Alkyl sulfate ester or salt of same

Patent metadata

Field	Value
Publication number	US-11999681-B2
Application number	US-201816498576-A
Country	US
Kind code	B2
Filing date	Mar 30, 2018
Priority date	Mar 31, 2017
Publication date	Jun 4, 2024
Grant date	Jun 4, 2024

Abstract

An alkyl sulfate ester containing a carbonyl group or a salt thereof. The compound is represented by the following formula:

R 1 —C(—O)—(CR 2 2 ) n —(OR 3 ) p —(CR 4 2 ) q -L-OSO 3 X

wherein R 1 , R 2 , R 3 , R 4 , L, X, n, p and q are as defined herein. Also disclosed is a production method for making the alkyl sulfate ester.

First claim

The invention claimed is:

1. A compound represented by the following formula:

wherein
R 1 is a methyl group;
R 2 is H and R 4 is H or a substituent;
R 3 is a C1-C10 alkylene group optionally containing a substituent;
n is an integer of 1 or greater;
p and q are each individually an integer of 0 or greater;
X is H, a metal atom, NR 5 4 , imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R 5 s are each H or an organic group and are the same as or different from each other;
L is a single bond, —CO 2 —B—*, —OCO—B—*, —CONR 6 —B—*, —NR 6 CO—B—*, or —CO—, where B is a single bond or a C1-C10 alkylene group optionally containing a substituent, R 6 is H or a C1-C4 alkyl group optionally containing a substituent, and * indicates the bond to —OSO 3 X in the formula;
a total number of carbon atoms in the compound is 5 to 30; and
the compound excludes 11-keto dodecyl sulphate.

2. The compound according to claim 1 ,
wherein L is a single bond.

3. The compound according to claim 1 ,
wherein R 4 is H or a C1-C4 linear or branched alkyl group.

4. The compound according to claim 1 ,
wherein R 3 is a C1-C4 alkylene group free from a substituent.

5. The compound according to claim 1 ,
wherein X in the formula is a metal atom or NR 5 4 .

6. The compound according to claim 1 ,
wherein the compound is an aqueous dispersant.

7. A production method for producing the compound of claim 1 , the method comprising:
a step of oxidizing a compound represented by the following formula (10):
R 11 —CH═CH—(CR 2 2 ) n —(OR 3 ) p —(CR 4 2 ) q -L-OH  (10)

wherein
R 2 is H and R 4 is H or a substituent;
R 3 is a C1-C10 alkylene group optionally containing a substituent;
n is an integer of 1 or greater;
p and q are each individually an integer of 0 or greater;
R 11 is H; and
L is a single bond, —CO 2 —B—*, —OCO—B—*, —CONR 6 —B—*, —NR 6 CO—B—*, or —CO—, where B is a single bond or a C1-C10 alkylene group optionally containing a substituent, R 6 is H or a C1-C4 alkyl group optionally containing a substituent, and * indicates the bond to —OH in the formula (10),
to provide a compound represented by the following formula (41):

wherein R 2 to R 4 , R 11 , L, n, p, and q are defined as described above in formula (10); and
a step of sulfuric-esterifying the compound represented by formula (41) to provide a compound represented by the following formula (42):

wherein X is H, a metal atom, NR 5 4 , imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R 5 s are each H or an organic group and are the same as or different from each other; and
wherein R 2 to R 4 , R 11 , L, n, p, and q are defined as described above in formula (10).

8. The production method according to claim 7 ,
wherein L is a single bond.

Assignees

• Daikin Ind Ltd

Inventors

• Yoneda Satoru
• Higashi Masahiro
• Yamauchi Akiyoshi
• Ishihara Sumi
• Kishikawa Yosuke
• Nakano Marina
• Nitta Shinnosuke
• Aoyama Hirokazu

Classifications

• C07C305/10 Primary

  being further substituted by singly-bound oxygen atoms · CPC title

• C07C303/24

  of esters of sulfuric acids · CPC title

• C11D1/146 Primary

  Sulfuric acid esters · CPC title