EP0970141A1 - Compositions, exemptes de compose organique volatil et a base de solvants organiques, ne reagissant que faiblement avec le radical libre hydroxyle et ne contribuant que fort peu a la formation de l'ozone atmospherique - Google Patents

Compositions, exemptes de compose organique volatil et a base de solvants organiques, ne reagissant que faiblement avec le radical libre hydroxyle et ne contribuant que fort peu a la formation de l'ozone atmospherique

Info

Publication number
EP0970141A1
EP0970141A1 EP98915169A EP98915169A EP0970141A1 EP 0970141 A1 EP0970141 A1 EP 0970141A1 EP 98915169 A EP98915169 A EP 98915169A EP 98915169 A EP98915169 A EP 98915169A EP 0970141 A1 EP0970141 A1 EP 0970141A1
Authority
EP
European Patent Office
Prior art keywords
composition
bromopropane
composition according
acetone
resin
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.)
Withdrawn
Application number
EP98915169A
Other languages
German (de)
English (en)
Inventor
Richard G. Henry
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.)
Advanced Chemical Design Inc
Original Assignee
Advanced Chemical Design 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 US09/022,779 external-priority patent/US6048471A/en
Application filed by Advanced Chemical Design Inc filed Critical Advanced Chemical Design Inc
Publication of EP0970141A1 publication Critical patent/EP0970141A1/fr
Withdrawn legal-status Critical Current

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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
    • C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents

Definitions

  • This invention pertains to the art of solvent blends and solvent/resin blends. More, particularly this invention pertains to blends that do not contribute to the formation of ground based ozone or smog.
  • the invention is particularly applicable to solvent blends and solvent/resin blends that have no volatile organic compounds for use with adhesives, coatings, inks, cleaning and blowing agents and the like and will be described with particular reference thereto. However, it will be appreciated that the invention may be advantageously employed in other environments and applications.
  • hydrocarbon-based solvents have been used to dissolve organic materials in many industrial applications.
  • hydrocarbon-based solvents have fallen out of favor because they have been classified by the United States Environmental Protection Agency and other international regulatory bodies as materials that contribute to the formation of ground based ozone or smog.
  • a highly-reactive, hydrocarbon-based solvent reacts with hydroxyl radicals and ultraviolet light very close to the ground to form a photochemical smog that is considered harmful and in some cases dangerous.
  • Some cities have severe smog which reduces visibility and actually causes "ozone alerts".
  • the smog is caused by hydrocarbon emissions from cars.
  • another major contributor is industrial use of hydrocarbon-based solvents such as hexane and toluene.
  • the benchmark for desired reaction rates of hydrocarbon-based compounds is ethane. If a compound has a reaction rate with the hydroxyl radical and ultraviolet (“UV") light that is faster than ethane, the compound reacts too close to the ground and consequently generates ozone and smog. Such compounds are defined as volatile organic compounds (VOCs) . On the other hand, if a compound has a reaction rate that is slower than ethane, the compound reaches higher into the atmosphere before reacting with the hydroxyl radical and UV light. In such instances the non-VOC compound does not contribute to the formation of ground based ozone and smog.
  • VOCs volatile organic compounds
  • VOCs Some of the more reactive VOCs are: toluene; methyl ethyl ketone; diacetone alcohol; hexane; isopropyl alcohol; pentane; dibasic esters; trichloroethylene; benzene; ethyl acetate; butyl acetate; n-methyl pyrollidone; glycol ethers; d-limonene; terpene hydrocarbon solvents; dimethyl ether; and, tetrahydrofuran.
  • VOCs in coatings, inks, and adhesives As a result, water-borne coatings have become the most important type of coatings in coating and adhesive systems.
  • water-borne coatings must contain some volatile organic compound content. This is because water flashes off too fast from the water-based latex or emulsion to make a good film.
  • a slower evaporating solvent such as a glycol ether is added to the latex to aid in film formation.
  • glycol ethers are primary examples of VOCs and thus dangerous to the environment.
  • Halogenated hydrocarbon-based compounds have reaction rates that are slower than ethane. However, these halogenated compounds are ozone depleting. consequently, they are not suitable VOC-free solvents.
  • Patent No. 3,950,185 to Toyama teaches film removing compositions which contain methylene chloride and bromochloromethane which are not VOCs. However, these compositions also contain methanol and monochlorobenzene which are VOCs.
  • Patent No. 3,924, 455 to Begishagen describes a formulation containing mineral spirits which removes lacquer stress coatings. These mineral spirits are also VOCs.
  • An object of the present invention is the identification of some high-performance solvents and solvent/resin blends which are non-flammable or self- extinguishing and do not contribute to the formation of ground-based ozone.
  • Another object of the present invention are solvents and solvent/resin blends that are safer to the environment than even water-based systems which still must contain a volatile organic solvent to aid in film formation.
  • Yet another object of the present invention are environmentally-safer solvent compositions which do not contribute to the formation of ground based ozone which will be useful in the formulation of cleaning agents, coatings, adhesives, inks and also blowing agents for the production of plastic foams.
  • the present invention contemplates new and improved solvent and solvent-resin compositions which overcome all of the above referenced problems and others and which are economical and effective for their intended uses.
  • a solvent-resin composition having generally zero volatile organic compounds (VOCs) .
  • the composition consists essentially of a resin component and a solvent component.
  • the solvent component is 5- 95% by total volume of the solvent-resin composition and is one or more of the zero-VOC solvents selected from the group consisting of: chlorobromomethane; 1-bromopropane; n-alkane (C12-C18) ; t-butyl acetate; perchloroethylene; benzotrifluoride; parachlorobenzotrifluoride; acetone;
  • the solvent component is present in the amount 40-95% by total volume of the composition.
  • the solvent component is present in the amount 30%-80% by total volume of the composition.
  • a principal advantage of the invention is that it is environmentally safer yet still capable of effectively dissolving resins.
  • Another advantage of the invention is that it may be used in place of solvents currently used for inks, adhesives, coatings and the like. Still other advantages and benefits of the invention will become apparent to those skilled in the art upon a reading and understanding of the following detailed description.
  • compositions of the present invention are high-performance solvent and solvent-resin blends that are generally free of VOCs.
  • the compositions as herein described and as set forth in the claims are expressed in terms of percentages by volume unless clearly indicated to the contrary.
  • hydrocarbon e.g., olefins, terpene resins, rosin esters, coumarone-indene , styrene- butadiene, styrene,
  • Effective solvents of the present invention which have reaction rates with hydroxyl ion slower than ethane are: 1) chlorobromomethane;
  • Table 1 uses the identifiers set out above, i.e., a numeral alone for the solvent and a numeral followed by "a" for the application.
  • One preferred embodiment includes mixing one or more of the polymeric resins: acrylic-thermoplastic; acrylic-thermosetting; chlorinated rubber; epoxy resin; hydrocarbon (e.g., olefins, terpene resins, rosin esters, coumarone-indene, styrene- butadiene, styrene, methyl-styrene, vinyl- toluene, nitrocellularlose, polychloroprene, polyamide, polyvinyl chloride and isobutylene) ; phenolic; polyester and/or alkyd; polyurethane; silicone; urea; and/or vinyl or vinyl acetate, with 10-90%, by total volume of the composition, of one or more of non-VOC solvents such as: chlorobromomethane;
  • non-VOC solvents such as: chlorobromomethane
  • the mixture preferably has a high resin content, i.e., a resin content of 20%-60% by volume.
  • the mixture preferably contains a lower concentration of the resin, i.e., 5%- 30% by volume.
  • various pigments or additives are added to achieve a desired range of properties.
  • methyl acetate by total volume of the composition, is added to 10-95% of a solvent or solvent blend selected from the group: chlorobromomethane; 1-bromopropane; n-alkane (C12-C18) ; t-butyl Acetate; perchloroethylene; benzotrifluoride; parachlorobenzotrifluoride; acetone;
  • a solvent or solvent blend selected from the group: chlorobromomethane; 1-bromopropane; n-alkane (C12-C18) ; t-butyl Acetate; perchloroethylene; benzotrifluoride; parachlorobenzotrifluoride; acetone;
  • the following enumerated embodiments have the ability to dissolve resins for the production of coatings, adhesives, and inks as well.
  • the embodiments are equally useful as cleaning formulations.
  • the ranges for the embodiments are expressed in % by volume of the total solvent-resin composition or, alternatively, the total solvent composition of an initially non-resin containing solvent, such as a cleaning composition.
  • the embodiments are:
  • VOC-free embodiment has the ability to dissolve resins for the production of coatings, adhesives, and inks as well.
  • compositions include VOC-free solvents which have the ability to dissolve resins for the production of coatings, adhesives, and inks.
  • the compositions include any of the above-listed resins and the following solvent mixtures, which are expressed in terms of % by volume of the solvent-resin composition:
  • VOC-free embodiment expressed in terms of % by volume of total composition, is useful as an environmentally-safer blowing agent composition for the production of polyurethane or isocyanurate foams :
  • Another embodiment useful as an environmentally-safer blowing agent composition is: 100 parts by weight polyether triol; 50 parts by weight toluene diisocyanate or toluene disocyanurate; 2 parts by weight water;
  • Still another embodiment useful as an environmentally-safer blowing agent composition in terms of percent by weight of the total composition (including catalyst and surfactant), is: 50-70% polyether triol; 20-40% toluene diisocyanate or toluene disocyanurate;
  • a more limited embodiment useful as an environmentally-safer blowing agent composition in terms of percent by weight of the total composition (including catalyst and surfactant), is:
  • An embodiment of a zero-VOC adhesive is 350 grams of 1-bromopropane and/or benzotriflouride to which is added 30-50% by weight of a hydrocarbon resin, preferably an olefin, rosin ester or terpene resin, which acts as a tackifier. Then, 100 grams of styrene-butadiene polymer, polychloroprene polymer, polyvinyl chloride polymer, acrylic, epoxy, urethane, nitrocellulose, or styrene is added to the mixture. This mixture produces a contact adhesive with excellent bond strength.
  • this mixture contains approximately 40-90%, volume, of 1-bromopropane and/or benzotriflouride, 5-35% of a hydrocarbon resin, and 5-25% of styrene-butadiene polymer, polychloroprene polymer, polyvinyl chloride polymer, acrylic, epoxy, urethane, nitrocellulose, or styrene.
  • Another zero-VOC adhesive starts with 100 grams of 1-bromopropane and/or benzotrifluoride. Then, 10-100 grams of styrene-butadiene, polychloroprene, polyvinyl chloride, acrylic, epoxy, urethane, nitrocellulose, or styrene polymer or resin is added.
  • this mixture contains approximately 40- 95%, by volume, of 1-bromopropane and/or benzotriflouride, and 5-60% of styrene-butadiene, polychloroprene, polyvinyl chloride, acrylic, epoxy, urethane, nitrocellulose, or styrene polymer or resin.
  • Still another preferred embodiment of this mixture contains approximately 70-95%, by volume, of 1-bromopropane and/or benzotriflouride, and 5-30% of styrene-butadiene, polychloroprene, polyvinyl chloride, acrylic, epoxy, urethane, nitrocellulose, or styrene polymer or resin.
  • Still another embodiment of a zero-VOC adhesive starts with 350g 1-bromopropane and/or benzotriflouride. Then, 20-100 grams of styrene butadiene rubber is added. Optionally, 5-10%, by volume, acetone is added to improve solubility if necessary.
  • Another preferred embodiment of this mixture contains approximately 50-90%, by volume, of 1- bromopropane, and 10-30% of acrylic polymer or urethane polymer.
  • acetone is added to improve solubility if necessary.
  • VOC-free embodiment has the ability to dissolve resins for the production of coatings, adhesives, and inks as well.
  • the solvent includes stabilizers to stabilize against attack on aluminum.
  • the embodiment is useful in cleaning formulations:
  • Table 2 shows formaldehyde-based resins or polymers that are combinable with zero-VOC methyl acetate.
  • the methyl acetate preserves the superior functional properties that the resins had with conventional VOC solvents.
  • Table 3 shows the various types of resins that are soluble in methyl acetate. This chart is a reference guide to combine the class of resin with methyl acetate so as to make a VOC free solvent-resin system which can be applied to various substrates listed in the "Typical uses" column.
  • the solvent-resin system may optionally include various pigments and additives to achieve desired properties.
  • methyl acetate 10-95% by total volume of methyl acetate is mixed with one or more of the following types of resins: alcohol-soluble, baking type (heat reactive) ; rosin-modified phenolics (non-heat reactive) ; synthetic-substituted phenol (head reactive) ; synthetic-substituted phenol (non-heat reactive) ; terpene phenol; acrylics-thermoplastic type; acrylics-thermosetting type; chlorinated rubber; epoxy (either one pack or two pack) ; polyesters and alkyds; polyurethane; hydrocarbon resins: olefins, terpenes, coumarone- indene, petroleum resins, methyl styrene, styrene, vinyl toluene, and isobutylene; silicone resins; and, vinyl
  • zero-VOC solvents may be mixed with the methyl acetate to produce environmentally-safe compositions.
  • the zero-VOC solvent (s) may directly substitute for a portion of the methyl acetate.
  • Some of these other zero-VOC solvents are: chlorobromomethane;
  • VOC solvents 2- (ethoxydifluoromethyl) -1,1,1,2,3,3,3- heptafluoropropane; methylene chloride; and, technical white oils (mineral oils) .
  • small amounts, i.e., 0-5% by volume of VOC solvents may be added to produce generally VOC-free compositions that are environmentally safer. This applies as well to all embodiments described below.
  • 10- 90% by total volume of methyl acetate is mixed with one or more of the above-listed types of resins.
  • 10-80% by total volume of methyl acetate is mixed with one or more of the above-listed types of resins.
  • 80-95% by total volume of methyl acetate is mixed with one or more of the above- listed types of resins.
  • approximately 85-95% by total volume of methyl acetate is mixed with one or more of the above-listed types of resins.
  • approximately 90% by total volume of methyl acetate is mixed with one or more of the above-listed types of resins.
  • . approximately 95% by total volume of methyl acetate is mixed with one or more of the above-listed types of resins.
  • 10 grams of phenolic resin is added to 90 grams of methyl acetate until all of the resin is dissolved.
  • the mixture is then applied to a steel coupon and baked at 275 F. for 10 minutes. Upon baking, a hard coating forms on the panel.
  • the coating is clear and has no noticeable defects.
  • the coating formulation contains no volatile organic compounds which would contribute to ground based ozone or smog formation.
  • Another preferred embodiment of this mixture contains approximately 5% by volume phenolic resin and 95% by volume of methyl acetate.
  • Yet another preferred embodiment of a coating formulation includes 20 grams of chlorinated rubber and 80 grams of methyl acetate. After the chlorinated rubber has dissolved, the formulation is spread onto an aluminum coupon and allowed to dry. After 1 hour, the solvent is seen to have evaporated and left behind a hard coating on the aluminum. Another preferred embodiment of this mixture contains approximately 10% by volume chlorinated rubber and 90% by volume of methyl acetate.
  • Still another preferred embodiment of a coating formulation includes 20 grams of acrylic resin and 80 grams of methyl acetate. The acrylic resin is dissolved in the methyl acetate. Then, the formulation is spread upon a 4" x 4" piece of wood and allowed to dry. After 1 hour, the coating has penetrated into the wood leaving a glossy, hard finish on its exterior. This same coating composition works equally well on plastics and metals. Another preferred embodiment of this mixture contains approximately 10% by volume acrylic resin and 90% by volume of methyl acetate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Dispersion Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention a trait à des compositions résine-solvant, sans danger pour l'environnement, qui sont, en général, exemptes de composés organiques volatils (VOC). Le solvant et les compositions résine-solvant sont susceptibles de remplacer des solvants hydrocarbonés à teneur élevée en VOC et peuvent être utilisés dans des encres, des enduits, des adhésifs et analogues. Ces nouvelles composition ne réagissent que faiblement avec le radical libre hydroxyle et, partant, peuvent atteindre les hautes couches de l'atmosphère avant de se décomposer.
EP98915169A 1997-03-24 1998-03-24 Compositions, exemptes de compose organique volatil et a base de solvants organiques, ne reagissant que faiblement avec le radical libre hydroxyle et ne contribuant que fort peu a la formation de l'ozone atmospherique Withdrawn EP0970141A1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US4151097P 1997-03-24 1997-03-24
US41510P 1997-03-24
US5307397P 1997-07-18 1997-07-18
US53073P 1997-07-18
US09/022,779 US6048471A (en) 1997-07-18 1998-02-12 Zero volatile organic compound compositions based upon organic solvents which are negligibly reactive with hydroxyl radical and do not contribute appreciably to the formation of ground based ozone
US22779 1998-02-12
PCT/US1998/005937 WO1998042774A1 (fr) 1997-03-24 1998-03-24 Compositions, exemptes de compose organique volatil et a base de solvants organiques, ne reagissant que faiblement avec le radical libre hydroxyle et ne contribuant que fort peu a la formation de l'ozone atmospherique

Publications (1)

Publication Number Publication Date
EP0970141A1 true EP0970141A1 (fr) 2000-01-12

Family

ID=27361951

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98915169A Withdrawn EP0970141A1 (fr) 1997-03-24 1998-03-24 Compositions, exemptes de compose organique volatil et a base de solvants organiques, ne reagissant que faiblement avec le radical libre hydroxyle et ne contribuant que fort peu a la formation de l'ozone atmospherique

Country Status (3)

Country Link
EP (1) EP0970141A1 (fr)
AU (1) AU6941898A (fr)
WO (1) WO1998042774A1 (fr)

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US6818049B1 (en) 1998-05-05 2004-11-16 Exxonmobil Chemical Patents Inc. Environmentally preferred fluids and fluid blends
US6280519B1 (en) 1998-05-05 2001-08-28 Exxon Chemical Patents Inc. Environmentally preferred fluids and fluid blends
EP1127935B1 (fr) * 1998-07-17 2009-12-16 Daikin Industries, Ltd. Composition de traitement de surface contenant du fluor
AU6399999A (en) 1998-09-29 2000-04-17 Loctite Corporation Multi-component solvent systems for fluorinated compounds and cleaners and delivery systems based thereon
DE19944279A1 (de) * 1999-09-15 2001-03-22 Stahlgruber Gruber & Co Otto Polychloropren/Diisocyanat-Klebstoffsystem, wobei in der Chloropren-Kautschuk-Lösung n-Propylbromid als Lösungsmittel eingesetzt wird
US6207224B1 (en) 1999-10-06 2001-03-27 E. I. Du Pont De Nemours And Company Process for coating thermoplastic substrates with a coating composition containing a non-aggressive solvent
FR2806090B1 (fr) * 2000-03-10 2002-05-24 Extractive Encres contenant au moins un solvant fluore et procede de fabrication de telles encres
US7465759B1 (en) 2005-02-28 2008-12-16 Gem Gravure Company, Inc. Inkjet inks and methods of printing with the same
BRPI0721473A2 (pt) * 2007-02-27 2013-01-08 Tarksol Internat L L C um mÉtodo de aplicar uma pintura nço composto orgÂnico volÁtil (cov)
US9080070B2 (en) 2012-04-03 2015-07-14 Gem Gravure Co., Inc. Inkjet ink for printing on fluoropolymers
US9221985B2 (en) * 2013-12-09 2015-12-29 Tbf Environmental Technology Inc. Solvent compositions
RU2740285C2 (ru) * 2016-06-29 2021-01-12 ЛЕНКСЕСС Дойчланд ГмбХ Способ получения амидометилированных винилароматических бисерных полимеризатов

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Also Published As

Publication number Publication date
WO1998042774A1 (fr) 1998-10-01
AU6941898A (en) 1998-10-20

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