JPS5884808A - Preparation of resinous material - Google Patents

Preparation of resinous material

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Publication number
JPS5884808A
JPS5884808A JP18292981A JP18292981A JPS5884808A JP S5884808 A JPS5884808 A JP S5884808A JP 18292981 A JP18292981 A JP 18292981A JP 18292981 A JP18292981 A JP 18292981A JP S5884808 A JPS5884808 A JP S5884808A
Authority
JP
Japan
Prior art keywords
melt
weight ratio
melting point
resinous material
compound
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
Application number
JP18292981A
Other languages
Japanese (ja)
Other versions
JPH0224848B2 (en
Inventor
Takuo Ando
安藤 卓雄
Takeshi Matsuyama
松山 武司
Tetsuya Ooshima
哲哉 大嶋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Synthetic Chemical Industry Co Ltd
Original Assignee
Nippon Synthetic Chemical Industry Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Synthetic Chemical Industry Co Ltd filed Critical Nippon Synthetic Chemical Industry Co Ltd
Priority to JP18292981A priority Critical patent/JPS5884808A/en
Publication of JPS5884808A publication Critical patent/JPS5884808A/en
Publication of JPH0224848B2 publication Critical patent/JPH0224848B2/ja
Granted legal-status Critical Current

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  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

PURPOSE:To prepare a resinous material without causing the phase separation even on melting under heating, by copolymerizing a monomeric component consisting of an unsaturated polyfunctional carboxylic acid anhydride and another monomer in a melt of a compound having a hydroxyl group and a specific melting point. CONSTITUTION:(A) A monomeric component consisting of (i) an unsaturated carboxylic acid anhydride, e.g. maleic anhydride, and (ii) another monomer, e.g. a vinyl ester, is copolymerized in (A) a melt of a compound, e.g. a partial fatty acid ester of a polyhydric alcohol, having hydroxyl groups and <=150 deg.C melting point preferably at 1:(0.001-0.5) weight ratio between the components (A) and (i) and 1:(0.1-10) weight ratio between the components (A) and (B), and if necessary an additive, e.g. a filler, tackifier or colorant, is mixed therewith to prepare the aimed resinous material. USE:Adhesives, binders, etc.

Description

【発明の詳細な説明】 零発f!4Fi、加熱溶融しても相分離を起さない樹脂
状物質の製造法K、関するものである。
[Detailed description of the invention] Zero shot f! 4Fi, a method K for producing a resinous material that does not cause phase separation even when heated and melted.

ワックス性状を有する物質に熱可塑性重合体をブレンド
した組成物は接着剤、バインダー、その他の用途Kj6
用できるが、加熱溶融物が経時的に相分離を起すことが
実用土の問題となっていた。
Compositions made by blending wax-like substances with thermoplastic polymers can be used as adhesives, binders, and other applications Kj6
However, the problem with practical soils is that the heated molten material undergoes phase separation over time.

しかして相分離を防止する丸めにFi機械的に撹拌を行
えばよいのであるが、それでは使用上不便を免れないし
、又使用態様によっては機械的撹拌ができないことも多
い。
Although it is possible to mechanically stir Fi to prevent phase separation, this is inconvenient in use, and mechanical stirring is often not possible depending on the mode of use.

本発明はこのような従来の問題点を解決したもので、長
時間溶融状態においても相分離を起さないal−状物質
を提供することを目的とする。
The present invention solves these conventional problems and aims to provide an Al-like material that does not undergo phase separation even in a molten state for a long time.

本発明は、水酸基を有する融点150℃以下の化合物(
4)のSm液中で、不飽和多価カルボン酸無水物(bl
)及び他の七ツマ−(bりよ抄なるモノマー成分俤)を
共重合することを特徴とする。
The present invention relates to a compound having a hydroxyl group and a melting point of 150°C or less (
4) In the Sm solution, unsaturated polycarboxylic anhydride (bl
) and other nanatsumers (monomer components consisting of b riyosho) are copolymerized.

この囚の溶融液中での俤)の重合反応においては、(b
l)ri分と(b8)成分とから共重合体が得られると
共K、生成し丸糸重合体中の(bt)成分と(4)の水
酸基とのエステル化反応、共重合前の(bl)vi、分
と回申のエステル基とのエステル交換反応なども併行し
て起り、得られた反応物は複雑な化学組成になっている
ものと推定される。
In the polymerization reaction of (b) in the melt of this polymer, (b)
l) When a copolymer is obtained from the ri component and the (b8) component, co-K is produced, and the esterification reaction between the (bt) component and the hydroxyl group of (4) in the round thread polymer occurs, and the ( It is presumed that the transesterification reaction between the ester groups of bl)vi and min and the ester group also occurs in parallel, and the resulting reaction product has a complex chemical composition.

本発明の方法により得られるwitMI状物質は、因十
伽)の種類或いは(AIと俤)の比率により種々の性状
をとシうるが、典型的な場合は外観が白色不透明のワッ
クス性状をしてお艶、このものは加熱するとある温度で
溶融し、シャープなメルト挙動を示す。そしてこの物質
は長時間溶融状[Iにおいても相分離を起さないという
顕著な効果を奏する。
The witMI-like substance obtained by the method of the present invention can have various properties depending on the type of substance (injuga) or the ratio of (AI and 俤), but typically it has a waxy appearance with a white and opaque appearance. This glossy material melts at a certain temperature when heated and exhibits sharp melting behavior. This substance exhibits the remarkable effect of not causing phase separation even in the molten state [I] for a long time.

水着基を存する融点+50’C以Fの化合物(3)とし
ては、常温で固体状又は液体状のもの、なかんづ〈融点
50〜150℃でワックス性状を有するものが用いられ
、たとえば多価アル7−ルの部分子il 肪酸x xチ
ル、−価又は多価アル7− ルと水酸基を有する脂肪酸
との部分又は完全エステル、ソルピクン脂肪酸エステル
、高級アルコール、水酸基を有する油脂、ポリエステル
などがあげられる。
As the compound (3) containing a swimsuit group and having a melting point of +50°C or higher, compounds that are solid or liquid at room temperature, and among others, those that have waxy properties and a melting point of 50 to 150°C, such as polyvalent Partial molecules of al-7-yl fatty acids can give.

これらの中ではOH価20以上のI+h肪酸エステル、
OH価20以上の飽和ポリエステルが特に重要である。
Among these, I+h fatty acid esters with an OH value of 20 or more,
Particularly important are saturated polyesters with an OH value of 20 or more.

融点が150℃を越えるものけ、その溶融液中での(B
lの重合が実際上難しく、へ明の目的には不適当である
。又水酸基を有しないものは共重合〈より得られる樹脂
状物質が溶融時相分離を起すので、やはり本発明の目的
には不適当である。
If the melting point exceeds 150℃, (B
The polymerization of 1 is difficult in practice and is unsuitable for the purpose of clarity. Moreover, those having no hydroxyl group are unsuitable for the purpose of the present invention since the resinous material obtained by copolymerization causes phase separation when melted.

モノマー成分(8)を構成する不飽和多価カルボン駿無
水物(bl)としては、無水マレイン酸、無水イタコン
酸、無水シトラコン酸、無水グルタフン酸などが用いら
れる。
As the unsaturated polycarboxylic anhydride (BL) constituting the monomer component (8), maleic anhydride, itaconic anhydride, citraconic anhydride, glutafic anhydride, etc. are used.

他のモノマー(b Jとしては、ビニルエステル、不飽
和モノカルボン駿又はそのエステル・塩・アミド・ニト
リル、不飽和ジカルボン酸又社そのモノエステル・ジエ
ステル・塩、不飽和スルホン酸又はその塩、スチレン糸
上ツマ−、ビニルエーテル、塩化ビニルなどがあげられ
る。これらの中ではビニルエステル、スチレン、アクリ
ル酸エステル、メククリル酸エステルが特に重要である
。そのri カシビニルベンゼン、エチレングリフール
ジメタクリレート、ジアリルフタレートをはじめ各種の
多官能性七ツマ−を少量併用することもできる。
Other monomers (b J include vinyl ester, unsaturated monocarboxylic acid or its ester, salt, amide, nitrile, unsaturated dicarboxylic acid or its monoester, diester, salt, unsaturated sulfonic acid or its salt, styrene Examples of these include thread pickers, vinyl ethers, vinyl chloride, etc. Among these, vinyl esters, styrene, acrylic esters, and meccrylic esters are particularly important. It is also possible to use a small amount of various polyfunctional heptamers including .

零発11JIにおいては体)の溶融液中で(b、)及び
(b□)よシなる七ツマー成分俤)の共重合を行う。囚
Fi落媒としても41&能し、反応物質としても機能す
る。
In 11JI, the copolymerization of (b, ) and (b□) is carried out in the melt of (b, ) and (b□). It also functions as a filter medium and as a reactant.

共重合は通常ラジカル重合開始剤を用いて行う。Copolymerization is usually carried out using a radical polymerization initiator.

囚と@)の使用比率は広く変えうるが、(4)と(bl
)との重量比祉1 : 0.001〜0.5、好ましく
#−i1: 0.005〜0.5とするのが望ましく、
(bl)の比率が余りに小さいと得られる樹脂状物質が
加熱溶融時に相分離しやすく、一方(bJ)の比率が余
りに大きいと(b、)と(b2)の共重合反応の制御が
難しくなる。又(4)との)との重量比はI : 0.
1〜10とするのが好ましく、[有])の比率が余りに
小さいと均一性は保持できるが頭の性質が支配的で実用
性に難を生じ、一方の)の比率が余抄に大きいと重合時
及び重合終了後の系の粘度が大きくなりすぎる、反応物
は常温団体で、典型的な場合は白色又はわずかに着色し
た不透明なワックス性状を有する、。
The ratio of usage of prison and @) can vary widely, but (4) and (bl
) with weight ratio of 1: 0.001 to 0.5, preferably #-i1: 0.005 to 0.5,
If the ratio of (bl) is too small, the resulting resinous material will be likely to undergo phase separation during heating and melting, while if the ratio of (bJ) is too large, it will be difficult to control the copolymerization reaction of (b, ) and (b2). . Moreover, the weight ratio of (4) and ) is I:0.
It is preferable to set the ratio to 1 to 10. If the ratio of [Yes]) is too small, uniformity can be maintained, but the character of the head becomes dominant and practicality becomes difficult. The viscosity of the system during and after polymerization becomes too high; the reactants typically have a white or slightly colored opaque waxy appearance at room temperature.

本発明においては共重合反応時又#−1反応後に、フィ
ラー、粘着付与剤、着色剤、補強繊維、可塑剤、界面活
性剤などの各種の添加剤を適宜配合することができるし
、又他の樹脂と混合することもできる。
In the present invention, during the copolymerization reaction or after the #-1 reaction, various additives such as fillers, tackifiers, colorants, reinforcing fibers, plasticizers, surfactants, etc. can be appropriately added. It can also be mixed with other resins.

本発明の方法によ抄得られた樹脂状物質は、ホットメル
ト型接着剤、粘着剤、紙加工剤、繊維加工剤、塗料用ビ
ヒクル、インク用ビヒクル、トナー用バインダー、セラ
ミック用バイングーなどの用途に用いることができる。
The resinous material obtained by the method of the present invention can be used as hot melt adhesives, pressure-sensitive adhesives, paper processing agents, fiber processing agents, paint vehicles, ink vehicles, toner binders, ceramic binders, etc. It can be used for.

次に実施例をあげて本発明の方法をさらに説明する。Next, the method of the present invention will be further explained with reference to Examples.

実施例1 01価180〔岬KOH)、融点78℃のグリセリン七
ノステアリン酸エステル(4)500部をフラスコに仕
込んで95℃に加熱して溶融し、撹拌下に無水マレイン
酸(bl) 15部、メチルメタクリレ−) (bり 
250部及び2−エチルへキシルアクリレ−) (b’
t) 2 s 6部を加え、さらにベンゾイルパーオキ
サイド7部を加え、95〜100℃で8時間重合を行っ
た。反応終了後反応物をフラスコから取り出し、放冷し
たところ、白色不透明のワックス状のブロックを得た。
Example 1 500 parts of glycerin heptanostearate (4) with a valence of 180 [Misaki KOH] and a melting point of 78°C was charged into a flask and heated to 95°C to melt it, and while stirring, maleic anhydride (bl) 15 part, methyl methacrylate)
250 parts and 2-ethylhexyl acrylate) (b'
t) 6 parts of 2s were added, and further 7 parts of benzoyl peroxide were added, and polymerization was carried out at 95 to 100°C for 8 hours. After the reaction was completed, the reaction product was taken out from the flask and allowed to cool, yielding a white opaque waxy block.

このブロックを試験管に詰めて160℃に加熱して再溶
融し、同温度に24時間放置したが、溶融液は均一層を
保ち、相分離を起こさなかつ丸。
This block was packed into a test tube, heated to 160°C, remelted, and left at the same temperature for 24 hours, but the molten liquid remained a homogeneous layer without phase separation and was round.

対照例1 実施例1における(b、)、(bり及び(bz)をトル
エン中でベンゾイルパーオキサイドを用いて重合し、ト
ルエンを除去することにより共重合体を得た。
Comparative Example 1 (b, ), (bri) and (bz) in Example 1 were polymerized in toluene using benzoyl peroxide, and a copolymer was obtained by removing toluene.

この共重合体500都と実施例1の(A) 500部と
を150℃に加熱混合溶融してよく撹拌後、撹拌をとめ
、同温度に放置したところ、約15分で2層に相分離を
起こした。
500 parts of this copolymer and 500 parts of (A) from Example 1 were heated to 150°C, mixed and melted, and stirred well. When the stirring was stopped and the mixture was left at the same temperature, the phase separated into two layers in about 15 minutes. woke up.

対照例2 (bl)を用いなかったほかFi実施例1と同様にして
囚存在下の(b2)と(b″2)の共重合を行ったが、
得られたブロックは溶融すると約15分で2層に相分離
した。
Control Example 2 Copolymerization of (b2) and (b″2) in the presence of a prisoner was carried out in the same manner as in Fi Example 1 except that (bl) was not used.
The resulting block phase separated into two layers in about 15 minutes upon melting.

実施例2 oH価A5[5vKOH]、軟化点60℃の飽和ポリエ
ステル(3)600部をフラスコに仕込んで90℃に加
熱して溶融し、撹拌下に無水マレイン酸(bl)25部
、メチルメタクリレート(b、) 250部及びプロピ
オン駿ビニル(b6)550部を加え、さらにベンゾイ
ルパーオキサイド5部を加え、90〜110℃で8時間
重合を行った。反応終了後反応物をフラスコから取り出
し、放冷したところ、白色不透明のブロックを得た。
Example 2 600 parts of a saturated polyester (3) with an oH value of A5 [5vKOH] and a softening point of 60°C was charged into a flask and heated to 90°C to melt it, and while stirring, 25 parts of maleic anhydride (BL) and methyl methacrylate were added. (b,) 250 parts and 550 parts of propionic vinyl (b6) were added, and further 5 parts of benzoyl peroxide were added, and polymerization was carried out at 90 to 110°C for 8 hours. After the reaction was completed, the reaction product was taken out from the flask and allowed to cool, yielding a white opaque block.

このブロックを試験管に詰めて130℃に加熱して再溶
融し、同泥度に24時t#fi放置したが、溶融#は均
一層を保ち、相分離を起こさなかった一1対照例6 実施例2における(bり、(b=)及び(鴫)をトルエ
ン中中でベンゾイルパーオキサイドを用いて重合し、ト
ルエンを除去することにより共重合体を得だ。
This block was packed into a test tube, heated to 130°C, remelted, and left at the same muddy temperature for 24 hours, but the molten # maintained a uniform layer and no phase separation occurred.11 Control Example 6 A copolymer was obtained by polymerizing (bri, (b=), and (b) in Example 2 using benzoyl peroxide in toluene, and removing toluene.

この共重合体600部と実施例2の(A1600部とを
150℃に加熱混合溶融してよく撹拌後、撹拌をとめ、
同温度に放置したところ、約15IIjで2′層に相分
離を起こした。
600 parts of this copolymer and 1600 parts of (A) of Example 2 were mixed and melted by heating to 150°C, and after stirring well, the stirring was stopped,
When left at the same temperature, phase separation occurred into the 2' layer at about 15 IIj.

対照例4 (b、)を用いなかったほかは実施例1と同様にして囚
存在下の(−)と(Qの共重合を行ったが、得られたブ
ロックは溶融すると約15分で2層に相分離した。
Control Example 4 Copolymerization of (-) and (Q) in the presence of a prisoner was carried out in the same manner as in Example 1 except that (b,) was not used. The layers separated.

実施例3 oH価160〔■KO1()、融点84℃のグリセリン
トリ12−とドロキシステアリン酸エステル(水添硬化
ヒマシ油)(A1500部を7クスコに仕込んで95℃
に加熱して溶融し、撹拌下に無水イタコン酸(b、) 
20部、スチレン(bz) 550部及び1】−ブチル
アクリレート(t4+ + 50部を加え、さらにベン
ゾイルパーオキサイド15部を加え、90〜110℃で
8時間重合を行った。反応路r後反応物をフラスコから
収り出し、放冷したところ、白色不透明のワックス状の
ブロックを得た。
Example 3 Glycerin tri-12- and droxystearate (hydrogenated hydrogenated castor oil) with oH value 160 [■KO1(), melting point 84°C] (1500 parts of A were charged in 7 Cusco and heated to 95°C)
Melt itaconic anhydride (b,) under stirring by heating to
20 parts, 550 parts of styrene (bz) and 50 parts of 1]-butyl acrylate (t4+) were added, and further 15 parts of benzoyl peroxide was added, and polymerization was carried out at 90 to 110°C for 8 hours. Reactant after reaction route r When the mixture was removed from the flask and allowed to cool, a white opaque waxy block was obtained.

このブロックを試験管に詰めて1′50℃に加熱して再
溶融し、同温度に24時間放置したが、溶融液は均一層
を保ち、相分離を起こさなかった。
This block was packed into a test tube, heated to 1'50°C, remelted, and left at the same temperature for 24 hours, but the molten liquid remained a uniform layer and no phase separation occurred.

Claims (1)

【特許請求の範囲】 1、 水酸基を有する融点150℃以下の化合物囚の溶
融液中で、不飽和多価カルポジ酸無水物(bl)及び他
の七ツマ−(b、)よりなるモノマー成分俤)を共重合
することを特徴とする樹脂状物質のIll泳法 L に)と(bl)との重量比が1 : 0.001〜
0.5である特許請求の範囲第1項記載の方法。 &(A)と(2)との重量比が1 : 0.1〜10で
ある特許請求の範囲181項記載の方法。 4、  (A)がワックス性状を示す化合物である特許
請求のIIInt項記載の方法。 5、 ワックス性状を示す化合物がOH価20以上の脂
肪酸エステルである特許請求の範囲第4項記載の方法。 6 ワックス性状を示す化合物がOH価20以上の飽和
ポリエステルである特許請求の範囲第4項記載の方法1
. 7、  (bt)が無水マレイン酸である特許請求の範
囲第1項記載の方法。 a、  (bt)が無水イタ1ン駿である特許請求の範
囲第1項記載の方法。
[Scope of Claims] 1. In a melt of a compound having a hydroxyl group and a melting point of 150°C or less, a monomer component consisting of unsaturated polycarpodic acid anhydride (bl) and other heptamers (b) ) and (bl) have a weight ratio of 1:0.001 to
0.5. 182. The method according to claim 181, wherein the weight ratio of &(A) and (2) is 1:0.1-10. 4. The method according to claim IIInt, wherein (A) is a compound exhibiting waxy properties. 5. The method according to claim 4, wherein the compound exhibiting wax properties is a fatty acid ester having an OH value of 20 or more. 6. Method 1 according to claim 4, wherein the compound exhibiting wax properties is a saturated polyester having an OH value of 20 or more.
.. 7. The method according to claim 1, wherein (bt) is maleic anhydride. 2. The method according to claim 1, wherein a and (bt) are anhydrous italic acid.
JP18292981A 1981-11-13 1981-11-13 Preparation of resinous material Granted JPS5884808A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP18292981A JPS5884808A (en) 1981-11-13 1981-11-13 Preparation of resinous material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP18292981A JPS5884808A (en) 1981-11-13 1981-11-13 Preparation of resinous material

Publications (2)

Publication Number Publication Date
JPS5884808A true JPS5884808A (en) 1983-05-21
JPH0224848B2 JPH0224848B2 (en) 1990-05-30

Family

ID=16126838

Family Applications (1)

Application Number Title Priority Date Filing Date
JP18292981A Granted JPS5884808A (en) 1981-11-13 1981-11-13 Preparation of resinous material

Country Status (1)

Country Link
JP (1) JPS5884808A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60223810A (en) * 1984-04-20 1985-11-08 Goou Kagaku Kogyo Kk Production of molding binder composition
US8317438B2 (en) 2006-10-13 2012-11-27 Kennametal Inc. Twist drill having at least two cutting inserts at the tip each with its own J-shaped chip guiding flute and a method for the production thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8850980B2 (en) 2006-04-03 2014-10-07 Canon Nanotechnologies, Inc. Tessellated patterns in imprint lithography

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60223810A (en) * 1984-04-20 1985-11-08 Goou Kagaku Kogyo Kk Production of molding binder composition
US8317438B2 (en) 2006-10-13 2012-11-27 Kennametal Inc. Twist drill having at least two cutting inserts at the tip each with its own J-shaped chip guiding flute and a method for the production thereof
US8668409B2 (en) 2006-10-13 2014-03-11 Kennametal Inc. Twist drill and method for the production thereof

Also Published As

Publication number Publication date
JPH0224848B2 (en) 1990-05-30

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