JPH0496919A - Production of room temperature curable urethane elastomer - Google Patents
Production of room temperature curable urethane elastomerInfo
- Publication number
- JPH0496919A JPH0496919A JP2212192A JP21219290A JPH0496919A JP H0496919 A JPH0496919 A JP H0496919A JP 2212192 A JP2212192 A JP 2212192A JP 21219290 A JP21219290 A JP 21219290A JP H0496919 A JPH0496919 A JP H0496919A
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate
- compound
- elastomer
- room temperature
- urethane elastomer
- 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
- 229920006311 Urethane elastomer Polymers 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 hydrogen compound Chemical class 0.000 claims abstract description 38
- 239000012948 isocyanate Substances 0.000 claims abstract description 35
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 17
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims abstract description 12
- 150000003077 polyols Chemical class 0.000 claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 abstract description 8
- 230000000704 physical effect Effects 0.000 abstract description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract description 3
- 229920001971 elastomer Polymers 0.000 abstract description 3
- 239000000806 elastomer Substances 0.000 abstract description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004078 waterproofing Methods 0.000 abstract description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- BDPMIHVEHJUJIW-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanediamine Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(N)(N)C1=CC=CC=C1 BDPMIHVEHJUJIW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241001112258 Moca Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 230000000739 chaotic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 210000004709 eyebrow Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
〔産業上の利用分野〕
本発明は、塗膜防水材、塗膜床材用として利用される常
温硬化性のウレタンエラストマー、より詳しくは、上記
目的に適った、改良された硬化性、物性及び作業性を備
える常温硬化性ウレタンエラストマーの製造法に関する
ものである。
〔従来の技術〕
塗膜防水材、塗膜床材に用いられる従来の常温硬化性の
ウレタンエラストマーとしては、例えばイソシアネート
化合物としてトリレンジイソシアネートとポリエーテル
ポリオールとを反応させた末端イソシアネート基含有ウ
レタンプレポリマーが用いられ、活性水素化合物として
ジクロロジアミノジフェニルメタンをポリエーテルポリ
オールに溶解したものが用いられる。
これらの２液温合タイプのウレタンエラストマーは、仕
上り性もよく、引張強度、伸び、耐摩耗性、耐薬品性、
耐候性などに優れた特性を有するので１これらの特性を
生かして床、廊下、屋上、ベランダ等の床材、防水材と
して広く用いられている。
しかしながら、このような従来の２液混合タイプの常温
硬化性ウレタンエラストマーでは、２液温合後１塗装面
が歩行可能な程度にまで硬化するのに半日（１２時間）
から１日（２４時間）もの長時間を必要とするため、補
修等に際し、硬化完了までの間、通行止めの不自由を忍
ばねばならない。
従って、この硬化速度性を速くすることができれば大き
な経済効果を期待できる筈である。
ところで、一般に硬化速度を速くする方法としては触媒
量を多くすることが考えられるが、触媒は重合触媒とし
て働くと同時に、また分解触媒としても作用するため、
触媒の増量は、反面、得られたウレタンエラストマーの
劣化を促進するという欠点を派生する。
別に、硬化速度を速めるための方法として、反応性の高
いイソシアネート類を用いる方法もあるが、そうすると
、２液温合後の増粘速度も速くなるため可使時間が短く
なり、作業性が低下するという不利益を生じる。
〔発明が解決しようとする課題〕
本発明は、公知の常温硬化性ウレタンエラストマーにお
ける上記問題点を解決し、触媒の増量や易反応性のイソ
シアネートの専用などといった常識的な方法によること
なしに、改良された硬化性、物性及び作業性を備える常
温硬化性の新規ウレタンエラストマーを提供するのを目
的とする。[Industrial Field of Application] The present invention relates to a room-temperature curable urethane elastomer used as a waterproof coating material or a coating floor material, and more specifically, a urethane elastomer that is curable at room temperature and has improved curability, physical properties, and is suitable for the above-mentioned purposes. The present invention relates to a method for producing a room temperature curable urethane elastomer with workability. [Prior Art] Conventional room temperature curable urethane elastomers used for waterproof coating materials and floor coating materials include, for example, urethane preforms containing terminal isocyanate groups, which are made by reacting tolylene diisocyanate and polyether polyol as isocyanate compounds. A polymer is used, and dichlorodiaminodiphenylmethane dissolved in polyether polyol is used as the active hydrogen compound. These two-component heating type urethane elastomers have good finish, tensile strength, elongation, abrasion resistance, chemical resistance,
Because it has excellent properties such as weather resistance, it is widely used as flooring and waterproofing materials for floors, hallways, rooftops, balconies, etc., taking advantage of these properties. However, with conventional two-component mixing type room-temperature-curing urethane elastomers, it takes half a day (12 hours) for one coated surface to cure to a walkable level after the two components are heated.
Because it takes a long time (24 hours) for repairs, etc., people have to endure the inconvenience of road closures until the cure is complete. Therefore, if the curing speed can be increased, a great economic effect can be expected. By the way, one way to increase the curing speed is generally to increase the amount of catalyst, but since the catalyst acts as a polymerization catalyst and also as a decomposition catalyst,
On the other hand, increasing the amount of catalyst has the disadvantage of accelerating the deterioration of the obtained urethane elastomer. Separately, there is a method of using highly reactive isocyanates to speed up the curing speed, but this also increases the rate of viscosity increase after heating the two liquids, shortening the pot life and reducing workability. There will be a disadvantage of doing so. [Problems to be Solved by the Invention] The present invention solves the above-mentioned problems in known room-temperature curable urethane elastomers, without resorting to common-sense methods such as increasing the amount of catalyst or dedicating highly reactive isocyanate. The purpose of the present invention is to provide a new room-temperature curable urethane elastomer having improved curability, physical properties, and workability.
〔課題を解決するための手段〕
（１）概要
以上の目的を達成するため、本発明に係る常温硬化性ウ
レタンエラストマーの製造法は、イソシアネート化合物
と活性水素化合物とを反応、硬化させて、常温硬化性の
ウレタンエラストマーを製造するに当たり、イソシアネ
ート化合物として芳香族ポリイソシアネートとポリオー
ルとを予め反応させて得られる末端イソシアネート基含
有ウレタンプレポリマー１０Ｏｌ置部に脂肪族ポリイソ
シアネートを１〜１５重量部配合したイソシアネート混
合物を用いることを特徴とする。
以下、発明の構成要素等に関する事項につき項分けして
説明する。
（２）末端イソシアネート基含有ウレタンプレポリマー
及びインシアネー）Ｒ合物
本発明のイソシアネート化合物として使用するイソシア
ネートｇ合物において、一方の成分である末端イソシア
ネート基含有ウレタンプレポリマーは、前記の如く芳香
族ポリイソシアネートとポリオールを反応させることに
よって得られる。
ここに芳香族ポリイソシアネートとしては、トリレンジ
イソシアネート（ＴＤＩ、 ＴＤＩ−１００，７ＤＩ−
８０７ＤＩ−８５） 、ジフェニルメタンジイソシアネ
ート（８０１） 、液状Ｍ０１ 、ボＵＪ’）ツクＭｒ
ＪＩ等が挙ｌｆうれ、特にＭＤＩ 、液状ＭＤＩが好ま
しい。
またポリオールとしては、多価アルコール、例えば、プ
ロピレングリコール、グリセリン等のポリヒドロキシ化
合物にエチレンオキサイド、プロピレンオキサイド等の
フルキレンオキサイドを付加したポリエーテルポリオー
ル、ポリテトラメチレンエーテルグリコール、ポリエス
テルポリオール等が挙げられる。
末端イソシアネート基含有ウレタンプレポリマー中の遊
離イソシアネート基は、２〜ｌＯ％、好ましくは３〜８
％の範囲である。２％以下では粘度が高くなり、】０％
以上では空気中の湿気の影響ヲ受ケ易くなって生成ウレ
タンエラストマー表面の仕上り性が悪くなる。
前記末端イソシアネート基含有ウレタンプレポリマーに
配合されるもう一方の成分、すなわち脂肪族ポリイソシ
アネートとしては、脂環式ポリイソシアネートを含むも
のであって、例えばヘキサメチレンジイソシアネート、
及びそのビューレット変性体、ヘキサメチレンジイソシ
アネートのヌレート変性体、水素化ＭＤ１．インホロン
ジイソシアネート、水素化キシリレンジイソシアネート
中訓か等が挙げられ、特に水素化にＤｌ及びインホロン
ジイソシアネートが好ましい。
イソシアネート混合物における脂肪族ポリイソシアネー
トの配合量は、末端イソシアネート基含有ウレタンプレ
ポリマー１００重量部に対し１〜１５重量部である。脂
肪族ポリイソシアネートの配合量が１重量部以下では効
果なく、また１５重量部以」二では、ウレタンエラスト
マーの仕上り性が悪くなると共に、ウレタンエラストマ
ーの弾性がなくなるため好ましくない。
（３）活性水素化合物
イソシアネート化合物と反応せしめられる活性水素化合
物としては、ジクロロジアミノジフェニルメタン（ＭＯ
ＣＡ）、ＭＯＣ：Ａの多核体、ジアミノフェニルメタン
（［ｌＡＭ） 、 ジエチルトルエンジアミン（ＤＥＴ
ＯＡ）等のアミン化合物やポリエーテルポリオール、ポ
リエステルポリオール等のポリオール等が挙げられ、殊
にＭＯＣＡ又はＭＯＣＡの多核体をポリエーテルポリオ
ールに溶解させたものが好ましい。
尚、活性水素化合物として使用するアミン化合物は、末
端イソシアネート基含有ウレタンプレポリマーの！離イ
ソシアネート基に対し当量以上となる量である。
（４）他の補助剤
本発明のウレタンエラストマーの製造においては、必要
に応じて公知の触媒、充填剤、可塑剤、溶剤、消泡剤１
着色剤等が補助的に配合してもよ１、％。
〔作用〕
一般に、イソシアネート化合物と活性水素化合物を当量
で反応させると、硬化途中で空気中や材料中の水分もイ
ソシアネートと≠反応する（即ち、空気中や材料中の水
分も活性水素化合物とし−て作用する）ため、活性水素
化合物が過剰となって未反応物がウレタンエラストマー
中に残り、引張強度、伸び、引裂き強度などの物性低下
を起こすと共に、変色など耐候性が悪くなる。このため
、イソシアネート化合物が多少過剰に配合されている。
一方、反応を速く、つまり硬化を速くするためには、活
性水素化合物、特に−級アミン基や二級アミン基を持つ
アミン化合物を当量又は当量以上に使用するのが好まし
いが、そうすると、前記したように活性水素化合物が過
剰になり、硬化したウレタンエラストマーの物性や耐候
性の低下を引き起す。
しかるに本発明では、反応性の高い芳香族イソシアネー
トｔ−用いたプレポリマーに、反応性の低い脂肪族イソ
シアネートを配合することによって、反応性の高い芳香
族イソシアネートを用いたプレポリマーとの反応に際し
て残った過剰の（未反応の）活性水素化合物（アミン化
合物、ポリオール）を反応性の低い脂肪族イソシアネー
トが捕捉するため、物性低下や変色が起こらず、しかも
塗布面が歩行可能になるまでの初期硬化強度は、反応性
の高い芳香族イソシアネートを用いたプレポリマーとア
ミン化合物の反応にて得られる。しかも２液温合時に、
反応性の低い脂肪族イソシアネートが、可塑剤や溶剤の
ように作用して低粘度化に寄与する結果、増粘が抑制さ
れて長い可使時間が得られる。
〔実施例〕
以下、実施例及び比較例により発明具体化の例及び効果
につき述べるが、例示は単に説明用のもので１発明思想
の駆足を意図したものではない。
実施例１〜３、比較例１〜２
（１）末端イソシアネート基含有ウレタンプレポリマー
の製造
（Ａ）平均分子量５０００のポリオキシプロピレントリ
オール４０４ｇと、
平均分子量２０００のポリオキシプロピレングリコール
２０２ｇと、
平均分子量２００のポリオキシプロピレングリコール８
８ｇとを夫々計量、混合し、これに、Ｍｏｌ （ミリ
オネートＭＴ、日本ポリウレタン■社製品） ３２８
ｇを添加して８０’Ｏで５時間撹拌しながら反応させた
後、キシレン１１５ｇで稀釈し、ＦＮＣ８５，５％、粘
度６０００ｃｐｓ／ ２５℃の末端イソシアネート基含
有ウレタンプレポリマー（以下、プレポリマーＡという
）を得た。
（Ｂ）平均分子量５０００のポリオキシプロピレントリ
オール４４９ｇと、
平均分子量２０００のポリオキシプロピレングリコール
２２５ｇと、
平均分子量２００のポリオキシプロピレングリコール７
５ｇを夫々計量、混合し、これに、ＭＤＩ−＃２５１
ｇを添加、８０°ｃで５時間撹拌しながら反応させた後
、キシレン５３ｇで稀釈し、ｈｃ８６．５％、粘度５５
００ｃｐｓ／ ２５℃の末端イソシアネート基含有ウレ
タンプレポリマー（以下、プレポリマーＢという）を得
た。
（２）イソシアネート混合物の製造
（＾）前記プレポリマーＡ １００重量部に対し、水素
化ＭＤＩ７３１（像部を配合し、 ＦＮＣＯ７，２％、
粘度４５００ｃｐｓ／２５℃のイソシアネート混合物（
以下、イソシアネート混合物Ａという）を得た。
（Ｂ）前記プレポリマーＡ１００重量部に対し、インホ
ロンジイソシアネート７重量部を配合し、Ｆｓｃｏ ７
．６％、粘度４５００ ｃｐｓ／２５℃のイソシアネー
ト混合物（以下、イソシアネート混合物Ｂという）を得
た。
（Ｃ）前記プレポリマーＢ１００重量部に対し、インホ
ロンジイソシアネート７重量部を配合し、ＦＮＣｏ ８
．５％、粘度４０００ｃｐｓ／２５℃のイソシアネート
混合物（以下、イソシアネートａ合物Ｃという）を得た
。
（３）ウレタンエラストマーの製造
上記のプレポリマーＡ−Ｂ及びイソシアネート混合物Ａ
−Ｃを用い、下表−１の配合に従って、主剤／硬化剤＝
１００／１００の重量比で反応させることにより、厚
さ２ＩＩｏｌのウレタンエラストマーシートを作成した
。結果を下表−２に示す。
（以下余白）
表−１
表−２
イハラケミカルエズ湘Ｊ３暑を粘兄 船」の多俵体：ア
ミン価２１０ Ｉ１ｇＫＯ！（／ｇプレポリブーのｍ刀
に対するアミンの酋量比全ｍ−刀に対するアミンの当量
比
新日埠Ｊ里イレ朱式論４封貼ｎ
日東皇Ｈ上ふ Ｎ５Ｉ１１００
日本化学産業５ｄし暑七粘易 ニー／カオクチック鉛２
０％日本二二カ株式会社製品 シリコーンオイルＦＺ５
８２５［１月
■）主剤、硬化鞍合後、Ｂ型粘度計で６ＸＩＱ’ ｃｐ
ｓに達するまでのｌＩ眉１ル２）スリッパで歩いても足
跡が殆ど残らなくなるまでの−１１１゜３） ＪＩＳ
Ａ３０２１ に準拠して測定。
４）ウェザオフ−ター６０田冊１処理。
■下余白）[Means for Solving the Problems] (1) Overview In order to achieve the above objects, the method for producing a room temperature curable urethane elastomer according to the present invention involves reacting and curing an isocyanate compound and an active hydrogen compound, In producing a curable urethane elastomer, 1 to 15 parts by weight of an aliphatic polyisocyanate was blended into 100 liters of a urethane prepolymer containing terminal isocyanate groups obtained by reacting an aromatic polyisocyanate and a polyol in advance as an isocyanate compound. It is characterized by the use of an isocyanate mixture. Hereinafter, matters related to the constituent elements of the invention will be explained in sections. (2) Urethane prepolymer containing terminal isocyanate group and incyane) R compound In the isocyanate compound used as the isocyanate compound of the present invention, one component, the urethane prepolymer containing terminal isocyanate group, is an aromatic polymer as described above. Obtained by reacting isocyanate and polyol. Here, as the aromatic polyisocyanate, tolylene diisocyanate (TDI, TDI-100, 7DI-
807DI-85), diphenylmethane diisocyanate (801), liquid M01, BoUJ') Tsuku Mr.
Examples include JI and the like, and MDI and liquid MDI are particularly preferred. Examples of polyols include polyhydric alcohols such as polyether polyols, polytetramethylene ether glycols, polyester polyols, etc. in which fullylene oxides such as ethylene oxide and propylene oxide are added to polyhydric alcohols, such as polyhydroxy compounds such as propylene glycol and glycerin. . The free isocyanate groups in the urethane prepolymer containing terminal isocyanate groups are 2 to 10%, preferably 3 to 8%.
% range. If it is less than 2%, the viscosity will be high, and ]0%
If this is the case, the urethane elastomer will be susceptible to the effects of moisture in the air, resulting in poor surface finish of the urethane elastomer. The other component blended into the terminal isocyanate group-containing urethane prepolymer, that is, the aliphatic polyisocyanate, includes an alicyclic polyisocyanate, such as hexamethylene diisocyanate,
and its biuret modified product, nurate modified product of hexamethylene diisocyanate, hydrogenated MD1. Examples include inphorone diisocyanate and hydrogenated xylylene diisocyanate, with Dl and inphorone diisocyanate being particularly preferred for hydrogenation. The amount of aliphatic polyisocyanate in the isocyanate mixture is 1 to 15 parts by weight per 100 parts by weight of the urethane prepolymer containing terminal isocyanate groups. If the amount of the aliphatic polyisocyanate is less than 1 part by weight, it will not be effective, and if it is more than 15 parts by weight, the finishing properties of the urethane elastomer will deteriorate and the urethane elastomer will lose its elasticity, which is not preferable. (3) Active hydrogen compound The active hydrogen compound to be reacted with the isocyanate compound is dichlorodiaminodiphenylmethane (MO
CA), MOC: A polynuclear substance, diaminophenylmethane ([lAM), diethyltoluenediamine (DET
Examples include amine compounds such as OA) and polyols such as polyether polyols and polyester polyols, and particularly preferred are MOCA or polynuclear bodies of MOCA dissolved in polyether polyols. The amine compound used as the active hydrogen compound is a urethane prepolymer containing terminal isocyanate groups! The amount is equivalent to or more than the free isocyanate group. (4) Other auxiliary agents In the production of the urethane elastomer of the present invention, known catalysts, fillers, plasticizers, solvents, antifoaming agents, etc.
A coloring agent or the like may be added 1.%. [Function] Generally, when an isocyanate compound and an active hydrogen compound are reacted in equivalent amounts, moisture in the air or in the material also reacts with the isocyanate during curing (that is, moisture in the air or in the material also becomes an active hydrogen compound). As a result, the active hydrogen compound becomes excessive and unreacted substances remain in the urethane elastomer, causing a decrease in physical properties such as tensile strength, elongation, and tear strength, as well as poor weather resistance such as discoloration. For this reason, the isocyanate compound is blended in a somewhat excessive amount. On the other hand, in order to speed up the reaction, that is, to speed up curing, it is preferable to use an equivalent amount or more of an active hydrogen compound, especially an amine compound having a -class amine group or a secondary amine group. As a result, the active hydrogen compound becomes excessive, causing a decrease in the physical properties and weather resistance of the cured urethane elastomer. However, in the present invention, by blending a less reactive aliphatic isocyanate into a prepolymer using a highly reactive aromatic isocyanate, no residue remains during the reaction with a prepolymer using a highly reactive aromatic isocyanate. Since the aliphatic isocyanate with low reactivity captures excess (unreacted) active hydrogen compounds (amine compounds, polyols), there is no deterioration of physical properties or discoloration, and the initial curing is possible until the coated surface becomes walkable. Strength is obtained by reacting a prepolymer with a highly reactive aromatic isocyanate and an amine compound. Moreover, when the two liquids warm up,
The aliphatic isocyanate with low reactivity acts like a plasticizer or a solvent and contributes to lowering the viscosity, thereby suppressing thickening and providing a long pot life. [Examples] Examples and effects of embodying the invention will be described below using Examples and Comparative Examples, but the examples are merely for explanation and are not intended to drive the idea of the invention. Examples 1 to 3, Comparative Examples 1 to 2 (1) Production of urethane prepolymer containing terminal isocyanate groups (A) 404 g of polyoxypropylene triol with an average molecular weight of 5000, 202 g of polyoxypropylene glycol with an average molecular weight of 2000, average molecular weight 200 polyoxypropylene glycol 8
Weigh and mix 8 g of each, and add Mol (Millionate MT, a product of Nippon Polyurethane Company) 328.
After reacting with stirring at 80'O for 5 hours, it was diluted with 115 g of xylene, and a urethane prepolymer containing terminal isocyanate groups (hereinafter referred to as prepolymer A) with FNC of 85.5% and viscosity of 6000 cps/25°C was added. ) was obtained. (B) 449 g of polyoxypropylene triol with an average molecular weight of 5000, 225 g of polyoxypropylene glycol with an average molecular weight of 2000, and polyoxypropylene glycol 7 with an average molecular weight of 200.
Weigh and mix 5g of each, add MDI-#251 to this
After reacting with stirring at 80°C for 5 hours, diluted with 53g of xylene, hc 86.5%, viscosity 55
A urethane prepolymer containing terminal isocyanate groups (hereinafter referred to as prepolymer B) was obtained at a temperature of 00 cps/25°C. (2) Production of isocyanate mixture (^) To 100 parts by weight of the prepolymer A, hydrogenated MDI 731 (image area) was blended, FNCO 7.2%,
Isocyanate mixture with a viscosity of 4500 cps/25°C (
Hereinafter referred to as isocyanate mixture A) was obtained. (B) 7 parts by weight of inphorone diisocyanate is blended with 100 parts by weight of the prepolymer A, and Fsco 7
．． An isocyanate mixture (hereinafter referred to as isocyanate mixture B) with a viscosity of 6% and a viscosity of 4500 cps/25°C was obtained. (C) 7 parts by weight of inphorone diisocyanate is blended with 100 parts by weight of the prepolymer B, and FNCo 8
．． An isocyanate mixture (hereinafter referred to as isocyanate a compound C) with a viscosity of 5% and a viscosity of 4000 cps/25°C was obtained. (3) Production of urethane elastomer The above prepolymer A-B and isocyanate mixture A
-C, according to the formulation in Table-1 below, main agent/curing agent =
By reacting at a weight ratio of 100/100, a urethane elastomer sheet with a thickness of 2 IIol was created. The results are shown in Table 2 below. (Leaving space below) Table-1 Table-2 Multi-bag body of Ihara Chemical Ezu-Sho J3 Heat Sticker Ship: Amine value 210 I1gKO! (/g Equivalent ratio of amine to m-total m-total ratio of amine to m-katana of prepolybu Jri Ire Shu Shikiron 4 Seal n Nitto Emperor H Jofu N5I1100 Nippon Kagaku Sangyo 5d Shishichi Shiki Knee/Chaotic Lead 2
0%Nihon Nijika Co., Ltd. Silicone Oil FZ5
825 [January■) After curing and soldering of the main agent, 6XIQ' cp using a B-type viscometer.
lI eyebrow 1 le until reaching s 2) -111° until almost no footprints are left even when walking in slippers 3) JIS
Measured in accordance with A3021. 4) Weather off-ter 60 books 1 processing. ■Bottom margin)
本発明は、以上説明したとおり、触媒の増量や易反応性
のインシア２−トの専用などといった常識的な方法によ
ることなしに公知の常温硬化性ウレタンエラストマーに
おける上記問題点を解決し、改良された急速硬化性、耐
候性及び物性を備える常温硬化性の新規ウレタンエラス
トマーを提供できたことにより、関連産業分野に寄与し
うる。As explained above, the present invention solves and improves the above-mentioned problems in known room temperature curable urethane elastomers without resorting to common-sense methods such as increasing the amount of catalyst or dedicating a highly reactive insear elastomer. By providing a new room-temperature curable urethane elastomer with rapid curing properties, weather resistance, and physical properties, the present invention can contribute to related industrial fields.
Claims (1)
硬化させて、常温硬化性のウレタンエラストマーを製造
するに当たり、イソシアネート化合物として芳香族ポリ
イソシアネートとポリオールとを予め反応させて得られ
る末端イソシアネート基含有ウレタンプレポリマー１０
０重量部に脂肪族ポリイソシアネートを１〜１５重量部
配合したイソシアネート混合物を用いることを特徴とす
る常温硬化性ウレタンエラストマーの製造法。1 Reacting an isocyanate compound and an active hydrogen compound,
Terminal isocyanate group-containing urethane prepolymer 10 obtained by reacting an aromatic polyisocyanate and a polyol as an isocyanate compound before curing to produce a room temperature curable urethane elastomer.
A method for producing a room temperature curable urethane elastomer, which comprises using an isocyanate mixture in which 0 parts by weight and 1 to 15 parts by weight of aliphatic polyisocyanate are blended.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2212192A JPH0496919A (en) | 1990-08-10 | 1990-08-10 | Production of room temperature curable urethane elastomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2212192A JPH0496919A (en) | 1990-08-10 | 1990-08-10 | Production of room temperature curable urethane elastomer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0496919A true JPH0496919A (en) | 1992-03-30 |
Family
ID=16618452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2212192A Pending JPH0496919A (en) | 1990-08-10 | 1990-08-10 | Production of room temperature curable urethane elastomer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0496919A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1177940A (en) * | 1997-09-17 | 1999-03-23 | Asahi Glass Co Ltd | Waterproof structure and forming method thereof |
| WO2013060088A1 (en) * | 2011-10-27 | 2013-05-02 | 山东东大一诺威聚氨酯有限公司 | Preparation method of rigid polyurethane |
| CN108102058A (en) * | 2018-01-11 | 2018-06-01 | 山东扬名新材料技术有限公司 | Single-component solvent-free self-leveling polyurethane elastomer |
-
1990
- 1990-08-10 JP JP2212192A patent/JPH0496919A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1177940A (en) * | 1997-09-17 | 1999-03-23 | Asahi Glass Co Ltd | Waterproof structure and forming method thereof |
| WO2013060088A1 (en) * | 2011-10-27 | 2013-05-02 | 山东东大一诺威聚氨酯有限公司 | Preparation method of rigid polyurethane |
| CN108102058A (en) * | 2018-01-11 | 2018-06-01 | 山东扬名新材料技术有限公司 | Single-component solvent-free self-leveling polyurethane elastomer |
| CN108102058B (en) * | 2018-01-11 | 2020-09-11 | 山东扬名新材料技术有限公司 | Single-component solvent-free self-leveling polyurethane elastomer |
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