IP Library Granted Patent US 12,466,906
Granted Patent B2
US 12,466,906 · App. 17/664,986 · Granted Nov 11, 2025

Defoamer composition based on organofunctionally modified polybutadienes

Inventors: Philippe Favresse (Ratingen, DE); Alexander Schulz (Troisdorf, DE); Michael Fiedel (Essen, DE); Sarah Otto (Essen, DE); Frank Schubert (Neukirchen-Vluyn, DE); Thorsten Schierle (Essen, DE); Heike Semmler (Rheinberg, DE); Andreas Stüttgen (Hattingen, DE)
Assignee: Evonik Operations GmbH
C08F36/06C09D11/106C08F2810/00
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Quick Facts
Patent No.
US 12,466,906
App. No.
17/664,986
Granted
Nov 11, 2025
Kind
B2
Abstract

A defoamer composition contains a compound based on polybutadiene having at least one repeat unit selected from the divalent radicals:

Claims (34)

1 . A defoamer composition, comprising:

a compound based on polybutadiene having at least one repeat unit selected from the group consisting of divalent radicals

wherein

A is in each case independently a monovalent organic radical;

B is in each case independently a radical of the formula (4a)

R 1 is in each case independently a monovalent hydrocarbon radical having 1 to 16 carbon atoms;

R 2 is a radical of the formula ˜CH 2 —O—R 3 ;

R 3 is in each case independently a monovalent hydrocarbon radical having 3 to 18 carbon atoms;

R 4 is in each case independently a monovalent organic radical having 1 to 18 carbon atoms or hydrogen;

m, n, o, p and q are each independently 0 to 300, with the proviso that a sum total of m, n, o, p and q is greater than 1; and

wherein the B radical has at least one repeat unit in accordance with

including every permutation of repeat units in B.

2 . The composition according to claim 1 , wherein m, n, o, p and q are each independently 0 to 200, with the proviso that the sum total of m, n, o, p and q is greater than 1.

3 . The composition according to claim 1 , wherein a number-average molar mass M n of the polybutadiene is from 200 g/mol to 20,000 g/mol.

4 . The composition according to claim 1 , wherein the polybutadiene has 0% to 80% of double bonds present as 1,2 vinyl double bonds, and 20% to 100% of the double bonds present as 1,4 double bonds, wherein the percentages are based on the total number of double bonds in the polybutadiene.

5 . The composition according to claim 1 , wherein the compound is based on linear polybutadienes.

6 . The composition according to claim 1 , wherein the compound has no pendant (in comb position) polybutadienes.

7 . The composition according to claim 1 , wherein the compound has exclusively pendant (in comb position) repeat units (U), (V), and/or (W).

8 . The composition according to claim 1 , wherein an average molar mass of B is from 40 g/mol to 20,000 g/mol.

9 . The composition according to claim 1 , wherein the composition comprises the compound in an amount of 2 to 100% by weight, based on a total weight of the composition.

10 . The composition according to claim 1 , wherein the composition comprises at least one emulsifier.

11 . The composition according to claim 1 , wherein the composition has a viscosity, measured in a 5% aqueous solution at 20° C. to DIN 53015, of 50-5,000 mPa s.

12 . The composition according to claim 1 , wherein the composition comprises at least one thickener.

13 . The composition according to claim 1 , wherein the composition comprises at least one solid.

14 . An additive, comprising the composition according to claim 1 , wherein the additive is a defoamer additive, a flow control additive, and/or a substrate wetting additive.

15 . A method, comprising:

mixing the composition according to claim 1 into a further composition, wherein the further composition is one selected from the group consisting of a dispersion, a millbase, a paint, a coating, a printing ink, an inkjet, a grind resin, a pigment concentrate, a colour preparation, a pigment preparation, a filler preparation, and a coating composition.

16 . A method of defoaming, comprising:

adding the composition according to claim 1 into a further composition.

17 . The composition according to claim 1 , wherein B is in each case independently a radical of the formula (4b)

18 . The composition according to claim 1 , wherein B is in each case independently a radical of the formula (4c)

19 . The composition according to claim 12 , wherein the at least one thickener is at least one selected from the group consisting of an associative thickener, a hydrophobically modified polyacrylate (HASE), a hydrophobically modified cellulose ether (HMHEC), a hydrophobically modified polyacrylamide (HMPAM), a hydrophobically modified polyether (HMPE), an associative polyurethane thickener, a modified cellulose, an organic polymer, a polyvinyl alcohol, a polyacrylic acid, a polymethacrylic acid, a polyacrylamide, polyvinylpyrrolidone, a polyethylene glycol, a natural thickener or a chemically modified type thereof, a starch, gelatin, casein, konjac flour, an organic thickener, a metal soap, a hardened castor oil or an alkoxylate thereof, a chemically modified fat derivative, an inorganic compound, a sheet silicate (bentonite, hectorite), and a (hydrated) SiO2 particle or a modified type thereof.

20 . The composition according to claim 13 , wherein the at least one solid is at least one selected from the group consisting of silica in a modified or unmodified form, a (alkaline earth) alkali metal soap, calcium stearate, and a mixture thereof.

21 . The composition according to claim 1 , wherein the polybutadiene is essentially free of epoxy groups.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2022
From: FAVRESSE, PHILIPPE; SCHULZ, ALEXANDER; FIEDEL, MICHAEL; OTTO, SARAH; SCHUBERT, FRANK; SCHIERLE, THORSTEN; SEMMLER, HEIKE; STÜTTGEN, ANDREAS
To: EVONIK OPERATIONS GMBH
Reel/Frame 060480/0417 →
Priority Claims (1)
EP 21176163 · May 27, 2021 · regional
Continuity (1)
Related Publication 20220389131A1 · Dec 8, 2022
References Cited (47)
US 3725492A · Ukita et al. · 1973 [cited by applicant]
US 4182814A · Bernemann et al. · 1980 [cited by applicant]
US 4239807A · Feldmann et al. · 1980 [cited by applicant]
US 6218477B1 · Paulen et al. · 2001 [cited by applicant]
US 6353060B1 · Paulen et al. · 2002 [cited by applicant]
US 7442724B2 · Esselborn et al. · 2008 [cited by applicant]
US 8993706B2 · Schubert et al. · 2015 [cited by applicant]
US 9441145B2 · Schubert et al. · 2016 [cited by applicant]
US 9738797B2 · Nilewski et al. · 2017 [cited by applicant]
US 10851189B2 · Krannig et al. · 2020 [cited by applicant]
US 11365270B2 · Krannig et al. · 2022 [cited by applicant]
US 20050085563A1 · Esselborn et al. · 2005 [cited by applicant]
US 20060020082A1 · Rautschek · 2006 [cited by examiner]
US 20110042004A1 · Schubert et al. · 2011 [cited by applicant]
US 20130217930A1 · Haensel et al. · 2013 [cited by applicant]
US 20130281552A1 · Nilewski et al. · 2013 [cited by applicant]
US 20150159068A1 · Schubert et al. · 2015 [cited by applicant]
US 20150307640A1 · Berlineanu et al. · 2015 [cited by applicant]
US 20190315895A1 · Krannig et al. · 2019 [cited by applicant]
US 20210024666A1 · Krannig et al. · 2021 [cited by applicant]
US 20210206972A1 · Schulz et al. · 2021 [cited by applicant]
US 20220047969A1 · Schierle et al. · 2022 [cited by applicant]
US 20230018204A1 · Schubert et al. · 2023 [cited by applicant]
DE 2053484 · 1972 [cited by applicant]
DE 2158878 · 1973 [cited by applicant]
DE 2526366 · 1976 [cited by applicant]
DE 2731067 · 1979 [cited by applicant]
EP 1634940 · 2006 [cited by applicant]
EP 2653205 · 2013 [cited by applicant]
JP 2002105209A · 2002 [cited by examiner]
WO 2010046181 · 2010 [cited by applicant]
WO 2014001300 · 2014 [cited by applicant]
WO 2014075901 · 2014 [cited by applicant]
WO 2022073823 · 2022 [cited by applicant]
English translation of JP-2002105209 (Year: 2002). [cited by examiner]
Lobert et al., U.S. Appl. No. 18/564,035, filed Nov. 24, 2023. [cited by applicant]
U.S. Appl. No. 18/564,035, filed Nov. 24, 2023, Lobert et al. [cited by applicant]
European Search Report dated Nov. 25, 2021 in European Application No. 21176163.0, 5 pages. [cited by applicant]
Evonik Operations: Product Information POLYVEST 130, “Non-functionalized Liquid Polybutadiene” General Description, Jan. 26, 2021, 4 pp. [cited by applicant]
Gao et al., “Facile Synthesis of Amphiphilic Heterografted Copolymers with Crystalline and Amorphous Side Chains”, Macromolecular Chemistry and Physics, vol. 214, 2013, pp. 1677-1687. [cited by applicant]
U.S. Office Action dated Jun. 23, 2023, in U.S. Appl. No. 17/756,423, 14 pages. [cited by applicant]
U.S. Appl. No. 17/756,423, filed May 25, 2022, 2023/0018204, Schubert et al. [cited by applicant]
U.S. Appl. No. 13/771,973, filed Feb. 20, 2013, 2013/0217930, Haensel et al. [cited by applicant]
U.S. Appl. No. 17/126,172, filed Dec. 18, 2020, 2021/0206972, Schulz et al. [cited by applicant]
U.S. Appl. No. 17/399,276, filed Aug. 11, 2021, 2022/0047969, Schierle et al. [cited by applicant]
Lobert et al., U.S. Appl. No. 18/563,143, filed Nov. 21, 2023. [cited by applicant]
U.S. Appl. No. 18/563,143, filed Nov. 21, 2023, Lobert et al. [cited by applicant]