JPS6354539B2 - - Google Patents
Info
- Publication number
- JPS6354539B2 JPS6354539B2 JP1804182A JP1804182A JPS6354539B2 JP S6354539 B2 JPS6354539 B2 JP S6354539B2 JP 1804182 A JP1804182 A JP 1804182A JP 1804182 A JP1804182 A JP 1804182A JP S6354539 B2 JPS6354539 B2 JP S6354539B2
- Authority
- JP
- Japan
- Prior art keywords
- flame
- equivalent
- laminate
- resistant
- urethane foam
- 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.)
- Expired
Links
- 239000006260 foam Substances 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 29
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 20
- -1 alkylene carbonate Chemical compound 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 10
- 239000010425 asbestos Substances 0.000 claims description 10
- 229910052895 riebeckite Inorganic materials 0.000 claims description 10
- 239000005011 phenolic resin Substances 0.000 claims description 9
- 238000005187 foaming Methods 0.000 claims description 8
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000011347 resin Substances 0.000 description 23
- 229920005989 resin Polymers 0.000 description 23
- 239000007788 liquid Substances 0.000 description 19
- 239000003063 flame retardant Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
- 239000011162 core material Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 5
- 235000019256 formaldehyde Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920000582 polyisocyanurate Polymers 0.000 description 3
- 239000011495 polyisocyanurate Substances 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- QYIOFABFKUOIBV-UHFFFAOYSA-N 4,5-dimethyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1C QYIOFABFKUOIBV-UHFFFAOYSA-N 0.000 description 1
- DAUVWNSVSAPZET-UHFFFAOYSA-N 4-butyl-1,3-dioxol-2-one Chemical compound CCCCC1=COC(=O)O1 DAUVWNSVSAPZET-UHFFFAOYSA-N 0.000 description 1
- IXIDQWJXRMPFRX-UHFFFAOYSA-N 4-ethyl-1,3-dioxol-2-one Chemical compound CCC1=COC(=O)O1 IXIDQWJXRMPFRX-UHFFFAOYSA-N 0.000 description 1
- RUPLNLKUIZWBSB-UHFFFAOYSA-N 4-pentyl-1,3-dioxol-2-one Chemical compound CCCCCC1=COC(=O)O1 RUPLNLKUIZWBSB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- WDPYDDUVWLUIDM-UHFFFAOYSA-N ethyl carbamate;phenol Chemical compound CCOC(N)=O.OC1=CC=CC=C1 WDPYDDUVWLUIDM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- MVAOEXBRERPGIT-UHFFFAOYSA-N octamine Chemical compound N.N.N.N.N.N.N.N MVAOEXBRERPGIT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Laminated Bodies (AREA)
Description
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The present invention relates to a flame-resistant laminate, particularly a laminate having a core material of phenolic urethane foam, which has excellent heat resistance, dimensional stability, and the like. Conventionally, laminates have been used for ceiling materials, wall materials, and other construction materials, with a core material such as wood or plaster and a facing material such as decorative paper or iron plate, but these materials are generally heavy and have difficulty in construction. It also has the disadvantages of being hygroscopic and having low heat insulation properties. On the other hand, materials having core materials made of lightweight organic foams such as rigid polyurethane foams with good heat insulation properties have been developed, but these materials generally have the disadvantage of low fire retardant performance. A laminate with a polyisocyanurate foam as a core material and aluminum foil or plate-like material as a face material is known as a laminate with high fire retardant performance that uses an organic foam as a core material. In order to pass the flame retardant class 2 test described below, a considerable amount of flame retardant, smoke reducer, or inorganic material is added to the polyisocyanurate foam, which reduces the physical properties of the foam such as heat insulation and dimensional stability. This is unavoidable, and it is economically disadvantageous because the aluminum foil or plate-like material to be attached must have a thickness of 0.1 mm or more to be effective. The present invention uses a phenolic urethane foam manufactured using a special polyol component, removes all flame retardants from the conventional rigid urethane foam foam formulation, passes the flame retardant grade 2 test, and is inexpensive. To provide a flame-resistant laminate that can be produced by a method suitable for industrial productivity. That is, the present invention provides a laminate in which at least one side of a urethane foam is coated with a flame-resistant face material, in which the urethane foam is (a) a benzyl ether type obtained by condensing formaldehyde in an equimolar or more amount to phenol; The phenolic hydroxyl group of phenolic resin
A modified phenol resin in which 0.3 equivalent or more has been converted into alcoholic hydroxyl groups with alkylene carbonate and (b) polyisocyanate are subjected to a foaming reaction in the range of NCO equivalent/OH equivalent âŠ2,
This relates to a flame-resistant laminate that is self-adhered onto the facing. The benzyl ether type phenolic resin in the present invention is prepared by using alkaline earth metal oxides, hydroxides, or organic weak acid salts such as acetic acid and naphthenic acid alone or under conditions of 1 mole or more of formaldehyde per 1 mole of phenols. , obtained by reaction under a mixed catalyst. The phenols referred to herein mean those in which one or more carbon atoms of the skeleton forming a benzene ring are directly bonded to a hydroxyl group, and also include those having other substituted bonding groups within the same structure. Typical examples include phenol, cresol, bisphenol A, and resorcinol. Further, formaldehydes are not particularly limited, but formalin and paraformaldehyde are preferred. Furthermore, the alkylene carbonate used in the present invention has the general formula: (However, R and R' are hydrogen or an alkyl group having 1 to 6 carbon atoms.) Specifically, for example, ethylene carbonate, propylene carbonate, 4-ethyl dioxolone, 4-butyl dioxolone, 4 , 5-dimethyldioxolone, 4-pentyldioxolone, 4,4'-dimethyldioxolone, etc. are used. Next, the amount of conversion of phenolic hydroxyl groups in the resin to alcoholic hydroxyl groups is as follows:
The amount is 0.3 equivalent or more, preferably 0.4 to 0.8 equivalent. If the conversion amount is 0.3 equivalent or less, the modification effect will not be exhibited. Note that if alkylene carbonate is used in excess of the equivalent amount of phenolic hydroxyl groups, unreacted alkylene carbonate or hydrolyzed glycol will be produced, which will deteriorate the heat resistance of the final cured phenol urethane product and reduce the reaction rate during curing. The object of the present invention cannot be achieved because of the delay. In the present invention, the conversion reaction of a phenolic hydroxyl group into an alcoholic hydroxyl group is carried out by adding and mixing alkylene carbonates while keeping the benzyl ether type phenolic resin, which has been concentrated in advance through a condensation reaction and a dehydration reaction, in a non-aqueous system. Not
A suitable alkaline catalyst is added at a temperature not exceeding 140°C, and the reaction is allowed to occur for several minutes to several hours. As the alkaline catalyst for denaturation, catalysts such as potassium carbonate, sodium carbonate, and calcium carbonate that open the ring of alkylene carbonate and do not generate glycol are preferable.By using these catalysts, alkylene carbonate can generate carbon dioxide gas. While doing so, the ring opens, forming an ether bond with the phenolic hydroxyl group, and the hydroxyl group is modified. The obtained modified resin is further removed under reduced pressure to remove unreacted carbonate monomers and by-produced glycol monomers, as necessary, to obtain a product. used in liquids. The polyisocyanates used in the present invention are not particularly limited, and any conventionally and commonly used polyisocyanates may be used as appropriate. Typical examples include aromatic polyisocyanates such as tolylene diisocyanate, diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, etc.
Examples include aliphatic polyisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, and the like. Particularly preferred are diisocyanates. The reaction ratio between the modified phenolic resin and the polyisocyanate is in the range of NCO equivalent/OH equivalentâŠ2, preferably 1.2 to 1.8. When NCO equivalent/OH equivalent exceeds 2, flyability increases. The OH equivalent here refers to phenolic and alcoholic
It concerns the total OH. Both reactions are usually carried out in the presence of a curing catalyst, foam stabilizer and blowing agent. As curing catalysts, amine catalysts such as triethylenediamine, N,N-dimethylethanolamine, N,N,N',N',N''-pentamethyldiethylenetriamine, etc., organotin catalysts such as dibutyltin dilaurate, stannous octamine, etc. ate, dibutyltin diacetate, etc. These curing catalysts are used in an amount of 0 to 10% by weight of the modified phenolic resin. The blowing agent is not limited, and general blowing agents for urethane foam can be used as they are. Specifics Examples include chlorofluorinated hydrocarbons such as trichloromonofluoromethane and dichlorodifluoromethane, and others.
Examples include methylene chloride and pentane. Examples of foam stabilizers include nonionic surfactants such as organopolysiloxane-polyoxyalkylene copolymers and silicone-glycol copolymers. The urethane foam used in the present invention is bonded to a flame-resistant face material. The flame-resistant surface material may be any flame-resistant material such as asbestos paper, glass paper, aluminum foil, various flame-resistant laminate papers, and gypsum flat boards, but asbestos paper is particularly preferred. Asbestos paper has excellent self-adhesive properties with the above-mentioned urethane foam, and is lightweight and economical. The thickness of asbestos paper
Approximately 100 to 500 g/m 2 is suitable. In the present invention, the urethane foam and the flame-resistant surface material are self-adhesive. Self-adhesion is easily achieved by overlapping the urethane foam core material with the face material during formation, so there is no need to use a separate adhesive to bond the urethane foam core material and the face material, resulting in excellent industrial productivity. There is. At least one flame-resistant facing material shall be attached to any surface that may come into contact with flames. The urethane foam used in the present invention is itself extremely flame retardant and exhibits excellent flame retardancy without the use of special flame retardants, flame retardants or smoke reducers, but without the use of flame resistant face materials. It is not possible to obtain a product that passes the JIS-A-1321 flame retardant class 2 fire protection test. Conversely, even if asbestos paper or the like is used as a surface material to protect the surface of conventional hard urethane foam or polyisocyanurate foam, it will not pass the second class flame retardant test unless a large amount of flame retardant is used. In addition, the use of such flame retardants impairs the insulation properties and dimensional stability of the foam.
Moreover, mechanical properties are deteriorated. The present invention will be explained below with reference to Examples. Example 1 600 kg of phenol and 204 kg of 47% formalin
1.4 kg of lead naphthenate was added, the temperature was raised, and the mixture was reacted at 100 to 103°C for 4 hours. The obtained resin was introduced into a continuous concentrator with an L/D of 1000, and the outlet of the tube was placed in a flash chamber kept at 125°C while the jacket of the tube was heated with 3.5 kg/cm 2 of steam. guide the flash chamber.
The pressure was reduced to 60 mmHg, and while unreacted monomers and water were removed from the system, only the resin liquid was separately taken out of the system to obtain a benzyl ether type phenol resin liquid (hereinafter referred to as resin liquid A). Resin liquid A had the characteristics shown in Table 1.
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ãã[Table] Next, 260 kg of resin liquid A and 110 kg of ethylene carbonate were charged into a reaction vessel, 0.3 kg of K 2 CO 3 was added, and the mixture was reacted at 110°C for 50 minutes. As the reaction progresses, carbon dioxide gas is generated, so while removing it from the system,
After the reaction was completed, the monomer was removed under reduced pressure to obtain a modified resin (hereinafter referred to as resin liquid). Table 2 shows the properties of the resin liquid. Table 2 Viscosity (20â cps) 4200 OH number (mgKOH/g) 407 Average molecular weight 324 Nonvolatile content (%) 72 Moisture (%) 0.9 Free phenol (%) 4.9 Free formaldehyde (%) 0.1 Monomer and glycol in resin liquid When measured by gas chromatography, the content was 2% ethylene carbonate and 0% glycol, and the modification rate was 0.56 mol per mol of phenolic hydroxyl group. Incidentally, each item in the above examples was measured based on the following measuring method. Viscosity: Based on BH type viscometer. Free phenol...liquid chromatography free formaldehyde...by hydrochloric acid/hydroxylamine method. Nonvolatile content: 180°C x 1 hour Evaporation average molecular weight: Based on vapor pressure osmosis method. Methylol group/ether group...by IR method OH value...by acetylation method. Moisture: According to the Karl-Fitscher method. Methylol group equivalent: 10 g of phenolic resin and 20 g of phenol (containing 0.2 wt% PbO) were reacted at 115 to 120°C for 90 minutes, and after cooling, water was removed by the Karl Fischer method and free formalin was measured by the hydrochloric acid hydroxylamine method. Find it by (P+R)ÃRRWÃ10 -2 â(P+R)(RFâRRF)Ã18Ã
18 -2 /30-R x RW x 10 -2 x P x PW x 10 -2 /R x 18 x 100 P: Amount of added phenol (g) R: Amount of resin (g) RF: Free formalin in resin (% ) RW: Moisture in resin (%) PW: Moisture in added phenol (%) RRF: Free formalin in reactant (%) RRW: Moisture in reactant (%) Next, using this resin liquid, in formulation A. A board was prepared by free foaming in a box and foaming in a mold according to recipe B. These foam physical property values are shown in Table 3. Prescription A Parts by weight Resin liquid 100 T-12 0.3 L-5420 1.5 S-1 16 MR-200 NCO equivalent/OH equivalent = 1.2 Prescription B Parts by weight Resin liquid 100 T-12 0.3 L-5420 1.5 S-1 60 MR- 200 NCO equivalent/OH equivalent = 1.2 Here, T-12 is a product of M&T Chem Co., Ltd. Dibutyltin dilaurate L-5420 is a product of Nippon Unicar Co., Ltd. Organopolysiloxane polyoxyalkylene copolymer S-1 is a product of Daikin Industries Co., Ltd. Daiflon S-
1; Trichloromonofluoromethane MR-200 is a product of Nippon Polyurethane Kogyo Co., Ltd. Crude diphenylmethane diisocyanate (Millionate MR200) NCO content 31% Free foaming in the box is achieved after high-speed stirring for approximately 10 seconds at a blending ratio of 200 g of resin liquid. , placed in a 25cm square box and allowed to foam freely. Also, when creating a board in a mold, the mixing ratio is approximately 20g of resin liquid.
After stirring at high speed for 10 seconds, place in a 30cm x 30cm x 20mm mold preheated to approximately 55â, place a top lid preheated to approximately 55â, secure the mold and lid firmly with clamps, and place the mold into a mold. It was created by foaming inside.
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MRâ200 NCOåœéïŒOHåœéïŒ1.6[Table] Next, in Examples 2 to 7, laminates using resin liquid will be introduced. Example 2 Aspal (asbestos paper manufactured by Jujo Paper Co., Ltd.) cut into 30 cm squares and heated to approximately 55°C in advance
100g/m 2 ) heated to approximately 55â in a mold (30cm in length and width,
(depth 20mm). A resin liquid prepared by formula C at a blending ratio of 20g of resin liquid,
Add a specified amount to the mixed solution of T-12, S-1, and L-5420.
Immediately after adding MR-200 and stirring at high speed for about 10 seconds, the mixed stock solution is poured into the mold. Place aspar that has been preheated to about 55°C above the injection stock solution, then place the top lid that has been preheated to about 55°C, and firmly fix the mold and the lid with a clamp. Leave it at room temperature for about 10 minutes, then remove it from the mold and make it 30cm x 30cm x
A 20 mm laminate was produced. The cross-sectional structure of the obtained laminate is shown in FIG. In the figure, 1 is asbestos paper,
2 shows a layer of phenolic urethane foam.
The combustion test results of this laminate are shown in Table 4. Formulation C Resin liquid I 100 parts by weight T-12 0.4 parts by weight L-5420 3 parts by weight S-1 60 parts by weight MR-200 NCO equivalent/OH equivalent = 1.6
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ççŒè©Šéšçµæãè¡šâïŒã«ç€ºããã[Table] Examples 3, 4 and 5 The following laminates were obtained in the same manner as in Example 2 except that the face material was changed. In Example 3, asparallel (100ÎŒ
Example 4 Laminate in which the polyethylene film layer was adhered to the urethane foam layer using
is a laminate (with the aluminum layer as the outermost layer) using aluminum foil (thickness 20Ό) laminated to aspar (100g/m 2 ) via polyethylene film (thickness 20Ό) as a face material. Example 5 is a laminate using aluminum with a thickness of 150 Όm as the face material. The combustion test results of these laminates are shown in Table 5.
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çµæãè¡šâïŒã«ç€ºããã[Table] Examples 6 and 7 In Example 6, the surface material is a 3mm thick flexible board made of cemented asbestos, and the back material is a 50ÎŒ
This is a laminate using glass paper (60 g/m 2 ) laminated with a thick polyethylene film. This configuration is shown in FIG. In the figure, 2 is a urethane foam layer, 3 is a polyethylene film layer, and 4 is a polyethylene film layer.
5 indicates a glass paper layer and 5 indicates a flexible plate. The manufacturing method is the same as in Example 2.
That is, a flexible plate was set in a mold, a mixed solution of prescription C was poured onto it, and a glass paper was set above the injection stock solution. Example 7 is a laminate using glass paper (60 g/m 2 ) laminated with a 9 mm thick gypsum flat board as the surface material and a 50 Ό thick polyethylene film as the back material (polyethylene film and urethane foam are bonded together). ). The manufacturing method is the same as in Example 6. The combustion test results of these laminates are shown in Table 6.
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ããçµæãè¡šâïŒã«ç€ºããã[Table] Example 8 The relationship between the modification ratio of a benzyl ether type phenolic resin modified with ethylene carbonate and the flyability of the foam was investigated. The modified phenolic resin was synthesized according to Example 1. On the other hand, the foam was obtained by free foaming in a box using Formulation D. These results are shown in Table-7. Formulation D Modified phenolic resin 100 parts by weight T-12 0.3 parts by weight L-5420 1.5 parts by weight S-1 25 parts by weight MR-200 NCO equivalent/OH equivalent = 1.2 Next, using the resin liquid, calculate the NCO equivalent and OH equivalent. Boards were prepared by in-mold foaming according to Example 1 with different ratios, and their flyability was examined. The results are shown in Table-8.
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[Table] Flyability: Rub the surface of the foam strongly with your fingers, and mark with an x if powder is generated, or mark with an â if it does not.
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[Table] Flyability: Rub the surface of the board strongly with your fingers, mark the item that generates powder with an
Items that do not survive are marked with â.
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ã å±€ãïŒã¯ããªãšãã¬ã³ãã€ã«ã ãïŒã¯ã¬ã©ã¹ã
ãŒããŒãïŒã¯ãã¬ãã·ãã«æ¿ã瀺ãã
FIGS. 1 and 2 are cross-sectional views of one embodiment of the flame-resistant laminate of the present invention. In the figure, 1 is asbestos paper, 2 is a urethane foam layer, 3 is a polyethylene film, 4 is glass paper, and 5 is a flexible board.
Claims (1)
ã®é¢æã§è¢«èŠããŠãªãç©å±€äœã«ãããŠã該ãŠã¬ã¿
ã³ããªãŒã ã (a) ããšããŒã«ã«å¯Ÿãçã¢ã«ä»¥äžã®ãã«ã ã¢ã«ã
ãããçž®ååå¿ãããŠåŸããããã³ãžã«ãšãŒã
ã«åããšããŒã«æš¹èã®ããšããŒã«æ§æ°Žé žåºã®
0.3åœé以äžãã¢ã«ãã¬ã³ã«ãŒãããŒãã«ãã€
ãŠã¢ã«ã³ãŒã«æ§æ°Žé žåºã«å€æããå€æ§ããšããŒ
ã«æš¹èãš (b) ããªã€ãœã·ã¢ããŒããšã NCOåœéïŒOHåœéâŠïŒ ã®ç¯å²ã§çºæ³¡åå¿ãããŠåŸããããã®ã§ãã€ãŠã
ãããé¢æäžã«èªå·±æ¥çããèçæ§ç©å±€äœã ïŒ èçæ§ã®é¢æãã¢ã¹ãã¹ãçŽã§ãã第ïŒé èš
èŒã®èçæ§ç©å±€äœã[Scope of Claims] 1. A laminate in which at least one side of a urethane foam is coated with a flame-resistant face material, wherein the urethane foam contains (a) benzyl obtained by condensing formaldehyde in an equimolar or more amount to phenol; The phenolic hydroxyl group of ether type phenolic resin
A modified phenol resin in which 0.3 equivalent or more has been converted into alcoholic hydroxyl groups with alkylene carbonate and (b) polyisocyanate are subjected to a foaming reaction in the range of NCO equivalent/OH equivalent âŠ2,
This is a flame-resistant laminate that is self-adhered to the surface material. 2. The flame-resistant laminate according to item 1, wherein the flame-resistant facing material is asbestos paper.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1804182A JPS58136432A (en) | 1982-02-06 | 1982-02-06 | Flame-retarded laminate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1804182A JPS58136432A (en) | 1982-02-06 | 1982-02-06 | Flame-retarded laminate |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58136432A JPS58136432A (en) | 1983-08-13 |
JPS6354539B2 true JPS6354539B2 (en) | 1988-10-28 |
Family
ID=11960591
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1804182A Granted JPS58136432A (en) | 1982-02-06 | 1982-02-06 | Flame-retarded laminate |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58136432A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4879164A (en) * | 1987-08-17 | 1989-11-07 | Arco Chemical Technology, Inc. | Laminated composite of a rigid polyisocyanurate substrate and metal, plastic, cellulose, glass, ceramic or combinations thereof |
-
1982
- 1982-02-06 JP JP1804182A patent/JPS58136432A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS58136432A (en) | 1983-08-13 |
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