Alkoxylates of s-vinylthioalkanols

Patent metadata

Field	Value
Publication number	US-2016264691-A1
Application number	US-201415032916-A
Country	US
Kind code	A1
Filing date	Oct 30, 2014
Priority date	Oct 30, 2013
Publication date	Sep 15, 2016
Grant date	—

Abstract

Unsaturated compounds of the general formula (I)

where
R 1 , R 2 , R 3 are the same or different and are each independently H, CH 3 , R 4 is a linear or branched C 1 -C 30 -alkylene, R 5 , R 6 are the same or different and are each independently, H, C 1 -C 20 -alkyl, C 3 -C 15 -cycloalkyl, aryl,
—CH 2 —O—C 1 -C 20 -alkyl, —CH 2 —O—C 2 -C 20 -alkenyl, where R 5 and R 6 may together form a C 3 -C 6 -alkylene,
R 7 , is the same or different and is independently, H, C 1 -C 4 -alkyl,

R 8 is C 1 -C 22 -alkyl, C 2 -C 22 -alkenyl, and
n is an integer from 2 to 200.

Mixtures and polymers comprising compounds of the general formula (I). A method for preparing polymers wherein a free-radical polymerization of monomers comprising unsaturated compounds of the general formula (I) is carried out. A process for preparing polymers comprising polymer-analogous reactions. The use of polymers comprising compounds (I) as cement additives, grinding aids in the production of cement, additives to hydraulic binders, concrete plasticizers, reactive plasticizers for preparing plastics, rubber or latex, associative thickeners and antioxidants, or for preparing polyether siloxanes. Mixtures comprising such polymers.

First claim

1 : An unsaturated compound of formula (I)

wherein
R 1 , R 2 , R 3 are the same or different and are each independently H, or CH 3 ,
R 4 is a linear or branched C 1 -C 30 -alkylene,
R 5 , R 6 are the same or different and are each independently, selected from the group consisting of H, C 1 -C 20 -alkyl, C 3 -C 15 -cycloalkyl, aryl, —CH 2 —O—C 1 -C 20 -alkyl, and CH 2 —O—C 2 -C 20 -alkenyl,
where R 5 and R 6 may together form a C 3 -C 6 -alkylene,
R 7 , is the same or different and is independently, H, C 1 -C 4 -alkyl, or

R 8 is C 1 -C 22 -alkyl, or C 2 -C 22 -alkenyl, and
n is an integer from 2 to 200.

2 : The unsaturated compound according to claim 1 , wherein
R 4 is a C 2 -C 4 -alkylene group, R 5 , R 6 are the same or different and are each independently a group selected from H, —CH 3 , —CH 2 —CH 3 , —C 3 -C 11 -alkyl, C 12 -C 22 -alkyl, phenyl, —CH 2 —O—C 1 -C 10 -alkyl, and CH 2 —O—C 2 -C 10 -alkenyl, R 7 is H or C 1 -C 4 -alkyl and n is 5 to 140.

3 : The unsaturated compound according to claim 1 , wherein the compound is an unsaturated compound (Ia):

wherein
R 3 is H or methyl,
R 4 is a linear or branched C 2 -C 10 -alkylene group,
R 5 , R 6 are each independently H, methyl or ethyl, with the proviso that the sum total of carbon atoms in the R 5 and R 6 residues per alkoxy group is in each case 0 to 2, and
n is 5 to 160.

4 : The unsaturated compound according to claim 1 , wherein the compound is an unsaturated compound (Ib):

wherein n is 20 to 140.

5 : The unsaturated compound according to claim 4 , wherein n is 20 to 30.

6 : A mixture comprising compounds of formula (I) according to claim 1 .

7 : A polymer comprising compounds of formula (I) according to claim 1 as monomers.

8 : A polymer comprising compounds of formula (Ia) according to claim 3 as monomers.

9 : A polymer comprising compounds of formula (Ib) according to claim 4 as monomers.

10 : The polymer according to claim 7 , wherein at least one further monomer different from the compounds of formula (I), (Ib) or (Ic) is present in the polymer.

11 : The polymer according to claim 10 , wherein the further monomers are at least one monoethylenically unsaturated monomer.

12 : The polymer according to claim 11 , wherein the monoethylenically unsaturated monomers are monomers comprising acid groups, where the acid groups may also be completely or partly neutralized.

13 : The polymer according to claim 12 , wherein the acid groups are groups selected from the groups of carboxylic acid groups, sulfonic acid groups, phosphoric acid groups or phosphonic acid groups.

14 : The polymer according to claim 13 , wherein the polymer comprises at least one monomer having carboxylic acid groups selected from the group of acrylic acid, methacrylic acid, (meth)acrylic anhydride, crotonic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, mesaconic acid, citraconic acid or methylene malonic acid and salts thereof.

15 : The polymer according to claim 13 , wherein the polymer comprises at least one monomer having phosphoric acid groups or phosphonic acid groups selected from the group consisting of vinylphosphonic acid, esters of hydroxyethyl, hydroxypropyl or hydroxybutyl (meth)acrylate with (poly)phosphoric acid, monovinyl phosphate, allylphosphonic acid, monoallyl phosphate, 3-butenylphosphonic acid, mono-3-butenyl phosphate, mono(4-vinyloxybutyl) phosphate, mono(2-hydroxy-3-vinyloxypropyl) phosphate, mono(1-phosphonoxymethyl-2-vinyloxyethyl) phosphate, mono(3-allyloxy-2-hydroxypropyl) phosphate, mono[2-(allyloxy-1-phosphonoxymethyl ethyl)]phosphate, 2-hydroxy-4-vinyloxymethyl-1,3,2-dioxaphosphole, 2-hydroxy-4-allyl oxymethyl-1,3,2-dioxaphosphole and salts thereof.

16 : The polymer according to claim 13 , wherein the polymer comprises at least one monomer having sulfonic acid groups selected from the group consisting of vinylsulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-acrylamidomethyldodecyl sulfonic acid, 2-(meth)acryloxyethanesulfonic acid, 3-(meth)acryloxypropanesulfonic acid, allyloxybenzenesulfonic acid, vinylbenzenesulfonic acid, vinyltoluenesulfonic acid, allylsulfonic acid, methallylsulfonic acid and salts thereof.

17 : The polymer according to claim 7 , wherein at least one monoethylenically unsaturated monomer present is styrene, butadiene, methyl methacrylate, (meth)acrylate, ethyl acrylate, dibutyl maleate, methyl alpha-cyanoacrylate, acrylonitrile, acrylic acid, methacrylic acid, maleic acid (anhydride), itaconic acid, vinylphosphonic acid, N-vinylpyrrolidone, N,N-dimethyl-N,N-diallylammonium chloride, acrylamide, vinylimidazole, vinyl alcohol, vinyl acetate, allylsulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, (iso)prenyl alkoxylate, (meth)allyl alkoxylate or hydroxybutyl vinyl ether alkoxylate.

18 : The polymer according to claim 17 , wherein at least one monoethylenically unsaturated monomer present is acrylic acid, methacrylic acid, (meth)acrylate, maleic acid (anhydride), (iso)prenyl alkoxylate, (meth)allyl alkoxylate or hydroxybutyl vinyl ether alkoxylate.

19 : The polymer according to claim 18 , wherein no other monomers are present besides unsaturated compounds of formula (I), acrylic acid, methacrylic acid, (meth)acrylate, maleic acid (anhydride), (iso)prenyl alkoxylate, (meth)allyl alkoxylate or hydroxybutyl vinyl ether alkoxylate.

20 : The polymer according to claim 17 , wherein no other monomers are present besides unsaturated compounds of formula (I) and acrylic acid and methacrylic acid or acrylic acid and maleic acid (anhydride) or methacrylic acid and maleic acid (anhydride).

21 : The polymer according to claim 20 , wherein no other monomers are present besides unsaturated compounds of formula (I), acrylic acid, methacrylic acid and maleic acid (anhydride).

22 : The polymer according to claim 7 , wherein from 5 to 99.9% by weight of unsaturated compounds of formula (I), (Ia) or (Ib) are present in the polymer, based on the total amount of monomers.

23 : The polymer according to claim 7 , wherein from 5 to 99.9% by weight of unsaturated compounds of formula (I) and from 95 to 0.1% by weight of further, monoethylenically unsaturated monomers are present, in each case based on the total amount of monomers.

24 : The polymer according to claim 18 , wherein from 5 to 99.9% by weight of unsaturated compounds of formula (I) and in total from 95 to 0.1% by weight of acrylic acid, methacrylic acid, (meth)acrylate, maleic acid (anhydride), (iso)prenyl alkoxylate, (meth)allyl alkoxylate or hydroxybutyl vinyl ether alkoxylate are present, in each case based on the total amount of monomers.

25 : The polymer according to claim 7 , wherein the number-average molecular weight M n of the polymers is 1000 g/mol to 1,000,000 g/mol.

26 : The polymer according to claim 7 , wherein the number-average molecular weight M n o

Assignees

• Basf Se

Inventors

• Maitro-Vogel Sophie
• Ernst Martin
• Schade Christian
• Tuzina Pavel
• Tran-Thien Hoang Trang
• Reis-Walther Eva-Maria
• Shabelina Natalia
• Hillesheim Nina Susanne
• Scholz Christian

Classifications

• C07C321/18 Primary

  of an acyclic unsaturated carbon skeleton · CPC title

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title

• C08F220/06 Primary

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08F28/04 Primary

  Thioethers · CPC title

• C04B24/32

  Polyethers, e.g. alkylphenol polyglycolether · CPC title