WO2010101560A1 - Bis[(alkylamino)alkyl]amines - Google Patents

Bis[(alkylamino)alkyl]amines Download PDF

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Publication number
WO2010101560A1
WO2010101560A1 PCT/US2009/035633 US2009035633W WO2010101560A1 WO 2010101560 A1 WO2010101560 A1 WO 2010101560A1 US 2009035633 W US2009035633 W US 2009035633W WO 2010101560 A1 WO2010101560 A1 WO 2010101560A1
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WO
WIPO (PCT)
Prior art keywords
bis
amine
methyl
aliphatic
group
Prior art date
Application number
PCT/US2009/035633
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English (en)
Inventor
William R. Brown
John Y. Lee
Paul L. Wiggins
Original Assignee
Albemarle Corporation
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 Albemarle Corporation filed Critical Albemarle Corporation
Priority to PCT/US2009/035633 priority Critical patent/WO2010101560A1/fr
Publication of WO2010101560A1 publication Critical patent/WO2010101560A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3234—Polyamines cycloaliphatic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/325—Polyamines containing secondary or tertiary amino groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/02—Polyureas
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • Preferred bis [(alkylideneimino)alkyl] amines include bis[2-(2- butylideneamino)ethyl]amine, bis[2-(3-methyl-2-butylideneamino)ethyl]amine, bis[2-(3,3- dimethyl-2-butylideneamino)ethyl]amine, and bis[2-(4-methyl-2-pentylidene- amino)ethyl] amine.
  • Aliphatic secondary diamines are component (a).
  • the aliphatic secondary diamines are alkyl secondary diamines where the alkyl portion of the diamine is aliphatic, where "alkyl portion” refers to the moiety to which the amino groups are bound.
  • the alkyl portion of the aliphatic diamine can be cyclic, branched, or, preferably, straight chain.
  • the alkyl portion of the diamine is cyclic, the cyclic moiety can be a single ring, fused rings, bicyclic rings, or a tricyclic system (which tricyclic system can contain fused rings and/or bicyclic rings).
  • the amino groups may be attached directly to the ring, or one or both amino groups may be bound to a group that is a substituent of the ring; it is preferred that at least one of the amino groups is bound to the ring.
  • the aliphatic secondary diamine has about eight to about forty carbon atoms; more preferably, the aliphatic secondary diamine has about ten to about twenty-five carbon atoms.
  • Particularly preferred aliphatic secondary diamines have cyclic or straight chain alkyl portions and have about ten to about twenty-five carbon atoms.
  • the amino alkyl groups of the aliphatic secondary diamine can be cyclic, branched, or straight chain.
  • Aliphatic secondary diamines that can be used in this invention include, but are not limited to, N,N'-diisopropylethylenediamine, N,N'-di-sec-butyl-l,2-diaminopropane, N,N'-di(l-cyclopropylethyl)-l,5-diaminopentane, N,N'-di(3,3-dimethyl-2-butyl)-l,5- diamino-2-methylpentane, N,N'-diisopropyl-l,6-diaminohexane N,N'-di-sec-butyl-l ,6- diaminohexane, N,N'-di(4-methyl-2-pentyl)-l ,6-diaminohexane, N,N'-di(3-pentyl)-2,5- dimethyl-2,5-hexan
  • Aliphatic primary diamines for component (b) are alkyl primary diamines where the alkyl portion of the diamine is aliphatic.
  • the alkyl portion of the aliphatic diamine can be cyclic, branched, or straight chain.
  • the aliphatic primary diamine has about four to about thirty carbon atoms; more preferably, the aliphatic primary diamine has about six to about twenty carbon atoms.
  • Particularly preferred aliphatic diamines have cyclic or straight chain alkyl portions and have about four to about ten carbon atoms.
  • Suitable aliphatic primary diamines include, but are not limited to, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1 ,4-diaminobutane, 1,5- diaminopentane, l,5-diamino-2-methylpentane, 1,6-diaminohexane, 2,5-dimethyl-2,5- hexanediamine, 1,2-diaminocyclohexane, 1 ,3-diaminocyclohexane, 1,4- diaminocyclohexane, 2,4-diethyl-6-methyl-l,3-cyclohexanediamine, 4,6-diethyl-2-methyl- 1 ,3-cyclohexanediamine, 1 ,3-cyclohexanebis(methylamine), 1 ,4-cyclohexanebis- (methylamine), isophorone diamine (
  • Particularly preferred amino hydrocarbyl groups are isopropyl and sec-butyl.
  • Aromatic secondary diamines with two secondary amino groups on one benzene ring preferably have the secondary amino groups meta relative to each other.
  • the amino hydrocarbyl group preferably is a straight chain or branched chain alkyl group having from three to about six carbon atoms.
  • Preferred aromatic secondary diamines in which one secondary amino group is on each of two benzene rings, where the two benzene rings are connected via an alkylene bridge have both secondary amino groups para relative to the alkylene bridge.
  • a particularly preferred aromatic secondary diamine is a compound in which the alkylene bridge is a methylene group; this is especially preferred when the amino hydrocarbyl groups are isopropyl or sec-butyl groups.
  • the alkyl groups can have from one to about twenty carbon atoms; preferably, the alkyl groups have from one to about six carbon atoms.
  • Suitable aromatic primary diamines of this type having both amino groups on one benzene ring include, but are not limited to, 1 ,2-benzenediamine, 1,3-benzenediamine, 1,4-benzenediamine, 4-ethyl-l ,2-benzenediamine, 2-isopropyl-l,3-benzenediamine, 4-tert- butyl- 1,3-benzenediamine, 2 -pentyl- 1,4-benzenediamine, 4,5-dihexyl-l,2- benzenediamine, 4-methyl-5-heptyl-l,3-benzenediamine, 4, 6-di- n- propyl- 1,3- benzenediamine, 2,5-dioctyl-l,4-benzenedi
  • aromatic primary diamine that can be used in this invention, which is a preferred type of aromatic primary diamine, is an aromatic primary diamine in which each position ortho (immediately adjacent) to an amino group bears a alkyl group, and which aromatic primary diamine either is in the form of one benzene ring having two amino groups on the ring, which amino groups are meta or para relative to each other, or is in the form of two benzene rings connected by an alkylene bridge and having one amino group on each ring.
  • the alkyl groups on the benzene rings (adjacent to the amino groups) generally have up to about twenty carbon atoms, and the alkyl groups may be the same or different.
  • the polyol or polyetheramine, chain extender composition, and when used, optional ingredients are blended together to form a first mixture, followed by blending this first mixture with the isocyanate to form a second mixture; this second mixture is allowed to cure.
  • the isocyanate and the polyol or polyetheramine are blended together to form a prepolymer, which prepolymer is then mixed together with the chain extender composition to form the desired polymer.
  • IPDI isophorone diisocyanate
  • isocyanates examples include isophorone diisocyanate (IPDI).
  • Isocyanate-reactive polyols and polyetheramines (sometimes referred to as amine-terminated polyols) that are typically used in making polyurethanes, polyureas, and polyurea-urethanes range in molecular weight from about 60 to over 6,000.
  • the polyols can be dihydric, trihydridic, or polyhydric polyols, but are usually dihydric.
  • polystyrene foams examples include poly(ethyleneoxy) glycols, dipropylene glycol, poly(propyleneoxy) glycols, dibutylene glycol, poly(butyleneoxy) glycols, and the polymeric glycol from caprolactone, commonly known as polycaprolactone.
  • the polyetheramines used to make polyurethanes, polyureas, and polyurea-urethanes are amine-capped polyols which are the reaction product of a polyol and then an amine with alkylene oxides as well as amine-capped hydroxyl-containing polyesters.
  • Polyetheramines typically have a molecular weight of about 200 to about 6000.
  • Preferred polymers formed by this invention are formed when bis[2-(2- butylamino)ethy I)] amine and N,N'-di-(3,3-dimethyl-2-butyl)-l,6-diaminohexane or bis[2-
  • Example 2 and 2A formulations provide adequate coatings on new and rusty pipes. Application of the coating was uniform and the coating itself was semi-transparent. Coating opacity can be modified by using different spray conditions, spary equipment, and/or fillers and pigments. [0086] Physical properties of the coatings were obtained by spraying the formulations of 2 and 2A on a fiat stainless steel mold that was coated with a release agent. The coatings were removed from the mold prior to testing. The physical properties are shown in Table 1 below.
  • Tecnate 785 is an IPDI-based (isophorone diisocyanate) prepolymer having about 15 wt% free NCO content (Isotec International, Canton, Ga)
  • the term "about" modifying the quantity of an ingredient in the compositions of the invention or employed in the methods of the invention refers to variation in the numerical quantity that can occur, for example, through typical measuring and liquid handling procedures used for making concentrates or use solutions in the real world; through inadvertent error in these procedures; through differences in the manufacture, source, or purity of the ingredients employed to make the compositions or carry out the methods; and the like.
  • the term about also encompasses amounts that differ due to different equilibrium conditions for a composition resulting from a particular initial mixture. Whether or not modified by the term "about”, the claims include equivalents to the quantities.

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur des compositions qui sont des bis[(alkylamino)alkyl]amines aliphatiques représentées par la formule NH(RaNHRb)2 dans laquelle chaque Ra est, indépendamment, un groupe alkylène aliphatique et chaque Rb est, indépendamment, un groupe alkyle aliphatique comportant au moins trois atomes de carbone. L'invention porte également sur des procédés permettant de former des bis[(alkylamino)alkyl]amines aliphatiques.
PCT/US2009/035633 2009-03-02 2009-03-02 Bis[(alkylamino)alkyl]amines WO2010101560A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2009/035633 WO2010101560A1 (fr) 2009-03-02 2009-03-02 Bis[(alkylamino)alkyl]amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2009/035633 WO2010101560A1 (fr) 2009-03-02 2009-03-02 Bis[(alkylamino)alkyl]amines

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013049488A1 (fr) * 2011-09-30 2013-04-04 3M Innovative Properties Company Produits de marquage au sol souples
WO2013180740A1 (fr) * 2012-05-29 2013-12-05 3M Innovative Properties Company Compositions de marquage de chaussées
WO2016033115A1 (fr) * 2014-08-25 2016-03-03 Curza Global, Llc Procédé de production de n-alkyle polyamines
US11110428B2 (en) 2019-10-09 2021-09-07 Saudi Arabian Oil Company Hydrodearylation reactor

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008112636A1 (fr) * 2007-03-13 2008-09-18 Albemarle Corporation Allongeurs de chaîne

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008112636A1 (fr) * 2007-03-13 2008-09-18 Albemarle Corporation Allongeurs de chaîne

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GELBARD G ET AL: "Preparation of selectively N-alkylated diethylenetriamine derivatives", COMPTE RENDUS DES SEANCES DE L'ACADEMIE DES SCIENCES, SERIE C: SCIENCES CHIMIQUES, ELSEVIER FRANCE, EDITIONS SCIENTIFIQUES ET MEDICALES, vol. 262, 1 June 1966 (1966-06-01), pages 1587 - 1590, XP008091732, ISSN: 0567-6541 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013049488A1 (fr) * 2011-09-30 2013-04-04 3M Innovative Properties Company Produits de marquage au sol souples
CN103930497A (zh) * 2011-09-30 2014-07-16 3M创新有限公司 柔性道路标记
EP2760952A4 (fr) * 2011-09-30 2015-10-07 3M Innovative Properties Co Produits de marquage au sol souples
WO2013180740A1 (fr) * 2012-05-29 2013-12-05 3M Innovative Properties Company Compositions de marquage de chaussées
CN104334661A (zh) * 2012-05-29 2015-02-04 3M创新有限公司 道路标记组合物
US9797097B2 (en) 2012-05-29 2017-10-24 3M Innovative Properties Company Pavement marking compositions
WO2016033115A1 (fr) * 2014-08-25 2016-03-03 Curza Global, Llc Procédé de production de n-alkyle polyamines
CN107074734A (zh) * 2014-08-25 2017-08-18 库扎环球有限责任公司 制造n‑烷基多胺的方法
US11110428B2 (en) 2019-10-09 2021-09-07 Saudi Arabian Oil Company Hydrodearylation reactor

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