Use of urethane alcohols for preparation of polyether polyols

{
  "publication_number": "US9714216B2",
  "country": "US",
  "kind": "B2",
  "title": "Use of urethane alcohols for preparation of polyether polyols",
  "abstract": "The present invention relates to a process for preparing polyether polyols by addition of alkylene oxides onto H-functional starter substances, characterized in that at least one urethane alcohol of formula (II) where R 1 is linear or branched C 2 to C 24 -alkylene which may optionally be interrupted by heteroatoms such as O, S or N and may be substituted, R 2 is linear or branched C 2 to C 24 -alkylene which may optionally be interrupted by heteroatoms such as O, S or N and may be substituted, R is H, linear or branched C 1 to C 24 -alkyl, C 3 to C 24 -cycloalkyl, C 4 to C 24 -aryl, C 5 to C 24 -aralkyl, C 2 to C 24 -alkenyl, C 2 to C 24 -alkynyl, each of which may optionally be interrupted by heteroatoms such as O, S or N and/or each of which may be substituted by alkyl, aryl and/or hydroxyl, is used as H-functional starter compound. The invention further provides the polyether polyols containing a urethane group, the polyether polyols obtainable by the process according to the invention, for the use of the inventive polyether polyols for preparation of a polyurethane polymer, and the resulting polyurethane polymers.",
  "claims": [
    "1. A process for preparing polyether polyols comprising adding of alkylene oxides onto H-functional starter compounds, wherein at least one urethane alcohol of formula (II) where R 1 is linear or branched C 2 - to C 24 -alkylene which may optionally be interrupted by heteroatoms such as O, S or N and may be substituted, R 2 is linear or branched C 2 - to C 24 -alkylene which may optionally be interrupted by heteroatoms such as O, S or N and may be substituted, R 3 is H, linear or branched C 1 - to C 24 -alkyl, C 3 - to C 24 -cycloalkyl, C 4 - to C 24 -aryl, C 5 - to C 24 -aralkyl, C 2 - to C 24 -alkenyl, C 2 - to C 24 -alkynyl, each of which may optionally be interrupted by heteroatoms such as O, S or N and/or each of which may be substituted by alkyl, aryl and/or hydroxyl, is used as H-functional starter compound.",
    "2. The process as claimed in claim 1, wherein R 1 =CH 2 - CH 2 or CH 2 - CH(CH 3), R 2 =CH 2 - CH 2 or CH 2 - CH(CH 3), and R 3 =H.",
    "3. The process as claimed in claim 1, wherein the urethane alcohol is obtained by reacting propylene carbonate and/or ethylene carbonate with an alkanolamine of formula (III) HN(R 3) - R 2 - OH (III) where R 2 and R 3 are as defined in claim 1.",
    "4. The process as claimed in claim 3, wherein the urethane alcohol is obtained by reacting propylene carbonate and/or ethylene carbonate with at least one amine selected from the group consisting of ethanolamine, diethanolamine, (N-methyl)ethanolamine, isopropanolamine, diisopropanolamine and propanolamine.",
    "5. The process as claimed in claim 1, wherein the alkylene oxide is at least one alkylene oxide selected from the group consisting of ethylene oxide and propylene oxide.",
    "6. The process as claimed in claim 1, wherein the addition is effected in the presence of at least one DMC catalyst.",
    "7. The process as claimed in claim 6, wherein at least one urethane alcohol of the formula (II) and the double metal cyanide catalyst are first initially charged and then the alkylene oxide is added.",
    "8. The process as claimed in claim 1, wherein one or more urethane alcohols of the formula (II) are metered continuously into the reactor as H-functional starter substance(s) during the reaction.",
    "9. The process as claimed in claim 6, wherein an H-functional starter polyol S-I and the double metal cyanide catalyst are initially charged and then at least one urethane alcohol of the formula (II) is metered in continuously together with one or more alkylene oxides, wherein the H-functional starter polyol S-I has an OH number in the range from 3 mg KOH/g to 1000 mg KOH/g, and wherein the resulting reaction mixture is removed continuously from the reactor after a pre-selectable mean residence time.",
    "10. The process as claimed in claim 8, wherein DMC catalyst is additionally also metered continuously into the reactor and the resulting reaction mixture is removed continuously from the reactor.",
    "11. The process as claimed in claim 9, wherein the reaction mixture removed continuously from the reactor with a content of 0.05% by weight to 10% by weight of alkylene oxide is transferred into a postreactor in which, by way of a postreaction, the content of free alkylene oxide is reduced to less than 0.05% by weight in the reaction mixture.",
    "12. The process as claimed in claim 9, wherein the starter polyol S-I used is a polyether polyol containing a structural unit of the formula (IV) where R 1 is linear or branched C 2 - to C 24 -alkylene which may optionally be interrupted by heteroatoms such as O, S or N and may be substituted, R 2 is linear or branched C 2 - to C 24 -alkylene which may optionally be interrupted by heteroatoms such as O, S or N and may be substituted, or a polyether polyol obtained by adding of alkylene oxides onto H-functional starter compounds, wherein at least one urethane alcohol of formula (II) used as H-functional starter compounds."
  ],
  "description_excerpt": "The present invention relates to a process for preparing polyether polyols by addition of alkylene oxides onto H-functional starter compounds, characterized in that at least one urethane alcohol is used as H-functional starter compound. The invention further provides polyether polyols containing a urethane group, the polyether polyols obtainable by the process of the invention, the use of the polyether polyols of the invention for preparation of a polyurethane polymer, and the resulting polyurethane polymers.\n\nThe preparation of polyether carbonate polyols by catalytic reaction of alkylene oxides (epoxides) and carbon dioxide in the presence of H-functional starter substances (“starters”) has been the subject of intensive study for more than 40 years (e.g. Inoue et al., Copolymerization of Carbon Dioxide and Epoxide with Organometallic Compounds, Die Makromolekulare Chemie 130, 210-220, 1969). This reaction is shown in schematic form in scheme (I), where R is an organic radical such as alkyl, alkylaryl or aryl which may in each case also contain heteroatoms, for example O, S, Si, etc., and where e, f, g and b are each integers, and where the product shown here in scheme (I) for the polyether carbonate polyol should be understood as meaning merely that blocks having the structure shown may in principle be retained in the polyether carbonate polyol obtained but the sequence, number and length of the blocks and the OH functionality of the starter may vary and is not restricted to the polyether carbonate polyol shown in scheme (I).",
  "cpc": [
    "C07C 269/06",
    "C08G 18/5045",
    "C08G 18/711",
    "C08G 65/2603",
    "C08G 65/2606",
    "C08G 65/2615",
    "C08G 65/2618",
    "C08G 65/2663",
    "C08G 65/33344",
    "C08G 71/04"
  ],
  "ipc": [
    "C07C 269/06",
    "C08G 18/50",
    "C08G 18/71",
    "C08G 65/26",
    "C08G 65/333",
    "C08G 71/04"
  ],
  "assignees": [
    "Covestro Deutschland AG"
  ],
  "inventors": [
    "Jörg Hofmann",
    "Kai Laemmerhold",
    "Hartmut Nefzger",
    "Monika HEINZ",
    "Bert Klesczewski",
    "Klaus Lorenz"
  ],
  "filing_date": "2014-11-19",
  "publication_date": "2017-07-25",
  "grant_date": "2017-07-25",
  "priority_date": "2013-11-22",
  "application_number": "US-201415036486-A",
  "family_id": "49667003",
  "cited_by_count": 3,
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