[go: up one dir, main page]

WO2008079417A2 - Utilisation de bétaïnes d'ammonium quaternaire dans la prévention de la moisissure, du mildiou et des champignons dans une construction nouvelle et/ou existante - Google Patents

Utilisation de bétaïnes d'ammonium quaternaire dans la prévention de la moisissure, du mildiou et des champignons dans une construction nouvelle et/ou existante Download PDF

Info

Publication number
WO2008079417A2
WO2008079417A2 PCT/US2007/060240 US2007060240W WO2008079417A2 WO 2008079417 A2 WO2008079417 A2 WO 2008079417A2 US 2007060240 W US2007060240 W US 2007060240W WO 2008079417 A2 WO2008079417 A2 WO 2008079417A2
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
groups
article
quaternary ammonium
ammonium compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2007/060240
Other languages
English (en)
Other versions
WO2008079417A3 (fr
Inventor
Joe D. Sauer
George W. Cook, Jr.
Christopher S. Knight
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Albemarle Corp
Original Assignee
Albemarle Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Albemarle Corp filed Critical Albemarle Corp
Publication of WO2008079417A2 publication Critical patent/WO2008079417A2/fr
Publication of WO2008079417A3 publication Critical patent/WO2008079417A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron

Definitions

  • the present invention relates to the use of quaternary ammonium compositions in the prevention of unwanted microbial growth such as mold, fungus, and mildew in new and/or existing construction.
  • Quaternary ammonium compounds or "quats” for short find use in many industrial applications. Quats are loosely defined as a group of compounds generally having the formula RiR 2 RsR 4 -TST + Y " , where the radicals may be the same, different, or part of a ring and Y is a counter anion. Typically, but not always, one of the radicals is a long-chain alkyl group. In most industrial applications, these quat molecules are complexed with a counter ion (anion) to provide for an "active" molecule.
  • a counter ion anion
  • the use or application of at least one quaternary ammonium compound, sometimes only one, sometimes more than one wherein the more than one contemplates quaternary ammonium compounds having the same or different counter anions, or a prophylactic solution comprising at least one quaternary ammonium compound, sometimes only one sometimes more than one wherein the more than one contemplates quaternary ammonium compounds having the same or different counter anions, can provide for an effective, non-oxidizing prophylactic measure for microbial organisms.
  • the application of the at least one quaternary ammonium compound or the prophylactic solution can also impart to the one or more articles some flame retardant properties.
  • the application of the at least one quaternary ammonium compound or the prophylactic solution can also impart to the one or more articles some termite repellant properties.
  • the one or more articles to which the at least one quaternary ammonium compound or the prophylactic solution is applied must obviously be susceptible to termite damage, i.e. cellulosic substrates such as wood, cotton, paper, or bagassc-bascd building products. Non- limiting examples of these products include ceiling tiles, wooden furniture, wallboards, etc., and the like.
  • repelling termites it is meant that the termites do not feed on the quat treated cellulosic material, and in essence may resort to cannibalistic behavior for food or search for a different food source, if one is available, instead of feeding on the quat treated cellulosic material as a food source.
  • the present invention relates to a method for the prevention and/or inhibition of microbial organism growth.
  • the method comprises applying to one or more article a quaternary ammonium compound having the formula: wherein R 1 , R2, R 3 , and R 4 are selected from z " ) substituted or unsubstituted alkyl groups or if) substituted or unsubstituted alkenyl groups, wherein if i) or if) is substituted, they have one or more substituent groups selected from aryl, heterocyclyl, hydroxyl, ester, benzyl, carboxyl, halo, nitro, cyano, alkoxy or oxo groups; m is 1, 2, or 3; R5 is selected from i) substituted or unsubstituted alkyl groups or if) substituted or unsubstituted alkenyl groups, wherein iff) or if) is substituted, they have one or more substituent groups selected from aryl, heterocyclyl, hydroxyl, ester, benzyl, carboxyl, halo, nitro, cyan
  • a prophylactic solution comprising at least one quaternary ammonium compound is applied to the one or more article.
  • Microbial microbe
  • microbial organism can be used interchangeably herein and are used herein in the broadest sense and are meant to include one or more of the following: molds, mildews, funguses, and the like. In some embodiments, the microbial is considered a contaminant to the one or more article(s)
  • an environment that can facilitate or encourage the growth of at least one microbial it is meant an environment that facilitates or encourages the growth of one or more molds, mildews, funguses, and the like.
  • these environments are generally moist or humid environments wherein the relative humidity can reach 60% or greater and/or wherein poor ventilation is available, which contributes to moist or humid conditions.
  • the environment is also warm, for example, 55 0 F (average temperature) or higher.
  • building as used herein is also used in its broadest sense and is meant to include homes, office and/or other commercial buildings, storage units or buildings, apartments, mobile homes, travel trailers, detached garages, camps, and the like.
  • Construction material as used herein is also used in its broadest sense and is meant to encompass any material used in the construction of homes and buildings upon which microbial organisms can grow.
  • construction material as used herein is meant to encompass wood, cotton, cardboard, liner board, other similar paper products, composite assemblies, and the like.
  • the one or more articles to which the quaternary ammonium compound or the prophylactic solution is applied is a construction material.
  • the article can be any one of the following: i) gypsum board; ii) ceiling tiles or other ceiling material made form natural or synthetic materials; ii ⁇ ) particleboard or other similar composite material used in the construction of a building, i.e. fiber board, press-board, and the like; iv) synthetic wood, i.e.
  • the article is selected from one or more of the following: curtains, bed sheets, furniture (sofas, chairs, tables, beds, and the like), and the like.
  • Quaternary Ammonium Compound is selected from one or more of the following: curtains, bed sheets, furniture (sofas, chairs, tables, beds, and the like), and the like.
  • the term "quaternary ammonium compound”, “quat”, or “boron-quat” as used herein refers to a compound in which at least one nitrogen atom is joined to four organic radicals leaving a net positive charge.
  • the organic radicals can be alkyl or alkenyl (unsaturated alkyls) groups that are linear or branched, substituted or unsubstituted, or mixtures thereof.
  • the term “quaternary ammonium compound” or “quat” is also intended to encompass a compound in which more than one nitrogen is joined to four organic radicals.
  • one of the four organic radicals of a quat may be a "shared" radical with a second quat.
  • the quaternary ammonium compounds used in the present invention can be represented by the formula:
  • m can be 1, 2, or 3
  • X is selected from an element having a net ionic charge of —2, sometimes oxygen (“O").
  • the boron-containing quats according to the present differ from those previously disclosed in the art in that they are not complexed with a counter anion. Instead, boron, the active species imparting the desired properties to the quat, is a part of the qxxat molecule, and the anion X providing the ionic charge necessary to provide for a quat having a net ionic charge of 0, which can be suitably selected from elements having a net ionic charge of —2, in some embodiments oxygen, is also part of the boron-containing quat molecule.
  • the inventors hereof believe that this provides for a more effective quat molecule than previously disclosed because the quat itself has a net ionic charge of zero without the need for a counter anion.
  • the counter anion the active species imparting the desired properties to the quat, in previously disclosed quats, was held by an ionic bond.
  • the bond between the boron active species and the quat molecule is a covalent bond.
  • the inventors hereof theorize that exposure to the elements, i.e. wind, rain, washing, pressure washing, etc., of a substrate treated with a quat complexed with a counter anion could cause the ionic bond between the active species, e.g.
  • the five carbon chains, i.e. Ri, R 2 , R 3 , R 4 , and R5 of the quats used in the present invention are independently selected from f) substituted or unsubstituted alkyl groups or if) substituted or unsubstituted alkenyl groups, wherein if f) or if) is substituted, they have one or more substituent groups selected from aryl, heterocyclyl, hydroxyl, ester, benzyl, carboxyl, halo, nitro, cyano, alkoxy or oxo groups.
  • Alkyl and alkenyl groups suitable for use in the quats are those that contain in the range of from 1 to 20 carbon atoms.
  • Ri , R2, and R 4 are independently chosen from alkyl groups having in the range of from 1 to 3 carbon atoms
  • R 3 are independently chosen from 6 to 20 carbon atom-containing groups selected from f) substituted or unsubstituted alkyl groups or ii) substituted or unsubstituted alkenyl groups, wherein if i) or ii) is substituted, they have one or more substituent groups selected from aryl, heterocyclyl, hydroxyl, ester, benzyl, carboxyl, halo, nitro, cyano, alkoxy or oxo groups; and m is 1, 2, or 3.
  • Ri and R 2 are methyl groups
  • R 3 is chosen from alkyl groups having in the range of from 1 to 3 carbon atoms
  • R4 is selected from unsubstituted alkyl groups containing in the range of from 8 to 14 carbon atoms.
  • R 3 is an unsubstituted alkyl group containing in the range of from 8 to 10 carbon atoms
  • R 3 is an ethyl group.
  • R], R2, R 3 and R) are alkyl groups having in the range of from 1 to 3 carbon atoms, sometimes methyl groups.
  • Rs is OH.
  • R 4 is selected from i) substituted or unsubstituted alkyl groups that contain from 13 to 16, sometimes 14 to 16, sometimes 14, carbon atoms or if) substituted or unsubstituted alkenyl groups that contain from 13 to 16, sometimes 14 to 16, sometimes 14, carbon atoms, wherein if f) or if) is substituted, they have one or more substituent groups selected from aryl, heterocyclyl, hydroxyl, ester, benzyl, carboxyl, halo, nitro, cyano, alkoxy or oxo groups. These carbon chains can be saturated or unsaturated, preferably unsubstituted.
  • R 3 can be selected from unsaturated substituted or unsubstituted, preferably unsubstituted, alkyl groups containing from 13 to 16, sometimes 14 to 16, sometimes 14, carbon atoms.
  • Ri , R 2 , and R 4 are independently chosen from alkyl groups having from 1 to 4, sometimes 1 to 3, in some embodiments 2 to 4, carbon atoms.
  • R 5 is OH.
  • m is 2, and one of the four organic radicals of a quat may be a "shared" radical with a second quat.
  • R 4 is shown as the shared radical, the shared radical can be any of Ri , R 2 , Rs, or R 4 .
  • the quaternary ammonium compounds used in the practice of the present invention have the general formula:
  • each Ri, R 2 , R 3 , R 4 , and Rs are as described above, and each X is selected from those elements having an ionic charge of —2, in some embodiments each X is
  • m is 3, and one of the four organic radicals of a quat is a
  • the quaternary ammonium compounds used in the practice of the present invention can have the general formula:
  • each Ri, R 2 , R 3 , R 4 , Rs 5 and X are as described above. It should be noted that while in this embodiment R 2 and R 3 are shown as shared radicals, the shared radicals can be any of Ri, R2, R3, or R4.
  • the quats of the present invention can be prepared by any methods known in the art, exemplary methods include those described in commonly-owned co-pending applications
  • the quat(s) can be applied to the one or more articles directly, it is preferred to apply a prophylactic solution, more preferably an aqueous prophylactic solution, comprising the quaternary ammonium compound to the one or more articles.
  • the processes used in the production of quats typically produce quats in an aqueous solution.
  • the aqueous solution typically comprises water, at least one polar organic co-solvent, and one or more quats, as described herein.
  • Polar organic co-solvents present in these aqueous solutions typically have some compatibility with water since water is typically a component of the aqueous solution.
  • Polar organic co-solvents arc typically selected from several classes of compounds, such as: alcohols, such as methanol, ethanol, isopropyl alcohol, propanol, butanol, isobutyl alcohol, Ci — Ce alcohols, C 1 — C 4 alcohols, and the like, with methanol being a preferred example; polyalcohols, such as ethylene glycol, propylene glycol, and the like; esters, such as ethyl acetate, propyl acetate, formates, and the like; ethers, such as methyl tert-butyl ether, dioxane, glymes, and the like; and carbonyl-containing solvents, such as acetone, acetaldehyde, and the like. It should be noted that in some embodiments, only one polar organic co-solvent is used, and in other embodiments, more than one, sometimes two, or in other embodiments more that two, polar organic co-solvents arc used.
  • aqueous solutions generally have a polar organic co-solvent to water ratio in the range of from about 10:90 up to about 99:1 (wt. co-solvent: wt. water based on the combination of the water and polar organic co-solvent), and the exact amount of the polar organic co-solvent and water is selected according to the selection of Ri, R 2 , R3 and R 4 .
  • the ratio of co-solvent : water, by weight and on the same basis is within the range of from about 50:50 to about 99:1, about 60:40 to about 99:1 is more preferred, about 70:30 to about 98:2 is even more preferred, and about 80:20 to about 95:5 is yet more preferred.
  • aqueous solutions having a higher ratio of co-solvent to water are preferred for quats containing very hydrophobic alkyl substituent groups, e.g., double tailed or twin tailed quats where the alkyl groups are Ci 0 - C20, for example, while aqueous solutions having a lower ratio of co-solvent to water are preferred for boron-quats having less hydrophobic alkyl substituent groups, e.g., a (C2 - Ce) alkyltrimethylammonium salt.
  • the aqueous solutions can contain as the polar organic co-solvent an alcohol, and thus, the aqueous solution comprises a mixture of alcohol and water.
  • the aqueous solution comprises a mixture of a Ci - Ce alcohol and water in a ratio of from 10:90 to 99:1, by weight, on the same basis as above.
  • an aqueous solution that comprises a mixture of a Ci - C 4 alcohol and water in a ratio of from about 50:50 to about 99:1, about 60:40 to about 99:1 is more preferred, about 70:30 to about 98:2 is even more preferred, and about 80:20 to about 95:5 is yet more preferred, all by weight and on the same basis.
  • a preferred aqueous solution used in the production of quat(s) is a mixture of methanol and water in a ratio of about 85:15, by weight, based on the water and alcohol.
  • the aqueous solutions can comprise water, at least one polar organic co-solvent and the quat(s).
  • these ratios were based on the amount of polar organic co-solvent and water.
  • the mixture is a ternary composition comprising at least three major components, water, polar organic co-solvent, and the quat(s) "salt".
  • the ratio of the components of the aqueous solution can be represented as a ratio of wt. quat: wt. polar organic co-solvent: wt.
  • aqueous solution formed by adding 25% by weight of a quat salt to a mixture comprising an 85:15 by weight mixture of methanol: water, would have a ternary composition, by weight, of 25:64:11, quat salt: methanol: water by weight, based on the aqueous solution.
  • these aqueous solutions generally have a concentration of quat(s) ranging from about 1 to about 50 wt.% quat, based on the aqueous solution.
  • the aqueous solution can be applied to substrates as is, but these aqueous solutions are generally only available with quat concentrations in the range of from about 10 to about 30 wt.%, based on the aqueous solution, of the quat(s), more typically in the range of from about 20 to about 30wt.%, on the same basis.
  • the inventors hereof have discovered that quat(s) concentrations this high are not necessary for providing the desired characteristics to the one or more articles to which they are applied and ranges much lower are effective and less costly.
  • a diluent can be added to the aqueous solution to form a prophylactic solution, obviously comprising the diluent and the same components as the aqueous solution, having a quat concentration in the range of from about 1 to about 10 wt.%, in some embodiments in the range of from about 2 to about 8 wt.%, and in some embodiments in the range of about 4 to about 6 wt.%, all based on the prophylactic solution.
  • Diluents suitable for use herein can be selected from polar organic co-solvents, as described above, water, and mixtures thereof. In some embodiments, the diluent is water.
  • quaternary ammonium compound(s) having the formula below can be used:
  • Rj, R 2 , R 4 , Rs, X, and m are as described above
  • R' is a hydrocarbon group having from 1-10 carbon atoms, in some embodiments in the range of from 1 to 5, in some embodiments in the range of from 1 to 3, and R" and R'" are independently selected from z) substituted or unsubstitutcd alkyl groups or if) substituted or unsubstitutcd alkcnyl groups, wherein if z) or U) is substituted, they have one or more substituent groups selected from aryl, heterocyclyl, hydroxyl, ester, benzyl, carboxyl, halo, nitro, cyano, alkoxy or oxo groups.
  • R" and R'" are selected from unsubstituted alkyl groups having in the range of from 1 to 20 carbon atoms, in some embodiments in the range of from 1 to 15, and in other embodiments in the range of from 6 to 14.
  • the at least one quaternary ammonium compound, aqueous solution or prophylactic solution in some embodiments an aqueous solution, in other embodiments an aqueous prophylactic solution, can be applied to the one or more article(s) during any stage of the construction of the building. For instance, they can be applied to the concrete slab when it is complete, to the wall studs as they are put in place, the ceiling joists as they are put in place, the sheet-rock as it is hung, the ceiling tiles as they are in put in place, etc.
  • the prophylactic solution is applied to the one or more article(s) after the building has been completed.
  • the prophylactic or aqueous solution is applied to the wall studs, and/or cement, and/or ceiling joists, and/or wood roofing material before they are covered with other materials, i.e. roofing shingles, etc.
  • the prophylactic or aqueous solution can also be applied to other articles such as sheet rock or wall-boards such as paneling, bricks, etc. It is also contemplated that the prophylactic or aqueous solutions containing different quats can be used to achieve desired results.
  • the at least one quaternary ammonium compound is applied to one, sometimes more than one, sometimes all of the surfaces of the one or more articlc(s).
  • the method by which the at least one quaternary ammonium compound, aqueous solution or prophylactic solution it is applied to the one or more articles is not critical to the present invention.
  • suitable application methods include coating, dipping, soaking, brushing, spraying, and the like.
  • the quaternary ammonium compound is applied through spraying, in some embodiments with a pressure spraying device such as a pressure washer or pressurized spraying system, e.g. a garden sprayer pressurized by hand pumping.
  • a pressure spraying device such as a pressure washer or pressurized spraying system, e.g. a garden sprayer pressurized by hand pumping.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne l'utilisation de compositions d'ammonium quaternaire dans la prévention de la prolifération microbienne telle que la moisissure, les champignons et le mildiou dans une construction nouvelle et/ou existante.
PCT/US2007/060240 2006-12-20 2007-01-08 Utilisation de bétaïnes d'ammonium quaternaire dans la prévention de la moisissure, du mildiou et des champignons dans une construction nouvelle et/ou existante Ceased WO2008079417A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61382106A 2006-12-20 2006-12-20
US11/613,821 2006-12-20

Publications (2)

Publication Number Publication Date
WO2008079417A2 true WO2008079417A2 (fr) 2008-07-03
WO2008079417A3 WO2008079417A3 (fr) 2008-12-04

Family

ID=39467322

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/060240 Ceased WO2008079417A2 (fr) 2006-12-20 2007-01-08 Utilisation de bétaïnes d'ammonium quaternaire dans la prévention de la moisissure, du mildiou et des champignons dans une construction nouvelle et/ou existante

Country Status (1)

Country Link
WO (1) WO2008079417A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111978000A (zh) * 2020-09-12 2020-11-24 绵阳职业技术学院 一种磷石膏制品用防霉剂及其制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2976307A (en) * 1959-11-17 1961-03-21 Koppers Co Inc Ampholytic metal esters and the method of their preparation
ZA943999B (en) * 1993-06-09 1995-02-03 Lonza Ag Quaternary ammonium and waterproofing/preservative compositions
AU4374896A (en) * 1994-12-09 1996-06-26 Lonza Inc. Disinfecting use of quaternary ammonium carbonates
US20060257578A1 (en) * 2003-04-09 2006-11-16 Jun Zhang Micronized wood preservative formulations comprising boron compounds
CN1946674B (zh) * 2004-03-26 2010-09-01 雅宝公司 用于合成季铵化合物及其组合物的方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111978000A (zh) * 2020-09-12 2020-11-24 绵阳职业技术学院 一种磷石膏制品用防霉剂及其制备方法

Also Published As

Publication number Publication date
WO2008079417A3 (fr) 2008-12-04

Similar Documents

Publication Publication Date Title
EP1863865B1 (fr) Procede de creation d'un agent antimicrobien a base d'ammonium quaternaire contenant du silicium, polymere, sans solvant, presentant des proprietes antimicrobiennes prolongees superieures
CA2934554C (fr) Dispersions aqueuses pour une utilisation en tant que revetements avec cotes variables de permeabilite a la vapeur d'eau
EP3069778B1 (fr) Composition d'élimination d'aldéhydes d'air
WO2008079419A2 (fr) Composés d'ammonium quaternaires à nouveau mode d'action pour protéger des structures en bois
JPWO2011062259A1 (ja) 組成物、抗菌性処理剤及び抗菌性成形品
CN1098301C (zh) 塑料材料、塑料制品以及制备塑料材料的方法
WO2008079417A2 (fr) Utilisation de bétaïnes d'ammonium quaternaire dans la prévention de la moisissure, du mildiou et des champignons dans une construction nouvelle et/ou existante
WO2008079418A2 (fr) Utilisation de composés d'ammonium quaternaires pour éliminer les moisissures, le mildiou et les champignons dans une nouvelle construction n et/ou dans une construction existante
US7932292B2 (en) Use of quaternary ammonium compounds in the remediation of mold, mildew, and funguses
US20060252849A1 (en) Antifungal compositions and methods for manufacturing mold resistant materials
US8568757B2 (en) Formulations employing anhydrous disinfectant
WO2008079416A1 (fr) Composés d'ammonium quaternaire, tels des bétaïnes, pour la protection de structures en bois
EP2183970A1 (fr) Procédé d'inhibition de moisissure et composition
WO2008076460A1 (fr) Compositions de borate d'ammonium quaternaire et solutions de protection de substrat contenant celles-ci
CN101687706A (zh) 抗微生物水泥粘接组合物、方法和制品
WO2008079415A2 (fr) Compositions de borate d'ammonium quaternaire et solutions de conservation de substrat les contenant
US20040187221A1 (en) Compositions and methods for inhibiting tannin release
KR20230066279A (ko) 항균 및 친환경성과 내마모성을 강화한 가구표면재 및 그 제조방법
JPS61284588A (ja) 家具、什器又は建具類の処理方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07710001

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07710001

Country of ref document: EP

Kind code of ref document: A2