# US 5,708,118 A · Spandex elastomers

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- Number: US 5,708,118 A
- Document ID: US5708118A
- Status: Granted
- Kind: A
- Application number: 08/728,920
- Filed: 1996-10-11
- Granted: 1998-01-13
- Earliest claimed: 1996-10-11
- Assignees: Arco Chemical Technology, L.P.
- Inventors: Stephen D. Seneker; Bruce D. Lawrey
- Web page: https://patentgrep.com/patent/US5708118A

## CPC

- C08G 18/6674: {with compounds of group C08G18/3203}
- C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step
- C08G 18/4808: {Mixtures of two or more polyetherdiols}
- C08G 18/4854: {Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group}
- C08G 18/4866: {having a low unsaturation value}
- Y10S 528/906: Fiber or elastomer prepared from an isocyanate reactant
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Spandex-type segmented polyurethane/urea elastomers having exceptional elongation, hysteresis, recovery, and other physical properties are prepared by the amine chain extension of an isocyanate-terminated prepolymer prepared by the reaction of a stoichiometric excess of isocyanate with a polyol blend comprising a low molecular weight diol having a molecular weight below 750 Da with a high molecular weight glycol which may be a 1500 Da to 20,000 Da molecular weight, ultra-low unsaturation polyoxypropylene glycol with an unsaturation of less than about 0.010 meq/g.

## Claims

### Claim 1

An amine-extended, segmented polyurethane/urea spandex elastomer comprising the reaction product of:
an isocyanate-terminated prepolymer having a free NCO group content of from about 0.5 percent to about 8 percent by weight, said prepolymer comprising the reaction product of:
a) a stoichiometric excess of an isocyanate component comprising one or more diisocyanates;
b) a glycol component comprising,
b) i) a high molecular weight glycol component comprising in major part, one or more ultra-low unsaturation polyoxypropylene glycols individually having a molecular weight of between about 1500 Da and 20,000 Da and an unsaturation less than about 0.010 meq/g, and
b) ii) a low molecular weight diol having a molecular weight less than 750 Da, such that the average molecular weight of said glycol component is from about 1000 Da to 10,000 Da,
with
a chain extender comprising one or more aliphatic diamine and/or cycloaliphatic diamine chain extender(s), wherein prior to reaction with said diamine chain extender, said isocyanate-terminated prepolymer is dissolved in a polar aprotic solvent.

### Claim 2 (depends on 1)

The spandex elastomer of claim 1 wherein said polyoxypropylene glycol comprises a polyoxypropylene glycol having an unsaturation of about 0.007 meq/g or less.

### Claim 3 (depends on 1)

The spandex elastomer of claim 1 wherein said polyoxypropylene glycol comprises a polyoxypropylene glycol having an unsaturation of about 0.005 meq/g.

### Claim 4 (depends on 1)

The spandex elastomer of claim 1 wherein said glycol component has an average unsaturation less than about 0.010 meq/g.

### Claim 5 (depends on 1)

The elastomer of claim 1 wherein said low molecular weight diol has a molecular weight less than about 500 Da.

### Claim 6 (depends on 1)

The elastomer of claim 1 wherein said low molecular weight diol has a molecular weight less than about 200 Da.

### Claim 7 (depends on 1)

The spandex elastomer of claim 1 wherein at least one of said ultra-low unsaturation polyoxypropylene glycols has a molecular weight of from about 2000 Da to about 10,000 Da.

### Claim 8 (depends on 1)

The spandex elastomer of claim 1 wherein said chain extender comprises ethylene diamine.

### Claim 9 (depends on 1)

An amine-extended, segmented polyurethane/urea spandex elastomer of claim 1 comprising the reaction product of a diamine chain extender comprising one or more aliphatic diamines and/or cycloaliphatic diamines with an isocyanate-terminated prepolymer prepared by reacting a stoichiometric excess of an isocyanate component comprising one or more diisocyanates with a polyol blend comprising one or more high molecular weight ultra-low unsaturation polyoxypropylene glycols and one or more low molecular weight diols having a molecular weight below 750 Da, said ultra-low unsaturation polyoxypropylene glycol(s) having a molecular weight of from about 2000 Da to 10,000 Da and an unsaturation of about 0.007 meq/g or less, said blend having an average molecular weight of from about 1500 Da to about 3000 Da.

### Claim 10

A process for the preparation of an aliphatic diamine and/or cycloaliphatic diamine-extended, segmented polyurethane/urea spandex elastomer, comprising contacting one or more diamine chain extenders comprising one or more aliphatic diamines and/or cycloaliphatic diamines with a solution of an isocyanate-terminated prepolymer in an aprotic solvent, said isocyanate-terminated prepolymer comprising the reaction product of:
a) a stoichiometric excess of an isocyanate component comprising one or more diisocyananes;
b) a glycol component comprising,
b) i) a high molecular weight glycol component comprising in major part, one or more ultra-low unsaturation polyoxypropylene glycols having a molecular weight of between about 1500 Da and 20,000 Da and an unsaturation less than about 0.010 meq/g, and
b) ii) a low molecular weight diol having a molecular weight less than 750 Da, such that the average molecular weight of said glycol component is from about 1000 Da to 10,000 Da,
to form a diamine chain extended polyurethane/urea spandex elastomer polymer.

### Claim 11 (depends on 10)

The process of claim 10 wherein said step of contacting comprises addition of one or more aliphatic diamines and/or cycloaliphatic diamines to said solution of said isocyanate-terminated prepolymer in aprotic solvent.

### Claim 12 (depends on 11)

The process of claim 11 wherein said aliphatic diamines and/or cycloaliphatic diamines prior to said step of contacting are dissolved in a further amount of said aprotic solvent or a solvent miscible with said aprotic solvent.

### Claim 13 (depends on 10)

The process of claim 10 further comprising extruding said spandex elastomer polymer through a fiber forming spinnerette.

### Claim 14 (depends on 10)

The process of claim 10 wherein at least one of said ultra-low unsaturated polyoxypropylene diols has a molecular weight of between about 2000 Da and 10,000 Da, and wherein said low molecular weight diol has a molecular weight below about 200 Da.

### Claim 15 (depends on 10)

The process of claim 10 wherein said aliphatic diamine(s) and/or cycloaliphatic diamine(s) comprises in major part by weight ethylene diamine.

### Claim 16

A reaction spinning process for the production of an amine-extended, segmented polyurethane elastomer, comprising:
a) selecting an isocyanate-terminated prepolymer having a free NCO group content of from about 0.5 percent to about 8 percent by weight, said prepolymer comprising the reaction product of:
a stoichiometric excess of an isocyanate component comprising one or more diisocyanates; with
a glycol component comprising a high molecular weight glycol component comprising in major part, one or more ultra-low unsaturation polyoxypropylene glycols individually having a molecular weight of between about 1500 Da and 20,000 Da and an unsaturation less than about 0.010 meq/g, and
a low molecular weight diol having a molecular weight less than 750 Da, such that the average molecular weight of said glycol component is from about 1000 Da to 10,000 Da;
b) introducing the prepolymer selected in step (a) into a chain extender solution containing one or more aliphatic diamines and/or cycloaliphatic diamines dissolved in a volatile solvent;
c) withdrawing from said chain extender solution an amine-extended, segmented polyurethane/urea elastomer; and
d) volatilizing any residual volatile solvent contained in said amine-extended, segmented polyurethane elastomer.