GB1023210A - Process for the production of salts of primary and secondary aminoalkyl esters of polymerisable carboxylic acids - Google Patents

Process for the production of salts of primary and secondary aminoalkyl esters of polymerisable carboxylic acids

Info

Publication number
GB1023210A
GB1023210A GB45162/64A GB4516264A GB1023210A GB 1023210 A GB1023210 A GB 1023210A GB 45162/64 A GB45162/64 A GB 45162/64A GB 4516264 A GB4516264 A GB 4516264A GB 1023210 A GB1023210 A GB 1023210A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
radical
cooanhr4
phenyl
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
GB45162/64A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB1023210A publication Critical patent/GB1023210A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Polymers are prepared by radical polymerization of compounds R1CH=CR3.COOANHR4.HX, where R1 is hydrogen, C1- 6 alkyl or a -COOANHR4.HX radical, R3 is hydrogen, methyl or a -CH2COOANHR4.HX radical, R4 is hydrogen, normal alkyl, aralkyl, phenyl or substituted phenyl, A is a C2- 10 straight or branched alkylene group, and X is Cl or Br (see Division C2). Examples polymerize b -aminoethyl methacrylate hydrochloride in bulk and in an aqueous medium which contains sodium formaldehyde sulphoxylate, p - menthanehydroperoxide, potassium ferrocyanide and bleaching earth.ALSO:The invention comprises the salts of formula R1CH=CR3.COOANHR4.HX, where R1 is hydrogen, C1-6 alkyl or a -COOANHR4.HX radical, R3 is hydrogen, methyl or a -CH2COOANHR4.HX radical, R4 is hydrogen, normal alkyl, aralkyl, phenyl or phenyl substituted with e.g. Cl, Br or C1-6 alkyl, A is a C2-10 straight or branched alkylene group, and X is Cl or Br; and their production by reacting anhydrous HOANHR4.HX with R5CH=CR6.-COX (where R5 is hydrogen, C1-6 alkyl or -COX and R6 is hydrogen, methyl or -CH2COX) at 70-120 DEG C. in the presence of metallic copper or a copper salt; an anhydrous inert organic solvent may be used. The copper stabilizes the product against polymerization. The alkanolamine hydrohalides may be prepared by introducing dry hydrogen halide into the alkanolamine, and rendered anhydrous by treatment with SOCl2. In a comparative test ClCH2CH2NH2.HCl is obtained from HOCH2CH2NH2.HCl, H2O and SOCl2 in the presence of copper powder.
GB45162/64A 1963-11-27 1964-11-05 Process for the production of salts of primary and secondary aminoalkyl esters of polymerisable carboxylic acids Expired GB1023210A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF41384A DE1235896B (en) 1963-11-27 1963-11-27 Process for the preparation of primary or secondary aminoalkyl ester salts of acrylic, methacrylic, crotonic, itaconic or fumaric acid

Publications (1)

Publication Number Publication Date
GB1023210A true GB1023210A (en) 1966-03-23

Family

ID=7098649

Family Applications (1)

Application Number Title Priority Date Filing Date
GB45162/64A Expired GB1023210A (en) 1963-11-27 1964-11-05 Process for the production of salts of primary and secondary aminoalkyl esters of polymerisable carboxylic acids

Country Status (5)

Country Link
BE (1) BE656266A (en)
DE (1) DE1235896B (en)
FR (1) FR1415144A (en)
GB (1) GB1023210A (en)
NL (1) NL142400B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002003464A (en) * 2000-04-17 2002-01-09 Showa Denko Kk (meth)acryloyl group-containing carbamic acid halides and method for producing the same
CN103319357A (en) * 2013-07-09 2013-09-25 南宁凯林杰机械化工有限公司 Monoethanolamine fumarate synthesized from C4 fraction and application thereof in metal processing liquid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4060529A (en) * 1974-06-06 1977-11-29 Rohm And Haas Company Polymerization inhibitors for N-substituted aminoalkyl acrylic monomers

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE17297C (en) * E. und B. HOLMES in Bufifalo, New-York U. S. A Innovations in machines for processing the fabric surfaces on barrel staves
US2458420A (en) * 1947-11-22 1949-01-04 Eastman Kodak Co Acrylic ester-amides and polymers thereof
US2718516A (en) * 1952-11-08 1955-09-20 Rohm & Haas Isocyanato esters of acrylic, methacrylic, and crotonic acids
DE1002326B (en) * 1954-06-29 1957-02-14 Bayer Ag Process for the production of unsaturated methyl olethers
US2806018A (en) * 1954-07-09 1957-09-10 American Cyanamid Co Nu-subistuted acrylamide and polymerization products thereof
DE1102157B (en) * 1954-12-04 1961-03-16 Bayer Ag Process for the preparation of unsaturated acylaminomethyl amines
GB823595A (en) * 1955-10-07 1959-11-11 Ici Ltd New and improved ester salts and their production
DE1085149B (en) * 1956-06-05 1960-07-14 American Cyanamid Co Process for the preparation of pure crystalline methylolacrylic acid amide
GB852384A (en) * 1957-07-16 1960-10-26 Rohm & Haas Process for preparing dihydroxy alkyl acrylates and methacrylates

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002003464A (en) * 2000-04-17 2002-01-09 Showa Denko Kk (meth)acryloyl group-containing carbamic acid halides and method for producing the same
CN103319357A (en) * 2013-07-09 2013-09-25 南宁凯林杰机械化工有限公司 Monoethanolamine fumarate synthesized from C4 fraction and application thereof in metal processing liquid

Also Published As

Publication number Publication date
NL142400B (en) 1974-06-17
NL6413809A (en) 1965-05-28
FR1415144A (en) 1965-10-22
DE1235896B (en) 1967-03-09
BE656266A (en) 1965-05-26

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