JPH02166113A - Production of polyurethane elastomer - Google Patents
Production of polyurethane elastomerInfo
- Publication number
- JPH02166113A JPH02166113A JP63320390A JP32039088A JPH02166113A JP H02166113 A JPH02166113 A JP H02166113A JP 63320390 A JP63320390 A JP 63320390A JP 32039088 A JP32039088 A JP 32039088A JP H02166113 A JPH02166113 A JP H02166113A
- Authority
- JP
- Japan
- Prior art keywords
- component
- prepolymer
- groups
- polyurethane elastomer
- nco
- 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
- 229920003225 polyurethane elastomer Polymers 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 229920000768 polyamine Polymers 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920001228 polyisocyanate Polymers 0.000 claims abstract 4
- 239000005056 polyisocyanate Substances 0.000 claims abstract 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 229920005862 polyol Polymers 0.000 abstract description 5
- 150000003077 polyols Chemical class 0.000 abstract description 5
- 229920000909 polytetrahydrofuran Polymers 0.000 abstract description 5
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 4
- 229920000570 polyether Polymers 0.000 abstract description 4
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000009864 tensile test Methods 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-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 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- BSYVFGQQLJNJJG-UHFFFAOYSA-N 2-[2-(2-aminophenyl)sulfanylethylsulfanyl]aniline Chemical compound NC1=CC=CC=C1SCCSC1=CC=CC=C1N BSYVFGQQLJNJJG-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-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
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- -1 aliphatic glycols Chemical class 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はポリウレタンエラストマーの製造方法に関する
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing polyurethane elastomers.
ポリウレタンエラストマーは、耐摩耗性、機械強度、反
発弾性等に優れるため、製紙用ロール、製鉄用ロール、
ソリッドタイヤ等に広（使用されている。Polyurethane elastomers have excellent abrasion resistance, mechanical strength, impact resilience, etc., so they are used for paper manufacturing rolls, iron manufacturing rolls,
Widely used for solid tires, etc.
従来、ポリウレタンエラストマーの製造方法としては、
アジプレン（Ｕｎｉｒｏｙａｌ Ｃｈｅｍｉｃａ１社商
標）に代表されるトリレンジイソシアネートとポリエー
テルポリオールよりなるポリウレタンプレポリマーを芳
香族ポリアミンで硬化する方法およびプルコラン（Ｂａ
ｙｅｒ社商標）に代表されるナフチレンジイソシアネー
トとポリエステルポリオールよりなるポリウレタンプレ
ポリマーをグリコールで硬化させる方法が知られている
。Conventionally, the manufacturing method of polyurethane elastomer is as follows:
A method of curing a polyurethane prepolymer made of tolylene diisocyanate and polyether polyol, typified by adiprene (trademark of Uniroyal Chemica 1) with an aromatic polyamine, and
A method is known in which a polyurethane prepolymer made of naphthylene diisocyanate and polyester polyol, typified by Yer Co., Ltd. trademark), is cured with glycol.
ポリウレタンエラストマーは優れた耐摩耗性、機械強度
、反発弾性を有する反面、耐水性が悪い欠点を有する。Although polyurethane elastomers have excellent abrasion resistance, mechanical strength, and impact resilience, they have the disadvantage of poor water resistance.
この耐水性を改良する目的で、４．４′−ジフェニルメ
タンジイソシアネートとポリエーテルポリオールよりな
るポリウレタンプレポリマーをグリコールで硬化する方
法があるが、得られたポリウレタンエラストマーの耐久
性が悪く、満足な物性の製品とはいい難い。In order to improve this water resistance, there is a method of curing a polyurethane prepolymer made of 4,4'-diphenylmethane diisocyanate and polyether polyol with glycol, but the durability of the obtained polyurethane elastomer is poor and the physical properties are not satisfactory. It's hard to call it a product.
キシリレンジイソシアネートをポリウレタンエラストマ
ーに使用することは公知であるが、市販されているキシ
リレンジイソシアネートはｍ−キシリレンジイソシアネ
ートが主成分であり、得られたポリウレタンエラストマ
ーの機械強度が低い欠点を有する。Although it is known to use xylylene diisocyanate in polyurethane elastomers, commercially available xylylene diisocyanate is mainly composed of m-xylylene diisocyanate, and has the disadvantage that the mechanical strength of the obtained polyurethane elastomer is low.
本発明者らは鋭意研究した結果、ｐ−キシリレンジイソ
シアネートとポリヒドロキシ化合物とを反応せしめて得
た、分子末端にイソシアネート基を有するポリウレタン
プレポリマーを芳香族ポリアミンにより硬化することに
より製造したポリウレタンエラストマーは機械強度が優
れており、耐水性が大巾に向上することを見出し本発明
に到達した。As a result of intensive research, the present inventors found that a polyurethane elastomer was produced by curing a polyurethane prepolymer having an isocyanate group at the molecular end, which was obtained by reacting p-xylylene diisocyanate and a polyhydroxy compound, with an aromatic polyamine. The inventors have discovered that this material has excellent mechanical strength and greatly improves water resistance, and have arrived at the present invention.
本発明に使用するポリヒドロキシ化合物としては、水、
プロピレングリコール、グリセリン等にプロピレンオキ
サイド及び／又はエチレ：／オキサイドを付加したポリ
オキシアルキレンポリオール（分子量２００〜１０，０
００ ）、テトラヒドロフランを開環重合して得たポリ
テトラメチレンエーテルグリコール（分子量５００〜３
，０００ ）等のポリエーテルポリオールおよび公知の
各種ポリエステルポリオール、ポリブタジェンポリオー
ル、又、これらポリオール中でアクリロニトリル、スチ
レンの如きエチレン性不飽和化合物を重合したポリマー
ポリオール、ヒマシ油ポリオール等が使用できるが、そ
の中でもポリエーテルポリオールが特に好ましい。The polyhydroxy compound used in the present invention includes water,
Polyoxyalkylene polyol (molecular weight 200-10,0
00), polytetramethylene ether glycol obtained by ring-opening polymerization of tetrahydrofuran (molecular weight 500-3
. Among them, polyether polyols are particularly preferred.
この場合、分子量２００以下の脂肪族グリコールを併用
してもよい１分子量２００以下の脂肪族グリコールとし
ては、エチレングリコール、ジエチレングリコール、ト
リエチレングリコール、プロピレングリコール、ジプロ
ピレングリコール、トリプロピレングリコール、１．４
−ブタンジオール、１８３−ブタンジオール等が挙げら
れる。In this case, aliphatic glycols with a molecular weight of 200 or less that may be used in combination include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1.4
-butanediol, 183-butanediol, and the like.
本発明に使用する芳香族ポリアミンとしては、メチレン
ビス（０−クロロアニリン）（ＭＯＣＡ）、１．２−ビ
ス（２−アミノフェニルチオ）エタン（Ｃｙａ ｎ ａ
ｃ ｕ ｒ ｅ ： Ａｍｅｒｉｃａｎ Ｃｙａｎ
ａｍｉｄｅ社商標）、トリエチレングリコールージ（ｐ
−アミノベンゾエート） （Ｐ ｏ Ｉ ａ ｃ ｕ
ｒ ｅ ７４０ Ｍ ｒ Ｐｏｌａｒｏｉｄ社
商標）、３．５−ジメチルチオ−２，４−）ルエンジア
ミンと３，５−ジメチルチオ−２，６−）ルエンジアミ
ンの８０／ ２０重量％混合物（ＥＬｈａｃｕｒｅ３０
０ 二Ｅｔｈｙ１社商標）等が使用できる。Aromatic polyamines used in the present invention include methylenebis(0-chloroaniline) (MOCA), 1,2-bis(2-aminophenylthio)ethane (Cyan a
cu r e: American Cyan
amide company trademark), triethylene glycoluge (p
-aminobenzoate) (P o I a cu
r e 740 Mr Polaroid Co., Ltd.), an 80/20 wt% mixture of 3,5-dimethylthio-2,4-)luenediamine and 3,5-dimethylthio-2,6-)luenediamine (ELhacure30
02Ethy1 company trademark) etc. can be used.
上記ポリヒドロキシ化合物とｐ−キシリレンジイソシア
ネートとを反応せしめて得た、分子末端にインシアネー
ト基を有するポリウレタンプレポリマーを上記芳香族ポ
リアミンにより硬化してポリウレタンエラストマーを製
造する。A polyurethane prepolymer having an incyanate group at the molecular end, obtained by reacting the above polyhydroxy compound with p-xylylene diisocyanate, is cured with the above aromatic polyamine to produce a polyurethane elastomer.
この場合、ｐ−キシリレンジイソシアネートとポリヒド
ロキシ化合物のＮＣ０１０Ｈ（モル比）＝１．５゜／ｌ
〜２．５／ Ｌ 、又、ポリウレタンプレポリマーと上
記芳香族ポリアミンのＮＣＯ／ＮＨｚ （モル比）＝
０．９／１〜１．３／１である。In this case, NC010H (molar ratio) of p-xylylene diisocyanate and polyhydroxy compound = 1.5°/l
~2.5/L, and NCO/NHz (mole ratio) of the polyurethane prepolymer and the above aromatic polyamine =
It is 0.9/1 to 1.3/1.
以下に、合成例、実施例及び比較例を挙げて、本発明を
具体的に説明する。The present invention will be specifically explained below with reference to Synthesis Examples, Examples, and Comparative Examples.
本実施例及び比較例において引張試験は、ＪＩＳＫ ６
３０１に準拠して実施した。In the present examples and comparative examples, the tensile test was conducted using JISK 6
It was carried out in accordance with 301.
初期物性−−−−１００℃で２４時間硬化後、２３°Ｃ
で５５％の相対湿度の恒温室に７日間熟成後測定した。Initial physical properties: 23°C after curing at 100°C for 24 hours
After aging for 7 days in a constant temperature room with a relative humidity of 55%, measurements were taken.
耐水性−一一一一−・−・−８０°Ｃの温水に１４日間
浸漬後、２３゛Ｃで５５％の相対湿度の恒温室に７日間
熟成後測定した。Water Resistance - 1111--It was measured after being immersed in warm water at -80°C for 14 days and aged in a constant temperature room at 23°C and 55% relative humidity for 7 days.
合成例 １
ｐ−キシリレンジイソシアネート１８８ｇ （２当盟）
をポリテトラメチレンエーテルグリコール５００ｇ （
ｌ当Ｍ）と １００″Ｃで６時間反応させ、末端ＮＧＯ
５を６．０重量％含有するプレポリマーを得た。Synthesis example 1 p-xylylene diisocyanate 188g (2 units)
500g of polytetramethylene ether glycol (
1M) at 100"C for 6 hours to form
A prepolymer containing 6.0% by weight of 5 was obtained.
合成例 ２
２．４− ）リレンジイソシアネー）１７４ｇ（２当量
）をポリテトラメチレンエーテルグリコール５００ｇ
（１当量）と８０°Ｃで４時間反応させ、末端ＮＣＯ基
を６．３重量％含有するプレポリマーを得た。Synthesis Example 2 174 g (2 equivalents) of 2.4-) lylene diisocyanate was added to 500 g of polytetramethylene ether glycol.
(1 equivalent) at 80° C. for 4 hours to obtain a prepolymer containing 6.3% by weight of terminal NCO groups.
合成例 ３
ｍ−キシリレンジイソシアネート１８８ｇ （２当量）
をポリテトラメチレンエーテルグリコール５００ｇ （
１当量）と１００℃で６時間反応させ、末端ＮＧＯ基を
６．０重量％含有するプレポリマーを得た。Synthesis example 3 m-xylylene diisocyanate 188g (2 equivalents)
500g of polytetramethylene ether glycol (
1 equivalent) at 100° C. for 6 hours to obtain a prepolymer containing 6.0% by weight of terminal NGO groups.
実施例 １
合成例 １で得たプレポリマー１００ｇを１００℃に加
熱し、真空デシケータ−中で減圧脱泡後、１２０℃で溶
解したメチレンビス（Ｏ−クロロアニリン）（ＭＯＣＡ
）１７ｇと泡を巻き込まないように均一に攪拌して、１
００℃で予備加熱したモールドに流し込み１００℃で２
４時間硬化した。この場合、プレポリマーとメチレンビ
ス（０−クロロアニリン）におけるＮＣＯ／Ｎｕ！
（モル比）＝１．１となる様にした。Example 1 100 g of the prepolymer obtained in Synthesis Example 1 was heated to 100°C, degassed under reduced pressure in a vacuum desiccator, and then methylenebis(O-chloroaniline) (MOCA) dissolved at 120°C was heated.
) 17g and stir evenly to prevent bubbles from getting mixed in.
Pour into a mold preheated at 00℃ and heat at 100℃ for 2 hours.
It was cured for 4 hours. In this case, NCO/Nu! in the prepolymer and methylenebis(0-chloroaniline)!
(molar ratio)=1.1.
上記組成物の引張試験を行なった結果、表−１に示すご
と（良好な耐水性を有することが認められた。As a result of performing a tensile test on the above composition, as shown in Table 1 (it was recognized that it had good water resistance).
実施例 ２
合成例 １で得たプレポリマーｔ００ｇを１００℃に加
熱し、真空デシケータ−中で減圧脱泡後、ジメチルチオ
トルエンジアミン（Ｅｔｈａｃｕｒｅ ３０００４ｇ
と泡を巻き込まないように均一に攪拌して、１００℃で
予備加熱したモールドに流し込み１００℃で２４時間硬
化した。この場合、プレポリマフンジメチルチオトルエ
ンジアミンにおけるＮＧＯ／ ＮＨ！（モル比）−１，
１となる樺にした。Example 2 t00g of the prepolymer obtained in Synthesis Example 1 was heated to 100°C, degassed under reduced pressure in a vacuum desiccator, and dimethylthiotoluenediamine (Ethacure 30004g) was heated to 100°C.
The mixture was stirred uniformly to avoid entraining bubbles, poured into a mold preheated at 100°C, and cured at 100°C for 24 hours. In this case, NGO/NH! in prepolymer dimethylthiotoluenediamine! (molar ratio) -1,
I chose birch, which will be number 1.
上記（酸物の引張試験を行なった結果、表＝１に示すご
とく良好な耐水性を有することが認められた。As a result of carrying out the tensile test with the acid mentioned above, it was found that it had good water resistance as shown in Table 1.
比較例 １
合成例 ２で得たプレポリマー１００ｇとＭＯＣＡ１８
ｇを実施例 １と同様な操作で硬化した。Comparative Example 1 100g of prepolymer obtained in Synthesis Example 2 and MOCA18
g was cured in the same manner as in Example 1.
試験結果は表−１に示すように耐水性が悪かった。As shown in Table 1, the test results showed poor water resistance.
比較例 ２
合成例 ３で得たプレポリマー１００ｇとＭＯＣＡ１７
ｇを実施例 １と同様な操作で硬化した。Comparative Example 2 100g of prepolymer obtained in Synthesis Example 3 and MOCA17
g was cured in the same manner as in Example 1.
試験結果は表−１に示すように耐水性の保持率は良いが
、初期物性の強度が低かった。As shown in Table 1, the test results showed that the water resistance retention rate was good, but the strength of the initial physical properties was low.
表−１硬化試験結果
実施例工
〈初期物性〉
１００％モジュラス［Ｋｇ／ｃｍ”１
３００％モジュラス［Ｋｇ／ｃｓ”ｌ
破断時強度［Ｋｇ／ｃａ”１
伸び（％）
引裂強度［Ｋａ／ｃｍ ］
実施例２
比較例！
比較例２
（耐水性〉
１００％モジュラス（にｇ／ｃｔａ町
３００％モジュラス［Ｋｇ／ｃｏ＋”ｌ破断時強度［Ｋ
ｇ／ｃｍ”ｌ
伸び（％）
引裂強度ＩＫｇ／ｃ麟１
〔発明の効果〕
本発明により、従来品に比して硬化物の機械強度の低下
がなく、耐水性が著しく向上したポリウレタンエラスト
マーを製造することができる。Table-1 Curing test results Examples (Initial physical properties) 100% modulus [Kg/cm"1 300% modulus [Kg/cs"l Strength at break [Kg/ca"1 Elongation (%) Tear strength [Ka/cm] ] Example 2 Comparative example! Comparative example 2 (Water resistance) 100% modulus (g/cta town 300% modulus [Kg/co+"l strength at break [K
g/cm"l Elongation (%) Tear strength IKg/crin1 [Effects of the invention] The present invention has produced a polyurethane elastomer that does not reduce the mechanical strength of the cured product and has significantly improved water resistance compared to conventional products. can be manufactured.
Claims (1)
とを反応せしめて得た、分子末端にイソシアネート基を
有するポリウレタンプレポリマーを芳香族ポリアミンに
より硬化してポリウレタンエラストマーを製造する方法
において、 該有機ポリイソシアネートが、ｐ−キシリレンジイソシ
アネートであることを特徴とするポリウレタンエラスト
マーの製造方法。(1) A method for producing a polyurethane elastomer by curing with an aromatic polyamine a polyurethane prepolymer having an isocyanate group at the molecular end obtained by reacting an organic polyisocyanate and a polyhydroxy compound, wherein the organic polyisocyanate is A method for producing a polyurethane elastomer, characterized in that it is p-xylylene diisocyanate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63320390A JPH02166113A (en) | 1988-12-21 | 1988-12-21 | Production of polyurethane elastomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63320390A JPH02166113A (en) | 1988-12-21 | 1988-12-21 | Production of polyurethane elastomer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02166113A true JPH02166113A (en) | 1990-06-26 |
Family
ID=18120935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63320390A Pending JPH02166113A (en) | 1988-12-21 | 1988-12-21 | Production of polyurethane elastomer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02166113A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2873091B2 (en) * | 1992-04-10 | 1999-03-24 | ユニロイヤル ケミカル カンパニー インコーポレイテッド | Polyurethane elastomer and airless tire made therefrom |
| CN1070876C (en) * | 1997-07-30 | 2001-09-12 | 长岛县聚氨酯制品厂 | Polyurethane used for car engine front and rear suspension soft pad assembly |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4948789A (en) * | 1972-05-04 | 1974-05-11 | ||
| JPS51106197A (en) * | 1975-03-14 | 1976-09-20 | Bridgestone Tire Co Ltd | |
| JPS562348A (en) * | 1979-06-20 | 1981-01-12 | Nippon Polyurethan Kogyo Kk | Elastomer composition for printing roller |
| JPS5811523A (en) * | 1981-07-13 | 1983-01-22 | Mitsubishi Gas Chem Co Inc | Polyurethane composition |
-
1988
- 1988-12-21 JP JP63320390A patent/JPH02166113A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4948789A (en) * | 1972-05-04 | 1974-05-11 | ||
| JPS51106197A (en) * | 1975-03-14 | 1976-09-20 | Bridgestone Tire Co Ltd | |
| JPS562348A (en) * | 1979-06-20 | 1981-01-12 | Nippon Polyurethan Kogyo Kk | Elastomer composition for printing roller |
| JPS5811523A (en) * | 1981-07-13 | 1983-01-22 | Mitsubishi Gas Chem Co Inc | Polyurethane composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2873091B2 (en) * | 1992-04-10 | 1999-03-24 | ユニロイヤル ケミカル カンパニー インコーポレイテッド | Polyurethane elastomer and airless tire made therefrom |
| CN1070876C (en) * | 1997-07-30 | 2001-09-12 | 长岛县聚氨酯制品厂 | Polyurethane used for car engine front and rear suspension soft pad assembly |
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