Low viscosity polyether carbonate polyols having side chains

Patent metadata

Field	Value
Publication number	US-9957353-B2
Application number	US-201414915668-A
Country	US
Kind code	B2
Filing date	Sep 1, 2014
Priority date	Sep 5, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

The present invention provides a method for producing low viscosity polyether carbonate polyols having side chains. A double metal cyanide catalyst and a suspension medium, with or without an H-functional starter compound, are initially introduced as a reaction mixture, and alkylene oxides are metered into the reaction mixture in two steps. The difference between the molecular weights of the lightest and the heaviest of the alkylene oxides metered in the two steps is greater than or equal to 24 g/mol, and the lightest alkylene oxide is a C2-C4 alkylene oxide. The alkylene oxides metered in the two steps can be the same or different. The invention also relates to the low viscosity polyether carbonate polyols produced by the method and to the use thereof.

First claim

The invention claimed is:

1. A process for preparing polyethercarbonate polyols having side chains, comprising the steps of:
(α) initially introducing a catalyst and (αα) a suspension medium which contains no H-functional groups and/or (αβ) a H-functional starter compound;
(β) metering in at least one alkylene oxide; and
(γ) metering in carbon dioxide and at least two alkylene oxides, wherein one or more of the alkylene oxides metered in step (γ) is a glycidyl ether, wherein the at least one alkylene oxide metered in step (β) is different than at least one of the at least two alkylene oxides metered in step (γ), and wherein at least one of the at least two alkylene oxides metered in step (γ) is different than another one of the at least two alkylene oxides metered in step (γ);
wherein the difference in the molecular weight of a lightest and a heaviest alkylene oxide metered in steps (β) and (γ) is greater than or equal to 24 g/mol, and the lightest alkylene oxide metered in steps (β) and (γ) is a C2-C4 alkylene oxide, wherein the C2-C4 alkylene oxide is ethylene oxide and/or propylene oxide, and the step (β) is carried out between step (α) and step (γ);
wherein the difference in the molecular weight of a lightest and heaviest alkylene oxides metered in step (γ) is greater than or equal to 24 g/mol, and the lightest alkylene oxide metered in step (γ) is a C2-C4 alkylene oxide, and when no H-functional starter compound is initially introduced in step (α), step (γ) further comprises metering in a H-functional starter compound;
wherein the molar ratio of a lightest to a heaviest alkylene oxide added in steps (β) and (γ) in total is greater than or equal to 5:1 and less than or equal to 1000:1; and
wherein the catalyst is a double metal cyanide catalyst, and wherein the glycidyl ether metered in step (γ) and is selected from the group consisting of allyl glycidyl ether, p-tert-butylphenyl glycidyl ether, 2-ethylhexyl glycidyl ether, glycidyl phenyl ether, methyl glycidyl ether, ethyl glycidyl ether, 2-ethyl hexyl glycidyl ether, allyl glycidyl ether, glycidyl methacrylate, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxypropyltripropoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropylethyldiethoxysilane, 3-glycidyloxypropyltriisopropoxysilane, and combinations of any thereof.

2. The process of claim 1 , wherein carbon dioxide is metered in step (β).

3. The process of claim 1 , wherein the temperature in reaction step (γ) is below the temperature of reaction step (β).

4. The process of claim 1 , wherein at least one of the alkylene oxides metered in stages (β) and/or (γ) comprises a C2-C15 alkyl or alkenyl group.

5. The process of claim 1 , wherein the process is carried out continuously.

6. The process of claim 1 , wherein a cyclic anhydride is added in steps (β) and/or (γ).

7. A polyethercarbonate polyol obtained by the process of claim 1 , wherein the viscosity of the polyethercarbonate polyol at 25° C. is less than or equal to 20,000 mPas and greater than or equal to 100 mPas, and wherein the fraction of the heaviest alkylene oxide incorporated into the polymer is ≥1 mol % and ≤20 mol %.

8. The polyethercarbonate polyol of claim 7 , wherein the ratio of the carbonate ester groups to ether groups of the polymer is ≥1:20 and ≤1:1.

9. The polyethercarbonate polyol of claim 7 , wherein the molecular weight Mn is ≥400 and ≤10,000,000 g/mol.

10. A method comprising utilizing the polyethercarbonate polyol of claim 7 as a crosslinkable component within a crosslinking reaction for producing thermoset or elastomeric networks.

11. The method of claim 10 , comprising reacting the polyethercarbonate polyol with di- and/or polyisocyanates.

12. An article comprising the polyethercarbonate polyol of claim 7 , wherein the article is selected from the group consisting of detergent or cleaning product formulation, plasticizer, drilling fluid, fuel additive, ionic and non-ionic surfactant, lubricant, process chemical for papermaking or textiles production, cosmetic formulation, and pore formers in the manufacture of ceramics.

Assignees

• Covestro Deutschland Ag

Inventors

• Müller Thomas E
• Gürtler Christoph
• Subhani Muhammad A
• Leitner Walter

Classifications

• C08G65/2663

  Metal cyanide catalysts, i.e. DMC's · CPC title

• C08G65/2603 Primary

  the other compounds containing oxygen · CPC title

• C08G18/72

  Polyisocyanates or polyisothiocyanates · CPC title

• C08G18/48

  Polyethers · CPC title

• C08G64/183

  containing polyether sequences · CPC title