IP Library Granted Patent US 7,316,738
Granted Patent B2
US 7,316,738 · App. 10/961,155 · Granted Jan 8, 2008

Milled submicron chlorothalonil with narrow particle size distribution, and uses thereof

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Quick Facts
Patent No.
US 7,316,738
App. No.
10/961,155
Granted
Jan 8, 2008
Kind
B2
Abstract

A method of milling chlorothalonil to form a sub-micron product having a narrow particle size distribution is presented. The milling involves wet milling of the chlorothalonil with high density milling media having a diameter between 0.1 mm and 0.8 mm, preferably between 0.2 mm and 0.7 mm, and a density equal to or greater than 3.8 g/cc, preferably greater than 5.5 g/cc, in a ball mill using between about 40% and 80% loading of the mill volume with milling media, and having the chlorothalonil suspended in an aqueous milling liquid which comprises one or more surface active agents. The milling speed is preferably high, for example from about 1000 rpm to about 4000 rpm. The milled product can be used in foliar applications at a lower effective dosage than prior art formulations, can be used in improved antifouling paint formulations, and can be used in new applications such as the direct injection of solid chlorothalonil particulates in wood to act as a long lasting wood preservative.

Claims (29)

1. A milled chlorothalonil product comprising:

chlorothalonil particles, wherein the chlorothalonil particles have a mean volume particle diameter d 50 of about 0.6 microns or less and a d 90 , which is a diameter such that 90 volume percent of the particles have a diameter of the d 90 , or less, of less than 1 micron.

2. The chlorothalonil product of claim 1 wherein the d 50 is about 0.4 microns or less.

3. The chlorothalonil product of claim 1 wherein the d 50 is about 0.4 microns or less and the d 90 is less than 0.7 microns.

4. The chlorothalonil product of claim 1 wherein the d 50 is between about 0.1 and about 0.3 microns.

5. The chlorothalonil product of claim 1 wherein the chlorothalonil particles have a mean volume particle diameter d 98 , which is a diameter such that 98 volume percent of the product has a diameter of the d 98 or less, of about 0.5 microns or less.

6. The chlorothalonil product of claim 5 wherein the product is dispersed in wood.

7. The chlorothalonil product of claim 5 wherein the d 98 is less than about 0.3 microns.

8. The chlorothalonil product of claim 1 wherein the chlorothalonil particles have a mean volume particle diameter d 99 , such that 99 volume percent of the product has a diameter of the d 99 or less of less than about 0.7 microns.

9. The chlorothalonil product of claim 8 wherein the product is dispersed in wood.

10. The chlorothalonil product of claim 1 wherein the chlorothalonil particles have a mean volume particle diameter d 96 , such that 96 volume percent of the particles have a diameter of the d 96 or less of less than about 0.6 microns.

11. The chlorothalonil product of claim 1 wherein the d 50 is between about 0.1 and about 0.3 microns and where 80% by weight of the chlorothalonil particles have a size/diameter between about 0.05 microns and about 0.4 microns.

12. The chlorothalonil product of claim 6 wherein the d 98 is less than about 0.2 microns.

13. The chlorothalonil product of claim 1 wherein the d 50 is between about 0.1 and about 0.3 microns and the d 90 is less than about 0.4 microns.

14. The chlorothalonil product of claim 13 wherein the product is dispersed in wood.

15. A milled chlorothalonil product comprising:

chlorothalonil particles,

wherein the chlorothalonil particles have a mean volume particle diameter d 50 of about 0.7 microns or less and a d 90 which is a diameter such that 90 volume percent of the particles have a diameter of the d 90 or less, of less than 3 times the d 50 .

16. The chlorothalonil product of claim 15 wherein the particles have a d 10 , which is a diameter such that 10 volume percent of the particles have a diameter of the d 10 or less, of greater than 0.25 times the d 50 .

17. The chlorothalonil product of claim 15 wherein the d 50 is less than about 0.4 microns.

18. The chlorothalonil product of claim 15 wherein the d 50 is between about 0.1 and about 0.3 microns.

19. The chlorothalonil product of claim 15 wherein the chlorothalonil particles are is contained in an aqueous slurry further comprising dispersants and stabilizers.

20. The chlorothalonil product of claim 15 wherein the chlorothalonil particles are contained in an aqueous slurry further comprising between about 2% and about 60% by weight of dispersants and stabilizers, based on the weight of the chlorothalonil.

21. The chlorothalonil product of claim 15 wherein the product further comprises surface active agents in an amount such that the chlorothalonil particles are non-agglomerating and non-interacting in an aqueous dispersion.

22. The chlorothalonil product of claim 15 wherein the d 90 is less than two times the d 50 .

23. The chlorothalonil product of claim 22 wherein the d 50 is about 0.2 microns.

24. The chlorothalonil product of claim 23 wherein the particles have a mean volume particle diameter d 10 , such that about 10 volume percent of the particles have a diameter of the d 10 or less, of greater than 0.25 times the d 50 .

25. The chlorothalonil product of claim 22 wherein the product is dispersed on foliage.

26. The chlorothalonil product of claim 22 wherein the product is dispersed in non-fouling paint.

Assignments (17)
RELEASE (REEL 033591 / FRAME 0020) Recorded Jun 28, 2022
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: KOPPERS DELAWARE, INC. (F/K/A KOPPERS INDUSTRIES OF DELAWARE, INC.); KOPPERS PERFORMANCE CHEMICALS INC. (F/K/A OSMOSE, INC.); KOPPERS INC. (F/K/A KOPPERS INDUSTRIES, INC); KOPPERS PERFORMANCE CHEMICALS NEW ZEALAND LIMITED (F/K/A OSMOSE NEW ZEALAND); OSMOSE UTILITIES SERVICES, INC.
Reel/Frame 060448/0192 →
RELEASE OF PATENT SECURITY INTERESTS Recorded Jun 20, 2022
From: PNC BANK, NATIONAL ASSOCIATION
To: KOPPERS DELAWARE, INC.; KOPPERS PERFORMANCE CHEMICALS INC. (F/K/A OSMOSE, INC.); KOPPERS UTILITY AND INDUSTRIAL PRODUCTS INC. (F/K/A COX INDUSTRIES, INC.); KOPPERS INC. (F/K/A KOPPERS INDUSTRIES, INC.)
Reel/Frame 060390/0207 →
SECURITY AGREEMENT Recorded Jun 20, 2022
From: KOPPERS DELAWARE, INC.; KOPPERS PERFORMANCE CHEMICALS INC.
To: PNC BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 060390/0246 →
PATENT, TRADEMARK AND COPYRIGHT SECURITY AGREEMENT Recorded Sep 20, 2017
From: KOPPERS, INC.; KOPPERS HOLDINGS INC.; KOPPERS DELAWARE, INC.; KOPPERS ASIA LLC; KOPPERS CONCRETE PRODUCTS, INC.; CONCRETE PARTNERS, INC.; KOPPERS PERFORMANCE CHEMICALS, INC.; KOPPERS RAILROAD STRUCTURES INC.; KOPPERS WORLD-WIDE VENTURES CORPORATION; KOPPERS VENTURES INC.; KOPPERS-NEVADA LIMITED-LIABILITY COMPANY; KOPPERS NZ LLC; WOOD PROTECTION MANAGEMENT LLC; WOOD PROTECTION LP
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 043920/0523 →
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVE PATENT NUMBER 8221797 PREVIOUSLY RECORDED AT REEL: 034036 FRAME: 0363. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Dec 9, 2014
From: OSMOSE, INC.
To: KOPPERS PERFORMANCE CHEMICALS INC.
Reel/Frame 034563/0407 →
CHANGE OF NAME Recorded Oct 23, 2014
From: OSMOSE, INC.
To: KOPPERS PERFORMANCE CHEMICALS INC
Reel/Frame 034036/0363 →
RELEASE OF SECURITY INTERST IN INTELLECTUAL PROPERTY Recorded Aug 27, 2014
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: OSMOSE, INC.
Reel/Frame 033645/0778 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Aug 27, 2014
From: CREDIT SUISSE AG, CAYMAND ISLANDS BRANCH, AS COLLATERAL AGENT
To: OSMOSE, INC. (FORMERLY OSMOSE WOOD PRESERVING, INC.)
Reel/Frame 033645/0796 →
PATENT, TRADEMARK AND COPYRIGHT SECURITY AGREEMENT Recorded Aug 22, 2014
From: KOPPERS INC.; KOPPERS HOLDINGS INC.; KOPPERS DELAWARE, INC.; KOPPERS ASIA LLC; KOPPERS CONCRETE PRODUCTS, INC.; CONCRETE PARTNERS, INC.; KOPPERS WORLD-WIDE VENTURES CORPORATION; KOPPERS VENTURES LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 033591/0020 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 26, 2012
From: OSMOSE, INC.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 029351/0791 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 4, 2012
From: OSMOSE, INC. (FORMERLY OSMOSE WOOD PRESERVING, INC.)
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 028158/0611 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2010
From: PHIBROTECH, INC.; PHIBROWOOD, LLC
To: OSMOSE, INC
Reel/Frame 023937/0585 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Dec 10, 2009
From: WELLS FARGO FOOTHILL, INC.
To: PHIBRO-TECH, INC.
Reel/Frame 023627/0807 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2008
From: PHIBRO-TECH, INC.
To: PHIBROWOOD, LLC.
Reel/Frame 021817/0763 →
PATENT SECURITY AGREEMENT Recorded Feb 4, 2008
From: PHIBROWOOD, LLC
To: WELLS FARGO FOOTHILL, INC., AS COLLATERAL AGENT
Reel/Frame 020459/0104 →
AMENDMENT NUMBER ONE TO PATENT SECURITY AGREEMENT Recorded Aug 21, 2006
From: PHIBRO-TECH, INC.
To: WELLS FARGO FOOTHILL, INC.
Reel/Frame 018148/0478 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2005
From: RICHARDSON, H. WAYNE; HODGE, ROBERT L.
To: PHIBRO-TECH, INC.
Reel/Frame 015710/0328 →