Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2001-08-28
2003-09-30
Niland, Patrick D. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S474000, C524S476000, C524S485000, C524S486000, C524S589000, C524S590000
Reexamination Certificate
active
06627699
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to improved polyurethane formulations, particularly to polyurethane prepolymer formulations which have improved compatibility with process oils.
BACKGROUND OF THE INVENTION
During manufacture of polyurethane prepolymers such as those for rebonding of recycled flexible polyurethane foam crumb, a process oil such as naphthenic oil is included in the prepolymer formulation in amounts of about 5 to 50% by weight to lower the surface tension of the prepolymer, as well as to achieve a prepolymer that has a room temperature viscosity of about 300 to about 4000 cP.
The viscosity of the polyurethane prepolymer depends upon variables such as polyol functionality, polyol molecular weight, isocyanate functionality, isocyanate type, and isocyanate value of the prepolymer. The process oils provide an additional means for controlling the viscosity of the prepolymers.
The rebonding of flexible polyurethane foam crumb has traditionally been achieved by mixing the crumbs of recycled flexible foam with a liquid isocyanate terminated prepolymer blend containing a process oil. The prepolymers have conventionally been made from the reaction of TDI or MDI isocyanates and flexible polyether triols. The triols typically have molecular weights between about 300 and about 8000, and more typically from about 1000 to about 6000. They have nominal functionalities of 3. These flexible polyether polyols contribute essential flexibility to the adhesive bond. These polyols are based on propylene oxide or combinations of propylene oxide with minor amounts of ethylene oxide. The polyols are made by polyaddition of a trifunctional initiator species, most typically glycerol or trimethylolpropane, with the appropriate amounts of the alkylene oxide(s) in order to achieve the desired molecular weight in the final polyol. The resulting polyols are nominally trifunctional (triols). The technology for manufacturing these flexible polyether polyols, and derived isocyanate terminated prepolymers, is well known in the art.
Process oils which have been added to polyurethane prepolymer formulations include naphthenic, paraffinic, and aromatic oils. Aromatic oils have been the industry standard; aromatic oils, however, suffer the disadvantage of being labeled as possible carcinogens. Naphthenic and paraffinic oils, however, exhibit much lower compatibility in polyurethane prepolymer formulations than aromatic oils. As a result, prepolymer formulations which employ naphthenic and paraffinic oils tend to be less stable with respect to oil separation on storage than formulations which employ aromatic oils.
A need therefore exists for polyurethane formulations which have improved compatibility and/or solubility of oils such as naphthenic and paraffinic oils.
SUMMARY OF THE INVENTION
The invention relates to improved prepolymer formulations which include polyurethane prepolymers containing process oil, and optionally a compatibilizing agent provided in an effective amount to increase the solubility of the oil in the polyurethane prepolymer. The improved prepolymer formulations are useful, for example, as binder material for polyurethane foam crumb. It has now been unexpectedly and surprisingly discovered that the compatibility of the process oils, and particularly of the so called napthenic oils, can be significantly enhanced by using a flexible polyether diol, instead of a triol, to make the isocyanate terminated prepolymer.
The process of making the improved prepolymer formulations includes the steps of:
(a) providing an isocyanate terminated polyurethane prepolymer comprising the reaction product of a nominal polyether diol with a molar excess of organic polyfunctional isocyanate monomer (base isocyanate), said polyether diol having a number averaged terminal hydroxyl functionality of from 1.3 to 2.1 and being essentially free of other types of active hydrogen functionality;
(b) providing a process oil;
(c) optionally providing a compatibilizing agent for the process oil; and
(d) combining together the polyurethane prepolymer, process oil and optional compatibilizing agent.
DETAILED DESCRIPTION OF THE INVENTION
Glossary
1. ARCOL® F 3022 is a 3000 molecular weight polyether triol with a hydroxyl number of 56.0 and a nominal functionality of 3 from Lyondell Chemical Company;
2. Calsol 804 is a naphthenic oil from Calumet Lubricants Company with an aniline point of 63.3° C.;
3. Calsol 806 is a naphthenic oil from Calumet Lubricants Company with an aniline point of 69.4° C.;
4. Calsol 810 is a naphthenic oil from Calumet Lubricants Company with an aniline point of 72.2° C.;
5. Calsol 850 is a naphthenic oil from Calumet Lubricants Company with an aniline point of 80.0° C.;
6. Calsol 8240 is a naphthenic oil from Calument Lubricants Company with an aniline point of 85.6° C.;
7. Compatibilizing Agent means any material which will increase a process oil's compatibility in a polyurethane prepolymer, relative to what it would have been without the compatibilizing agent. Process oil compatibility in prepolymers, and quantification thereof, is defined in detail in the specification (below);
8. Corn oil is a mixture of triglycerides based on 10% palmitic acid, 5% stearic acid, 45% oleic, and 38% linoleic acid;
9. Cyclolube 310 N is a naphthenic oil from Golden Bear with an aniline point of 77.8° C.;
10. Calight RPO is naphthenic oil from Calumet Lubricants with an aniline point of 72.2° C.;
11. DABCO® 120 is a tin catalyst from Air Products, Inc.;
12. DABCO® T45 is a PIR (polyisocyanurate) catalyst from Air Product, Inc.;
13. Hyprene V100 (also available as Hyprene H100)is naphthenic oil from Ergon, Inc. with an aniline point of 72.8° C.;
14. Linseed oil is a mixture of triglycerides based on 6% palmitic acid, 3% stearic acid, 19% oleic acid, 24% linoleic acid, and 47% linolenic acid;
15. LG-168 is a 1000 molecular weight polyether triol from Lyondell Co.;
16. Palm kernal oil is a mixture of triglycerides based on 47% lauric acid, 9% palmitic acid, 1% stearic acid, 19% oleic acid, and 1% linoleic acid;
17. PPG425 is a 425 molecular weight polyether diol from Lyondell Co.;
18. PPG725 is a 725 molecular weight polyether diol from Lyondell Co.;
19. RUBINOL® F-456 is a 2000 molecular weight polyoxypropylene diol with a hydroxyl number of 56, a nominal functionality of 2, and 0% oxyethylene units; from Huntsman Polyurethanes;
20. RUBINOL® 455 is a 3,100 molecular weight polyoxypropylene-polyoxyethylene triol from Huntsman Polyurethanes; the triol contains 9% oxyethylene units, as a cap;
21. RUBINOL® F-459 is a polyoxypropylene-polyoxyethylene diol from Huntsman Polyurethanes with a hydroxyl number of 30, and containing 21% by wt. of oxyethylene units as a cap.
22. RUBINATE® M is polymeric MDI from Huntsman Polyurethanes with an isocyanate value of 31.5 and a functionality of 2.7;
23. RUBINATE® 9041, available from Huntsman Polyurethanes, is a blend of 75% RUBINATE® M and 25% of a blend of 4,4′MDI and 2,4′MDI;
24. RUBINATE® 9471, available from Huntsman Polyurethanes, is a blend of 60% RUBINATE® M and 40% of a blend of 4,4′MDI and 2,4′MDI and 0.14% HCl;
25. SHELLFLEX® 3251 is naphthenic oil from Shell Oil Products Co. with an aniline point of 85.6° C.;
26. SHELLFLEX® 6212 is naphthenic oil from Shell Oil Products Co. with an aniline point of 67.8;
27. Soya bean oil is a mixture of triglycerides based on 12% palmitic acid, 4% stearic acid, 21% oleic acid, 53% linoleic acid, and 7% linolenic acids;
28. Sundex 840 is an aromatic oil from Sun Oil Company with an aniline point of 15.7° C.;
29. Sunflower oil is a mixture of triglycerides based on 6% palmitic acid, 4% stearic acid, 18% oleic acid, and 72% linoleic acid;
30. SUNPAR® LW103 is a paraffinic oil from Sun Oil Company with an aniline point of 60.5° C.;
31. SUNPAR® LW104 is a paraffinic oil with an aniline point of 69.0° C.;
32. SUNPAR® LW105 is a paraffinic oil with an aniline point of 77.8° C.;
33. SUNPAR® LW107 is a paraffinic oil with an aniline point of 90.6° C.;
34. SUNPAR® LW110 is a paraffinic oil with an anilin
MacFarland David R.
MacFarland Marilyn
Sawitski, Jr. Robert G.
Graham Nicole
Huntsman International LLC
MacFarland Marilyn
Niland Patrick D.
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