IP Library Granted Patent US 8,445,024
Granted Patent B2
US 8,445,024 · App. 12/081,711 · Granted May 21, 2013

Preparations containing hyperbranched polymers

Inventors: Matthias Seiler (Griesheim, DE); Axel Kobus (Langen, DE)
Assignee: Evonik Degussa GmbH
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Quick Facts
Patent No.
US 8,445,024
App. No.
12/081,711
Granted
May 21, 2013
Kind
B2
Abstract

The present invention relates to preparations comprising at least one low molecular weight substance and at least one hyperbranched polymer, wherein the hyperbranched polymer comprises a hydrophilic core having polyester units and hydrophobic end groups, said hyperbranched polymer having a molecular weight greater than or equal to 6000 g/mol and a hydroxyl number in the range from 0 to 200 mg KOH/g, the degree of branching being in the range from 20 to 70%, and said hyperbranched polymer having a melting point of at least 30° C.

Claims (43)

1. A preparation comprising at least one low molecular weight substance having a molar mass of from 15 g/mol to 1000 g/mol and at least one hyperbranched polymer, wherein said hyperbranched polymer comprises:

a) a hydrophilic core having polyester units and hydrophobic end groups;

b) a molecular weight greater than or equal to 6000 g/mol and a hydroxyl number in the range of from 0 to 200 mg KOH/g;

c) a degree of branching in the range of from 20 to 70%; and

d) a melting point of at least 30° C.;

and wherein said preparation is in the form of particles having a size in the range of from 1 to 1000 μm and in which said low molecular substance is embedded in a shell which comprises said hyperbranched polymer, said preparation being made by a process comprising:

(i) preparing a polymer melt comprising at least one hyperbranched polymer and at least one low molecular weight substance;

(ii) introducing said polymer melt into a second liquid phase in which said hyperbranched polymer is sparingly soluble and which has a solidification temperature below the solidification temperature of said hyperbranched polymer, said second liquid phase comprising 60 to 100% by weight of water, alcohols having up to 4 carbon atoms or combinations thereof;

(iii) dispersing said polymer melt in said second liquid phase at a temperature which is greater than or equal to the solidification temperature of said hyperbranched polymer; and

(iv) solidifying said polymer melt dispersed in said second liquid phase.

2. The preparation of claim 1 , wherein said hyperbranched polymer has a degree of functionalization of at least 30% and a water solubility by the flask method at 40° C. of at most 10% by mass.

3. The preparation of claim 1 , wherein said hydrophilic core has at least 90% by weight of repeat units derived from polyester-forming monomers.

4. The preparation of claim 1 , wherein said hydrophilic core comprises a central unit derived from an initiator molecule having at least two hydroxyl groups, and repeat units derived from monomers having at least one carboxyl group and at least two hydroxyl groups.

5. The preparation of claim 4 , wherein said initiator molecule is selected from the group consisting of: an aliphatic polyol; ditrimethylolpropane;

ditrimethylolethane; dipentaerythritol; pentaerythritol; alkoxylated pentaerythritol;

trimethylolethane; trimethylolpropane; alkoxylated trimethylolpropane; glycerol;

neopentyl alcohol; dimethylolpropane; and 1,3-dioxane-5,5-dimethanol.

6. The preparation of claim 4 , wherein said monomers are selected from the group consisting of: dimethylpropionic acid; α,α-bis(hydroxymethyl)-butyric acid; α,α,α-tris-(hydroxymethyl)acetic acid; α,α-bis(hydroxymethyl)valeric acid; α,α-bis(hydroxy)-propionic acid; and 3,5-dihydroxybenzoic acid.

7. The preparation of claim 1 , wherein said hydrophobic end groups are formed by groups derived from carboxylic acids selected from the group consisting of: decanoic acid; dodecanoic acid; tetradecanoic acid; hexadecanoic acid;

heptadecanoic acid; octadecanoic acid; eicosanoic acid; docosanoic acid and tetracosanoic acid.

8. The preparation of claim 1 , wherein said hyperbranched polymer has an acid number in the range of from 0 to 20 mg KOH/g or a melting point of at most 57° C.

9. The preparation of claim 1 , wherein said hydrophilic core has a hydroxyl number, measured before the hydrophobization, in the range from 400 to 600 mg KOH/g.

10. The preparation of claim 1 , wherein said low molecular weight substance is selected from the group consisting of: a compound having a peroxide group;

an amino acid; a catalyst; a dye or pigment; a vitamin; a monomer; flavoring or aroma enhancing agent; a medicament; an enzyme; a coenzyme; a plant extract; an initiator; a silicone; a surfactant; a silica; a silane; a solvent; a filler; a reactive crosslinker; a detergent; a hair dye; and a concrete additive.

11. The preparation of claim 1 , wherein said hyperbranched polymer is enzymatically degradable.

12. The preparation of claim 1 , wherein said preparation is in the form of particles with a size in the range of from 1 μm to 1000 μm and at least 80% by weight of said particles are within a size range of from 1 μm to 100 μm.

13. The preparation of claim 1 , wherein said hyperbranched polymer, at 48° C. in a 50% by weight/50% by weight mixture with water, has only liquid-liquid equilibria, but no solid-liquid equilibria, solid-liquid-liquid equilibria.

14. The preparation of claim 1 , wherein said preparation is part of a product selected from the group consisting of: a hardener; a crosslinker; a catalyst; a defoamer; a dispersant; an additive with antimicrobial or antifungicidal action; an additive for increasing the scratch resistance of surfaces; an additive in coatings or adhesives; a flow improver; a concrete additive; a cosmetic; a medicament; a deodorant; a food; an animal feed; a beverage; a wall or floor covering; a joint material; and a packaging or in paint system.

15. A process for producing a preparation comprising a low molecular weight substance embedded in a shell comprising a hyperbranched polymer, said process comprising the steps of:

(a) preparing a polymer melt comprising at least one hyperbranched polymer and a low molecular weight substance having a molar mass of from 15 g/mol to 1000 g/mol wherein said hyperbranched polymer comprises;

i) a hydrophilic core having polyester units and hydrophobic end groups;

ii) a molecular weight greater than or equal to 6000 g/mol and a hydroxyl number in the range of from 0 to 200 mg KOH/g;

iii) a degree of branching in the range of from 20 to 70%; and

iv) a melting point of at least 30° C.;

(b) introducing said polymer melt into a second liquid phase in which said hyperbranched polymer is sparingly soluble and which has a solidification temperature below the solidification temperature of said hyperbranched polymer, said second liquid phase comprising 60 to 100% by weight of water, alcohols having up to 4 carbon atoms or combinations thereof;

(c) dispersing said polymer melt in said second liquid phase at a temperature which is greater than or equal to the solidification temperature of said hyperbranched polymer; and

(d) solidifying said polymer melt dispersed in said second liquid phase.

16. The process of claim 15 , wherein said hydrophilic core has at least 90% by weight of repeat units derived from polyester-forming monomers.

17. The process of claim 15 , wherein said hyperbranched polymer has a degree of functionalization of at least 30% and a water solubility by the flask method at 40° C. of at most 10% by mass.

18. The process of claim 15 , wherein said hydrophobic end groups are formed by groups derived from carboxylic acids selected from the group consisting of: decanoic acid; dodecanoic acid; tetradecanoic acid; hexadecanoic acid; heptadecanoic acid; octadecanoic acid; eicosanoic acid; docosanoic acid and tetracosanoic acid.

19. The process of claim 15 , wherein said low molecular weight substance is selected from the group consisting of: a compound having a peroxide group;

an amino acid; a catalyst; a dye or pigment; a vitamin; a monomer; flavoring or aroma enhancing agent; a medicament; an enzyme; a coenzyme; a plant extract; an initiator; a silicone; a surfactant; a silica; a silane; a solvent; a filler; a reactive crosslinker; a detergent; a hair dye; and a concrete additive.

20. The preparation of claim 15 , wherein said preparation is in the form of particles with a size in the range of from 1 μm to 1000 μm and at least 80% by weight of said particles are within a size range of from 1 μm to 100 μm.

Assignments (2)
CHANGE OF NAME Recorded Feb 1, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051776/0230 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 21, 2008
From: SEILER, MATTHIAS; KOBUS, AXEL
To: EVONIK DEGUSSA GMBH
Reel/Frame 021560/0762 →
Priority Claims (2)
DE 10 2005 051 334 · Oct 25, 2005 · national
DE 10 2006 040 123 · Aug 26, 2006 · national
Continuity (1)
Related Publication 20080207871A1 · Aug 28, 2008