Hydrophilic polyurethanes of improved strength

• US 5,334,691 A
• Filed: 04/23/1992
• Issued: 08/02/1994
• Est. Priority Date: 07/24/1990
• Status: Expired due to Fees

• Current Assignee: Tyndale Plains-Hunter, Ltd.
• Original Assignee: Tyndale Plains-Hunter, Ltd.
• Inventors: Johnston, Christian W., Gould, Francis E.
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): Kulkosky, Peter F.
• Application Number:
  US07/872,893
• Time in Patent Office: 831 Days
• Field of Search: 528/76, 528/65, 521/159, 521/176, 424/409, 424/486, 424/501
• US Class Current: 528/76
• CPC Class Codes: A61L 15/26 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: C08G 18/302 Water
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/65 Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen C08G18/2805 takes precedence
• CPC Class Codes: C08G 18/6674 with compounds of group C08G18/3203
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The strength and integrity of hydrophilic polyurethane resins prepared by reacting a diol component, an organic chain extender and an organic diisocyanate are improved by critical selection of the diol component, the amount of water in the reaction mixture and the mole ratios of the reactants. The diol component is at least one of (1) a long chain poly(oxyethylene) glycol of molecular weight above 2500 and (2) a medium chain poly(oxyethylene) glycol or polyester glycol of 250-2500 molecular weight. The chain extender is a difunctional compound having a molecular weight of less than 250. The amount of water in the reaction mixture is 0.5 to 2.5 weight % and the urea content of the resins is from about 13.6 to 33.7 weight %. This invention also includes uses of these hydrophilic polyurethane resins as carrier vehicles for various active agents including a medicament, fungicide, pesticide, insecticide, fertilizer, fragrance, flavor, sun-screen, depilatory, cosmetic, contraceptive, anti-fogging agent, hair spray formulation and perfume.

Claims

1. A carrier system comprising an active agent the active agent is selected from a medicament, fungicide, pesticide, insecticide, fertilizer, fragrance, flavor, sun-screen, depilatory, cosmetic and a contraceptive and as a carrier vehicle therefor, a substantially non-covalently crosslinked hydrophilic substantially non-foaming polyurethane resin having improved tear strength and improved tensile strength and a urea content of from about 13.6 to 33.7 weight percent consisting essentially of the reaction product of a mixture of:

A. a diol component selected from at least one of

(1) a long chain poly(oxyethylene) glycol, having a molecular weight of from about 2500 to about 12,000

(2) a medium chain poly(oxyethylene) glycol or polyester glycol, having a molecular weight of from about 250 to about 2500,

B. at least one organic chain extender having a molecular weight of less than 250;

C. water; and

D. an organic diisocyanate;

wherein alternative mole ratios of the diol component A and water per mole of chain extender B are as follows;

(i) 0.4 to 0.5 of diol component (1), 1.5 to 10.0 of water;

(ii) 0.1 to 0.25 of diol component (2), 0.05 to 0.72 of water;

(iii) 0.25 to 0.50 of diol component (2), 0.25 to 1.00 of water;

(iv) 0.5 to 0.75 of diol component (2), 0.3 to 3.3 of water;

or

(v) 0.06 to 0.07 of diol component (1), 0.1 to 0.2 of diol component (2) and 0.25 to 1.25 of water;

wherein the effective NCO;

OH ratio is in the range of 0.85;

1 to 1.1;

1 and the amount of water in the reaction mixture is in the range of about 1 to about 2.5 wt. %.

2. A carrier system according to claim 1 wherein the hydrophilic polyurethane carrier vehicle is one wherein the diol component (A) comprises a long chain poly(oxyethylene) glycol having a number average molecular weight of about 5000 to 9000, and the chain extended (B) is diethylene glycol.

3. A carrier system according to claim 1 wherein the hydrophilic polyurethane carrier vehicle is one wherein the diol component (A) comprises a medium chain poly(oxyethylene) glycol and the claim extender (B) is diethylene glycol.

4. A carrier system according to claim 1 wherein the hydrophilic polyurethane carrier vehicle therefor is one wherein the diol component (A) comprises a mixture of a long chain poly(oxyethylene) glycol having a number average molecular weight of about 5000 to 9000 and a medium chain poly(oxyethylene) glycol, and the chain extender (B) is diethylene glycol.

6. The carrier system of claim 2 wherein the agent is a medicament.

7. The carrier system of claim 2 wherein the active agent is a medicament.

8. The carrier system of claim 2 wherein the active agent is a medicament.

5. A coating composition comprising substantially non-covalently crosslinked hydrophilic, substantially non-foaming polyurethane resin having improved tear strength and tensile strength and a urea content of from about 13.6 to 33.7 weight percent consisting essentially of the reaction product of a mixture of:

A. a diol component selected from at least one of

(1) a long chain poly(oxyethylene) glycol, having a molecular weight of from about 2500 to about 12,000

(2) a medium chain poly(oxyethylene) glycol or polyester glycol, having a molecular weight of from about 250 to about 2500,

B. at least one organic chain extender having a molecular weight of less than 250;

C. water; and

D. an organic diisocyanate;

wherein alternative mole ratios of the diol component A and water per mole of chain extender B are as follows;

(i) 0.4 to 0.5 of diol component (1), 1.5 to 10.0 of water;

(ii) 0.1 to 0.25 of diol component (2), 0.05 to 0.72 of water;

(iii) 0.25 to 0.50 of diol component (2), 0.25 to 1.00 of water;

(iv) 0.5 to 0.75 of diol component (2), 0.3 to 3.3 of water;

or

(v) 0.06 to 0.07 of diol component (1), 0.1 to 0.2 of diol component (2) and 0.25 to 1.25 of water;

wherein the effective NCO;

OH ratio is in the range of 0.85;

1 to 1.1;

1 and the amount of water in the reaction mixture is in the range of about 1 to about 2.5 wt. %, and an active agent selected from an anti-fogging agent, cosmetic, a hair spray formulation, a sun-screen and a perfume.