JPH0126606B2 - - Google Patents
Info
- Publication number
- JPH0126606B2 JPH0126606B2 JP59114333A JP11433384A JPH0126606B2 JP H0126606 B2 JPH0126606 B2 JP H0126606B2 JP 59114333 A JP59114333 A JP 59114333A JP 11433384 A JP11433384 A JP 11433384A JP H0126606 B2 JPH0126606 B2 JP H0126606B2
- Authority
- JP
- Japan
- Prior art keywords
- foam
- iron
- polyurethane foam
- aromatic
- polyisocyanate
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 239000005056 polyisocyanate Substances 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 17
- 239000002994 raw material Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000000779 smoke Substances 0.000 claims description 11
- 229920005906 polyester polyol Polymers 0.000 claims description 10
- 239000003063 flame retardant Substances 0.000 claims 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 compound 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 claims description 6
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 6
- 239000011496 polyurethane foam Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 239000006260 foam Substances 0.000 description 41
- 238000000034 method Methods 0.000 description 21
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 150000002506 iron compounds Chemical class 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 10
- 239000004604 Blowing Agent Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 238000005187 foaming Methods 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- -1 dicyclopentadienyl iron Chemical compound 0.000 description 7
- 239000011550 stock solution Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000005829 trimerization reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
- 125000001931 aliphatic group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 2
- 229940099364 dichlorofluoromethane Drugs 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- KMHSUNDEGHRBNV-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carbonitrile Chemical class ClC1=NC=C(C#N)C(Cl)=N1 KMHSUNDEGHRBNV-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- CEQKTLFMTIWDBQ-UHFFFAOYSA-N C(C)[Fe](C1C=CC=C1)C1C=CC=C1 Chemical compound C(C)[Fe](C1C=CC=C1)C1C=CC=C1 CEQKTLFMTIWDBQ-UHFFFAOYSA-N 0.000 description 1
- CCZVCNIUOXTQRI-UHFFFAOYSA-N C(CCC)C=1C(C=CC=1)([Fe]C1C=CC=C1)CCCC Chemical compound C(CCC)C=1C(C=CC=1)([Fe]C1C=CC=C1)CCCC CCZVCNIUOXTQRI-UHFFFAOYSA-N 0.000 description 1
- FSJQZSFWCIVXKN-UHFFFAOYSA-N C(CCC)[Fe](C1C=CC=C1)C1C=CC=C1 Chemical compound C(CCC)[Fe](C1C=CC=C1)C1C=CC=C1 FSJQZSFWCIVXKN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 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
- 150000007513 acids Chemical class 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Phenolic Resins Or Amino Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
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"Industrial Application Field" The present invention relates to a method for producing urethane foam. Specifically, by using a polyhydroxy compound as a raw material in combination with specific compounds, it is possible to produce urethane foam with excellent heat resistance, flame retardancy, and low smoke emission. The present invention relates to a method for manufacturing urethane foam. Urethane foam is obtained in the process of polyurethane bond formation by reaction of polyisocyanate and polyhydroxy compound in the presence of a blowing agent, and is used for various purposes. In particular, when polyurethane foam is used for applications such as building materials, it is required to have various physical properties such as heat resistance, flame retardance, and low smoke emission. Heat resistance refers to the property of not causing thermal deformation such as shrinkage due to heat, low smoke emitting property refers to the property of producing a small amount of smoke when burned, and flame retardancy refers to the property of not causing thermal deformation such as shrinkage due to heat. These properties are mutually independent and important physical properties. ``Prior Art'' Various methods have been proposed to impart these properties to urethane foam. For example, flame retardation, particularly a highly flame retardant method, involves adding soluble iron compounds to the foam. A method of adding a silicone surfactant to the foam is known (Japanese Patent Application Laid-Open No. 53-72098), and in order to reduce smoke generation, 5% (by weight) of silicone surfactant is added to the foam.
It is also known to add more than
409). In addition to these methods, various modification methods have been proposed, but each method aims to maintain flame retardancy and reduce the brittleness of the foam, and each has its own advantages and disadvantages, and is still insufficient. It is not yet possible to achieve the desired effect. "Problems to be Solved by the Invention" The inventors of the present invention have conducted further intensive studies on the above-mentioned method in order to produce a urethane foam with better physical properties that combine heat resistance, flame retardance, and low smoke emission. As a result, various polyhydroxy compounds are used as raw materials for manufacturing urethane foam, but by using a specific polyhydroxy compound in combination with a specific additive, iron compounds soluble in the manufacturing solution can be used. The present invention was completed based on the novel finding that it is possible to produce a foam with excellent heat resistance and low smoke emission without impairing the flame retardant effect exhibited by the flame retardant effect. "Means for Solving the Problem" The object of the present invention is to provide a urethane foam that is excellent in heat resistance, flame retardancy, and low smoke emission. When manufacturing polyurethane foam using as the main manufacturing raw material, the polyhydroxy compound is derived from at least one aromatic compound selected from the group consisting of aromatic polyhydric carboxylic acids, carboxylic acid anhydrides, and carboxylic acid esters. 3% by weight or more of an aromatic polyester polyol, and 3% by weight of an organosilicon surfactant selected from an organopolysiloxane-polyoxyalkylene copolymer or a polyalkenylsiloxane having a polyoxyalkylene side chain. This can be easily achieved by using the above method and adding 0.05 to 10% (by weight) of a soluble iron compound to the production stock solution in terms of iron element. Hereinafter, the present invention will be explained in detail, and in this specification, weight % means the proportion in the production stock solution. An iron compound that is soluble in the production stock solution used in the method of the present invention is defined as an iron compound that dissolves at least 0.05% by weight in terms of iron when added to the production stock solution in which the reaction raw material and the blowing agent are mixed before foaming. Representative examples of these compounds include dicyclopentadienyl iron, mono- and di-lower alkyl (1 to 8 carbon atoms) dicyclopentadienyl iron,
For example, ethyldicyclopentadienyl iron, n-
Examples include dicyclopentadienyl iron compounds such as butyldicyclopentadienyl iron, di-n-butyldicyclopentadienyl iron, iron acetylacetonate, iron phthalocyanine compounds, iron chloride, etc., but other iron salts, Even iron coordination compounds are effective as long as they are soluble in the manufacturing solution. Among these, those that dissolve all of the added amount are more efficient. In addition, the production stock solution in this application means the production stock solution before foaming, which contains all raw materials such as polyisocyanate, polyhydroxy compound, blowing agent, catalyst added as necessary, foam stabilizer, and other auxiliary agents. . If the amount of iron compound added is too large, there is a problem that the inside of the foam will be burned (scorch occurs) immediately after foaming, and if it is too small, the flame retardant effect will be low. Therefore, the range of iron compounds is 0.05 to 0.05 of the foam manufacturing stock solution in terms of iron element.
10% by weight (the following percentages are by weight unless otherwise specified)
), and is preferably in the range of 0.35 to 7%, more preferably 0.5 to 5%. The organosilicon surfactant used in the present invention is selected from those widely used as surfactants for urethane foam, and specifically, organopolysiloxane-polyoxyalkylene copolymer, polyoxyalkylene side chain polyalkenyl siloquine having the following. Regarding the manufacturing method, chemical structure, and specific compound examples of these organosilicon surfactants, see, for example, Japanese Patent Publication No. 35-10543, Japanese Patent Publication No. 36-13344, and Japanese Patent Publication No. 37-1989.
8850, Tokuko Shou 38-6000, Tokuko Sho 39-1850, Tokuko Sho
40-12190, Special Publication Showa 42-2719, Special Publication Showa 43-16399,
It is described in Special Publication No. 43-17998, etc. The amount of organosilicon surfactant added according to the invention is considerably higher than the amounts normally used in the production of urethane or isocyanurate foams, preferably 3% by weight or more, preferably 4 to 20% by weight.
%, more preferably from the range of 5 to 10%. The isocyanate compound used in the present invention is an organic compound in which two or more NCO groups are bonded within the same molecule, and includes aliphatic and aromatic polyisocyanate monomers, mixtures thereof, etc. Contains modified products. Examples of the aliphatic polyisocyanate sheet include hexamethylene diisocyanate sheet, isophorone diisocyanate, dicyclohexylmethane diisocyanate, and the like. Examples of aromatic polyisocyanates include tolylene diisocyanate (2,4 and 2,6-
isomer), diphenylmethane diisocyanate,
Vitolylene diisocyanate, naphthylene diisocyanate (e.g. 1,5-naphthylene diisocyanate), polynuclear polyisocyanate (so-called crude,
MDI or polymeric isocyanate), etc. Further, the aromatic polyester polyol used in the present invention is usually synthesized by a condensation reaction between an aromatic polycarboxylic acid, an ester thereof, or an acid anhydride thereof, and a polyol having a primary hydroxyl group. As aromatic carboxylic acids and their derivatives,
For example, phthalic acid, trimellitic acid, pyromellitic acid, and their esters and acid anhydrides can be mentioned. Examples of the polyol having a primary hydroxyl group to be reacted with an aromatic carboxylic acid include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butanediol, trimethylolpropane, and hexanediol. The polyester polyol used in the present invention is obtained by condensing one or more of the above carboxylic acids and polyols, and the hydroxyl value of these polyester polyols is usually 200 to 600 mg.
About KOH/g is preferable. The compositional content (amount used) of this polyester polyol is 3 to 36%, preferably 5 to 20%, and if it is less than 3%, it is difficult to obtain the specified heat resistance and flame retardancy, and if it is less than 36% In the above cases, the equivalence ratio (isocyanate index) decreases and the compatibility decreases, resulting in poor heat resistance, flame retardancy, etc.
This is not very preferable because it may cause disadvantages in terms of physical properties. When producing the foam according to the present invention, a urethanization catalyst and a blowing agent are used, and these are appropriately selected from those used in the production of ordinary urethane foams. As a urethanization catalyst, triethylamine,
N, N', N'-tris (dimethylaminopropyl)
Tertiary amines such as hexahydrotriazine, 2,4,6-tris(dimethylaminomethyl)phenol, tetramethylethylenediamine, diazabicycloalkene; tertiary amines, ethyl alcohol, mono-N-substituted carbonate Examples of using co-catalysts such as acid esters; tertiary phosphines;
Examples include carboxylic acid metal salts such as potassium acetate. In addition, as a blowing agent, a low boiling point inert organic solvent that evaporates due to the heat of reaction generated during foam generation, such as trichloromonofluoromethane, dichlorofluoromethane, dichloromonofluoromethane, hexane, etc., is used, but other isocyanin Compounds that react with carbonate to generate carbon dioxide, such as water, compounds containing water of crystallization, nitroalkanoic acid amides, or compounds that generate gas by thermal decomposition due to the heat of reaction during foam formation, such as sodium bicarbonate. etc. can also be used. In the present invention, since a large amount of organosilicon-based surfactant is used as a smoke suppressant, there is no need to add various kinds of surfactants, but in some cases, it is necessary to add various kinds of surfactants to help homogenize the reaction mixture. Other types of nonionic surfactants, anionic surfactants,
It is also possible to add a cationic surfactant. In the present invention, various additives may be further added as necessary, and examples of additives include phosphorus- and halogen-containing organic compounds, halogen-containing resins,
Additive flame retardants such as antimony oxide and aluminum hydroxide, colored powders such as pigments and dyes, talc,
Examples include diatomaceous earth, inorganic powders such as graphite, short glass fibers, and other inorganic fillers. Various methods are known for producing isocyanurate ring-containing urethane foams, but these can be roughly divided into: (a) adding a trimerization catalyst, blowing agent, surfactant, etc. to organic polyisocyanate; Method of stirring and foaming. (b) A method for producing a modified isocyanurate ring-containing urethane foam, that is, a foaming method similar to the above, in which a modifier is reacted with a polynuclear polyisocyanate in advance to foam the modified polyisocyanate (prepolymer method). (c) a polyol containing an isocyanerate ring;
A foaming method using a polyisocyanate, a blowing agent, a surfactant, and a urethanization catalyst. can be mentioned. The method of the present invention can be applied to any of the methods (a), (b), and (c), but in order to achieve the purpose of the present invention, Among the methods, it is particularly advantageous to carry out the reaction using polyisocyanates modified with small amounts of modifiers. In addition, as the modifier for the modified isocyanurate ring-containing foam in the method (b) above, polyether polyols, polyester polyols, polyepoxides, polycarbon acids, oils and fats having hydroxy end groups, liquid dienes having hydroxy end groups are used. Polymers and phenolic resin initial condensates (phenols, novolacs) are known. Japanese patents regarding the manufacturing method of these various modified isocyanurate ring-containing urethane foams and trimerization catalysts are described in "Plastic Materials" Vol. 16, No. 1 (1975), p. 56. "Effects of the Invention" As detailed above, the foam obtained by the method of the present invention has excellent heat resistance and flame retardancy, and is also low smoke emitting, so it can be used in a wider range of formulations and is effective as a quasi-nonflammable material. It not only has excellent fire prevention performance (JIS A 1301) as an exterior wall material. In particular, the present invention has remarkable effects on composite building materials with iron plates, ceramic materials, aluminum, steel foil, real cement, gypsum boards, and the like. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Examples 1 to 2 and Comparative Examples 1 to 3 Polyisocyanates, aromatic polyester polyols, aliphatic polyether polyols, silicone surfactants, trimerization catalysts, flame retardants, ferrocene, and blowing agents were used to prepare polyisocyanates as shown below. An isocyanurate foam was produced. Table 1 shows the blending ratio and the physical properties of the obtained foam. The physical properties of the foam have the following meanings. Raw material polyisocyanate: PAPI-135 (Product name: Polymethylene-polyphenylene-polyisocyanate, NCO equivalent 135, manufactured by Kasei Upjiyon Co., Ltd.) Fragrance polyester polyol: Terate-202
(Product name: OH equivalent 127.5, manufactured by Hercules)
Terateâ203 (Product name: OH equivalent 178, Hercules
(Manufactured by Toray Silicone Co., Ltd.) Lipidic polyether polyol: GP-250 (Product name: Sanyo Kasei Co., Ltd.) Silicone surfactant: SH-193 (Product name: Toray Silicone Co., Ltd.) Trimerization catalyst: Crithane-51 (Product name: Flame retardant: Ferrocene (reagent) Foaming agent: R-11E (trichloromonofluoromethane) "Foam properties" Smoke-emitting property: Expressed by JIS A1321 smoke-emitting coefficient CA. Heat resistance: Qualitatively judge items harmful to fire prevention such as deformation and cracks according to JIS A1321. It is expressed as the temperature at which 30% weight loss occurs using a thermobalance. Flame retardancy: Based on JIS K7201's oxygen index method for flame testing of polymer materials. To produce the foam, a mixture of PAPI-135 and other components such as polyol and a blowing agent was thoroughly mixed and the two liquids were combined at the time of foaming and rapidly stirred to cause foaming.
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ãããããªãŒã ç©æ§ã«ã€ããŠè¡šâïŒã«ç€ºããã[Table] Examples 3 to 7 Foams were produced by varying the amounts of silicone surfactant and iron compound added. Table 2 shows the mixing ratio of raw materials and the physical properties of the obtained foam.
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ããªããããã·ååç©ãšããŠèèæããªãšã¹ã
ã«ããªãªãŒã«ïŒIsonolâ11ïŒåååãã¢ãããžãš
ã³(æ ª)補ïŒãOHåœé234ïŒãçšããéååç©ãå ã
ãªãã€ã以å€ã¯å®æœäŸïŒãïŒãšåæ§ã«ããŠããªãŒ
ã ã補é ãããåæé
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ãŒã ç©æ§ã«ã€ããŠè¡šãŒïŒã«ç€ºãã
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ã«ããªãªãŒã«ïŒBPXâ11ïŒåååãæé»åå·¥æ¥(æ ª)
補ïŒãOHåœé310ïŒãçšããã·ãªã³ãŒã³çé¢æŽ»æ§
å€åã³éååç©ã®æ·»å éãå€ãã以å€ã¯å®æœäŸïŒ
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ã«ç€ºãã[Table] Comparative Example 4 Examples 1 to 2 except that aliphatic polyester polyol (Isonol-11 (trade name, manufactured by Upjiyon Co., Ltd.), OH equivalent 234) was used as the polyhydroxy compound, and no iron compound was added. A foam was manufactured in the same manner as above. Table 3 shows the blending ratio of raw materials and the physical properties of the obtained foam. Comparative Examples 5 to 7 Aromatic polyether polyol (BPX-11 (trade name, Asahi Denka Kogyo Co., Ltd.) was used as the polyhydroxy compound.
Example 1 except that the silicone surfactant and the amount of iron compound added were changed.
A foam was produced in the same manner as in 2. Table 3 for raw material blending ratio and obtained foam physical properties
Shown below.
ãè¡šããtableã
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ã³åŸãããããªãŒã ç©æ§ã«ã€ããŠè¡šâïŒã«ç€ºãã[Table] Comparative Examples 8 to 9 Foams were produced in the same manner as in Example 1, except that the amount of polyhydroxy compound or organosilicon surfactant added was changed. Table 4 shows the blending ratio of raw materials and the physical properties of the obtained foam.
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[Table] Use
Claims (1)
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ã«å¯æº¶ãªéååç©ãéå çŽ ã«æç®ããŠ0.05ã10é
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ç³»çé¢æŽ»æ§å€ã®å²åã20ïŒïŒãïŒïŒïŒã§ããããš
ãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®ããªãŠ
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ã·ååç©ã®NCOïŒOHïŒåœéæ¯ïŒã1.5以äžã§ãã
ããšãç¹åŸŽãšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé åã¯ç¬¬ïŒ
é èšèŒã®ããªãŠã¬ã¿ã³ããªãŒã ã®è£œé æ¹æ³ã[Scope of Claims] 1. When producing polyurethane foam using polyisocyanates and polyhydroxy compounds as main raw materials, the polyhydroxy compounds include a group consisting of aromatic polyhydric carboxylic acids, carboxylic acid anhydrides, and carboxylic acid esters. 3% by weight or more of an aromatic polyester polyol derived from at least one aromatic compound selected from the following, and an organopolysiloxane-polyoxyalkylene copolymer or a polyalkenylsiloxane having a polyoxyalkylene side chain. Flame retardant, heat resistant and A method for producing polyurethane foam with excellent low smoke emission. 2. The method for producing a polyurethane foam according to claim 1, wherein the ratio of the aromatic polyester polyol to the organosilicon surfactant is 20/1 to 1/7. 3. Claim 1 or 2, characterized in that the NCO/OH (equivalent ratio) of polyisocyanate and polyhydroxy compound in the raw materials is 1.5 or more.
2. Method for producing polyurethane foam as described in Section 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59114333A JPS60258220A (en) | 1984-06-04 | 1984-06-04 | Production of flame retardant, heat resistant and low smoking polyurethane foam |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59114333A JPS60258220A (en) | 1984-06-04 | 1984-06-04 | Production of flame retardant, heat resistant and low smoking polyurethane foam |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60258220A JPS60258220A (en) | 1985-12-20 |
JPH0126606B2 true JPH0126606B2 (en) | 1989-05-24 |
Family
ID=14635174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59114333A Granted JPS60258220A (en) | 1984-06-04 | 1984-06-04 | Production of flame retardant, heat resistant and low smoking polyurethane foam |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60258220A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8801525D0 (en) * | 1988-01-23 | 1988-02-24 | Ciba Geigy Ag | Smoke & toxic gas suppressant composition |
JP5873653B2 (en) * | 2011-05-31 | 2016-03-01 | äžæŽåæå·¥æ¥æ ªåŒäŒç€Ÿ | Strength improver for polyurethane foam production |
CN109836556A (en) * | 2019-01-31 | 2019-06-04 | åå·å€§åŠ | A kind of low VOC polyurethane foam material and preparation method containing molysite |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5372098A (en) * | 1976-12-08 | 1978-06-27 | Mitsubishi Chem Ind Ltd | Manufacture of flame-retardant foam |
-
1984
- 1984-06-04 JP JP59114333A patent/JPS60258220A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5372098A (en) * | 1976-12-08 | 1978-06-27 | Mitsubishi Chem Ind Ltd | Manufacture of flame-retardant foam |
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JPS60258220A (en) | 1985-12-20 |
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