GB1043054A - Plasticizing esters and plasticized resinous compositions - Google Patents

Plasticizing esters and plasticized resinous compositions

Info

Publication number
GB1043054A
GB1043054A GB12385/64A GB1238564A GB1043054A GB 1043054 A GB1043054 A GB 1043054A GB 12385/64 A GB12385/64 A GB 12385/64A GB 1238564 A GB1238564 A GB 1238564A GB 1043054 A GB1043054 A GB 1043054A
Authority
GB
United Kingdom
Prior art keywords
nitrilotripropionate
given
hydrocarbon groups
alcohol
ammonia
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB12385/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB1043054A publication Critical patent/GB1043054A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to compounds of the formula N(CH2CH2COOR1)(CH2CH2COOR2) (CH2CH2COOR3) in which R1, R2 and R3 are identical or differen hydrocarbon groups (or halogen- or nitro-substituted hydrocarbon groups) free of acetylenic unsaturation. R1, R2 and R3 may be alkyl, aralkyl, aryl, alkaryl or alkenyl groups, and examples of each type of group are given. The compounds may be prepared by treating acrylic esters with ammonia, the molar proportion of ester being at least three times that of the ammonia. This reaction may be effected at 5-150 DEG C., preferably in a solvent and in the presence of a catalyst, which may be an ammonium, alkali-metal or alkaline-earth metal salt or a quaternary ammonium compound, examples of each of which are given. Alternatively, the compounds may be prepared by re-esterifying a previously prepared nitrilotripropionate with an alcohol of higher molecular weight, optionally in the presence of a re-esterification catalyst, e.g. a sodium hydrogen titanium alkoxide. In typical examples, (1) methyl acrylate is heated with ammonia in methanol in the presence of ammonium acetate to yield trimethyl nitrilotripropionate and (2) trimethyl nitrilotripropionate is heated with 2-ethylhexanol in the presence of a sodium hydrogen titanium mixed alkoxide to yield tri-2-ethylhexyl nitrilotripropionate. The products are useful as plasticizers for polyvinyl chloride compositions (see Division C3).ALSO:As plasticizers for polyvinyl chloride or compositions containing a major proportion thereof, use is made of nitrilotripropionates of the formula N(CH2CH2COOR1) (CH2CH2COOR2) (CH2CH2COOR3), in which R1, R2 and R3 are identical or different hydrocarbon groups (or halogen- or nitro-substituted hydrocarbon groups) containing at least 6 carbon atoms and free of acetylenic unsaturation (see Division C2. R1, R2 and R3 may be alkyl, aralkyl, aryl, alkaryl or alkenyl groups, and instances of each type of group are given. Comparative experimental results are given of the use of the nitrilotripropionates of 2-ethylhexyl alcohol, isooctyl alcohol, isodecyl alcohol and a mixture of m-octyl and n-decyl alcohols.
GB12385/64A 1963-04-02 1964-03-24 Plasticizing esters and plasticized resinous compositions Expired GB1043054A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US26985563A 1963-04-02 1963-04-02
US29646163A 1963-07-22 1963-07-22
US429887A US3278478A (en) 1963-04-02 1965-02-02 Vinyl resins plasticized with trisubstituted nitrilotripropionates

Publications (1)

Publication Number Publication Date
GB1043054A true GB1043054A (en) 1966-09-21

Family

ID=27402231

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12385/64A Expired GB1043054A (en) 1963-04-02 1964-03-24 Plasticizing esters and plasticized resinous compositions

Country Status (4)

Country Link
US (1) US3278478A (en)
BE (1) BE642774A (en)
GB (1) GB1043054A (en)
NL (1) NL6400875A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104252A (en) * 1977-09-26 1978-08-01 Borg-Warner Corporation Olefin polymer stabilizer
IT1137492B (en) * 1981-05-26 1986-09-10 Maria Curti COMPOUNDS WITH SIMILAR GABA ACTIVITY, PROCEDURE TO PREPARE THEM AND PHARMACEUTICAL COMPOSITIONS THAT INCLUDE THEM
GB9116684D0 (en) * 1991-08-02 1991-09-18 Exxon Chemical Patents Inc Corrosion inhibitors
GB9114012D0 (en) * 1991-06-28 1991-08-14 Exxon Chemical Patents Inc Amine adducts as corrosion inhibitors
EP0752465A1 (en) * 1995-06-01 1997-01-08 The Procter & Gamble Company Betaine esters for delivery of alcohols
ATE211728T1 (en) * 1995-11-02 2002-01-15 Procter & Gamble AMINO ESTERS OF PERFUME ALCOHOL AND THEIR USE IN CLEANING AND DETERGENT COMPOSITIONS
CA3006395C (en) 2008-11-07 2022-05-31 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
DK2691443T3 (en) 2011-03-28 2021-05-03 Massachusetts Inst Technology CONJUGIATED LIPOMERS AND USES OF THESE
PE20181541A1 (en) * 2011-10-27 2018-09-26 Massachusetts Inst Technology DERIVATIVES OF AMINO ACIDS FUNCTIONALIZED IN THE N TERMINAL, CAPABLE OF FORMING DRUG ENCAPSULATING MICROSPHERES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2296331A (en) * 1938-05-03 1942-09-22 Gen Anilline & Film Corp Softener for halogen-containing high-molecular weight, organic compounds

Also Published As

Publication number Publication date
NL6400875A (en) 1964-10-05
US3278478A (en) 1966-10-11
BE642774A (en) 1964-07-22

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