IONOMERS FOR IMPROVED COMPRESSION SET IN CERTAIN COPOLYMERS

• US 20110207897A1
• Filed: 12/17/2008
• Published: 08/25/2011
• Est. Priority Date: 12/20/2007
• Status: Abandoned Application

• Current Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Original Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Inventors: Kurczewski, Keith, Mccrba, Keith R., Ward, Robert S., Yang, Jim, Tian, Yuan
• Application Number:
  US12/809,217
• Publication Number:
  US 20110207897A1
• Time in Patent Office: Days
• US Class Current: 525/459
• CPC Class Codes: C08G 18/0828 containing sulfonate groups or groups forming them
• CPC Class Codes: C08G 18/288 Compounds containing at least one heteroatom other than oxygen or nitrogen
• CPC Class Codes: C08G 18/61 Polysiloxanes

Abstract

Block copolymer having improved compression set comprising 40-98 wt-% soft segment, 1.9-20 wt-% hard segment, and 0.05-3 wt-% monofunctional ionic endgroups. The incorporation of ionomers into diisocyanate-based thermoplastic polyurethane materials greatly improves compression set with little impact on the overall TPU formulation. A typical formulation for making the block copolymer contains 84.2% polydimethylsiloxane, 12.9% diisocyanate, 2.9% diamine chain extender, 0.15% sodium 2-[bis(2-hydroxyethyl)amino]ethylsulfonate, and 0.05% isethionic acid. The polymeric material may be configured, for instance, as a contact lens, prosthetic spinal nucleus, orthopedic bearing surface, gasket, or sealant.

Claims

1. A block copolymer having improved compression set comprising 40-98 wt % soft segment, 1.9-20 wt % hard segment, and 0.05-3 wt % monofunctional ionic endgroups which provide improved compression set in said block copolymer.

2. The block copolymer of claim 1, wherein said soft segment is made with a compound selected from aliphatic polyols of the group consisting of linear, branched, and graft polyarylene, polyalkylene, and polyalkenylene oxides, random and block copolymers thereof, polycarbonate polyols, hydroxyl-terminated silicones, random and block copolymers thereof with polyalkylene oxides, linear and branched polyalkenyl and polyalkylene polyols, and mixtures thereof.

3. The block copolymer of claim 1, wherein said soft segment is made from

NH₂(CH₂)₃—

Si(CH₃)₂'"'"'O—

[Si(CH₃)₂—

O]_n—

Si(CH₃)₂—

CH₂)₃NH₂

wherein n=0 to 500,

4. The block copolymer of claim 1, wherein the diisocyanate in the hard segment is made with a compound selected from the group consisting of alkyl diisocyanates, arylalkyldiisocyanates, alkyl-cycloalkyl diisocyanates, alkylaryl diisocyanates, cycloalkyl diisocyanates, aryl diisocyanates, and cycloalkylaryl diisocyanates, which may be further substituted with oxygen, and mixtures thereof.

5. The block copolymer of claim 4, wherein the hard segment is made from a cycloalkyl diisocyanate.

6. The block copolymer of claim 5, wherein the hard segment comprises isophorone diisocyanate.

7. The block copolymer of claim 1, wherein a chain extender is used to make up the hard segment, said chain extender being selected from the group consisting of alkylene, cycloalkylene, and arylene diols, triols, tetraalcohols, pentaalcohols, alkylene diamines, and mixtures thereof

8. The block copolymer of claim 1, wherein up to 50% of a chain extender used to make up the hard segment is made from a compound having the formula A-(CH)_m-N(BD)_n-(CH)_o-A wherein:

A is either OH or NH₂;

m, n, and o are integers ranging from 1 to 8;

B is an ionic functional group such as carboxylate, sulfonate, or phosphonate; and

D is an alkali metal.

9. The block copolymer of claim 1, having an ionic end group of the formula A-(CH₂)n-(BD)_m wherein:

A is either OH or NH₂;

n is an integer of 1 to 18;

B is an ionic functional group such as carboxylate, sulfonate, or phosphonate;

m is 1, 2, or 3; and

D is an alkali metal.

13. The polymeric material of claim 1, configured as a contact lens, prosthetic spinal nucleus, orthopedic bearing surface, gasket, or sealant.

10. A method of making a block copolymer having improved compression set, which method includes the steps of:

providing a reaction vessel containing an inert solvent,

rapidly adding to said solvent in said reaction vessel, in the absence of catalyst, an amino-terminated polydimethylsiloxane, an aliphatic diisocyanate, an ionic surface-modifying endgroup, and, optionally, an alkylene diol chain extender, at ambient temperature, and

removing the resulting polymer from the reaction vessel within 60 minutes of adding the reactants thereto.

11. The method of claim 10, wherein 0.05% to 0.5% sodium 2-hydroxyethylsulfonate is added to the solvent in the reaction vessel in order to provide the resulting polymer with ionomeric surface-modifying endgroups.

12. The method of claim 10, wherein said method is a method for making a polymer having improved compression set by bulk synthesis, which method comprises the step of:

metering into a twin-screw extruder

84.2% PDMS 3345

12.9% IPDI

2.9% DYTEK A

0.15% BES

0.05% isethionic acid

at 190°

C. with a screw speed 200 rpm.