JPH02145557A - Modified polymethylene polyphenyl polyisocyanate - Google Patents
Modified polymethylene polyphenyl polyisocyanateInfo
- Publication number
- JPH02145557A JPH02145557A JP63301938A JP30193888A JPH02145557A JP H02145557 A JPH02145557 A JP H02145557A JP 63301938 A JP63301938 A JP 63301938A JP 30193888 A JP30193888 A JP 30193888A JP H02145557 A JPH02145557 A JP H02145557A
- Authority
- JP
- Japan
- Prior art keywords
- polymethylene polyphenyl
- polyphenyl polyisocyanate
- diphenylmethane diisocyanate
- polyol
- modified
- 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
- -1 polymethylene Polymers 0.000 title claims abstract description 13
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 12
- 229920006389 polyphenyl polymer Polymers 0.000 title claims abstract description 12
- 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 abstract description 21
- 229920005862 polyol Polymers 0.000 claims abstract description 16
- 150000003077 polyols Chemical class 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 6
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims abstract description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000007858 starting material Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 229920005830 Polyurethane Foam Polymers 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 239000011496 polyurethane foam Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 238000013035 low temperature curing Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 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 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920002323 Silicone foam Polymers 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000013514 silicone foam Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、低温硬化型可撓性ポリウレタンフォームの原
料として用いられる低温で長期間貯蔵安定性を有する変
性ポリメチレンポリフェニルポリイソシアネートに関す
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a modified polymethylene polyphenyl polyisocyanate having long-term storage stability at low temperatures and used as a raw material for low temperature curing flexible polyurethane foam.
［従来の技術］
低温硬化型可撓性ポリウレタンフォームの原料として、
２，４′−ジフェニルメタンジイソシアネート（以下２
．４’−ＭＤＩという）、４，４′−ジフェニルメタン
ジイソシアネート（以下４゜４’−ＭＤＩという）およ
びオリゴマーポリメチレンポリフェニルポリイソシアネ
ート（以下オリゴマーＭＤＩという）を含有するポリメ
チレンポリフェニルポリイソシアネート（以下クルード
ＭＤＩという）を用いることは知られている（特開昭５
３−５１．２９９号公報、特開昭５７−１４５６２０号
公報）が、冬季には、貯蔵中に結晶や不溶物を析出しや
すく、−旦結晶が析出すれば、これを加熱して溶かさな
ければならない。このためクルードＭＤＩをポリエーテ
ルジオール、ポリエーテルトリオールまたはポリエステ
ルポリオールで変性する方法が提案されている（特開昭
５７−１０９８２０号公報、特開昭６２−１１２６１６
号公報、特開昭６５−１７７０１３号公報）。しかしな
がら、このような変性をしても、低温で長期間安定に貯
蔵するためには、必らずしも充分でない。さらに結晶を
析出したものを加熱して溶かすことなく原料として用い
た場合、得られる低温硬化壁可撓性ポリウレタンフォー
ムは、湾曲状に変形を起こしやすい。[Conventional technology] As a raw material for low temperature curing flexible polyurethane foam,
2,4'-diphenylmethane diisocyanate (hereinafter referred to as 2
．． 4'-MDI), 4,4'-diphenylmethane diisocyanate (hereinafter referred to as 4゜4'-MDI), and oligomeric polymethylene polyphenyl polyisocyanate (hereinafter referred to as oligomer MDI). It is known that the use of
3-51.299, JP-A-57-145620), crystals and insoluble matter tend to precipitate during storage in winter, and once crystals precipitate, they must be melted by heating. Must be. For this reason, a method of modifying crude MDI with polyether diol, polyether triol, or polyester polyol has been proposed (Japanese Patent Laid-Open Nos. 57-109820, 62-112616).
(Japanese Unexamined Patent Publication No. 177013/1982). However, even such modification is not necessarily sufficient for stable storage at low temperatures for long periods of time. Furthermore, if the precipitated crystals are used as a raw material without being heated and melted, the resulting low-temperature cured wall flexible polyurethane foam is likely to be deformed into a curved shape.
［発明が解決しようとする課題］
本発明者らは、このような課題を解決すべく鋭意検討を
重ねた結果、２．４’−ＭＤＩを多く含むクルードＭＤ
Ｉ（以下２，４′−リッチクルードＭＤＩという）を、
ある種のポリオールで変性すれば、低温で長期間貯蔵し
ても結晶が析出することなく、さらにこれを加熱するこ
となく原料として用いても、得られる低温硬化型可撓性
ポリウレタンフォームは、湾曲状に変形しないことを見
い出し、本発明を完成した。[Problems to be Solved by the Invention] As a result of intensive studies to solve these problems, the present inventors have developed a crude MD containing a large amount of 2.4'-MDI.
I (hereinafter referred to as 2,4'-rich crude MDI),
When modified with a certain type of polyol, crystals do not precipitate even when stored at low temperatures for long periods of time, and even when used as a raw material without heating, the resulting low-temperature-curing flexible polyurethane foam can be curved. The present invention was completed based on the discovery that the material does not deform in the shape of the material.
［課題を解決するための手段］
本発明は、２．４’−ＭＤＩａ瑣量％、４，４′ＭＤＩ
ｂ重量％およびオリゴマーＭＤＩｃ重量％を含有し、ａ
、 ｂおよびＣが、それぞれ３≦ａ≦３０．６０≦ｂ
≦９０．７０≦ａ＋ｂ≦９５および５≦ｃ≦３０の条件
を満たす２．４′ −リツチクールドＭＤＩを、プロピ
レンオキシド（以下ＰＯという）およびエチレンオキシ
ド（以下Ｅ Ｏという）を４価以上の鎖状アルコールに
付加させたポリオールで、全イソシアネート基の１７％
以下を変性したポリメチレンポリフェニルポリイソシア
ネート（以下変性クールドＭＤＩという）に関する。[Means for Solving the Problems] The present invention provides 2.4'-MDIa trivial %, 4,4'MDI
b wt% and oligomeric MDIc wt%; a
, b and C are 3≦a≦30.60≦b, respectively
Propylene oxide (hereinafter referred to as PO) and ethylene oxide (hereinafter referred to as EO) were combined with 2.4'-rich-curd MDI that satisfies the conditions of ≦90.70≦a+b≦95 and 5≦c≦30 into a tetrahydric or higher chain alcohol. Polyol added to 17% of total isocyanate groups
This invention relates to polymethylene polyphenyl polyisocyanate (hereinafter referred to as modified cooled MDI) modified with the following.
２、４′−リッチクルードＭＤＩは、例えば、アニリン
とホルムアルデヒドの縮合物をホスゲン化反応すること
により（りられるもので、２．４′−ＭＤ Ｉ、４．４
’−ＭＤＩおよび三核体以上のオリゴマーＭＤＩの混合
物であるが、通常のクルードＭＤＩよりも２．４’−Ｍ
ＤＩを多く含む。2,4'-rich crude MDI can be obtained, for example, by phosgenation reaction of a condensate of aniline and formaldehyde.
'-MDI and trinuclear or higher oligomeric MDI, but 2.4'-MDI is more
Contains a lot of DI.
このものは少量の２．２′−ジフェニルメタンジイソシ
アネートなどを含有していてもよい。This may contain a small amount of 2,2'-diphenylmethane diisocyanate and the like.
４価以上の鎖状アルコールは、ソルビトール、ペンタエ
リスリトール、マンニトール、イジトールなどであるが
、ソルビトールやペンタエリスリトールが好ましい。Examples of the chain alcohol having a valence of 4 or more include sorbitol, pentaerythritol, mannitol, iditol, etc., and sorbitol and pentaerythritol are preferable.
変性剤として用いるポリオールは、４価以上の鎖状アル
コールにＰＯおよびＥＯをアルカリ条件下で（Ｊ加させ
たものであるが、１０重量％以上のＥＯを含むＥＯとＰ
Ｏの混合物を４価以上の鎖状アルコールに付加させたも
のであって、かつ分子量が４０００から１５０００のも
のが好ましい。The polyol used as a modifier is obtained by adding PO and EO to a chain alcohol with a valence of 4 or more under alkaline conditions (J), but EO and P containing 10% by weight or more of EO are
It is preferably one in which a mixture of O is added to a chain alcohol having a valence of four or more, and the molecular weight is from 4,000 to 15,000.
本発明の変性クルードＭＤＩは、２，４′ −リッチク
ルードＭＤＩをポリオールで、通常４０℃〜１２０°Ｃ
で、全イソシアネート基の１７％以下を変性することに
よって得られる。１７％を越えて変性すると、得られる
変性クルードＭＤＩの粘度が高くなり、ポリエーテルポ
リオールとの反応性が低下する。The modified crude MDI of the present invention is prepared by converting 2,4'-rich crude MDI into a polyol, usually at a temperature of 40°C to 120°C.
It is obtained by modifying not more than 17% of the total isocyanate groups. If it is modified by more than 17%, the viscosity of the resulting modified crude MDI increases and the reactivity with polyether polyol decreases.
この様にして（ｑられた変性クルードＭＤＩは、ポリエ
ーテルポリオール、発泡剤、触媒、架橋剤、その他添加
剤などと混合し、７０ ’Ｃ以下の温度に調節したモー
ルド中で反応させることにより、低温硬化型可撓性ポリ
ウレタンフォームを得ることが出来る。The modified crude MDI thus obtained is mixed with polyether polyol, blowing agent, catalyst, crosslinking agent, other additives, etc., and reacted in a mold controlled at a temperature of 70'C or less. A low temperature curing flexible polyurethane foam can be obtained.
［実施例］
２．４’−ＭＤＩ２０重量％、４．４’−ＭＤＩ７０重
量％およびオリゴマーＭＤＩＩＯ重量％からなるイソシ
アネート含有量が３２．５ｆｉ量％の２．４′−リッチ
クルードＭＤＩ１００重量部を７０℃に加熱し、これに
ＰｏとＥＯの重量比が８４対１６の混合アルキレンオキ
シドをソルビト−ルに付加して得られる分子量約１２０
００のポリオール（以下ポリオール１という）あるいは
、この混合アルキレンオキシドをペンタエリスリトール
に付加して得られる分子量約６４００のポリオール（以
下ポリオール２という）の表１に示す重量部をそれぞれ
徐々に加え、７０°Ｃで４時間反応させて、変性クルー
ドＭＤＩを得た。このもののイソシアネート含有酸およ
び変性に使われたイソシアネート基の割合を表１に示す
。[Example] 70 parts by weight of 100 parts by weight of 2.4'-rich crude MDI with an isocyanate content of 32.5% by weight consisting of 20% by weight of 2.4'-MDI, 70% by weight of 4.4'-MDI and 70% by weight of oligomer MDIIO. ℃, and add a mixed alkylene oxide with a weight ratio of Po and EO of 84:16 to sorbitol with a molecular weight of about 120.
00 (hereinafter referred to as polyol 1) or a polyol with a molecular weight of approximately 6,400 obtained by adding this mixed alkylene oxide to pentaerythritol (hereinafter referred to as polyol 2), the weight parts shown in Table 1 were gradually added, and the mixture was heated at 70° The reaction mixture was reacted at C for 4 hours to obtain modified crude MDI. Table 1 shows the isocyanate-containing acid and the proportion of isocyanate groups used for modification.
この変性クルードＭＤＩを窒素ガスでシールしたガラス
容器に入れ、５°Ｃの恒温槽中で保存し、目視により結
晶が析出しはじめるまでの日数（以下結晶析出日数とい
う）を求めた。This modified crude MDI was placed in a glass container sealed with nitrogen gas and stored in a constant temperature bath at 5°C, and the number of days until crystals started to precipitate (hereinafter referred to as the number of days for crystal precipitation) was determined by visual observation.
２週間後に恒温槽から取り出した変性クルードＭＤＩに
、ｐｏとＥＯの重量比が８５対１５の混合アルキレンオ
キシドをトリメチロールプロパンに付加して得られる分
子量的４８００のポリエーテルポリオール１００重量部
、トリエタノールアミン３重量部、水３重量部、 トリ
エチレンジアミン０，５重量部およびシリコーン系整泡
剤０．５重量部からなる混合物を、イソシアネート基と
水酸基の当量比が１対１になる様に加え、直ちに２００
Ｏｒｐｍの撹拌機で混合した後、縦、横、高さがそれぞ
れ３０ｃｍ、３０ｃ＋ａ、１０ｃｍで、温度５０°Ｃの
角型のアルミ製モールドに、フオーム密度が６０ｋｇ／
ｍ’になる様に注入した。型締後３分でフオームを取り
出し、室温で１時間放置した後、フオームの湾曲状の変
形の有無を調べた。結果を表１に示す。100 parts by weight of a polyether polyol with a molecular weight of 4800 obtained by adding mixed alkylene oxide with a weight ratio of po and EO of 85:15 to trimethylolpropane and triethanol were added to the modified crude MDI taken out from the thermostatic chamber after two weeks. A mixture consisting of 3 parts by weight of amine, 3 parts by weight of water, 0.5 parts by weight of triethylenediamine and 0.5 parts by weight of a silicone foam stabilizer was added so that the equivalent ratio of isocyanate groups to hydroxyl groups was 1:1, 200 immediately
After mixing with an Orpm stirrer, the foam density was 60 kg/cm in a rectangular aluminum mold with length, width, and height of 30 cm, 30 c+a, and 10 cm, respectively, and a temperature of 50 °C.
It was injected so that the amount was m'. The foam was taken out 3 minutes after mold clamping, and after being left at room temperature for 1 hour, the presence or absence of curved deformation of the foam was examined. The results are shown in Table 1.
比較例としてポリオール１あるいはポリオール２に代え
て、ＰＯとＥＯの重量比が８４対１６の混合アルキレン
オキシドをグリセリンに付加して得られる分子量的６０
００のポリエーテルトリオール（以下ポリオール３とい
う）の表１に示す重量部を加えた以外は実施例と同様に
行ない、結晶析出日数とフオームの湾曲状の変形の有無
を調べた。結果を表１に示す。As a comparative example, in place of polyol 1 or polyol 2, a mixed alkylene oxide with a weight ratio of PO and EO of 84:16 was added to glycerin with a molecular weight of 60.
The same procedure as in Example was carried out except that the weight parts shown in Table 1 of polyether triol No. 00 (hereinafter referred to as polyol 3) were added, and the number of days for crystal precipitation and the presence or absence of curved deformation of the foam were examined. The results are shown in Table 1.
表 １
［発明の効果］
実施例および比較例から明らかなように、本発明の変性
クルードＭＤＩは、低温で結晶が析出し難い。しかもこ
れを用いて得られたフオームは、湾曲状に変形を起こさ
なかった。従って、本発明の変性クルードＭＤＩは、低
温で長期間安定に貯蔵することが出来る。Table 1 [Effects of the Invention] As is clear from the Examples and Comparative Examples, the modified crude MDI of the present invention is difficult to precipitate crystals at low temperatures. Moreover, the foam obtained using this did not undergo any deformation into a curved shape. Therefore, the modified crude MDI of the present invention can be stably stored at low temperatures for a long period of time.
以上that's all
Claims (1)
量％、４，４′−ジフェニルメタンジイソシアネートｂ
重量％およびオリゴマーポリメチレンポリフェニルポリ
イソシアネートｃ重量％を含有し、ａ、ｂおよびｃが、
それぞれ３≦ａ≦３０、６０≦ｂ≦９０、７０≦ａ＋ｂ
≦９５および５≦ｃ≦３０の条件を満たす２，４′−ジ
フェニルメタンジイソシアネートを多く含むポリメチレ
ンポリフェニルポリイソシアネートを、プロピレンオキ
シドおよびエチレンオキシドを４価以上の鎖状アルコー
ルに付加させたポリオールで、全イソシアネート基の１
７％以下を変性したポリメチレンポリフェニルポリイソ
シアネート1,2,4'-diphenylmethane diisocyanate a wt%, 4,4'-diphenylmethane diisocyanate b
% by weight and oligomeric polymethylene polyphenyl polyisocyanate c, where a, b and c are
3≦a≦30, 60≦b≦90, 70≦a+b, respectively
Polymethylene polyphenyl polyisocyanate containing a large amount of 2,4'-diphenylmethane diisocyanate, which satisfies the conditions of ≦95 and 5≦c≦30, is completely combined with a polyol in which propylene oxide and ethylene oxide are added to a chain alcohol with a valence of 4 or more. 1 of the isocyanate groups
Polymethylene polyphenyl polyisocyanate modified with 7% or less
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63301938A JPH02145557A (en) | 1988-11-28 | 1988-11-28 | Modified polymethylene polyphenyl polyisocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63301938A JPH02145557A (en) | 1988-11-28 | 1988-11-28 | Modified polymethylene polyphenyl polyisocyanate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02145557A true JPH02145557A (en) | 1990-06-05 |
Family
ID=17902917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63301938A Pending JPH02145557A (en) | 1988-11-28 | 1988-11-28 | Modified polymethylene polyphenyl polyisocyanate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02145557A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5240991A (en) * | 1991-06-05 | 1993-08-31 | Dow Mitsubishi Kasei Limited | Polyisocyanate composition |
| US5248714A (en) * | 1990-10-31 | 1993-09-28 | Dow Mitsubishi Kasei Limited | Polyisocyanate composition |
| WO2011024413A1 (en) * | 2009-08-29 | 2011-03-03 | 日本ポリウレタン工業株式会社 | Soft polyurethane foam and manufacturing method therefor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5980426A (en) * | 1982-10-29 | 1984-05-09 | Asahi Glass Co Ltd | Production of polyurethane elastomer |
| JPH0229417A (en) * | 1988-06-02 | 1990-01-31 | Bayer Ag | Liquid polyisocyanate composition, production thereof and use thereof for producing soft polyurethane foam |
-
1988
- 1988-11-28 JP JP63301938A patent/JPH02145557A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5980426A (en) * | 1982-10-29 | 1984-05-09 | Asahi Glass Co Ltd | Production of polyurethane elastomer |
| JPH0229417A (en) * | 1988-06-02 | 1990-01-31 | Bayer Ag | Liquid polyisocyanate composition, production thereof and use thereof for producing soft polyurethane foam |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248714A (en) * | 1990-10-31 | 1993-09-28 | Dow Mitsubishi Kasei Limited | Polyisocyanate composition |
| US5240991A (en) * | 1991-06-05 | 1993-08-31 | Dow Mitsubishi Kasei Limited | Polyisocyanate composition |
| WO2011024413A1 (en) * | 2009-08-29 | 2011-03-03 | 日本ポリウレタン工業株式会社 | Soft polyurethane foam and manufacturing method therefor |
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