Patents by Inventor Edward E. McEntire
Edward E. McEntire has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4342687Abstract: A primary amine may be reacted with formaldehyde and a 1,2-diol to produce N-substituted perhydrodioxazepines of the formula: ##STR1## where R is alkyl, alkoxyalkyl, aminoalkyl or aryl alkyl and R' is hydrogen or lower alkyl. These compounds may be easily prepared and have a low odor which is essential in their utility as polyurethane catalysts. By varying the R group, the catalytic characteristics of the compounds may be altered as desired.Type: GrantFiled: September 8, 1981Date of Patent: August 3, 1982Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Edward E. McEntire
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Patent number: 4310634Abstract: Polyisocyanurate catalysts are disclosed which have the formula: ##STR1## where R.sub.1 and R.sub.2 are independently selected from alkyl groups of less than about 3 carbon atoms or where R.sub.1 and R.sub.2 together comprise cycloalkyl or morpholino groups and where R.sub.3 is hydrogen or alkyl groups containing less than about 3 carbon atoms. Said catalysts are useful in promoting the reaction between a polyol and an aromatic polyisocyanate to prepare a polymer containing recurring isocyanurate and urethane linkages.Type: GrantFiled: December 15, 1980Date of Patent: January 12, 1982Assignee: Texaco Development Corp.Inventors: Edward E. McEntire, Robert L. Zimmerman
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Patent number: 4287363Abstract: A catalytic process for the preparation of N-(alkylaminoalkyl)acrylamides is disclosed which comprises subjecting a corresponding .beta.-aminopropionamide to a temperature of about 100.degree.-250.degree. C. in presence of a catalyst comprising a magnesium, calcium or aluminum salt of a strong acid, and separating the N-(alkylaminoalkyl)acrylamide from the reaction product. The corresponding .beta.-aminopropionamide compounds can be prepared by mixing and reacting at least 2 moles of an alkylaminoalkyl amine with an acrylic acid or ester compound. The inventive process provides the production of the N-(alkylaminoalkyl)acrylamides in high yields with minimal back-addition or polymerization.Type: GrantFiled: September 2, 1980Date of Patent: September 1, 1981Assignee: Texaco Inc.Inventor: Edward E. McEntire
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Patent number: 4286072Abstract: Polyisocyanurate catalysts are disclosed which have the formula: ##STR1## where R.sub.1 and R.sub.2 are independently selected from alkyl groups of less than about 3 carbon atoms or where R.sub.1 and R.sub.2 together comprise cycloalkyl or morpholino groups and where R.sub.3 is hydrogen or alkyl groups containing less than about 3 carbon atoms. Said catalysts are useful in promoting the reaction between a polyol and an aromatic polyisocyanate to prepare a polymer containing recurring isocyanurate and urethane linkages.Type: GrantFiled: July 21, 1980Date of Patent: August 25, 1981Assignee: Texaco Development Corp.Inventors: Edward E. McEntire, Robert L. Zimmerman
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Patent number: 4265821Abstract: Alkyl substituted ethylene carbonates are converted to substituted ethylene oxides by heating the respective carbonates in the presence of a catalyst comprising alkali metal halides or lanthanum iodide. The alkyl substituted ethylene carbonates have the general formula ##STR1## where R is alkyl, aryl, substituted alkyl, substituted aryl, alkaryl or aralkyl.Type: GrantFiled: November 7, 1979Date of Patent: May 5, 1981Assignee: Texaco Dev. Corp.Inventors: Edward E. McEntire, Robert M. Gipson
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Patent number: 4259259Abstract: Covers a process for the preparation of a .beta.-aminopropionanide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrolidine and piperidine ring groups; which process comprises reacting in the presence of an alkali or alkaline earth metal salt of a strong acid having a pK.sub.a of less than about 2.0 acting as a catalyst a tertiaryaminoalkyl amine of the formula: where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR2## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.Type: GrantFiled: November 15, 1979Date of Patent: March 31, 1981Assignee: Texaco Development Corp.Inventor: Edward E. McEntire
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Patent number: 4256666Abstract: Covers a process for the preparation of a .beta.-aminopropionamide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrolidine and piperidine ring groups; which process comprises reacting in the presence of a Lanthanide salt having an anion derivative from a strong acid having a pK.sub.a of about 5 or less acting as a catalyst, a tertiaryaminoalkyl amine of the formula: ##STR2## where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR3## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.Type: GrantFiled: October 29, 1979Date of Patent: March 17, 1981Assignee: Texaco Development CorporationInventor: Edward E. McEntire
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Patent number: 4256665Abstract: Covers a process for the preparation of a .beta.-aminopropionamide of the formula ##STR1## wherein R.sub.1 is H or methyl, n is an integer of 2 to 6 and R.sub.2 and R.sub.3, taken singly are hydrogen or lower alkyl groups containing 1 to 4 carbon atoms or R.sub.2 and R.sub.3, taken jointly are combined with the nitrogen atom to form a heterocyclic group selected from the groups consisting of morpholine, pyrrollidine and piperidine ring groups; which process comprises reacting in the presence of carbon dioxide acting as a catalyst a tertiaryaminoalkyl amine of the formula. ##STR2## where R.sub.2, R.sub.3 and n are as above with an acrylic or methacrylic compound of the formula: ##STR3## where R.sub.1 is as above and R.sub.4 is lower alkyl and recovering said .beta.-aminopropionamide.Type: GrantFiled: August 31, 1979Date of Patent: March 17, 1981Assignee: Texaco Development CorporationInventor: Edward E. McEntire
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Patent number: 4251637Abstract: The use of tertiary amino substituted oxazolidines as polyisocyanurate catalysts is disclosed. Said catalysts are useful in promoting the reaction between a polyol and an aromatic polyisocyanate to prepare a polymer containing recurring isocyanurate and urethane linkages.Type: GrantFiled: September 13, 1979Date of Patent: February 17, 1981Assignee: Texaco Development CorporationInventors: Edward E. McEntire, Robert L. Zimmerman, Howard P. Klein
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Patent number: 4239916Abstract: New catalysts for isocyanurate foams are those comprising aminomethacrylate salts. The foams are obtained by the polymerization of an aromatic polyisocyanate, and a polyether or polyester polyol in the presence of a blowing agent and said amino methacrylate salts falling within the following structural formula: ##STR1## where the radicals represented by R are hydroxy lower alkyl, and M is selected from the group consisting of sodium, potassium, cesium, lithium and rubidium. The novel foams are useful in preparing rigid, flexible, semi-rigid, or semi-flexible materials such as panels, slabs or sprayed foam surfaces.Type: GrantFiled: October 30, 1978Date of Patent: December 16, 1980Assignee: Texaco Development Corp.Inventors: Robert L. Zimmerman, Edward E. McEntire, Howard P. Klein
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Patent number: 4175097Abstract: Covers compounds of the formula: ##STR1## where R is lower alkyl and R.sub.1 is hydrogen, alkyl or aryl and ##STR2## where R is lower alkyl and R.sub.2 is hydrogen or alkyl. Also covers a method of producing a polyurethane by utilizing said above compounds as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst.Type: GrantFiled: October 21, 1977Date of Patent: November 20, 1979Assignee: Texaco Development Corp.Inventor: Edward E. McEntire
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Patent number: 4143071Abstract: Covers compounds of the formula ##STR1## where R" is lower alkyl, R is hydrogen or lower alkyl and Y is selected from the group consisting of CN, CONH.sub.2, CO.sub.2 R', CONR'.sub.2 and COR' where R' independently is hydrogen, lower alkyl or aryl. Also covers a method of producing a polyurethane by utilizing said above compounds as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst.Type: GrantFiled: September 6, 1977Date of Patent: March 6, 1979Assignee: Texaco Development Corp.Inventors: Edward E. McEntire, George P. Speranza
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Patent number: 4107096Abstract: Low foaming beta-amino propionic acid surface active agents are described having the following formula: ##STR1## where R is a C.sub.6 to C.sub.18 aliphatic hydrocarbon radical and n has an average value of from 0 to about 13.The compounds of this invention produce only weak foams as compared with prior art beta-amino acids and have improved solubility and wetting properties over the entire pH range as compared to such prior art beta-amino acids. The compounds of this invention are particularly desirable for use either alone or in combination with other surface active agents and detergents in many washing and wetting applications where foaming is an undesirable characteristic. The compounds are also useful as emulsification agents.Type: GrantFiled: October 11, 1977Date of Patent: August 15, 1978Assignee: Texaco Development Corp.Inventors: Edward E. McEntire, Robert M. Gipson
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Patent number: 4101470Abstract: Covers compound of the formula: ##STR1## where R is lower alkyl, R.sub.1 is selected from the group consisting of hydrogen, alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, aralkyl, and substituted aralkyl. Also covers a method of producing a polyurethane by utilizing said above compounds as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst.Type: GrantFiled: November 11, 1976Date of Patent: July 18, 1978Assignee: Texaco Development Corp.Inventor: Edward E. McEntire
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Patent number: 4101466Abstract: Covers compounds of the formula: ##STR1## where R is lower alkyl and R.sub.1 is hydrogen, alkyl or aryl and ##STR2## where R is lower alkyl and R.sub.2 is hydrogen or alkyl. Also covers a method of producing a polyurethane by utilizing said above compounds as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst.Type: GrantFiled: December 1, 1976Date of Patent: July 18, 1978Assignee: Texaco Development Corp.Inventor: Edward E. McEntire
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Patent number: 4099004Abstract: New catalysts for isocyanurate foams are those comprising aminomethacrylate salts. The foams are obtained by the polymerization of an aromatic polyisocyanate, and a polyether or polyester polyol in the presence of a blowing agent and said amino methacrylate salts falling within the following structural formula: ##STR1## where the radicals represented by R when taken singly are lower alkyl, and hydroxy lower alkyl, and when taken together with the adjacent nitrogen atom are selected from the group consisting of morpholino, C-substituted morpholino, N-alkylpiperazino and C-substituted N-alkylpiperazino, and M is selected from the group consisting of sodium, potassium, cesium, lithium and rubidium. The novel foams are useful in preparing rigid, flexible, semi-rigid, or semi-flexible materials such as panels, slabs or sprayed foam surfaces.Type: GrantFiled: December 3, 1976Date of Patent: July 4, 1978Assignee: Texaco Development CorporationInventors: Robert L. Zimmerman, Edward E. McEntire, Howard P. Klein
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Patent number: 4094827Abstract: Covers a method of producing a polyurethane by utilizing compounds of the structure below as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst: ##STR1## where R is lower alkyl and X is hydrogen or CONR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, alkyl and aryl with the proviso that both R.sub.1 and R.sub.2 may not be aryl.Type: GrantFiled: October 18, 1976Date of Patent: June 13, 1978Assignee: Texaco Development CorporationInventor: Edward E. McEntire
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Patent number: 4049591Abstract: Covers compounds of the formula ##STR1## where R" is lower alkyl, R is hydrogen or lower alkyl and Y is selected from the group consisting of CN, CONH.sub.2, CO.sub.2 R', CONR'.sub.2 and COR' where R' independently is hydrogen, lower alkyl or aryl. Also covers a method of producing a polyurethane by utilizing said above compounds as catalysts in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst.Type: GrantFiled: October 18, 1976Date of Patent: September 20, 1977Assignee: Texaco Development CorporationInventors: Edward E. McEntire, George P. Speranza
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Patent number: 4026836Abstract: New catalysts for isocyanurate foams are those comprising aminomethacrylate salts. The foams are obtained by the polymerization of an aromatic polyisocyanate, and a polyether or polyester polyol in the presence of a blowing agent and said amino methacrylate salts falling within the following structural formula: ##STR1## where the radicals represented by R when taken singly are lower alkyl, and hydroxy lower alkyl, and when taken together with the adjacent nitrogen atom are selected from the group consisting of morpholino, C-substituted morpholino, N-alkylpiperazino and C-substituted N-alkylpiperazino, and M is selected from the group consisting of sodium, potassium, cesium, lithium and rubidium. The novel foams are useful in preparing rigid, flexible, semi-rigid, or semi-flexible materials such as panels, slabs or sprayed foam surfaces.Type: GrantFiled: December 29, 1975Date of Patent: May 31, 1977Assignee: Texaco Development CorporationInventors: Robert L. Zimmerman, Edward E. McEntire, Howard P. Klein