EP2024431A2 - Blähmittelzusammensetzung - Google Patents

Blähmittelzusammensetzung

Info

Publication number
EP2024431A2
EP2024431A2 EP07731825A EP07731825A EP2024431A2 EP 2024431 A2 EP2024431 A2 EP 2024431A2 EP 07731825 A EP07731825 A EP 07731825A EP 07731825 A EP07731825 A EP 07731825A EP 2024431 A2 EP2024431 A2 EP 2024431A2
Authority
EP
European Patent Office
Prior art keywords
weight
hydro
dichloroethylene
blowing agent
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07731825A
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 EP2024431A2 publication Critical patent/EP2024431A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C08J9/143—Halogen containing compounds
    • 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
    • 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
    • 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 dichloroethylene 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.
  • the blowing agent composition essentially contains dichloroethylene and at least one compound (C) chosen from haloketones, fluoroacids, fluoroesters, fluoroamines,
  • the blowing agent composition according to the present invention has not only a negligible ODP but also a low GWP, preferably less than 150.
  • the blowing agent composition comprises from 1 to 94% by weight of dichloroethylene and from 99 to 6% by weight of compound (s) C, preferably from
  • the (hydro) fluoroethers are preferably chosen as compound C.
  • the (hydro) fluoroethers denote compounds comprising carbon, fluorine, at least one ether function and optionally hydrogen.
  • the preferred hydrofluoroethers are those for which the value of x is equal to 1. Mention may in particular be made of 1 methoxy nonafluorobutane, n-C 4 F 9 OCH 3 , CF 3 CF (CF 3 ) CF 2 OCH 3 and (CF 3 ) 3 COCH 3) 1 ethoxy nonafluorobutane, 1C 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 .
  • the compounds of the following formula may also be suitable as hydrofluoroethers: C 8 F 7 OCH 3 , C 5 FnO C 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.
  • dichloroethylene there may be mentioned in particular trans-1,2-dichloroethylene, cis-1, 2 dichloroethylene.
  • Trans-1, 2-dichloroethylene is advantageously chosen.
  • fluoroamines there may be mentioned in particular N- (difluoromethyl) -N, N-dimethylamine,
  • hydro fluorothioethers mention may in particular be made of 1,1,1,2,2-pentafluoro-2 - [(pentafluoroethyl) thio] ethane.
  • An example of a cyclic (hydro) fluorocarbon is heptafluorocyclopentane.
  • 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.
  • Ri 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.
  • the 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, 1, 2,4,4,5,5-octafluoro-2-
  • bromofluoro ketones for example monobromoperfluoro ketones, monohydromonobromoperfluoro ketones, (perfluoroalkoxy) monobromoperfluoro ketones, (fluoroalkoxy) monobromoperfluoro ketones and monochloromonobromoperfluoro ketones.
  • 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 trans -1,2-dichloroethylene and at least one hydrofluoroether.
  • An expanding agent composition comprising trans-1,2-dichloroethylene and 1-methoxy nonafluorobutane has given very interesting results.
  • a composition comprising trans -1,2-dichloroethylene and 1 ethoxy nonafluorobutane.
  • the blowing agent composition according to the present invention advantageously leads to thermoplastic and thermosetting foams having good dimensional stability. It is particularly suitable for the manufacture of 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 producing polyurethane foams, in particular rigid 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 Stepanpol PS2412 polyol (polyester type), 1.5 parts by weight of surfactant Tegostab B8465, 3 parts by weight of polyesters are introduced into a beaker. water and 10 parts by weight of the blowing agent composition 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). After stirring for 25 seconds (total), 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.
  • Dabco K15 mixture of potassium salt 2-ethyl hexanoic acid and diethylene glycol
  • the volume of the cut foam is measured before passing to the oven and after
  • 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 trans 1, 2-dichloroethylene (TDCE) and 25% by weight of 1-methoxy-nonafluorobutane.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Polyurethanes Or Polyureas (AREA)
EP07731825A 2006-03-31 2007-03-26 Blähmittelzusammensetzung Withdrawn EP2024431A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0602797A FR2899234B1 (fr) 2006-03-31 2006-03-31 Composition d'agent d'expansion
US80046406P 2006-05-15 2006-05-15
PCT/FR2007/051013 WO2007113435A2 (fr) 2006-03-31 2007-03-26 Composition d'agent d'expansion

Publications (1)

Publication Number Publication Date
EP2024431A2 true EP2024431A2 (de) 2009-02-18

Family

ID=37591711

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07731825A Withdrawn EP2024431A2 (de) 2006-03-31 2007-03-26 Blähmittelzusammensetzung

Country Status (10)

Country Link
US (1) US20100174008A1 (de)
EP (1) EP2024431A2 (de)
JP (1) JP2009535432A (de)
KR (1) KR20090012211A (de)
CN (1) CN101679661A (de)
AU (1) AU2007232416A1 (de)
CA (1) CA2643856A1 (de)
FR (1) FR2899234B1 (de)
MX (1) MX2008012351A (de)
WO (1) WO2007113435A2 (de)

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EP2109662B1 (de) 2007-02-06 2015-09-30 Solvay Fluor GmbH Nichtentflammbare zusammensetzung mit fluorinierten verbindungen und verwendung dieser verbindungen
FR2921665A1 (fr) * 2007-09-28 2009-04-03 Arkema France Composition a base de trans-1,2 dichloroethylene.
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CN104448377A (zh) * 2014-12-10 2015-03-25 江苏蓝色星球环保科技股份有限公司 一种含有1,2-二氯乙烯和二氟二氯乙烯的发泡剂组合物
CN104448226A (zh) * 2014-12-10 2015-03-25 江苏蓝色星球环保科技股份有限公司 一种含有1,2-二氯乙烯的发泡剂组合物
CN105968400A (zh) * 2016-06-04 2016-09-28 王金明 一种用作聚氨酯发泡剂的组合物
KR102258805B1 (ko) * 2019-06-26 2021-05-31 한국가스공사 경질 우레탄 폼 및 이의 제조방법
KR102397239B1 (ko) * 2020-04-22 2022-05-12 강대권 폴리우레탄 발포제 조성물 및 이를 이용한 폴리우레탄 발포체의 제조방법
US20250075027A1 (en) * 2023-09-03 2025-03-06 Kingspan Holdings (Irl) Limited Polyurethane Foams And Methods Of Manufacture Thereof

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Also Published As

Publication number Publication date
JP2009535432A (ja) 2009-10-01
KR20090012211A (ko) 2009-02-02
CN101679661A (zh) 2010-03-24
AU2007232416A1 (en) 2007-10-11
WO2007113435A2 (fr) 2007-10-11
FR2899234B1 (fr) 2017-02-17
MX2008012351A (es) 2009-03-06
FR2899234A1 (fr) 2007-10-05
CA2643856A1 (fr) 2007-10-11
WO2007113435A3 (fr) 2009-12-10
US20100174008A1 (en) 2010-07-08

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