JPH0768158A - Producton of capsule containing isocyanate compound - Google Patents
Producton of capsule containing isocyanate compoundInfo
- Publication number
- JPH0768158A JPH0768158A JP16731793A JP16731793A JPH0768158A JP H0768158 A JPH0768158 A JP H0768158A JP 16731793 A JP16731793 A JP 16731793A JP 16731793 A JP16731793 A JP 16731793A JP H0768158 A JPH0768158 A JP H0768158A
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate compound
- isocyanate
- diisocyanate
- producton
- capsule containing
- 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
- 239000012948 isocyanate Substances 0.000 title claims abstract description 23
- 239000002775 capsule Substances 0.000 title claims abstract description 15
- -1 isocyanate compound Chemical class 0.000 title claims description 17
- 229920000098 polyolefin Polymers 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 150000002513 isocyanates Chemical class 0.000 abstract description 8
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000002023 wood 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
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- TXTIIWDWHSZBRK-UHFFFAOYSA-N 2,4-diisocyanato-1-methylbenzene;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)CO.CC1=CC=C(N=C=O)C=C1N=C=O TXTIIWDWHSZBRK-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
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- ZNXHWPFMNPRKQA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.N=C=O.C(C1=CC=CC=C1)C1=CC=CC=C1 ZNXHWPFMNPRKQA-UHFFFAOYSA-N 0.000 description 1
- HUBWWSYCEZBPRA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=NC=NC=N1 Chemical compound N=C=O.N=C=O.N=C=O.C1=NC=NC=N1 HUBWWSYCEZBPRA-UHFFFAOYSA-N 0.000 description 1
- PFSNIYFLNGYTIC-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical class N=C=O.N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 PFSNIYFLNGYTIC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003568 thioethers Chemical class 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
- 239000013638 trimer Substances 0.000 description 1
Landscapes
- Manufacturing Of Micro-Capsules (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、イソシアネート系化合
物を内包するカプセルを製造する方法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing capsules containing an isocyanate compound.
【0002】[0002]
【従来の技術】従来より、イソシアネート系化合物を内
包するカプセルはいくつかが知られている。中でも代表
的なものとして、曇点を有するポリビニルアセタール系
樹脂を壁膜材料として用いたものが知られている(例え
ば特開昭54−139885号公報)。ところがこのよ
うなカプセルは、水中にて凝析値の大きい無機物がその
塩類で凝固された後、取り出されるので、そのカプセル
の被覆膜となるポリビニルアセタールは化学的に反応し
ておらず、耐水性に乏しいという問題があった。2. Description of the Related Art Conventionally, some capsules containing an isocyanate compound are known. Among them, as a representative one, one using a polyvinyl acetal resin having a cloud point as a wall film material is known (for example, JP-A-54-139885). However, such capsules are taken out after the inorganic matter having a large coagulation value is solidified with the salts in water, and the polyvinyl acetal that forms the coating film of the capsules has not chemically reacted and is water resistant. There was a problem of being scarce.
【0003】また、ポリビニルアルコール系重合体より
なる壁を有するイソシアネートカプセルも知られている
(例えば特公昭63−6258号公報)。しかしながら
このカプセルには耐水性はあるものの、原料の種類が多
いこと及び酸触媒による硬化工程が必要で、実務的な製
造方法としては問題があった。Further, an isocyanate capsule having a wall made of a polyvinyl alcohol polymer is known (for example, Japanese Patent Publication No. 63-6258). However, although this capsule has water resistance, it has a problem as a practical manufacturing method because it has many kinds of raw materials and needs a curing step using an acid catalyst.
【0004】[0004]
【発明が解決しようとする課題】従って本発明は、得ら
れたイソシアネート系化合物のカプセルに耐水性があっ
て而も容易に製造ができる方法を提供することを目的と
するものである。SUMMARY OF THE INVENTION It is therefore an object of the present invention to provide a method in which the obtained isocyanate compound capsules have water resistance and can be easily produced.
【0005】[0005]
【課題を解決するための手段】上記目的を解決するため
に、低級ポリオレフィン類を用いてイソシアネート系化
合物を内包したカプセルを製造する方法を提供するもの
である。より詳しくは、イソシアネート系化合物と低級
ポリオレフィン類を熱溶融すると共に混合し、この混合
体を冷却固化させた後、破砕することによりイソシアネ
ート系化合物を内包するカプセルを製造する方法であ
る。In order to solve the above-mentioned object, a method for producing capsules containing an isocyanate compound using a lower polyolefin is provided. More specifically, it is a method of producing a capsule containing an isocyanate compound by heat-melting and mixing an isocyanate compound and lower polyolefins, cooling and solidifying the mixture, and then crushing.
【0006】本発明に用いることができる低級ポリオレ
フィン類としては、融点が80℃乃至160℃以下のも
のが好適である。融点が80℃未満では、カプセルの壁
材となったポリオレフィンが常温でも影響を受けブロッ
キングを起こしたり或は溶融する傾向があるので好まし
くない。また融点が160℃ を越える低級ポリオレフ
ィン類では、イソシアネート系化合物が混合されるとき
にイソシアネート基が活性化してしまい空気中の水分と
反応してしまう傾向があるので好ましくない。As the lower polyolefins which can be used in the present invention, those having a melting point of 80 ° C. to 160 ° C. or less are preferable. If the melting point is less than 80 ° C., the polyolefin that has become the wall material of the capsule is affected at room temperature and tends to cause blocking or melting, which is not preferable. Further, lower polyolefins having a melting point of higher than 160 ° C. are not preferable because the isocyanate groups are activated when the isocyanate compound is mixed and tend to react with moisture in the air.
【0007】イソシアネート基が反応し難い温度範囲で
あっても、溶融した低級ポリオレフィン類の粘度が余り
に高いと通常の攪拌機では充分な攪拌がし難くなるの
で、粘度は低い方が好ましい。例えば110℃即ち実務
的作業温度に於ける粘度は、100,000センチポイ
ズ以下好ましくは10,000センチポイズ以下であ
る。Even in the temperature range in which the isocyanate group is difficult to react, if the viscosity of the melted lower polyolefin is too high, it is difficult to sufficiently stir it with an ordinary stirrer. Therefore, the lower viscosity is preferable. For example, the viscosity at 110 ° C., that is, at working temperature is 100,000 centipoises or less, preferably 10,000 centipoises or less.
【0008】本発明に用いることができる低級ポリオレ
フィン類の種類としては、ポリエチレンワックス、ポリ
プロピレンワックス、これらの変成体、酸化ワックスな
どがあるが、要は融点が80℃乃至160℃のものであ
れば良い。Types of lower polyolefins that can be used in the present invention include polyethylene wax, polypropylene wax, modified products thereof, and oxidized wax. The point is that the melting point is 80 ° C. to 160 ° C. good.
【0009】本発明で用い得るイソシアネート系化合物
としては液状または粉体状のものが好適で例えばトリレ
ンジイソシアネート、キシリレンジイソシアネート、フ
ェニレンジイソシアネート、ジフェニルメタンシ゛イソシ
アネートなど並びにこれらの異性体及び核体からなる芳
香族ジイソシアネート、1,6−ヘキサメチレンジイソ
シアネート、1,12−ドデカンジイソシアネート等の
脂肪族ジイソシアネート、シクロヘキサン−1,4−ジ
イソシアネート、イソホロンジイソシアネート、4,
4’ジシクロヘキシルメタンジイソシアネート等の脂環
式ジイソシアネート、ω,ω’−(ジトリメチレンチオ
エーテル)ジイソシアネート等のジイソシアネート化合
物類、S−トリアジントリイソシアネート、チオリン酸
トリス(p−イソシアネートフェニル)エステル、トリ
フェニルメタントリイソシアネート、ジフェニルメタン
トリイソシアネート、ブタン−1,2,2−トリイソシ
アネート、トリメチロールプロパントリレンジイソシア
ネート3量付加体、2,4,’−ジフェニルエーテルト
リイソシアネート類、ポリメチレンポリフェニルイソシ
アネート等のポリイソシアネート化合物などが例示され
る。The isocyanate-based compound that can be used in the present invention is preferably a liquid or powdery one, for example, tolylene diisocyanate, xylylene diisocyanate, phenylene diisocyanate, diphenylmethane diisocyanate and the like, and aromatics consisting of isomers and nuclei thereof. Aliphatic diisocyanates such as diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclohexane-1,4-diisocyanate, isophorone diisocyanate, 4,
Alicyclic diisocyanates such as 4′-dicyclohexylmethane diisocyanate, diisocyanate compounds such as ω, ω ′-(ditrimethylene thioether) diisocyanate, S-triazine triisocyanate, thiophosphoric acid tris (p-isocyanate phenyl) ester, triphenylmethane triisocyanate Isocyanates, diphenylmethane triisocyanate, butane-1,2,2-triisocyanate, trimethylolpropane tolylene diisocyanate trimer adduct, 2,4'-diphenyl ether triisocyanates, polyisocyanate compounds such as polymethylene polyphenyl isocyanate, etc. Is exemplified.
【0010】また、これらの化合物と活性水素含有化合
物との反応によるイソシアネート基末端化合物、イソシ
アヌレート化反応などによるイソシアネート変成体など
も挙げられる。また。メタノール、アセト酢酸エチル、
ε−カプロラクタム、メチルエチルケトンオキシム、フ
ェノールなどの活性水素を分子内に1個有するブロック
剤で一部を安定化したポリイソシアネートなども使用す
ることができる。Further, an isocyanate group-terminated compound obtained by reacting these compounds with an active hydrogen-containing compound, and an isocyanate modified product obtained by an isocyanurate-forming reaction are also included. Also. Methanol, ethyl acetoacetate,
It is also possible to use polyisocyanate partially stabilized with a blocking agent having one active hydrogen in the molecule, such as ε-caprolactam, methyl ethyl ketone oxime, and phenol.
【0011】本発明に用いる低級ポリオレフィン類の使
用割合は、イソシアネート系化合物のNCO基に対して
0.1乃至100倍(重量換算値)が好ましく、0.5
乃至100倍(重量換算値)がより好ましい。The proportion of the lower polyolefins used in the present invention is preferably 0.1 to 100 times (weight conversion value) the NCO group of the isocyanate compound, and is 0.5.
To 100 times (value in terms of weight) is more preferable.
【0012】本発明では、冷却固化法としては各種用い
ることができる。例えばニーダ・ルーダと呼ばれる混練
押出機からフィルム状やストランド状に空気中に押し出
しても良いし、モールルド型に流し込んで固めても良
い。要は冷却して固めるものであれば良い。In the present invention, various methods can be used as the cooling and solidifying method. For example, it may be extruded in the form of a film or strand into the air from a kneading extruder called kneader-ruder, or may be poured into a mold and solidified. The point is that it can be cooled and solidified.
【0013】[0013]
【実施例】以下本発明について実施例を参照しながら説
明するが、本発明が当該実施例に限定されないことは勿
論である。 (実施例)低級ポリオレフィン類としてポリエチレンワ
ックス(商品名:ポリレッツ200、チュウセイワック
スポリマー株式会社製、融点:114℃)100重量部
バット内で加熱して溶融させ攪拌しながら120℃まで
昇温し加熱を停止した。これにイソシアネート系化合物
として(商品名:コロネート−1025、NCO含有率
40%、粘度:30cps/25℃)100重量部を徐
々に添加して、低級ポリオレフィン類とイソシアネート
系化合物との混合体を得た。EXAMPLES The present invention will be described below with reference to examples, but it goes without saying that the present invention is not limited to the examples. (Example) 100 parts by weight of polyethylene wax (trade name: Polyletts 200, manufactured by Chusei Wax Polymer Co., Ltd., melting point: 114 ° C.) as lower polyolefins, melted by heating in a vat and heated to 120 ° C. with stirring. The heating was stopped. To this, 100 parts by weight (trade name: Coronate-1025, NCO content 40%, viscosity: 30 cps / 25 ° C.) as an isocyanate compound was gradually added to obtain a mixture of lower polyolefins and an isocyanate compound. It was
【0014】この混合体をステンレス性のバットに流し
込んで厚み約5mmの平板状塊を得た。この塊を自由粉
砕機(M2−8型、奈良機械製作所製)破砕して、粒径
10乃至1000ミクロン(μm)の粉状体を得た。得
られた粉状体のイソシアネート基含有量は19.8重量
%であった。また50ミクロン以下の粒径を有する粉状
体は全体の25重量%であった。この紛状体を24時間
25℃の水中に置いた後、イソシアネート含有量を測定
したところ18.8重量%であった。This mixture was poured into a stainless steel vat to obtain a flat lump having a thickness of about 5 mm. This lump was crushed by a free crusher (M2-8 type, manufactured by Nara Machinery Co., Ltd.) to obtain a powdery substance having a particle size of 10 to 1000 microns (μm). The isocyanate group content of the obtained powder was 19.8% by weight. Further, the powdery matter having a particle size of 50 microns or less was 25% by weight of the whole. After the powder was placed in water at 25 ° C. for 24 hours, the isocyanate content was measured and found to be 18.8% by weight.
【0015】[0015]
【発明の効果】本発明は、上述のようにイソシアネート
基が安定に残存するので水と併用ができるもので、例え
ば木屑と本発明イソシアネート系化合物のカプセルとを
混合し、加熱して合成板を安全に製造することができる
という利点がある。水と併用できるので、カプセル化し
ていない生のイソシアネートのような危険性がない。ま
た木屑と混練後加熱するときに、オレフィンワックスが
溶融し通常の接着作用を呈すると共にオレフィンワック
スは耐水性、撥水性に寄与するという利点もある。INDUSTRIAL APPLICABILITY The present invention can be used in combination with water because the isocyanate group remains stable as described above. For example, wood chips and capsules of the isocyanate compound of the present invention are mixed and heated to form a synthetic plate. There is an advantage that it can be manufactured safely. Since it can be used with water, it does not have the danger of unencapsulated raw isocyanate. Further, when heated after kneading with wood chips, the olefin wax has an advantage that it melts and exhibits a normal adhesive action, and the olefin wax contributes to water resistance and water repellency.
Claims (2)
フィン類を熱溶融すると共に混合し、この混合体を冷却
固化させた後、破砕することによりイソシアネート系化
合物を内包するカプセルを製造する方法。1. A method for producing a capsule containing an isocyanate compound by heat-melting and mixing an isocyanate compound and lower polyolefins, cooling and solidifying the mixture, and then crushing.
℃乃至160℃である請求項1の方法。2. The melting point of the lower polyolefins is 80.
The method of claim 1, wherein the temperature is between 0 ° C and 160 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16731793A JPH0768158A (en) | 1993-06-15 | 1993-06-15 | Producton of capsule containing isocyanate compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16731793A JPH0768158A (en) | 1993-06-15 | 1993-06-15 | Producton of capsule containing isocyanate compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0768158A true JPH0768158A (en) | 1995-03-14 |
Family
ID=15847513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16731793A Pending JPH0768158A (en) | 1993-06-15 | 1993-06-15 | Producton of capsule containing isocyanate compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0768158A (en) |
-
1993
- 1993-06-15 JP JP16731793A patent/JPH0768158A/en active Pending
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