Block copolymers as soil release agents in laundry processes

Patent metadata

Field	Value
Publication number	US-9790452-B2
Application number	US-201414780045-A
Country	US
Kind code	B2
Filing date	Mar 17, 2014
Priority date	Mar 27, 2013
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

Described are block copolymers which have been prepared by controlled free radical polymerization. Also described is the use of said block copolymers as soil release agents in laundry processes and a process to produce said block copolymers. Further described is a method for easier releasing soil from textiles in laundry processes and a detergent containing said block copolymers.

First claim

What is claimed is:

1. A block copolymer obtained by a process comprising:
(a) polymerizing a C 1 -C 10 alkyl ester of acrylic or methacrylic acid with controlled free radical polymerization;
(b) polymerizing the polymer of (a) with controlled free radical polymerization with
(i) one or more monomers according to the following formula (I):

wherein R 1 is hydrogen or C 1-10 alkyl, R 2 is C 1-20 alkylene, and R 3 and R 4 are independently linear or branched C 1 -C 22 alkyl; or

(ii)one or more monomers according to the following formula (II):

wherein R 1 is hydrogen or C 1-10 alkyl, R 2 is C 1-20 alkylene, and R 3 and R 4 are independently linear or branched C 1 -C 22 alkyl; or

(iii) a mixture of monomers according to formula (I) and (II); and
(iv) optionally, with styrene or 4-Vinylpyridine,

to form a block copolymer;
(c) modifying the block copolymer of (b) in a polymer analogous transesterification reaction with a primary or secondary alcohol; and
(d) optionally, quaternizing of the block copolymer of (c);
wherein the block copolymer is effective as a soil release agent upon formulation of the block copolymer in a laundry detergent composition; and
the block copolymer has a quaternization degree of 20 to 80%.

2. The block copolymer of claim 1 , wherein the block copolymer has a polydispersity index PDI from 1.0 to 2.5.

3. The block copolymer of claim 1 , wherein the block copolymer has been prepared in (a) from n-butylacrylate.

4. The block copolymer of claim 1 , wherein the monomer of (b) is selected from the group consisting of dimethylaminopropyl methacrylate, dimethylaminopropyl acrylate, 2-(dimethylamino)ethyl methacrylate, 2-(dimethylamino)ethyl acrylate, dimethylaminopropyl acrylamide, dimethylaminopropyl methacrylamide, 2-(dimethylamino)ethyl acrylamide, and 2-(dimethylamino)ethyl methacrylamide.

5. The block copolymer of claim 1 , wherein the monomer of (a) is n-butylacrylate and wherein the monomer of (b) is 2-(dimethylamino)ethyl methacrylate or dimethylaminopropyl methacrylamide.

6. The block copolymer of claim 1 , wherein the primary or secondary alcohol in (c) is selected from the group consisting of:
(a) an ethoxylate of formula (A)
R A —[O—CH 2 —CH 2 —] n —OH  (A)

wherein R A is saturated or unsaturated, linear or branched chain alkyl with 1 to 22 carbon atoms, or alkylaryl or dialkylaryl with up to 24 carbon atoms, and n is 1 to 150;

(b) a polydimethylsilicone oligomer of formula (B)

wherein R B is C 1 -C 18 alkyl, phenyl or C 7 -C 15 aralkyl; n is 1 to 50 and R′ is a linking group with 1 to 20 carbon atoms;

(c) a partly or fully fluorinated primary alcohol; and
(d) a C 8 to C 60 alkyl linear or branched primary or secondary alcohol.

7. The block copolymer of claim 6 , wherein the primary or secondary alcohol is methoxy poly(ethylene glycol).

8. An aqueous laundry process comprising:
obtaining a laundry detergent composition comprising the block copolymer of claim 1 as a soil release agent and one or more detergent composition ingredients selected from the group consisting of: surfactants, builder substances, bleach components, brighteners, additives, enzymes, and dye-fixing agents; and
washing laundry with the laundry detergent composition.

9. A detergent comprising: the block copolymer of claim 1 as a soil release agent and one or more detergent composition ingredients selected from the group consisting of: surfactants, builder substances, bleach components, brighteners, additives, enzymes, and dye-fixing agents.

10. A block copolymer obtained by a process comprising:
(a) polymerizing a MPEG acrylate, siloxane acrylate, siloxane methacrylate, fluorinated acrylate, fluorinated methacrylate, C16/C18 alkyl acrylate with controlled free radical polymerization;
(b) polymerizing the polymer of (a) with controlled free radical polymerization with
(i) one or more monomers according to the following formula (I):

wherein R 1 is hydrogen or C 1-10 alkyl, R 2 is C 1-20 alkyl, and R 3 and R 4 are independently linear or branched C 1 -C 22 alkyl; or

(ii) one or more monomers according to the following formula (II):

wherein R 1 is hydrogen or C 1-10 alkyl, R 2 is C 1-20 alkyl, and R 3 and R 4 are independently linear or branched C 1 -C 22 alkyl; or
(iii) a mixture of monomers according to formula (I) and (II); and
(iv) optionally, with styrene or 4-vinylpyridine, to form a block copolymer; and

(c) optionally, quaternizing of the block copolymer of (b);

wherein the block copolymer is effective as a soil release agent upon formulation of the block copolymer in a laundry detergent; and
the block copolymer has a quaternization degree of 20 to 80%.

11. The block copolymer of claim 10 , wherein styrene or 4-vinylpyridine are present in the range of from 0 to 20 repeating units.

12. An aqueous laundry process comprising:
obtaining a laundry detergent composition comprising the block copolymer of claim 10 as a soil release agent and one or more detergent composition ingredients selected from the group consisting of: surfactants, builder substances, bleach components, brighteners, additives, enzymes, and dye-fixing agents; and
washing laundry with the laundry detergent composition.

13. A detergent comprising: the block copolymer of claim 10 as a soil release agent and one or more detergent composition ingredients selected from the group consisting of: surfactants, builder substances, bleach components, brighteners, additives, enzymes, and dye-fixing agents.

14. A process for preparing a laundry detergent composition comprising:
a) polymerizing a C 1 -C 10 alkyl ester of acrylic or methacrylic acid with controlled free radical polymerization;
b) polymerizing the polymer of (a) with controlled free radical polymerization with
(i) one or more monomers according to the following formula (I):

wherein R 1 is hydrogen or C 1-10 alkyl, R 2 is C 1-20 alkylene, and R 3 and R 4 are independently linear or branched C 1 -C 22 alkyl; or

(ii) one or more monomers according to the following formula (II):

wherein R 1 is hydrogen or C 1-10 alkyl, R 2 is C 1-20 alkylene, and R 3 and R 4 are independently linear or branched C 1 -C 22 alkyl; or

(iii) a mixture of monomers according to formula (I) and (II); and
(iv) optionally, with styrene or 4-vinylpyridine,

to form a block copolymer;
c

Assignees

• Basf Se
• Henkel Ag & Co Kgaa

Inventors

• Kou Huiguang
• Pirrung Frank
• Ettl Roland
• Vacano Bernhard Ulrich Von
• Perera-Diez Dario
• Barreleiro Paula
• Junkes Christa
• Zipfel Johannes
• Giesen Brigitte
• Bessler Cornelius
• Hutmacher Martina

Classifications

• C08F293/005

  using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent · CPC title

• C11D3/0036

  Soil deposition preventing compositions; Antiredeposition agents · CPC title

• C08F2438/02

  Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO] · CPC title

• C11D3/3769 Primary

  (Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines · CPC title