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公开(公告)号:CA655173A
公开(公告)日:1963-01-01
申请号:CA655173D
Applicant: HOECHST AG
Inventor: ORTHNER LUDWIG , LANDAUER FRANZ , SCHMIDT ERICH , JUNGHANNS ERNST , REUTER MARTIN
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公开(公告)号:DE1117307B
公开(公告)日:1961-11-16
申请号:DEF0020892
申请日:1956-07-26
Applicant: HOECHST AG
Inventor: HORST KARL , WELLENS HEINO , ORTHNER LUDWIG
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公开(公告)号:CA543285A
公开(公告)日:1957-07-09
申请号:CA543285D
Applicant: HOECHST AG
Inventor: ORTHNER LUDWIG , REUBER RUDOLF
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公开(公告)号:GB1043502A
公开(公告)日:1966-09-21
申请号:GB2510163
申请日:1963-06-24
Applicant: HOECHST AG
Inventor: REUTER MARTIN , WOLF ERHARD , ORTHNER LUDWIG , BEERMANN CLAUS
IPC: C07D233/14
Abstract: The invention comprises cyclo-amidines of the general Formula I wherein R and R1 each represent an alkyl radical, which may be interrupted by a heteroatom or heteroatom group, or a cycloalkyl or aryl radical, which alkyl, cycloalkyl or aryl radicals may be substituted by halogen-free substituents; R2 represents an ethylene or propylene radical which may be substituted or an unsubstituted phenylene radical; R3 represents an alkyl radical containing up to three carbon atoms; and Z represents an acid group containing oxygen. These cyclo-amidines may be prepared by treating a cycloamidine of the general Formula II in the absence of an alkali with a salt of a monohalogen organic acid of the general formula Hal.-R3-Z-M wherein Hal. represents a halogen atom and M represents an ammonium radical, an alkali metal or alkaline earth metal. The reaction may be effected in the presence of a solvent, e.g. water, benzene, acetonitrile and chloroform, but is preferably effected in a melt of the cyclo-amidine reactant at 50 DEG to 150 DEG C. If the cyclo-amidine product is to contain an alcoholic hydroxy group it is also possible to prepare said product by reacting the metallic alcoholate of the corresponding cyclo-amidine of Formula II with a free halogen organic acid of the formula Hal.-R3-Z-H. Specified Z groups are CO2 and SO3, specified hetero atoms and heteroatom groups interrupting R and R1 alkyl radicals are O, N, S and NHCO, and specified substituents in R and R1 are -OH, -OCH3 and -CONH2 groups.
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公开(公告)号:CA717089A
公开(公告)日:1965-08-31
申请号:CA717089D
Applicant: HOECHST AG
Inventor: LANDAUER FRANZ , REUTER MARTIN , ORTHNER LUDWIG
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公开(公告)号:CA671373A
公开(公告)日:1963-10-01
申请号:CA671373D
Applicant: HOECHST AG
Inventor: ORTHNER LUDWIG , HERZBERG HORST
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公开(公告)号:CA656832A
公开(公告)日:1963-01-29
申请号:CA656832D
Applicant: HOECHST AG
Inventor: ORTHNER LUDWIG , WALDMANN KARL , HORST KARL
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公开(公告)号:CA620978A
公开(公告)日:1961-05-30
申请号:CA620978D
Applicant: HOECHST AG
Inventor: ORTHNER LUDWIG , HERZBERG HORST , FREY HANS H
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公开(公告)号:GB868080A
公开(公告)日:1961-05-17
申请号:GB3421457
申请日:1957-11-01
Applicant: HOECHST AG
Inventor: ORTHNER LUDWIG , HORST KARL , WELLENS HEINO ERNST
IPC: C08G12/04 , C08G12/28 , D06M15/423
Abstract: Hardenable condensation products are produced by treating an amine having at least three amino groups to introduce at least two urea groups into it, reacting the product with a long chain compound containing a functional group which reacts with amino or carbonamide groups, and converting the product so obtained into a methylol or substituted methylol derivative by reaction with an aldehyde. Suitable polyamines are diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, tetrapropylene pentamine, polyamino benzenes, polyamino naphthalenes, and products obtained by reacting alcohols or amines with acrylonitrile and reducing the product. Introduction of urea groups into the amine may be effected with urea, nitro-urea or potassium cyanate. Suitable long chain compounds are carboxylic acids, esters, anhydrides, halides or azides, carbamide chlorides, isocyanates, chlorcarbonic acids or methylol compounds. The chains contain 10-18 carbon atoms and may be interrupted or substituted by aromatic, cycloaliphatic or heterocyclic radicals or hetero atoms. Mentioned are stearic acid-N-methylol amide, octadecyl-N-methylol urethane, octadecylchloromethyl ether. If desired the poly-amine may be reacted with the long chain compound before the conversion of amino to urea groups. The products are preferably reacted with formaldehyde. Acetaldehyde and glyoxal are also mentioned. The methylol groups may be etherified by reaction with alcohols, e.g. methyl, ethyl, propyl or butyl alcohol in acid medium. The products of the invention may be applied in aqueous media with acid catalysts to paper, textiles or leather, dried and cured at 80 DEG -170 DEG C. Suitable catalysts are lactic acid, glycollic acid, ammonium nitrate or aluminium sulphate. They may be used together with other aminoplasts, polyvinyl acetate, polyvinyl propionate, polyacrylic esters, polyvinyl alcohol, polyacrylic amide, starch, glue, water-soluble cellulose derivatives, paraffins, or waxes. In Examples (1) diethylene triamine is heated with urea, and the product with stearoyl chloride and then with formalin; (2) is similar using octadecyl isocyanate in place of stearyl chloride. The aqueous emulsion of product is used with hexamethylol melamine and ammonium nitrate; (3) Triethylene tetramine was heated with stearic acid and then with urea and the product with paraformaldehyde; (4) Triethylene tetramine was condensed with urea, octadecyl isocyanate and then formalin; (5) is similar to (4) with stearic acid-N-methylol-amide in place of octadecyl isocyanate; (6) Dipropylene triamine was condensed with urea followed by octadecyl isocyanate and formalin. The product was etherified with methanol and the white paste mixed with paraffin and xylol, and diluted, if desired, with water; (7) Tripropylene tetramine was heated with tetradecyl chloride, then with potassium cyanate and then with formalin or glyoxal; (8) Dipropylene monoethylene tetramine was condensed with urea and then with a mixture of stearyl and palmitoyl chlorides, followed by formalin; (9) Tetraethylene pentamine was heated with urea, with octadecyl isocyanate and then with formaldehyde. The aqueous emulsion was mixed with paraffin xylene and an emulsifier. Uses: The products are used for making paper, leather or textiles water-repellent, giving a soft handle to textiles and giving wet strength to paper.ALSO:Methylol or substituted methylol derivatives of substances prepared by treating polyamines in either order with substances to introduce urea groups and with long-chain substances containing groups which react with amino or with carbonamido groups (see Group IV(a)) are used as aqueous pastes or emulsions to treat textiles to make them, after drying and curing, water-repellent, soft and resistant to scraping or shrinking. In an example cotton poplin is impregnated with an aqueous emulsion of ammonium nitrate and a paste obtained by treating diethylene triamine with urea and then with stearyl chloride and formalin. After drying and heating the fabric has a soft and full handle not affected by repeated washing.
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公开(公告)号:CA600811A
公开(公告)日:1960-06-28
申请号:CA600811D
Applicant: HOECHST AG
Inventor: REUTER MARTIN , ORTHNER LUDWIG
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