Surfactants with lower CMC, and surfactant systems and detergents containing said surfactants

Patent metadata

Field	Value
Publication number	US-9593295-B2
Application number	US-201514813565-A
Country	US
Kind code	B2
Filing date	Jul 30, 2015
Priority date	Feb 1, 2013
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

The invention relates to surfactants of the formula (I), in which R 1 stands for —H or —CH 3 ; R 2 , R 3 , R 4 , R 5 , R 6 independently stand for —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —OH, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH(CH 3 ) 2 , a linear or branched alkyl group containing 8 to 20 C atoms, or —SO 3 − X + ; X + stands for a monovalent cation or the nth part of an n-valent cation; exactly one radical R 2 , R 3 , R 4 , R 5 , R 6 stands for —SO 3 − X + ; and exactly one radical R 2 , R 3 , R 4 , R 5 , R 6 stands for a linear or branched alkyl radical containing 8 to 20 C atoms.

First claim

What is claimed is:

1. Surfactants of formula (I)

in which
R 1 stands for —CH 3 ,
R 2 , R 3 , R 4 , R 5 , R 6 independently stand for —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —OH, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH(CH 3 ) 2 , a linear or branched alkyl radical containing 8 to 20 C atoms, or —SO 3 − X + ,
X + stands for a monovalent cation or the nth part of an n-valent cation,
with the condition that
exactly one radical R 2 , R 3 , R 4 , R 5 , R 6 stands for —SO 3 − X + and
exactly one radical R 2 , R 3 , R 4 , R 5 , R 6 stands for a linear or branched alkyl radical containing 8 to 20 C atoms.

2. Surfactants according to claim 1 , characterized in that they have a CMC of less than 0.1 g/L.

3. Surfactants according to claim 1 , characterized in that they have an interfacial tension of less than 2 mN/m.

4. Surfactants according to claim 1 , characterized in that they have a CMC of 0.01 to 0.06 g/L and at the same time produce an interfacial tension of 1.6 mN/m maximum.

5. Surfactants according to claim 1 , characterized in that the surfactant(s) is/are selected from surfactants of formulas (la) and/or (Ib) and/or (Ic) and/or (Id)

in which
R 1 stands for —CH 3 ,
R 3 , R 4 , R 5 , R 6 independently stand for —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —OH, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH(CH 3 ) 2 ,
n, m independently stand for integers from 0 to 18, with the condition that the sum (m+n) stands for one of the numbers 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18.

6. Surfactants according to claim 1 , characterized in that the surfactant(s) is/are selected from surfactants of formulas (Ie) and/or (If) and/or (Ig) and/or (Ih)

in which
R 1 stands for —CH 3 ,
R 2 , R 4 , R 5 , R 6 independently stand for —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —OH, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH(CH 3 ) 2 ,
n, m independently stand for integers from 0 to 18, with the condition that the sum (m+n) stands for one of the numbers 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18.

7. Surfactants according to claim 1 , characterized in that the surfactant(s) is/are selected from surfactants of formulas (Ii) and/or (Ij) and/or (Ik) and/or (Im)

in which
R 1 stands for —CH 3 ,
R 2 , R 3 , R 5 , R 6 independently stand for —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —OH, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 CH 3 , —OCH(CH 3 ) 2 ,
n, m independently stand for integers from 0 to 18, with the condition that the sum (m+n) stands for one of the numbers 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18.

8. Surfactant mixture comprising
a) at least one surfactant according to claim 1 and
b) at least one further surfactant.

9. Surfactant mixture according to claim 8 , comprising, based on the total quantity of all surfactants, 5 to 75% by weight, of surfactant(s) of formula
R 7 —O-(AO) m —H,

in which
R 7 stands for a linear or branched, substituted or unsubstituted alkyl, aryl, or alkylaryl radical,
AO stands for an ethylene oxide (EO) or propylene oxide (PO) group,
m stands for integers from 1 to 50.

10. Surfactant mixture according to claim 8 , comprising, based on the total quantity of all surfactants, 5 to 75% by weight, of surfactant(s) of formula
R 8 —O-(AO) n —SO 3 − Y + ,

in which
R 8 stands for a linear or branched, substituted or unsubstituted alkyl, aryl, or alkylaryl radical,
AO stands for an ethylene oxide (EO) or propylene oxide (PO) group,
n stands for integers from 0 to 50,
Y + stands for a monovalent cation or the nth part of an n-valent cation.

11. Surfactant mixture according to claim 8 , comprising, 1 to 90% by weight, of water.

12. Detergent or cleaning agent containing at least one surfactant according to claim 1 .

13. Detergent or cleaning agent according to claim 12 , characterized in that it is liquid and comprises, 1 to 90% by weight, of water.

14. Surfactant mixture according to claim 5 , comprising, 1 to 99% by weight, of at least one surfactant selected from the group consisting of formula (Ia), (Ib), (Ic), (Id).

15. Surfactant mixture according to claim 6 , comprising, 1 to 99% by weight, of at least one surfactant selected from the group consisting of formula (Ie), (If), (Ig), (Ih).

16. Surfactant mixture according to claim 7 , comprising, 1 to 99% by weight, of at least one surfactant selected from the group consisting of formula (Ii), (Ij), (Ik) and (Im).

Assignees

• Henkel Ag & Co Kgaa
• Studiengesellschaft Kohle Mbh
• Henkel Ag & Co Kgaa & Studiengesellschaft
• Kohle mbH

Inventors

• Kropf Christian
• Bode Nicole
• Bedrunka Danuta
• Rinaldi Roberto
• Estevez Rivera Hebert Jesus

Classifications

• C11D1/37

  Mixtures of compounds all of which are anionic · CPC title

• C11D1/831

  of sulfonates with ethers of polyoxyalkylenes without phosphates · CPC title

• C11D1/29

  Sulfates of polyoxyalkylene ethers · CPC title

• C11D1/83

  Mixtures of non-ionic with anionic compounds · CPC title

• C07C309/42 Primary

  having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings · CPC title