Abstract: Highly active double metal cyanide (DMC) catalysts are disclosed. The catalysts comprise a DMC complex, and organic complexing agent, and from about 5 to about 80 wt. %, based on the amount of catalyst, of a polyether having a number average molecular weight less than about 500. The catalysts polymerize propylene oxide at a rate in excess of about 1 kg PO/g Co/min. at 100 ppm catalyst, based on the weight of finished polyether, at 105.degree. C. The catalysts, which are easy to prepare, give polyether polyols with exceptionally low unsaturation levels.
Abstract: A process for alkoxylating phenols is disclosed. The process comprises reacting a carbonyl-functionalized phenol with an alkylene oxide in the presence of a substantially non-crystalline double metal cyanide (DMC) catalyst. The process offers fast reaction times at low catalyst levels, reduced problems with condensation side reactions, and low-color, low-viscosity, low-polydispersity alkoxylated phenols. The process enables efficient preparation of alkoxylated carbonyl-functonalized phenols that are especially valuable in the surfactant industry.
Type:
Grant
Filed:
December 18, 1996
Date of Patent:
July 28, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Jianzhong Shen, Sujuan Ba, David M. Braunstein, Haven S. Kesling, Jr.
Abstract: A process for making substantially non-crystalline double metal cyanide (DMC) catalysts having improved activity and performance is disclosed. The process comprises using a metal salt having an alkalinity within the range of about 0.2 to about 2.0 wt. % as metal oxide based on the amount of metal salt to prepare the catalyst. Surprisingly, important polyol properties such as viscosity and unsaturation improve when the alkalinity of the metal salt used to make the DMC catalyst is properly controlled. The process allows catalyst producers to enjoy the benefits of substantially non-crystalline DMC catalysts even when relatively inexpensive, technical-grade metal salts are used to make the catalyst.
Type:
Grant
Filed:
March 13, 1997
Date of Patent:
July 21, 1998
Assignee:
ARCO Chemical Technology, L.P.
Inventors:
George Combs, Harry R. Hinney, Paul T. Bowman
Abstract: Highly active double metal cyanide (DMC) complex catalysts and methods for making them are disclosed. The catalysts contain less than about 0.2 moles of metal salt per mole of DMC compound in the catalyst, and unlike other highly active DMC catalysts, are substantially crystalline. Polyether polyols made from the catalysts have low unsaturation and are useful for making many types of polyurethane products.
Type:
Grant
Filed:
January 7, 1997
Date of Patent:
July 14, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Bi Le-Khac, Harry R. Hinney, Paul T. Bowman
Abstract: A low-cost way to modulate the reactivity and acid number of polyetherester thermoset resins is disclosed. "Beginning" and "end" methods for making dicyclopentadiene (DCPD)-modified polyetherester resins are described. The "beginning" method comprises first heating a polyether, DCPD, a diol, an insertion catalyst, and a carboxylic acid derivative to produce a mixture that contains the polyether and a DCPD-diol diester adduct. Increasing the temperature causes insertion of the DCPD-diol diester into the polyether to give a DCPD polyetherester resin. The "end" method reacts a polyetherester resin made by insertion with DCPD to give a DCPD polyetherester resin. Compared with DCPD polyester resins, those of the invention give more flexible thermosets. Compared with unmodified polyetherester resins, the DCPD polyetherester resins offer formulators more control over curing, which eliminates mold distortion and shrinking or cracking of thermoset parts.
Abstract: Double metal cyanide-catalyzed polyols are made by an improved process in which a starter is continuously added during polymerization of the epoxide. The process includes a continuously added starter (S.sub.c), and optionally, an initially charged starter (S.sub.i). The continuously added starter comprises at least about 2 equivalent percent of the total starter used. The process enables the use of water and low molecular weight polyol starters in DMC-catalyzed polyol synthesis. In addition, the process gives polyether polyols having reduced levels of high molecular weight polyol tail, which can adversely affect polyurethane foam processing.
Abstract: Oligomeric polyoxyalkylene polyethers are prepared by oxyalkylating a low molecular weight hydroxyl-functional starter molecule with one or more alkylene oxides in the presence of a solid, heterogeneous magnesium oxide catalyst. The catalyst is readily and rapidly removed by simple filtration to yield a polyether with minimal metal ion content suitable for use directly or as a starter molecule for further double metal cyanide complex catalyzed oxyalkylation.
Abstract: Processes for making storage-stable epoxy-capped polyetherester resins are disclosed. In one process, a polyetherester resin is first made by inserting a carboxylic acid derivative into a polyether. Reacting the resin with a capping agent gives an intermediate resin with a reduced content of free carboxylic acid groups. Finally, the intermediate resin reacts with an epoxy compound in the presence of a finishing catalyst under conditions effective to give an epoxy-capped resin. The resins have low weight average molecular weights (less than about 8000), narrow molecular weight distributions (less than 6), and low viscosities, making them an excellent choice for low-VOC formulations. The finishing catalyst helps to minimize resin viscosity drift and improves shelf stability. Curing the resins with a vinyl monomer gives thermosets with an excellent balance of physical properties, including excellent water resistance.
Type:
Grant
Filed:
November 10, 1997
Date of Patent:
June 23, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Gangfeng Cai, Daniel M. Trauth, Lau S. Yang
Abstract: Esterification of an ultra-low unsaturation polyoxy(higher)alkylene polyol with a dicarboxylic acid or reactive derivative thereof to form a poly(half ester) followed by capping the poly(half ester) with a capping agent capable of forming an amide linkage or ester linkage while retaining primary hydroxyl functionality, generates high primary hydroxyl content polyols with substantially retained hydrophile/lipophile balance and low polydispersity. Low color products having primary hydroxyl contents in excess of 80 equivalent percent may be routinely achieved.
Abstract: Processes for making poly(thioether ether)s and hydroxy-terminated poly(thioether ether)s are disclosed. The poly(thioether ether)s are made by bulk free-radical polymerization of diallyl ether and an aliphatic C.sub.2 -C.sub.10 dithiol. Liquid polymers are obtained when mixtures of two or more dithiols are used. Hydroxy-terminated products are obtained by reacting the poly(thioether ether)s with allyl alcohol under free-radical conditions.
Abstract: Improved double metal cyanide catalysts are disclosed. The substantially amorphous catalysts of the invention are more active for polymerizing epoxides than conventional DMC catalysts, which have a substantial crystalline component. Polyol products made with the catalysts are unusually clear, have exceptionally low unsaturations, and contain no detectable amount of low molecular weight polyol impurities. A method of making the improved DMC catalysts, which involves intimately combining the reactants, is also disclosed.
Abstract: Water-reducible resins, neutralized resins, and derivatized resins useful for water-borne and solvent-based coatings and inks, powder coatings, and anti-corrosive coatings are disclosed. The water-reducible resins are copolymers of a vinyl aromatic monomer, a propoxylated allyl alcohol, and an acrylic acid monomer. These low-molecular-weight resins uniquely contain both hydroxyl and acid functional groups, and allow controlled curing with a variety of crosslinkers in coating systems. Coatings of the invention are useful in many applications, e.g., automotive basecoats, industrial appliance coatings, and wood finishes.
Abstract: Elastomers exhibiting decreased demold times and improved green strength are prepared by reacting a di- or polyisocyanate with a monodisperse polyoxypropylene diol having ultra-low unsaturation, and preferably prepared by the double metal cyanide.t-butyl alcohol catalyzed polymerization of propylene oxide. Further improved demold times and elevated elastomer physical properties are made possible bythe use of multidisperse polyoxyalkylene polyether polyol blends having an overall unsaturation of less than 0.010 meq/g and a polydispersity of about 1.4 or greater.
Type:
Grant
Filed:
December 19, 1996
Date of Patent:
March 17, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
Abstract: This invention relates to a chemical reactor design which reduces localized zones of concentration in the reactor and accomplishes near perfect mixing conditions with the use of a series of plug flow capillary reactors. Due to the reactor design, the sequencing of reactions is improved and throughput increased.
Abstract: Spandex-type polyurethane/urea segmented elastomers with exceptional physical properties may be prepared by the aliphatic and/or cycloaliphatic diamine chain extension of a solution of isocyanate-terminated polyoxypropylene diol-derived prepolymer wherein the diol component comprises in major part an ultra-low unsaturation polyoxypropylene diol having an unsaturation of less than about 0.010 meq/g and a number average molecular weight greater than 2000 Da. The spandex polymers have commercially desirable percent set and are capable of exceeding the properties of the industry standard PTMEG elastomers in many respects, particularly in elongation and hysteresis.
Abstract: High resilience polyurethane foams having improved wet set properties are obtained by reacting an isocyanate with a polyol component consisting of a polyoxyalkylene polyol with a functionality of 6 or more and a polymer polyol whose base polyol is a polyoxyalkylene polyol with a functionality of 6 or more, both polyols having oxyethylene caps in amounts of from 12 percent to about 30 percent based on the weights of the respective polyols, in the presence of an amine catalyst system. The resulting polyurethane foams are eminently suitable for seating cushions used in tropical or subtropical environments, may be prepared by a cold molding process, and may be used without an elevated temperature post cure.
Type:
Grant
Filed:
May 30, 1996
Date of Patent:
February 17, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Mark R. Kinkelaar, Keith Douglas Cavender, James L. Lambach, Robert D. Brasington, Frank E. Critchfield
Abstract: Improved double metal cyanide (DMC) catalysts useful for making epoxide polymers are disclosed. One catalyst is a paste of a double metal cyanide (DMC) compound, an organic complexing agent, and water. The paste comprises at least about 90 wt. % of particles having a particle size within the range of about 0.1 to about 10 microns as measured by light scattering in polyether polyol dispersions of the catalyst particles. Preferred catalysts have a bimodal particle size distribution. The paste catalyst is more active and simpler to prepare than powder DMC catalysts. Polyols made from the paste catalyst have low unsaturations, low viscosities, and narrow molecular weight distributions, and are useful in making a variety of polyurethane products.
Type:
Grant
Filed:
February 21, 1997
Date of Patent:
February 3, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Paul T. Bowman, Harry R. Hinney, Robert L. Meeker
Abstract: Double metal cyanide (DMC) catalysts useful for epoxide polymerizations are disclosed. The catalysts comprise a DMC compound, an organic complexing agent, and from about 2 to about 80 wt. % of a functionalized polymer or a water-soluble salt derived from the polymer. The catalysts are easy to prepare and isolate, are substantially non-crystalline, and have high activity for polymerizing epoxides. Polyols made from the catalysts have exceptionally low unsaturations, low viscosities, and reduced levels of high molecular weight polyol tail.
Abstract: Improved double metal cyanide catalysts are disclosed. The substantially amorphous catalysts of the invention are more active for polymerizing epoxides than conventional DMC catalysts, which have a substantial crystalline component. Polyol products made with the catalysts are unusually clear, have exceptionally low unsaturations, and contain no detectable amount of low molecular weight polyol impurities. Methods of making the improved DMC catalysts are also disclosed. In one method, the reactants are intimately combined to produce a catalyst of the invention. In another method, an organic complexing agent is initially present in the reactant solutions.
Type:
Grant
Filed:
May 15, 1995
Date of Patent:
January 27, 1998
Assignee:
Arco Chemical Technology, L.P.
Inventors:
Bi Le-Khac, Paul T. Bowman, Harry R. Hinney
Abstract: Graffiti removers particularly useful for removing permanent ink from painted surfaces are disclosed. The graffiti removers include a dye solvent (a pyrrolidone or a lactone), a dye non-solvent (a glycol ether ester or a glycol diether), and a dye bleaching agent (an oxidizing agent, reducing agent, or base). The dye bleaching agent is the key to eliminating the problem of "ghosting" that is observed when conventional graffiti removers are used to remove permanent marker ink graffiti.