Patents by Inventor Thomas A. Hardy

Thomas A. Hardy 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).

  • Patent number: 5117033
    Abstract: There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting with the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: May 26, 1992
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 5097057
    Abstract: There are disclosed novel phosphorus-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphonate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: March 17, 1992
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4886895
    Abstract: There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: December 12, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4883892
    Abstract: There are disclosed novel phosphorous-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphonate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.
    Type: Grant
    Filed: October 20, 1988
    Date of Patent: November 28, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4883891
    Abstract: There are disclosed novel phosphorous-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: November 28, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4820854
    Abstract: There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: April 11, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4808744
    Abstract: There are disclosed novel phosphorus-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphonate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: February 28, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4697030
    Abstract: There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.
    Type: Grant
    Filed: May 23, 1985
    Date of Patent: September 29, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4458035
    Abstract: Flame retardant oligomeric phosphate ester compositions having the structural formula: ##STR1## are prepared, wherein R is C.sub.1 -C.sub.10 alkyl or haloalkyl, R.sup.1 and R.sup.2 can be the same or different and are hydrogen, C.sub.1 -C.sub.10 alkyl or haloalkyl and n is an integer from zero to about 10.The method of preparing the compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris(haloalkyl)phosphate in the presence of about 0.01% to about 5% of a phosphite at a temperature from about 0.degree.-200.degree. C. A polyphosphate ester having P--O--P bonds is formed which is then reacted with an epoxide to yield the oligomeric phosphate ester flame retardant compositions.Alternatively, a method of preparing similar compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris (haloalkyl)phosphite at a temperature from about 0.degree. C. to about 200.degree. C.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: July 3, 1984
    Assignee: Stauffer Chemical Company
    Inventors: Thomas A. Hardy, Fred Jaffe
  • Patent number: 4407765
    Abstract: A process for the preparation of organic phosphate-phosphonates comprises the steps of reacting an organic acylating agent with an organophosphite triester to form an intermediate followed by reacting the intermediate with an organophosphite diester.Typically benzoyl chloride is the acylating agent, triethyl phosphite and bis (.beta.-chloroethyl) phosphite the sequential reactants, and the second step is carried out in the presence of a catalytic amount of a tertiary amine. A solvent such as methylene dichloride may be employed.Organic phosphate-phosphonates are useful as flame retardants, especially in urethane foams.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: October 4, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Thomas A. Hardy
  • Patent number: 4394330
    Abstract: Flame retardant phosphonate derivatives of polyalkylene polyamines are prepared having the structural formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.5 can be the same or different substituted or nonsubstituted lower alkylene groups of about 2-10 carbons, or aryl groups of about 6-14 carbons; and R.sup.5 can also be haloalkyl of about 1-10 carbons;R.sup.3 can be a lower alkylene radical of about 1-10 carbons;R.sup.4 can be an alkyl, alkenyl, alkynyl, or aryl group of about 1-20 carbons;m is a number from 0 to 2;n is a number from 0 to 2;y is a number from 0 to 10; andx can be the same as the (R.sup.5 OH) group or the ##STR2## The preparation involves the condensation of a polyalkylene-polyamine with an aldehyde or ketone and a phosphonate or a phosphite. The condensation product is then reacted with an epoxide to yield the phosphonate derivatives of polyalkylene-polyamines.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: July 19, 1983
    Assignee: Stauffer Chemical Company
    Inventors: Thomas A. Hardy, Sophia Y. Liu
  • Patent number: 4382042
    Abstract: Flame retardant oligomeric phosphate ester compositions having the structural formula: ##STR1## are prepared, wherein R is C.sub.1 -C.sub.10 alkyl or haloalkyl, R.sup.1 and R.sup.2 can be the same or different and are hydrogen, C.sub.1 -C.sub.10 alkyl or haloalkyl and n is an integer from zero to about 10.The method of preparing the compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris(haloalkyl)phosphate in the presence of about 0.01% to about 5% of a phosphite at a temperature from about 0.degree.-200.degree. C. A polyphosphate ester having P--O--P bonds is formed which is then reacted with an epoxide to yield the oligomeric phosphate ester flame retardant compositions.Alternatively, a method of preparing similar compositions comprises reacting P.sub.2 O.sub.5 with a trialkyl or tris(haloalkyl)phosphite at a temperature from about 0.degree. C. to about 200.degree. C.
    Type: Grant
    Filed: November 4, 1981
    Date of Patent: May 3, 1983
    Assignee: Stauffer Chemical Company
    Inventors: Thomas A. Hardy, Fred Jaffe
  • Patent number: 4292036
    Abstract: Flame retardance is imparted to textile materials by impregnating them with a flame retardant composition comprising(a) at least one compound represented by the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently selected from the group consisting of aryl, arylalkyl, alkylaryl, alkenyl and alkyl having from 1 to about 6 carbon atoms and ##STR2## R.sup.3 represents an alkylene group having from 1 to about 5 carbon atoms, and R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, ##STR3## wherein R.sup.6 represents an alkyl group having from 1 to about 4 carbon atoms; provided that not all of said R.sup.4 's and R.sup.5 's are --CH.sub.3 at the same time:(b) an aminoplast; and(c) an acid catalyst; and heating the impregnated textile material sufficiently to cure said flame retardant composition.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: September 29, 1981
    Assignee: Stauffer Chemical Company
    Inventors: Edward N. Walsh, Thomas A. Hardy
  • Patent number: 4083897
    Abstract: N-Alkylated aminoalkylphosphonates having the structural formula: ##STR1## where R.sup.1,R.sup.4 and R.sup.5 are straight or branched lower alkyl having one to five carbon atoms; R.sup.2 and R.sup.3 are selected from the group consisting of straight or branched lower alkyl having one to five carbon atoms and hydrogen and n is the integer 1 or 2, are prepared with acid numbers from about 5 to about 15 by contacting an amine and a phosphite and then adding this to an aqueous solution of an aldehyde or ketone. The reaction temperature is kept below about 70.degree. C. and water is removed under reduced pressure.
    Type: Grant
    Filed: November 10, 1976
    Date of Patent: April 11, 1978
    Assignee: Stauffer Chemical Company
    Inventor: Thomas A. Hardy