JPH11286674A - One pack moisture-curable urethane composition - Google Patents
One pack moisture-curable urethane compositionInfo
- Publication number
- JPH11286674A JPH11286674A JP9007198A JP9007198A JPH11286674A JP H11286674 A JPH11286674 A JP H11286674A JP 9007198 A JP9007198 A JP 9007198A JP 9007198 A JP9007198 A JP 9007198A JP H11286674 A JPH11286674 A JP H11286674A
- Authority
- JP
- Japan
- Prior art keywords
- compsn
- curable urethane
- cyclopentadiene
- catalyst
- urethane composition
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 11
- 229920000570 polyether Polymers 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 6
- 229920005862 polyol Polymers 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims abstract description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 150000002009 diols Chemical class 0.000 abstract description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004014 plasticizer Substances 0.000 abstract 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 abstract description 3
- 239000000945 filler Substances 0.000 abstract description 3
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 abstract description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 6
- -1 malonate compound Chemical class 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 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
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- JJKMIZGENPMJRC-UHFFFAOYSA-N 3-oxo-3-propan-2-yloxypropanoic acid Chemical compound CC(C)OC(=O)CC(O)=O JJKMIZGENPMJRC-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 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
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、自動車用、建築用
および構造用のシーリング剤、接着剤およびコーティン
グ剤等として用いる一液湿気硬化型ウレタン組成物に関
し、更に詳しくは、触媒活性を低下させずかつ、湿分不
存在下における貯蔵安定性に優れ、かつ大気中の湿分で
十分な硬化性が得られる一液湿気硬化型ウレタン組成物
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a one-pack moisture-curable urethane composition for use as a sealing agent, an adhesive, a coating agent and the like for automobiles, buildings and structures, and more particularly, to a catalyst having reduced catalytic activity. The present invention relates to a one-pack moisture-curable urethane composition which is excellent in storage stability in the absence of moisture and has sufficient curability with moisture in the atmosphere.
【０００２】[0002]
【従来の技術】硬化性ウレタン組成物、特に一液湿気硬
化型ウレタン組成物の貯蔵安定性を確保するために、従
来は例えばジエチルマロネート（ＤＥＭ）、ジメチルマ
ロネート（ＤＭＭ）、イソプロピルマロネート（ＩＰ
Ｍ）などのマロネート化合物などが使用されてきた。し
かしながら、イソシアネート基存在下において、マロネ
ート化合物はジメチルアミノ基のような構造を持つ比較
的活性の高い触媒と併用すると、その触媒活性を低下さ
せるために、モルフォリン構造を有する触媒等の極めて
限定された構造の触媒しか併用することができないとい
う問題があった。このためモルフォリン系等の活性の弱
い触媒を大量に使用しなくてはならず、硬化特性、コス
ト高等の面で一液湿気硬化型ウレタン組成物の使用は極
めて制限されていた。2. Description of the Related Art In order to ensure the storage stability of a curable urethane composition, particularly a one-pack moisture-curable urethane composition, conventionally, for example, diethyl malonate (DEM), dimethyl malonate (DMM), isopropyl malonate (IP
Malonate compounds such as M) have been used. However, when a malonate compound is used in combination with a relatively active catalyst having a structure such as a dimethylamino group in the presence of an isocyanate group, the catalyst having a morpholine structure is extremely limited in order to reduce the catalytic activity. However, there is a problem that only a catalyst having a different structure can be used together. For this reason, a weakly active catalyst such as a morpholine-based catalyst must be used in a large amount, and the use of a one-pack moisture-curable urethane composition has been extremely limited in terms of curing characteristics and cost.
【０００３】[0003]
【発明が解決しようとする課題】従って、本発明の目的
は触媒活性の高いジメチルアミノ基構造などを有するア
ミン系触媒を使用してもその触媒活性を低下させること
はなく、かつ一液湿気硬化型ウレタン組成物の貯蔵安定
性を高めることのできる一液湿気硬化型ウレタン組成物
を提供することを目的とする。SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide an amine catalyst having a dimethylamino group structure having a high catalytic activity without lowering its catalytic activity and one-part moisture curing. It is an object of the present invention to provide a one-part moisture-curable urethane composition that can enhance the storage stability of a type urethane composition.
【０００４】[0004]
【課題を解決するための手段】本発明に従えば、アミン
系触媒を含む一液湿気硬化型ウレタン組成物において、
シクロペンタジエンを組成物重量当り０．００１〜３０
重量％配合したことを特徴とする一液湿気硬化型ウレタ
ン組成物が提供される。According to the present invention, there is provided a one-pack moisture-curable urethane composition containing an amine catalyst,
Cyclopentadiene is added in an amount of 0.001 to 30 per weight of the composition.
Provided is a one-part moisture-curable urethane composition characterized in that it is blended by weight.
【０００５】[0005]
【発明の実施の形態】本発明によれば、前述の如く、ア
ミン系触媒を含む一液湿気硬化型ウレタン組成物にシク
ロペンタジエンを配合することによりアミン系触媒の活
性を損なうことなく、一液湿気硬化型ウレタン組成物の
貯蔵安定性を高めることができる。このようにシクロペ
ンタジエンを一液湿気硬化型ウレタン組成物の貯蔵安定
剤として使用することにより、ジメチルアミノ基構造を
有する触媒の使用が可能となり、種々の硬化挙動が選択
できるようになり、また活性の高い触媒の使用が可能と
なりコスト的にも有利になった。According to the present invention, as described above, by mixing cyclopentadiene with a one-part moisture-curable urethane composition containing an amine-based catalyst, the one-part moisture-curable urethane composition can be prepared without impairing the activity of the amine-based catalyst. The storage stability of the moisture-curable urethane composition can be improved. By using cyclopentadiene as a storage stabilizer for a one-part moisture-curable urethane composition, a catalyst having a dimethylamino group structure can be used, and various curing behaviors can be selected, and the activity can be improved. This makes it possible to use a catalyst having a high water content, which is advantageous in terms of cost.
【０００６】本発明のウレタン組成物に配合するウレタ
ンプレポリマーは公知の物質であり、例えば一分子当り
３個以上の水酸基を有する、ポリオキシプロピレントリ
オールなどのポリエーテルポリオールなどのポリオール
成分と、一分子当り２個の水酸基を有するポリプロピレ
ンエーテルジオールなどのポリエーテルジオールなどの
ジオール成分との混合物に、４，４′−ジフェニルメタ
ンジイソシアネートを反応させて所望のウレタンプレポ
リマーを得ることができる。好ましいウレタンプレポリ
マーとしては、数平均分子量が１０００〜７０００のポ
リエーテルトリオールとポリエーテルジオールの混合物
に４，４′ジフェニルメタンジイソシアナートをＮＣＯ
基／ＯＨ基の当量比が１．１〜２．５になるように反応
させたものがあげられる。[0006] The urethane prepolymer blended in the urethane composition of the present invention is a known substance, for example, a polyol component having three or more hydroxyl groups per molecule, such as a polyether polyol such as polyoxypropylene triol, and a polyether polyol. A desired urethane prepolymer can be obtained by reacting a mixture with a diol component such as a polyether diol such as a polypropylene ether diol having two hydroxyl groups per molecule with 4,4'-diphenylmethane diisocyanate. As a preferred urethane prepolymer, a mixture of polyether triol and polyether diol having a number average molecular weight of 1,000 to 7000 is mixed with 4,4'-diphenylmethane diisocyanate by NCO.
What reacted so that the equivalent ratio of group / OH group might be 1.1-2.5 is mentioned.
【０００７】本発明において用いる硬化触媒は一般的に
一液湿気硬化型ウレタン組成物用に使用されているアミ
ン系触媒で例えばジモルホリノジエチルエーテル、Ｎ，
Ｎ′−ジメチルシクロヘキシルアミン、Ｎ，Ｎ′−ジメ
チルアミノエチルモルホリン、ビス（２−ジメチルアミ
ノエチル）エーテル、Ｎ，Ｎ′−ジメチルピペラジン、
Ｎ−メチルモルホリン、トリエチレンジアミン、トイソ
ブチル−２−メチルイミダゾール、ペンタメチルジエチ
ルトリアミンなどをあげることができる。触媒の配合量
にも特に限定はないが、好ましくはウレタン組成物重量
当り０．００１〜５重量％、更に好ましくは０．０１〜
３重量％である。The curing catalyst used in the present invention is an amine catalyst generally used for one-pack moisture-curable urethane compositions, such as dimorpholinodiethyl ether, N,
N'-dimethylcyclohexylamine, N, N'-dimethylaminoethylmorpholine, bis (2-dimethylaminoethyl) ether, N, N'-dimethylpiperazine,
Examples thereof include N-methylmorpholine, triethylenediamine, triisobutyl-2-methylimidazole, and pentamethyldiethyltriamine. The amount of the catalyst is not particularly limited, but is preferably 0.001 to 5% by weight, more preferably 0.01 to 5% by weight, based on the weight of the urethane composition.
3% by weight.
【０００８】本発明に係る一液湿気硬化型ポリウレタン
組成物には貯蔵安定剤としてシクロペンタジエンを組成
物重量当り０．００１〜３０重量％、好ましくは０．０
２〜２重量％配合する。このシクロペンタジエンの配合
量が０．００１重量％未満では貯蔵安定性、触媒活性の
死活をおさえられないので好ましくなく、逆に３０重量
％を超えると硬化物の物性低下が顕著となるので好まし
くない。The one-pack moisture-curable polyurethane composition according to the present invention contains cyclopentadiene as a storage stabilizer in an amount of 0.001 to 30% by weight, preferably 0.03% by weight, based on the weight of the composition.
2 to 2% by weight is blended. If the amount of cyclopentadiene is less than 0.001% by weight, storage stability and catalytic activity cannot be suppressed, and if it is more than 30% by weight, physical properties of a cured product are remarkably deteriorated. .
【０００９】本発明の一液湿気硬化型ウレタン組成物に
は、所望の物性等を付与するために、前記した必須成分
に加えて、イソシアネート基に対して不活性な充填剤、
可塑剤、溶剤等を含有せしめることができる。例えば、
充填剤としては、カーボンブラック、クレー、タルク、
炭酸カルシウムなど又はこれらの混合物が挙げられ、可
塑剤としては、ジプチルフタレート、ジオクチルフタレ
ート等のフタル酸誘導体をはじめ、テトラヒドロフタル
酸、アゼライン酸、マレイン酸、トリメリット酸、イソ
フタール酸、アジピン酸、イタコン酸、クエン酸等の誘
導体が、溶剤としては、トルエン、キシレン等の芳香族
炭化水素系溶剤等が例示される。The one-part moisture-curable urethane composition of the present invention has, in addition to the above-mentioned essential components, a filler inert to isocyanate groups, in order to impart desired physical properties and the like.
A plasticizer, a solvent and the like can be contained. For example,
Fillers include carbon black, clay, talc,
Such as calcium carbonate or a mixture thereof, as a plasticizer, including phthalic acid derivatives such as dibutyl phthalate and dioctyl phthalate, tetrahydrophthalic acid, azelaic acid, maleic acid, trimellitic acid, isophthalic acid, adipic acid, Derivatives such as itaconic acid and citric acid, and examples of the solvent include aromatic hydrocarbon solvents such as toluene and xylene.
【００１０】本発明のウレタン組成物には、特に限定は
ないが、硬化触媒および溶剤を除く各成分を減圧下に充
分混練し、均一に分散した後、硬化触媒をキシレン等の
溶媒に溶かして加え、減圧下にさらに充分混練して組成
物とするのが良い。The urethane composition of the present invention is not particularly limited, but the components other than the curing catalyst and the solvent are sufficiently kneaded under reduced pressure, uniformly dispersed, and then the curing catalyst is dissolved in a solvent such as xylene. In addition, the composition may be further kneaded under reduced pressure to obtain a composition.
【００１１】[0011]
【実施例】以下、実施例によって本発明を更に説明する
が、本発明の範囲をこれらの実施例に限定するものでな
いことは言うまでもない。EXAMPLES The present invention will be further described with reference to the following examples, but it goes without saying that the scope of the present invention is not limited to these examples.
【００１２】実施例１〜２及び比較例１〜２ 平均分子量５０００のポリエーテルトリオールと平均分
子量２０００のポリエーテルジオールを重量比６／４で
混合し１１０℃で脱水後、溶融した４，４′−ジフェニ
ルメタンジイソシアネートをＮＣＯ基／ＯＨ基の当量比
が１．７になるよな量を加え８０℃窒素置換中で３６時
間混合撹拌してプレポリマーを得た。このようにして得
られたプレポリマーにプレポリマー１００重量部当り可
塑剤としてジオクチルフタレート３０重量部、カーボン
ブラック７０重量部を添加し真空下でミキサーで１時間
混合後、触媒としてビス（２−ジメチルアミノエチル）
エーテルと貯蔵安定剤としてシクロペンタジエンを加え
てさらに１０分間混合しウレタン予備組成物を得た。 Examples 1 and 2 and Comparative Examples 1 and 2 Polyether triol having an average molecular weight of 5,000 and polyether diol having an average molecular weight of 2,000 were mixed at a weight ratio of 6/4, dehydrated at 110 ° C., and melted. -Diphenylmethane diisocyanate was added in such an amount that the equivalent ratio of NCO group / OH group became 1.7, and the mixture was stirred and stirred at 80 ° C for 36 hours in a nitrogen atmosphere to obtain a prepolymer. To the prepolymer thus obtained, 30 parts by weight of dioctyl phthalate and 70 parts by weight of carbon black were added as a plasticizer per 100 parts by weight of the prepolymer, and mixed under a vacuum for 1 hour. Aminoethyl)
Ether and cyclopentadiene as a storage stabilizer were added and mixed for another 10 minutes to obtain a urethane preliminary composition.
【００１３】表Ｉに示すように、触媒としてビス（２−
ジメチルアミノエチル）エーテル及び安定剤としてジク
ロペンタジエンを表Ｉに示す配合量で配合してウレタン
予備組成物を得、それらの貯蔵安定性及び硬化性を測定
した。結果を表Ｉに示す。As shown in Table I, bis (2-
Dimethylaminoethyl) ether and diclopentadiene as stabilizers were blended in the amounts shown in Table I to obtain urethane pre-compositions, and their storage stability and curability were measured. The results are shown in Table I.
【００１４】[0014]
【表１】 [Table 1]
【００１５】＊１：貯蔵安定性評価 配合後、２０℃で２４時間放置した後及び２０℃下に３
ヶ月放置したものの粘度を測定した。* 1: Storage stability evaluation After blending, leave at 20 ° C. for 24 hours and at 20 ° C. for 3 hours.
The viscosity of the sample left for months was measured.
【００１６】＊２：硬化性評価 配合後、２０℃下に２４時間放置した後と、２０℃下に
３ヶ月放置したものについて、２０℃、６５％ＲＨ下に
て、塗布後に表面タックがなくなるまでの時間を測定し
た。* 2: Evaluation of curability After compounding, after leaving for 24 hours at 20 ° C. and for 3 months at 20 ° C., surface tack disappears after application at 20 ° C. and 65% RH. The time until was measured.
【００１７】[0017]
【発明の効果】以上の通り、シクロベンタジエンをウレ
タン貯蔵安定剤として使用することにより、ジメチルア
ミノ基構造を有する触媒の使用が可能となり、種々の硬
化挙動を選択出来るようになると共に、活性の高い触媒
の使用が可能となり、実用上コスト的にも有利になる。As described above, by using cyclopentadiene as a urethane storage stabilizer, a catalyst having a dimethylamino group structure can be used, and various curing behaviors can be selected. A high catalyst can be used, which is practically advantageous in cost.
Claims (3)
タン組成物において、シクロペンタジエンを組成物重量
当り０．００１〜３０重量％配合したことを特徴とする
一液湿気硬化型ウレタン組成物。1. A one-pack moisture-curable urethane composition containing an amine catalyst, wherein cyclopentadiene is blended in an amount of 0.001 to 30% by weight based on the weight of the composition.
チルアミノ基構造を有する触媒である請求項１又は２に
記載の組成物。2. The composition according to claim 1, wherein the amine catalyst is a catalyst having a morpholine or dimethylamino group structure.
がイソシアネート官能価２．２〜３．０のポリエーテル
ポリオールである請求項１に記載の組成物。3. The composition according to claim 1, wherein the polyol component of the urethane prepolymer is a polyether polyol having an isocyanate functionality of 2.2 to 3.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9007198A JPH11286674A (en) | 1998-04-02 | 1998-04-02 | One pack moisture-curable urethane composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9007198A JPH11286674A (en) | 1998-04-02 | 1998-04-02 | One pack moisture-curable urethane composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11286674A true JPH11286674A (en) | 1999-10-19 |
Family
ID=13988311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9007198A Pending JPH11286674A (en) | 1998-04-02 | 1998-04-02 | One pack moisture-curable urethane composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH11286674A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008038019A (en) * | 2006-08-07 | 2008-02-21 | Yokohama Rubber Co Ltd:The | One pack moisture-curing type urethane resin composition |
-
1998
- 1998-04-02 JP JP9007198A patent/JPH11286674A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008038019A (en) * | 2006-08-07 | 2008-02-21 | Yokohama Rubber Co Ltd:The | One pack moisture-curing type urethane resin composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6136942A (en) | Latent amino groups and isocyanate groups comprising polyurethane prepolymers, method for their production and their use | |
| JPH078982B2 (en) | Moisture curable sealant composition | |
| JPH11286674A (en) | One pack moisture-curable urethane composition | |
| KR100593583B1 (en) | One-Pack Type Moisture Curable Urethane Composition | |
| JP4061516B2 (en) | Moisture curable urethane resin composition and coating material | |
| JP3964102B2 (en) | Curable composition | |
| JP2002212534A (en) | One-pack type moisture-curing urethane adhesive composition | |
| JP3386208B2 (en) | Urethane moisture-curable composition | |
| JP3780691B2 (en) | Two-component curable urethane composition and sealing material | |
| JPH10121031A (en) | Sealant composition | |
| JPH10182786A (en) | Curable type composition | |
| JPS638155B2 (en) | ||
| JP3340962B2 (en) | One-part moisture-curable urethane resin composition | |
| JPH0841155A (en) | Moisture curable polyurethane composition | |
| JP4524068B2 (en) | 1 liquid moisture curable urethane resin composition | |
| JPH07292064A (en) | Curable composition | |
| JP2749763B2 (en) | Polyurethane resin composition | |
| JP2000302833A (en) | Catalyst for moisture curing of urethane prepolymer and one-part moisture cure type urethane-based hot melt adhesive | |
| JP2000297232A (en) | Moisture-curing primer composition and its production | |
| JP2000044795A (en) | One pack type moisture-curing urethane resin composition | |
| JPH03188120A (en) | Moisture-curing urethane composition | |
| JPH0517553A (en) | Moisture curable urethane resin composition and sealing material, waterproof material, flooring material and paving material using the same | |
| CN121379342A (en) | Odorless environment-friendly single-component polyurethane waterproof coating and preparation method thereof | |
| JPH11322894A (en) | Moisture-curable urethane composition and coating material | |
| JP2000234013A (en) | One-pack moisture-curable polyurethane composition and its production |