JPH01299814A - Preparation of polyurethane foam - Google Patents
Preparation of polyurethane foamInfo
- Publication number
- JPH01299814A JPH01299814A JP63127146A JP12714688A JPH01299814A JP H01299814 A JPH01299814 A JP H01299814A JP 63127146 A JP63127146 A JP 63127146A JP 12714688 A JP12714688 A JP 12714688A JP H01299814 A JPH01299814 A JP H01299814A
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- polyurethane foam
- hydrocarbon resin
- weight
- aromatic hydrocarbon
- 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.)
- Pending
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 42
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 42
- 229920005862 polyol Polymers 0.000 claims abstract description 66
- 150000003077 polyols Chemical class 0.000 claims abstract description 64
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 15
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 15
- 239000010419 fine particle Substances 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 abstract description 36
- 238000000034 method Methods 0.000 abstract description 17
- 239000006185 dispersion Substances 0.000 abstract description 11
- 239000002245 particle Substances 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 238000005187 foaming Methods 0.000 abstract description 8
- 239000004014 plasticizer Substances 0.000 abstract description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 6
- 239000000945 filler Substances 0.000 abstract description 6
- 239000010734 process oil Substances 0.000 abstract description 6
- 238000010186 staining Methods 0.000 abstract description 6
- 239000003431 cross linking reagent Substances 0.000 abstract description 5
- 238000000465 moulding Methods 0.000 abstract description 5
- 239000004088 foaming agent Substances 0.000 abstract description 3
- 239000000084 colloidal system Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 239000010426 asphalt Substances 0.000 description 20
- 229920002635 polyurethane Polymers 0.000 description 15
- 239000004814 polyurethane Substances 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- -1 diene polyols Chemical class 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- 239000004604 Blowing Agent Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 125000005474 octanoate group Chemical group 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002904 solvent Substances 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
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 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
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-BGYRXZFFSA-N 1-o-[(2r)-2-ethylhexyl] 2-o-[(2s)-2-ethylhexyl] benzene-1,2-dicarboxylate Chemical compound CCCC[C@H](CC)COC(=O)C1=CC=CC=C1C(=O)OC[C@H](CC)CCCC BJQHLKABXJIVAM-BGYRXZFFSA-N 0.000 description 1
- RVGLUKRYMXEQAH-UHFFFAOYSA-N 3,3-dimethyloxetane Chemical compound CC1(C)COC1 RVGLUKRYMXEQAH-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000555081 Stanus Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002334 glycols 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
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、軟質、半硬質、硬質などのポリウレタンフォ
ームの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for manufacturing flexible, semi-rigid, rigid, etc. polyurethane foams.
ポリウレタンフォームのポリウレタンに歴青を含有させ
ることは知られている。ポリウレタンに歴青を含有させ
ることにより、耐水性、耐久性の増大、低周波の振動、
音波等の吸収効果があり、またコスト低減にも役立って
いる。歴青としては、タール、アスファルト等が用いら
れている。It is known to include bitumen in the polyurethane of polyurethane foams. By adding bitumen to polyurethane, it increases water resistance, durability, low frequency vibration,
It has the effect of absorbing sound waves, etc., and also helps reduce costs. As bitumen, tar, asphalt, etc. are used.
タールポリウレタンは、歴青としてタールを用いるもの
で、タールがポリウレタン原料のポリオール、ポリイソ
シアネ−１・との相溶性がよ〈従来から実用されている
が、タール臭が残ることと、タールに発がん性物質を含
んでいるということか”ら、タールに代ってアスファル
トの使用が検討されている。しかし、アスファルトは、
タールのように一般のポリウレタン原料との相溶性がよ
くないので、実用上いろいろと問題があった。そのため
、ポリウレタン原料にアスファルトを混合して発泡する
方法をとらないで、ポリウレタンフォームに対し、アス
ファルトを揮発性溶剤に溶解したアスファルト溶液か、
アスファルトを水中に乳化したアスファルト乳剤を古漬
させ乾燥していた。Tar polyurethane uses tar as bituminous material, and tar is highly compatible with the polyol and polyisocyanate-1, which are the raw materials for polyurethane. The use of asphalt in place of tar is being considered because it contains certain substances.However, asphalt
Since it has poor compatibility with common polyurethane raw materials such as tar, there have been various practical problems. Therefore, instead of using a method of mixing asphalt with polyurethane raw materials and foaming them, we use an asphalt solution in which asphalt is dissolved in a volatile solvent for polyurethane foam.
Asphalt emulsion, which is made by emulsifying asphalt in water, was aged and dried.
しかしながら、溶剤は、作業中に引火する危険性と公害
の問題があり、乳剤は、乾燥に時間を要する欠点を持っ
ている。また、製品の取扱いに際し、ベタついたりする
問題があった。However, solvents have the risk of catching fire during operation and pose pollution problems, and emulsions have the disadvantage of requiring a long time to dry. In addition, there was a problem that the product became sticky when handled.
一方、特公昭６０−２８２９８号公報には、歴青質発泡
体の製造方法の新しい方法が提案されている。この方法
は、ポリオール、ポリイソシアネート、発泡剤、充填剤
、触媒及びその他の助刑の（アスファル！−）をポリオ
ール１００重量部に対し１５０〜２００重量部配合し、
（ｂ）発泡剤として分解温度が７５゛〜３００℃の無機
古木（ヒ物を使用し、（ｃ）諸原料を９０〜２５０℃の
高温で混合発泡させてポリウレタンフォームを遣るもの
である。しかし、この方法は、ポリオールにアスファル
トと相溶性のよい材料、例えばジエン系ポリオール（ポ
リブタジェンポリオール）、ヒマシ油系ポリオール、ダ
イマー酸系ポリオールなどの特定のポリオールを主に用
いている。また、混合発泡温度が９０〜２５０℃という
高い温度を必要とし、かつ、特定の発泡剤を用いている
など問題点がある。On the other hand, Japanese Patent Publication No. 60-28298 proposes a new method for producing bituminous foam. In this method, 150 to 200 parts by weight of polyol, polyisocyanate, blowing agent, filler, catalyst, and other additives (asphalt!-) are blended to 100 parts by weight of polyol.
(b) Uses inorganic old wood with a decomposition temperature of 75°C to 300°C as a foaming agent, and (c) Mixes and foams various raw materials at a high temperature of 90°C to 250°C to produce polyurethane foam. However, This method mainly uses materials that are highly compatible with asphalt as the polyol, such as specific polyols such as diene polyols (polybutadiene polyols), castor oil polyols, and dimer acid polyols. There are problems in that a high foaming temperature of 90 to 250° C. is required and a specific foaming agent is used.
特に、ポリウレタンフォームでは、常温で発泡でき、ま
た注入成形発泡できるものが要望されており、叙上の方
法は、このようなものにむかなかった。In particular, there is a demand for polyurethane foams that can be foamed at room temperature and that can be foamed by injection molding, and the methods described above are not suitable for such foams.
更にまた、ポリウレタンフォームの原料であるポリオー
ル中に、アスファルトを界面活性剤を用いて乳化分散さ
せておき、これとポリイソシアネート化合物と反応させ
て歴青入りポリウレタンフォームを遣る方法も提案され
ている。しかしながら、界面活性剤の使用量が多く、そ
れでいてアスファルトのポリオール中での乳化分散がわ
るく、貯蔵安定性が良好でない、また、界面活性剤の使
用量が多いためにポリウレタンフォームの耐水性、耐久
性が低下するなどの問題点があった。Furthermore, a method has also been proposed in which asphalt is emulsified and dispersed in polyol, which is a raw material for polyurethane foam, using a surfactant, and this is reacted with a polyisocyanate compound to produce bitumen-containing polyurethane foam. However, the amount of surfactant used is large, and the emulsification and dispersion of asphalt in polyol is poor, resulting in poor storage stability. There were problems such as a decrease in
本発明者らは、アスファルト、その他の歴青材をポリオ
ール中に分散させることについて研究した結果、芳香族
系炭化水素樹脂がポリオール中に界面活性剤、分散剤等
を全く使用しないで、あるいは使用するとしても非常に
僅かな量の使用で良好に分散すること、そしてこの芳香
族系炭化水素樹脂を分散させたポリオールの貯蔵安定性
が良好であり、ポリイソシアネ−１・化合物等と反応さ
せて造られるポリウレタンフォームは、歴青入りポリウ
レタンフォームと同様の良好な性状をもち、べたけき、
奥、汚染性等のなく、品質が良好で、性状の安定したポ
リウレタンフォームを得ることができることを知見した
。As a result of research into dispersing asphalt and other bituminous materials in polyol, the present inventors have found that aromatic hydrocarbon resins can be dispersed in polyol without or without the use of surfactants, dispersants, etc. Even if it is used, it can be dispersed well with a very small amount, and the polyol in which this aromatic hydrocarbon resin is dispersed has good storage stability. The polyurethane foam produced has good properties similar to those of bitumen-containing polyurethane foam.
Furthermore, it has been found that it is possible to obtain polyurethane foam that is free from contamination, has good quality, and has stable properties.
本発明は、このような知見にもとづいて完成したもので
ある。The present invention was completed based on such knowledge.
本発明の目的は、従来の歴青入りポリウレタンフォーム
の問題点を解消し、常温で発泡できると共に、注入成形
発泡ができ、製品のポリウレタンフォームはべた付き、
奥、汚染性等がなく、耐水性、耐候性等にすぐれたポリ
ウレタンフォームの製造方法を提供するものである。The purpose of the present invention is to solve the problems of conventional bitumen-containing polyurethane foam, which can be foamed at room temperature, and can be foamed by injection molding, and the polyurethane foam of the product is sticky.
The purpose of the present invention is to provide a method for producing polyurethane foam that is free from staining and has excellent water resistance, weather resistance, etc.
本発明は、ポリオール中に芳香族系炭化水素樹脂を微粒
子状に分散させておき、これとポリイソシアネート等を
混合し反応させてポリウレタンフォームを製造すること
を特徴とするポリウレタンフォームの製造方法を要旨と
するものである。The gist of the present invention is a method for producing polyurethane foam, which is characterized in that aromatic hydrocarbon resin is dispersed in polyol in the form of fine particles, and this is mixed with polyisocyanate and reacted to produce polyurethane foam. That is.
芳香族系炭化水素樹脂のポリオールへの分散は、粉砕機
、＠砕機、ミルなどで微粉砕した芳香族系炭化水素樹脂
粉末をポリオールに混合する方法、または、ポリオール
中に芳香族系炭化水素樹脂の粒子を混合しておいて磨砕
機、ミルなどを通して十分に粉砕し微粒子状に分散させ
る方法、あるいは、加熱溶融した芳香族系炭１ヒ水素樹
脂をポリオール中に添加しながらミキサーで混合する方
法、さらには、加熱溶融した芳香族系炭化水素樹脂をポ
リオールと共に乳化機に通してポリオール中に分散させ
る方法などがある４以上のいづれの方法も用いることが
できるが、加熱溶融した芳香族系炭化水素樹脂をミキサ
ー、乳化機等を用いてポリオール中に分散させる方法が
、分散が容易であるので効果的・である。The aromatic hydrocarbon resin can be dispersed in the polyol by mixing the aromatic hydrocarbon resin powder finely pulverized with a crusher, mill, etc. into the polyol, or by dispersing the aromatic hydrocarbon resin in the polyol. A method in which the particles are mixed and then sufficiently crushed through a grinder or mill to disperse them into fine particles, or a method in which heated and melted aromatic carbon-1-arsenic resin is added to the polyol and mixed in a mixer. Furthermore, any of the above four methods can be used, such as a method in which heat-melted aromatic hydrocarbon resin is passed through an emulsifier together with polyol and dispersed in the polyol, but heat-melted aromatic hydrocarbon resin A method of dispersing hydrogen resin in polyol using a mixer, emulsifier, etc. is effective because dispersion is easy.
本発明で使用する芳香族系炭化水素樹脂は、石油留分か
らフルフラール、フェノール等の溶剤で抽出して得られ
た芳香族成分に富む留分を２００〜３８０℃で重合して
得られる樹脂化合物、あるいは、Ｃ４、Ｃｓ留分を重合
して得られる樹脂化合物、更には、これらの混合物で、
熱可塑性であり、軟化点が大約４０〜１２０℃のもので
、平均分子量が大約３００〜８００．固定炭素が大約２
０〜５０重量％のものである０例えば、フッコールレヂ
ン（富士興産株式会社製、商品名）がある。The aromatic hydrocarbon resin used in the present invention is a resin compound obtained by polymerizing a fraction rich in aromatic components obtained by extracting a petroleum fraction with a solvent such as furfural or phenol at 200 to 380 ° C. Alternatively, a resin compound obtained by polymerizing C4, Cs fractions, or a mixture thereof,
It is thermoplastic, has a softening point of approximately 40 to 120°C, and has an average molecular weight of approximately 300 to 800. Fixed carbon is approximately 2
For example, Fukolresin (manufactured by Fuji Kosan Co., Ltd., trade name) contains 0 to 50% by weight.
フッコールレヂンの代表的性質をフッコールレヂンＰＲ
−１００（富士興産製、商品名）を例に示すと第１表の
ようである。Fukolresin PR about its typical properties
-100 (manufactured by Fuji Kosan, trade name) is shown in Table 1 as an example.
第 １ 表
芳香族系炭化水素樹脂と共に、芳香族系ないしナフテン
系の歴青、重質油、プロセスオイル、タール系高沸点油
分などを併用することもできる。Table 1 In addition to the aromatic hydrocarbon resins, aromatic or naphthenic bituminous oils, heavy oils, process oils, tar-based high-boiling oils, etc. can also be used in combination.
これらを併用する場合は、芳香族系炭化水素樹脂の５０
重量％以下で用いるようにする。When these are used together, 50% of the aromatic hydrocarbon resin
It should be used at less than % by weight.
本発明でいうポリオールは、ポリイソシアネートをポリ
オールと反応させてポリウレタンフォームを生成される
ための・ポリオールを含有している成分をいう、ポリオ
ール単味の場合のほか、ポリオール以外に可塑剤、充填
剤、触媒、架橋剤、発泡剤、その他が入っている場合も
ある。In the present invention, polyol refers to a component containing polyol, which is used to produce polyurethane foam by reacting polyisocyanate with polyol, and includes polyol alone as well as plasticizers and fillers in addition to polyol. , catalysts, crosslinking agents, blowing agents, and others.
本発明でいうポリイソシアネート等は、ポリイソシアネ
ートをポリオールと反応させポリウレタンフォームを生
成させるためのポリイソシアネートを含有している成分
をいう、ポリイソシアネート単味の場合のほか、ポリイ
ソシアネート以外の可塑剤、充填剤、触媒、架橋剤、発
泡剤、その他が入っている場合もある。In the present invention, polyisocyanate refers to a component containing polyisocyanate for producing polyurethane foam by reacting polyisocyanate with polyol, and includes polyisocyanate alone, as well as plasticizers other than polyisocyanate, It may also contain fillers, catalysts, crosslinking agents, blowing agents, and others.
上記のポリオール、ポリイソシアネート等は、いづれも
従来公知のものが使用される０例えば、ポリオールは、
分子中に２個以上の水酸基を有するもので、ポリエステ
ルポリオール、ポリエーテルポリオール、ポリマーポリ
オール、その他がある。ポリエステルポリオールは、例
えばアジピン酸、フタール酸、二ｌ化すルイン酸、マレ
イン酸などのジカルボン酸とエチレン、プロピレン、ブ
チレン、ジエチレンなどのグリコール、グリセリン、ト
リメチロールプロパン、ペンタエリスリトールなどのジ
オール、トリオール、ポリオールとを反応させて得られ
るポリオール、ひまし油などがある。ポリエーテルポリ
オールは、例えばプロピレングリコール、グリセリン、
トリメチロールプロパン、その他のポリオールやポリア
ミンにプロピレンオキサイド（ＰＯ）、エチレンオキサ
イド（ＥＯ）、ブチレンオキサイド、メチルトリメチレ
ンオギサイド、ジメチルトリメチレンオキサイドなどを
付加させたポリオールがある。ポリマーポリオールは、
例えばポリブタジェン、スチレン・ブタジェン共重合物
、ブタジェン・アクリルニトリル共重合物などの分子末
端や分子内に２個以上の水酸基をもつポリオールがある
。その他エチレングリコール、テレフタール酸の線状高
分子エステルのポリオール、アクリル酸の誘導体のアク
リルポリオールなどがある。The polyols, polyisocyanates, etc. mentioned above are all conventionally known ones. For example, the polyols are:
Those having two or more hydroxyl groups in the molecule include polyester polyols, polyether polyols, polymer polyols, and others. Polyester polyols include, for example, dicarboxylic acids such as adipic acid, phthalic acid, diphosphoric acid, and maleic acid, glycols such as ethylene, propylene, butylene, and diethylene, diols, triols, and polyols such as glycerin, trimethylolpropane, and pentaerythritol. There are polyols obtained by reacting with and castor oil. Polyether polyols include, for example, propylene glycol, glycerin,
There are polyols in which propylene oxide (PO), ethylene oxide (EO), butylene oxide, methyltrimethylene oxide, dimethyltrimethylene oxide, etc. are added to trimethylolpropane, other polyols, and polyamines. Polymer polyol is
For example, there are polyols having two or more hydroxyl groups at the end of the molecule or within the molecule, such as polybutadiene, styrene-butadiene copolymer, and butadiene-acrylonitrile copolymer. Other examples include polyols of linear polymeric esters of ethylene glycol and terephthalic acid, and acrylic polyols of acrylic acid derivatives.
ボリイ′ソシアネートとしては、例えば、トリレンジイ
ソシアネート（ＴＤ Ｉ ） 、ジフェニルメタンジイ
ソシアネート（ＭＤ Ｉ ） 、粗製ＭＤＩ、ヘキサメ
チレンジイソシアネート（ＨＭＤ Ｉ ） 、キシリレ
ンジイソシアネート（ＭＤ Ｉ ） 、水素添加ＴＤＩ
、水素添加ＭＤＩ、メタキシリレンジイソシアネート、
ポリメチレンポリフェニルイソシアネート（ＰＡＰＩ）
などがある、またこれらのポリイソシアネートとポリオ
ールとの反応によって得られる末端イソシアネート基含
有のプレポリマーを用いることもできる。可塑剤は、ポ
リウレタンの可塑剤や添加剤として使用されるもので、
ジエチルへキシルフタレート、ジオクチルフタレート、
ジブチルフタレート、ジオクチルアジペート、その他、
公知の可塑剤や、芳香族系ないしはナフテン系のプロセ
スオイルが用いられる。ポリウレタン製品の多くは可塑
剤を用いないが、充填剤などを加える場合に可塑剤を用
いることがある。Examples of polyisocyanates include tolylene diisocyanate (TD I ), diphenylmethane diisocyanate (MD I ), crude MDI, hexamethylene diisocyanate (HMD I ), xylylene diisocyanate (MD I ), and hydrogenated TDI.
, hydrogenated MDI, metaxylylene diisocyanate,
Polymethylene polyphenylisocyanate (PAPI)
Prepolymers containing terminal isocyanate groups obtained by reacting these polyisocyanates with polyols can also be used. Plasticizers are used as plasticizers and additives for polyurethane.
diethylhexyl phthalate, dioctyl phthalate,
Dibutyl phthalate, dioctyl adipate, others,
Known plasticizers and aromatic or naphthenic process oils are used. Most polyurethane products do not use plasticizers, but plasticizers may be used when fillers are added.
ポリウレタン原料として使用されるその他の材料、例え
ば充填剤、触媒、発泡剤、架橋剤、分散剤、助剤、その
他は、従来公知のものが使用される０ｇＡＪえば、芳香
族系炭化水素樹脂あるいはこれにプロセスオイル等を加
え、加熱溶融して液状にし、温度１００〜１４０℃位に
保ち、これを温度２０〜８０℃のポリオールとコロイド
ミル、ホモジナイザー、ホモミキサー等を用いて混合す
ることにより、ポリオール中に芳香族系炭化水素樹脂を
容易に分散させることができる０通常、界面活性剤、分
散剤等を使用しないで分散させることができる。界面活
性剤、分散剤等を少量使用することにより、より微粒子
状に分散できる。界面活性剤、分散剤等を使用するとき
は、ポリウレタンフォームの物性低下のない様に、その
使用量を出来る隔り少なくすべきである。Other materials used as polyurethane raw materials, such as fillers, catalysts, blowing agents, crosslinking agents, dispersants, auxiliaries, etc., are conventionally known materials. Add process oil, etc. to the liquid, heat and melt it to a liquid state, maintain the temperature at about 100 to 140 degrees Celsius, and mix this with polyol at a temperature of 20 to 80 degrees C using a colloid mill, homogenizer, homomixer, etc. to make polyol. The aromatic hydrocarbon resin can be easily dispersed in the resin. Normally, the aromatic hydrocarbon resin can be dispersed without using a surfactant, a dispersant, or the like. By using a small amount of surfactant, dispersant, etc., it is possible to disperse into finer particles. When using surfactants, dispersants, etc., the amount used should be as small as possible so as not to deteriorate the physical properties of the polyurethane foam.
ポリオール中へ芳香族炭化水素樹脂を分散させる際の両
者の割合は、通常重量割合でポリオール７０〜２５重量
％、芳香族系炭化水素樹脂３０〜２５重量％の範囲であ
る。一般には、ポリオール６０〜３０重量％、芳香族系
炭化水素樹脂４０〜７０重量％の範囲が用いられる。When the aromatic hydrocarbon resin is dispersed in the polyol, the ratio of the two is usually in the range of 70 to 25% by weight of the polyol and 30 to 25% by weight of the aromatic hydrocarbon resin. Generally, a range of 60 to 30% by weight of polyol and 40 to 70% by weight of aromatic hydrocarbon resin is used.
ポリオール中に分散させる芳香族系炭化水素樹脂は、微
粒子が好ましいが、かなり粗くても貯蔵安定性が良く、
分離がなく、また貯蔵中に芳香族系炭化水素樹脂の粒子
相互の凝集、団粒化等がない、また、粘度変化が少ない
等安定している０粒径は２〜１００ｍμ、通常３０μｍ
以下のものである。The aromatic hydrocarbon resin to be dispersed in the polyol is preferably fine particles, but even if it is quite coarse it has good storage stability.
There is no separation, there is no aggregation or agglomeration of aromatic hydrocarbon resin particles during storage, and there is little change in viscosity, etc., which is stable.The zero particle size is 2 to 100 mμ, usually 30 μm.
These are as follows.
ポリウレタンフォームは、上記のようにして造られた芳
香族系炭化水素樹脂、あるいはこれにプロセスオイル等
を加えたものを分散させたポリオールを用い、あるいは
これに更にポリオール等を加えたものを用いポリイソシ
アネート等と反応させて造られるが、ポリウレタンフォ
ームを生成させる方法は、公知の方法が使用される。Polyurethane foam is produced by using aromatic hydrocarbon resin produced as described above, polyol in which process oil, etc. is added, or polyol in which polyol, etc. is added. Polyurethane foam is produced by reacting with isocyanate, etc., and known methods can be used to produce polyurethane foam.
本発明の製造方法は、軟質、半硬質、硬質等のポリウレ
タンフォームに適用でき、流しこみ成形、注入成形、ス
プレー成形など種々の成形方法を採用できる。The manufacturing method of the present invention can be applied to soft, semi-rigid, rigid, etc. polyurethane foams, and various molding methods such as cast molding, injection molding, and spray molding can be employed.
本発明の製造方法により遣られたポリウレタンフォーム
は、ポリウレタンフォーム組織中に芳香族系炭化水素樹
脂が微粒子状に均一に分散結合している。ポリウレタン
フォーム中に分散している芳香族系炭化水素樹脂は、熱
可塑性で耐水性、耐候性、耐薬品性等にすぐれているの
で、歴青入りポリウレタンフォームと同様の耐水性、耐
候性、耐薬品性の向上、低周波の振動、音の吸収効果等
を発揮できる。In the polyurethane foam produced by the production method of the present invention, aromatic hydrocarbon resin is uniformly dispersed and bonded in the form of fine particles in the polyurethane foam structure. The aromatic hydrocarbon resin dispersed in polyurethane foam is thermoplastic and has excellent water resistance, weather resistance, and chemical resistance, so it has the same water resistance, weather resistance, and chemical resistance as bitumen-containing polyurethane foam. It can improve chemical properties, absorb low-frequency vibrations, and absorb sound.
また、芳香族系炭化水素樹脂を分散させたポリオールを
使用してポリウレタンフォームを遣るため、芳香族炭化
水素樹脂粒子は、奥、汚染性等がないうえ、ポリウレタ
ン組織でおおわれているので、粘着性、汚染性、臭等が
ない、また、芳香族系炭化水素樹脂は、ポリウレタンと
の親和性が良いうえ、化学的に不活性で安定であること
から、ポリウレタンフォーム化反応を害することがない
のでポリウレタンフォーム原料のほか薬剤、触媒、架橋
剤、発泡剤、助剤、その他の公知のものを使用し、公知
の方法でポリウレタンフォームを造ることができる。In addition, since polyurethane foam is produced using a polyol in which aromatic hydrocarbon resin is dispersed, the aromatic hydrocarbon resin particles are free from contamination and are covered with a polyurethane structure, making them sticky. In addition, aromatic hydrocarbon resins have good affinity with polyurethane and are chemically inert and stable, so they do not harm the polyurethane foaming reaction. Polyurethane foam can be produced by a known method using chemicals, catalysts, crosslinking agents, blowing agents, auxiliary agents, and other known materials in addition to polyurethane foam raw materials.
次に、本発明の詳細な説明する。Next, the present invention will be explained in detail.
実施例に使用した芳香族系炭化水素樹脂は、富士興産株
式会社製の商品名フッコールレヂンＦＲ−４０（軟化点
４０℃）およびＦＲ−６０（軟化点６０℃）である。The aromatic hydrocarbon resins used in the examples were Fukolresin FR-40 (softening point 40°C) and FR-60 (softening point 60°C) manufactured by Fuji Kosan Co., Ltd.
芳香族系炭化水素樹脂のポリオールへの分散実験実験
１
フッコールレヂンＰＲ−４０，あるいは、５これに芳香
族系プロセスオイルを加えたものを約１１０℃に加熱Ｎ
融しておき、これを約８０’Ｃのグリセリン系ポリエー
テルポリオール（平均分子量的３０００）中にホモミキ
サー（回転数７０００〜７５００ｒｐｍ＞を用いて分散
させた。処理量的５００ｇ、混合時間約３分間である。Dispersion experiment of aromatic hydrocarbon resin in polyol
1 Flucoresin PR-40 or 5 Add aromatic process oil to it and heat to about 110℃ N
This was melted and dispersed in glycerin-based polyether polyol (average molecular weight: 3,000) at about 80'C using a homomixer (rotation speed: 7,000 to 7,500 rpm). Processing amount: 500 g, mixing time: about 3 It is a minute.
配合、分散性および分散物の粒度、粒径等を第２表に示
す。The formulation, dispersibility, particle size of the dispersion, etc. are shown in Table 2.
界面活性剤、分散剤等を使用しないでも良好な分散を示
している。Good dispersion is shown even without using surfactants, dispersants, etc.
実験 ２
実験１のフッコールレヂンの代りにフッコールレヂンＰ
Ｒ−６０を用いて実験１を同様に分散実験を行ったが分
散性良好であった。Experiment 2 Fuccolesin P instead of Fuccolesin in Experiment 1
A dispersion experiment was conducted in the same manner as in Experiment 1 using R-60, and the dispersibility was good.
第 ２ 表 ネ粒径は、コールタ−カウンターによって測定。Table 2 The particle size was measured using a Coulter counter.
実験１についていえば、分散粒子の２５％までが、１０
．７３μｍ以下、分散粒子の５０％までが１４．４５μ
ｍ以下、分散粒子の７５％までが２２．５６μｍ以下で
あることを示す。Regarding experiment 1, up to 25% of the dispersed particles were 10
．． 73μm or less, up to 50% of dispersed particles are 14.45μm
m or less indicates that up to 75% of the dispersed particles are 22.56 μm or less.
実施例 １
グリセリン系ポリエーテルポリオール（平均分子通約３
０００）５０重量部にフツコールレヂンＰＲ−４０５０
重量部を実験１の方法で分散し、芳香族系炭化水素樹脂
濃度５０重量％のポリオール分散液を遺る。Example 1 Glycerin-based polyether polyol (average molecular weight approximately 3
000) 50 parts by weight of Futukol Resin PR-4050
Parts by weight were dispersed by the method of Experiment 1, leaving a polyol dispersion with an aromatic hydrocarbon resin concentration of 50% by weight.
この芳香族系炭化水素樹脂のポリオール分散液１００重
量部に上記ポリオール５０重量部を添加混合したものと
、トリレンジイソシアネート（ＴＤＩ）５０重量部と水
４重１部にトリエチレンジアミン０．２重量部、スタナ
スオクトエート０゜３重量部、シリコン安定剤（気泡安
定剤）２重量部を加えたものとを容器に入れ、撹拌機で
すばやく混合撹拌し、シート上に流してフオーム化反応
をさせ、ポリウレタンフォームを得た。A mixture of 50 parts by weight of the above polyol added to 100 parts by weight of this polyol dispersion of aromatic hydrocarbon resin, 50 parts by weight of tolylene diisocyanate (TDI), 1 part by weight of 4 parts of water, and 0.2 parts by weight of triethylenediamine. , 0.3 parts by weight of Stanus octoate, and 2 parts by weight of silicone stabilizer (bubble stabilizer) were added to a container, quickly mixed and stirred with a stirrer, and poured onto a sheet to cause a forming reaction. , polyurethane foam was obtained.
このポリウレタンフォームは、−様に発泡しており、ポ
リウレタン組織に芳香族系炭化水素樹脂が一様に分散結
合している。また、無臭で、べた付きや、汚染性が全く
見られない良好なポリウレタンフォームである。This polyurethane foam is foamed in a --like manner, and the aromatic hydrocarbon resin is uniformly dispersed and bonded to the polyurethane structure. In addition, it is a good polyurethane foam that is odorless and shows no stickiness or staining properties.
実施例 ２
グリセリン系プロピレンオキサイドとエチレンオキサイ
ド付加物のポリエーテルポリオール（平均分子量３，０
００）１００重量部にフッコールレヂンＦＲ−４０６０
重量部を実＠１の方法で添加混合する。この芳香族系炭
化水素樹脂のポリオール分散液１６０重量部と、水４重
量部にトリエチレンジアミン０．２重量部、スタナスオ
クトエート０．３重量部、シリコン安定剤（水溶性シリ
コン油）１．５重量部を加えたものと、ＴＤＩ４８重量
部とを容器に入れ、すばやく撹拌機で混合撹拌し、シー
ト上に流してフオーム反応させ、ポリウレタンフォーム
を得た。Example 2 Polyether polyol of glycerin-based propylene oxide and ethylene oxide adduct (average molecular weight 3.0
00) 100 parts by weight of Fukol resin FR-4060
Parts by weight are added and mixed in the same manner as in Example 1. 160 parts by weight of this polyol dispersion of aromatic hydrocarbon resin, 0.2 parts by weight of triethylenediamine, 0.3 parts by weight of stannath octoate, 1.0 parts by weight of silicone stabilizer (water-soluble silicone oil), 4 parts by weight of water. The mixture containing 5 parts by weight and 48 parts by weight of TDI were placed in a container, quickly mixed and stirred using a stirrer, and poured onto a sheet to cause a foam reaction, thereby obtaining a polyurethane foam.
このポリウレタンフォームは、芳香族系炭化水素樹脂が
ポリウレタン組織に一様に分散して結合し、発泡状態も
良好である。また、無臭で、べた付き、汚染性が全くな
く良好である。In this polyurethane foam, the aromatic hydrocarbon resin is uniformly dispersed and bonded to the polyurethane structure, and the foaming state is also good. In addition, it is odorless, non-sticky, and non-staining.
実施例 ３
グリセリン系ポリエーテルポリオール（平均分子量３０
００）１００重量部に、フッコールレヂンＦＲ−４０５
９重量部と芳香族系プロセスオイル６重量部の混合物を
実験１の方法で分散させる。この芳香族系炭化水素樹脂
のポリオール分散液と、ＴＤＩ４８重量部と水４重量部
にトリエチレンジアミン０．２重量部、スタナスオクト
エート０．３重量部、シリコン安定剤１．５重量部を加
えたものとを容器に入れて、すばやく撹拌機で混合撹拌
し、シート上に流してフオーム化反応をさせ、ポリウレ
タンフォームを得た。Example 3 Glycerin-based polyether polyol (average molecular weight 30
00) 100 parts by weight, Fukolresin FR-405
A mixture of 9 parts by weight and 6 parts by weight of aromatic processing oil is dispersed by the method of Experiment 1. To this polyol dispersion of aromatic hydrocarbon resin, 48 parts by weight of TDI, and 4 parts by weight of water, 0.2 parts by weight of triethylenediamine, 0.3 parts by weight of stannath octoate, and 1.5 parts by weight of silicone stabilizer were added. The mixture was put into a container, quickly mixed and stirred with a stirrer, and poured onto a sheet to cause a foaming reaction, thereby obtaining polyurethane foam.
このポリウレタンフォームは、芳香族系炭化水素樹脂が
ポリウレタン組織に一様に分散して結合し、発泡も良好
である。また、無臭で、べた付き、汚染性がない良好な
フオームである。In this polyurethane foam, the aromatic hydrocarbon resin is uniformly dispersed and bonded to the polyurethane structure, and foaming is also good. It also has a good foam that is odorless, non-sticky, and non-staining.
特許出願人 日瀝化学工業株式会社Patent applicant: Nissei Chemical Industry Co., Ltd.
Claims (1)
に分散させておき、これとポリイソシアネート等を混合
し反応させてポリウレタンフォームを製造することを特
徴とするポリウレタンフォームの製造方法。(1) A method for producing a polyurethane foam, which comprises dispersing an aromatic carbon hydrogen resin in the form of fine particles in a polyol, and mixing and reacting this with a polyisocyanate or the like to produce a polyurethane foam.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63127146A JPH01299814A (en) | 1988-05-26 | 1988-05-26 | Preparation of polyurethane foam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63127146A JPH01299814A (en) | 1988-05-26 | 1988-05-26 | Preparation of polyurethane foam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01299814A true JPH01299814A (en) | 1989-12-04 |
Family
ID=14952756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63127146A Pending JPH01299814A (en) | 1988-05-26 | 1988-05-26 | Preparation of polyurethane foam |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01299814A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0680752A (en) * | 1991-09-25 | 1994-03-22 | Mitsuboshi Belting Ltd | Molded polyurethane article for vibration damping and its production |
| US5798411A (en) * | 1997-09-19 | 1998-08-25 | The Hygenic Corporation | Compressible polyurethane compositions having minimal tack and articles therefrom |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52151395A (en) * | 1976-06-04 | 1977-12-15 | Nhk Spring Co Ltd | Foamed polyurethane excellent in waterrresistance and process for producing same |
| JPS5328698A (en) * | 1976-08-28 | 1978-03-17 | Nhk Spring Co Ltd | Urethane foam excellent in waterrproof and process for producing same |
| JPS543199A (en) * | 1977-06-09 | 1979-01-11 | Nhk Spring Co Ltd | High acoustic and damping foam and method of making it |
| JPS5477697A (en) * | 1977-12-03 | 1979-06-21 | Nhk Spring Co Ltd | Production of hydrophobic urethane foamed body |
| JPS62265383A (en) * | 1986-05-13 | 1987-11-18 | Bridgestone Corp | Polyurethane foam sealant |
| JPS63273663A (en) * | 1987-05-02 | 1988-11-10 | Nhk Spring Co Ltd | Production of polyurethane foam containing bituminous substance |
| JPS6416864A (en) * | 1987-07-10 | 1989-01-20 | Nichireki Chem Ind Co | Ant-controlling polyurethane foam |
-
1988
- 1988-05-26 JP JP63127146A patent/JPH01299814A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52151395A (en) * | 1976-06-04 | 1977-12-15 | Nhk Spring Co Ltd | Foamed polyurethane excellent in waterrresistance and process for producing same |
| JPS5328698A (en) * | 1976-08-28 | 1978-03-17 | Nhk Spring Co Ltd | Urethane foam excellent in waterrproof and process for producing same |
| JPS543199A (en) * | 1977-06-09 | 1979-01-11 | Nhk Spring Co Ltd | High acoustic and damping foam and method of making it |
| JPS5477697A (en) * | 1977-12-03 | 1979-06-21 | Nhk Spring Co Ltd | Production of hydrophobic urethane foamed body |
| JPS62265383A (en) * | 1986-05-13 | 1987-11-18 | Bridgestone Corp | Polyurethane foam sealant |
| JPS63273663A (en) * | 1987-05-02 | 1988-11-10 | Nhk Spring Co Ltd | Production of polyurethane foam containing bituminous substance |
| JPS6416864A (en) * | 1987-07-10 | 1989-01-20 | Nichireki Chem Ind Co | Ant-controlling polyurethane foam |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0680752A (en) * | 1991-09-25 | 1994-03-22 | Mitsuboshi Belting Ltd | Molded polyurethane article for vibration damping and its production |
| US5798411A (en) * | 1997-09-19 | 1998-08-25 | The Hygenic Corporation | Compressible polyurethane compositions having minimal tack and articles therefrom |
| US6084027A (en) * | 1997-09-19 | 2000-07-04 | The Hygenic Corporation | Compressible polyurethane compositions having minimal tack and articles therefrom |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1120648A (en) | Process for the manufacture of reinforced polyurethane foams | |
| EP0202732B1 (en) | Method for the preparation of semi-rigid polyurethane modified polyurea foam compositions | |
| KR0173787B1 (en) | Polyurethane and/or polyurea dispersions in active hydrogen-containing compositions, a process for preparing same a..... | |
| KR100358468B1 (en) | A method for preparing a flexible polyurethane foam and a flexible polyurethane foam made by such method | |
| AU2019236120B2 (en) | Flexible polyurethane foam having prolonged recovery time | |
| JPH08509249A (en) | Foamed polymer and method for producing the same | |
| KR970059196A (en) | Polymer Polyols and Methods for Making the Same | |
| JPH0723418B2 (en) | Method for producing polyurethane foam containing asphalt | |
| JPH0797426A (en) | Fine polyurethane gel particles and its production | |
| US3787525A (en) | Manufacture of polyurethane powders using polyvinyl pyrrolidone having side chains from copolymerization with alkylated olefins | |
| CA2245306A1 (en) | Storage-stable, blowing agent-containing emulsions for producing rigid foams based on isocyanate | |
| JPH01299814A (en) | Preparation of polyurethane foam | |
| JPS6253371A (en) | Asphalt-containing polyurethane and production thereof | |
| US20220372287A1 (en) | Isocyanate-reactive composition | |
| JPS62101651A (en) | Bitumen-filled polyurethane | |
| JPS6150965B2 (en) | ||
| JP2526974B2 (en) | Method for producing foamed synthetic resin | |
| JP3624448B2 (en) | Manufacturing method of rigid foam | |
| JPH0830104B2 (en) | Method for producing foamed synthetic resin | |
| JP4178384B2 (en) | Rigid polyurethane foam molding composition and method for producing rigid polyurethane foam using the composition | |
| RU2648097C1 (en) | Method of getting a polymer-bitumen bending based on foamed polyurethane | |
| JPH0797424A (en) | Fine water-absorbing polyurethane gel particle and its production | |
| US1762194A (en) | Composition of matter | |
| US1822249A (en) | of akron | |
| JPS62104866A (en) | Production of modified asphalt emulsion |