Amphiphilic star-like polyether

Patent metadata

Field	Value
Publication number	US-10669380-B2
Application number	US-201515329158-A
Country	US
Kind code	B2
Filing date	Jul 22, 2015
Priority date	Jul 30, 2014
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

The present invention relates to amphiphilic star-like polyether. The core molecule is an aliphatic hyperbranched polyether polyol, which is further alkoxylated, first with ethylene oxide or combinations of ethylene oxide and C 3 -C 20 alkylene oxide, preferably propylene oxide, and/or glycidol, and then with a C 3 -C 20 alkylene oxide, preferably propylene oxide, or combination of ethylene oxide and propylene oxide, then optionally anionically modified. The resulting amphiphilic star-like polyether thus has an inner core based on an aliphatic hyperbranched polyether polyol, an inner shell predominantly containing polyethylene oxide units, the inner shell comprising at least 3 ethylene oxide units and an outer shell predominantly containing polypropylene oxide units, the outer shell comprising at least 3 propylene oxide units. They optionally contain anionic groups instead of hydroxyl groups on the periphery of the macromolecule. The invention further relates to their use as additive in laundry formulations and to their manufacturing process.

First claim

The invention claimed is:

1. An amphiphilic polyether obtainable by the process of:
i) step i: preparation of an aliphatic hyperbranched polyether polyol (core compound A) by one of
a) reacting an aliphatic alcohol α with the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 3≤x≤6, 0≤y≤20, 0≤z≤20, and 3≤n≤10 with a di-, tri-, tetra- or higher functional aliphatic alcohol β with the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 2≤x≤8, 0≤y≤20, 0≤z≤20, 2≤n≤10, in the presence of a catalyst, and removing the water formed during the reaction (polycondensation approach i)a)); and
b) reacting an aliphatic alcohol ω with the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 1≤x≤6, 0≤y≤20, 0≤z≤20 and 1≤n≤10 with at least one cyclic carbonate based on an aliphatic polyol with the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 3≤x≤6, 0≤y≤20, 0≤z≤20, and 3≤n≤10, in the presence of a base as catalyst, and removing the carbon dioxide formed during the reaction (ring-opening polycondensation approach i)b)); and

ii) step ii: reacting core compound A with ethylene oxide only, leading to compound B, and
iii) step iii: reacting compound B with a C 3 -C 20 alkylene oxide only, leading to compound C, and
iv) optionally, step iv: reacting compound C with a modifying reagent to convert 5 to 100% of the terminal hydroxyl groups to anionic sulphate, sulfonate, carboxylate, phosphate or phosphonate groups, leading to compound D.

2. The amphiphilic polyether according to claim 1 , wherein the aliphatic alcohol α or ω is selected from the group consisting of glycerol, trimethylolethane, trimethylolpropane, 1,2,4-butanetriol, 1,2,3-hexanetriol, 1,2,4-hexanetriol, pentaerythritol and dipentaerythritol.

3. The amphiphilic polyether according to claim 1 , wherein in the polycondensation approach i)a), the aliphatic alcohol α is pentaerythritol and pentaerythritol is reacted with at least one additional di-, tri-, tetra- or higher functional aliphatic alcohol β having the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 2≤x≤8, 0≤y≤20, 0≤z≤20, 2≤n≤10.

4. The amphiphilic polyether according to claim 1 , wherein the aliphatic alcohol ω is glycerol.

5. The amphiphilic polyether according to claim 1 , wherein in the polycondensation approach i)a), the additional di-, tri-, tetra- or higher functional aliphatic alcohol β is an ethoxylated ethylene glycol.

6. The amphiphilic polyether according to claim 1 , wherein in the polycondensation approach i)a), the additional di-, tri-, tetra- or higher functional aliphatic alcohol β is triethylene glycol.

7. The amphiphilic polyether according to claim 1 , wherein in the ring-opening polycondensation approach i) b), the cyclic carbonate based on an aliphatic polyol having the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 3≤x≤6, 0≤y≤20, 0≤z≤20 and 3≤n≤10 is glycerol carbonate.

8. The amphiphilic polyether according to claim 1 , wherein core compound A has an OH number of from 400 to 1000 mg KOH per g of polymer and a weight-average molecular weight (Mw) of from 2000 g/mol to 100000 g/mol.

9. The amphiphilic polyether according to claim 1 , wherein in step iii the C 3 -C 20 alkylene oxide is propylene oxide.

10. The amphiphilic polyether according to claim 1 , wherein in step ii, 1 mole of hydroxyl groups of core compound A is reacted with at least 3 moles ethylene oxide molecules, and in step iii 1 mole of hydroxyl groups of compound B is reacted with at least 3 moles propylene oxide molecules.

11. The amphiphilic polyether according to claim 1 , further comprising step iv wherein compound D contains terminal sulphate groups.

12. An additive for use in laundry detergents, the additive comprising the amphiphilic polyether according to claim 1 .

13. A dispersant for hydrophobic soil, the dispersant comprising the amphiphilic polyether according to claim 1 .

14. An agent for anti-redeposition or anti-greying, the agent comprising the amphiphilic polyether according to claim 1 .

15. Laundry compositions containing the amphiphilic polyether of claim 1 .

16. Liquid laundry compositions comprising water, 0.1-60 wt % surfactants, and 0.1-10 wt % amphiphilic polyether according to claim 1 .

17. A process for the manufacture of an amphiphilic polyether, the process comprising:
i) step i: preparing an aliphatic hyperbranched polyether polyol (core compound A) by one of:
a) reacting an aliphatic alcohol α having the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 3≤x≤6, 0≤y≤20, 0≤z≤20, and 3≤n≤10 with a di-, tri-, tetra- or higher functional aliphatic alcohol β having the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 2≤x≤8, 0≤y≤20, 0≤z≤20, 2≤n≤10, in the presence of a catalyst, and removing the water formed during the reaction (polycondensation approach i)a)); and
b) reacting an aliphatic alcohol ω having the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 1≤x≤6, 0≤y≤20, 0≤z≤20 and 1≤n≤10 with a cyclic carbonate based on an aliphatic polyol having the general formula [C n H (2n+2)−x OH x ][EO] y [PO] z , wherein 3≤x≤6, 0≤y≤20, 0≤z≤20, and 3≤n≤10, in the presence of a base as catalyst, and removing the carbon dioxide formed during the reaction (ring-opening polycondensation approach i)b)),

ii) step ii: reacting core compound A with ethylene oxide only, leading to compound B, and
iii) step iii: reacting compound B with a C 3 -C 20 alkylene oxide only, leading to compound C, and
iv) optionally, step iv: reacting compound C with a modifying reagent to convert 5 to 100% of the terminal hydroxyl groups to anionic sulphate, sulfonate, carboxylate, phosphate or phosphonate groups, leading to compound D.

Assignees

• Basf Se
• Henkel Ag & Co Kgaa

Inventors

• Tuerk Holger
• Reis-Walther Eva-Maria
• Maitro-Vogel Sophie
• Mueller-Cristadoro Anna
• Breffa Catherine
• Garcia Marcos Alejandra
• Crone Benedikt
• Job Mareile
• Gluesen Birgit
• Spill Iwona

Classifications

• C08G83/005 Primary

  Hyperbranched macromolecules · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title

• C08G83/002

  Dendritic macromolecules · CPC title

• C08G65/2606 Primary

  containing hydroxyl groups · CPC title

• C11D11/0017

  Chemistry & Metallurgy · mapped topic