GB558423A - Diamines - Google Patents

Diamines

Info

Publication number
GB558423A
GB558423A GB6986/42A GB698642A GB558423A GB 558423 A GB558423 A GB 558423A GB 6986/42 A GB6986/42 A GB 6986/42A GB 698642 A GB698642 A GB 698642A GB 558423 A GB558423 A GB 558423A
Authority
GB
United Kingdom
Prior art keywords
bis
ethane
benzene
ether
halogenoethoxy
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
GB6986/42A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB558423A publication Critical patent/GB558423A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings

Abstract

558,423. Diamines. DU PONT DE NEMOURS & CO., E. I. May 22, 1942, No. 6986. Convention date, April 29, 1941. [Classes 2 (iii) and 15 (ii)] Disecondary diamines are prepared by reaction under anhydrous conditions of a primary aliphatic monoamine, and an organic dihalide in which the halogens (chlorine, bromine, or iodine) are attached to methylene groups and are separated by at least six carbon or carbon and oxygen atoms, the primary amine being present in the reaction mixture in amount of at least 20 moles per mole of the dihalide. Excess caustic is added and the diamine extracted with a solvent. In examples N:N<SP>1</SP>-dimethylhexamethylenediamine is prepared from monomethylamine and hexamethylene dibromide N:N<SP>1</SP>-dimethyl-p-xylylenediamine from monomethylamine and p-xylylene dichloride, N:N<SP>1</SP>-diethyl-decamethylenediamine, N:N<SP>1</SP>-diisobutylhexamethylenediamine, N:N<SP>1</SP>-diethyltriglycoldiamine from triglycol dichloride and monoethylamine, N:N' - dimethyltri - glycoldiamine, N:N<SP>1</SP> - diethyl-p - xylylene - diamine, N:N<SP>1</SP>- dimethyldecamethylenedia - mine, N:N<SP>1</SP>-diethylhexamethylenediamine, N:N<SP>1</SP>-di-n-amylhexamethylenediamine, and N:N<SP>1</SP>-dibenzylhexamethylenediamine. Solvents may be used in the reaction. A list is given of amines and dihalides, including bis (3-halo, genopropyl) ether, bis (4-halogenobutyl) etherbis (2-halogenoethoxy) ethane, bis (3-halogenopropoxy) ethane, bis (2-halogenoethoxy) propane, p-bis (halogenomethoxy) benzene, m-bis-(halogenomethoxy) benzene, p-bis (2- halogenoethoxy) benzene, 2-amyl-p-bis (halogenomethoxy) benzene, bis (3-chloropropyl) ether, bis (4-bromobutyl) ether, bis (2-chloroethoxy) ethane, and bis (3-chloropropoxy) ethane. The amines obtained with ether-type dihalides when reacted with dicarboxylic acids form polyamides which act as plasticizers for other polyamides such as polyhexamethyleneadipamide and improve the receptivity of the polyamide blends for acid, direct and vat dyes.
GB6986/42A 1941-04-29 1942-05-22 Diamines Expired GB558423A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US558423XA 1941-04-29 1941-04-29

Publications (1)

Publication Number Publication Date
GB558423A true GB558423A (en) 1944-01-05

Family

ID=22000505

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6986/42A Expired GB558423A (en) 1941-04-29 1942-05-22 Diamines

Country Status (1)

Country Link
GB (1) GB558423A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497292A (en) * 1946-05-07 1950-02-14 Du Pont Preparation of n-isobutyl hexamethylenediamines
US2766288A (en) * 1952-11-12 1956-10-09 Gen Mills Inc Bis-tertiary aminoalkoxy alkanes
WO1992002486A1 (en) * 1990-08-09 1992-02-20 Ethyl Corporation Processes for preparing secondary and tertiary amines
CN110642722A (en) * 2019-10-18 2020-01-03 山东省化工研究院 Method for preparing N, N-tetramethyl decamethylene diamine

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497292A (en) * 1946-05-07 1950-02-14 Du Pont Preparation of n-isobutyl hexamethylenediamines
US2766288A (en) * 1952-11-12 1956-10-09 Gen Mills Inc Bis-tertiary aminoalkoxy alkanes
WO1992002486A1 (en) * 1990-08-09 1992-02-20 Ethyl Corporation Processes for preparing secondary and tertiary amines
CN110642722A (en) * 2019-10-18 2020-01-03 山东省化工研究院 Method for preparing N, N-tetramethyl decamethylene diamine

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