JPH0456046B2 - - Google Patents
Info
- Publication number
- JPH0456046B2 JPH0456046B2 JP58130935A JP13093583A JPH0456046B2 JP H0456046 B2 JPH0456046 B2 JP H0456046B2 JP 58130935 A JP58130935 A JP 58130935A JP 13093583 A JP13093583 A JP 13093583A JP H0456046 B2 JPH0456046 B2 JP H0456046B2
- Authority
- JP
- Japan
- Prior art keywords
- polybutadiene polyol
- lactone
- parts
- present
- polymer
- 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.)
- Expired - Lifetime
Links
- 150000002596 lactones Chemical class 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 21
- 239000005062 Polybutadiene Substances 0.000 claims description 16
- 229920002857 polybutadiene Polymers 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- JTDNNCYXCFHBGG-UHFFFAOYSA-L tin(ii) iodide Chemical compound I[Sn]I JTDNNCYXCFHBGG-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 229940108184 stannous iodide Drugs 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- -1 ε-caprolactone Chemical class 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
本発明は新規なラクトン重合体の製造方法に関
する。
さらに詳しくはポリブタジエンポリオールを開
始剤に用いてラクトン類を開環重合させることを
特徴とする新規なラクトン重合体の製造方法に関
する。
ラクトン重合体はエラストマー、合成皮革等の
ポリウレタン重合体及び塗料等の原料として非常
に有用なものである。しかし、従来から知られて
いるエチレングリコール、ジエチレングリコー
ル、１，４ブタンジオール等の開始剤を用いてラ
クトン類を開環重合させて得られたラクトン重合
体はいずれも結晶性を有し融点が高く、常温にお
いてワツクス状のものが大半である。従つて、ポ
リウレタン重合体を製造する場合、加温溶融して
取り扱う必要があり、作業性が悪いという欠点が
ある。
一方、ポリブタジエンポリオールはエラストマ
ー、接着剤、シーラント材等のポリウレタン重合
体及び塗料等の原料として有用なものである。
しかし、ポリブタジエンポリオールは常温にお
いて液状であるが、粘度が非常に高いため作業性
が悪い。又、ポリウレタン重合体の凝集力が弱
く、強度が低いという欠点がある。
本発明者は、これらの欠点を改良すべく鋭意検
討した結果、本発明に到つた。
すなわち、本発明はポリブタジエンポリオール
を開始剤に用いてラクトン類を開環重合したもの
である。
本発明者らは、本発明によつて得られる新規な
ラクトン重合体が、従来品の欠点を改良し、さら
にポリイソシアネートと反応して優れた物性を示
すポリウレタン重合体を提供することを見いだし
本発明に到達した。
本発明に使用するラクトン類は、環の中に４以
上、好ましくは６またはそれ以上の炭素原子を持
つ。好ましいラクトンは５員環ないし８員環のラ
クトンであり、例えばε−カプロラクトン、８−
バレロラクトン、γ−ブチロラクトン等がある。
本発明において使用されるポリブタジエンポリ
オールとしては、水酸基末端ポリブタジエンオリ
ゴマー（ポリブタジエン水酸基末端液状ポリマ
ー）があげられる。このものの水酸基価は通常25
〜230、好ましくは30〜100、とくに好ましくは35
〜70である。
ポリブタジエンポリオールとしては、１，２−
タイプ、１，４−タイプ、又はこれらの混合物で
ある。ポリブタジエンポリオールは具体的には、
米国のARCO社のPoly Bd及び日本曹達社の
NISSO−PBGシリーズがあげられる。Poly Bd
には、ブタジエンホモポリマータイプ及びコポリ
マータイプ（スチレンブタジエンコポリマー、ア
クロニトリルブタジエンコポリマー）が含まれ
る。その化学構造は次のとおりである。
ホモポリマータイプ
ｎ：55（Ｒ−45Mの場合）
50（Ｒ−45HTの場合）
コポリマータイプ
Ｘ：C6H5（CS−15）
ａ＝0.75，ｂ＝0.25，ｎ＝54
Ｘ：CN（CN−15）
ａ＝0.85，ｂ＝0.15，ｎ＝78〜87
分子量は通常2500〜4500、官能基数は通常２〜
３である。
また、NISSO−PBGシリーズの化学構造は次
のとおりである。
具体的には、Ｇ−1000，Ｇ−2000，Ｇ−3000が
あり、分子量は通常500〜3500である。
ポリブタジエンポリオールは特開昭55−98220
号、日本ゴム協会誌第45巻（1972）の449〜450
頁、シーランツ（ダムシス著、レインホールド
社、1967年発行）にも記載されている。
ラクトン類の重合を開始し、かつ連続的に行な
わせるには、ラクトン類と開始剤とを約100〜220
℃、好ましくは160〜180℃に加熱する。あまり高
温にすると熱分解が起り、好ましくない。
なお、開環重合にあたつては、好ましくは反応
促進の触媒を存在させる。触媒としてはテトラブ
チルチタネート、テトラプロピルチタネート、テ
トラエチルチタネート等の有機チタン系化合物、
オクチル酸スズ、ジブチルスズオキサイド、ジブ
チルスズラウレート等の有機スズ化合物、塩化第
１スズ、臭化第１スズ、ヨウ化第１スズ等のハロ
ゲン化第１スズ等を0.05〜1000ppm、好ましくは
0.1〜100ppm用いる。
本発明方法により得られるラクトン変性重合体
は両末端が水酸基である線状重合体であり、分子
量は通常1000〜5000程度である。分子量の調節は
重合開始剤と原料ラクトンのモル比を定めること
により行なうことができる。
本発明の好ましいラクトン変性重合体は、ポリ
ブタジエンポリオールからなるブロツクと、
The present invention relates to a novel method for producing lactone polymers. More specifically, the present invention relates to a novel method for producing a lactone polymer, which is characterized by ring-opening polymerization of lactones using polybutadiene polyol as an initiator. Lactone polymers are very useful as raw materials for elastomers, polyurethane polymers such as synthetic leather, and paints. However, all lactone polymers obtained by ring-opening polymerization of lactones using conventionally known initiators such as ethylene glycol, diethylene glycol, and 1,4-butanediol have crystallinity and a high melting point. Most of them are wax-like at room temperature. Therefore, when producing a polyurethane polymer, it is necessary to handle it by heating and melting it, which has the drawback of poor workability. On the other hand, polybutadiene polyol is useful as a raw material for polyurethane polymers such as elastomers, adhesives, sealants, and paints. However, although polybutadiene polyol is liquid at room temperature, its viscosity is extremely high, resulting in poor workability. Another disadvantage is that the cohesive force of the polyurethane polymer is weak and its strength is low. The present inventor has conducted intensive studies to improve these drawbacks, and as a result, has arrived at the present invention. That is, the present invention involves ring-opening polymerization of lactones using polybutadiene polyol as an initiator. The present inventors have discovered that the novel lactone polymer obtained by the present invention improves the drawbacks of conventional products and provides a polyurethane polymer that reacts with polyisocyanate and exhibits excellent physical properties. invention has been achieved. The lactones used in the invention have 4 or more, preferably 6 or more carbon atoms in the ring. Preferred lactones are 5- to 8-membered ring lactones, such as ε-caprolactone, 8-
Examples include valerolactone and γ-butyrolactone. Examples of the polybutadiene polyol used in the present invention include hydroxyl-terminated polybutadiene oligomers (polybutadiene hydroxyl-terminated liquid polymers). The hydroxyl value of this product is usually 25
~230, preferably 30-100, particularly preferably 35
~70. As polybutadiene polyol, 1,2-
type, 1,4-type, or a mixture thereof. Specifically, polybutadiene polyol is
Poly Bd from ARCO in the US and Nippon Soda
One example is the NISSO-PBG series. Poly Bd
Includes butadiene homopolymer types and copolymer types (styrene butadiene copolymer, acronitrile butadiene copolymer). Its chemical structure is as follows. Homopolymer type n: 55 (for R-45M) 50 (for R-45HT) Copolymer type X: C 6 H 5 (CS-15) a=0.75, b=0.25, n=54 X: CN (CN-15) a=0.85, b=0.15, n=78-87 Molecular weight is usually 2500-4500, The number of functional groups is usually 2~
It is 3. In addition, the chemical structure of the NISSO-PBG series is as follows. Specifically, there are G-1000, G-2000, and G-3000, and the molecular weight is usually 500 to 3500. Polybutadiene polyol is disclosed in JP-A-55-98220.
No. 449-450 of Japan Rubber Association Journal Vol. 45 (1972)
Page, Sealants (written by Damsis, published by Reinhold Publishing, 1967). In order to initiate and continuously polymerize the lactones, the lactones and the initiator should be mixed at a ratio of about 100 to 220
℃, preferably 160-180℃. If the temperature is too high, thermal decomposition will occur, which is not desirable. In the ring-opening polymerization, a catalyst for promoting the reaction is preferably present. As a catalyst, organic titanium compounds such as tetrabutyl titanate, tetrapropyl titanate, tetraethyl titanate, etc.
Organotin compounds such as tin octylate, dibutyltin oxide, dibutyltin laurate, stannous halides such as stannous chloride, stannous bromide, stannous iodide, etc., at 0.05 to 1000 ppm, preferably
Use 0.1-100ppm. The lactone-modified polymer obtained by the method of the present invention is a linear polymer having hydroxyl groups at both ends, and its molecular weight is usually about 1,000 to 5,000. The molecular weight can be adjusted by determining the molar ratio of the polymerization initiator and the raw material lactone. A preferred lactone-modified polymer of the present invention includes a block consisting of polybutadiene polyol;
【式】（但し、ｎは１以
上）
からなるブロツク共重合体である。
新規なラクトン重合体はポリウレタンの用途と
して熱可塑性ウレタンエラスタマー、熱硬化性ウ
レタンエラストマー、ウレタンフオーム、接着
剤、シーリング剤、塗料等に極めて有利に利用さ
れ得る。
次に実施例を挙げて本発明の説明を行なうが、
これらによつて本発明を限定するものではない。
なお、例中、部はいずれも重量部を示す。
実施例 １
攪拌機、温度系、窒素ガス導入管及びコンデン
サーのついた四ツ口セパラフラスコにポリブタジ
エンポリオール（日本曹達(株)品Ｇ−1000）を1500
部、ε−カプロラクトンを225部、テトラブチル
チタネート0.03部を仕込み170℃で５時間反応さ
せ、水酸基価（KOHmg／ｇ）65.2、酸価（KOH
mg／ｇ）0.08、粘度2160（cps／60℃）の常温液体
のラクトン重合体を得た。
未変性のポリブタジエンポリオールの水酸基価
は70.2、粘度は3900であつた。
実施例 ２
実施例１と同様の装置にポリブタジエンポリオ
ール（日本曹達(株)品Ｇ−1000）を1500部、ε−カ
プロラクトンを899部、テトラブチルチタネート
0.05部を仕込み、170℃で４時間反応させ、水酸
基価（KOHmg／ｇ）44.5、酸価（KOHmg／ｇ）
0.02、粘度1612（cps／60℃）の常温ペースト状の
ラクトン重合体を得た。
実施例 ３
実施例１と同様の装置にポリブタジエンポリオ
ール（出光石油化学(株)poly Bd Ｒ−45HT）を
2000部、ε−カプロラクトンを159部、テトラブ
チルチタネート0.04部を仕込み170℃で３時間反
応させ、水酸基価（KOHmg／ｇ）41.9、酸価
（KOHmg／ｇ）0.12、粘度1900（cps／50℃）の常
温液状のラクトン重合体を得た。
実施例 ４
実施例１と同様の装置にポリブタジエンポリオ
ール（出光石油化学(株)poly Bd Ｒ−45HT）を
2000部、ε−カプロラクトンを636部、テトラブ
チルチタネート0.05部を仕込み170℃で３時間反
応させ、水酸基価（KOHmg／ｇ）37.4、酸価
0.21、粘度2480（cps／50℃）の常温ペースト状の
ラクトン重合体を得た。It is a block copolymer consisting of the formula: (where n is 1 or more). The new lactone polymer can be extremely advantageously used in polyurethane applications such as thermoplastic urethane elastomers, thermosetting urethane elastomers, urethane foams, adhesives, sealants, and paints. Next, the present invention will be explained with reference to Examples.
The present invention is not limited to these.
In addition, in the examples, all parts indicate parts by weight. Example 1 1,500 ml of polybutadiene polyol (Nippon Soda Co., Ltd. product G-1000) was placed in a four-necked Separa flask equipped with a stirrer, temperature system, nitrogen gas inlet tube, and condenser.
225 parts of ε-caprolactone and 0.03 parts of tetrabutyl titanate were reacted at 170°C for 5 hours to obtain a hydroxyl value (KOHmg/g) of 65.2 and an acid value (KOH
A lactone polymer which was liquid at room temperature and had a viscosity of 2160 (cps/60°C) and a lactone polymer (mg/g) of 0.08 was obtained. The unmodified polybutadiene polyol had a hydroxyl value of 70.2 and a viscosity of 3900. Example 2 Into the same apparatus as in Example 1, 1500 parts of polybutadiene polyol (G-1000 manufactured by Nippon Soda Co., Ltd.), 899 parts of ε-caprolactone, and tetrabutyl titanate were added.
0.05 part was charged and reacted at 170℃ for 4 hours, hydroxyl value (KOHmg/g) 44.5, acid value (KOHmg/g)
0.02 and a viscosity of 1612 (cps/60°C), a room temperature paste-like lactone polymer was obtained. Example 3 Polybutadiene polyol (poly Bd R-45HT, manufactured by Idemitsu Petrochemical Co., Ltd.) was added to the same equipment as in Example 1.
2000 parts, ε-caprolactone 159 parts, and tetrabutyl titanate 0.04 parts were charged and reacted at 170℃ for 3 hours, hydroxyl value (KOHmg/g) 41.9, acid value (KOHmg/g) 0.12, viscosity 1900 (cps/50℃) ) was obtained as a liquid lactone polymer at room temperature. Example 4 Polybutadiene polyol (poly Bd R-45HT, manufactured by Idemitsu Petrochemical Co., Ltd.) was added to the same equipment as in Example 1.
2000 parts, 636 parts of ε-caprolactone, and 0.05 parts of tetrabutyl titanate were charged and reacted at 170℃ for 3 hours to obtain a hydroxyl value (KOHmg/g) of 37.4 and an acid value of
A lactone polymer in the form of a paste at room temperature with a viscosity of 0.21 and a viscosity of 2480 (cps/50°C) was obtained.
Claims (1)
エンポリオールを開始剤に用いてラクトン類を開
環重合させることを特徴とするラクトン重合体の
製造方法。1. A method for producing a lactone polymer, which comprises carrying out ring-opening polymerization of lactones using polybutadiene polyol as an initiator without the presence of Li in the system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58130935A JPS6023418A (en) | 1983-07-20 | 1983-07-20 | Preparation of novel lactone polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58130935A JPS6023418A (en) | 1983-07-20 | 1983-07-20 | Preparation of novel lactone polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6023418A JPS6023418A (en) | 1985-02-06 |
| JPH0456046B2 true JPH0456046B2 (en) | 1992-09-07 |
Family
ID=15046137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58130935A Granted JPS6023418A (en) | 1983-07-20 | 1983-07-20 | Preparation of novel lactone polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6023418A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0266973A3 (en) * | 1986-11-06 | 1990-01-10 | Thiokol Corporation | Pcp/htpb block copolymer and propellant binder prepared therefrom |
| JP2506363B2 (en) * | 1987-03-13 | 1996-06-12 | 株式会社クラレ | Poly-β-methyl-δ-valerolactone-based polyester polyol having a low carboxyl group content and method for producing the same |
| FR2912752B1 (en) * | 2007-02-16 | 2012-10-05 | Arkema France | PROCESS FOR PREPARING A COPOLYMER OF AT LEAST ONE CYCLIC MONOMER |
| TWI486367B (en) | 2012-05-30 | 2015-06-01 | Nippon Soda Co | Polyurethane |
| JP6145174B2 (en) * | 2013-10-24 | 2017-06-07 | 日本曹達株式会社 | Polyol composition |
| BR112017003310A2 (en) * | 2014-08-18 | 2018-01-23 | Basf Se | polyester modified polybutadienols for producing polyurethane elastomers and thermoplastic polyurethanes |
| BR112018068332B1 (en) * | 2016-03-21 | 2022-10-04 | Basf Se | CROSS-LINKED POLYURETHANE, COMPOSITE, MIXTURE, PROCESS TO PRODUCE A COMPOSITE AND USES OF CROSS-LINKED POLYURETHANE |
| EP3243863A1 (en) * | 2016-05-09 | 2017-11-15 | Evonik Degussa GmbH | Use of block copolymers in adhesives |
| CN110903805B (en) * | 2019-12-23 | 2021-10-29 | 美瑞新材料股份有限公司 | Low-polarity high-resilience polyurethane hot melt adhesive, and preparation method and application thereof |
-
1983
- 1983-07-20 JP JP58130935A patent/JPS6023418A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6023418A (en) | 1985-02-06 |
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