JPS6332085B2 - - Google Patents
Info
- Publication number
- JPS6332085B2 JPS6332085B2 JP57036361A JP3636182A JPS6332085B2 JP S6332085 B2 JPS6332085 B2 JP S6332085B2 JP 57036361 A JP57036361 A JP 57036361A JP 3636182 A JP3636182 A JP 3636182A JP S6332085 B2 JPS6332085 B2 JP S6332085B2
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- polyisocyanate
- weight
- foam
- polyurethane 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
- 229920005862 polyol Polymers 0.000 claims description 51
- 150000003077 polyols Chemical class 0.000 claims description 50
- 239000006260 foam Substances 0.000 claims description 26
- 239000005056 polyisocyanate Substances 0.000 claims description 26
- 229920001228 polyisocyanate Polymers 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 20
- 239000011496 polyurethane foam Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 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 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011342 resin composition Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 19
- 238000000465 moulding Methods 0.000 description 16
- -1 ester compound Chemical class 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 150000002513 isocyanates Chemical class 0.000 description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
- 239000011550 stock solution Substances 0.000 description 8
- 239000004604 Blowing Agent Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 238000005452 bending Methods 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
- 229940029284 trichlorofluoromethane Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000010107 reaction injection moulding Methods 0.000 description 3
- 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 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Description
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J.SaundersïŒK.C.FrishèãPolyurethanes
Chemisty and TechnologyïŒPart 
ChemistryïŒPart TechnologyãRobert E.
Krieger Publishing CompanyïŒHuntingtonïŒ
New York1978ïŒDavid StalyèãAnalytical
Chemistry of the PolyurethanesïŒ
PolyurethanesïŒPartãRobert ïŒKriger
Publishing CompanyïŒHuntingtonïŒNew
York1979ã岩ç°æ¬æ²»èããã©ã¹ããã¯æææ§åº§
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The present invention relates to a resin composition for producing a skinned rigid polyurethane foam. Polyurethane foam with a skin, which is obtained by mixing isocyanate, polyether containing active hydrogen, a blowing agent, a catalyst, etc., and then foaming and curing in a closed mold, is used in electrical and electronic equipment because of its excellent heat insulation, sound absorption, and strength. Suitable for use as parts materials and building materials. In recent years, with the development of reaction injection molding technology (RIM technology), the uses of the above-mentioned foam bodies are increasingly expanding. However, one factor limiting the industrial use of this aerated urethane product is the long molding cycle, especially the demolding time (from injecting the composition into the mold to ejecting the molded part). time) is long. That is, when the molded product is removed from the mold in a short period of time, the foam swells due to the foaming pressure, so the molded product must be held in the mold for a long time. Conventionally known methods for shortening demolding time include:
There are methods such as increasing the amount of catalyst blended, blending a highly active catalyst, and increasing the liquid temperature, but in these cases, the fluidity of the foam decreases and the surface properties of the foam deteriorate. There were flaws. Furthermore, it is known that by converting polyisocyanate into a prepolymer, heat generation during molding can be suppressed and demolding time can be shortened. However, this method has disadvantages in that the storage stability of the polyisocyanate decreases, the viscosity increases, and the heat resistance of the obtained foam decreases. The object of the present invention is to avoid the drawbacks of the above-mentioned prior art.
The resin composition for manufacturing hard polyurethane foam with a skin that can be demolded in a short time is characterized by the use of a polyol polymerized with polyisocyanate, which lowers the maximum exothermic temperature during molding and reduces the temperature during demolding. suppresses molded product blistering phenomenon,
The aim is to shorten demolding time. Specifically, the above resin composition is a prepolymerized polyol with an OH value of 350 to 800 KOH mg/g (this polyol is hereinafter referred to as polyol (A)), and a polyisocyanate (hereinafter referred to as polyisocyanate). , polyisocyanate (B)
) at an NCO/OH molar ratio of 0.05 to 0.3; a reaction accelerator for polyurethane production; a blowing agent; a foam stabilizer; and a polyisocyanate (hereinafter referred to as polyisocyanate). isocyanate (C)) as an essential component. This resin composition has good storage stability, and by using it, a rigid polyurethane foam with a skin that has excellent mechanical and thermal properties can be molded in a shorter time than ever before. It is something. Hereinafter, the resin composition of the present invention will be explained in more detail, and the process for producing the foam will be explained. Polyols (A) used in the present invention include polyether polyols and polyester polyols. Specific examples of these include glycerin, trimethylolpropane, ammonia, monoethanolamine, triethanolamine, pentaerythritol, sorbitol, sucrose, phenol,
Tolylene diamine, 4,4'-diaminodiphenylmethane, xylylene diamine, hydrogenated 4,4'-
There is a polyether polyol obtained by adding an alkylene oxide to diaminodiphenylmethane or the like. There is also a polyester polyol obtained by adding an alkylene oxide to an ester compound (carboxyl terminal) obtained by reacting phthalic anhydride with propylene glycol or ethylene glycol. Polyols other than those listed above include
âPolyurethanesâ by J.Saunders, K.C.Frish
Chemistry and Technology, Part I
Chemistry, Part Technologyâ Robert E.
Krieger Publishing Company, Huntington,
New York 1978, âAnalyticalâ by David Staly
Chemistry of the Polyurethanes,
Polyurethanes: Partâ Robert E, Kriger
Publishing Company, Huntington, New
York1979, Keiji Iwata, âPlastic Material Structureâ
There is a polyol described in "(2) Polyurethane Resin" Nikkan Kogyo Shinkaisha 1975. Particularly important among these are polyols obtained by adding alkylene oxide to aromatic amines represented by the following general formula (1). (However, R, R': H or an alkyl group, n: a natural number) Specific examples of the aromatic amine polyols include alkylene oxide adducts of 4,4'-diaminodiphenylmethane and alkylene oxide adducts of tolylene diamine. Considering the viscosity of the polyol, the heat resistance of the resulting molded product, and the balance of mechanical properties, the proportion of the aromatic amine polyol in the polyol (A) is preferably 20 to 80% by weight. desirable. Here, polyol (A)
The OH value needs to be 350 to 800 KOHmg/g. The reason is that the OH value is 350KOH.
If it is less than mg/g, the mechanical properties of the obtained molded product will be poor, and the foam will swell due to heat generated during molding, making it difficult to shorten the demolding time as intended by the present invention. This is because it disappears. On the other hand, OH
If the OH value is greater than 800 KOHmg/g, the obtained molded product will become brittle and an industrially effective product will not be obtained, so the OH value must be 800KOHmg/g or less. The polyol (A) may be a single polyol or a mixture of various polyols. In the case of a mixture, it is sufficient that its average OH value satisfies the above conditions. As a specific example of the polyisocyanate (B) used in the present invention, MDI (4,
4'-diphenylmethane diisocyanate), but not only MDI alone, but also similar isocyanates, such as polyphenylene polymethylene polyisocyanate, carbociimidized MDI
can also be used. Furthermore, the same applies to xylene diisocyanate, isophorone diisocyanate, and tolylene diisocyanate (TDI), including the compounds described in the aforementioned literature. Among these, the particularly important polyisocyanate (B) is a TDI compound represented by the following general formula (2), and an MDI compound represented by the following general formula (3). (However, l: 0.2 to 0.8) The prepolymerized polyol in the present invention comprises the above polyol (A) and polyisocyanate (B).
It can be obtained by reacting at an NCO/OH molar ratio of 0.05 to 0.3. Specifically, polyol (A) is heated to 25 to 80°C, polyisocyanate (B) is added dropwise with good stirring, and after the dropwise addition is completed, the reaction is completed by further stirring for 1 to 6 hours. Obtainable. In this case, polyol (A)
Even if it contains water, there is no problem as long as the amount is 1.5% by weight or less. Furthermore, if necessary, various reaction accelerators may be added for the purpose of accelerating the prepolymerization reaction. The end point of the reaction is the point at which the isocyanate content in the polyol becomes zero, and this can be measured by applying commonly used analytical methods. Specific examples of the reaction accelerator, foaming agent, and foam stabilizer used in the present invention will be described below. First, examples of reaction accelerators include various tertiary amine compounds and tin compounds. Specific examples of tertiary amine compounds include triethylenediamine, dimethylethanolamine, morpholines, piperazines, imidazole compounds, DBU (1,8-diaza-bicyclo(5,4,0)undecene-7),
alkylaminosilane, etc., and their salts, such as acetate, formate, oxalate, phosphate, 2-ethylhexanoate, phenol salt,
Cresol salts, hydrochlorides, etc. can also be used. On the other hand, tin compounds include dibutyltin dilaurate,
Dibutyltin diacetate. Other reaction accelerators that can be used in the present invention include compounds described in the above-mentioned books. In addition to water, blowing agents include low-boiling organic liquid compounds such as trichlorofluoromethane and methylene chloride, and compounds that decompose to generate nitrogen gas such as azobisisobutyronitrile. By changing this amount, foams with different densities can be obtained. Among these, halogenated hydrocarbons having a particularly low boiling point (0 to 60°C) are particularly valuable compounds in the present invention because they have the property of easily forming a tough skin. Foam stabilizers include oxyalkylene copolymers of polydimethylsiloxane in general and fluorine-based surfactants in general. The polyisocyanate (C) used in the present invention is preferably a diisocyanate or a triisocyanate, but may also contain polyfunctional isocyanates higher than these. Specific examples include hexamethylene diisocyanate, m-xylene diisocyanate, m-phenylene diisocyanate, tolylene diisocyanate, MDI,
Examples include polyphenylpolymethylene polyisocyanate. Among these, particularly effective polyisocyanates
(C) is an MDI polyisocyanate represented by the following general formula (3). (However, l: 0.2 to 0.8) This is because the obtained foam has good reactivity and heat resistance, and is also inexpensive. In addition, the blending amount of polyisocyanate (C) is
The amount is preferably such that the NCO/OH molar ratio is from 0.9 to 1.2. Other materials that can be used in the present invention include fillers, pigments, dyes, flame retardants, ultraviolet absorbers, etc., and these also include the contents described in the above-mentioned book. Next, a method for obtaining a hard polyurethane foam with a skin using the composition of the present invention will be explained. The above foam is prepared by mixing the composition of the present invention and injecting it into a sealed mold kept at a temperature of 40 to 80°C.
It can be manufactured by foaming and curing. However, in the composition of the present invention, after mixing the prepolymerized polyol and the polyisocyanate (C),
Since the time until gelation is extremely short, when molding the foam, an R liquid containing a reaction accelerator, a blowing agent, a foam stabilizer, and other auxiliary materials as necessary is mixed into the prepolymerized polyol. It is necessary to prepare a P liquid made of polyisocyanate (C) in advance, and mix both liquids using a high-pressure collision mixing type foaming machine. Therefore, since the conventional mixing method (mixing method using a low-pressure foaming machine) requires a long time for mixing and has low mixing efficiency, it is not possible to obtain a good skinned foam using the composition of the present invention. I can't. The composition of the present invention is particularly effective when producing a hard skinned polyurethane foam, and from the experience of producing conventional uniform foam bodies, semi-rigid foam bodies, and soft foam bodies, the present invention It is not possible to guess what is intended. Hereinafter, a method for manufacturing a hard polyurethane foam with a skin using the resin composition of the present invention will be specifically explained with reference to the drawings. The figure is a schematic explanatory diagram of a liquid reaction injection molding apparatus for producing a skinned rigid polyurethane foam using the composition of the present invention. In this device, when the stock solution is not discharged, the stock solution A containing prepolymerized polyol, a blowing agent, and a catalyst as the main components, and the stock solution B containing polyisocyanate as the main components stored in the stock solution tanks 1 and 3 are pumped through a high-pressure metering pump 6, 6 to the mixing head 8, it returns to the stock solution tanks 1 and 3 via the heat exchangers 5 and 5 connected to the temperature controller 11. On the other hand, when discharging the stock solution, the hydraulic unit 7 The mixing head 8 is operated, and the collided mixed stock solution is transferred to the cavity 2 of the closed type 10 placed between the clamping units 9.
It is designed to be ejected within 0. When the resin composition of the present invention is used in such an apparatus, a hard polyurethane foam with a skin having a density of 0.1 to 0.6 g/cm 3 and a thickness of 3 to 30 mm can be produced in a short time. The obtained foam is particularly effective for manufacturing various electrical equipment parts, automobile parts, and audio equipment parts that require heat insulation, sound absorption, weight reduction, and the like. The present invention will be explained in more detail below with reference to Examples. The contents described below are examples based on the equipment, molding conditions, and measuring methods shown in Table 1, unless otherwise specified. Further, the unit of the numerical value showing the blending ratio of the foam composition and the prepolymerized polyol is parts by weight. First, an example of manufacturing a prepolymerized polyol used in a foam manufacturing example will be described, and then an example of foam manufacturing will be described. Production example of prepolymerized polyol Production of prepolymerized polyol a The polyol shown in column (a) of Table 2, that is,
PO (propylene oxide) adduct of 4,4'-diaminodiphenylmethane (OH value: 450
ãè¡šããtableã
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ãè¡šã
KOHmgïŒïœïŒ40éééšã«ãã°ãªã»ãªã³ã®POä»å
ç©ïŒOH䟡ïŒ600KOHmgïŒïœïŒ60éééšãæ··å
ããæ··å液ïŒå¹³åOH䟡ïŒ540KOHmgïŒïœïŒã60
âã«ä¿æããŠãããã«MDIç³»ã€ãœã·ã¢ããŒã
ïŒïœïŒ0.6ïŒNCOå«æçïŒ30.5ééããŒã»ã³ãïŒ
ããè¯ãæ¹æããªãã13éééšå ããŠããã®ç¶æ
ã§ïŒæéæ¹æããŠããã¬ããªãåããªãªãŒã«ïœã
補é ãããNCOïŒOHã¢ã«åã¯0.1ã§ããã
Siggiaãã®æ¹æ³ïŒåèæç®ïŒA.FarkasïŒJ.Am.
Chem.Soc.82ïŒ642ïŒ1960ïŒïŒã«ãããã¬ããªãå
ããªãªãŒã«ïœäžã®ã€ãœã·ã¢ããŒããåæãããã
æ®åããã€ãœã·ã¢ããŒãã¯æ€åºãããªãã€ãã
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åã¢ã«æ¯ã¯ããããã0.06ã0.15ã
0.20ã0.15ã0.28ã§ããããããã®ãã¬ããªãå
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ãã[Table] Mix 60 parts by weight of glycerin PO adduct (OH value: 600KOHmg/g) with 40 parts by weight (KOHmg/g), and mix 60 parts by weight of the mixed solution (average OH value: 540KOHmg/g).
â and added MDI isocyanate (l=0.6; NCO content: 30.5% by weight)
13 parts by weight of was added to the mixture while stirring well, and the mixture was stirred for 3 hours to produce prepolymerized polyol a. NCO/OH moleization is 0.1.
The method of Siggia et al. (References: A. Farkas, J. Am.
Chem.Soc.82, 642 (1960)) was used to analyze isocyanates in prepolymerized polyol a.
No residual isocyanate was detected. Production of prepolymerized polyols b 1 , b 2 , b 3 , C, and d As shown in columns (b), (c), (d), (e), and (f) of Table 2, each polyol In the same manner as for prepolymerized polyol a, polyisocyanate is added to prepolymerized polyols b 1 , b 2 ,
b 3 , c, and d were produced. b 1 , b 2 , b 3 , c, d
The NCO/OH blending molar ratio is 0.06, 0.15, and
They are 0.20, 0.15, and 0.28. There was no residual isocyanate in these prepolymerized polyols. Production of prepolymerized polyol e 100 parts by weight of the mixed polyol shown in column (a) of Table 2 was maintained at 60°C, and 8.4 parts by weight of TDI isocyanate (NCO content: 48% by weight) was added thereto. , and stirred for 6 hours to produce prepolymerized polyol e. The NCO/OH blending molar ratio is 0.1. Isocyanate in prepolymerized polyol e was analyzed by the method of Siggia et al., but no residual isocyanate was detected. Foam Manufacturing Examples Example 1 Using the composition shown in the Example 1 column of Table 3,
With the equipment and molding conditions shown in Table 1, the density is 0.35g/
A rigid polyurethane foam with a skin of cm 3 was produced.
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ã¯ããããã180KgïŒcm2ã8.0Kgã»cmïŒcm2 [Table] That is, 113 parts by weight of prepolymerized polyol a and 10 parts by weight of trichlorofluoromethane as a blowing agent.
parts by weight, 0.5 parts by weight of H 2 O, 2.0 parts by weight of alkylene oxide modified polydimethylsiloxane as a foam stabilizer, 3.0 parts by weight of triethylenediamine as a reaction accelerator.
Parts by weight, DBU [1,8-diazabicyclo(5,
4,0) Undecene-7] Add 0.1 part by weight,
The R solution was prepared by stirring well at room temperature. The above R liquid and P liquid consisting of 4,4'-diphenylmethane diisocyanate (NCO content: 31% by weight; l = 0.6) are mixed, foamed, and hardened under the equipment and molding conditions shown in Table 1 to obtain a density. A flat plate with a weight of 0.35 g/cm 3 and a thickness of 2 cm was molded. Blending ratio (weight ratio) of R liquid and P liquid
was performed with R:P=100:114. The maximum exothermic temperature during molding, demolding time, and mechanical properties were as shown in the column of Example 1 in Table 4. In other words, the maximum exothermic temperature is as low as 145â.
The demolding time was as short as 120 seconds. Also, bending strength and Izotsu impact value (without notch)
are 180Kg/cm 2 and 8.0Kgã»cm/cm 2 respectively.
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äžã§ããå¹æãå¥ããã[Table] Both showed high values. Examples 2, 3, 4, 5, 6, 7, 8 A hard polyurethane foam with a skin was produced in the same manner as in Example 1 using the compositions shown in the columns of Examples 2 to 8 in Table 3. Molded. The density, maximum heat generation temperature during molding, demolding time, bending strength, and Izot impact value of the obtained molded product are as follows:
They were as shown in columns 2 to 8 of Table 4. That is, no matter which composition is used,
The maximum exothermic temperature during molding was low and demolding time was short. Furthermore, both bending strength and Izot impact value showed good values. Example 9 100 parts by weight of prepolymerized polyol e, 10 parts by weight of trichloromonofluoromethane, 0.5 parts by weight of H 2 O,
Alkylene oxide modified polydimethylsiloxane
2.0 parts by weight of triethylenediamine, 1.0 parts by weight of triethylenediamine, 0.1 parts by weight of dibutyltin dilaurate, and 1.0 parts by weight of carbon black were added and mixed well to prepare R liquid. A hard polyurethane foam with a skin was molded using the R liquid and the P liquid shown in Table 3 at a blending ratio (weight ratio) of 100:116 using the equipment and molding conditions shown in Table 2. The density of the obtained molded article was 0.35 g/cm 3 and the maximum exothermic temperature during molding was 149°C. The demolding time is as short as 125 seconds, and the bending strength and Izotsu impact value of the molded product are 175Kg/cm 2 and 7.5Kgã»cm/, respectively.
cm 2 , a good value. Comparative Example A hard polyurethane foam with a skin was molded under the same conditions as in Example 1. However, the polyol used was one that had not been prepolymerized. As a result, the maximum exothermic temperature during molding was higher than in Example 1, and the demolding time was longer than in Example 1. The contents will be explained in detail below. A polyol consisting of 40 parts by weight of PO adduct of 4,4'-diaminodiphenylmethane and 60 parts by weight of glycerin PO adduct, 10 parts by weight of trichlorofluoromethane as a blowing agent, 0.5 part by weight of H 2 O, and a foam stabilizer. 2.0 parts by weight of alkylene oxide-modified polydimethylsiloxane, 3.0 parts by weight of triethylenediamine as a reaction accelerator, and 0.1 part by weight of DBU/phenol salt were added to prepare an R liquid. Using this R liquid and P liquid consisting of 4,4'-diphenylmethane diisocyanate (MDI) system (NCO content: 31% by weight; l = 0.6), the density A rigid polyurethane foam with a skin of 0.35 g/cm 3 was molded. The blending ratio (weight ratio) of R liquid and P liquid was 100:126. In this case, the maximum exothermic temperature during molding was as high as 160°C, and the demolding time was as long as 200 seconds. The bending strength and Izod impact value of the molded product are respectively
168 Kg/cm 2 and 7.2 Kg·cm/cm 2 , both of which were lower than those of Example 1. As specifically stated above in the Examples and Comparative Examples,
By using the composition of the present invention, a hard skinned polyurethane foam with excellent mechanical properties can be molded in a short time. Therefore, the molding cycle can be significantly shortened compared to the conventional method, and production efficiency can be dramatically improved.
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The figure is a schematic illustration of a liquid reaction injection molding apparatus for producing a skinned rigid polyurethane foam using the composition of the present invention. 1, 3... Stock solution tank, 8... Mixing head, 11... Temperature controller, 10... Closed type.
Claims (1)
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480ïŒã®ããªãªãŒã«ãããªãããªãªãŒã«(A)ãšãã
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0.3ã®å²åã§åå¿ãããŠåŸããããã®ïŒ ããªãŠã¬ã¿ã³çæçšåå¿ä¿é²å€ïŒ çºæ³¡å€ïŒ æŽæ³¡å€ïŒããã³ ããªã€ãœã·ã¢ããŒã(C)ïŒ ãå¿ é æåãšããããšãç¹åŸŽãšããè¡šç®ä»ã硬質
ããªãŠã¬ã¿ã³ããªãŒã 補é çšæš¹èçµæç©ã ïŒ åèšã®ããªãªãŒã«(A)ã®20ã80ééããŒã»ã³ã
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ããªãŠã¬ã¿ã³ããªãŒã 補é çšæš¹èçµæç©ã[Claims] 1. As a prepolymerized polyol, an OH value of 350
~800KOHmg/g (210~ in terms of average molecular weight)
Polyol (A) consisting of polyol (480) and polyisocyanate (B) at an NCO/OH molar ratio of 0.05 to
A resin for producing a rigid polyurethane foam with a skin, characterized in that the essential components are: a product obtained by reacting at a ratio of 0.3; a reaction accelerator for polyurethane production; a foaming agent; a foam stabilizer; and polyisocyanate (C). Composition. 2. The skin according to claim 1, wherein 20 to 80 weight percent of the polyol (A) is a polyol obtained by adding alkylene oxide to an aromatic amine represented by the following general formula (1). Resin composition for manufacturing hard polyurethane foam. However, R, R': H or alkyl group n: natural number 3 The polyisocyanate (B) is a 4,4'-diphenylmethane diisocyanate (MDI) compound represented by the following general formula (3), (However, l: 0.2 to 0.8) The resin composition for producing a hard polyurethane foam with a skin according to claim 1. 4 The above polyisocyanate (C) is a 4,4'-diphenylmethane diisocyanate (MDI) compound represented by the following general formula (3), (However, l: 0.2 to 0.8) The resin composition for producing a hard polyurethane foam with a skin according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57036361A JPS58154714A (en) | 1982-03-10 | 1982-03-10 | Resin composition for producing skinned rigid polyurethane foam |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57036361A JPS58154714A (en) | 1982-03-10 | 1982-03-10 | Resin composition for producing skinned rigid polyurethane foam |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58154714A JPS58154714A (en) | 1983-09-14 |
JPS6332085B2 true JPS6332085B2 (en) | 1988-06-28 |
Family
ID=12467687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57036361A Granted JPS58154714A (en) | 1982-03-10 | 1982-03-10 | Resin composition for producing skinned rigid polyurethane foam |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58154714A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60196442A (en) * | 1984-03-15 | 1985-10-04 | Toyoda Gosei Co Ltd | Impact absorbing material |
DE4200157A1 (en) * | 1992-01-07 | 1993-07-08 | Bayer Ag | LIQUID, LIGHT, POLYISOCYANATE MIXTURES, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN THE PRODUCTION OF LIGHT, HARD POLYURETHANE FOAMS |
US6218443B1 (en) | 1997-12-30 | 2001-04-17 | Basf Corporation | Pentafluoropropane blowing agent-containing resin blend for use in making integral skin foams |
US6010649A (en) * | 1997-12-30 | 2000-01-04 | Basf Corporation | Method of making a low density, molded integral skin polyurethane foam |
-
1982
- 1982-03-10 JP JP57036361A patent/JPS58154714A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS58154714A (en) | 1983-09-14 |
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