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Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units, and use thereof

  • US 4,740,533 A
  • Filed: 07/28/1987
  • Issued: 04/26/1988
  • Est. Priority Date: 07/28/1987
  • Status: Expired due to Term
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Petitions
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Forward Citations
2
Assignments
First Claim
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1. An optically clear wettable, flexible, oxygen permeable, substantially non-swellable ophthalmic device fabricated from a polymer of a crosslinkable monomer having a segment S" of the formula



  • space="preserve" listing-type="equation">--(D--S'"'"'--L--D--A--L)--.sub.b                              (I'"'"')
whereinb is 1-10;

each D is independently --O-- or --NR21 --;

each L is independently --BRB'"'"'--, the terminal L group within any one monomer also being capable of being --BR--;

each S'"'"' is independently of the formula ##STR24## each A is independently of the formula ##STR25## the terminal oxygen atom in formulae II or III being replaceable with --NR21 --;

each R1 and R2 is independently lower alkyl or aryl;

 each R3, R4, R7 -R10, R13 -R16, R19 and R20 is independently selected from H, halogen, aliphatic, aromatic or heterocyclic containing radical selected from unsubstituted (C1 -C16) alkyl;

 substituted C1 -C16 alkyl;

 unsubstituted C2 -C16 alkenyl; and 

 substituted C2 -C16 alkenyl;

 wherein the alkyl and alkenyl substituents are independently selected from C1 -C16 alkoxycarbonyl, C2 -C16 alkenyloxycarbonyl, fluoro, aryl of up to 10 carbon atoms, C1 -C16 alkoxy, C2 -C16 alkanoyloxy, aryloxy of up to 10 carbon atoms, C2 -C6 alkenoyloxy, aroyl of up to 10 carbon atoms, aroyloxy of up to 11 carbon atoms, C3 -C8 cycloalkyl, C3 -C8 cycloalkyloxy, C3 -C8 cycloalkyl-carbonyloxy, C3 -C8 cycloalkoxy-carbonyl, oxacycloalkyl of up to 7 carbon atoms, oxacycloalkoxy of up to 7 carbon atoms, oxacycloalkoxy (up to 7 carbon atoms)-carbonyl, oxacycloalkyl (up to 7 carbon atoms)-carbonyloxy, and aryl (of up to 10 carbon atoms)-oxycarbonyl, each of said alkyl and alkenyl substituents being, in turn, optionally substituted by C1 -C6 alkyl, fluoro or a C1 -C6 alkoxy provided said last mentioned alkoxy is not bound to a carbon atom already singly bound to another oxygen atom;

 R3, R4, R7 -R10, R13 -R16, R19 and R20 being further independently selected from aryl of up to 10 carbon atoms, C3 -C8 cycloalkyl, and oxacycloalkyl of up to 7 carbon atoms, each of which may be unsubstituted or further substituted with a substituent selected from the group of substituents for said R3 alkyl set forth above;

 R5, R6, R11, R12, R17 and R18 are selected from the same group set forth above for R3 ; and 

 R5, R6, R11, R12, R17 and R18 are further independently selected from C1 -C16 alkoxycarbonyl, C2 -C16 alkanoyloxy, C2 -C16 alkenoxycarbonyl, and C3 -C16 alkenoyloxy, each of which is unsubstituted or further substituted by fluoro, aryl of up to 10 carbon atoms, or C1 -C16 alkoxy; and 

 R5, R6, R11, R12, R17 and R18 are still further independently selected from aryloxy of up to 10 carbon atoms, cycloalkoxy of up to 8 carbon atoms, cycloalkyl (of up to 8 carbon atoms)-carbonyloxy, cycloalkoxy (of up to 8 carbon atoms)-carbonyl, aroyloxy of up to 11 carbon atoms, oxacycloalkoxy of up to 7 carbon atoms, oxacycloalkenyloxy of up to 7 carbon atoms, oxacycloalkoxy (of up to 7 carbon atoms)-carbonyl, oxacycloalkyl (of up to 7 carbon atoms)-carbonyloxy, and aryloxy (of up to 10 carbon atoms)-carbonyl, each of which may be further substituted by fluoro, C1 -C6 alkyl or C1 -C6 alkoxy, provided that any substituent having a singly bound oxygen atom thereof as its link to the rest of the molecule may not be a substituent on the same carbon atom which is singly bonded to another oxygen atom; and 

 2 adjacent groups selected from R3 -R20, together with the atoms to which they are attached may form a 5-8 membered cycloalkyl, oxacycloalkyl or bicycloalkyl ring;

each f, g and h are independently 0-3;

each w, x and z is independently 0-200;

q is 1-100;

(w+x+z) times q in any single group A is 4-1000;

each n and m is independently 1-6;

each y is independently 2-75;

each R21 is independently H, C1 -C4 alkyl, or phenyl;

 each B and B'"'"' is independently ##STR26##  with the carbony in each case being bound to A, S'"'"', or D;

 each R is independently(i) a divalent aliphatic group of up to 25 carbon atoms which may be interrupted by oxy, carbonyloxy, amino, aminocarbonyl, oxycarbonyl, ureido, oxycarbonylamino, or carbonylamino;

(ii) a divalent 5-7 membered cycloaliphatic having 5-25 carbon atoms;

(iii) a divalent arylene group have 6-25, preferably 7-15 carbon atoms; and 

(iv) a divalent aralkyl or alkaryl having 7 to 25;

 wherein groups b and d can be optionally interrupted by the same groups as in group i and wherein the aryl rings in groups iii and iv may be further substituted with one or more substituents selected from halogen, C1 -C4 alkyl, and C1 -C12 perhalo alkyl;

 said device having a receding contact angle of less than 60%;

 being less than about 10% water in its swollen state; and 

 having a Dk (x10-10 mm ccO2 /cm.2 sec.mmHg) of at least about 7.
      

    

  

  
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