+

WO2003062325A2 - Compositions decapantes pour revetements et leur utilisation - Google Patents

Compositions decapantes pour revetements et leur utilisation Download PDF

Info

Publication number
WO2003062325A2
WO2003062325A2 PCT/US2003/001719 US0301719W WO03062325A2 WO 2003062325 A2 WO2003062325 A2 WO 2003062325A2 US 0301719 W US0301719 W US 0301719W WO 03062325 A2 WO03062325 A2 WO 03062325A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
additional component
carbonate
composition
methyl
Prior art date
Application number
PCT/US2003/001719
Other languages
English (en)
Other versions
WO2003062325A3 (fr
Inventor
James R. Machac, Jr.
Edward T. Marquis
Susan A. Woodrum
Katty Darragas
Original Assignee
Huntsman Petrochemical Corporation
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 Huntsman Petrochemical Corporation filed Critical Huntsman Petrochemical Corporation
Priority to AU2003209305A priority Critical patent/AU2003209305A1/en
Publication of WO2003062325A2 publication Critical patent/WO2003062325A2/fr
Publication of WO2003062325A3 publication Critical patent/WO2003062325A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D9/00—Chemical paint or ink removers
    • C09D9/005—Chemical paint or ink removers containing organic solvents

Definitions

  • This invention relates to compositions for paint and coating removal from various surfaces, including woods or metals. More particularly, this invention relates to compositions containing a carbonate such as alkylene carbonate or dialkyl carbonate or both, in combination with l-methyl-2-pyrrolidone, and containing at least one additional component selected from the group consisting of: dibasic esters, mono-esters, organic sulfur compounds, ethers, and ketones. Paint removing compositions are commonly used in industry, such as for stripping paint from aircraft fuselages. Conventional paint remover compositions include methylene chloride, phenol, or caustics. Each of these materials, however, has inherent problems associated with their use.
  • methylene chloride based compositions are very effective as paint removers
  • methylene chloride is a highly volatile material which is considered toxic.
  • phenol is highly toxic.
  • caustic causes burns and attacks aluminum. Due to the deficiencies and disadvantages of conventional paint removing compositions, new paint removing compositions are highly desirable.
  • the invention provides a solution to one or more of the problems and disadvantages discussed above.
  • this invention is a composition useful as a paint remover, comprising: a carbonate, l-methyl-2-pyrrolidone, and at least one additional component selected from the group consisting of: dibasic esters, mono-esters, organic sulfur compounds, ethers, and ketones.
  • this invention is a process for removing paint, comprising: applying a composition to a painted surface for a time and under conditions effective to cause blistering or bubbling of the paint, wherein the composition comprises a carbonate, l-methyl-2-pyrrolidone, and at least one additional component selected from the group consisting of: dibasic esters, mono-esters, organic sulfur compounds, ethers, and ketones.
  • this invention is a process for removing a coating from a surface, comprising: providing a composition containing a a carbonate, l-methyl-2- pyrrolidone, and at least one additional component selected from the group consisting of: dibasic esters, mono-esters, organic sulfur compounds, ethers, and ketones; adding a thickening agent to the composition and mixing the resulting composition to form a thickened composition; applying the thickened composition to a coated surface for a time sufficient and under conditions effective to separate at least a portion of the coating from the surface; and removing the coating and thickened composition from the surface.
  • this invention is a process of the manufacture of a paint stripper, comprising: combining a a carbonate, l-methyl-2-pyrrolidone, and at least one additional component selected from the group consisting of: dibasic esters, mono-esters, organic sulfur compounds, ethers, and ketones in amounts and under conditions effective to form a homogeneous composition.
  • the combining of the components may be effected as by stirring, typically at the ambient atmospheric pressure and temperature.
  • the composition may include additional components as disclosed herein.
  • the surfaces to be treated may be sealed with a variety of sealants, such as polysulfide, polyurethane, lacquer, epoxy, and the like.
  • the compositions can be used to remove paints and coatings from furniture, automobiles, boats, trains, airplanes, military vehicles, and so forth.
  • the compositions have several important attributes, including low toxicity, and high efficacy in removing paint and coatings. It has further been advantageously found that the compositions may be blended with additional co-solvents, activators, corrosion inhibitors, and the like, or may be used directly to effect paint removal. Furthermore, in the case of propylene carbonate, the propylene carbonate breaks down into propylene glycol, which is non-toxic. Hence, the propylene carbonate compositions of this invention are for the most part environmentally friendly, particularly as compared to chlorinated hydrocarbons and the like which are commonly used for paint and coating removing. The compositions of this invention may advantageously be of low volatility and free of carcinogenic chemicals.
  • compositions of this invention contain a carbonate such as alkylene carbonate or dialkyl carbonate or both, dibasic ester and a mono-ester.
  • the carbonates that may be employed in the practice of this invention are organic carbonates and include alkylene carbonates and dialkyl carbonates.
  • the alkylene carbonate used in the present invention can contain from 2 to 10 carbon atoms.
  • Representative examples of alkylene carbonates that may be employed in the practice of this invention include ethylene carbonate and propylene carbonate. Mixtures of carbonates may also be employed.
  • alkylene carbonates are preferred, and among the alkylene carbonates propylene carbonate is preferred.
  • the dialkyl carbonate used in the present invention may contain from 3 to 25 carbon atoms.
  • the dialkyl carbonate may be of formula R ⁇ CO 3 ⁇ R', wherein R and R' may be the same or different, and may independently in each occurrence be alkyl of from 1 to about 12 carbon atoms.
  • the dialkyl carbonate may be dimethyl carbonate, diethyl carbonate, or a mixture thereof.
  • the amount of alkylene carbonate, dialkyl carbonate or both used in the practice of this invention may vary widely. Typically the total amount of carbonate is from about 0.1 to about 90 percent by weight of the total composition. In one embodiment, the amount is from about 10 to about 50 percent by weight, preferably from about 15 to about 25 percent by weight.
  • the DBE used in this invention include aliphatic diesters having a molecular weight of up to about 200. DBE has the advantage of being considered to be safe and of low toxicity. More than one dibasic ester can be used in the present compositions. DBE is a well known material and is currently available commercially. In general, the DBE used in this invention may be described as being a Ci to C 6 dialkyl ester of a C 2 to C M aliphatic di-acid, and particularly a Ci to C dialkyl ester of a C 2 to C 6 aliphatic di-acid.
  • the DBE used in the practice of this invention may be derived from various di-acids such as from adipic acid, glutaric acid and succinic acid.
  • the amount of DBE used in the practice of this invention may vary widely. In general, the amount of DBE may be from about 0.1 percent by weight to about 90 percent by weight, more typically in the range from about 5 to about 50 percent by weight. In one embodiment of this invention, the DBE is present in an amount in the range from 15 to about 45 percent by weight of the total composition, preferably from about 20 to about 45 percent.
  • the amount of NMP (l-methyl-2-pyrrolidone) used in the practice of this invention may vary widely.
  • the amount of NMP may be from about 0.1 percent by weight to about 90 percent by weight, more typically in the range from about 5 to about 50 percent by weight. In one embodiment of this invention, the NMP is present in an amount in the range from 15 to about 45 percent by weight of the total composition, preferably from about 20 to about 45 percent.
  • the mono-esters that may employed in the practice of this invention may vary widely.
  • the mono-esters that may be used in the practice of this invention typically contain up to about 20 carbon atoms per molecule.
  • the mono-esters may include other functional groups in the compound.
  • the mono-esters may also include ether groups, such as methyl, propyl or butyl ether groups.
  • cyclic esters such as butyrolactone may be employed in the practice of this invention.
  • Preferred mono-esters include an ether group.
  • Ethyl-3-ethoxy-propionate (“EEP") is a representative preferred mono-ester which is considered to be safe and of low toxicity.
  • the amount of mono-ester used in the practice of this invention may vary widely. Typically the amount is from about 0.1 to about 90 percent by weight of the total composition. In one embodiment, the amount is from about 5 to about 50 percent, preferably from about 15 to about 45 percent, and more preferably from about 20 to about 40 percent.
  • the organic sulfur-containing compounds that may employed in the practice of this invention may vary widely.
  • the organic sulfur-containing compounds that may be used in the practice of this invention typically contain up to about 20 carbons.
  • the organic sulfur-containing compounds may include other functional groups in the compound.
  • Representative examples of sulfur-containing compounds that may be employed in the practice of this invention include dimethylsulfoxide (DMSO) and sulfolane.
  • DMSO dimethylsulfoxide
  • DMSO for instance, is considered to be safe and of low toxicity.
  • the amount of organic sulfur-containing compound used in the practice of this invention may vary widely. Typically the total amount of organic sulfur-containing compound is from about 0.1 to about 50 percent by weight of the total composition. In one embodiment, the amount is from about 5 to about 40 percent by weight, preferably from about 10 to about 30 percent by weight.
  • the ketones that may be employed in the practice of this invention may vary widely.
  • the ketones that may be used in the practice of this invention typically contain up to about 20 carbon atoms per molecule and are typically aliphatic compounds.
  • the ketones may include other functional groups in the compound.
  • Representative non- limiting examples of ketones that may be used in the practice of this invention include acetone, methyl ethyl ketone (MEK), 5-methyl-2-hexanone (MIAK), methyl isobutyl ketone and diethyl ketone.
  • MEK methyl ethyl ketone
  • MIAK 5-methyl-2-hexanone
  • the amount of ketone used in the practice of this invention may vary widely. Typically the total amount of ketone is from about 0.1 to about 50 percent by weight of the total composition.
  • the amount is from about 5 to about 20 percent by weight, preferably from about 5 to about 15 percent by weight.
  • the glycol ethers that may employed in the practice of this invention may vary widely.
  • the glycol ethers that may be used in the practice of this invention typically contain up to about 20 carbons.
  • the glycol ethers may include other functional groups in the compound.
  • Representative non-limiting examples of useful glycol ethers include glycol ethers such as propylene glycol methyl ether (PM), dipropylene glycol methyl ether (DPM), or dipropylene glycol n-butyl ether (DPNB), ethylene glycol butyl ether (EB) and dipropylene glycol butyl ether (DB).
  • the amount of glycol ether used in the practice of this invention may vary widely. Typically the total amount of glycol ether is from about 0.1 to about 50 percent by weight of the total composition. In one embodiment, the amount is from about 5 to about 20 percent by weight, preferably from about 5 to about 15 percent by weight.
  • the compositions of this invention may optionally include an alcohol.
  • compositions of this invention contain from 0 to about 90 percent by weight alcohol. In certain embodiments of this invention, the compositions contain from about 10 to about 50 percent by weight of the carbonate, from about 15 to about 45 percent by weight of DBE, and from about 15 to about 45 percent of the mono-ester, with the percentages totaling 100.
  • compositions of this invention may optionally contain activators such as formic or oxalic acid, thickeners, surfactants, acids or bases, stabilizers, corrosion inhibitors, and other additives commonly used in paint removers.
  • activators such as formic or oxalic acid, thickeners, surfactants, acids or bases, stabilizers, corrosion inhibitors, and other additives commonly used in paint removers.
  • Non-limiting examples of representative thickeners include cellulose ethers such hydroxypropyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, methyl cellulose, and other alkyl or hydroxy alkyl cellulose; silica including colloidal silica; clays such as bentonite and montmorillonite starch; alumina including colloidal alumina; gum arabic; tragacanth; agar; sugar derivatives; high molecular weight polyethylene oxides; guar gum; xanthan gum; polyvinyl pyrrolidone and methyl vinyl ether/maleic anhydride copolymers. It has been found that certain hydroxy alkyl cellulose ethers and certain experimental polymers are particularly effective and resistant to breakdown in the practice of this invention. Such cellulose ethers are available commercially from The
  • the amount of such thickener can vary depending on the desired level of thickening for the given application. In general, the amount of thickener employed is about 1 to about 4 percent by weight.
  • Non-limiting examples of representative corrosion inhibitors include ethoxylated butynediol, petroleum sulfonates, blends of propargyl alcohol and thiourea. If used, the amount of such corrosion inhibitors is typically up to about 10% by weight of the total composition.
  • Non-limiting examples of representative surfactants which may optionally be used in the practice of this invention include non-ionic, anionic, cationic and amphoteric surfactants, such as monocarboxyl cocoimidoazoline, higher alkyl sulfate sodium salts, tridecyloxy ⁇ oly(alkyleneoxy ethanol), ethoxylated or propoxylated alkyl phenol, alkyl sulfoamides, C 10-18 alkaryl sulfonates such as alkylbenzene sulfonates, cocoamphaodipropionate, cetylpalmitic alkanol amides, hydrogenated castor oil, isooctylphenyl polyethoxy ethanol, sorbitan monopalmitate, C 8-18 alkyl pyrrolidone, cocoaminoprpionic acid and polyethoxy amino salts thereof.
  • the amount of surfactant should be sufficient to render the composition miscible. If used, the amount
  • compositions of this invention may also optionally contain a wide variety of other organic cosolvents.
  • the present invention may be practiced in the absence of one or more of such solvents.
  • Representative classes of such other cosolvents include hydrocarbons, ethers, phenols, glycols, lactones, chlorinated hydrocarbons, aromatic hydrocarbons nitrated hydrocarbons and amides.
  • Such cosolvents may be polar or non-polar, protic or aprotic, cyclic, branched, or straight- chain, and may contain one or more functional groups.
  • Representative examples of common hydrocarbon solvents include hexane, toluene, xylene, and mixtures of aliphatic and aromatic hydrocarbons.
  • Representative examples of common ether solvents include dibutyl ether, ethyl ether, and diphenyl ether.
  • Representative examples of common phenols include phenol and the cresols and resorcinols.
  • Representative examples of common glycol solvents include ethylene, propylene and butylene glycols as well as methyl propane diol.
  • Representative examples of common chlorinated hydrocarbon solvents include methylene chloride, methyl chloroform, chlorobenzenes and dichlorobenzenes.
  • Representative examples of common nitrated hydrocarbon solvents include nitroethane and nitropropane.
  • Representative examples of common amide solvents include formamide, dimethyl formamide, acetamide, and dimethylacetamide.
  • a co-solvent may be used to provide a miscible composition.
  • a glycol ether may be added as a co-solvent in an amount effective to solubilize the components of the mixture.
  • Such glycol ethers may be included for other purposes as well. Such amounts may vary depending on the specific composition of interest, as one of skill in the art may appreciate. The particular type and amount of glycol ether which will afford a miscible composition may be identified by routine experimentation.
  • an alcohol or alkylene carbonate may be beneficially employed as a co-solvent to provide miscible dialkyl carbonate compositions of this invention.
  • the conditions under which the paint stripping process of this invention may be practiced may vary. Typically, the process will be conducted under ambient atmospheric conditions. Temperatures from 0° F. to about 125°F, although higher temperatures may be used.
  • the paint remover composition may be applied by any convenient method such as by dipping, spraying, or brushing the composition onto the paint surface. For resistant painted surfaces it may be desirable to apply the composition two or more times to fully separate the paint from the surface. It may be desirable to use a rag, scraper, sand blaster, or the like to fully remove paint chips from the surface after the paint remover composition has been given time to fully act. Alternatively, high pressure water spray may be employed to remove paint chips and residual paint remover composition. It may be appreciated that the time required for the paint remover composition to act will vary due to a variety of factors such as temperature, paint type, and particular paint remover formulation being used. In general, application times are between one minute and one hour, although longer application times may be used.
  • PC denotes propylene carbonate
  • EC-50 denotes a 50/50 blend of propylene carbonate and ethylene carbonate
  • NMP denotes 1- methyl-2-pyrrolidone
  • DB denotes dipropylene glycol butyl ether
  • PM denotes propylene glycol monomethyl ether
  • EEP denotes ethyl-3-ethoxy propionate
  • thickener was Methocel® 311.
  • Table I below lists several formulations according to the present invention useful for removing acrylic paint from a wood substrate. After thoroughly mixing all components, a small amount of each composition was applied to a painted test panel such that an are about l A n in diameter was covered by the mixture.
  • the test panels used consisted of a wood substrate painted with 9 layers of acrylic paint. Each coat of paint was a different color such that the number of layers of paint removed by the mixture could easily be assessed at a given time simply by observing the color of the exposed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des compositions utiles pour enlever des revêtements à partir de divers substrats. Ces compositions contiennent un carbonate d'alkylène, un amide cyclique et un ou plusieurs constituants additionnels choisis dans le groupe constitué par des esters dibasiques, des monoesters, des composés sulfurés organiques, des éthers et des cétones.
PCT/US2003/001719 2002-01-22 2003-01-21 Compositions decapantes pour revetements et leur utilisation WO2003062325A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003209305A AU2003209305A1 (en) 2002-01-22 2003-01-21 Coating remover compositions and use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35086602P 2002-01-22 2002-01-22
US60/350,866 2002-01-22

Publications (2)

Publication Number Publication Date
WO2003062325A2 true WO2003062325A2 (fr) 2003-07-31
WO2003062325A3 WO2003062325A3 (fr) 2004-05-27

Family

ID=27613433

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/001719 WO2003062325A2 (fr) 2002-01-22 2003-01-21 Compositions decapantes pour revetements et leur utilisation

Country Status (2)

Country Link
AU (1) AU2003209305A1 (fr)
WO (1) WO2003062325A2 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019210183A1 (fr) * 2018-04-27 2019-10-31 W.M. Barr & Company, Inc. Décapant pour peinture présentant une inflammabilité réduite
US11708502B2 (en) 2017-06-20 2023-07-25 W.M. Barr & Company, Inc. Paint remover composition and method of making
US11827812B2 (en) 2017-06-20 2023-11-28 W.M. Barr & Company, Inc. Paint remover composition and method of making
US12012572B2 (en) 2017-10-09 2024-06-18 W.M. Barr & Company, Inc. Automotive paint remover composition and method of making
US12031061B2 (en) 2019-06-21 2024-07-09 W.M. Barr & Company, Inc. Paint remover
US12240998B1 (en) 2024-03-20 2025-03-04 W. M. Barr & Company, Inc. Paint remover compositions comprising tetrahydrofuran, alkanediol, and amine and methods of making and using the same
US12247139B1 (en) 2024-03-20 2025-03-11 W. M. Barr & Company, Inc. Paint remover compositions comprising tetrahydrofuran, alkanediol, and amine and methods of making and using the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5124062A (en) * 1989-06-30 1992-06-23 Stevens Sciences Corp. Paint stripper and varnish remover compositions, methods for making these compositions and methods for removing paint and other polymeric coatings from flexible and inflexible surfaces
US5334331A (en) * 1993-01-12 1994-08-02 Isp Investments Inc. Method of activating N-methyl-2-pyrrolidone (NMP) varnish and paint remover solvents for removal of organic coatings
US6187108B1 (en) * 1999-02-25 2001-02-13 Huntsman Petrochemical Corporation Alkylene carbonate-based cleaners

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11708502B2 (en) 2017-06-20 2023-07-25 W.M. Barr & Company, Inc. Paint remover composition and method of making
US11827812B2 (en) 2017-06-20 2023-11-28 W.M. Barr & Company, Inc. Paint remover composition and method of making
US11958991B2 (en) 2017-06-20 2024-04-16 W.M. Barr & Company, Inc. Paint remover composition and method of making
US12104086B2 (en) 2017-06-20 2024-10-01 W.M. Barr & Company, Inc. Paint remover composition and method of making
US12110420B2 (en) 2017-06-20 2024-10-08 W. M. Barr & Company, Inc Paint remover composition and method of making
US12012572B2 (en) 2017-10-09 2024-06-18 W.M. Barr & Company, Inc. Automotive paint remover composition and method of making
WO2019210183A1 (fr) * 2018-04-27 2019-10-31 W.M. Barr & Company, Inc. Décapant pour peinture présentant une inflammabilité réduite
CN112512708A (zh) * 2018-04-27 2021-03-16 W·M·巴尔公司 具有降低的易燃性的除漆剂
US12031061B2 (en) 2019-06-21 2024-07-09 W.M. Barr & Company, Inc. Paint remover
US12240998B1 (en) 2024-03-20 2025-03-04 W. M. Barr & Company, Inc. Paint remover compositions comprising tetrahydrofuran, alkanediol, and amine and methods of making and using the same
US12247139B1 (en) 2024-03-20 2025-03-11 W. M. Barr & Company, Inc. Paint remover compositions comprising tetrahydrofuran, alkanediol, and amine and methods of making and using the same

Also Published As

Publication number Publication date
WO2003062325A3 (fr) 2004-05-27
AU2003209305A1 (en) 2003-09-02

Similar Documents

Publication Publication Date Title
US6159915A (en) Paint and coating remover
EP1175462B1 (fr) Suppresseur de peinture et de depot
US6395103B1 (en) Degreasing compositions
US6162776A (en) Paint and coating remover
US6479445B1 (en) Paint stripping compositions
US6239090B1 (en) Thickened paint and coating remover
EP0551378A1 (fr) Procede d'activation de solvants n-methyl-2-pyrrolidone (nmp) et/ou gamma-butyrolactone (blo) utilise pour oter le vernis et la peinture
US6608012B2 (en) Process and formulations to remove paint and primer coatings from thermoplastic polyolefin substrates
US6548464B1 (en) Paint stripper for aircraft and other multicoat systems
WO2003062325A2 (fr) Compositions decapantes pour revetements et leur utilisation
US6420327B1 (en) Carbonate-based coating removers
WO2016014763A1 (fr) Compositions à base de solvants mélangés pour éliminer de la peinture et du vernis

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载