Non-fouling, wettable coated devices

Abstract

A device, and its production method, the device has a substrate and a coating composition, the coating composition being formed by the gas phase or plasma polymerization of a gas comprising at least one organic compound or monomer. The polymerization is carried out using a pulsed discharge having a duty cycle of less than about ⅕, in which the pulse-on time is less than about 100 msec and the pulse-off time is less than about 2000 msec. The duty cycle can also be varied, thus the coating composition can be gradient layered accordingly. The device has a coating composition which is uniform in thickness, pin-hole free, optically transparent in the visible region of the magnetic spectrum, permeable to oxygen, abrasive resistant, wettable and biologically non-fouling.

1 . A device comprising a substrate and a coating composition, said coating composition being formed by the gas phase polymerization of a gas comprising at least one organic compound, said gas phase polymerization being pulsed, having a duty cycle of less than about ⅕, in which the pulse-on time is less than about 100 msec and the pulse-off time is less than about 2000 msec, and said organic compound having the following structure:  
       
         
           
           
               
               
           
         
         m=0-1; n=0-6, 
 where Y represents C═O; 
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and R 7  each independently represents:  
 HX  
 OH,  
 halogen,  
 C 1 -C 4  alkyl,  
 C 1 -C 4  alkene,  
 C 1 -C 4  diene,  
 C 1 -C 4 alkyne,  
 C 1 -C 4  alkoxy, or  
 C 1 -C 4  alkyl halide; and  
 
 R 8  represents: 
 H,  
 halogen,  
 C 1 -C 4  alkyl,  
 C 1 -C 4  alkene,  
 C 1 -C 4  diene,  
 C 1 -C 4  alkyne,  
 C 1 -C 4  alkyl halide,  
 C 1 -C 4  aldehyde,  
 C 1 -C 4  ketone,  
 C 1 -C 4  epoxide,  
 C 1 -C 4  carboxylic acid,  
 C 1 -C 4  ester,  
 —CH═CHR 9 , where R 9  is H, halogen, C 1 -C 4  alkyl, C 1 -C 4  alkyl halide, C 1 -C 4  aldehyde, C 1 -C 4  ketone, C 1 -C 4  alkoxyl, C 1 -C 4  epoxide, C 1 -C 4  carboxylic acid, or C 1 -C 4  ester, or  
 —OR 10 , where R 10  is H, halogen, C 1 -C 4  alkyl, C 1 -C 4  alkene, C 1 -C 4  diene, C 1 -C 4  alkyne, C 1 -C 4  alkyl halide, C 1 -C 4  aldehyde, C 1 -C 4  ketone, C 1 -C 4  epoxide, C 1 -C 4  carboxylic acid, or C 1 -C 4  ester.  
 
 
       
     
     
         2 . The device of  claim 1 , wherein said organic compound is selected from the group of consisting of the following structural formulas:  
       R′C(R″)═C(R′″)—(OCH 2 CH 2 ) n —OR″″ and R′C(R″)═C(R″)—(OCH 2 CH 2 )—R″″ 
       where R′, R″, R′″, and R″″ each independently represents H, a linear or branched alkyl having 1 to 5 carbons; and n is 1 to 5.  
     
     
         3 . The device of  claim 1 , wherein said duty cycle is from about 1/10 to about 1/1000, and the pulse-on time is from about 1 μsec to about 100 msec, and the pulse-off time is from about 10 μsec to about 2000 msec.  
     
     
         4 . The device of  claim 1 , wherein said organic compound is di(ethylene glycol) vinyl ether, di(ethylene glycol) divinyl ether, or di(ethylene glycol) methyl vinyl ether.  
     
     
         5 . The device of  claim 1 , wherein said substrate is a contact lens.  
     
     
         6 . The device of  claim 1 , wherein said gas phase polymerization is high voltage discharge, radio frequency, microwave; ionizing radiation induced plasma polymerization; or photo induced polymerization; or a combination thereof.  
     
     
         7 . The device of  claim 1 , wherein said coating compositor is gradient layered by systematically decreasing the duty cycle of said gas phase polymerization.  
     
     
         8 . A device comprising a substrate and a coating composition, said coating composition being formed by the gas phase polymerization of a gas comprising at least one organic compound, said gas phase polymerization being pulsed, having a variable duty cycle each being of less than about ⅕, in which the pulse-on time is less than about 100 msec and the pulse-off time is less than about 2000 msec, and said organic compound having the following structure:  
       
         
           
           
               
               
           
         
         m=0-1; n=0-6,  
         where Y represents C═O; 
 R 1 , R 2 , R 3 , R 5 , R 6  and R 7  each independently represents: 
 H,  
 OH,  
 halogen,  
 C 1 -C 4  alkyl,  
 C 1 -C 4  alkene,  
 C 1 -C 4  diene,  
 C 1 -C 4  alkyne,  
 C 1 -C 4  alkoxy, or  
 C 1 -C 4  alkyl halide; and  
 
 R 8  represents: 
 H,  
 halogen,  
 C 1 -C 4  alkyl,  
 C 1 -C 4  alkene,  
 C 1 -C 4  diene,  
 C 1 -C 4  alkyne,  
 C 1 -C 4  alkyl halide,  
 C 1 -C 4  aldehyde,  
 C 1 -C 4  ketone,  
 C 1 -C 4  epoxide,  
 C 1 -C 4  carboxylic acid,  
 C 1 -C 4  ester,  
 —CH═CHR 9 , where R 9  is H, halogen, C 1 -C 4  alkyl, C 1 -C 4  alkyl halide, C 1 -C 4  aldehyde, C 1 -C 4  ketone, C 1 -C 4  alkoxyl, C 1 -C 4  epoxide, C 1 -C 4  carboxylic acid, or C 1 -C 4  ester, or  
 —OR 10 , where R 10  is H, halogen, C 1 -C 4  alkyl, C 1 -C 4  alkene, C 1 -C 4  diene, C 1 -C 4  alkyne, C 1 -C 4  alkyl halide, C 1 -C 4  aldehyde, C 1 -C 4  ketone, C 1 -C 4  epoxide, C 1 -C 4  carboxylic acid, or C 1 -C 4  ester.  
 
 
       
     
     
         9 . The device of  claim 8 , wherein said organic compound is selected from the group of consisting of the following structural formulas:  
       R′C(R″)═C(R′″)—(OCH 2 CH 2 ) n —OR″″ and R′C(R″)═C(R′″)—(OCH 2 CH 2 ) n —R″″ 
       where R′, R″, R′″, and R″″ each independently represents H, a linear or branched alkyl having 1 to 5 carbons; and n is 1 to 5.  
     
     
         10 . The device of  claim 8 , wherein said duty cycles vary from about 1/10 to about 1/1000, and the pulse-on time varies from about 1 μsec to about 100 msec, and the pulse-off time varies from about 10 μsec to about 2000 msec.  
     
     
         11 . The device of  claim 8 , wherein said organic compound is di(ethylene glycol) vinyl ether, di(ethylene glycol) divinyl ether, or di(ethylene glycol) methyl vinyl ether.  
     
     
         12 . The device of  claim 8 , wherein said substrate is a contact lens.  
     
     
         13 . The device of  claim 8 , wherein said gas phase polymerization is high voltage discharge, radio frequency, microwave; ionizing radiation induced plasma polymerization; or photo induced polymerization; or a combination thereof.  
     
     
         14 . The device of  claim 8 , wherein said coating composition is gradient layered by systematically decreasing the duty cycle of said gas phase polymerization.  
     
     
         15 . A method for plasma depositing a coating to a solid substrate, said method comprising: subjecting an organic compound having carbon, hydrogen and oxygen elements and a vinyl moiety to a gas phase polymerization utilizing a pulsed discharge having a duty cycle of less than about ⅕, in which the pulse-on time is less than about 100 msec and the pulse-off time is less than about 2000 msec.  
     
     
         16 . The method of  claim 15 , wherein said duty cycle is from about 1/10 to about 1/1000, and the pulse-on time is from about 1 μsec to about 100 msec, and the pulse-off time is from about 10 μsec to about 2000 msec.  
     
     
         17 . The method of  claim 15 , wherein said organic organic compound is di(ethylene glycol) vinyl ether, di(ethylene glycol) divinyl ether, or di(ethylene glycol) methyl vinyl ether.  
     
     
         18 . The method of  claim 15 , wherein said substrate is a contact lens.  
     
     
         19 . The method of  claim 15 , wherein said gas phase polymerization is high voltage, radio frequency, microwave; ionizing radiation induced plasma polymerization; or photo induced polymerization; or a combination thereof.  
     
     
         20 . The method of  claim 15 , wherein said pulsed discharge comprises a series of variable duty cycle.  
     
     
         21 . The method of  claim 15 , wherein said organic compound further having a halogen element.  
     
     
         22 . The device prepared by the method of  claim 15.