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Esters with Antimicrobial, Bioresistant and Fungal Resistant Properties

a technology of antimicrobial, fungal resistance and antimicrobial/antifungal properties, which is applied in the field of esters with bioresistant, fungal resistant and antimicrobial/antifungal properties, can solve the problems of metal working fluid bases, metal working fluids (mwf) and metal working fluid bases suffering a failure mode, destabilizing the emulsion, and being especially acu

Inactive Publication Date: 2011-04-14
DALY THOMAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013]The fact that the active antimicrobial moiety is covalently linked directly into the backbone of the ester reduces its breakdown at the alkaline pHs required of MWFs. In addition, the moiety is not photo-active or decomposed by sunlight or exposure to mineral salts such as calcium chloride, magnesium hydroxide and sodium chloride as are found in hard and softened water.

Problems solved by technology

In particular metal working fluids (MWF)and metal working fluid bases suffer a failure mode when attacked by microbes.
The problem is especially acute in water extendable and emulsion MWF systems.
The attack of the microbes on the MWF base causes the pH of the system to drop, which destabilizes the emulsion and also increases the corrosion of metal parts that are exposed to the attacked fluid.
Aside from the obvious problems that microbes cause in MWFs, operator health issues also arise due to continuous exposure to high levels of bacteria.
This product family is generally hazardous to handle and causes sensitization in many people when exposed repeatedly.
Additionally, the isothiazolinone family is relatively unstable at the alkaline pH that most MWFs are maintained at.
The formaldehyde condensates do contribute to free formaldehyde in the workplace, but the results are not consistent as to how much formaldehyde they contribute to the workplace atmosphere.
The material fails to act as a food source for the microbes that are able to digest the current MWF bases.

Method used

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  • Esters with Antimicrobial, Bioresistant and Fungal Resistant Properties
  • Esters with Antimicrobial, Bioresistant and Fungal Resistant Properties
  • Esters with Antimicrobial, Bioresistant and Fungal Resistant Properties

Examples

Experimental program
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Effect test

example 1

Production of a Metal Working Fluid Base

[0031]A vessel equipped with a nitrogen blanket and condenser was charged with 1128 g (4 moles) of oleic acid, 400 g BNPD (2 moles) and 2 g conc. Sulfuric acid. The vessel was heated to 288 F when condensation began. The temperature leveled off between 352 F and 356 F and was kept at temperature for 3 hours. The BNPD dioleate recovered was a dark brownish liquid.

[0032]The dioleate produced was then incorporated into a standard MWF base at 10% (1,300 PPM BNPD) in the concentrate by substituting it for part of the existing ester. The bases were then subjected to ASTM 3946-92, “Standard Test Method for Evaluating the Bacteria Resistance of Water-Dilutable Metal Working Fluids”. On Day 5 of the testing, the BNPD ester containing fluid showed bacterial count of 3×10̂3 CFU / ml, which is considered under control. The control sample had a bacterial count of 1×10̂7, which is not considered under control.

[0033]At an incorporation level of 6% (823 PPM BNP...

example 2

Synthesis of Acid Functional, Pendant Fatty Chain Containing, BNPD Ester

[0035]In a vessel with heat, agitation, condenser, and nitrogen blanketing is charged 400 g (2 moles) of BNPD, 616 g (4 moles) of 1,2-Cyclohexanedicarboxylic anhydride (HHPA) and 150 g xylene as a reflux solvent. The vessel is heated to 323 F at which point the reaction exothermed and began to darken. The temperature was then reduced and held at 302 F for one hour. 1162 g of final product was recovered that was a thick, dark transparent liquid. This product will be referred to as HHPA / BNPD-003.

[0036]In a vessel with heat, agitation, condenser, and nitrogen blanketing is charged 706 g of HHPA / BNPD-003 from above, 806 g of Crisamine PCD-2, 2 mole ethoxylate of primary coco amine, and 150 g xylene as a reflux solvent. The vessel is heated to 350 F for three hours until the theoretical water loss was collected in the trap and the evolution of water stopped. Approximately 1,400 g of a dark, thick translucent liquid w...

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Abstract

A bromine / nitro moiety linked into the backbone of an ester or other compound over a wide range of occurrence rates provides antimicrobial, bio-resistant and fungal resistant properties for metal working fluids (MWF)s and other coatings. The moiety can be have the bromo and nitro groups linked to the same or different carbon atoms. The present invention also relates to urethanes, urea, amides, imides, carbonates, ethers, siloxanes, and many other types of linkages essential to MWF bases.

Description

[0001]This application is a divisional application from application Ser. No. 12 / 287,726 filed Oct. 10, 2008 which was a continuation-in-part of application Ser. No. 11 / 800,569 filed May 7, 2007 which was a continuation in part of application Ser. No. 10 / 603,356 filed Jun. 25, 2003 which claimed priority from U.S. Provisional patent application No. 60 / 392,007 filed Jun. 26, 2002. Application Ser. Nos. 12 / 287,726, 11 / 800,569, 10 / 603,356 and 60 / 392,007 are hereby incorporated by reference. This application also incorporates by reference my other patent application Ser. No. 10 / 350,928 filed Jan. 23, 2003 entitled Polymers with Antimicrobial, Bioresistant and Fungal Resistant Properties.[0002]The text of this divisional application is substantially identical to that of grandparent application Ser. No. 10 / 603,356.BACKGROUND[0003]1. Field of the Invention[0004]The present invention relates to the field of esters and more particularly to esters with bioresistant, fungal resistant and antimi...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07F7/10C07C271/10
CPCA01N37/12C08G77/392C07C205/51C10M105/56C10M133/32C10M2215/003C10M2215/202C10N2230/16C10N2230/18C10N2240/401C11D1/667C11D7/32C23F11/145C23F11/147C07C229/12C07C205/50C07F7/0854C08G77/388B01D19/0413C10N2030/16C10N2030/18C10N2040/22C07F7/0838C07C57/52C09K15/20
Inventor DALY, THOMAS
Owner DALY THOMAS
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