JPH026479A - Blocked polyisocyanurate - Google Patents
Blocked polyisocyanurateInfo
- Publication number
- JPH026479A JPH026479A JP63157649A JP15764988A JPH026479A JP H026479 A JPH026479 A JP H026479A JP 63157649 A JP63157649 A JP 63157649A JP 15764988 A JP15764988 A JP 15764988A JP H026479 A JPH026479 A JP H026479A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound expressed
- nco
- blocked
- diisocyanate
- 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.)
- Granted
Links
- 229920000582 polyisocyanurate Polymers 0.000 title claims abstract description 6
- 239000011495 polyisocyanurate Substances 0.000 title claims abstract description 5
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 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 7
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 229920001944 Plastisol Polymers 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 4
- 239000003431 cross linking reagent Substances 0.000 abstract description 4
- 239000004999 plastisol Substances 0.000 abstract description 4
- 239000003566 sealing material 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000001133 acceleration Effects 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- -1 diisocyanate compound Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000002981 blocking agent 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
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
【発明の詳細な説明】
この種のブロック化ポリイソシアヌレートとしては、そ
の一部が既に公知である。たとえば、特開昭６２−４１
２７８号公報にジイソシアネート屯合物のＮＣＯ基を長
鎖アルキルフェノールでブロックしたものが記載され、
これは接着または被覆に適するＰＶＣ系プラスチゾル組
成物に配合する接着付与剤に用いるとされている。また
、特開昭６２−５３９７５号公報には、コーティング剤
、接着剤（あるいはその架橋剤）、活性水素含有高分子
の改質剤に用いる。ジイソシアネート徂合物のｏ、ｍ、
ｐ−安息香酸エステルブロック体の記載がある。DETAILED DESCRIPTION OF THE INVENTION Some of this type of blocked polyisocyanurates are already known. For example, JP-A-62-41
No. 278 describes a diisocyanate compound in which the NCO group is blocked with a long-chain alkylphenol,
This is said to be used as an adhesion promoter to be incorporated into PVC-based plastisol compositions suitable for adhesion or coating. Further, JP-A No. 62-53975 discloses that it is used in coating agents, adhesives (or crosslinking agents thereof), and modifiers for active hydrogen-containing polymers. Diisocyanate mixture o, m,
There is a description of a p-benzoic acid ester block.
本発明は、これらブロック体と異なり、ジイソシアネー
ト市合物およびそのブロック剤の種類を特定化したもの
で、接着剤、コーテイング材、シール材、活性水素含有
高分子の架橋剤として用いられ、たとえば自動車ボデー
のシール材に好適なＰＶＣプラスチゾル組成物の接着付
与剤として、特に１１０〜１３０℃の如き低温下での密
着性発現に有効な新規ブロック体の提供を目的とする。Unlike these block bodies, the present invention specifies the types of diisocyanate compounds and their blocking agents, which are used as adhesives, coating materials, sealing materials, and crosslinking agents for active hydrogen-containing polymers, such as in automobiles. The object of the present invention is to provide a new block body that is effective as an adhesion promoter for PVC plastisol compositions suitable for body sealing materials, particularly at low temperatures such as 110 to 130°C.
すなわち、本発明に係る新規ブロック体は、式、〔式中
、Ｘ、ＹおよびＺは相互に同一もしくは異なって、トリ
レンジイソシアネートまたはジフェニルメタンジイソシ
アネートのＮＣ○基を除いた残基、およびｎは１〜１０
である〕
で示されるブロック化ポリイソシアスレートである。That is, the novel block body according to the present invention has the formula: [wherein X, Y and Z are the same or different from each other, a residue of tolylene diisocyanate or diphenylmethane diisocyanate excluding the NC○ group, and n is 1 ~10
It is a blocked polyisocyanate represented by the following formula.
本発明ブロック体ＣＩＩは、以下の方法１または２の手
順に従って製造することができる。The block body CII of the present invention can be manufactured according to the following method 1 or 2.
方法ｌ
まず、式：
％式％
［
（式中、Ｘ、ＹおよびＺは前記と同意義）のジイソシア
ネート〔すなわち、トリレンジイソシアネート（２，４
−）リレンジイソシアネート、２．６−トリレンジイソ
シアネート）およびジフェニルメタンジイソシアネート
の１種、２種または３種］を、適当ｔ１反応溶媒（たと
えば酢酸エチル、酢酸ブチルなどの酢酸エステル類、メ
チルエチルケトン、メチルイソブチルケトンなどのケト
ン類、ジブチルフタレート、ジオクチルフタレートｆＬ
どのフタル酸エステル用、ジオキサン、テトラヒドロフ
ランなどのエーテル類、トルエン、キシレンなどの芳香
族化合物、その他ジメチルホルムアミド、Ｎ−メチルピ
ロリドン等）中、触媒（たとえば酢酸カリウム、酢酸ナ
トリウム、ステアリン酸ナトリウムなどの有機カルボン
酸のアルカリ金属塩、第３級アミン化合物、第４級アン
モニウム化合物、エポキシアミン化合物、フェノールア
ミン化合物等）の存在下、２０〜８０℃の温度でインシ
アヌレート化を行い、式：
（式中、ｘ、ｙ、ｚおよびｎは前記と同意義）のジイソ
シアネート眞合物であるポリイソシアヌレ ｈを得、次
いで該ポリイソシアヌレート［ｌ］Ｉ］を反応促進触媒
（ジブチルチンジラウレート、ジオクチルチンジラウレ
ート、スタナスオクトエートなどの有機錫化合物、ナフ
テン酸亜鉛、ナフテン酸コバルトなどのナフテン酸金１
寓塩、アセチルアセトン鉄、アセチルアセトンマンガン
、第３級アミン化合物等）の存在下、５０〜１００℃の
温度にて、式：
のスチレン化フェノールでブロック化することにより、
本発明ブロック体ＣＩＩを得る。Method 1 First, a diisocyanate [i.e., tolylene diisocyanate (2,4
-) lylene diisocyanate, 2,6-tolylene diisocyanate) and diphenylmethane diisocyanate] in an appropriate t1 reaction solvent (e.g., acetate esters such as ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone). Ketones such as dibutyl phthalate, dioctyl phthalate fL
For any phthalate ester, ethers such as dioxane and tetrahydrofuran, aromatic compounds such as toluene and xylene, and other organic compounds such as potassium acetate, sodium acetate, and sodium stearate. In the presence of an alkali metal salt of a carboxylic acid, a tertiary amine compound, a quaternary ammonium compound, an epoxy amine compound, a phenol amine compound, etc.) at a temperature of 20 to 80 °C, the inocyanurate is formed by the formula: (Formula Polyisocyanurate h, which is a diisocyanate compound (in which x, y, z, and n have the same meanings as above), was obtained, and then the polyisocyanurate [l]I] was mixed with a reaction promoting catalyst (dibutyltin dilaurate, dioctyltin dilaurate, Organotin compounds such as dilaurate and stannath octoate; gold naphthenates such as zinc naphthenate and cobalt naphthenate 1
By blocking with a styrenated phenol of the formula at a temperature of 50 to 100 ° C.
The block body CII of the present invention is obtained.
方法２
先ず、ジイソシアネート〔旧とスチレン化フエ／−ルｃ
ＩＶ）をＮＣ０１０Ｈの当量比が１．５〜４トなるよう
に反応させてブロック化を行った後、方法１と同様にイ
ソシアヌレート化を行い、本発明ブロック体ＣＩ］を得
る。なお、この場合の反応に用いる溶媒および触媒は、
方法１の場合に準じる。Method 2 First, diisocyanate [formerly and styrenated phenylene]
IV) is reacted with NCO10H in an equivalent ratio of 1.5 to 4 to form a block, and then isocyanurated in the same manner as in Method 1 to obtain the block product CI of the present invention. In addition, the solvent and catalyst used for the reaction in this case are:
Same as method 1.
このようにして製造される本発明ブロック体〔Ｉ〕は、
淡黄色透明粘稠液体を呈し、そのブロック剤か解離して
再生するＮＣＯ基含有量は、５〜２０％に設定されてい
る。特にＰｖＣ系プラスチゾル組成物の粘着付与剤また
は架橋剤として有用である。The block body [I] of the present invention produced in this way is:
The content of NCO groups, which exhibits a pale yellow transparent viscous liquid and is regenerated by dissociation of the blocking agent, is set at 5 to 20%. It is particularly useful as a tackifier or crosslinking agent for PvC plastisol compositions.
次に実施例を挙げて本発明をより具体的に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例Ｉ
ＴＤＩ−８０（２，４一体８０％と２．６一体２０％の
トリレンジイソシアネート）１５０ｙとジオクチルフタ
レ・−ト（ＤＯＰ）７５０ｙの溶液に、スチレン化フェ
ノール１００ｙおよびジブチルチンジラウレート０．５
９を加え、８０℃で６時間反応を行って部分ブロック化
ジイソシアネ−１・（遊離ＮＣＯ基含有計５．１％）を
得る。次いでこの反応溶液に、インシアヌレート化触媒
（酢酸カリウム）の５％メタノール溶液２ｙを添加し、
８０℃で反応させ、ＩＲでＮＧＯ基の吸収（２２５０ｃ
ｒｎ’）がなくなるまで反応を続ける。得られるブロッ
ク化ポリイソシアスレートの再生ＮＣＯ基含有計は８．
４％であ０す、ＩＲにより１４１０引−１にイソシアヌ
レート環の吸収を確認した。Example I To a solution of 150 y of TDI-80 (80% 2,4 and 20% 2.6 tolylene diisocyanate) and 750 y of dioctyl phthalate (DOP) was added 100 y of styrenated phenol and 0 y of dibutyltin dilaurate. .5
9 was added, and the reaction was carried out at 80° C. for 6 hours to obtain partially blocked diisocyanate-1. (total free NCO group content: 5.1%). Next, 2y of a 5% methanol solution of incyanurate catalyst (potassium acetate) was added to this reaction solution,
The reaction was carried out at 80°C, and the absorption of NGO groups (2250c
Continue the reaction until rn') is exhausted. The recycled NCO group content of the obtained blocked polyisocyanate was 8.
At 4%, absorption of isocyanurate rings was confirmed at 1410 pull-1 by IR.
実施例２
ＴＤＩ−８０（１５０ｙ）とＤＯＰ（４５０ｐ）の溶液
に酢酸カリウムの５％メタノール溶液２ｙを加え、７０
℃で５時間反応を行って、遊離ＮＣＯ基含有量４％のポ
リイソシアヌレ−トラ得る。Example 2 2y of a 5% methanol solution of potassium acetate was added to a solution of TDI-80 (150y) and DOP (450p), and 70
The reaction is carried out for 5 hours at DEG C. to obtain a polyisocyanurator with a free NCO group content of 4%.
次いでこの反応溶液に、スチレン化フェノール１３０ｐ
、ＤＯＰ（３９０ｙ）およびジブチルチンジラウレート
０．５ｇＩを添加し、８０℃で１０時間反応を行いブロ
ック化ポリイソシアスレートを得る。ＩＲによりＮＣＯ
基吸収（２２５０ｃｍ−〇のないことを確認、再生ＮＧ
Ｏ含有量８．８％、１４１０ｃｍ’ にイソシアヌレ
ート環吸収。Then, 130p of styrenated phenol was added to this reaction solution.
, DOP (390y) and 0.5 gI of dibutyltin dilaurate were added, and the reaction was carried out at 80° C. for 10 hours to obtain blocked polyisocyanate. NCO by IR
Confirm that there is no group absorption (2250cm-〇, regeneration NG)
O content 8.8%, isocyanurate ring absorption at 1410 cm'.
Claims (1)
、トリレンジイソシアネートまたはジフェニルメタンジ
イソシアネートのＮＣＯ基を除いた残基、およびｎは１
〜１０である〕 で示されるブロック化ポリイソシアヌレート。[Claims] 1. Formulas, ▲ Numerical formulas, chemical formulas, tables, etc. group, and n is 1
~10] A blocked polyisocyanurate represented by:
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63157649A JPH0816146B2 (en) | 1988-06-24 | 1988-06-24 | Blocked polyisocyanurate |
| DE3920325A DE3920325C2 (en) | 1988-06-24 | 1989-06-21 | Masked polyisocyanurate compound and plastisol composition containing it |
| US07/370,790 US4983655A (en) | 1988-06-24 | 1989-06-23 | Blocked polyisocyanurate compound and plastisol composition containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63157649A JPH0816146B2 (en) | 1988-06-24 | 1988-06-24 | Blocked polyisocyanurate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH026479A true JPH026479A (en) | 1990-01-10 |
| JPH0816146B2 JPH0816146B2 (en) | 1996-02-21 |
Family
ID=15654342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63157649A Expired - Lifetime JPH0816146B2 (en) | 1988-06-24 | 1988-06-24 | Blocked polyisocyanurate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0816146B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012041513A (en) * | 2010-04-14 | 2012-03-01 | Jsr Corp | Method for manufacturing polyisocyanurate compound |
-
1988
- 1988-06-24 JP JP63157649A patent/JPH0816146B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012041513A (en) * | 2010-04-14 | 2012-03-01 | Jsr Corp | Method for manufacturing polyisocyanurate compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0816146B2 (en) | 1996-02-21 |
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