers according to claim 3, wherein said lactam units together with units A or B constitute N-vinylpyrrolidone units. 6. Photocrosslinkers according to claim 3, wherein at least one of R<2> and R<3> is hydroxyl. 7. Photocrosslinkers according to claim 3, wherein A is N-vinylpyrrolidone, B is vinyl alcohol. 8. Macromolecular hydrophilic photocrosslinkers having a general formula (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and the unit C carries a photoactive group; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; wherein the ethylene units A, B, C of the macromolecular structure comprises substituents in accordance with: A=-CH2-C(R<1>R<2>)-, B=-CH2-C(R<1>R<3>)-, C=-CH2-C(R<1>R<4>)-, wherein R<1> is hydrogen or methyl; R<2> and R<3> is -CON(Me)2, -CO2CH2CH2OH, -OCOCH3, -OCOCH2CH2Ph, -OH or a lactam group; with the proviso that R<2> and R<3> are not the same unless R<2> and R<3> is -OH; and R<4> is -R<8>C(O)P(O)R<9>R<10>, wherein R<8> ( -O-C(O)-NH-R<11>, wherein R<9>, R<10> and R<11> are selected among same or different aryl groups comprising phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, methylolphenyl, dimethylolphenyl, trimethylolphenyl or styryl radicals, wherein said photoactive groups are exposed to light of determined wavelengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 9. Macromolecular hydrophilic photocrosslinkers according to claim 8, wherein A and B are units of copolymers formed by N-vinylpyrrolidone and vinyl alcohol and C is 4-isocyanatobenzoyldiphenylphosphineoxide. 10. Macromolecular hydrophilic photocrosslinkers according to claim 8, wherein A and B are units of copolymers formed by N-vinylpyrrolidone and vinyl alcohol and C is 4-isocyanato-3,5-dimethylbenzoyldiphenylphosphineoxide. 11. Macromolecular hydrophilic photocrosslinkers according to claim 8, wherein R<2> and R<3> are selected so as to form a water-soluble molecule. 12. Macromolecular hydrophilic photocrosslinkers according to any one of claims 1-9, wherein said photocrosslinkers comprise functional groups for crosslinking. 13. Macromolecular hydrophilic photocrosslinkers according to claim 12, wherein said photocrosslinkers comprise functional groups are selected from vinyl, acryl or methacryl groups. 14. Macromolecular hydrophilic photocrosslinkers having a general formula (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and the unit C is a photoactive group, which is acyl- or aroylphosphineoxide and wherein A is N-vinylpyrrolidone and B is vinyl alcohol.; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; wherein said photoactive groups are exposed to light of determined wavelengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 15. Macromolecular hydrophilic photocrosslinkers having a general formula (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and wherein A is N-vinylpyrrolidone and B is vinyl alcohol which is hydrolyzed to vinyl alcohol and the unit C is 4-vinylbenzoyldiphenylphosphineoxide (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; wherein said photoactive groups are exposed to light of determined wave lengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 16. Macromolecular hydrophilic photocrosslinkers having a general formula (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and wherein A is N-vinylpyrrolidone and B 2-hydroxyethylmethacrilate and the unit C is 4-vinylbenzoyldiphenylphosphineoxide; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; wherein said photoactive groups are exposed to light of determined wavelengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 17. Macromolecular hydrophilic photocrosslinkers having a general formula (A) n (B) m, (C) p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and wherein A or B is N,N-dimethylacrilamide, and the unit C is selected from 4-vinylbenzoyldiphenylphosphineoxide, 4-vinyl-2,6-dimethylbenzoyldiphenylphosphineoxide and 1,3,5-trimethylbenzoylstyrylphenylphosphineoxide; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; wherein said photoactive groups are exposed to light of determined wavelengths above 305 nm, radicals are generated and retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. 18. An aqueous composition, wherein comprises a macromolecular hydrophilic photocrosslinkers according to any one of claims 1-17 and hydrophilic polymer carrying functional groups for crosslinking which are vinyl, acryl or methacryl groups or a combination thereof or at least one copolymerizable vinyl, acryl or methacryl monomer. 19. The aqueous composition according to claim 18, wherein comprises a macromolecular hydrophilic photocrosslinking agent according to claim 15 and 2-hydroxyethylmetacrilate. 20. The aqueous composition according to claim 18, wherein comprises a macromolecular hydrophilic photocrosslinking agent according to claim 17 and 2-hydroxyethylmetacrilate. 21. The aqueous composition according to any one of claims 8-10, wherein comprises a macromolecular hydrophilic photocrosslinking agent according to claim 15 and 2-hydroxyethylmetacrilate. 22. A composition according to claim 18 comprising 2-hydroxyethylmethacrilate and a macromolecular hydrophilic photocrosslinking agent according to any one of claims 15-17. 23. A method of preparing a photocrosslinker from a hydrophilic macromolecule (A)n(B)m(C)p capable of producing, upon exposure to light, crosslinked networks, wherein (i) A, B and C are units of substituted ethylene groups in the macromolecular structure; (ii) A, B and C are randomly distributed and the unit C carries a photoactive group; (iii) n = 0-98 mole %, m = 0-98 mole %, n+m = 50-98 mole % and p = 0.5-50 mole %; by reacting said macromolecule with an isocyanate substituted photoactive agent having the structure -C(O)=N-R<8>-C(O)P(O)R<9>R<10>, wherein R<8>, R<9>and R<10> are selected among same or different aryl groups comprising phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, methylolphenyl, dimethylolphenyl, trimethylolphenyl or styryl radicals. 24.