Azlactone-functional hydrophilic coatings and hydrogels
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08C-026/02
C08C-126/06
출원번호
US-0860944
(2001-05-18)
발명자
/ 주소
Haddad, Louis C.
Hembre, James I.
Rasmussen, Jerald K.
Sarpong, Daniel
출원인 / 주소
3M Innovative Properties Company
대리인 / 주소
Gram Christopher D.
인용정보
피인용 횟수 :
9인용 특허 :
12
초록
Surface coatings including azlactone-functional hydrogels and articles with the coatings disposed thereon are disclosed. Methods of making the coating and controlling the gellation time of the hydrogels are also disclosed.
대표청구항▼
1. A material comprising:at least one azlactone-functional copolymer comprising a plurality of azlactone moieties and a plurality of azlactone functional groups, wherein the copolymer is derived from monomers comprising at least one alkenyl azlactone monomer and at least one hydrophilic or water sol
1. A material comprising:at least one azlactone-functional copolymer comprising a plurality of azlactone moieties and a plurality of azlactone functional groups, wherein the copolymer is derived from monomers comprising at least one alkenyl azlactone monomer and at least one hydrophilic or water soluble comonomer;a first crosslinker comprising a first nucleophilic moiety and a second thermally reactive moiety; andoptionally, a second crosslinker comprising a first nucleophilic moiety and a second thermally reactive moiety;wherein:a) the first moiety of the first crosslinker is covalently bound to a first azlactone moiety; andb) the second moiety of the first crosslinker is covalently bound to i) a second azlactone moiety or ii) the second moiety of the second crosslinker, with the first moiety of the second crosslinker being bound to the second azlactone moiety; andwherein the material is a crosslinked hydrogel. 2. The material of claim 1 wherein the second moiety of the first crosslinker is covalently bound to the second azlactone moiety. 3. The material of claim 2 wherein the first crosslinker is a primary polyamine. 4. The material of claim 3 wherein the primary polyamine is ethylenediamine; 1,3-propaziediamine; 1,3-diamino-2-hydroxypropane; 1,6-hexanediamine; or tris-(2-aminoethyl)amine. 5. The material of claim 2 wherein the first crosslinker is a polyetherpolyamine. 6. The material of claim 5 wherein the polyetherpolyamine is 4,7, 10-trioxa-1, 13-tridecanediamine; 3,6-dioxa-1,8-diaminooctane; an amine-terminated polyethyleneglycol homopolymer; an amine-terminated polyethyleneglycol copolymer; an amine-terminated polypropyleneglycol homopolymer; or an amine-terminated polypropyleneglycol copolymer. 7. The material of claim 2 wherein the first crosslinker is a compound comprising a primary amine-containing functional group and at least one secondary amine-containing functional group (i.e., a 1°/2° amine-containing compound). 8. The material of claim 7 wherein the 1°/2° amine-containing compound is N-methyl-1,2-ethanediamine; N-ethyl-1,2-ethanediamine; or N-isopropyl-1,2-ethanediamine. 9. The material of claim 1 wherein the second moiety of the first crosslinker is covalently bound to the second moiety of the second crosslinker. 10. The material of claim 9 wherein the first crosslinker and the second crosslinker have the same chemical structure. 11. The material of claim 9 wherein the first crosslinker and the second crosslinker have different chemical structures. 12. The material of claim 9 wherein at least one of the first crosslinker or the second crosslinker comprises at least two moieties that are different from one another (i.e., a heterobifunctional crosslinker). 13. The material of claim 12 wherein the heterobifunctional crosslinker is an aminoalkylmonoalkoxysilane, an aminoalkyldialkoxysilane, or an aminoalkyltrialkoxysilane. 14. The material of claim 12 wherein the heterobifunctional crosslinker is 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, or N-[3-(trimethoxysilyl)propyl]ethylenediamine. 15. The material of claim 1 wherein the at least one hydrophilic or water soluble comonomer is an acrylamide, a methacrylamide, an N-monosubstituted acrylamide, an N,N-disubstituted acrylamide, an N-monosubstituted methacrylamide, an N,N-disubstituted methacrylamide, an N-vinylamide or a hydroxyalkylacrylate. 16. The material of claim 1 wherein the at least one hydrophilic or water soluble comonomer is an ionic comonomer. 17. The material of claim 16 wherein the ionic comonomer is acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, vinyl phosphoric acid, vinyl phosphonic acid, styrenesulfonic acid, 2-acrylamido-2-methyl-1-propanesulfonic acid, 2-vinylpyridine, 3-vinylpyridine, 4-vinylpyridine, (3-acrylamidopropyl)trimethylammonium chloride, 2-diethylaminoethylacrylate, 2-diethylaminoethylmethacrylate, 3-dimethylaminopropylacrylate, or 3-dimethylaminopropylmethacrylate. 18. The material of claim 1 wherein the monomers further comprise at least one non-hydrophilic comonomer. 19. The material of claim 18 wherein the at least one non-hydrophilic comonomer is a free radically polymerizable monomer. 20. The material of claim 19 wherein the free radically polymerizable monomer is an acrylate ester, a methacrylate ester, or a styrene. 21. The material of claim 18 wherein the monomers comprise less than about 50% non-hydrophilic monomer, by weight. 22. The material of claim 21 wherein the monomers comprise less than about 30% non-hydrophilic monomer, by weight. 23. The material of claim 1 wherein the chemical structure of the second moiety of the first crosslinker is the same as the chemical structure of the first moiety of the first crosslinker. 24. The material of claim 1 wherein the chemical structure of the second moiety of the first crosslinker is different than the chemical structure of the first moiety of the first crosslinker. 25. The material of claim 1 wherein the chemical structure of the second moiety of the second crosslinker is the same as the chemical structure of the first moiety of the second cross linker. 26. The material of claim 1 wherein the chemical structure of the second moiety of the second crosslinker is different than the chemical structure of the first moiety of the second crosslinker. 27. A method of making a crosslinked hydrogel comprising:preparing at least one azlactone-functional copolymer comprising a plurality of azlactone functional groups, wherein the copolymer is derived from monomers comprising at least one alkenyl azlactone monomer and at least one hydrophilic or water soluble comonomer;diluting the azlactone-functional copolymer in an organic solvent;adding a first crosslinker comprising a first nucleophilic functional group and a second thermally reactive functional group to the aziactone-functional copolymer;optionally, adding a second crosslinker comprising a first nucleophilic functional group and a second thermally reactive functional group to the azlactone-functional copolymer;allowing the first functional group of the first crosslinker to covalently bind to a first azlactone functional group; andallowing the second functional group of the first crosslinker to covalently bind to i) a second azlactone functional group or ii) the second functional group of the second crosslinker, with the first functional group of the second crosslinker being bound to the second azlactone functional group, to form a crosslinked hydrogel. 28. The method of claim 27 wherein the first crosslinker and the second crosslinker have the same chemical structure. 29. The method of claim 27 wherein the first crosslinker and the second crosslinker have different chemical structures. 30. The method of claim 27 wherein the chemical structure of the second functional group of the first crosslinker is the same as the chemical structure of the first functional group of the first crosslinker. 31. The method of claim 27 wherein the chemical structure of the second functional group of the first crosslinker is different than the chemical structure of the first functional group of the first crosslinker. 32. The method of claim 27 wherein the chemical structure of the second functional group of the second crosslinker is the same as the chemical structure of the first functional group of the second crosslinker. 33. The method of claim 27 wherein the chemical structure of the second functional group of the second crosslinker is different than the chemical structure of the first functional group of the second crosslinker. 34. A method of controlling gellation time of a material comprising:providing a solution of an azlactone-functional copolymer comprising a plurality of azlactone functional groups, wherein the copolymer is derived from monomers comprising at least one alkenyl azlactone monomer and at least one hydrophilic or water soluble comonomer;selecting a first crosslinker comprising a first nucleophilic functional group and a second thermally reactive functional group, wherein the chemical structure of the second functional group is different than the chemical structure of the first functional group;optionally, selecting a second crosslinker comprising a first nucleophilic functional group and a second thermally reactive functional group, wherein the chemical structure of the second functional group is different than the chemical structure of the first functional group;adding the selected first crosslinker and, optionally, the selectcd second crosslinker to the solution;providing reaction conditions that allow the first functional group of the first crosslinker to covalently bind with a first azlactone functional group; andchanging the reaction conditions to allow the second functional group of the first crosslinker to covalently bind to i) a second azlactone functional group or ii) the second functional group of the second crosslinker, with the first functional group of the second corsslinker being bound to the second azlactone functional group, to form a crosslinked hydrogel. 35. The method of claim 34 wherein the second functional group of the first crosslinker covalently binds to the second azlactone functional group. 36. The method of claim 35 wherein the first crosslinker is a compound comprising a primary amine-containing functional group and at least one secondary amine-containing functional group (i.e., a 1°/2° amine-containing compound). 37. The method of claim 36 wherein the 1°/2° amine-containing compound is N-methyl-1,2-ethanediamine; N-ethyl-1,2-ethanediamine; or N-isopropyl-1,2-etbanediamine. 38. The method of claim 34 wherein the second functional group of the first crosslinker covalently binds to the second functional group of the second crosslinker. 39. The method of claim 38 wherein the first crosslinker and the second crosslinker have the same chemical structure. 40. The method of claim 34 wherein the first crosslinker and the second crosslinker have different chemical structures. 41. The method of claim 38 wherein at least one of the first crosslinker or the second crosslinker is an aminoalkylmonoalkoxysilane, an aminoalkyldialkoxysilane, or an aminoalkyltrialkoxysilane. 42. The method of claim 38 wherein at least one of the first crosslinker or the second crosslinker is 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, or N-[3-(trimethoxysilyl)propyl]ethylenediamine. 43. The method of claim 34 wherein the first crosslinker and the second crosslinker have the same chemical structure. 44. The method of claim 34 wherein the first crosslinker and the second crosslinker have different chemical structures.
연구과제 타임라인
LOADING...
LOADING...
LOADING...
LOADING...
LOADING...
이 특허에 인용된 특허 (12)
Moren Dean M. (North St. Paul MN) Heilmann Steven M. (Afton MN) Krepski Larry R. (White Bear Lake MN) Rasmussen Jerald K. (Stillwater MN), Azlactone Michael adducts.
Pegg Randall K. (Amelia Island FL) Saunders Mary S. (Monticello FL), Heterobifunctional crosslinked agents for immobilizing molecules on plastic substrates.
Heilmann Steven M. (Afton MN) Rasmussen Jerald K. (Stillwater MN) Krepski Larry R. (White Bear Lake MN) Milbrath Dean S. (Stillwater MN) Coleman Patrick L. (Minneapolis MN) Walker Margaret M. (Apple , Polymeric supports.
Gagnon David R. (St. Paul MN) Coleman Patrick L. (Minneapolis MN) Ortina Gary J. (Woodbury MN) Lyons Christopher S. (St. Paul MN) Milbrath Dean S. (West Lakeland Township ; Washington County MN) Rasm, Porous supports having azlactone-functional surfaces.
Burgoyne ; Jr. William F. (Allentown PA) Daniels Wiley E. (Easton PA) Sagl Dennis (Bethlehem PA) Lee Heueh-Chi (Allentown PA) Vratsanos Menas S. (Breinigsville PA), Process for coating low energy surfaces.
Heilmann Steven M. (North St. Paul MN) Palensky Frederick J. (St. Paul MN) Rasmussen Jerald K. (Stillwater MN), Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.