Patent EP0763555A2 successfully refreshed from Google Patents.
← Back to Patent Explorer
EP0763555A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Alkylene oxide polymerisation catalysts

Assignee: Mitsui Chemicals Inc
•
Filing: 1996-09-09
•
Granted: —
•
Expires: 2016-09-09
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract A catalyst for the polymerization of an alkylene oxide compound is composed of a phosphazene compound or a phosphazenium salt which is derived from the phosphazene compound and an active hydrogen compound. A poly(alkylene oxide) can be efficiently produced by polymerizing the alkylene oxide compound in the presence of the catalyst and, when the catalyst is composed of the phosphazene compound, the active hydrogen compound. The poly(alkylene oxide) contains no residual metal components and compared with those produced using conventional amine-base catalysts, has also significantly improved odor.

Inventors

  • 👤 Masahiro Kouno
  • 👤 Kazumi Mizutani
  • 👤 Tadahito Nobori
  • 👤 Usaji Takaki

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 08:52
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/26; C08G65/2642; C08G65/2669; C08G65/2675

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 136 words
A process for the production of a polyalkylene oxide, which comprises reacting an alkylene oxide compound in the presence of an active hydrogen compound and a phosphazene compound represented by the following partial structural formula (1): wherein Q represents a hydrocarbon group having 1 to 20 carbon atoms, or in the presence of a phosphazenium salt of said active hydrogen compound, said phosphazenium salt having been derived from said active hydrogen compound and said phosphazene compound and being represented by the following partial structural formula (2): wherein Q represents a hydrocarbon group having 1 to 20 carbon atoms, x represents a number of phosphazenium cations, and Z X- represents an x-valent anion of said active hydrogen compound; and by way of example said alkylene oxide compound is ethylene oxide, propylene oxide, 1,2-butylene oxide or styrene oxide.
Claim 2
Dependent Claim 121 words
The process of claim 1. wherein said active hydrogen compound is water, a saturated or unsaturated, monohydric alcohol having 1 to 20 carbon atoms, a polyhydric alcohol having 2 to 10 hydroxyl groups and 2 to 20 carbon atoms, an aromatic compound having 1 to 2 hydroxyl groups and 6 to 20 carbon atoms, a carboxylic acid having 1 to 6 carbon atoms, a saccharide or a derivative thereof, an oligoalkylene oxide, or a poly(alkylene oxide), and for example said active hydrogen compound is selected from water; methanol; ethanol; phenol; 2-naphthol; acetic acid; propionic acid; ethylene glycol; propylene glycol; glycerin; pentaerythritol; sorbitol; dextrose; sucrose; or poly(ethylene glycol), poly(propylene glycol) or a copolymer thereof, whose molecular weight ranges from 90 to 10,000.
Claim 3
Dependent Claim 306 words
The process of claim 1 or claim 2, wherein said phosphazene compound is a compound represented by the following chemical formula (3): wherein ℓ, m and n individually represent 0 or a positive integer of 3 or smaller, Ds may be the same or different and individually represent a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group, a phenoxy group, a thiol residual group, a thiophenol residual group, a mono-substituted amino group, a di-substituted amino group or a 5- or 6-membered cyclic amino group, Q represents a hydrocarbon group having 1 to 20 carbon atoms, and two Ds on the same phosphorus atom or different phosphorus atoms may be linked together or D and Q may be linked together to form a ring structure; and said phosphazenium salt of said active hydrogen compound is a salt represented by the following chemical formula (4): wherein ℓ, m and n individually represent 0 or a positive integer of 3 or smaller, Ds may be the same or different and individually represent a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group, a phenoxy group, a thiol residual group, a thiophenol residual group, a mono-substituted amino group, a di-substituted amino group or a 5- or 6-membered cyclic amino group, Q represents a hydrocarbon group having 1 to 20 carbon atoms, two Ds on the same phosphorus atom or different phosphorus atoms may be linked together or D and Q may be linked together to form a ring structure, x represents a number of phosphazenium cations, and Z X- represents an x-valent anion of said active hydrogen compound, and for example ℓ, m and n in each of the chemical formula (3) and the chemical formula (4) are, irrespective of the order thereof, values of a combination selected from (2,1,1), (1,1,1), (1,1,0), (1,0,0) or (0,0,0).
Claim 4
Dependent Claim 91 words
The process of claim 3, wherein Ds in each of the chemical formula (3) and the chemical formula (4) are the same or different and are selected from the group consisting of hydrocarbon groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, phenoxy groups having 6 to 20 carbon atoms, mono-substituted amino groups having 1 to 20 carbon atoms, amino groups di-substituted by hydrocarbon groups which have 1 to 20 carbon atoms and are the same or different, and 5- or 6-membered cyclic amino groups.
Claim 5
Dependent Claim 58 words
The process of claim 3, wherein Ds in each of the chemical formula (3) and the chemical formula (4) are the same or different and are selected from the group consisting of amino groups di-substituted with alkyl groups, which are the same or different and have 1 to 6 carbon atoms, and 5- or 6-membered cyclic amino groups.
Claim 6
Dependent Claim 31 words
The process of claim 3, wherein Ds in each of the chemical formula (3) and the chemical formula (4) are selected from the group consisting of dimethylamino, methylethylamino and diethylamino groups.
Claim 7
Dependent Claim 59 words
The process of any one of claims 1 to 9, wherein each Q in each of the partial structural formula (1), partial structural formula (2), chemical formula (3) and chemical formula (4) is a hydrocarbon group selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, tert-octyl, nonyl and decyl.
Claim 8
Dependent Claim 94 words
The process of any one of claims 3 to 7, wherein, when two Ds on the same phosphorus atom or different phosphorus atoms are linked together to form a ring structure in each of the chemical formula (3) and the chemical formula (4), a divalent group (D-D) so formed on the same phosphorus atom or the different phosphorus atoms is a divalent group selected from the group consisting of ethylenediamino, trimethylenediamino and tetramethylene diamino groups, the two nitrogen atoms of each of said groups having been substituted individually by a methyl or ethyl group.
Claim 9
Dependent Claim 82 words
The process of any one of claims 3 to 8, wherein, when D and Q are linked together to form a ring structure in each of the chemical formula (3) and the chemical formula (4), a so-formed divalent group (D-Q) connecting the associated nitrogen atom and the associated phosphorus atom is a divalent group selected from the group consisting of aminomethylene, aminoethylene and aminotrimethylene groups, the nitrogen atom of each of said groups having been substituted by a methyl or ethyl group.
Claim 10
Dependent Claim 61 words
The process of claim 1 or claim 2, wherein said phosphazene compound is selected from 1-tert-butyl-2,2,2-tris(dimethylamino)phosphazene, 1-(1,1,3,3-tetramethylbutyl)-2,2,2-tris(dimethylamino)-phosphazene, 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ 5 ,4λ 5 -catenadi(phosphazene), 1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)-phosphoranilideneamino]-2λ 5 ,4λ 5 -catenadi(phosphazene), 1-(1,1,3,3-tetramethylbutyl)-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phosphoranilideneamino]-2λ 5 ,4λ 5 -catenadi(phosphazene), 1-tert-butyl-2,2,2-tri(1-pyrrolidinyl)phosphazene, or 7-ethyl-5,11-dimethyl-1,5,7,11-tetraaza-6λ 5 -phosphaspiro[5.5]undeca-1(6)-ene; and said phosphazenium salt of said active hydrogen compound is a phosphazenium salt derived from said active hydrogen compound and the thus-selected phosphazene compound.
Claim 11
Dependent Claim 67 words
The process of any one of claims 1 to 10, wherein two or more kinds of alkylene oxide compounds are successively polymerized to produce a block copolymer which contains blocks of said two or more kinds of alkylene oxide compounds, and for example as alkylene oxides, propylene oxide and ethylene oxide are successively polymerized to produce a block copolymer which contains poly(propylene oxide) and poly(ethylene oxide) blocks.
Claim 12
Dependent Claim 16 words
A poly(alkylene oxide) obtainable by the production process of any one of claims 1 to 11.
Claim 13
Dependent Claim 42 words
A catalyst useful for the production of a poly(alkylene oxide) by polymerization of an alkylene oxide compound, which comprises a phosphazene compound represented by the following partial structural formula (1): wherein Q represents a hydrocarbon group having 1 to 20 carbon atoms.
Claim 14
Dependent Claim 70 words
A catalyst useful for the production of a poly(alkylene oxide) by polymerization of an alkylene oxide compound, which comprises a phosphazenium salt of an active hydrogen compound, said phosphazenium salt being represented by the following partial structural formula (2): wherein Q represents a hydrocarbon group having 1 to 20 carbon atoms, x represents a number of phosphazenium cations, and Z X- represents an x-valent anion of said active hydrogen compound.
Claim 15
Dependent Claim 134 words
A catalyst useful for the production of a poly(alkylene oxide) by polymerization of an alkylene oxide compound, which comprises a phosphazene compound represented by the following chemical formula (3): wherein ℓ, m and n individually represent 0 or a positive integer of 3 or smaller, Ds may be the same or different and individually represent a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group, a phenoxy group, a thiol residual group, a thiophenol residual group, a mono-substituted amino group, a di-substituted amino group or a 5- or 6-membered cyclic amino group, Q represents a hydrocarbon group having 1 to 20 carbon atoms, and two Ds on the same phosphorus atom or different phosphorus atoms may be linked together or D and Q may be linked together to form a ring structure.
Claim 16
Dependent Claim 161 words
A catalyst useful for the production of a poly(alkylene oxide) by polymerization of an alkylene oxide compound, which comprises a phosphazenium salt of an active hydrogen compound, said phosphazenium salt being represented by the following chemical formula (4): wherein ℓ, m and n individually represent 0 or a positive integer of 3 or smaller, Ds may be the same or different and individually represent a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group, a phenoxy group, a thiol residual group, a thiophenol residual group, a mono-substituted amino group, a di-substituted amino group or a 5- or 6-membered cyclic amino group, Q represents a hydrocarbon group having 1 to 20 carbon atoms, two Ds on the same phosphorus atom or different phosphorus atoms may be linked together or D and Q may be linked together to form a ring structure, x represents a number of phosphazenium cations, and Z X- represents an x-valent anion of said active hydrogen compound.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Maintenance schedule is calculated for granted US utility patents.

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag