JPS63117045A - Production of open-cell rigid urethane foam - Google Patents
Production of open-cell rigid urethane foamInfo
- Publication number
- JPS63117045A JPS63117045A JP26197586A JP26197586A JPS63117045A JP S63117045 A JPS63117045 A JP S63117045A JP 26197586 A JP26197586 A JP 26197586A JP 26197586 A JP26197586 A JP 26197586A JP S63117045 A JPS63117045 A JP S63117045A
- Authority
- JP
- Japan
- Prior art keywords
- urethane foam
- open
- org
- polyisocyanate
- pyrrolidone
- 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
- 239000006260 foam Substances 0.000 title claims abstract description 31
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 16
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000012948 isocyanate Substances 0.000 claims description 11
- 150000002513 isocyanates Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 229920005862 polyol Polymers 0.000 abstract description 2
- 150000003077 polyols Chemical class 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 238000000034 method Methods 0.000 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 description 6
- 230000005484 gravity Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 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 2
- 239000012528 membrane Substances 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000758 substrate 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
- 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 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- -1 isocyanate compound Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Landscapes
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は靭性、強度および接着性に優れた連通気泡性硬
質ウレタンフオームの製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing an open-cell rigid urethane foam having excellent toughness, strength and adhesiveness.
〈従来の技術〉
有機ポリイソシアネート化合物が水と反応して炭酸ガス
を放出して尿素結合を形成することは既に知られている
。<Prior Art> It is already known that organic polyisocyanate compounds react with water to release carbon dioxide gas and form urea bonds.
有機ポリイソシアネートとポリヒドロキシル化合物から
、末端イソシアネートプレポリマーを作り、これを水ま
たは水蒸気と反応させて硬化させる方法は、例えば湿分
硬化型ウレタン系塗料や、湿分硬化型ウレタン系接着剤
として公知である。The method of making a terminal isocyanate prepolymer from an organic polyisocyanate and a polyhydroxyl compound and curing it by reacting with water or water vapor is known as, for example, a moisture-curing urethane paint or a moisture-curing urethane adhesive. It is.
また、有機ポリイソシアネートと親水性ポリヒドロキシ
ル化合物とにより、親水性の末端イソシアネートプレポ
リマーを作り、これを過剰の水と接触させて発泡硬化さ
せる方法も、例えばウレタン系グラウト剤として公知で
ある。Furthermore, a method in which a hydrophilic terminal isocyanate prepolymer is prepared from an organic polyisocyanate and a hydrophilic polyhydroxyl compound, and the prepolymer is brought into contact with excess water to foam and harden is also known, for example, as a urethane grouting agent.
さらに、有機ポリイソシアネートおよび／または有機ポ
リイソシアネートとポリヒドロキシル化合物より得られ
る末端イソシアネートプレポリマーと、水と必要ならば
界面活性剤およびウレタン化触媒を添加混合して反応さ
せて構造物を形成する方法も公知である。Furthermore, a method of forming a structure by adding and mixing an organic polyisocyanate and/or a terminal isocyanate prepolymer obtained from an organic polyisocyanate and a polyhydroxyl compound with water and a surfactant and a urethanization catalyst if necessary, and reacting the same. is also publicly known.
く本発明が解決しようとする問題点〉
これら公知の方法で製造される硬質フオームはいずれも
独立気泡を有するものが実用に供されている。ところが
例えば機能膜支持体やフィルター材のように硬度があり
かつ通気性を有するウレタンフオームが望まれているが
、従来の方法で連通気泡性を有する硬質フオームを製造
すると気泡が粗（、靭性や強度に劣り、魔性の大きい接
着性の弱いものしか得られない。Problems to be Solved by the Present Invention> All of the rigid foams produced by these known methods have closed cells and are in practical use. However, for example, urethane foams that are hard and breathable are desired for use in functional membrane supports and filter materials, but when producing rigid foams with open cell properties using conventional methods, the cells become coarse (and the toughness and It is inferior in strength and can only be obtained with weak adhesive properties that have great magical properties.
く本発明の目的〉
本発明は、このような従来の問題点を解決するためにな
されたもので、強度、靭性および接着性に優れた連通気
泡性を有する硬質のウレタンフオーム製造方法を提供す
ることを目的とする。OBJECTS OF THE INVENTION The present invention was made to solve these conventional problems, and provides a method for manufacturing a rigid urethane foam having open cell properties and excellent strength, toughness and adhesiveness. The purpose is to
く問題点を解決するための手段〉
本発明は２−ピロリドンの存在下において、有機ポリイ
ソシアネートおよび／または有機ポリイソシアネートと
ポリヒドロキシル化合物より得られる末端イソシアネー
トプレポリマーが、水あるいは水蒸気に接触すると直ち
に反応して硬化する事実を見出した事によってなされた
ものである。Means for Solving the Problems> The present invention provides a method for solving the above problems as soon as a terminal isocyanate prepolymer obtained from an organic polyisocyanate and/or an organic polyisocyanate and a polyhydroxyl compound comes into contact with water or water vapor in the presence of 2-pyrrolidone. This was achieved by discovering the fact that it hardens when it reacts.
ここで、２−ピロリドンは親水性の溶媒として作用する
だけでな（、有機イソシアネートと水との反応で強力な
触媒効果を発揮する。Here, 2-pyrrolidone not only acts as a hydrophilic solvent (but also exhibits a strong catalytic effect in the reaction between organic isocyanate and water).
さらに、ウレタンに良好な接着性を賦与する効果もある
。Furthermore, it has the effect of imparting good adhesion to urethane.
これら組成物を用いて連通気泡性を有する硬質ウレタン
フオームを製造するには次のような方法が考えられる。The following method can be considered for producing a rigid urethane foam having open-cell properties using these compositions.
すなわち、従来の方法によって製造された連通気泡性を
有する軟質ウレタンフオームにこの組成物を含浸し、圧
縮などの方法で余剰の組成物を除いた後に水あるいは水
蒸気を吹き付ける。That is, open-cell soft urethane foam produced by a conventional method is impregnated with this composition, excess composition is removed by a method such as compression, and then water or steam is sprayed onto the foam.
これによって軟質ウレタンフオームの内部気泡の骨格の
表面が発泡硬化し、ウレタンフオーム全体が硬質化する
。このとき、もとの軟質ウレタンフオームの有する連通
気泡性は保たれる。As a result, the surface of the skeleton of the internal cells of the soft urethane foam is foamed and hardened, and the entire urethane foam is hardened. At this time, the open cell properties of the original soft urethane foam are maintained.
さらに、連通気泡性硬質ウレタンフオームの硬度は含浸
液のイソシアネート化合物の種類やプレポリマーの構成
割合を変えることによって半硬質から硬質まで自在に調
整できる。Further, the hardness of the open-cell rigid urethane foam can be freely adjusted from semi-hard to hard by changing the type of isocyanate compound in the impregnating liquid and the composition ratio of the prepolymer.
く本発明の構成〉 く１）材料 本発明に使用する材料について説明する。Structure of the present invention> 1) Material The materials used in the present invention will be explained.
くイ〉軟質ウレタンフオーム
通気性を有し、また弾力性を有するフオームまたはマッ
ト状のものであれば何にでも応用することができるが、
最も適した基材としては連通気泡性軟質ウレタンフオー
ムであり、これは公知の方法で製造されるものである。〉Soft urethane foam It can be applied to any foam or mat-like material that has breathability and elasticity.
The most suitable substrate is an open-cell flexible urethane foam, which is manufactured by known methods.
く口〉含浸液の主材
本発明に使用できる含浸液主材としては、有機ポリイソ
シアネート、および／または有機ポリイソシアネートと
ポリヒドロキシル化合物より得られる末端イソシアネー
ト≠≠孝キマーがある。Main material of the impregnating liquid The main material of the impregnating liquid that can be used in the present invention includes an organic polyisocyanate and/or a terminal isocyanate obtained from an organic polyisocyanate and a polyhydroxyl compound.
プレポリ
例えば、有機ポリイソシアネートとしては、ＭＤＩ（メ
チレンジイソシアネート）、ＴＤＩ（トリレンジイソシ
アネート）、ＨＤＩ（ヘキサメチレンジイソシアネート
）、ＩＰＤＩ （イソホロンジイソシアネート）、ＸＤ
Ｉ（キシリレンジイソシアネート）などがあげられる。For example, organic polyisocyanates include MDI (methylene diisocyanate), TDI (tolylene diisocyanate), HDI (hexamethylene diisocyanate), IPDI (isophorone diisocyanate), XD
Examples include I (xylylene diisocyanate).
また、末端イソシアネートプレポリマーとしては、上記
有機イソシアネートにポリヒドロキシル化合物（ポリエ
ーテルポリオールなど）を反応させることによって得ら
れる。Further, the terminal isocyanate prepolymer can be obtained by reacting the above organic isocyanate with a polyhydroxyl compound (such as polyether polyol).
くハ〉触媒 本発明では、触媒としては２−ピロリドンを使用する。Kuha〉Catalyst In the present invention, 2-pyrrolidone is used as a catalyst.
２−ピロリドンは次のような特徴を備えている。すなわ
ち、親水性の溶剤としても作用し、イソシアネートと水
との反応によって生ずるウレア結合の触媒として作用し
、強固なポリウレア樹脂を形成する。2-pyrrolidone has the following characteristics. That is, it acts both as a hydrophilic solvent and as a catalyst for the urea bond produced by the reaction between isocyanate and water, forming a strong polyurea resin.
く二〉有機溶剤
本発明では、含浸液を低粘度化し、軟質ポリウレタンフ
ォーム内に容易に含浸が可能なように、例えばメチレン
クロライドのような溶剤を使用することもできる。含浸
液が低粘度であるか、または軟質ポリウレタンのセルが
粗い場合には、有機溶剤は使用する必要はない。2) Organic Solvent In the present invention, a solvent such as methylene chloride may be used to lower the viscosity of the impregnating liquid and enable easy impregnation into the flexible polyurethane foam. If the impregnating liquid has a low viscosity or the flexible polyurethane cells are coarse, it is not necessary to use an organic solvent.
（２）製造方法 本発明の製造方法を実施例を示して説明する。(2) Manufacturing method The manufacturing method of the present invention will be explained by showing examples.
上段の組成をもった含浸液を連通気泡性軟質ウレタンフ
オームに含浸させた後に圧縮等により余剰の含浸液を除
去した後、水あるいは水蒸気をふきつけて含浸液を硬化
させたところ、次に示すような特性を有する連通気泡性
の硬質ウレタンフオームが得られた。After impregnating the open-cell soft urethane foam with the impregnating liquid having the composition shown in the upper row, the excess impregnating liquid was removed by compression, etc., and the impregnating liquid was hardened by spraying with water or steam, as shown below. An open-cell rigid urethane foam with excellent properties was obtained.
〈実施例１〉
基材： 軟質ウレタンフオーム 比重０．０１８含浸液
：クルードＭＤＩ １００部メチレンクロライド３
０部
２−ピロリドン ７部
特性： 比重 ０．０８５
圧縮強度 ６．４ ｋｇ／ｃｄ
引張強度 ３．５ｂ／ｃｊ
基材に含浸液を含浸させて絞りロールで紋った後、水蒸
気を１０分間吹き付けて硬化させた。<Example 1> Base material: Soft urethane foam Specific gravity 0.018 Impregnation liquid: Crude MDI 100 parts Methylene chloride 3
0 parts 2-pyrrolidone 7 parts Characteristics: Specific gravity 0.085 Compressive strength 6.4 kg/cd Tensile strength 3.5b/cj After impregnating the base material with the impregnating liquid and squeezing it with a squeezing roll, water vapor was sprayed for 10 minutes. and cured.
〈実施例２〉
基材： 軟質ウレタンフオーム 比重０．０１８含浸液
：ＴＤＩプレポリマー １００部（グリセリンにプロ
ピレンオキシドおよびエチレンオキシドを付加重合させ
、分子量を４００に調整したポリエーテルにＴＤＩを反
応させて含有ＮＧＯを２０％に調整したプレポリマー）
２−ピロリドン ５部
特性： 比重 ０．０９
圧縮強度：２．５府／ｄ
実施例１と同じ条件で製造した。<Example 2> Base material: Soft urethane foam Specific gravity 0.018 Impregnating liquid: 100 parts of TDI prepolymer (contained by reacting TDI with polyether prepared by addition polymerizing propylene oxide and ethylene oxide to glycerin and adjusting the molecular weight to 400) Prepolymer with NGO adjusted to 20%) 2-pyrrolidone 5 parts Properties: Specific gravity 0.09 Compressive strength: 2.5 f/d Manufactured under the same conditions as Example 1.
〈実施例３〉
基材： 軟質ウレタンフオーム 比重０．０１８含浸液
、ＴＤＩプレポリマー １００部（グリセリンにプロ
ピレンオキシドおよびエチレンオキシドを付加重合させ
て
分子量を４８００に調整したポリエーテルにＴＤＩを反
応させて含有ＮＧＯを
２０％に調整したプレポリマー）
メチレンクロライド ３０部
２−ピロリドン ４部
特性： １０％圧縮強度 ０．７６ ｋｇ／ｃ＋Ｊ引
張強度 ２．７ ｋｇ ｃ＋７引張伸び
７０％
引裂強度 １．６２醋／ｄ
実施例１と同じ条件で製造した。<Example 3> Base material: Soft urethane foam Specific gravity 0.018 Impregnating liquid, 100 parts of TDI prepolymer (contained by reacting TDI with polyether prepared by addition polymerizing glycerin with propylene oxide and ethylene oxide to adjust the molecular weight to 4800) Prepolymer with NGO adjusted to 20%) Methylene chloride 30 parts 2-pyrrolidone 4 parts Properties: 10% compressive strength 0.76 kg/c+J tensile strength 2.7 kg c+7 tensile elongation
70% Tear strength 1.62/d Manufactured under the same conditions as Example 1.
以上の実施例によって得られた硬化物は連通気泡性を有
する硬質性のウレタンフオームで、靭性および強度に優
れたものであった。The cured product obtained in the above examples was a rigid urethane foam with open cell properties and was excellent in toughness and strength.
〈発明の効果〉
本発明は上記したようになるから下記のような効果を期
待することができる。<Effects of the Invention> Since the present invention is as described above, the following effects can be expected.
（１）硬質の連通気泡性を有するウレタンフオームが製
造可能で、実用に充分に耐え得る靭性と強度が得られる
ことから機能膜の支持体やフィルター等としての各分野
での広い用途が可能である。(1) It is possible to produce a hard, open-cell urethane foam that has enough toughness and strength to withstand practical use, so it can be used in a wide variety of fields, such as as a support for functional membranes and as filters. be.
（２）種々のプレポリマーの添加により半硬質から硬質
タイプの硬度を適宜調節できるので、その用途に応じて
最適の条件で使い分けることができる。(2) By adding various prepolymers, the hardness can be adjusted appropriately from semi-hard to hard type, so it can be used under optimal conditions depending on the application.
（３）接着性に優れているので、各種の基板等に良好に
接着することができる。(3) Since it has excellent adhesive properties, it can be well adhered to various substrates, etc.
Claims (1)
シアネートとポリヒドロキシル化合物より得られる末端
イソシアネートプレポリマーに、２−ピロリドンおよび
必要に応じ有機溶剤を混合した含浸液を連通気泡性軟質
ウレタンフォームに含浸し、水あるいは水蒸気に接触さ
せることによって製造する連通気泡性硬質ウレタンフォ
ームの製造方法。An open-cell flexible urethane foam is impregnated with an impregnating solution in which an organic polyisocyanate and/or a terminal isocyanate prepolymer obtained from an organic polyisocyanate and a polyhydroxyl compound is mixed with 2-pyrrolidone and an organic solvent if necessary. A method for producing open-cell rigid urethane foam by contacting it with water vapor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26197586A JPS63117045A (en) | 1986-11-05 | 1986-11-05 | Production of open-cell rigid urethane foam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26197586A JPS63117045A (en) | 1986-11-05 | 1986-11-05 | Production of open-cell rigid urethane foam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63117045A true JPS63117045A (en) | 1988-05-21 |
Family
ID=17369260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26197586A Pending JPS63117045A (en) | 1986-11-05 | 1986-11-05 | Production of open-cell rigid urethane foam |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63117045A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130184374A1 (en) * | 2012-01-13 | 2013-07-18 | Jeffrey S. Rich | Heat moldable gel and foam composition |
| EP3722731A4 (en) * | 2017-12-05 | 2021-09-01 | Toray Industries, Inc. | Sheet for heat exchange |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023133A (en) * | 1983-07-15 | 1985-02-05 | 本田技研工業株式会社 | Method of pasting tape on work surface with three-dimensional curved surface |
-
1986
- 1986-11-05 JP JP26197586A patent/JPS63117045A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023133A (en) * | 1983-07-15 | 1985-02-05 | 本田技研工業株式会社 | Method of pasting tape on work surface with three-dimensional curved surface |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130184374A1 (en) * | 2012-01-13 | 2013-07-18 | Jeffrey S. Rich | Heat moldable gel and foam composition |
| US9000059B2 (en) * | 2012-01-13 | 2015-04-07 | Masterfit Enterprises, Inc. | Heat moldable gel and foam composition |
| EP3722731A4 (en) * | 2017-12-05 | 2021-09-01 | Toray Industries, Inc. | Sheet for heat exchange |
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