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Patent US6472424 - Stabilized antimicrobial compositions containing halopropynyl compounds and ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsThis invention is directed to stabilized antimicrobial compositions comprising an iodopropynyl compound, and a benzylidene camphor....http://www.google.com/patents/US6472424?utm_source=gb-gplus-sharePatent US6472424 - Stabilized antimicrobial compositions containing halopropynyl compounds and benzylidene camphorsAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS6472424 B1Publication typeGrantApplication numberUS 09/589,010Publication dateOct 29, 2002Filing dateJun 7, 2000Priority dateJun 7, 2000Fee statusPaidPublication number09589010, 589010, US 6472424 B1, US 6472424B1, US-B1-6472424, US6472424 B1, US6472424B1InventorsKamlesh D. Gaglani, Meihua YangOriginal AssigneeTroy Technology Corporation, Inc.Export CitationBiBTeX, EndNote, RefManPatent Citations (36), Non-Patent Citations (1), Referenced by (17), Classifications (14), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetStabilized antimicrobial compositions containing halopropynyl compounds and benzylidene camphors
US 6472424 B1Abstract
This invention is directed to stabilized antimicrobial compositions comprising an iodopropynyl compound, and a benzylidene camphor.
We claim: 1. A stabilized biocidal composition comprising an iodopropynyl compound selected from the group consisting of 3-iodo-2-propynyl propyl carbamate, 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl hexyl carbamate, 3-Iodo-2-propynl cyclohexyl carbamate and 3-iodo-2-propynl phenyl carbamate and a benzylidene camphor and wherein the ratio of benzylidene camphor to iodopropynyl compound is at least 1:20.
2. The composition of claim 1 wherein the benzylidene camphor is a 3-(4-alkoxybenzylidene)camphor.
3. The composition of claim 1 wherein the iodopropynyl carbamate is 3-iodo-2-propynyl butyl carbamate.
4. The composition of claim 3 wherein the benzylidene camphor is a 3-(4-alkoxybenzylidene)camphor.
5. The composition of claim 4 wherein the alkoxy group is selected from the group consisting of methoxy, ethoxy, propoxy and butoxy.
6. The composition of claim 5 wherein the benzylidene camphor is 3-(4-methoxybenzylidene)camphor.
7. The composition of claim 5 wherein the benzylidene camphor is 3-(4-ethoxybenzylidene)camphor.
8. The composition of claim 3 wherein the benzylidene camphor is 3-benzylidenecamphor.
9. The composition of claim 4 wherein the 3-iodo-2-propynyl butyl carbamate and the benzylidene camphor are present in a proportion of from about 1 part 3-iodo-2-propynyl butyl carbamate to 10 parts benzylidene camphor to about 10 parts 3-iodo-2-propynyl butyl carbamate to 1 part benzylidene camphor.
10. The composition of claim 9 wherein the 3-iodo-2-propynyl butyl carbamate and the benzylidene camphor are present in a proportion of from about 1 part 3-iodo-2-propynyl butyl carbamate to 4 parts of the benzylidene camphor to about 4 parts 3-iodo-2-propynyl butyl carbamate to 1 part of the benzylidene camphor.
11. The composition of claim 10 wherein the benzylidene camphor is 3-(4-methoxybenzylidene)camphor.
12. The composition of claim 10 wherein the benzylidene camphor is 3-(4-ethoxybenzylidene)camphor.
13. A paint containing a biocidal composition comprising 3-iodo-2-propynyl butyl carbamate and a benzylidene camphor wherein the ratio of the benzylidene camphor to 3-iodo-2-propynyl butyl carbamate is at least 1:20.
14. The paint of claim 13 wherein the benzylidene camphor is a 3-(4-alkoxybenzylidene)camphor.
15. The paint of claim 14 wherein the benzylidene camphor is 3-(4-methoxybenzylidene)camphor.
16. The paint of claim 14 wherein the benzylidene camphor is 3-(4-ethoxybenzylidene)camphor.
17. The paint of claim 15 wherein the 3-iodo-2-propynyl butyl carbamate and the 3-(4-methoxybenzylidene)camphor are present in a proportion of from about 1 part 3-iodo-2-propynyl butyl carbamate to 4 parts 3-(4-methoxybenzylidene)camphor to about 4 parts of 3-iodo-2-propynyl butyl carbamate to 1 part 3-(4-methoxybenzylidene)camphor.
18. The paint of claim 17 wherein the paint contains from about 0.1% to about 1.0% of the 3-iodo-2-propynyl butyl carbamate.
19. A method for protecting a substrate from fungal infestation and yellowing which comprises coating said substrate with a paint containing a biocidal composition comprising 3-iodo-2-propynyl butyl carbamate and a 3-(4-alkoxybenzylidene)camphor in a 4:1 to 1:4 ratio, said 3-iodo-2-propynyl butyl carbamate being present in said paint at a concentration in the range from about 0.1% to 1.0%.
20. The method of claim 19 wherein 3-(4-methoxybenzylidene)camphor is the 3-(4-alkoxybenzylidene)camphor.
The present invention pertains to a stabilized biocidal composition, a paint containing the stabilized biocidal composition, and a method for protecting a substrate from fungal infestation with the stabilized biocidal composition. The stabilized biocidal composition comprises a halopropynyl compound and a benzylidene camphor.
The present invention provides a significantly more effective way to stabilize halopropynyl compounds, and particularly a halopropynyl carbamate fungicide such as IPBC (known in commerce as Troysan® Polyphase®), against the undesirable degradation and yellowing caused by exposure to UV radiation.
The present invention is directed to a stabilized antimicrobial composition comprising an iodopropynyl compound and a benzylidene camphor.
In another embodiment, the present invention is directed to a paint containing the antimicrobial composition comprising an iodopropynyl compound and a benzylidene camphor.
In yet another embodiment, the invention is directed to a method for protecting a substrate from fungal infestation and yellowing which comprises coating said substrate with an effective amount of a paint containing the antimicrobial composition comprising an iodopropynyl compound and a benzylidene camphor.
It has been found that the integrity of iodopropynyl antimicrobial compositions are significantly enhanced by the inclusion of a benzylidene camphor. The addition of the benzilidene camphor acts to retard any degradation of the iodopropynyl compound rendering the antimicrobial composition more stable and markedly less prone to yellowing.
YC≡C—CH2X
The functional group of which oxygen is a part, is preferably an ether, an ester, or a carbamate group. The functional group of which nitrogen is a part is preferably an amine, an amide, or a carbamate group. The functional group of which sulfur is a part is preferably a thiol, a thiane, a sulfone, or a sulfoxide group. The organic functional group of which carbon is a part is preferably an ester, a carbamate or an alkyl group. Examples of active iodopropynyl derivatives are disclosed in U.S. Pat. Nos. 3,923,870; 4,259,350; 4,592,773; 4,616,004; 4,719,227 and 4,945,109, which are herein incorporated by reference. These iodopropynyl derivatives include compounds derived from propynyl or iodopropynyl alcohols such as the esters, acetals, carbamates and carbonates and the iodopropynyl derivatives of pyrimidines, thiazolinones, tetrazoles, triazinones, sulfamides, benzothiazoles, ammonium salts, carboxamides, hydroxamates, and ureas. Preferred among these compounds is the halopropynyl carbamate, 3-iodo-2-propynyl butyl carbamate. This compound is included within the useful class of compounds having the generic formula wherein R may have one to three linkages corresponding to n and is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted and unsubstituted aryl, alkylaryl, and aralkyl of from 6 to 20 carbon atoms or cycloalkyl and cycloalkenyl groups of from 3 to 10 carbon atoms, and m and n are independently integers from 1 to 3, i.e., they are not necessarily the same.
Particularly preferred are formulations of such halopropynyl carbamates where m is 1 and n is 1 and which have the following formula: Suitable R substituents include alkyls such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and octadecyl; cycloalkyls such as cyclohexyl; aryls, alkary ms and aralkyls such as phenyl, benzyl, toly l, and cumyl; halogenated alkyls and aryls, such as chiorobenzyl and chilorophenyl; and alkoxy aryis such as ethoxyphenyl and the like.
Especially preferred are iodopropynyl carbamates such as 3-iodo-2-propynyl propyl carbamate, 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenyl carbamate, and mixtures thereof.
It might be expected that any UV absorber should offer some protection against degradation and yellowing caused by UV light. Apparently, however, the effectiveness of a UV absorber to prevent degradation cannot be correlated simply with its ability to absorb light. There must be other significant, though less understood criteria at work which must be satisfied in order to provide adequate protection against the deleterious effects of UV light as is evidenced by the test results provided in U.S. Pat. No. 5,938,825.
It has been found that the benzylidene camphor molecules are especially effective in providing protection against degradation and yellowing caused by U.V. light. While substituents on the aromatic ring can modestly affect the effectiveness of the benzylidene camphor to stabilize a halopropynyl compound, the benzylidene camphor molecules as a class all appear to be effective. The kinds of variations in effectiveness noted with other U.V. absorbers based on small structural changes were not seen here. See, for example, U.S. Pat. No. 5,938,825. Indeed, it is the surprising and unexpected finding of this invention that while in other classes of UV absorbers, only certain compounds can be used to provide stabilized antimicrobial compositions containing halopropynyl compounds, all members of the benzylidene camphor group appear to be able to provide this kind of stability.
While benzylidene camphor itself plus nearly all derivatives having substituents on the aromatic ring appear to provide good protection, those having an alkoxy group substituent in the four or para position on the aromatic ring appear to be the most effective and are preferred. Those wherein the alkyl of the alkoxy is a methy a, ethyl, propyl, butyl pentyl or hexyl are especially preferred, with methoxy and ethoxy being most preferred.
The addition of a benzylidene camphor of this invention stabilizes the halopropynyl compounds, particularly halopropynyl carbamate fungicides such as 3-iodo-2-propynyl butyl carbamate (IPBC), in lattices such as acrylic lattices, vinyl acetate acrylic lattices, polyvinyl acetate lattices, styrenated acrylic lattices and styrene butadiene lattices, silicone formulations used for paints and caulks, as well as in leather treatment fluids, other wood treatment formulations and metal working fluids.
The UV component will normally be added in an amount of from about 5% to 400% by weight of the halopropynyl compound, and more usually from 10% to 300% by weight.
Compositions of the present invention will generally be formulated by mixing the UV components in a selected proportion relative to the halopropynyl compound in a liquid vehicle for dissolving or suspending the active components. The present invention specifically contemplates the preparation of a concentrate containing a liquid vehicle and the above noted constituents. The concentrate is useful for adding a halopropynyl compound into particular formulations in the form of a stabilized biocide. The vehicle may also contain a diluent, an emulsifier and a wefting-agent. As noted above, expected uses of the biocidal compositions include protection of wood, paint, coatings, adhesives, paper, textiles, plastics, cardboard, lubricants, caulking, and the like. An extensive list of potential industries and applications for the present invention can be found in U.S. Pat. No. 5,209,930 which is herein incorporated by reference.
When preparing formulations of the present invention for specific applications, other adjuvants which are conventionally employed in compositions intended for such applications may also be added, such as organic binding agents, additional fungicides, auxiliary solvents, processing additives, fixatives, plasticizers, water soluble or water insoluble dyes, colors pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the like. Additional fungicides used in the composition are preferably soluble in the liquid vehicle.
FORMULATION OF STYRENATED ACRYLIC WHITE
NH4OH (7.0%)
Collateral P:Water (1:1)
TiO2 Kerr-McGee
Nopco 8035
Acronal 296D
In the following examples, a number of liquid formulations were prepared, each containing (1) 20% by weight IPBC (Troysan ® Polyphase® P-100), (2) 40% by weight of one of the UV absorbers indicated in each example which follows, and (3) 40% by weight of N-methyl pyrrolidone as a liquid vehicle. Each formulation was then incorporated into the white test paint by mixing in an amount sufficient to provide a test paint having IPBC present at a level of 0.3%. The paint formulations containing IPBC and UV absorbers were then applied on a Leneta chart with help of a 3 mil Bird type applicator. The paint film was allowed to dry for 10-15 minutes and then sprayed with a clear non-yellowing varnish (-3 mils), namely, Kamar Varnish 1312. The varnish was obtained from Krylon Products Group, The Specialty Division, Division of Sherwin-Williams Company, Ohio. The object of the varnish was to trap any of the chromophores formed during subsequent UV light exposure and to assure a short and reproducible test for accessing light-induced yellowing.
The paint film thus produced was exposed to 340 nm UV radiation for four hours and the yellowing was measured by Microflash 200D or Byk Handy Color measurement device. The difference in yellowing between a blank (the white test paint without fungicide) and the candidate paint sample, Δb, was recorded and used as the response for each test. A paint formulation, which did not contain any UV absorber additive but which did have the same amount of IPBC as all the other IPBC-containing paint formulations, was also tested and served as the positive control response.
The formulation added to the paint contained IPBC but had no UV absorber. The Δb value was 7.1. This Example shows that in the absence of a suitable UV absorber, a significant yellow color develops due to a partial degradation of the IPBC.
The Δb value was 2.5 when 3-(4-methylbenzylidene)camphor was used as the UV absorber. This Example shows that there was very little color change when compared to the blank and that the UV absorber was effective in inhibiting degradation of the IPBC.
The Δb value was 2.4 when 3-(3,4-dioxoethylenebenzylidene)camphor was used as the UV absorber. This Example shows that there was very little color change when compared to the blank and that the UV absorber was effective in inhibiting degradation of the IPBC.
The Δb value was 2.7 when 3-(3-methylbenzylidene)camphor was used as the UV absorber. This Example shows that there was very little color change when compared to the blank and that the UV absorber was effective in inhibiting degradation of the IPBC.
The Δb value was 3.4 when 3-(2-methylbenzylidene)camphor was used as the UV absorber. While a slight change in color was perceptible when compared to the blank, the UV absorber was reasonably effective and the amount of yellowing was acceptable.
The Δb value was 2.8 when benzylidenecamphor was used as the UV absorber. This Example shows that there was very little color change when compared to the blank and that the UV absorber was effective in inhibiting degradation of the IPBC.
The Δb value was 3.5 when 3-(4-isopropylbenzylidene)camphor was used as the UV absorber. While a slight color change was perceptible when compared to the blank, the UV absorber was reasonably effective and the amount of yellowing was acceptable.
The Δb value was 3.3 when 3-(3-chlorobenzylidene)camphor was used as the UV absorber. While a slight color change was perceptible when compared to the blank, the UV absorber was reasonably effective and the amount of yellowing was acceptable.
The Δb value was 3.6 when 3-(4-bromobenzylidene)camphor was used as the UV absorber. While a slight color change was perceptible when compared to the blank, the UV absorber was reasonably effective and the amount of yellowing was acceptable.
The Δb value was 1.8 when 3-(4-butoxybenzylidene)camphor was used as the UV absorber. This Example shows that this UV absorber was very effective. Any color change was barely perceptible to the eye.
The Δb value was 1.3 when 3-(4-ethoxybenzylidene)camphor was used as the UV absorber. This Example shows that the UV absorber was very effective. Any color change was barely perceptible to the eye.
The Δb value was 1.3 when 3-(4-methoxybenzylidene)camphor was used as the UV absorber This Example shows that this UV absorber was very effective. Any color change was barely perceptible to the eye.
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Coatings Technology, Federations of Societies for Coatings Technology (Philadelphia, PA), vol. 56 (No. 712), p. 33-48, (May 19, 1984).Referenced byCiting PatentFiling datePublication dateApplicantTitleUS7943644Feb 21, 2007May 17, 2011Lanxess Deutschland GmbhStabilization of iodine-containing biocides by means of special azole compoundsUS8921451Mar 25, 2010Dec 30, 2014Lanxess Deutschland GmbhStabilization of compounds comprising iodineUS9326502Nov 15, 2012May 3, 2016Lanxess Deutschland GmbhStabilization of compounds containing iodine having polymers comprising nitrogenUS20060013833 *Jul 16, 2004Jan 19, 2006Isp Investments Inc.Thermal stabilization of biocides in matrix compositions processed at elevated temperaturesUS20060013847 *Jul 16, 2004Jan 19, 2006Isp Investments Inc.Thermal stabilization of IPBC biocideUS20090192219 *Feb 21, 2007Jul 30, 2009Lanxess Deutschland GmbhStabilization of iodine-containing biocides by means of special azole compoundsEP2236033A1Apr 1, 2009Oct 6, 2010LANXESS Deutschland GmbHStabilisation of compounds containing iodineEP2270087A1Jun 30, 2009Jan 5, 2011LANXESS Deutschland GmbHHeterocyclic 3-ring connections and polymers containing iodine compoundsEP2462805A1Dec 10, 2010Jun 13, 2012LANXESS Deutschland GmbHFormulations containing stabilised compounds containing iodineEP2594132A1Nov 16, 2011May 22, 2013Lanxess Deutschland GmbHStabilisation of iodine containing compounds with polymers containing nitrogenWO2010112387A1Mar 25, 2010Oct 7, 2010Lanxess Deutschland GmbhStabilization of compounds comprising iodineWO2010142795A2Jun 11, 2010Dec 16, 2010Lanxess Deutschland GmbhInorganic carrier materials containing nitrogenWO2011000794A1Jun 28, 2010Jan 6, 2011Lanxess Deutschland GmbhPolymers containing heterocyclic 3-ring compounds and iodine-containing compoundsWO2012076699A1Dec 9, 2011Jun 14, 2012Lanxess Deutschland GmbhBiocide microcapsule formulations containing stabilised iodine-containing compoundsWO2013072427A1Nov 15, 2012May 23, 2013Lanxess Deutschland GmbhStabilization of compounds containing iodine having polymers comprising nitrogenWO2013144145A1Mar 26, 2013Oct 3, 2013Lanxess Deutschland GmbhStable compositions of thiabendazole and iodine-containing fungicidesWO2013144147A1Mar 26, 2013Oct 3, 2013Lanxess Deutschland GmbhFungicide formulations for plasticized pvc* Cited by examinerClassifications U.S. Classification514/478, 524/360, 514/972, 427/160, 106/18.32, 252/182.29, 524/200International ClassificationC09D5/14, A01N47/12Cooperative ClassificationY10S514/972, A01N47/12, C09D5/14European ClassificationA01N47/12, C09D5/14Legal EventsDateCodeEventDescriptionJun 7, 2000ASAssignmentOwner name: TROY TECHNOLOGY CORPORATION, INC., DELAWAREFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:GAGLANI, KAMLESH D.;YANG, MEIHUA;REEL/FRAME:010886/0928Effective date: 20000606Nov 16, 2005FPAYFee paymentYear of fee payment: 4Mar 23, 2010FPAYFee paymentYear of fee payment: 8Mar 26, 2014FPAYFee paymentYear of fee payment: 12RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services