WO2024102348A1 - Composition pour élimination d'agent d'étanchéité - Google Patents

Composition pour élimination d'agent d'étanchéité Download PDF

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Publication number
WO2024102348A1
WO2024102348A1 PCT/US2023/036909 US2023036909W WO2024102348A1 WO 2024102348 A1 WO2024102348 A1 WO 2024102348A1 US 2023036909 W US2023036909 W US 2023036909W WO 2024102348 A1 WO2024102348 A1 WO 2024102348A1
Authority
WO
WIPO (PCT)
Prior art keywords
sealant
pyrrolidone
composition
alkyl
removal composition
Prior art date
Application number
PCT/US2023/036909
Other languages
English (en)
Inventor
Donald Cooper
Matthew Rhodes
Jonathan A. LONG
Original Assignee
Illinois Tool Works Inc.
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
Priority claimed from US18/387,155 external-priority patent/US20240166917A1/en
Application filed by Illinois Tool Works Inc. filed Critical Illinois Tool Works Inc.
Publication of WO2024102348A1 publication Critical patent/WO2024102348A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43—Solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/18—Glass; Plastics

Definitions

  • Silicones and sulfur-containing polymers such as polysulfides and polythioethers are widely used in the aerospace, construction, and insulating-glass industries in a variety of applications that require solvent resistance, water-immersion resistance, shrink resistance, and substrate adhesion. Common substrates include glass, metal, and concrete. Exemplary uses include liquid storage coatings and gaskets.
  • Polysulfides are typically created through the cure of bis(chloroethyl)formal, sodium polysulfide, and a small amount of trivalent crosslinking agent. The cure product is digested to form a thiol-terminated prepolymer that is oxidation cured to yield a polysulfide sealant.
  • solvents for removing uncured or partially cured silicones and sulfur- containing polymers have included: citrus-based solvent systems, such as d-limonene; volatile ketones, such as those including at least one of methyl ethyl ketone, methyl propyl ketone, or acetone; petroleum solvent-based such as those including at least one of mineral spirits, naphthenic, and paraffinic distillates.
  • citrus-based solvent systems such as d-limonene
  • volatile ketones such as those including at least one of methyl ethyl ketone, methyl propyl ketone, or acetone
  • petroleum solvent-based such as those including at least one of mineral spirits, naphthenic, and paraffinic distillates.
  • a fundamental problem of these conventional solvents is that while a low molecular weight solvent molecule is well-suited for penetration into the sealant composition, low molecular weight is associated with high vapor pressure and thus faster evaporation rates.
  • Conventional solvents also tend to have low flashpoint
  • a sealant removal composition provided that includes a pyrrolidone solvent, a non-ionic surfactant, and at least one co-solvent.
  • the composition is well suited to removal sulfur-based polymer and silicone-based polymer sealant.
  • a process of removing a sealant from a substrate includes applying the composition to the sealant. After allowing dwell time for the sealant to swell on the substrate, the sealant is removed.
  • the present invention has utility as a solvent composition for sealant removal that includes a synergistic combination of solvents and a surfactant to achieve efficient removal of sulfur-based polymer and silicone-based polymer sealant, regardless of the extent of sealant cure.
  • the solvent composition achieves this result in some inventive embodiments without resort to flammable or VOC solvents as defined in GHS Revision 3 (adopted by OSHA in 2012).
  • the present invention 70790-WO-ITW-0262PCT affords sealant removal properties with better human health and environmental properties compared to conventional sealant removers.
  • the present invention is believed to include a nonionic surfactant that promotes sealant penetration and solvent swell of the sealant, even when fully cured.
  • a nonionic surfactant that promotes sealant penetration and solvent swell of the sealant, even when fully cured.
  • the present invention includes a propellant, a thickener, or a combination thereof for specialized uses.
  • the range is intended to encompass not only the end point values of the range but also intermediate values of the range as explicitly being included within the range and varying by the last significant figure of the range.
  • a recited range of from 1 to 4 is intended to include 1-2, 1-3, 2- 4, 3-4, and 1-4.
  • Typical and preferred sealant removing compositions according to the present inventions are provided in the Table. [0021] Table. Inventive Sealant Removal Composition (amounts in total weight percent unless otherwise noted). Ingredient Typical Preferred Pyrrolidone solvent 5-45 15-35 Non-ionic surfactant(s) 10-40 17-35 [0022] An inventive sealant removal composition includes a pyrrolidone solvent, synonymously referred to a lactam solvent.
  • a pyrrolidone operative herein has the cyclic structure (I): R 2 -NCHR 1 -CHR-CH 2 C(O) (I) where R 1 is hydrogen, or C 1 -C 3 linear alkyl; R 2 is hydrogen, C 1 -C 12 linear alkyl, C 1 -C 12 branched alkyl, C 5 -C 12 cyclic alkyl, or C 1 -C 12 linear alkoxy; and R is hydrogen, or -C 6 R 3 5 ; where R 3 in each occurrence is independently hydrogen, -C6H5, and substituted C6 aryl with one or more hydrogen substituted by C 1 -C 12 linear alkyl, C 1 -C 12 branched alkyl, or C 5 -C 12 cyclic alkyl.
  • pyrrolidones operative herein illustratively include pyrrolidone, N-methyl-2-pyrrolidone, N-ethyl- 2-pyrrolidone, N-n-butyl-2-pyrrolidone, N-tert-butyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N-n-butylpyrrolidone, N-isobutylpyrrolidone, N-t-butylpyrrolidone, N-n-pentylpyrrolidone, N- (methyl-substituted butyl)pyrrolidones, phenyl-methyl-substituted N-propylpyrrolidone, phenyl- methyl-substituted N-butyl pyrrolidone, N-(methoxypropyl)pyrrolidone, 1,5-dimethyl- 70790-WO-ITW-0262PCT pyr
  • N-methyl-2-pyrrolidone is classified by the European Chemicals Agency as a “Substance of Very High Concern” and while operative herein is readily substituted in an inventive composition in all or part by other of the pyrrolidones (I).
  • Non-ionic surfactants operative herein in some inventive embodiments have hydrophile/lipophile balance (HLB) values between 8 and 13.
  • Classes of non-ionic surfactants operative herein include C 9 -C 24 fatty acid esters, C 12 -C 24 fatty alcohol ethers, C 10 -C 24 amine oxides, nonylphenol ethoxylate, alkyl polyglucosides with C8-C16 alkyl chain, each alone or any of the aforementioned in combination.
  • Alcohol alkoxylates operative herein have the general formula (II): where R is C4-C22 linear has a value of from 2 to 20; y has a value of from 0 to 15, or the general formula (III): RO–(CH2CH2O)n–H (III) where n is average moles of ethylene oxide (EO) and R is a C 9 -C 18 alkyl.
  • Specific non-ionic surfactants operative herein illustratively include alcohol C 12 -C 15 ethoxylated propoxylated, C12-C14, ethoxylated, C9-11 ethoxylated alcohols having EO values from 70790-WO-ITW-0262PCT 2.5 – 9, or combinations thereof.
  • EO 2.5 C 9-11 ethoxylated alcohol is used in combination with one or more EO 6-9 C9-11 ethoxylated alcohols.
  • Still other non-ionic surfactants operative herein include mixed ethylene oxide propylene oxide block copolymers, room temperature liquid polyethylene glycols, ethylene glycol monoesters, ethoxylated dibenzylphenol, amine oxides alkyl sugar esters such as alkyl sucrose esters and alkyl oligosaccharide esters, alkyl capped polyvinyl alcohol and alkyl capped polyvinyl pyrrolidone.
  • non-ionic surfactants are present with HLB values that vary from one another.
  • a first non-ionic surfactant has a first surfactant HLB value of between 6 and 9 total weight percent
  • a second non-ionic surfactant has a second surfactant HLB value of between 12 and 16.
  • Typical loadings of all non-ionic surfactants present in an inventive composition range from 10 to 40 total weight percent and in specific embodiments between 20 and 30 total weight percent.
  • a particularly suitable surfactant combination may contain a ratio of first non-ionic surfactant to second non-ionic surfactant ranging between 0.4-2 :1.
  • a co-solvent or blend of co-solvents improves the sealant removal properties of an inventive composition.
  • the composition excludes the conventional solvents of citrus terpenes, such as d-limonene; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, mesityl oxide, and isophorone; and petroleum distillates to achieve higher flash points of > 70oC and better handling property compositions.
  • Typical loadings of all co-solvents present in an inventive composition range from 60 to 90 total weight percent and in specific embodiments between 70 and 80 total weight percent.
  • One class of co-solvent according to the present invention include polyalkoxys that are glymes, polyethers, or a combination thereof.
  • a glyme operative herein has the structure (IV): R-(OCHR 1 CHR 1 ) n -OR (IV) where R in each occurrence is independently C1-C3 linear alkyl; R 1 in each occurrence is independently C1-C3 linear alkyl and n is an integer value between 1 and 10.
  • a polyether operative herein has the structure (V): R[-(O-R 1 -O-R 2 -] n (V) where R is C1-C12 linear alkyl; R 1 in each occurrence is independently C1-C12 linear alkyl, C1-C12 branched alkyl, C 5 -C 12 cyclic alkyl; R 2 in each occurrence is independently C 1 -C 12 linear alkyl, C1-C12 branched alkyl, C5-C12 cyclic alkyl; and n is an integer value between 1 and 50.
  • Cyclic forms of the aforementioned are also operative herein.
  • Specific polyethers operative herein include tetraoxaundecane, 1,3-dioxacyclopentane, 5-hydroxy-1,3-dioxane , 4-hydroxymethyl-1,3- dioxolane , tetrahydrofurfuryl alcohol, and mixtures of any of the aforementioned.
  • Polyalkoxy co- solvent is typically being present from 10 to 30 total weight percent and in specific embodiments between 15 to 25 total weight percent.
  • Other suitable co-solvents operative herein are acetals.
  • acetals operative herein illustratively include diethoxymethane, dimethoxymethane, 1,3-dioxolane and mixtures of any of the aforementioned.
  • Acetal co-solvent is typically being present from 10 to 30 total weight percent and in specific embodiments between 15 and 25 total weight percent.
  • Other suitable co-solvents operative herein are amides.
  • Specific amides operative herein illustratively include N,N-dimethyl formamide, acetamide, N,N-dimethyl acetamide, N,N-dimethylcapryilamide, N,N-dimethyloctanamide, N,N- dimethyldecanamide, and mixtures of any of the aforementioned.
  • Amide co-solvent is typically being present from 10 to 40 total weight percent and in specific embodiments between 20 and 30 total weight percent.
  • Wetting agents operative herein illustratively include branched secondary alcohol ethoxylate, 8-11 EO, sulfo-succinamates that illustratively include disodium N-octadecylsulfo-succinamate; tetrasodium N-(1,2- dicarboxyethyl)-N-octadecylsulfo-succinamate; diamyl ester of sodium sulfosuccinic acid; dihexyl ester of sodium sulfosuccinic acid; and dioctyl esters of sodium sulfosuccinic acid; dihexyl ester of sodium sulfosuccinic acid; and dioctyl esters of sodium sulfosuccinic acid; castor
  • the function of the wetting agent is to spread the composition onto and to penetrate the sealant.
  • the wetting agent is typically being present from 0 to 15 total weight percent and in specific embodiments between 5 and 10 total weight percent.
  • Other additives present in certain embodiments of an inventive composition illustratively include solubilizing agents, dyes, fragrances, thickeners, water, and combinations thereof. Each additive is independently present from 0 to 5 total weight percent and in specific embodiments between 0.5 and 3 total weight percent.
  • a solubilizing agent is a surfactant present to promote the dispersion of one of the other additives.
  • the solubilizing agent can be one of the aforementioned non-ionic surfactants, and in such instances is counted as part of the amount of non-ionic surfactant.
  • Monoethanolamine is exemplary of solubilizing agent operative herein.
  • a dye is typically being present from 0 and 5 total weight percent and in specific embodiments between 0 and 1 total weight percent.
  • the fragrance is typically being present from 0 and 5 total weight percent and in specific embodiments between 0 and 1 total weight percent.
  • a dye operative herein illustratively includes a fluorescent tracer dye. The dye is typically being present from 0 and 1 total weight percent and in specific embodiments between 0 and 0.25 total weight percent.
  • a thickener operative herein illustratively includes cellulosic thickeners.
  • the thickener is typically being present from 0 and 5 total weight percent and in specific embodiments between 0 and 1 total weight percent. 70790-WO-ITW-0262PCT [0038] It is appreciated that an inventive solvent composition is readily provided in an aerosol container having a volume and an aperture.
  • the container is formed from a material that is compatible with the inventive composition and includes a container wall or at least liner contacting the volume in which the solvent resides that is illustratively formed from metals such as tin plated steel, aluminum; glass; or polymer coated steel.
  • a spray nozzle is provided to selectively seal the aperture.
  • a one piece valve is preassembled with the valve cup, dip tube, and actuator, can as unitary assembly, and prior to pressure-filling.
  • the propellant is one conventional to the field and compatible with the composition.
  • Propellants operative herein illustratively include is carbon dioxide, nitrogen, halocarbons, butane, isobutane, propane, or dimethyl ether.
  • the propellant, if present. is present in an amount of from 1 to 5 weight percent of the inventive composition.
  • the propellant is not included in the total amounts of the present invention provided in the Table.
  • an inventive composition for removal of sulfur-containing polymer sealants or silicone sealants commonly used in the aerospace, automotive, construction, and insulating-glass industries includes applying the composition directly to the sealant.
  • an inventive composition is effective in removal of uncured, partially cured, and fully cured sealants.
  • the sealant remover composition is readily applied by any conventional technique. For example, a sealant material can be dipped or soaked in a tank containing the inventive sealant remover composition. If desired, the sealant remover can be sprayed, brushed, or rolled onto the surface.
  • Normally, exposing the sealant to an inventive composition for from 30 to 120 minutes hours is effective to swell and otherwise promote removal of the sealant.
  • the sealant substrate can be metal, including aluminum and steel, glass, concrete, all of which are not damaged by an 70790-WO-ITW-0262PCT inventive composition removing a sealant therefrom. Manually applied pressure transmitted via a cloth or scrapping blade is used in some instances to removal softened sealant. The process of application of the inventive composition is readily repeated as needed.
  • the following examples merely illustrate the invention. Those skilled in the art will recognize many variations that are within the spirit of the invention and scope of the claims.
  • Example 1 [0043] Aluminum 2024-T3 panels (4 x 6 in) are prepared and coated with an aerospace grade epoxy primer per manufacturer’s specification. The primed tested panels are allowed to fully cure for 168 hours at 25° C prior to application of the sealant.
  • test panels are coated with the Polysulfide sealant in strips 6-8 mm wide and to a thickness of 6 mm; multiple strips are applied to the surface of a test panel for evaluation. Faring the edges along the test strips improves adhesion properties for testing purposes and is a common practice for an in-field application.
  • the sealant is cured for at 168 hours at 25° C. Sealant remover is applied to the sealant surface in an amount to fully coat the test sealant strip. The sealant remover remains on the surface until the sealant is sufficiently softened to be manually removed with a plastic scraper. [0045] Lift times are noted when the sealant is completely removed from the coupon.
  • Example 2 An inventive sealant removal composition is formed with 20 total weight percent of 1- butylpyrrolidin-2-one; co-solvent of 25 total weight percent of equal weight amounts of N,N- dimethyloctanamide and N,N-dimethyldecanamide; and 25 total weight percent of tetraoxaundecane; 18 total weight percent of nonionic alkoxylated alcohol with an HLB of 12; 12 70790-WO-ITW-0262PCT total weight percent of nonionic alkoxylated alcohol with an HLB of 6.
  • the resulting composition has very low odor profile and no irritating fumes in confined spaces or enclosed work areas.
  • Example 3 The composition of Example 2 is tested and found to have a flashpoint > 70 oC as measured by per ASTM D3278-96 (2011), both as normalized to standard temperature and pressure (STP). It is noted that the resulting slow evaporation increases contact (dwell time) thereby reducing the need for re-application. An inventive composition is considered by as combustible versus flammable.
  • Example 4 [0048] The coupons of Example 1 are exposed to the composition of Example 2. The composition of Example 2 is noted to remove more than 95% of the sealant with a lift time of less than 60 minutes.
  • Methyl ethyl ketone (MEK), and monoethylene glycol have a limited ability to remove uncured (4 hours after mixing) PPG PR-1776M class B polysulfide, but are unable to remove the cured sealant.
  • 50% N—methyl-2-pyrrolidone in aromatic hydrocarbons is used to remove PPG PR- 1776M class B polysulfide provided the majority, but not all of the sealant compared to Example 4, a partial lift time of more than 100 minutes is noted.
  • Example 5 [PLEASE SEE US 5,561,215; TABLE 2 for basis] 70790-WO-ITW-0262PCT Example 5 [0051] The coupons of Example 1 are reproduced with a like thickness of commercially available polythioether sealant and cured per Example 1. The composition of Example 2 is effective to remove the sealant. [0052] Patents and publications mention the specification are indicative of the levels of those skilled in the art to which the invention pertains. These patents and publications are incorporated herein by reference to the same extent as if each individual patent or publication was specifically and individually incorporated herein by reference. [0053] The forgoing description is illustrative of particular embodiments of the invention but is not meant to be a limitation upon the practice thereof. The following claims, including all equivalents thereof are intended to define the scope of the invention.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Sealing Material Composition (AREA)

Abstract

L'invention concerne une composition utilisée pour l'élimination d'agent d'étanchéité, comprenant un solvant pyrrolidone, un tensioactif non ionique et au moins un co-solvant. La composition est bien adaptée à l'élimination d'agent d'étanchéité polymère à base de soufre et polymère à base de silicone. L'invention concerne également un procédé d'élimination d'un agent d'étanchéité sur un substrat, qui comprend l'application de la composition sur l'agent d'étanchéité. Après avoir laissé un temps de pose permettant à l'agent d'étanchéité de gonfler sur le substrat, l'agent d'étanchéité est éliminé.
PCT/US2023/036909 2022-11-09 2023-11-07 Composition pour élimination d'agent d'étanchéité WO2024102348A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US202263423827P 2022-11-09 2022-11-09
US63/423,827 2022-11-09
US18/387,155 US20240166917A1 (en) 2022-11-09 2023-11-06 Sealant remover
US18/387,155 2023-11-06

Publications (1)

Publication Number Publication Date
WO2024102348A1 true WO2024102348A1 (fr) 2024-05-16

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991003522A1 (fr) * 1989-08-30 1991-03-21 Leys Cassius W Nettoyeur pour le traitement d'une surface
US5561215A (en) 1994-08-31 1996-10-01 Arco Chemical Technology, L.P. Pyrrolidones for cleanup of sulfur-containing polymers
US5954890A (en) * 1995-10-27 1999-09-21 Eldorado Chemical Co., Inc. Compositions and methods for coating removal
WO2012021824A2 (fr) * 2010-08-12 2012-02-16 Segetis, Inc. Compositions d'élimination à base de carboxy ester cétal, procédés de fabrication et utilisations associées
WO2013107822A1 (fr) * 2012-01-17 2013-07-25 Taminco Utilisation de solvants améliorés de type n-alkyl-pyrrolidone
US8957007B2 (en) * 2011-08-17 2015-02-17 John Cleaon Moorre Aluminum safe compositions for removing cured polysulfide resins
CN114426909A (zh) * 2022-02-22 2022-05-03 伊利诺斯工具制品有限公司 一种积碳清洗方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991003522A1 (fr) * 1989-08-30 1991-03-21 Leys Cassius W Nettoyeur pour le traitement d'une surface
US5561215A (en) 1994-08-31 1996-10-01 Arco Chemical Technology, L.P. Pyrrolidones for cleanup of sulfur-containing polymers
US5954890A (en) * 1995-10-27 1999-09-21 Eldorado Chemical Co., Inc. Compositions and methods for coating removal
WO2012021824A2 (fr) * 2010-08-12 2012-02-16 Segetis, Inc. Compositions d'élimination à base de carboxy ester cétal, procédés de fabrication et utilisations associées
US8957007B2 (en) * 2011-08-17 2015-02-17 John Cleaon Moorre Aluminum safe compositions for removing cured polysulfide resins
WO2013107822A1 (fr) * 2012-01-17 2013-07-25 Taminco Utilisation de solvants améliorés de type n-alkyl-pyrrolidone
CN114426909A (zh) * 2022-02-22 2022-05-03 伊利诺斯工具制品有限公司 一种积碳清洗方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J.P. HILTON-PROCTOR ET AL.: "Substituted 1-methyl-4-phenylpyrrolidin-2-ones - Fragment-based design of N-methylpyrrolidone-derived bromodomain inhibitors", EUR. J. MED. CHEM., vol. 191, no. 1, 2020, pages 112120, XP086086462, DOI: 10.1016/j.ejmech.2020.112120

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