IP Library Granted Patent US 9,181,398
Granted Patent B2
US 9,181,398 · App. 13/455,768 · Granted Nov 10, 2015

Organopolysilicone polyether drainage aid

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,181,398
App. No.
13/455,768
Granted
Nov 10, 2015
Kind
B2
Abstract

The present invention relates to a drainage aid composition and its use in pulp washing process. More particulary, this invention relates to drainage aid composition of silicone polyethers prepared via zinc catalized dehydrogenative coupling of alcohol terminated polyethers with silicone oligomers and polymers comprising of at least one silicon bonded hydrogen. The compostion of this invention exhibit excellent drainage properties.

Claims (71)

1. A drainage aid composition comprising functionalized organopolysilicones comprising pendent polyethers and/or aliphatic hydrocarbons compounds having the general formula:

wherein the repeating units are block or random,

wherein R comprises, identical or different, hydrogen, phenyl, ethyl or methyl moiety,

n is an integer from 1 to 1000,

m is a positive integer ranging from 1 to 1000,

f is selected from the group consisting of B, Al, Sn, Si, Ge, O, S, phosphate, —COO—, N-A 1 and A 2 -P,

A 1 is a hydrogen or a hydrocarbon having 1-3 carbon atoms,

A 2 is a hydrogen or a hydrocarbon having 1-3 carbon atoms or any aromatic ring,

x comprises y-O—(CH 2 CHR 1 O) v (CH 2 CHR 2 O) z (CH 2 ) w — or y-(CH 2 ) w —,

y comprises an aliphatic hydrocarbon moiety wherein the number of carbon atoms is between 1-18,

v is an integer from 1 to 1000,

z is 0 or a positive integer ranging from 1 to 1000, w is a positive integer ranging from 1 to 18,

R 1 is methyl, ethyl, or propyl, and

R 2 is hydrogen, methyl, ethyl, or propyl

R 3 , identical or different, is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, alkyl radicals with 5-18 carbon atoms, substituted and un-substituted aromatic hydrocarbon, fluorocarbon, halocarbon, and cyclic hydrocarbons; and

a catalyst selected from finely divided zinc.

2. A composition comprising functionalized organopolysilicones comprising pendent polyethers and/or aliphatic hydrocarbons selected from the following structures:

wherein

R is, identically or differently, a phenyl, ethyl or methyl moiety,

m is an integer from 1 to 1000,

n is 0 or an integer from 1 to 2000,

f is identical or different, a divalent radical selected from the following; —S—, —N A 1 —, —COO—, and oxygen,

A 1 is a hydrogen or a hydrocarbon having 1-3 carbon atoms,

x, identical or different, is selected from the group consisting of identical or different polyether moieties, identical or different saturated or un-saturated hydrocarbon radicals or mixtures thereof,

wherein the polyether moieties have the general formula (i) y-O—(CH 2 CHR 1 O) v (CH 2 CHR 2 O) z (CH 2 ) w —

wherein the hydrocarbon radicals have the general formula (ii) y-(CH 2 ) w —,

wherein y is an aliphatic hydrocarbon moiety wherein the number of carbon atoms is between 1-18,

v is an integer from 1 to 1000,

z is a positive integer ranging from 0 to 1000,

w is a positive integer ranging from 1 to 18,

R 1 is methyl, ethyl, or propyl,

R 2 is hydrogen, methyl, ethyl, or propyl, and

R 3 , identical or different, is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, alkyl radicals with 5-18 carbon atoms, substituted and un-substituted aromatic hydrocarbon, fluorocarbon, halocarbon, and cyclic hydrocarbons; and a catalyst selected from finely divided zinc.

3. The composition of claim 2 wherein x comprises at least one polyether moiety.

4. The composition of claim 1 or 2 , wherein x comprises at least two polyether moieties selected from the group consisting of

and mixtures thereof;

wherein p and q are the weight % of propylene glycol and ethylene glycol units of the functionalized organopolysilicones.

5. The composition of claim 4 , wherein x comprises a mixture of moieties wherein the mixture comprises at least one polyether moiety selected from the group consisting of polyether-1, polyether-2, polyether-3, polyether-4, polyether-5, polyether-6, polyether-7, polyether-8, and polyether-9, and at least one aliphatic moiety selected from the general formula (ii).

6. The composition of claim 5 , wherein x comprises a mixture of polyether moieties and hydrocarbon moieties wherein at least one polyether moiety is a polyether-6 moiety and at least one hydrocarbon moiety is a linear aliphatic hydrocarbon consisting of 1-18 carbon atoms, preferably from 1-9 carbon atoms.

7. The composition of claim 2 , wherein the functionalized organopolysilicone comprises DA-6.

8. The composition of claim 1 or 2 , wherein the aliphatic hydrocarbon comprises from 10 to 90 mole % of the x moieties.

9. The composition of claim 2 , wherein at least one polyether moiety comprises polyether-3, wherein the weight percent, “q”, of ethylene oxide units in the polyether is from 0 to 99.99%.

10. The composition of claim 4 , wherein x comprises a mixture of at least two polyethers

a) polyether 3 with a q of from 30 to 40 wt %, and

b) polyether 3 with a q of from 5 to 20 wt %.

11. The composition of claim 10 wherein wt % of polyether 3 with a q of from 30 to 40 wt % in the composition is from 30 to 40 wt % of the composition.

12. The composition of claim 4 wherein the functionalized organopolysilicone comprises DA-6 and wherein x comprises a polyether-6 moiety, wherein polypropylene glycol (PO) and polyethylene glycol (EO) units are randomly distributed and wherein the weight percent of EO in polyether-6 is from 10 to 90 wt %.

13. The composition of claim 12 wherein weight percent of EO in polyether-6 is from 40 to 55 wt %.

14. The composition of claim 12 , wherein the functionalized organopolysilicone comprises DA-6 and wherein x is a mixture of moieties wherein the mixture comprises at least one polyether-6 moiety and at least one additional polyether moiety selected from the group consisting of polyether-1, polyether-2, polyether-3, polyether-4, polyether-5, polyether-7, polyether-8, polyether-9 and mixtures thereof.

15. A method of making the composition of claim 1 comprising:

heating a polyether or aliphatic hydrocarbon, under inert conditions at a temperature of from 90° C.-160° C. for at least two hours to reduce the water content below 1000, adding an organosilicone polymer to the polyether in the presence of a zinc catalyst wherein the amount of catalyst added to the reaction vessel is from 0.5-1.0 wt % based on the amount of reactants, allowing the components to react, cooling the reaction vessel to ambient temperature after the completion of silicone addition to the reaction vessel.

16. A method of improving drainage and filtration rates in cellulosic washing and de-watering processes compromising

adding a functionalized organopolysilicones comprising pendent polyethers and/or aliphatic hydrocarbons compounds having the general formula:

wherein the repeating units are block or random,

wherein R comprises, identical or different, hydrogen, phenyl, ethyl or methyl moiety,

n is an integer from 1 to 1000,

m is a positive integer ranging from 1 to 1000,

f is selected from the group consisting of B, Al, Sn, Si, Ge, O S, phosphate, —COO—, N-A 1 and A 2 -P,

A 1 is a hydrogen or a hydrocarbon having 1-3 carbon atoms,

A 2 is a hydrogen or a hydrocarbon having 1-3 carbon atoms or any aromatic ring,

x comprises y-O—(CH 2 CHR 1 O) v (CH 2 CHR 2 O) z (CH 2 ) w — or y-(CH 2 ) w —,

y comprises an aliphatic hydrocarbon moiety wherein the number of carbon atoms is between 1-18,

v is an integer from 1 to 1000,

z is 0 or a positive integer ranging from 1 to 1000, w is a positive integer ranging from 1 to 18,

R 1 is methyl, ethyl, or propyl, and

R 2 is hydrogen, methyl, ethyl, or propyl

R 3 , identical or different, is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, alkyl radicals with 5-18 carbon atoms, substituted and un-substituted aromatic hydrocarbon, fluorocarbon, halocarbon, and cyclic hydrocarbons; and

a catalyst selected from finely divided zinc,

to an aqueous slurry containing cellulosic material wherein the composition is added at a dosage of from 0.001 to 4 lb for every 2000 lb of cellulosic material in the aqueous slurry and wherein the solids content of the aqueous slurry is from 0.01 to 30% solids.

17. The method of claim 16 wherein the aqueous slurry has a pH in the range of from 10.5 to 13.5.

18. The method of claim 16 , wherein the aqueous slurry is derived from the group consisting of a brown stock washing process, a bleach plant process, and a market pulp machine process.

Assignments (22)
SECURITY INTEREST Recorded Nov 14, 2025
From: CHEM-AQUA, INC.; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; NCH CORPORATION; NCH LIFE SCIENCES LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073570/0838 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073564/0864 →
SECURITY AGREEMENT (NOTES) Recorded Oct 10, 2025
From: DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073061/0885 →
RELEASE OF 2023 NOTES PATENT SECURITY INTERESTS Recorded Oct 10, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073074/0198 →
SECURITY AGREEMENT (2024 NOTES) Recorded Jun 24, 2024
From: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 067824/0278 →
2023 NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE GLOBAL CORPORATION
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064225/0170 →
SECURITY AGREEMENT (NOTES) Recorded Sep 14, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
Reel/Frame 061432/0821 →
ABL PATENT SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: BANK OF AMERICA, N.A.
Reel/Frame 058102/0122 →
RELEASE OF SECURITY INTEREST Recorded Nov 10, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 058856/0724 →
RELEASE OF SECURITY INTEREST Recorded Nov 10, 2021
From: CITIBANK, N.A.
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 058848/0636 →
NOTES SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 058103/0066 →
TERM LOAN PATENT SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: GOLDMAN SACHS BANK USA
Reel/Frame 058102/0407 →
INTELLECTUAL PROPERTY FIRST LIEN SECURITY AGREEMENT RELEASE Recorded Jul 20, 2018
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 046594/0252 →
INTELLECTUAL PROPERTY SECOND LIEN SECURITY AGREEMENT RELEASE Recorded Jul 20, 2018
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 047058/0800 →
SECOND LIEN NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jul 20, 2018
From: SOLENIS TECHNOLOGIES, L.P.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 046629/0213 →
FIRST LIEN NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jul 20, 2018
From: SOLENIS TECHNOLOGIES, L.P.
To: CITIBANK, N.A., COLLATERAL AGENT
Reel/Frame 046595/0241 →
NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS (SECOND LIEN) Recorded Aug 14, 2014
From: SOLENIS TECHNOLOGIES, L.P.
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 033535/0847 →
NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS (FIRST LIEN) Recorded Aug 14, 2014
From: SOLENIS TECHNOLOGIES, L.P.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 033535/0806 →
U.S. ASSIGNMENT OF PATENTS Recorded Aug 4, 2014
From: HERCULES INCORPORATED
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 033470/0922 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Mar 18, 2013
From: THE BANK OF NOVA SCOTIA
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; ISP INVESTMENTS INC.; HERCULES INCORPORATED
Reel/Frame 030025/0320 →
SECURITY AGREEMENT Recorded May 22, 2012
From: HERCULES INCORPORATED; ISP INVESTMENTS INC.
To: THE BANK OF NOVA SCOTIA
Reel/Frame 028252/0499 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2012
From: AL-BADRI, ZOHA; BOLTON, TODD S.
To: HERCULES INCORPORATED
Reel/Frame 028106/0119 →