Material Contains A Group Iia Metal Atom (be, Mg, Ca, Sr, Ba, Ra) Patents (Class 528/140)
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Patent number: 4448951Abstract: Modified benzyl ether-containing resole polyols derived from phenol, paraformaldehyde and an aliphatic hydroxyl compound are prepared using a metal derivative as a catalyst. These polyols react with organic polyisocyanates to yield closed cell, low friability, low combustibility, rigid polyurethane foams without the need for post curing at elevated temperature. They are also useful in the preparation of modified rigid polyisocyanurate foams.Type: GrantFiled: January 17, 1983Date of Patent: May 15, 1984Assignee: BASF Wyandotte CorporationInventors: John P. Rupert, John T. Patton, Jr.
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Patent number: 4433119Abstract: There are described liquid compositions of a hemiformal of phenol and/or a hemiformal of a methylolated phenol with a miscible polymers such as phenol-formaldehyde resoles, phenol-formaldehyde, novolacs, aromatic polyesters, unsaturated polyesters, poly(aryl-ethers), aromatic polycarbonates urea-formaldehyde resins, or melamine-formaldehyde resins. The compositions are useful for forming thermoset plastic materials.Type: GrantFiled: January 19, 1982Date of Patent: February 21, 1984Assignee: Union Carbide CorporationInventors: George L. Brode, Sui-Wu Chow
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Patent number: 4403076Abstract: A fast curing shell molding composition having the tensile strength of a conventional novolac resin when cured contains a fast curing novolac resin comprising a methylene chained polyphenylol wherein a major portion of the methylene linkages are coupled to adjacent phenylol groups at the o-o' and p-p' position, wherein at least about 19% of the methylene linkages are coupled to adjacent phenylol groups at the o-o' portions, and wherein at least about 3% of the total number of methylene linkages are coupled to adjacent phenylol groups at the p-p' positions. The shell molding composition is produced from the fast curing novolac resin by uniformly coating refractory granules with the fast curing resin. The fast curing novolac resin can be prepared by blending a conventional novolac resin with a novolac resin having a large proportion of methylene linkages coupled to adjacent phenylol groups at the o-o' position.Type: GrantFiled: March 5, 1982Date of Patent: September 6, 1983Assignee: Pacific Resins & Chemicals, Inc.Inventor: Roderick A. McDonald
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Patent number: 4393189Abstract: A method of preparing a thermoplastic, water-soluble, phenolic aldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the aldehyde are reacted to less than 100 percent completion in an amount so that the aldehyde to phenolic compound ratio is in the range of about 0.6 to about 1.5 and at an acidic pH and for a period of time equivalent to about 3 hours to about 10 hours when the temperature is in the range of about 55.degree. F. (13.degree. C.) to about 90.degree. F. (32.degree. C.) to produce a resinous mixture. In the second stage the pH of the reaction is adjusted within the range above about 7.0 to about 7.Type: GrantFiled: November 16, 1981Date of Patent: July 12, 1983Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
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Patent number: 4376854Abstract: A process for preparing a resorcinol copolymer, comprising at least one specific phenol with formaldehyde at a certain mole ratio to obtain a resol-type precondensate containing 1 to 30% of residual unreacted formaldehyde and then adding said resol-type precondensate to a mixture of an acid catalyst and at least one resorcinol to effect co-condensation. The obtained copolymer is useful for an adhesive for polyester fiber and rubber.Type: GrantFiled: April 5, 1982Date of Patent: March 15, 1983Assignee: Hodogaya Chemical Co., Ltd.Inventors: Toyohiko Yamaguchi, Koichi Kashima, Nobuo Kaifu
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Patent number: 4366303Abstract: Particulate resoles are produced by mixing phenol, formaldehyde and amine in an aqueous medium containing a protective colloid. The resoles exhibit improved cure rate and sinter resistance when an alkaline compound is added to the reaction mixture after particulate formation.Type: GrantFiled: December 11, 1981Date of Patent: December 28, 1982Assignee: Union Carbide CorporationInventor: Peter W. Kopf
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Patent number: 4350800Abstract: A process for the preparation of synthetic resins based on resorcinol compounds which comprises reacting a resorcinol pitch which is obtained in the manufacture of resorcinol from benzenedisulfonic acid in at least one step with an oxo-compound selected from aldehydes, ketones and compounds based on or splitting off at least one of these substances, and the use of the products as binders for abrasive articles.Type: GrantFiled: September 14, 1981Date of Patent: September 21, 1982Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Franz Landauer, Klaus Schmiedel
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Patent number: 4343924Abstract: Disclosed is an improved method for coating a substrate with a film of a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary-amine catalyst. The pot life of the coating composition is substantially increased without deleterious loss of properties of the ultimately cured film wherein the coating composition comprises three components. The first component is a phenol-functional condensation product of (a) a phenol-aldehyde reaction product bearing a plurality of methylol and phenol groups, and (b) a polyol, polycarboxylic acid, or polyepoxide, wherein the condensation product is reacted with a selective transmethylolating agent for substantially transforming residual methylol groups into non-active hydrogen groups. The second component is a multi-isocyanate cross-linking agent and the third component is an organic solvent. The coating composition is applied to a substrate and cured by exposure of the coated substrate to a vaporous tertiary amine catalyst.Type: GrantFiled: September 14, 1981Date of Patent: August 10, 1982Assignee: Ashland Oil, Inc.Inventor: Gary L. Linden
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Patent number: 4318840Abstract: Binders for foundry core sand and other binder applications are produced from the tars resulting from production of bisphenol A.Type: GrantFiled: December 17, 1980Date of Patent: March 9, 1982Assignee: The Quaker Oats CompanyInventors: James E. Doyle, Russell B. Lembke
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Patent number: 4317901Abstract: A method for the production of a powdery, free-flowing phenol/formaldehyde resin is disclosed wherein a polyvalent cationic precipitant is added to the resin emulsion produced, the precipitate is filtered, washed with water and dried.Type: GrantFiled: October 6, 1980Date of Patent: March 2, 1982Assignee: Formica CorporationInventor: Harry F. Cosway
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Patent number: 4314050Abstract: A method of preparing a thermoplastic, long-chain water-soluble, phenolic formaldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the formaldehyde are reacted to less than 100 percent completion in an amount so that the formaldehyde to resorcinol ratio is in the range of about 0.6 to about 2.0 and at an acidic pH and for a period of time equivalent to about 1 hour to about 20 hours when the temperature is in the range of about 30.degree. F.(-31 1.1.degree. C.) to about 122.degree. F. (50.degree. C.) to produce a resinous mixture having a predominant amount of trimer polymer along with minor amounts of dimer and higher oligomer polymers and along with unreacted phenolic compound and aldehyde. In the second stage the pH of the reaction is adjusted within the range above of about 7.0 to about 7.Type: GrantFiled: October 30, 1978Date of Patent: February 2, 1982Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
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Patent number: 4311619Abstract: A phenol-aldehyde resin useful in such applications as a cold-set binder for cores and molds used in the foundry industry and reactive prepolymers used in reaction injection molding compositions produced by the steps of reacting a phenol and aldehyde in a mole ratio of 1 to 1-2.3 in the presence of catalytic amounts of an organic compound of aluminum, zirconium or titanium.Type: GrantFiled: April 14, 1980Date of Patent: January 19, 1982Assignee: Aristo CorporationInventors: Charles E. Seeney, John F. Kraemer, Larry J. Hoffman
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Patent number: 4299947Abstract: A high-ortho phenolic novolac resin having excellent curability, heat stability and flowability can be produced safely at low cost by a process which comprises reacting a phenol and an aldehyde at a temperature of more than 100.degree. C. with (A) a catalyst effective for the addition reaction selected from the salts of divalent metals in combination with (B) a catalyst effective for the condensation reaction, or comprises reacting a phenol and an aldehyde under reflux in the presence of the catalyst (A), adding an acid to adjust the pH to 1-5, removing water under reduced pressure and then subjecting the product to reaction at a temperature of more than 100.degree. C. This process enables the addition reaction and the condensation reaction to proceed with a good balance, can solve problems arising in the prior process such as gelation, low yield and the like, and can produce a high-ortho type phenolic novolac resin safely at low cost. Accordingly, this process is quite advantageous in industry.Type: GrantFiled: June 11, 1980Date of Patent: November 10, 1981Assignee: Sumitomo Bakelite Company LimitedInventors: Motoyuki Nanjo, Tsutomu Watanabe, Shigeru Koshibe, Keiji Azuma
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Patent number: 4277596Abstract: There is provided a molded shaped structure made by molding the reaction product of an organic resin and a modified magnesium silicate obtained by calcining chrysotile asbestos tailings. The new product is characterized by the absence of any fibers.Type: GrantFiled: April 8, 1980Date of Patent: July 7, 1981Assignee: Societe Nationale de l'AmianteInventor: Jean M. Lalancette
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Patent number: 4269949Abstract: A finished resin comprising a highly condensed phenol formaldehyde resole resin which has green groups formed by a low condensation phenol formaldehyde resin, the finished resin being modified by addition of a weak acid and a non-cellulosic protective colloid to improve reactivity and flow properties thereof.Type: GrantFiled: June 27, 1979Date of Patent: May 26, 1981Assignee: Borden, Inc.Inventors: Charles H. Hickson, Pitchaiya Chandramouli
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Patent number: 4268657Abstract: Improved friction elements suited for use for example in an automotive or similar brake or in a clutch are provided by employing therein as a binder the reaction product of phenol, formaldehyde, and monoalkylphenol having from 4 to about 20 carbon atoms in the alkyl group. The mole ratio range of phenol:alkylphenol:formaldehyde is about 2:1-5:1-7 and the number of moles of phenol and alkylphenol combined exceeds the number of moles of formaldehyde. An improved method of making friction elements is also provided which uses such binder.Type: GrantFiled: December 10, 1979Date of Patent: May 19, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Anthony P. Manzara
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Patent number: 4264671Abstract: Low-color or white, dilutable condensation products of formaldehyde and phenol in molar ratios of 1.9-5.0:1, characterized by carbon-13 nuclear magnetic resonance spectra as having at least about 30 molar percent of the total formaldehyde content of the resin bound to phenol nuclei in benzyl formal groups of the form Ph--(CH.sub.2 O).sub.n --CH.sub.2 OH wherein n.gtoreq.1, and less than about 40 molar percent of the total formaldehyde content of the resin bound to phenol nuclei in methylol groups of the form Ph--CH.sub.2 OH, wherein Ph is a phenol nucleus. Phenol, water and an alkaline catalyst, limited to 0.5-2.2 moles of catalyst per 100 moles of phenol and preferably lithium carbonate, are mixed with formaldehyde at 1.9-5.0 formaldehyde to phenol ratios. The reaction mixture is heated at a uniform rate over 1 hour to reflux temperature and refluxed until a viscosity of 400-500 centipoise at 50-75% solids is attained. The mixture is cooled to 50.degree. C.Type: GrantFiled: August 2, 1978Date of Patent: April 28, 1981Assignee: Weyerhaeuser CompanyInventors: M. Frank Gillern, Katashi Oita, Robert J. Teng, George T. Tiedeman
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Patent number: 4255554Abstract: Phenol-formaldehyde-furfuryl alcohol terpolymers containing substantially equimolar proportions of phenol and furfuryl alcohol are prepared by reacting phenol, formaldehyde and furfuryl alcohol under essentially anhydrous conditions in the presence of a metallic catalyst with continuous removal of the water of condensation from the reaction mixture.Type: GrantFiled: October 15, 1979Date of Patent: March 10, 1981Assignee: The Quaker Oats CompanyInventor: Joseph P. Wuskell
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Patent number: 4216295Abstract: This invention relates to an improved foamable resole resin composition comprising a resole resin, a blowing agent and a surfactant wherein said improvement comprises incorporating a particular resole resin catalyzed with alkaline earth metal hydroxides and neutralized with oxalic acid or its acid salts providing inert insoluble oxalate salts dispersed in said resole. Said salts are sized controlled and stabilized in an aqueous resole resin solution having about 60 to 99% resole resin by weight. Methods for preparing and foaming said compositions are disclosed.Type: GrantFiled: December 20, 1976Date of Patent: August 5, 1980Assignee: Monsanto CompanyInventor: Ronald H. Dahms
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Patent number: 4182732Abstract: A coating and adhesive composition that may be in finely divided powder form is provided comprising a solid phenolic resole (one-step) resin having a gel time of between 150 seconds to about 250 seconds at 150.degree. C., said resin being the reaction product of bisphenol-A and formaldehyde at a mole ratio between about 2.11 to 2.64 moles of formaldehyde per mole of bisphenol-A in the presence of a catalytic quantity of a condensation catalyst at a temperature of at least about 70.degree. C. that is acidified to a pH from about 3 up to 7 and dehydrated.Type: GrantFiled: September 28, 1977Date of Patent: January 8, 1980Assignee: Union Carbide CorporationInventor: John S. Fry
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Patent number: 4176106Abstract: The present invention provides particular phenol/formaldehyde resoles which are especially useful as foamable resins, and further provides cellular phenolic products having physical properties which are especially attractive for end-use application as construction foam. The resoles are characterized by a particular relationship between their viscosity and water content, expressed as the area bounded by certain points on a plot of resole viscosity on a logarithmic scale, as a function of water content of the resole, the particular area depending upon the mole ratio of formaldehyde-to-phenol at which the resole has been condensed. It has been found that phenol-formaldehyde resoles having the defined viscosity/water relationship are capable of providing phenolic foam having acceptable foam processability, a foam density from about 1.90 to about 3.Type: GrantFiled: July 28, 1977Date of Patent: November 27, 1979Assignee: Union Carbide CorporationInventors: Wallace G. Reid, Rakesh Saini, Kenneth E. Atkins
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Patent number: 4170697Abstract: Silicon halides will react chemically with polyols to produce polyol silicate resinous products which will react chemically with polyisocyanates to produce polyisocyanate silicate solid or cellular solid products.Type: GrantFiled: June 23, 1978Date of Patent: October 9, 1979Inventor: David H. Blount
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Patent number: 4157324Abstract: This invention relates to high ortho etherified resole resins. The resole resins are prepared by reacting under acidic conditions phenol with formaldehyde in the presence of a divalent electropositive metal. The resole resins are then etherified with an alcohol and dehydrated to less than 1 percent water. The novel high ortho etherified resole resins are useful in coating, bonding and adhesive compositions. Such resoles are readily curable with coreactive resins providing chemical and solvent resistance.Type: GrantFiled: June 29, 1978Date of Patent: June 5, 1979Assignee: Monsanto CompanyInventor: Harry M. Culbertson
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Patent number: 4140845Abstract: Water-immiscible thermosetting phenol-formaldehyde resins in which a large proportion of the linkages between the benzene rings are benzyl ether linkages located ortho to the phenolic hydroxyl groups are produced by reaction of at least 1 mole of formaldehyde with 1 mole of phenol in an aqueous reaction medium in the presence of a metal carboxylate catalyst, such as, zinc acetate, in two stages, in which, in the first stage exothermic addition of formaldehyde to phenol occurs and, in the second stage, methylol phenol is polymerized to form the resin. Methods for control of the rate of polymerization, methods of separation of product resin from aqueous phase, methods of molecular weight distribution control, a semi-continuous operation and an alternative polymerization procedure are described.Type: GrantFiled: March 21, 1977Date of Patent: February 20, 1979Assignee: Cor Tech Research Ltd.Inventor: Ramesh C. Vasishth
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Patent number: 4130550Abstract: A phenol-formaldehyde composition useful as a raw material for the preparation of phenolic resins, which comprises one or more phenols and not more than about 6 moles of formaldehyde per 1 mole of said one or more phenols, and, as optional components, not more than about 7 moles of water and not more than about 7 moles of methanol per 1 mole of said one or more phenols, the composition being obtained by dissolving formaldehyde into the one or more phenols, optionally with water or water plus methanol.Type: GrantFiled: March 2, 1978Date of Patent: December 19, 1978Assignee: Matsushita Electric Works, Ltd.Inventors: Yoshihiro Kitsuda, Takahisa Kouyama
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Patent number: 4123414Abstract: Method of manufacturing molded articles of liquid phenol resins or resols, obtained by simultaneously projecting onto a mold surface at least one resin of the aforesaid type, glass reinforcing elements and at least one acid catalyst, as main component elements, this method being characterized in that at least one anhydrous and hydrophilous inorganic compound is projected simultaneously with said main component elements in an amount corresponding to 8% to 12% of the weight of liquid phenol resin.Type: GrantFiled: November 11, 1976Date of Patent: October 31, 1978Assignee: Societe Chimique des CharbonnagesInventor: Henri Milette
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Patent number: 4120847Abstract: This invention relates to high ortho etherified resole resins. The resole resins are prepared by reacting under acidic conditions phenol with formaldehyde in the presence of a divalent electropositive metal. The resole resins are then etherified with an alcohol and dehydrated to less than 1 percent water. The novel high ortho etherified resole resins are useful in coating, bonding and adhesive compositions. Such resoles are readily curable with coreactive resins providing chemical and solvent resistance.Type: GrantFiled: September 6, 1977Date of Patent: October 17, 1978Assignee: Monsanto CompanyInventor: Harry M. Culbertson
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Patent number: 4119611Abstract: A two-stage process for making a linear condensate of phenol and formaldehyde which can be extruded as a film or thread. In the first stage phenol and formaldehyde are reacted at about 90.degree. C to produce a clear low-viscosity phenol-methylol liquid, the pH of which is adjusted to a value greater than 3, say between 3.5 and 7. In the second stage the product of the first stage is added in aliquot portions to molten phenol having a pH of 3 or less, while maintaining the temperature at about 100.degree. C. After all the phenol-methylol has been added the mixture is slowly heated as the viscosity increases up to about 150.degree. C until there is no further increase in viscosity. The highly viscous end product can be extruded as a film or thread.Type: GrantFiled: October 27, 1977Date of Patent: October 10, 1978Assignee: Zimmer AktiengesellschaftInventor: Joachim Lobering
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Patent number: 4116921Abstract: There is described a new "one-step" bis A-formaldehyde resin, and a molding material containing the resin with which one may achieve molded products possessing excellent properties and almost optimum molding characteristics such as excellent molding latitude, low degree of mold shrinkage, high modulus at elevated temperature, a low degree of deformation at elevated temperatures, and excellent steam crack resistance and electrical properties. The molding material comprises a light colored bis-A formaldehyde resin and reinforcing filler for the resin. The resin is a heat convertible resin (resole) which comprises the product of the reaction of formaldehyde and bis A in the mole ratio of about 2 to about 3.75, in the presence of a catalytic amount of an alkali metal hydroxide or barium hydroxide condensation catalyst. The molding material of this invention is particularly desirable in making molded products by the injection molding or transfer molding processes.Type: GrantFiled: January 5, 1977Date of Patent: September 26, 1978Assignee: Union Carbide CorporationInventors: Anthony Robert Olivo, Anthony Constantine Soldatos, Sidney Joseph Schultz
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Patent number: 4113700Abstract: The invention relates to an improved process for preparing high ortho novolac resins, said process including reacting phenol and formaldehyde in the presence of a divalent electropositive metal oxide, hydroxide or organic salt wherein the improvement comprises conducting said reaction with said catalysts in combination with a divalent electropositive metal salt selected from the group consisting of sulfonates and fluoroborates or acids selected from the group consisting of sulfonic and fluoroboric or mixtures thereof.Type: GrantFiled: January 10, 1977Date of Patent: September 12, 1978Assignee: Monsanto CompanyInventor: Harry M. Culbertson
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Patent number: 4098770Abstract: A method of preparing a modified phenol-formaldehyde resin in solid particulate form comprising reacting together, in an aqueous medium, phenol and formaldehyde, in a ratio of 1.0 mole phenol to between 1.8 and 3.5 moles of formaldehyde, in the presence of between 0.1 and 1.0 moles of a basic catalyst; continuing this reaction until a desired viscosity is reached; modifying the reaction system by adding thereto between 0 and 30%, based on the weight of phenol originally taken of a non-phenolic polyhydroxy compound; spray drying the thus modified liquid resin in a pressure nozzle drier, and chilling the spray dried particulate solid. These solid resins are redispersible in water and stable on storage, compared to the known aqueous, equivalent, systems.Type: GrantFiled: September 15, 1976Date of Patent: July 4, 1978Assignee: Reichhold Chemicals LimitedInventors: Antoine Berchem, Krishan Kumar Sudan, Edward Michael Gres
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Patent number: RE30375Abstract: This specification discloses ecologically desirable, improved binder compositions suitable for bonding fibers. These binders exhibit low pollutant characteristics and improved properties, due to a combination into the binder of aminoplast resins or non phenolic monomeric materials capable of co-condensing with formaldehyde, together with a substantially phenol free, low mono methylolphenol high .[.ortho para di.]. .Iadd.2,4,6-tri .Iaddend.methylol .[.phenol.]. .Iadd.phenols .Iaddend.content, water soluble thermosetting phenol formaldehyde resole solution. The phenolic resole resin is made to conform to the desired composition by mixing together a high mole ratio of formaldehyde with phenol and calcium hydroxide with cooling so that very little reaction takes place.Type: GrantFiled: January 12, 1978Date of Patent: August 19, 1980Assignee: Fiberglas Canada Ltd.Inventors: Hendrik H. J. Deuzeman, Norman Lumley, Ruben A. Santos