JP2001323043A - Method for producing plasticizer for polyurethane resin - Google Patents
Method for producing plasticizer for polyurethane resinInfo
- Publication number
- JP2001323043A JP2001323043A JP2000146991A JP2000146991A JP2001323043A JP 2001323043 A JP2001323043 A JP 2001323043A JP 2000146991 A JP2000146991 A JP 2000146991A JP 2000146991 A JP2000146991 A JP 2000146991A JP 2001323043 A JP2001323043 A JP 2001323043A
- Authority
- JP
- Japan
- Prior art keywords
- plasticizer
- group
- polyurethane resin
- present
- 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.)
- Pending
Links
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ポリウレタン樹脂
に対する相溶性が優れた可塑剤の製造方法に関する。[0001] The present invention relates to a method for producing a plasticizer having excellent compatibility with a polyurethane resin.
【０００２】[0002]
【従来の技術】従来、ポリウレタン樹脂用可塑剤は、フ
タル酸エステル系、アジピン酸エステル系、リン酸エス
テル系等が知られていた。2. Description of the Related Art Heretofore, as a plasticizer for a polyurethane resin, a phthalate ester type, an adipic ester type, a phosphate ester type and the like have been known.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、従来の
可塑剤にはポリウレタン樹脂との相溶性が悪く、加熱す
ると可塑剤が樹脂の表面に染み出てくる（ブリード）と
いう問題があった。本発明は、このブリードを改良し、
相溶性の優れた、ブリードしない可塑剤を提供すること
を目的とする。However, the conventional plasticizer has poor compatibility with the polyurethane resin, and there is a problem that the plasticizer exudes (bleeds) to the surface of the resin when heated. The present invention improves this bleed,
An object of the present invention is to provide a plasticizer which has excellent compatibility and does not bleed.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、このよう
な従来の問題点を解決するため鋭意検討した結果、ある
特定の化合物が優れた相溶性を有することを見い出し、
本発明を完成するに至った。Means for Solving the Problems The present inventors have conducted intensive studies to solve such conventional problems, and as a result, have found that a specific compound has excellent compatibility.
The present invention has been completed.
【０００５】すなわち、本発明により、アルコキシポリ
アルキレングリコールとジイソシアネート化合物を、Ｎ
ＣＯ基とＯＨ基のモル比が１．０〜１．５になるように
配合し、反応して得られる相溶性の優れたポリウレタン
樹脂用可塑剤の製造方法が提供される。That is, according to the present invention, an alkoxypolyalkylene glycol and a diisocyanate compound are
A method for producing a plasticizer for a polyurethane resin having excellent compatibility obtained by mixing and reacting the molar ratio of a CO group and an OH group to be 1.0 to 1.5 is provided.
【０００６】[0006]
【発明の実施の形態】本発明に用いられるアルコキシポ
リアルキレングリコールは、化学式（１）に示したもの
である。BEST MODE FOR CARRYING OUT THE INVENTION The alkoxypolyalkylene glycol used in the present invention is represented by the formula (1).
【０００７】[0007]
【化１】 Embedded image
【０００８】ここで、化学式（１）は、ランダム共重合
体又はブロック共重合体を示し、Ｒは、メチル、エチ
ル、プロピルのようなアルキル基、あるいはアリル基、
あるいはアリール基を示す。Ｒ1は、エチル基を示し、
Ｒ2は、プロピル基、ブチル基等のエチル基以外の基を
示す。ｍは１〜５０、ｎは０〜２０の整数を示す。ま
た、本発明は、化学式（１）以外の分子内に１個の活性
水素基を持った化合物を必要に応じて併用することがで
きる。Here, chemical formula (1) represents a random copolymer or a block copolymer, and R represents an alkyl group such as methyl, ethyl, propyl, or an allyl group;
Alternatively, it represents an aryl group. R 1 represents an ethyl group,
R 2 represents a group other than an ethyl group such as a propyl group and a butyl group. m represents an integer of 1 to 50 and n represents an integer of 0 to 20. Further, in the present invention, a compound having one active hydrogen group in a molecule other than the chemical formula (1) can be used in combination, if necessary.
【０００９】アルコキシポリアルキレングリコールの好
適な例として、数平均分子量２００から２，０００のメ
トキシポリエチレングリコールを挙げることができる。Preferred examples of the alkoxypolyalkylene glycol include methoxypolyethylene glycol having a number average molecular weight of 200 to 2,000.
【００１０】本発明に用いられるジイソシアネート化合
物は、フェニレンジイソシアネート、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、テトラメチル
キシレンジイソシアネート、ナフチレンジイソシアネー
ト、ジフェニルメタンジイソシアネート等及びこれら異
性体からなる芳香族系ジイソシアネート、１，６−ヘキ
サメチレンジイソシアネート、テトラメチルヘキサメチ
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、シクロヘキサンジ
イソシアネート、イソホロンジイソシアネート、水添ジ
フェニルメタンジイソシアネート等の脂環式ジイソシア
ネート等を挙げることができる。また、これらの化合物
と活性水素基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、あるいは、これらの化合物の反応、例え
ばカルボジイミド化反応によるイソシアネート変性体等
も挙げることができる。また、メタノール、n-ブタノー
ル、ベンジルアルコール、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、クレゾール等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等も挙げ
ることができる。The diisocyanate compound used in the present invention includes phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, tetramethyl xylene diisocyanate, naphthylene diisocyanate, diphenylmethane diisocyanate, and aromatic diisocyanates comprising these isomers. Examples thereof include aliphatic diisocyanates such as hexamethylene diisocyanate, tetramethylhexamethylene diisocyanate, and 1,12-dodecane diisocyanate; alicyclic diisocyanates such as cyclohexane diisocyanate, isophorone diisocyanate, and hydrogenated diphenylmethane diisocyanate. Further, an isocyanate group-terminated compound obtained by the reaction of these compounds with an active hydrogen group-containing compound, or an isocyanate-modified compound obtained by the reaction of these compounds, for example, a carbodiimidation reaction can also be used. Further, a polyisocyanate partially stabilized with a blocking agent having one active hydrogen in a molecule such as methanol, n-butanol, benzyl alcohol, ethyl acetoacetate, ε-caprolactam, methyl ethyl ketone oxime, phenol, and cresol is also included. be able to.
【００１１】本発明において、アルコキシポリアルキレ
ングリコールとジイソシアネート化合物の配合比は、ジ
イソシアネート化合物中のＮＣＯ基とアルコキシポリア
ルキレングリコール中のＯＨ基のモル比が１．０〜１．
５になるようにする。モル比が１．０未満の場合、本発
明の可塑剤の中に未反応のアルコキシポリアルキレング
リコールが残り、ブリードに悪影響を与え、また、モル
比が１．５を超える場合、可塑剤が増粘したり、あるい
はポリウレタン樹脂との相溶性が悪化する等で好ましく
ない。特に好ましいモル比は、１．０１〜１．３０であ
る。In the present invention, the molar ratio of the NCO groups in the diisocyanate compound to the OH groups in the alkoxypolyalkylene glycol is 1.0 to 1.
Make it 5 When the molar ratio is less than 1.0, unreacted alkoxypolyalkylene glycol remains in the plasticizer of the present invention and adversely affects the bleed, and when the molar ratio exceeds 1.5, the plasticizer increases. It is not preferable because it sticks or the compatibility with the polyurethane resin deteriorates. A particularly preferred molar ratio is 1.01 to 1.30.
【００１２】本発明の配合比は、ＮＣＯ基過剰の配合で
あり、過剰のＮＣＯ基は、加熱及び、又は触媒によりア
ロファネート化等の反応をさせることを特徴とする。本
発明の可塑剤には残ＮＣＯ基は通常ないが、必要に応じ
ＮＣＯ基を残し、反応性可塑剤とすることができる。The compounding ratio of the present invention is a compounding ratio in which the NCO group is excessive, and the excess NCO group is characterized by causing a reaction such as allophanation by heating and / or a catalyst. The plasticizer of the present invention does not usually have a residual NCO group, but can leave a NCO group as needed to be a reactive plasticizer.
【００１３】本発明によって得られるポリウレタン樹脂
用可塑剤は、アルコキシポリアルキレングリコールとジ
イソシアネート化合物の反応によって得られる。この反
応は、通常のＯＨ基とＮＣＯ基の反応と同様にして行う
ことができる。例えば、反応温度は、６０〜１４０℃、
時間は１〜１０時間程度である。本反応は必要に応じ、
触媒を用いることができる。触媒としては、通常のウレ
タン化触媒、アロファネート化触媒等が用いられ、例え
ば、トリエチレンジアミン、ビス−２−ジメチルアミノ
エチルエーテル、ジブチルチンジラウレート、ナフテン
酸鉛、ナフテン酸鉄、オクテン酸銅等を挙げることがで
きる。The plasticizer for a polyurethane resin obtained by the present invention is obtained by reacting an alkoxypolyalkylene glycol with a diisocyanate compound. This reaction can be carried out in the same manner as a usual reaction between an OH group and an NCO group. For example, the reaction temperature is 60 to 140 ° C,
The time is about 1 to 10 hours. This reaction is performed as necessary.
A catalyst can be used. As the catalyst, a usual urethanization catalyst, allophanation catalyst or the like is used, and examples thereof include triethylenediamine, bis-2-dimethylaminoethyl ether, dibutyltin dilaurate, lead naphthenate, iron naphthenate, and copper octenoate. be able to.
【００１４】本発明における反応装置は、通常のウレタ
ン化反応に用いる反応装置を全て用いることができる。As the reactor in the present invention, all reactors used for ordinary urethanization reaction can be used.
【００１５】本発明によって得られる可塑剤は、ポリウ
レタン樹脂に対して１〜３０質量％添加して使用するこ
とができる。添加する方法は、ポリウレタン樹脂製造時
にあらかじめ原料に混合しておく方法、樹脂製造後混合
する方法等が挙げることができる。The plasticizer obtained according to the present invention can be used in an amount of 1 to 30% by mass relative to the polyurethane resin. Examples of the method of addition include a method of preliminarily mixing the raw materials during the production of the polyurethane resin, and a method of mixing after the production of the resin.
【００１６】本発明によって得られる可塑剤は、必要に
応じて他の物質、例えば酸化防止剤、紫外線吸収剤、耐
熱性向上剤、着色剤、無機及び有機充填剤、その他の可
塑剤、滑剤、帯電防止剤、補強材、架橋剤等を添加する
ことができる。The plasticizer obtained according to the present invention may contain, if necessary, other substances such as antioxidants, ultraviolet absorbers, heat resistance improvers, coloring agents, inorganic and organic fillers, other plasticizers, lubricants, An antistatic agent, a reinforcing material, a crosslinking agent, and the like can be added.
【００１７】[0017]
【実施例】本発明について、実施例及び比較例により更
に詳細に説明するが、本発明はこれらにより何ら限定さ
れるものではない。実施例及び比較例において、「部」
は全て「質量部」を意味し、「％」は全て「質量％」を
意味する。EXAMPLES The present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. In Examples and Comparative Examples,
Means “parts by mass”, and “%” means “% by mass”.
【００１８】実施例１ 錨型攪拌棒付き攪拌機、温度計、窒素ガス導入口等を付
けた４つ口フラスコに、数平均分子量４００のメトキシ
ポリエチレングリコールを８００部及びヘキサメチレン
ジイソシアネート（ＨＤＩ）を１７３部（ＮＣＯ／ＯＨ
モル比＝１．０３）仕込み、８０℃、２時間反応させた
後、ジブチルチンジラウレート（ＤＢＴＤＬ）を０．０
５部添加し、１２０℃で３時間反応させて、粘稠性液体
の可塑剤１を得た。この可塑剤のＮＣＯ含量を測定した
結果、０．１％であった。Example 1 In a four-necked flask equipped with a stirrer equipped with an anchor-type stirring bar, a thermometer, a nitrogen gas inlet and the like, 800 parts of methoxypolyethylene glycol having a number average molecular weight of 400 and 173 of hexamethylene diisocyanate (HDI) were added. Part (NCO / OH
(Molar ratio = 1.03) After charging and reacting at 80 ° C for 2 hours, dibutyltin dilaurate (DBTDL) was added at 0.0
Five parts were added and reacted at 120 ° C. for 3 hours to obtain a viscous liquid plasticizer 1. As a result of measuring the NCO content of this plasticizer, it was 0.1%.
【００１９】実施例２ 実施例１と同様なフラスコに、数平均分子量７００のメ
トキシポリエチレングリコールを７００部、メトキシト
リプロピレングリコールを２０６部、イソホロンジイソ
シアネートを２３５部（ＮＣＯ／ＯＨモル比＝１．０
５）及びＤＢＴＤＬを０．１部仕込み、８０℃、３時間
反応させ、更に１２０℃、３時間反応させて、粘稠性液
体の可塑剤２を得た。この可塑剤のＮＣＯ含量を測定し
た結果、０．１％であった。Example 2 In a flask similar to that in Example 1, 700 parts of methoxypolyethylene glycol having a number average molecular weight of 700, 206 parts of methoxytripropylene glycol and 235 parts of isophorone diisocyanate (NCO / OH molar ratio = 1.0)
5) and 0.1 part of DBTDL were charged and reacted at 80 ° C. for 3 hours, and further reacted at 120 ° C. for 3 hours to obtain a viscous liquid plasticizer 2. As a result of measuring the NCO content of this plasticizer, it was 0.1%.
【００２０】実施例３ 実施例１と同様なフラスコに、数平均分子量４００のメ
トキシポリエチレングリコールを８００部及び水添ジフ
ェニルメタンジイソシアネート（水添ＭＤＩ）を３１０
部（ＮＣＯ／ＯＨモル比＝１．２０）仕込み、８０℃、
４時間反応させ、更に１２０℃、４時間反応させて、粘
稠性液体の可塑剤３を得た。この可塑剤のＮＣＯ含量を
測定した結果、０．７％であった。Example 3 In a flask similar to that in Example 1, 800 parts of methoxypolyethylene glycol having a number average molecular weight of 400 and 310 parts of hydrogenated diphenylmethane diisocyanate (hydrogenated MDI) were added.
Parts (NCO / OH molar ratio = 1.20), 80 ° C.
The mixture was reacted for 4 hours, and further reacted at 120 ° C. for 4 hours to obtain a plasticizer 3 as a viscous liquid. As a result of measuring the NCO content of this plasticizer, it was 0.7%.
【００２１】実施例４ 実施例１と同様なフラスコに、数平均分子量５００のメ
トキシポリエチレンポリプロピレン（ＥＯ／ＰＯ＝約２
／３モル比）を１，０００部、ＨＤＩを１７１部（ＮＣ
Ｏ／ＯＨモル比＝１．０２）及びＤＢＴＤＬを０．０５
部仕込み、８０℃、２時間、更に１２０℃、３時間反応
させた。ＩＲスペクトルでＮＣＯ基の吸収がないことを
確認し、粘稠性液体の可塑剤４を得た。Example 4 A methoxypolyethylene polypropylene having a number average molecular weight of 500 (EO / PO = about 2) was placed in the same flask as in Example 1.
/ 3 mole ratio), 1,000 parts, HDI 171 parts (NC
O / OH molar ratio = 1.02) and DBTDL at 0.05
The reaction was carried out at 80 ° C. for 2 hours, and further at 120 ° C. for 3 hours. It was confirmed by the IR spectrum that there was no absorption of NCO groups, and a viscous liquid plasticizer 4 was obtained.
【００２２】応用実施例及び応用比較例 攪拌装置の付いた反応器に、８０℃に加温した数平均分
子量２，０００のブチレンアジペートジオールを２，０
００部、実施例１〜４の可塑剤及びジオクチルフタレー
ト（ＤＯＰ、比較例として）を１５５部（ポリウレタン
中の５％）、１，４−ブタンジオールを２７０部、ＤＢ
ＴＤＬを０．０９部及びＨＤＩを６７２部仕込み、混合
攪拌する。粘度が上昇し始めた時点でバットに移し、１
２０℃、３０分で後硬化させる。室温７日放置後、粉砕
し、射出成型機で３ｍｍ厚のシートを作成した。これら
のシート１００×１００×３ｍｍを１１５℃の乾燥機に
５時間入れた後、室温に戻しシートの表面の可塑剤のブ
リード状態を観察した。その結果を表１に示す。Application Examples and Application Comparative Examples In a reactor equipped with a stirrer, butylene adipate diol having a number average molecular weight of 2,000 heated to 80 ° C. was added in an amount of 2,000 to 2,000.
00 parts, 155 parts (5% in polyurethane) of plasticizer and dioctyl phthalate (DOP, as a comparative example) of Examples 1 to 4, 270 parts of 1,4-butanediol, DB
0.09 parts of TDL and 672 parts of HDI are charged and mixed and stirred. When the viscosity starts to increase, transfer to
Post-curing at 20 ° C. for 30 minutes. After being left at room temperature for 7 days, the mixture was pulverized, and a sheet having a thickness of 3 mm was formed using an injection molding machine. After placing these sheets 100 × 100 × 3 mm in a dryer at 115 ° C. for 5 hours, they were returned to room temperature and the bleeding state of the plasticizer on the surface of the sheets was observed. Table 1 shows the results.
【００２３】[0023]
【表１】 [Table 1]
【００２４】[0024]
【発明の効果】本発明の可塑剤は、ポリウレタン樹脂と
の相溶性が優れているので、可塑剤の目的であるポリウ
レタン樹脂の軟質化、可撓性化、ドレープ性化等の性質
をポリウレタン樹脂に付与することができ、また、それ
らの性質を長期に持続させることができる。また、本発
明の可塑剤の組成の一つであるアルコキシポリアルキレ
ングリコールの種類によっては、上記性質の他に親水
性、吸水性、吸湿性、帯電防止性等を付与することがで
きる。本発明の可塑剤は、塗料、接着剤、硬質フォー
ム、軟質フォーム、バインダー、熱硬化性成形用樹脂、
熱可塑性成形用樹脂等に使われるポリウレタンに添加し
て使用することができる。また、ポリウレタン樹脂以外
の樹脂、例えば、ビニール樹脂、アクリル樹脂、ポリエ
ステル樹脂、アミド樹脂、エポキシ樹脂、フェノール樹
脂、カーボネート樹脂等にも有効に利用することができ
る。The plasticizer of the present invention has excellent compatibility with the polyurethane resin. Therefore, the properties of the plasticizer, such as softening, flexibility, drapability, etc., of the polyurethane resin are improved. And their properties can be maintained for a long period of time. In addition, depending on the type of the alkoxypolyalkylene glycol, which is one of the compositions of the plasticizer of the present invention, hydrophilicity, water absorption, moisture absorption, antistatic properties, and the like can be imparted in addition to the above properties. The plasticizer of the present invention is a paint, an adhesive, a rigid foam, a flexible foam, a binder, a thermosetting resin,
It can be used by adding to polyurethane used for thermoplastic molding resins and the like. Further, it can be effectively used for resins other than polyurethane resins, for example, vinyl resins, acrylic resins, polyester resins, amide resins, epoxy resins, phenol resins, carbonate resins, and the like.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 4J002 CK021 CK042 4J034 AA01 BA02 BA03 CA02 CB01 DA01 DB01 DG03 DG04 DG05 DG10 DG12 DQ05 HA01 HA07 HA11 HC03 HC12 HC13 HC16 HC22 HC64 HD02 HD04 HD05 HD09 JA01 KA01 KB02 KD02 KE02 QA03 QC10 RA17 SA02 SB03 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4J002 CK021 CK042 4J034 AA01 BA02 BA03 CA02 CB01 DA01 DB01 DG03 DG04 DG05 DG10 DG12 DQ05 HA01 HA07 HA11 HC03 HC12 HC13 HC16 HC22 HC64 HD02 HD04 HD05 HD09 JA01 KA01 KB02 KD01 SA02 SB03
Claims (1)
ジイソシアネート化合物を、ＮＣＯ基とＯＨ基のモル比
が１．０〜１．５になるように配合し、反応して得られ
る相溶性の優れたポリウレタン樹脂用可塑剤の製造方
法。1. A highly compatible polyurethane resin obtained by blending an alkoxypolyalkylene glycol and a diisocyanate compound in a molar ratio of NCO group to OH group of 1.0 to 1.5 and reacting them. Production method of plasticizer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000146991A JP2001323043A (en) | 2000-05-18 | 2000-05-18 | Method for producing plasticizer for polyurethane resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000146991A JP2001323043A (en) | 2000-05-18 | 2000-05-18 | Method for producing plasticizer for polyurethane resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001323043A true JP2001323043A (en) | 2001-11-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2000146991A Pending JP2001323043A (en) | 2000-05-18 | 2000-05-18 | Method for producing plasticizer for polyurethane resin |
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| JP (1) | JP2001323043A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006010542A1 (en) | 2004-07-26 | 2006-02-02 | Basf Aktiengesellschaft | Thermoplastic polyurethanes containing plasticizer |
| WO2009109600A1 (en) * | 2008-03-07 | 2009-09-11 | Huntsman International Llc | Foamed materials comprising a matrix having a high hardblock content and process for preparing them |
-
2000
- 2000-05-18 JP JP2000146991A patent/JP2001323043A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006010542A1 (en) | 2004-07-26 | 2006-02-02 | Basf Aktiengesellschaft | Thermoplastic polyurethanes containing plasticizer |
| WO2009109600A1 (en) * | 2008-03-07 | 2009-09-11 | Huntsman International Llc | Foamed materials comprising a matrix having a high hardblock content and process for preparing them |
| RU2461581C2 (en) * | 2008-03-07 | 2012-09-20 | Хантсмэн Интернэшнл Ллс | Foamed materials containing matrix with high content of rigid blocks and method of producing said materials |
| US8349908B2 (en) | 2008-03-07 | 2013-01-08 | Huntsman International Llc | Foamed materials comprising a matrix having a high highblock content and process for preparing them |
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