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WO2001098388A1 - Reseaux polymeres aldehyde / polyetheramine - Google Patents

Reseaux polymeres aldehyde / polyetheramine Download PDF

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Publication number
WO2001098388A1
WO2001098388A1 PCT/EP2001/007134 EP0107134W WO0198388A1 WO 2001098388 A1 WO2001098388 A1 WO 2001098388A1 EP 0107134 W EP0107134 W EP 0107134W WO 0198388 A1 WO0198388 A1 WO 0198388A1
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WO
WIPO (PCT)
Prior art keywords
optionally
formula
formaldehyde
valent organic
networks according
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.)
Ceased
Application number
PCT/EP2001/007134
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German (de)
English (en)
Inventor
Serguei Evsioukov
Gunnar Schornick
Jan Nouwen
Arthur Höhn
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to AU2001283881A priority Critical patent/AU2001283881A1/en
Publication of WO2001098388A1 publication Critical patent/WO2001098388A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/04—1,2,3-Triazines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
    • C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
    • C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
    • C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
    • C08G16/0225—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
    • C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
    • C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
    • C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
    • C08G16/0231—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/0644—Poly(1,3,5)triazines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065—Preparatory processes

Definitions

  • the invention relates to polymeric aldehyde / polyetheramine networks.
  • aldehydes such as formaldehyde
  • amines such as monoamines and aliphatic diamines
  • DE-A-26 45 170 relates to a vulcanization accelerator for rubbers.
  • the accelerator comprises a reaction product of an aldehyde with phenylenediamine or an aliphatic 1,2- or 1,3-diamine. Ethylene diamine or propylene diamine are preferably used as the aliphatic diamine.
  • the aldehyde used is preferably formaldehyde.
  • US 3,461,100 relates to condensation products of aldehydes or ketones with diamines and monoamines.
  • the water-insoluble, but soluble in aliphatic hydrocarbons polymer materials are used as protective coatings, especially for metals. They are obtained by condensing an aldehyde or ketone with a diamine in an organic reaction medium. As a by-product, water is continuously removed. For example, formaldehyde and hexamethylene diamine are implemented.
  • JP-A-63 192 750 relates to the preparation of polymeric tertiary amines which have hexahydrotriazm units. The connections are obtained by
  • US 5,830,243 relates to fuel compositions which contain N-substituted perhydro-s-triazine Neritatien. These are produced by reacting an aldehyde with at least one ether amine which has a maximum of three primary amino groups. The Neritatien serve to reduce the formation of deposits in injection engines.
  • the object of the present invention is to provide polymeric networks whose properties can be adjusted over a wide range.
  • materials based on aldehydes and amines that have novel properties are to be made available.
  • polymeric networks which can be obtained by condensing an aldehyde or a mixture of aldehydes or precursors thereof with an amine-containing component A, optionally in the presence of a solvent S, component A comprising at least one polyetheramine (I ), obtainable by alkoxylation of polyols of the general formula
  • n is an integer from 1 to 20,
  • r is an integer value from 1 to 19 with the proviso that 1 ⁇ r ⁇ q.
  • Formaldehyde or a mixture of aldehydes containing formaldehyde is preferably used as the aldehyde.
  • Corresponding precursors to these compounds can also be used.
  • Such precursors are, for example, the cyclic trimer form, 1,3,5-trioxane or polymeric forms of formaldehyde, the so-called paraformaldehyde.
  • Acetals such as diethoximethane can also be used.
  • the aldehydes are condensed with component A.
  • the ratio is preferably chosen so that stoichiometric amounts of reactive aldehyde groups and amino groups are present. Deviations from the stoichiometry of up to 20 mol%, preferably up to 10 mol%, can also lead to usable polymer networks.
  • Component A contains at least one polytheramine (I), obtainable by alkoxylation of polyols of the general formula
  • the polyetheramines (I) preferably have an average molecular weight (M n ) of 200 to 20,000 g / mol, particularly preferably 500 to 10,000 g / mol, in particular 1000 to 5000 g / mol.
  • s preferably has an integer value from 4 to 10, particularly preferably from 4 to 6.
  • Y 3 is an s-valent organic radical. This can be any suitable s-valent organic residue that is suitable for alkoxylation and subsequent Amination is suitable. It is preferably derived from C 4 - 5 o-alkylene radicals, particularly preferably C 4 - 3 o-alkylene radicals, in particular C 4 . 2 o-alkylene residues, which can be linear, branched or cyclic. In addition, non-adjacent CH 2 groups in the alkylene radicals can be replaced by oxygen groups, sulfur, -NH-, -N (-CC- 4 -alkyl) -, CO, optionally substituted arylene and / or optionally substituted heteroarylene.
  • Y is preferably an alkylene radical which is linear or branched and in which there is no more than one hydroxyl group on a carbon atom.
  • These are preferably linear or single-branched aliphatic carbon backbones which have 4 to 10, in particular 5 to 6, carbon atoms.
  • the aliphatic polyols are particularly preferably selected from pentaerythritol and sugar alcohols with at least 4 hydroxyl groups, especially tetrites, pentites or hexites. Mixtures of these can also be used.
  • suitable tetrites are erythritol and threitol.
  • Preferred pentites are rebit, arabite and xylitol.
  • Preferred hexites are dulcite, mannitol and sorbitol.
  • Pentaerythritol and sorbitol, especially D-sorbitol are particularly preferably used. All other alcohols derived from corresponding sugars by reduction can also be used. If appropriate, the sugars themselves can also be used, provided that they have the required number of hydroxyl groups.
  • the polyols are alkoxylated with 1 to 100 mol, preferably 1 to 80 mol, in particular 1 to 60 mol, per mol of hydroxyl groups, of one or more C 8 alkoxides.
  • Preferred alkoxides are ethylene oxide, propylene oxide and butylene oxide, especially ethylene oxide and propylene oxide. Ethylene oxide, propylene oxide or mixtures thereof are particularly preferably used.
  • Statistically alkoxylated products can be obtained by using alkylene oxide mixtures. Block products can also be produced by first alkoxylation with an alkylene oxide and subsequent alkoxylation with another alkylene oxide, etc. Suitable alkoxylation processes are known.
  • the alkoxylated polyols are aminated with ammonia, so that 50 to 100%, preferably 80 to 100%, of the hydroxyl groups present are aminated and there are at least 2, preferably at least 3 primary amino groups per molecule.
  • the polyether polyols are aminated such that there are at least two terminal primary amino groups.
  • the amination is preferably carried out with ammonia in the presence of an inorganic catalyst.
  • the amination can be carried out in a solvent such as cyclohexane.
  • two polyol molecules can also be condensed with one ammonia molecule.
  • a polyetheramine is obtained which, in addition to terminal primary amino groups, has one or more internal secondary amino groups.
  • the secondary amino groups can be condensed with further polyol molecules. In this case there are at least primary and tertiary amino groups in the molecule.
  • Compounds can also be obtained in which primary, secondary and tertiary amino groups are present side by side. The products obtained are predominantly determined by the quantitative ratio of the starting materials and the reaction conditions. The ratio of ether units to amino groups can also be adjusted via the molecular weight of the polyol used.
  • reaction of amines (I) with the aldehydes can be carried out without solvent or in the presence of a solvent (S).
  • a solvent for example, water-miscible solvents are used as the solvent (S).
  • Formaldehyde is used, for example, as an aqueous formalin solution.
  • Acetone, dioxane, polyether glycols, alcohols such as n-propanol and similar solvents can also be used as solvents, which, if miscible, can contain water.
  • the reaction is preferably carried out at temperatures in the range from 0 to 70 ° C., particularly preferably 10 to 50 ° C., in particular 15 to 30 ° C.
  • the polyetheramine is placed in the solvent and then mixed with formaldehyde in solid or gaseous or preferably in dissolved form. Acetals can also be used in liquid form. If desired, the reaction can be carried out in the presence of basic catalysts. In addition to the amines (I), amines of the formula (II) can also be used.
  • Y 1 denotes n-valent organic radicals which are derived from C 2 -3ooo-alkylene radicals, preferably C -oooo-alkylene radicals, in particular C 2 -oooo-alkylene radicals, in which non-adjacent CH 2 -Groups can be replaced by oxygen, sulfur, -NH-, -N (-CC-4-alkyl) -, -CO-, optionally substituted arylene and / or optionally substituted heteroarylene.
  • Y 1 denotes n-valent organic radicals which are derived from oligomers or polymers of ethylene, propylene or mixtures of these monomers with an average number of 1000 of these monomer units are particularly preferably used.
  • Amines of the formula (III) can also be used.
  • This is preferably Neritatien in which Y 2 denotes q-valent organic residues derived from C, -, preferably 3-ooo alkylene C - ⁇ ooo-alkylene, especially C2-1 00 - alkylene radicals are derived, in which non-adjacent CH 2 groups can be replaced by oxygen, sulfur, - ⁇ H-, - ⁇ (C ⁇ - 4 alkyl) -, - CO-, optionally substituted arylene and / or optionally substituted heteroarylene.
  • the q-valent organic radicals Y 2 are preferably derived from oligomers or polymers of ethylene, propylene or mixtures of these monomers with an average number of up to 1000 of these monomer units.
  • the functional monovalent radicals Z can be selected from the group consisting of -OH, -SH, -COO-C ⁇ - ⁇ 2 alkyl, -SO 3 -C M2 alkyl and PO (O-C ⁇ - ⁇ 3 alkyl) ) 2 .
  • the Z radicals can also be selected from neutralized acid radicals, such as carboxyl or sulfonyl groups neutralized with alkali or amines or ammonia.
  • the polyetheramine 1 is derived from pentaerythritol and has a molecular weight of 5000 (number average). It is statistically alkoxylated with ethylene oxide and propylene oxide in a molar ratio of 4: 1 and subsequently aminated with stoichiometric amounts of ammonia.
  • the polyetheramine 2 corresponds to the polyetheramine 1, but has a number-average molecular weight of 15,000.
  • the polyetheramine 3 is derived from sorbitol, which is propoxylated with 12 mol of propylene oxide and then stoichiometrically aminated.
  • the amine number is about 350 mg KOH / g, the acetylation number about 400 mgKOH / g.
  • the product has a melting point of -5 to -10 ° C and a boiling point above 200 ° C.
  • the pH at 20 ° C in a concentration of 10 g / 1 is about 11.4.
  • a mixture of the polyetheramine 1 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 1 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 1 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both Mixtures were added at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 1 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 1 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 1 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 2 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 2 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 2 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 2 to formaldehyde was 1: 1. After about 5 min. the reaction product became solid but remained sticky. It was yellow in color.
  • a mixture of the polyetheramine 2 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 2 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 3 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both Mixtures were put together at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 3 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 3 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 3 to formaldehyde is 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 3 to formaldehyde was 1: 1. After about 5 min. the reaction product became solid but remained sticky. The product turned yellow after three days.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 3 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both mixtures were combined at room temperature, mixed well and poured into a bowl.
  • the molar ratio of polyetheramine 3 to formaldehyde was 1: 1.
  • a mixture of the polyetheramine 3 and acetone was produced.
  • a mixture of formalin (37% formaldehyde in water) and acetone was also prepared. Both Mixtures were put together at room temperature, mixed well and poured into a bowl. The molar ratio of polyetheramine 3 to formaldehyde was 1: 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Emergency Medicine (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

Réseaux polymères qui peuvent être obtenus par condensation d'un aldéhyde ou d'un mélange d'aldéhydes ou de précurseurs d'aldéhydes avec un constituant A contenant une amine, éventuellement en présence d'un solvant S. Le constituant A contient au moins une polyétheramine (I) obtenue par alcoxylation de polyols de formule générale Y<3>(-OH)s dans laquelle Y<3> représente une reste organique de valence s, s représente un nombre entier de 4 à 20 avec 1 à 100 moles par mole de groupes hydroxyle d'un ou plusieurs oxydes d'alkylène C1-8, puis par amination de ces polyols avec de l'ammoniaque, si bien que 50 à 100 % des groupes hydroxyle existants sont aminés et que deux groupes amino primaires au moins sont présents par molécule, éventuellement au moins une amine de formule Y<1>(-NH2)n et éventuellement au moins une amine de formule (Z-)(q-r)Y<2>(-NH2)r. Dans ces formules, Y<1> représente des restes organiques de valence n, Y<2> représente des restes organiques de valence q, Z représente un reste fonctionnel monovalent, n représente un nombre entier de 1 à 20, q représente un nombre entier 2 à 20 et r représente un nombre entier de 1 à 19, à condition que 1 </= r < q.
PCT/EP2001/007134 2000-06-23 2001-06-22 Reseaux polymeres aldehyde / polyetheramine Ceased WO2001098388A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001283881A AU2001283881A1 (en) 2000-06-23 2001-06-22 Polymeric aldehyde/polyetheramine networks

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2000130684 DE10030684A1 (de) 2000-06-23 2000-06-23 Polymere Aldehyd/Polyetheramin-Netzwerke
DE10030684.5 2000-06-23

Publications (1)

Publication Number Publication Date
WO2001098388A1 true WO2001098388A1 (fr) 2001-12-27

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PCT/EP2001/007134 Ceased WO2001098388A1 (fr) 2000-06-23 2001-06-22 Reseaux polymeres aldehyde / polyetheramine

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DE (1) DE10030684A1 (fr)
WO (1) WO2001098388A1 (fr)

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US7332467B2 (en) 2004-12-17 2008-02-19 Procter & Gamble Company Hydrophilically modified polyols for improved hydrophobic soil cleaning
US7358220B2 (en) 2004-02-04 2008-04-15 Procter & Gamble Company Alkoxylated polyol containing bleach activating terminating functional groups
US7439219B2 (en) * 2003-12-19 2008-10-21 The Procter & Gamble Company Modified alkoxylated polyol compounds
US7538080B2 (en) 2003-12-19 2009-05-26 The Procter & Gamble Company Modified alkoxylated polyol compounds
US9120897B1 (en) 2014-05-27 2015-09-01 International Business Machines Corporation Preparation of thioether polymers
US9120899B1 (en) 2014-06-02 2015-09-01 International Business Machines Corporation Preparation of functional polysulfones
US9228034B1 (en) 2014-10-09 2016-01-05 International Business Machines Corporation Hexahydrotriazine, dithiazine, and thioether functionalized materials
US9243107B2 (en) 2013-10-10 2016-01-26 International Business Machines Corporation Methods of preparing polyhemiaminals and polyhexahydrotriazines
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GB928112A (en) * 1960-05-17 1963-06-06 Ici Ltd Condensation products
GB1033912A (en) * 1962-07-12 1966-06-22 Bayer Ag Process for the preparation of polypropylene ether amines
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