Method for transformation of conventional and commercially important polymers into durable and rechargeable antimicrobial polymeric materials
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08K-005/34
C08K-005/00
C08K-005/3492
C08K-005/3435
출원번호
UP-0324616
(2006-01-03)
등록번호
US-7541398
(2009-07-01)
발명자
/ 주소
Sun, Yuyu
Chen, Zhaobin
출원인 / 주소
Board of Regents, The University of Texas System
대리인 / 주소
Flores, Edwin S.
인용정보
피인용 횟수 :
7인용 특허 :
28
초록▼
The present invention includes compositions and methods of making an antimicrobial polymer by mixing sterically hindered N-halo-amines with polymeric materials with a source of halides selected from sodium di-X-isocyanurate, sodium hypohalite, N--X-succinimide, and calcium hypohalite, and mixtures a
The present invention includes compositions and methods of making an antimicrobial polymer by mixing sterically hindered N-halo-amines with polymeric materials with a source of halides selected from sodium di-X-isocyanurate, sodium hypohalite, N--X-succinimide, and calcium hypohalite, and mixtures and combinations thereof, wherein X is selected from Cl or Br, and wherein the sterically hindered halo-amines are charged before or after mixing with the polymers, or combinations thereof.
대표청구항▼
What is claimed is: 1. An antimicrobial polymer additive comprising a sterically hindered N-halo-amine with a molecular weight higher than 350 g/mol, comprising the moiety of 2,2,6,6-tetramethyl-N-chloro-4-piperidinyl structure. 2. The additive of claim 1, wherein the sterically hindered N-halo-
What is claimed is: 1. An antimicrobial polymer additive comprising a sterically hindered N-halo-amine with a molecular weight higher than 350 g/mol, comprising the moiety of 2,2,6,6-tetramethyl-N-chloro-4-piperidinyl structure. 2. The additive of claim 1, wherein the sterically hindered N-halo-amine selected from the group consisting of: Bis(N--X-2,2,6,6-tetramethyl-4-piperidyl)sebacate; Poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-N--X-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidylimino]]; N--X-[(2,2,6, 6-tetramethyl-4-piperidyl)alkyl formate]; Poly[(6-morpholino-s-triazine-2,4-diyl)-N--X-[2, 2,6,6-tetramethyl-4-piperidyl]imino]-hexamethylene[(2,2,6,6-tetramethyl-4-piperidyl)imino]]; 3-Dodecyl-N--X-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide; 2,2,4,4-Tetramethyl-N--X-7-oxa-3,20-diazadispiro[5.1.11.2]-heneicosan-21-one; D-Glucitol, 1,3:2,4-bis-O--(N--X-2,2,6,6-tetramethyl-4-piperidinylidene); 1,1'-ethylenebis (N--X-3,3,5,5-tetramethyl-piperazinone); N--X-2,2,4,4-tetramethyl-7-oxa-20-(oxiranylmethyl)-3,20-diazadispiro[5.1. 11.2]henicosan-21-one; 1,2,3,4-Butanetetracarboxylic acid, polymer with β,β,β',β'-tetramethyl-2,4,8,10-tetraoxaspiro[5.5] undecane-3,9-diethanol, N--X-2,2,6,6-tetramethyl-4-piperidinyl ester; Poly[oxy[methyl[3-[N--X-(2,2,6,6-tetramethyl4-piperidinyl)-oxy]propyl] silylene]]; 1,1',1"-[1,3,5-Triazine-2,4-6-triyltris[(cyclohexylimino)ethylene]]tris (N--X-3,3,5,5-tetramethyl-piperazinone); and mixtures and combinations thereof, wherein X is Cl or Br or I. 3. The additive of claim 1, wherein the sterically hindered N-halo-amino comprises a source of halides is selected from: sodium di-X-isocyanurate, sodium hypohalite, N--X-succinimide, and calcium hypohalite, wherein X is selected from Cl or Br. 4. The additive of claim 1, wherein the antimicrobial polymer additive is mixed with polymeric materials prior to, during or after halogenation. 5. The additive of claim 1, wherein the antimicrobial polymer additive is antimicrobial against gram-negative bacteria, gram-positive bacteria, species that are drugs resistant and combinations or the thereof. 6. The additive of claim 1, wherein the antimicrobial polymer additive is with a polymer formed by extrusion, injection molding, hot pressing, coating, painting, solvent casting, mixtures and combinations thereof. 7. The additive of claim 1, wherein the polymer is formed into a bead, a film, a tube, a sheet, a thread, a suture, a gauze, a bandage, an adhesive bandage, a vessel, a container, a cistern, a filter, a membrane, a coating, a paint, fibers, yarn and combinations thereof. 8. A method of making an antimicrobial polymer comprising the steps of: forming a polymer with a sterically hindered amine comprising a (β,β,β', β'-tetramethyl-4-piperidyl) with a molecular weight of at least 350 g/mol; and exposing the polymer to a source of halide atoms. 9. The method of claim 8, wherein the sterically hindered amine is selected from: Bis(N--X-2,2,6,6-tetramethyl-4-piperidyl)sebacate; Poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-N--X-[(2,2, 6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6, 6-tetramethyl-4-piperidylimino]]; N--X-[(2,2,6,6-tetramethyl-4-piperidyl)alkyl formate]; Poly[(6-morpholino-s-triazine-2,4-diyl)-N--X-[2,2,6, 6-tetramethyl-4-piperidyl]imino]-hexamethylene[(2,2,6, 6-tetramethyl-4-piperidyl)imino]]; 3-Dodecyl-N--X-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide; 2,2,4,4-Tetramethyl-N--X-7-oxa-3,20-diazadispiro[5.1.11.2]-heneicosan-21-one; D-Glucitol, 1,3:2,4-bis-O--(N--X-2,2,6,6-tetramethyl-4-piperidinylidene); 1,1'-ethylenebis(N--X-3,3,5,5-tetramethyl-piperazinone); N--X-2,2,4,4-tetramethyl-7-oxa-20-(oxiranylmethyl)-3,20-diazadispiro[5.1. 11.2]henicosan-21-one; 1,2,3,4-Butanetetracarboxylic acid, polymer with β,β,β',β',-tetramethyl-2,4,8,10tetraoxaspiro[5.5] undecane-3,9-diethanol, N--X-2,2,6,6-tetramethyl-4-piperidinyl ester; Poly[oxy[methyl[3-[N--X-(2,2,6,6-tetramethyl4-piperidinyl)-oxy]propyl] silylene]]; 1,1',1"-[1,3,5-Triazine-2,4-6-triyltris[(cyclohexylimino)ethylene]]tris (N--X-3,3,5,5-tetramethyl-piperazinone); and mixtures and combinations thereof, wherein X is Cl or Br. 10. The method of claim 8, wherein antimicrobial polymer undergoes recharging by exposing a polymer comprising a sterically hindered amine with a source of halide atoms. 11. The method of claim 8, wherein the source of halides is selected from: sodium di-X-isocyanurate, sodium hypohalite, N--X-succinimide, and calcium hypohalite, wherein X is selected from Cl or Br. 12. The method of claim 8, wherein the antimicrobial polymer additive is antimicrobial against gram-negative bacteria, gram-positive bacteria, species that are drugs resistant and combinations or the thereof. 13. A method of making an antimicrobial polymer comprising the steps of: mixing a (β,β,β',β'-tetramethyl-4-piperidyl) sterically hindered amine with a with a molecular weight of at least 350 g/mol with a source of halide atoms to form a sterically hindered N-halo-amine; and forming a polymer in the presence of the sterically hindered N-halo-amine. 14. The method of claim 13, wherein the (β,β,β',β'-tetramethyl-4-piperidyl)sterically hindered amine is selected from: Bis(N--X-2,2,6,6-tetramethyl-4-piperidyl)sebacate; Poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-N--X-[(2,2, 6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6, 6-tetramethyl-4-piperidylimino]]; N--X-[(2,2,6,6-tetramethyl-4-piperidyl)alkyl formate]; Poly[(6-morpholino-s-triazine-2,4-diyl)-N--X-[2,2,6, 6-tetramethyl-4-piperidyl]imino]-hexamethylene[(2,2,6, 6-tetramethyl-4-piperidyl)imino]]; 3-Dodecyl-N--X-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide; 2,2,4,4-Tetramethyl-N--X-7-oxa-3,20-diazadispiro[5.1.11.2]-heneicosan-21-one; D-Glucitol, 1,3:2,4-bis-O--(N--X-2,2,6,6-tetramethyl-4-piperidinylidene); 1,1'-ethylenebis(N--X-3,3,5,5-tetramethyl-piperazinone); N--X-2,2,4,4-tetramethyl-7-oxa-20-(oxiranylmethyl)-3,20-diazadispiro[5.1. 11.2]henicosan-21-one; 1,2,3,4-Butanetetracarboxylic acid, polymer with β,β,β',β'-tetramethyl-2,4,8,10-tetraoxaspiro[5.5] undecane-3,9-diethanol, N--X-2,2,6,6-tetramethyl-4-piperidinyl ester; Poly[oxy[methyl[3-[N--X-(2,2,6,6-tetramethyl4-piperidinyl)-oxy]propyl] silylene]]; 1,1',1"-[1,3,5-Triazine-2,4-6-triyltris[(cyclohexylimino)ethylene]]tris (N--X-3,3,5,5-tetramethyl-piperazinone); and mixtures and combinations thereof, wherein X is Cl or Br. 15. The method of claim 13, wherein antimicrobial polymer undergoes recharging by exposing a polymer comprising a sterically hindered amine with a source of halide atoms. 16. The method of claim 13, wherein the source of halides is selected from: sodium di-X-isocyanurate, sodium hypohalite, N--X-succinimide, and calcium hypohalite, wherein X is selected from Cl or Br. 17. The method of claim 13, wherein the antimicrobial polymer additive is antimicrobial against gram-negative bacteria, gram-positive bacteria, species that are drugs resistant and combinations or the thereof. 18. A method of recharging an antimicrobial polymer comprising the steps of: exposing a polymer comprising a (β,β,β',β'-tetramethyl-4-piperidyl) sterically hindered amine with a with a molecular weight of at least 350 g/mol with a source of halide atoms. 19. The method of claim 18, wherein the (β,β,β',β'-tetramethyl-4-piperidyl) sterically hindered amine is selected from: Bis(N--X-2,2,6,6-tetramethyl-4-piperidyl) sebacate; Poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-N--X-[(2,2, 6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6, 6-tetramethyl-4-piperidylimino]]; N--X-[(2,2,6,6-tetramethyl-4-piperidyl)alkyl formate]; Poly[(6-morpholino-s-triazine-2,4-diyl)-N--X-[2,2,6, 6-tetramethyl-4-piperidyl]imino]-hexamethylene[(2,2,6, 6-tetramethyl-4-piperidyl)imino]]; 3-Dodecyl-N--X-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide; 2,2,4,4-Tetramethyl-N--X-7-oxa-3,20-diazadispiro[5.1.11.2]-heneicosan-21-one; D-Glucitol 1,3:2,4-bis-O--(N--X-2,2,6,6-tetramethyl-4-piperidinylidene); 1,1'-ethylenebis(N--X-3,3,5,5-tetramethyl-piperazinone); N--X-2,2,4,4-tetramethyl-7-oxa-20-(oxiranylmethyl)-3,20-diazadispiro[5.1. 11.2]henicosan-21-one; 1,2,3,4-Butanetetracarboxylic acid, polymer with β,β,β',β'-tetramethyl-2,4,8,10-tetraoxaspiro[5.5] undecane-3,9-diethanol, N--X-2,2,6,6-tetramethyl-4-piperidinyl ester; Poly[oxy[methyl[3-[N--X-(2,2,6,6-tetramethyl4-piperidinyl)-oxy]propyl] silylene]]; 1,1',1"-[1,3,5-Triazine-2,4-6-triyltris[(cyclohexylimino)ethylene]]tris (N--X-3,3,5,5-tetramethyl-piperazinone); and mixtures and combinations thereof, wherein X is Cl or Br. 20. The method of claim 18, wherein the source of halides is selected from: sodium di-X-isocyanurate, sodium hypohalite, N--X-succinimide, and calcium hypohalite, wherein X is selected from Cl or Br. 21. An antimicrobial polymer additive comprising a sterically hindered N-halo-amine comprising the moiety of 2,2,6,6-tetramethyl-N-chloro-4-piperidinyl structure with a molecular weight of at least 350 g/mol. 22. The additive of claim 21, wherein the sterically hindered N-halo-amine is selected from the group consisting of: Bis(N--X-2,2,6,6-tetramethyl-4-piperidyl) sebacate; Poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-N--X-[(2,2, 6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6, 6-tetramethyl-4-piperidylimino]]; N--X-[(2,2,6,6-tetramethyl-4-piperidyl)alkyl formate]; Poly[(6-morpholino-s-triazine-2,4-diyl)-N--X-[2,2,6, 6-tetramethyl-4-piperidyl]imino]-hexamethylene[(2,2,6, 6-tetramethyl-4-piperidyl)imino]]; 3-Dodecyl-N--X-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide; 2,2,4,4-Tetramethyl-N--X-7-oxa-3,20-diazadispiro[5.1.11.2]-heneicosan-21-one; D-Glucitol, 1,3:2,4-bis-O--(N--X-2,2,6,6-tetramethyl-4-piperidinylidene); 1,1'-ethylenebis(N--X-3,3,5,5-tetramethyl-piperazinone); N--X-2,2,4,4-tetramethyl-7-oxa-20-(oxiranylmethyl)-3,20-diazadispiro[5.1. 11.2]henicosan-21-one; 1,2,3,4-Butanetetracarboxylic acid, polymer with β,β,β',β"-tetramethyl-2,4,8,10-tetraoxaspiro[5.5] undecane-3,9-diethanol, N--X-2,2,6,6-tetramethyl-4-piperidinyl ester; Poly[oxy[methyl[3-[N--X-(2,2,6,6-tetramethyl4-piperidinyl)-oxy]propyl] silylene]]; 1,1',1"-[1,3,5-Triazine-2,4-6-triyltris[(cyclohexylimino)ethylene]]tris (N--X-3,3,5,5-tetramethyl-piperazinone); and mixtures and combinations thereof, wherein X is Cl or Br.
연구과제 타임라인
LOADING...
LOADING...
LOADING...
LOADING...
LOADING...
이 특허에 인용된 특허 (28)
Rasberger Michael (Allschwil CH), 3-Alkyl-4-oxo-imidazolidines and their 1-oxyls.
Li, Shulong, Method of retaining antimicrobial properties on a halamine-treated textile substrate while simultaneously reducing deleterious odor and skin irritation effects.
Shulong Li, Method of retaining antimicrobial properties on a halamine-treated textile substrate while simultaneously reducing deleterious odor and skin irritation effects.
Worley Shelby D. (Auburn AL) Sun Gang (Auburn AL) Sun Wanying (Lodi NJ) Chen Tay-Yuan (Auburn AL), Monomeric and polymeric cyclic amine and-halamine compounds.
Chu Daniel T. (Santa Clara CA) Li Qun (Gurnee IL) Cooper Curt S. (Gurnee IL) Fung Anthony K. L. (Gurnee IL) Lee Cheuk M. (Libertyville IL) Plattner Jacob J. (Libertyville IL), Quinolizinone type compounds.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.