EP2010596A2 - Blähmittelzusammensetzung - Google Patents

Blähmittelzusammensetzung

Info

Publication number
EP2010596A2
EP2010596A2 EP07731822A EP07731822A EP2010596A2 EP 2010596 A2 EP2010596 A2 EP 2010596A2 EP 07731822 A EP07731822 A EP 07731822A EP 07731822 A EP07731822 A EP 07731822A EP 2010596 A2 EP2010596 A2 EP 2010596A2
Authority
EP
European Patent Office
Prior art keywords
weight
hydro
blowing agent
compound
composition according
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Withdrawn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
EP07731822A
Other languages
English (en)
French (fr)
Inventor
Vincent Enaux
Laurent Latil
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.)
Arkema France SA
Original Assignee
Arkema France SA
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 Arkema France SA filed Critical Arkema France SA
Publication of EP2010596A2 publication Critical patent/EP2010596A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • 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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0014—Use of organic additives
    • C08J9/0023—Use of organic additives containing oxygen
    • 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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • 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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent 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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/02—Halogenated hydrocarbons
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/12—Organic compounds only containing carbon, hydrogen and oxygen atoms, e.g. ketone or alcohol
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C08J2203/142—Halogenated saturated hydrocarbons, e.g. H3C-CF3
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C08J2203/146—Saturated hydrocarbons containing oxygen and halogen atoms, e.g. F3C-O-CH2-CH3
    • 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
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the present invention relates to an expanding agent composition suitable for use in the manufacture of thermoplastic and thermosetting foams.
  • HFC as blowing agent in the manufacture of isocyanate-based foams
  • WO 02/099006 discloses an azeotropic composition of HFC and trans 1,2-dichloroethylene as an expanding agent in the manufacture of foams.
  • the object of the present invention is to provide an expanding agent composition that meets both negligible ODP and low GWP criteria.
  • the present invention has, as a first object, an expansion agent composition comprising an organic solvent of boiling point, at atmospheric pressure, greater than 0 ° C and having a low GWP, preferably less than 100, or better still less than 20, and at least one compound (C) chosen from haloketones, fluoroacids, fluoroesters, fluoroamines, (hydro) fluoroethers, (hydro) fluorothioethers, (hydro) fluoroolefins, cyclic (hydro) fluorocarbons and iodofluoro (hydro) carbides.
  • C compound chosen from haloketones, fluoroacids, fluoroesters, fluoroamines, (hydro) fluoroethers, (hydro) fluorothioethers, (hydro) fluoroolefins, cyclic (hydro) fluorocarbons and iodofluoro (hydro) carbides.
  • the blowing agent composition essentially contains an organic solvent with a boiling point, at atmospheric pressure, greater than 0 ° C. and having a low GWP, preferably less than 100, or better still less than 20, and at least a compound (C) chosen from haloketones, fluoroacids, fluoroesters, fluoroamines, (hydro) fluoroethers, (hydro) fluorothioethers, (hydro) fluoroolefins, cyclic (hydro) fluorocarbons and iodofluoro (hydro) carbides .
  • the blowing agent composition according to the present invention has not only negligible ODP but also a low GWP, preferably less than 100.
  • This blowing agent composition preferably comprises 1 to 99% by weight of solvent and 99 to 1% by weight of compound (s) C.
  • it comprises 50 to 99% by weight of solvent and 1 to 50% by weight of compound (s) C.
  • the advantageously preferred composition comprises 70 to 99% by weight of solvent and 1 to 30% by weight of compound (s) C.
  • the (hydro) fluoroethers are preferably chosen as compound C.
  • (Hydro) fluoroethers denote compounds containing carbon, fluorine, at least one ether function and optionally hydrogen.
  • hydro fluoroethers mention may be made in particular of those of general formula (Rh - O) x - Rf in which x is equal to 1 or 2; R n represents an optionally fluorinated alkyl group having from 1 to 4 carbon atoms and Rf represents a (per) fluorinated aliphatic group having at least 2 carbon atoms, preferably between 2 and 9 carbon atoms. R may also include heteroatoms such as oxygen, nitrogen and sulfur.
  • the preferred hydrofluoroethers are those for which the value of x is equal to 1.
  • the compounds of the following formula may also be suitable as hydrofluoroethers: C 8 F 17 OCH 3 , C 5 F 11 OC 2 H 5 , C 3 F 7 OCH 3 , or 1,1-dimethoxyperfluorocyclohexane.
  • nC 4 F 9 OCH 3 , CF 3 CF (CF 3 ) CF 2 OCH 3 and (CF 3 ) 3 COCH 3 and 1 ethoxy nonafluorobutane, nC 4 F 9 OC 2 H 5 , CF 3 CF ( CF 3 ) CF 2 OC 2 H 5 and (CF 3 ) 3 COC 2 H 5 are advantageously chosen as hydrofluoroethers.
  • organic solvent there may be mentioned in particular 1, 1-dichloroethane, dioxolane, dimethylcarbonate, propylene carbonate, nonafluoro-tert-butanol, acetone, tert-butylmethyl ether, diisopropyl ether, diethyl ether , dipropyl ether, ethyltertiobutyl ether, 1,2-dimethoxyethane, dimethoxymethane, 1,1-dimethoxyethane, methanol, ethanol, n-propanol, isopropanol, n, s, t- butanol, ethyl propionate, ethyl acetate, ethyl formate, methyl acetate, methyl formate, propyl acetate, isopropyl acetate, isopentane, 2,2-dimethylbutane, 2,3-dimethylbutane, 2,3-dimethylp
  • the dioxolane and the dimethylcarbonate are advantageously chosen as organic solvent.
  • Fluoroamines denote compounds containing carbon, fluorine, at least one amine function, and optionally hydrogen and chlorine.
  • N- (difluoromethyl) -N, N-dimethylamine may be mentioned,
  • (Hydro) fluorothioethers are compounds containing carbon, fluorine, at least one thio ether function and optionally hydrogen and chlorine.
  • 1, 1, 1, 2,2-pentafluoro-2 - [(pentafluoroethyl) thio] ethane can be mentioned.
  • An example of a cyclic (hydro) fluorocarbon is heptafluorocyclopentane.
  • Fluoroacids denote compounds containing carbon, fluorine, at least one acid function, and optionally hydrogen and chlorine.
  • Fluoroesters denote compounds containing carbon, fluorine, at least one ester function, and optionally hydrogen and chlorine.
  • iodofluoro (hydro) carbides there may be mentioned in particular iodotrifluoromethane (CF 3 I), iodopentafluoroethane (C 2 F 5 I), 1-iodoheptafluoropropane (CF 3 CF 2 CF 2 I), 2-iodoheptafluoropropane (CF 3 CFICF 3 ), iodo-1, 1, 2,2-tetrafluoroethane (CHF 2 CF 2 I), 2-iodo-1, 1, 1-trifluoroethane (CF 3 CH 2 I), iodotrifluoroethylene (C 2 F 3 I), 1-iodo-1, 1, 2,3,3,3-hexafluoropropane (CF 3 CHFCF 2 I), 2-iodononafluoro-tert-butane ((CF 3 ) 3 CI).
  • Haloketones denote compounds containing carbon, fluorine, at least one ketone function, and optionally hydrogen, chlorine and bromine.
  • the haloketones may be represented by the general formula RiCOR 2 , wherein R 1 , R 2, which may be identical or different, are independently selected from the group consisting of aliphatic or alicyclic fluorinated carbon radicals optionally containing hydrogen, bromine or chlorine.
  • the chain of carbon radicals can be linear or branched, saturated or unsaturated.
  • R 1 and R 2 may optionally form a ring.
  • the haloketones may contain from 3 to 10 carbon atoms, preferably from 4 to 8 carbon atoms.
  • haloketones may further contain other heteroatoms such as oxygen to form an additional ketone function or an ether, aldehyde or ester group.
  • haloketones there may be mentioned in particular 1, 1, 1, 2,2,4,5,5,5-nonafluoro-4- (trifluoromethyl) -3-pentanone, 1, 1, 1, 2,4,5 5,5-octafluoro-2,4-bis (trifluoromethyl) -3-pentanone, 1,1,2,4,4,5,5-octafluoro-2-
  • 1,1,1,2,2,5,5,5-nonafluoro-4- (trifluoromethyl) -3-pentanone is preferred.
  • haloketones mention may also be made of bromofluoro ketones, for example monobromoperfluoro ketones, monohydromonobromoperfluoro ketones, (perfluoroalkoxy) monobromoperfluoro ketones, (fluoroalkoxy) monobromoperfluoro ketones and monochloromonobromoperfluoro ketones.
  • 1,1,1,3,3-Pentafluoropropene HFO-1225zc
  • cis and trans isomer of 1,1,1,3-tetrafluoropropene (HFO-1234ze) and 1,1,1,2-tetrafluoropropene (HFO-1234yf) are particularly preferred.
  • the particularly preferred blowing agent composition comprises 1,3 dioxolane and at least one hydrofluoroether.
  • An expansion agent composition comprising 1,3 dioxolane and 1 methoxy nonafluorobutane has given very interesting results.
  • a composition comprising 1,3 dioxolane and 1 ethoxy nonafluorobutane.
  • blowing agent composition there may be mentioned in particular that comprising dimethylcarbonate and at least one hydrofluoroether, such as 1-methoxy-nonafluorobutane and 1-ethoxy-nonafluorobutane.
  • the blowing agent composition according to the present invention advantageously leads to thermoplastic and thermosetting foams having a good dimensional stability. It is particularly suitable for the manufacture of polyurethane foams and advantageously to the manufacture of rigid polyurethane foams.
  • polyurethane foam components are premixes. More generally, the formulation of the foams is premixed into two components.
  • the first component better known under the name “component A” comprises the isocyanate or polyisocyanate composition.
  • component B comprises the polyol or polyol mixture, the surfactant, the catalyst (s), and the blowing agent (s).
  • the subject of the present invention is therefore a composition comprising a polyol or mixture of polyols and the blowing agent of the first object.
  • the composition according to the second object is preferably in emulsion form.
  • the blowing agent is preferably from 1 to 60 parts by weight per 100 parts by weight of polyol or mixture of polyols in the composition of the second article.
  • it represents between 5 and 35 parts by weight per 100 parts by weight of polyol or mixture of polyols.
  • polyols there may be mentioned glycerol, ethylene glycol, trimethylolpropane, pentaerythritol, polyether polyols, for example those obtained by condensation of an alkylene oxide or a mixture of alkylene oxides with the glycerol, ethylene glycol, trimethylolpropane, pentaerythritol, polyesterspolyols, for example those obtained from polycarboxylic acids, in particular oxalic acid, malonic acid, succinic acid, adipic acid, maleic acid, , fumaric acid, isophthalic acid, terephthalic acid, with glycerol, ethylene glycol, trimethylolpropane, pentaerythritol.
  • polyether polyols for example those obtained by condensation of an alkylene oxide or a mixture of alkylene oxides with the glycerol, ethylene glycol, trimethylolpropane, pentaerythritol
  • polyether polyols obtained by the addition of alkylene oxides, in particular ethylene oxide and / or propylene oxide, to the aromatic amines, in particular the mixture of 2,4 and 2,6 toluene diamine, are also suitable.
  • alkylene oxides in particular ethylene oxide and / or propylene oxide
  • polyols that may be mentioned include hydroxyl-terminated polythioethers, polyamides, polyesteramides, polycarbonates, polyacetals, polyolefins and polysiloxanes.
  • the present invention also relates to a process for manufacturing polyurethane foams.
  • This process comprises reacting an organic polyisocyanate (including diisocyanate) with the composition according to the second object.
  • This reaction can be activated using an amine and / or other catalysts and surfactants.
  • the process for producing polyurethane foams can be carried out in the presence of a chemical blowing agent such as water.
  • polyisocyanate there may be mentioned in particular aliphatic polyisocyanates with a hydrocarbon group of up to 18 carbon atoms, cycloaliphatic polyisocyanates with a hydrocarbon group of up to 15 carbon atoms, aromatic polyisocyanates with an aromatic hydrocarbon group having from 6 to 15 carbon atoms and arylaliphatic polyisocyanates with an arylaliphatic hydrocarbon group having 8 to 15 carbon atoms.
  • the preferred polyisocyanates are 2,4-diisocyanato and 2,6-toluyl, diphenylmethane diisocyanate, polymethylenepolyphenyl isocyanate and mixtures thereof.
  • Modified polyisocyanates such as those containing carbodiimide groups, urethane groups, isocyanurate groups, urea groups or biurea groups may also be suitable.
  • Procedure for producing a rigid polyurethane foam 100 parts by weight of polyol Stepanpol PS2412 (polyester type), 1.5 parts by weight of surfactant Tegostab B8465, 3 parts by weight of water and 10 parts by weight of the composition of the composition are introduced into a beaker. expansion agent according to the invention. Then, we shake for a minute, using a vertical mechanical stirrer at a medium speed of 2000 rpm, the resulting mixture.
  • Desmodur 44V70L isocyanate
  • the catalyst consisting of 2.82 parts by weight of Dabco K15 (mixture of potassium salt 2-ethyl hexanoic acid and diethylene glycol) is injected with a plastic syringe and 0 18 parts by weight of Polycat 5 (Pentamethyldiethylenetriamine).
  • the mixture is poured into a rectangular mold covered with paper. It is then waited 5 minutes before demolding the foam and after 24 hours, the foam is cut with a band saw. The volume of the cut foam is measured before passing to the oven and after 72 hours at 70 ° C. in an oven. The difference between the volume of the foam after and before the oven gives an indication of the dimensional stability and the data are reported in the table below.
  • volume difference (%) (Final volume - Initial volume) / Initial volume.
  • blowing agent used for the examples are as follows:
  • Example 1 (according to the invention): 75% by weight of dimethyl carbonate (DMC) and 25% by weight of 1-methoxy-nonafluorobutane
  • Example 2 (according to the invention): 75% by weight of 1,3-dioxolane and 25% by weight of 1-methoxy-nonafluorobutane.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Emergency Medicine (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Lubricants (AREA)
EP07731822A 2006-03-31 2007-03-26 Blähmittelzusammensetzung Withdrawn EP2010596A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0602796A FR2899233B1 (fr) 2006-03-31 2006-03-31 Composition d'agent d'expansion
US80036606P 2006-05-15 2006-05-15
PCT/FR2007/051010 WO2007113434A2 (fr) 2006-03-31 2007-03-26 Composition d'agent d'expansion

Publications (1)

Publication Number Publication Date
EP2010596A2 true EP2010596A2 (de) 2009-01-07

Family

ID=37569243

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07731822A Withdrawn EP2010596A2 (de) 2006-03-31 2007-03-26 Blähmittelzusammensetzung

Country Status (10)

Country Link
US (1) US20100222443A1 (de)
EP (1) EP2010596A2 (de)
JP (1) JP2009531508A (de)
KR (1) KR20090012210A (de)
CN (1) CN101443394B (de)
AU (1) AU2007232495A1 (de)
CA (1) CA2643855A1 (de)
FR (1) FR2899233B1 (de)
MX (1) MX2008012349A (de)
WO (1) WO2007113434A2 (de)

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Also Published As

Publication number Publication date
FR2899233A1 (fr) 2007-10-05
MX2008012349A (es) 2009-03-06
FR2899233B1 (fr) 2010-03-12
KR20090012210A (ko) 2009-02-02
CN101443394A (zh) 2009-05-27
CN101443394B (zh) 2012-05-16
JP2009531508A (ja) 2009-09-03
US20100222443A1 (en) 2010-09-02
CA2643855A1 (fr) 2007-10-11
WO2007113434A3 (fr) 2008-11-13
WO2007113434A2 (fr) 2007-10-11
AU2007232495A1 (en) 2007-10-11

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