WO2006114776A1 - Surfactant for phenolic foam - Google Patents
Surfactant for phenolic foam Download PDFInfo
- Publication number
- WO2006114776A1 WO2006114776A1 PCT/IE2005/000044 IE2005000044W WO2006114776A1 WO 2006114776 A1 WO2006114776 A1 WO 2006114776A1 IE 2005000044 W IE2005000044 W IE 2005000044W WO 2006114776 A1 WO2006114776 A1 WO 2006114776A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- castor oil
- phenolic foam
- moles
- surfactant
- phenolic
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 82
- 239000006260 foam Substances 0.000 title claims abstract description 80
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 38
- 235000004443 Ricinus communis Nutrition 0.000 claims abstract description 37
- 239000004359 castor oil Substances 0.000 claims abstract description 34
- 235000019438 castor oil Nutrition 0.000 claims abstract description 34
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 34
- 230000035699 permeability Effects 0.000 claims abstract description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 10
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 22
- 229920001568 phenolic resin Polymers 0.000 claims description 22
- 239000005011 phenolic resin Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 13
- 239000004604 Blowing Agent Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 239000004014 plasticizer Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 2
- 238000009413 insulation Methods 0.000 abstract description 17
- 229940117927 ethylene oxide Drugs 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- -1 polyoxyethylene Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 229920003987 resole Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 210000000497 foam cell Anatomy 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OBUNLFQVPAABFB-UHFFFAOYSA-N ethoxyethane;heptane Chemical compound CCOCC.CCCCCCC OBUNLFQVPAABFB-UHFFFAOYSA-N 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
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
- C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
-
- 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
- C08J9/16—Making expandable particles
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- 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
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- 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
- C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
Definitions
- This invention relates to a surfactant for phenolic foam, phenolic foam products and a process for producing phenolic foam.
- Phenolic foam is used in insulation applications for construction materials because of its superior thermal insulation and fire resistance characteristics.
- phenolic foam cell size is fine, and that it has closed cell structure to enhance the thermal insulation performance of phenolic foam products.
- surfactant needs to be present to act as a cell stabilisation agent.
- ethylene oxide is referred to as EO.
- JP-A-61 -268733 describes a castor oil-EO adduct in which 2 to 20 moles of EO is added to 1 mole of castor oil.
- JP-A-63-039933 describes a castor oil-EO adduct in which 40 to 90 moles of EO is added to 1 mole of castor oil.
- the thermal insulation performance of the phenolic foam obtained is inferior. Moreover, if the ratio of the number of moles of EO added per mole of castor oil in the adduct varies slightly, the thermal insulation performance of the phenolic foam obtained can vary significantly.
- the phenolic foam obtained has a higher moisture permeability coefficient.
- the cost of producing the castor oil-EO adduct not only is higher because of the use of the higher molar number of the EO added, but also the thermal insulation performance of the phenolic foam obtained is inferior and its moisture permeability coefficient becomes higher.
- An objective of the present invention is to provide a surfactant for phenolic foam that overcomes the above-mentioned problems. Additionally, an objective of the present invention is to provide a process for efficiently producing the said phenolic foam in which the surfactant is used.
- a castor oil-EO adduct has more than 20 moles but less than 40 moles of EO added per 1 mole of castor oil and such an adduct is employed as a surfactant, the phenolic foam so obtained has improved thermal insulation performance.
- the thermal insulation performance of the phenolic foam obtained does not greatly vary, and additionally the moisture permeability coefficient of the phenolic foam is kept low.
- the present invention is based on such findings. According to the invention there is provided a surfactant for phenolic foam characterised by a castor oil-ethylene oxide adduct wherein more than 20 moles but less than 40 moles of ethylene oxide are added per 1 mole of castor oil
- the invention also provides a phenolic foam comprising phenolic resin, blowing agent, surfactant and catalyst, characterised in that the surfactant is a castor oil- ethylene oxide adduct wherein more than 20 moles but less than 40 moles of ethylene oxide are added to 1 mole of castor oil
- the content of the castor oil-ethylene oxide adduct may be from 1 to 5 parts by weight relative to 100 parts by weight of the phenolic resin.
- the phenolic foam may be prepared by curing a phenolic resin in which the molar ratio of phenol to formaldehyde is typically between 1 : 1.5 and 1 : 2.5; the weight average molecular weight is in the range from 700 to 2,000; and the number average molecular weight is in the range from 300 to 700
- the thermal conductivity of the phenolic foam is preferably equal to or less than 0.022 W/m.K
- the moisture permeability coefficient for a thickness of 25mm is preferably not more than 60 ng/(m 2 .s.Pa).
- the invention also provides a process for producing phenolic foam by preparing a foamable phenolic resin composition that comprises phenolic resin, surfactant, plasticiser, blowing agent, and catalyst, delivering the resin composition onto a continuously running substrate, and passing through a heated zone to produce phenolic foam as the phenolic foam is moulded into a predetermined shape.
- the phenolic foam is characterised in that the surfactant used is a castor oil-ethylene- oxide adduct wherein more than 20 moles but less than 40 moles of ethylene oxide are added to 1 mole of castor oil.
- the surfactant of the present invention is a castor oil-EO adduct that is obtained by adding more than 20 moles but less than 40 moles of EO to 1 mole of castor oil.
- the surfactant has a hydrophobic segment mainly comprising a long hydrocarbon chain from castor oil and a hydrophilic segment mainly comprising polyoxyethylene (EO) chemical linkages. It is presumed that a well-balanced molecular structure formed from both the hydrophobic and the hydrophilic segment optimises the surface activity of the surfactant, helps make phenolic foam cell diameter small, and the cell walls of the phenolic foam more flexible. Thereby cracks in the cell walls are less likely to occur.
- the thermal insulation performance of the phenolic foam obtained does not vary greatly. Additionally, the permeability coefficient of the phenolic foam remains low.
- the surfactant of the present invent is characterised by the castor oil-EO adduct in which more than 20 moles but less than 40 moles of EO are added to 1 mole of castor oil.
- Castor oil is a non-drying oil derived from seeds of castor oil beans that contain a relatively large amount of unsaturated acids such a ricinoleic acid, oleic acid, and linoleic acid and a small amount of saturated acids such as stearic acid and dioxystearic acid. To 1 mole of this castor oil are added more than 20 moles but less than 40 moles of EO.
- the surfactant when the molar number of EO is more than 20 moles, but less than 40 moles, and this is added to 1 mole of castor oil, then a well-balanced molecular structure of hydrophobic, long chain hydrocarbon castor oil with hydrophilic EO segments is obtained.
- the surfactant then has favourable surface activity.
- the effect of using this surfactant is that cell diameter of the phenolic foam is kept fine, flexibility is imparted to the cell walls of the phenolic foam and crack occurrence in the cell walls can be prevented.
- a preferred molar number of EO to add to 1 mole of castor oil is between 21 and 38.
- the surfactant of the present invention may be used either alone or in combination with another surfactant. Examples of other surfactants that may be used are shown later.
- the phenolic foam comprises phenolic resin, blowing agent, surfactant and a catalyst and is characterised in that the surfactant used is a castor oil-ethylene oxide adduct wherein more than 20 moles but less than 40 moles of ethylene oxide are added to 1 mole of castor oil.
- a preferred phenolic resin used in the present invention is a resole resin (hereinafter, referred also to as phenolic resin material) that is obtained by the reaction of a phenol such as cresol, xylenol, para-alkylphenol, para-phenylphenol, resorcinol, and the like with an aldehyde such as formaldehyde, paraformaldehyde, furfural, acetaldehyde and the like under a catalytic amount of an alkali such as sodium hydroxide, potassium hydroxide, calcium hydroxide, or aliphatic amines like trimethylamine, and triethylamine.
- phenol such as cresol, xylenol, para-alkylphenol, para-phenylphenol, resorcinol, and the like
- an aldehyde such as formaldehyde, paraformaldehyde, furfural, acetaldehyde and the like
- an alkali
- the molar ratio of phenol groups to aldehyde is not especially limited. It is preferable that the molar ratio of phenol to an aldehyde is from 1 : 1 to 1 : 3, more preferably from 1.5 to 2.5, and particularly preferable approximately 1 : 2.
- a preferable molecular weight for a phenolic resin material is from 400 to 3,000, and more preferably from 700 to 2,000 in terms of weight average molecular weight. On the other hand, the number average molecular weight is from 150 to 1,000, and more preferably from 300 to 700. Blowing agent selection is not especially limited and blowing agents in the public domain are employed in the present invention.
- saturated aliphatic hydrocarbons with low boiling points such as butane, pentane, hexane, or heptane ether such as isopropyl ether a fluoride-containing hydrocarbon compound such as trichloromonofluoromethane, trichlorotrifluoroethane or a mixture thereof.
- the castor oil-EO adduct mentioned above in which more than 20 moles but less than 40 moles of EO is added to 1 mole of castor oil, is employed is an essential component of the present invention.
- a dimethyl polysiloxane-polyoxy alkylene copolymer like dimethyl polysiloxane-polyoxy ethylene copolymer, or a castor oil-polypropylene oxide adduct and so on may be used.
- an inorganic acid such as sulphuric acid or phosphoric acid
- an organic acid such as benzene sulfonic acid, xylene sulfonic acid, paratoluene sulfonic acid, naphthol sulfonic acid, phenol sulfonic acid and so on are used.
- a plasticiser may be present the phenolic foam of the present invention such as a sulfonamide, a polyester polyol and the like.
- the weight addition of the castor oil-EO adduct relative to 100 parts by weight of phenolic foam is preferably from 1 to 5 parts by weight, and more preferably from 2 to 4 parts by weight. If the content of the castor oil-EO adduct is less than 1 part by weight, uniform cells cannot be obtained in the foam. On the other hand, if more than 5 parts by weight of the castor oil-EO adduct is used, the production cost and the water-absorbing capacity of the foam is increased.
- the phenolic foam of the present invention has a thermal conductivity of under 0.022 W/m.K preferably. Phenolic foam with a thermal conductivity more than 0.022 W/m.K is less efficient in terms of thermal insulation performance.
- the phenolic foam preferably has a moisture permeability coefficient of below 60 ng/(m 2 .s.Pa) for a thickness of 25mm. Phenolic foam with a moisture permeability coefficient above 60 ng/(m 2 .s.Pa) for a thickness of 25mm is undesirable.
- the facing materials used are not limited. They can be fibrous materials. They include a non-woven fabric, paper and the like made from a natural fibre, synthetic fibre, inorganic fibre, etc.
- the facing materials can also be metallic or plastic foils or sheets, with or without a suitable primer coating or fibrous interlayer to enhance adhesion.
- a process for producing phenolic foam comprises preparing a foamable phenolic resin composition that includes phenolic resin, surfactant, plasticiser, blowing agent, and a catalyst.
- the foam is characterised in that the surfactant present is a castor oil-ethylene oxide adduct in which more than 20 moles but less than 40 moles of EO are added to 1 mole of castor oil.
- the described castor oil-EO adduct surfactant is then added to the phenolic resin composition.
- a plasticiser such as polyester polyol is optionally mixed into the phenolic resin also.
- the phenolic resin composition obtained is pumped to a high speed mixer head where it is introduced to and mixed with blowing agent and acid catalyst to prepare a foamable phenolic composition.
- the said foamable phenolic resin composition is discharged on to a running carrier and passed through a heated zone for foaming and moulding into the desired phenolic foam products.
- the said resin composition is discharged on to a running conveyor belt into the heated oven typically at 60 to 100°C for approximately 2 to 15 minutes.
- the top of the foaming composition is pressed down with another conveyer belt, while the thickness of the foam is controlled to the required predetermined thickness.
- the phenolic foam leaving the oven is then cut to a predetermined length.
- the phenolic foam of the present invention is formed and moulded by using the following processes in which the said foamable phenolic resin composition thus prepared is (1) discharged on to a continuous conveyer, (2) warmed and foamed partially, (3) placed in a pressurised mould, (4) discharged into a mould to give a foaming block, or (5) charged into one or more of closed cavities under high pressure and so on.
- TC Thermal Conductivity
- a test piece of length 300 mm and width 300mm was placed between a high temperature plate with a temperature of 30°C and a low temperature plate with a temperature of 10°C in a thermal conductivity test instrument (Type HC-074 304, Koei Seiki Co., Ltd.) in which the thermal conductivity, TC, of the test pieces was measured according to JIS A 1412.
- MPC Moisture Permeability Coefficient
- test pieces Three disc shape test pieces are cut from a phenolic foam board with a thickness of 25mm and a diameter of 65 mm.
- the dimension of the test piece had an accuracy of 0.1 mm and the moisture permeability area of water vapour was calculated as 0.05 cm2.
- Moisture permeability coefficient, (MPC) for a thickness of 25mm is
- ml, m2 is the weight (ng) each for time Tl or time T2
- Tl, T2 is the time (s) each of the weight ml or m2
- A is the moisture permeability area (m2) of water vapour of each test piece
- P2 is the vapour pressure (1404.4 Pa) of a thermostatic tank
- t is the thickness (mm) of a test piece
- castor oil- EO adduct in which 22 moles of EO had been added to one mole of castor oil.
- castor oil- EO adducts were obtained in which 10, 30, 37, 50 or 75 moles of EO had been added to 1 mole of castor oil.
- PF-329 ( molar ratio of phenol : formaldehyde is 1 : 2.0, weight average molecular weight 1400, and number average molecular weight 500, produced by Asahi Organic Chemicals Industry Co.
- the resin blend is pumped to a high speed mixer and 20 parts by weight of a mixture of para-toluene sulfonic acid and xylene sulfonic acid ( weight ratio was 2 :1) as a catalyst and 8 parts by weight of pentane as a blowing agent, are added to give a foamable phenolic resin composition.
- the resin composition is discharged into a moulding frame laid with a glass fibre non-woven fabric. Foaming commenced, and the sample was held at 80°C for 10 minutes hours in an oven to give cured phenolic foam.
- the dimensions of the foam sample obtained are 300mm length, 300mm width and 25mm thickness.
- Example 2 A phenolic foam was prepared by the same manner as in Example 1 except that the molar number of the EO used was changed to 30.
- a phenolic foam was prepared by the same manner as in Example 1 except that the molar number of the EO used was changed to 37. Comparative Example 1
- a phenolic foam was prepared by the same manner as in Example 1 except that the molar number of the EO used was changed to 10.
- a phenolic foam was prepared by the same manner as in Example 1 except that the molar number of the EO used was changed to 50.
- Comparative Example 3 A phenolic foam was prepared by the same manner as in Example 1 except that the molar number of the EO used was changed to 75.
- Comparative Examples 1 to 3 show thermal conductivity within the range 0.0230 to 0.0280 W/m.K. These results are for castor oil-EO adducts in which 10, 50, or 75 moles each of EO had been added to 1 mole of castor oil.
- the thermal conductivity results for Comparative Examples 1 to 3 are inferior to results found for Examples 1 to 3.
- Examples 1 to 3 corresponding to castor oil-EO adducts in which 20, 30, or 37 moles each of EO were added to 1 mole of castor oil have a low moisture permeability coefficient per 25mm thickness that is within the range 40 to 43 ng/(m 2 .s.Pa). This means that each foam sample was satisfactory in terms of moisture permeability coefficient as well as for thermal conductivity.
- the respective moisture permeability coefficient values were higher within the range 65 to 70 ng/(m 2 .s.Pa).
- the molar number of EO in an castor oil-EO adduct should be more than 20 moles but less than 40 moles of EO relative to 1 mole of castor oil to obtain optimised thermal conductivity.
- Phenolic foam in which the castor oil-EO adduct of the present invention is used as a surfactant provides favourable thermal insulation performance. Even though the molar addition number of EO to castor oil is varied, the thermal insulation performance of the phenolic foam obtained does not vary greatly. Further, having a low moisture permeability coefficient, the phenolic foam of the present invention is suitable for use in the field of construction materials
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)
- Emergency Medicine (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IE2005/000044 WO2006114776A1 (en) | 2005-04-27 | 2005-04-27 | Surfactant for phenolic foam |
EP05734800A EP1874855A1 (en) | 2005-04-27 | 2005-04-27 | Surfactant for phenolic foam |
CN2005800499108A CN101184800B (en) | 2005-04-27 | 2005-04-27 | Surfactant for phenolic foam |
GB0723086A GB2440493B (en) | 2005-04-27 | 2005-04-27 | Surfactant for phenolic foam |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IE2005/000044 WO2006114776A1 (en) | 2005-04-27 | 2005-04-27 | Surfactant for phenolic foam |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006114776A1 true WO2006114776A1 (en) | 2006-11-02 |
Family
ID=34965393
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IE2005/000044 WO2006114776A1 (en) | 2005-04-27 | 2005-04-27 | Surfactant for phenolic foam |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1874855A1 (en) |
CN (1) | CN101184800B (en) |
GB (1) | GB2440493B (en) |
WO (1) | WO2006114776A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130072589A1 (en) * | 2005-09-08 | 2013-03-21 | Kingspan Holdings (Irl) Limited | Phenolic foam |
US20130072590A1 (en) * | 2005-09-08 | 2013-03-21 | Kingspan Holdings (Irl) Limited | Phenolic foam |
EP2345692B1 (en) * | 2008-11-07 | 2018-10-31 | Asahi Kasei Construction Materials Corporation | Expandable phenolic resin composition, phenolic resin foam, and process for producing the phenolic resin foam |
WO2022043561A1 (en) * | 2020-08-31 | 2022-03-03 | Kingspan Holdings (Irl) Limited | Phenolic foam |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4270510A (en) * | 1978-07-28 | 1981-06-02 | Kokusan Denki Co., Ltd. | Ignition system for an internal combustion engine |
US4530939A (en) * | 1982-02-11 | 1985-07-23 | The Dow Chemical Company | Low K-factor closed cell phenol-aldehyde foam and process for preparation thereof |
US6566308B1 (en) * | 1999-01-29 | 2003-05-20 | Basf Aktiengesellschaft | Emulsifiable concentrate containing one or more pesticides and adjuvants |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9912476D0 (en) * | 1999-05-28 | 1999-07-28 | Novartis Ag | Organic compounds |
CN1178971C (en) * | 2001-12-26 | 2004-12-08 | 广州擎天新材料研究开发有限公司 | Phenolic foam plastic composite product and its production and forming process |
-
2005
- 2005-04-27 EP EP05734800A patent/EP1874855A1/en not_active Withdrawn
- 2005-04-27 CN CN2005800499108A patent/CN101184800B/en active Active
- 2005-04-27 WO PCT/IE2005/000044 patent/WO2006114776A1/en not_active Application Discontinuation
- 2005-04-27 GB GB0723086A patent/GB2440493B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4270510A (en) * | 1978-07-28 | 1981-06-02 | Kokusan Denki Co., Ltd. | Ignition system for an internal combustion engine |
US4530939A (en) * | 1982-02-11 | 1985-07-23 | The Dow Chemical Company | Low K-factor closed cell phenol-aldehyde foam and process for preparation thereof |
US6566308B1 (en) * | 1999-01-29 | 2003-05-20 | Basf Aktiengesellschaft | Emulsifiable concentrate containing one or more pesticides and adjuvants |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130072589A1 (en) * | 2005-09-08 | 2013-03-21 | Kingspan Holdings (Irl) Limited | Phenolic foam |
US20130072590A1 (en) * | 2005-09-08 | 2013-03-21 | Kingspan Holdings (Irl) Limited | Phenolic foam |
US8765829B2 (en) * | 2005-09-08 | 2014-07-01 | Kingspan Holdings (Irl) Limited | Phenolic foam |
US8772366B2 (en) * | 2005-09-08 | 2014-07-08 | Kingspan Holdings (Irl) Limited | Phenolic foam |
EP2345692B1 (en) * | 2008-11-07 | 2018-10-31 | Asahi Kasei Construction Materials Corporation | Expandable phenolic resin composition, phenolic resin foam, and process for producing the phenolic resin foam |
WO2022043561A1 (en) * | 2020-08-31 | 2022-03-03 | Kingspan Holdings (Irl) Limited | Phenolic foam |
Also Published As
Publication number | Publication date |
---|---|
GB2440493B (en) | 2010-03-10 |
GB0723086D0 (en) | 2008-01-02 |
CN101184800B (en) | 2011-04-27 |
EP1874855A1 (en) | 2008-01-09 |
CN101184800A (en) | 2008-05-21 |
GB2440493A (en) | 2008-01-30 |
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