JP2021123623A - Crosslinking composition - Google Patents
Crosslinking composition Download PDFInfo
- Publication number
- JP2021123623A JP2021123623A JP2020016283A JP2020016283A JP2021123623A JP 2021123623 A JP2021123623 A JP 2021123623A JP 2020016283 A JP2020016283 A JP 2020016283A JP 2020016283 A JP2020016283 A JP 2020016283A JP 2021123623 A JP2021123623 A JP 2021123623A
- Authority
- JP
- Japan
- Prior art keywords
- cross
- mass
- linking
- structural unit
- unit derived
- 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
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- 239000000463 material Substances 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002896 organic halogen compounds Chemical class 0.000 claims description 2
- 238000003795 desorption Methods 0.000 abstract 1
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- 238000000034 method Methods 0.000 description 21
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- 230000000052 comparative effect Effects 0.000 description 11
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- 239000003505 polymerization initiator Substances 0.000 description 10
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- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
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- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明は架橋用組成物に関し、さらに詳しくは幅広い架橋温度において、優れた架橋特性と常態物性に優れた架橋材料の提供を可能とする架橋用組成物であり、特に低温における優れた架橋特性と架橋時の常態物性に優れた架橋材料の提供を可能とする。 The present invention relates to a cross-linking composition, and more specifically, a cross-linking composition capable of providing a cross-linking material having excellent cross-linking properties and normal physical characteristics at a wide range of cross-linking temperatures, and particularly having excellent cross-linking properties at low temperatures. It is possible to provide a cross-linked material having excellent normal physical properties at the time of cross-linking.
一般にエラストマーを最終的なゴム製品として使用するためには架橋操作という煩雑な操作が必要になる。これらの煩雑な架橋操作を避けるために最近ではエラストマー性共重合体自体に反応性基を持たせることが有効な手法として開発されてきた。 Generally, in order to use an elastomer as a final rubber product, a complicated operation called a cross-linking operation is required. Recently, in order to avoid these complicated cross-linking operations, it has been developed as an effective method to give the elastomeric copolymer itself a reactive group.
エラストマー性共重合体に反応性基を持たせた例としてはアクリル酸エステルを共重合させたアクリル系エラストマーが挙げられ、反応性基としては活性塩素基やエポキシ基、カルボキシル基などが公知である。 Examples of the elastomeric copolymer having a reactive group include an acrylic elastomer copolymerized with an acrylic acid ester, and active chlorine groups, epoxy groups, carboxyl groups and the like are known as reactive groups. ..
しかしながら、アクリル系エラストマーにおいても特許文献1や特許文献2に見られるように高温下の1次架橋のみならず長時間の2次架橋を必要としており、効率的なゴム製品を製造させるためには更なる温和な条件での架橋操作が求められる。 However, as seen in Patent Document 1 and Patent Document 2, acrylic elastomers also require not only primary cross-linking at high temperature but also secondary cross-linking for a long time, and in order to produce an efficient rubber product, it is necessary. Cross-linking operation under more mild conditions is required.
高温下の架橋のみならず、比較的低温における架橋を可能とする、即ち幅広い架橋温度において対応可能な架橋用組成物を提供することを課題とする。 An object of the present invention is to provide a cross-linking composition capable of not only cross-linking at a high temperature but also at a relatively low temperature, that is, capable of cross-linking in a wide range of cross-linking temperatures.
本発明者等は鋭意検討した結果、マレイミドに由来する構成単位を有する重合体を分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物により架橋せしめることにより、課題を解決することができる。 As a result of diligent studies, the present inventors have solved the problem by cross-linking a polymer having a structural unit derived from maleimide with a polyfunctional organic compound containing at least two or more leaving groups in the molecule. Can be done.
本発明の態様は次のとおりである。
項1 マレイミドに由来する構成単位を有する重合体、及び分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物を含有する架橋用組成物。
項2 分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物が分子内に2個のハロゲン原子を含む有機ハロゲン化合物である項1に記載の架橋用組成物。
項3 分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物が分子内に2個のスルホニル基を含む有機化合物であることを特徴とする項1に記載の架橋用組成物。
項4 マレイミドに由来する構成単位を有する重合体が(メタ)アクリル酸アルキルエステルに由来する構成単位、及び/又は(メタ)アクリル酸アルコキシアルキルエステルに由来する構成単位を含有する項1〜3いずれかに記載の架橋用組成物。
項5 項1〜4いずれかに記載の架橋用組成物より作製される架橋材料。
Aspects of the present invention are as follows.
Item 1 A cross-linking composition containing a polymer having a structural unit derived from maleimide and a polyfunctional organic compound containing at least two or more leaving groups in the molecule.
Item 2. The cross-linking composition according to Item 1, wherein the polyfunctional organic compound containing at least two or more leaving groups in the molecule is an organic halogen compound containing two halogen atoms in the molecule.
Item 3. The cross-linking composition according to Item 1, wherein the polyfunctional organic compound containing at least two or more leaving groups in the molecule is an organic compound containing two sulfonyl groups in the molecule.
Item 4 Any of Items 1 to 3 in which the polymer having a structural unit derived from maleimide contains a structural unit derived from a (meth) acrylic acid alkyl ester and / or a structural unit derived from a (meth) acrylic acid alkoxyalkyl ester. The cross-linking composition described in Crab.
Item 5. A cross-linking material produced from the cross-linking composition according to any one of Items 1 to 4.
本発明の架橋用組成物は、高温下の架橋のみならず、比較的低温における架橋を可能とする幅広い架橋温度において対応可能であり、特に低温時の常態物性に優れることからこれまでゴム材料として製造されているエンジンガスケット、オイルホース、エアホース、Oリングなどの工業用ゴム材料や自動車用ゴム材料をこれまでより効率的にかつ低エネルギーで工業生産することが可能になる。 The cross-linking composition of the present invention can be used not only for cross-linking at high temperatures but also for a wide range of cross-linking temperatures that enable cross-linking at relatively low temperatures, and is particularly excellent in normal physical properties at low temperatures. It will be possible to industrially produce industrial rubber materials such as engine gaskets, oil hoses, air hoses, and O-rings, and rubber materials for automobiles that are manufactured more efficiently and with lower energy than before.
本発明はマレイミドに由来する構成単位を有する重合体、及び分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物を含有する架橋用組成物、及び架橋用組成物より作製される架橋材料である。 The present invention is made from a cross-linking composition containing a polymer having a structural unit derived from maleimide, a polyfunctional organic compound containing at least two or more leaving groups in the molecule, and a cross-linking composition. It is a cross-linking material.
マレイミドに由来する構成単位を有する重合体の全構成単位において、マレイミドに由来する構成単位の含有量は、下限は0.1質量%以上であることが好ましく、0.2質量%以上であることがより好ましく、0.3質量%以上であることが特に好ましく、上限は10質量%以下であることが好ましく、5質量%以下であることがより好ましく、2.5質量%以下であることが特に好ましい。 In all the structural units of the polymer having the structural unit derived from maleimide, the content of the structural unit derived from maleimide is preferably 0.1% by mass or more, preferably 0.2% by mass or more. Is more preferably 0.3% by mass or more, the upper limit is preferably 10% by mass or less, more preferably 5% by mass or less, and 2.5% by mass or less. Especially preferable.
本発明のマレイミドに由来する構成単位を有する重合体において、他の重合成分としては一般的にラジカル重合で製造可能なモノマーを構成単位として含有することができる。具体的には(メタ)アクリル酸エステルに由来する構成単位を例示することができる。尚、「(メタ)アクリル酸エステル」とは、「アクリル酸エステル、又はメタクリル酸エステル」を意味し、本願において、類する表現についても同様である。 In the polymer having a structural unit derived from maleimide of the present invention, as another polymerization component, a monomer that can be generally produced by radical polymerization can be contained as a structural unit. Specifically, a structural unit derived from (meth) acrylic acid ester can be exemplified. The term "(meth) acrylic acid ester" means "acrylic acid ester or methacrylic acid ester", and the same applies to similar expressions in the present application.
(メタ)アクリル酸エステルに由来する構成単位としては、(メタ)アクリル酸アルキルエステルに由来する構成単位及び/又は(メタ)アクリル酸アルコキシアルキルエステルに由来する構成単位を例示することができ、炭素数1〜8のアルキル基を有する(メタ)アクリル酸アルキルエステルに由来する構成単位、炭素数2〜8のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステルに由来する構成単位であることが好ましく、炭素数2〜6のアルキル基を有する(メタ)アクリル酸アルキルエステルに由来する構成単位及び/又は炭素数2〜6のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステルに由来する構成単位を有することがより好ましく、炭素数2〜4のアルキル基を有する(メタ)アクリル酸アルキルエステルに由来する構成単位及び/又は炭素数2〜4のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステルに由来する構成単位を有することが特に好ましい。(メタ)アクリル酸エステルに由来する構成単位は、単独または2種以上の(メタ)アクリル酸エステルに由来する構成単位であってよい。 Examples of the structural unit derived from the (meth) acrylic acid ester include a structural unit derived from the (meth) acrylic acid alkyl ester and / or a structural unit derived from the (meth) acrylic acid alkoxyalkyl ester, and carbon. A structural unit derived from a (meth) acrylic acid alkyl ester having an alkyl group of several 1 to 8, and a structural unit derived from a (meth) acrylic acid alkoxyalkyl ester having an alkoxyalkyl group having 2 to 8 carbon atoms. Preferably, a structural unit derived from a (meth) acrylic acid alkyl ester having an alkyl group having 2 to 6 carbon atoms and / or a configuration derived from a (meth) acrylic acid alkoxyalkyl ester having an alkoxyalkyl group having 2 to 6 carbon atoms. It is more preferable to have a unit, and a structural unit derived from a (meth) acrylic acid alkyl ester having an alkyl group having 2 to 4 carbon atoms and / or an alkoxyalkyl (meth) acrylic acid having an alkoxyalkyl group having 2 to 4 carbon atoms. It is particularly preferable to have a structural unit derived from an alkyl ester. The structural unit derived from the (meth) acrylic acid ester may be a structural unit derived from one or more (meth) acrylic acid esters.
(メタ)アクリル酸アルキルエステルの具体例としては、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸n−プロピル、(メタ)アクリル酸イソプロピル、(メタ)アクリル酸n−ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸n−ペンチル、(メタ)アクリル酸n−ヘキシル、(メタ)アクリル酸n−ヘプチル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸シクロヘキシル等の(メタ)アクリル酸エステルを例示することができ、(メタ)アクリル酸エチル、(メタ)アクリル酸n-ブチルであることが好ましい。
(メタ)アクリル酸アルコキシアルキルエステルの具体例としては、(メタ)アクリル酸メトキシメチル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸エトキシメチル、(メタ)アクリル酸2−エトキシエチル、(メタ)アクリル酸2−プロポキシエチル、(メタ)アクリル酸2−ブトキシエチル、(メタ)アクリル酸2−メトキシプロピル、(メタ)アクリル酸2−エトキシプロピル、(メタ)アクリル酸3−メトキシプロピル、(メタ)アクリル酸3−エトキシプロピル、(メタ)アクリル酸4−メトキシブチル、(メタ)アクリル酸4−エトキシブチル等の(メタ)アクリル酸エステルを例示することができ、(メタ)アクリル酸メトキシエチルであることが好ましい。
Specific examples of the (meth) acrylic acid alkyl ester include methyl (meth) acrylic acid, ethyl (meth) acrylic acid, n-propyl (meth) acrylic acid, isopropyl (meth) acrylic acid, and n- (meth) acrylic acid. Butyl, isobutyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, (meth) acrylate (Meta) acrylic acid esters such as 2-ethylhexyl and cyclohexyl (meth) acrylate can be exemplified, and ethyl (meth) acrylate and n-butyl (meth) acrylate are preferable.
Specific examples of the (meth) acrylic acid alkoxyalkyl ester include methoxymethyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, and (meth). ) 2-propoxyethyl acrylate, 2-butoxyethyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, 2-ethoxypropyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, (meth) ) (Meta) acrylic acid esters such as 3-ethoxypropyl acrylate, 4-methoxybutyl (meth) acrylate, 4-ethoxybutyl (meth) acrylate can be exemplified, and methoxyethyl (meth) acrylate can be used. It is preferable to have.
本発明のマレイミドに由来する構成単位を有する重合体の全構成単位において、アクリル酸エステルに由来する構成単位に由来する構成単位の含有量は、下限は45質量%以上であることが好ましく、50質量%以上であることがより好ましく、60質量%以上であることが特に好ましく、75質量%以上、80質量%以上、85質量%以上、90質量%以上であってよい。上限は99.5質量%以下であることが好ましく、99質量%以下であることがより好ましく、98.5質量%以下であることが特に好ましい。 In all the structural units of the polymer having the structural unit derived from maleimide of the present invention, the content of the structural unit derived from the structural unit derived from acrylic acid ester is preferably 45% by mass or more, preferably 50% by mass or more. It is more preferably mass% or more, particularly preferably 60 mass% or more, and may be 75 mass% or more, 80 mass% or more, 85 mass% or more, 90 mass% or more. The upper limit is preferably 99.5% by mass or less, more preferably 99% by mass or less, and particularly preferably 98.5% by mass or less.
さらに本発明のマレイミドに由来する構成単位を有する重合体は、上記の構成単位以外に、これらと共重合可能なその他の単量体に由来する構成単位を含有してもよい。その他の構成単位としては、エチレン性不飽和ニトリルに由来する構成単位、(メタ)アクリルアミド系モノマーに由来する構成単位、芳香族ビニル系モノマーに由来する構成単位、共役ジエン系モノマーに由来する構成単位、非共役ジエン類に由来する構成単位、その他のオレフィンに由来する構成単位等が挙げられる。 Further, the polymer having a structural unit derived from maleimide of the present invention may contain a structural unit derived from other monomers copolymerizable with these structural units in addition to the above structural units. Other structural units include a structural unit derived from an ethylenically unsaturated nitrile, a structural unit derived from a (meth) acrylamide-based monomer, a structural unit derived from an aromatic vinyl-based monomer, and a structural unit derived from a conjugated diene-based monomer. , Constituent units derived from non-conjugated diene, other structural units derived from olefins and the like.
エチレン性不飽和ニトリルに由来する構成単位としては、アクリロニトリル、メタクリロニトリル、α−メトキシアクリロニトリル、シアン化ビニリデン等の化合物に由来する構成単位が挙げられる。 Examples of the structural unit derived from the ethylenically unsaturated nitrile include a structural unit derived from a compound such as acrylonitrile, methacrylonitrile, α-methoxyacrylonitrile, and vinylidene cyanide.
(メタ)アクリルアミド系モノマーに由来する構成単位としては、アクリルアミド、メタクリルアミド、ジアセトンアクリルアミド、ジアセトンメタクリルアミド、N−ブトキシメチルアクリルアミド、N−ブトキシメチルメタクリルアミド、N−ブトキシエチルアクリルアミド、N−ブトキシエチルメタクリルアミド、N−メトキシメチルアクリルアミド、N−メトキシメチルメタクリルアミド、N−プロピオキシメチルアクリルアミド、N−プロピオキシメチルメタクリルアミド、N−メチルアクリルアミド、N−メチルメタクリルアミド、N,N−ジメチルアクリルアミド、N,N−ジメチルメタクリルアミド、N,N−ジエチルアクリルアミド、N,N−ジエチルメタクリルアミド、N−メチロールアクリルアミド、N−メチロールメタクリルアミド、エタクリルアミド、クロトンアミド、ケイ皮酸アミド、マレインジアミド、イタコンジアミド、メチルマレインアミド、メチルイタコンアミド、マレインイミド、イタコンイミド等の化合物に由来する構成単位が挙げられる。 The structural units derived from the (meth) acrylamide-based monomer include acrylamide, methacrylicamide, diacetoneacrylamide, diacetonemethacrylate, N-butoxymethylacrylamide, N-butoxymethylmethacrylate, N-butoxyethylacrylamide, and N-butoxy. Ethylmethacrylate, N-methoxymethylacrylamide, N-methoxymethylmethacrylate, N-propioxymethylacrylamide, N-propioxymethylmethacrylate, N-methylacrylamide, N-methylmethacrylate, N, N-dimethylacrylamide, N, N-dimethylmethacrylamide, N, N-diethylacrylamide, N, N-diethylmethacrylate, N-methylolacrylamide, N-methylolmethacrylate, ethanecrylamide, crotonamide, silicic acid amide, maleindiamide, itacondiamide, Examples thereof include structural units derived from compounds such as methylmaleinamide, methylitaconamide, maleinimide, and itaconimide.
芳香族ビニル系モノマーに由来する構成単位としては、スチレン、α−メチルスチレン、o−メチルスチレン、p−メチルスチレン、o−エチルスチレン、p−エチルスチレン、α−フルオロスチレン、p−トリフルオロメチルスチレン、p−メトキシスチレン、p−アミノスチレン、p−ジメチルアミノスチレン、p−アセトキシスチレン、スチレンスルホン酸あるいはその塩、α−ビニルナフタレン、1−ビニルナフタレン−4−スルホン酸あるいはその塩、2−ビニルフルオレン、2−ビニルピリジン、4−ビニルピリジン、ジビニルベンゼン、ジイソプロペニルベンゼン、ビニルベンジルクロライド等の化合物に由来する構成単位が挙げられる。 The structural units derived from aromatic vinyl-based monomers include styrene, α-methylstyrene, o-methylstyrene, p-methylstyrene, o-ethylstyrene, p-ethylstyrene, α-fluorostyrene, and p-trifluoromethyl. Styrene, p-methoxystyrene, p-aminostyrene, p-dimethylaminostyrene, p-acetoxystyrene, styrene sulfonic acid or a salt thereof, α-vinylnaphthalene, 1-vinylnaphthalene-4-sulfonic acid or a salt thereof, 2- Examples thereof include structural units derived from compounds such as vinylfluorene, 2-vinylpyridine, 4-vinylpyridine, divinylbenzene, diisopropenylbenzene, and vinylbenzyl chloride.
共役ジエン系モノマーに由来する構成単位としては、1,3−ブタジエン、2−メチル−1,3−ブタジエン、2−クロロ−1,3−ブタジエン、1,2−ジクロロ−1,3−ブタジエン、2,3−ジクロロ−1,3−ブタジエン、2,3−ジメチル−1,3−ブタジエン、2−ネオペンチル−1,3−ブタジエン、2−ブロモ−1,3−ブタジエン、2−シアノ−1,3−ブタジエン、1,3−ペンタジエン、1,3−ヘキサジエン、クロロプレン、ピぺリレン等の化合物に由来する構成単位が挙げられる。 The structural units derived from the conjugated diene-based monomer include 1,3-butadiene, 2-methyl-1,3-butadiene, 2-chloro-1,3-butadiene, 1,2-dichloro-1,3-butadiene, 2,3-Dichloro-1,3-butadiene, 2,3-dimethyl-1,3-butadiene, 2-neopentyl-1,3-butadiene, 2-bromo-1,3-butadiene, 2-cyano-1, Examples thereof include structural units derived from compounds such as 3-butadiene, 1,3-pentadiene, 1,3-hexadiene, chloroprene, and piperylene.
また、非共役ジエン類に由来する構成単位としては、1,4−ペンタジエン、1,4−ヘキサジエン、エチリデンノルボルネン、ノルボルナジエン、ジシクロペンタジエン等の非共役ジエン類の化合物に由来する構成単位が挙げられる。 Examples of the structural unit derived from the non-conjugated diene include a structural unit derived from a compound of the non-conjugated diene such as 1,4-pentadiene, 1,4-hexadiene, etylidene norbornene, norbornadiene, and dicyclopentadiene. ..
その他のオレフィン系モノマーに由来する構成単位としては、アクリル酸ジシクロペンタジエニル、メタクリル酸ジシクロペンタジエニルメタクリレート、アクリル酸ジシクロペンタジエニルエチル、メタクリル酸ジシクロペンタジエニルエチル等のエステル類、エチレン、プロピレン、塩化ビニル、塩化ビニリデン、1,2−ジクロロエチレン、酢酸ビニル、フッ化ビニル、フッ化ビニリデン、1,2−ジフルオロエチレン、臭化ビニル、臭化ビニリデン、1,2−ジブロモエチレン、エチルビニルエーテル、ブチルビニルエーテル等の化合物に由来する構成単位が挙げられる。 As structural units derived from other olefin-based monomers, esters such as dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate methacrylate, dicyclopentadienylethyl acrylate, and dicyclopentadienylethyl methacrylate Kinds, ethylene, propylene, vinyl chloride, vinylidene chloride, 1,2-dichloroethylene, vinyl acetate, vinyl fluoride, vinylidene fluoride, 1,2-difluoroethylene, vinyl bromide, vinylidene bromide, 1,2-dibromoethylene , Ethylene vinyl ether, butyl vinyl ether and other constituent units derived from compounds.
本発明のマレイミドに由来する構成単位を有する重合体において、これらの共重合可能なその他の単量体に由来する構成単位を含有させる場合には、全構成単位における含有量は0〜15質量%であってよく、0〜10質量%であってよく、0〜5質量%であってよい。 When a polymer having a structural unit derived from maleimide of the present invention contains a structural unit derived from these other copolymerizable monomers, the content in all the structural units is 0 to 15% by mass. It may be 0 to 10% by mass, and may be 0 to 5% by mass.
本発明のマレイミドに由来する構成単位を有する重合体において、その構成単位の含有量については、得られた重合体の核磁気共鳴スペクトルにより決定することができる。 In a polymer having a structural unit derived from maleimide of the present invention, the content of the structural unit can be determined from the nuclear magnetic resonance spectrum of the obtained polymer.
<マレイミドに由来する構成単位を有する重合体の製造方法>
本発明で用いるマレイミドに由来する構成単位を有する重合体は、それぞれ各種モノマーを重合することにより得ることができる。使用するモノマーはいずれも市販品であってよく、特に制約はない。
<Method for producing a polymer having a structural unit derived from maleimide>
The polymer having a structural unit derived from maleimide used in the present invention can be obtained by polymerizing various monomers. Any of the monomers used may be a commercially available product, and there are no particular restrictions.
重合反応の形態としては、乳化重合法、懸濁重合法、塊状重合法、および溶液重合法のいずれも用いることができるが、重合反応の制御の容易性などの点から、従来公知のアクリル共重合体の製造法として一般的に用いられている常圧下での乳化重合法によるのが好ましい。 As the form of the polymerization reaction, any of an emulsion polymerization method, a suspension polymerization method, a massive polymerization method, and a solution polymerization method can be used, but from the viewpoint of ease of control of the polymerization reaction, conventionally known acrylic copolymers can be used. It is preferable to use an emulsion polymerization method under normal pressure, which is generally used as a method for producing a polymer.
乳化重合による重合の場合には、通常の方法を用いればよく、重合開始剤、乳化剤、連鎖移動剤、重合停止剤等は一般的に使用される従来公知のものが使用できる。 In the case of polymerization by emulsion polymerization, a usual method may be used, and conventionally known polymerization initiators, emulsifiers, chain transfer agents, polymerization terminators and the like can be used.
本発明で用いられる乳化剤は特に限定されず、乳化重合法おいて一般的に用いられるノニオン性乳化剤およびアニオン性乳化剤等を使用することができる。ノニオン乳化剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルコールエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレン多環フェニルエーテル、ポリオキシアルキレンアルキルエーテル、ソルビタン脂肪酸エステル、ポリオキシエチレン脂肪酸エステルおよびポリオキシエチレンソルビタン脂肪酸エステル等があげられ、アニオン性乳化剤としては、アルキルベンゼンスルホン酸塩、アルキル硫酸エステル塩、ポリオキシエチレンアルキルエーテル硫酸エステル塩、ポリオキシアルキレンアルキルエーテルリン酸エステルまたはその塩、脂肪酸塩等があげられ、これらを1種または2種以上用いてもよい。アニオン性乳化剤の代表例としてはドデシル硫酸ナトリウム、ドデシルベンゼンスルホン酸ナトリウム、ドデシル硫酸トリエタノールアミンが挙げられる。 The emulsifier used in the present invention is not particularly limited, and nonionic emulsifiers, anionic emulsifiers and the like generally used in the emulsion polymerization method can be used. Nonionic emulsifiers include, for example, polyoxyethylene alkyl ethers, polyoxyethylene alcohol ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene polycyclic phenyl ethers, polyoxyalkylene alkyl ethers, sorbitan fatty acid esters, polyoxyethylene fatty acid esters and Examples thereof include polyoxyethylene sorbitan fatty acid ester, and examples of the anionic emulsifier include alkylbenzene sulfonate, alkyl sulfate ester salt, polyoxyethylene alkyl ether sulfate ester salt, polyoxyalkylene alkyl ether phosphate ester or its salt, and fatty acid salt. Etc., and one or more of these may be used. Typical examples of anionic emulsifiers include sodium dodecyl sulfate, sodium dodecylbenzene sulfonate, and triethanolamine dodecyl sulfate.
本発明で用いられる乳化剤の使用量は乳化重合法おいて一般的に用いられる量であればよい。具体的には、仕込みのモノマー量に対して、0.01〜10質量%の範囲が好ましく、より好ましくは0.03質量%以上、更に好ましくは0.05質量%以上であり、より好ましくは7質量%以下、更に好ましくは5質量%以下である。モノマー成分として、反応性界面活性剤を用いる場合は、乳化剤の添加は必ずしも必要でない。 The amount of the emulsifier used in the present invention may be any amount generally used in the emulsion polymerization method. Specifically, it is preferably in the range of 0.01 to 10% by mass, more preferably 0.03% by mass or more, still more preferably 0.05% by mass or more, and more preferably, with respect to the amount of the charged monomer. It is 7% by mass or less, more preferably 5% by mass or less. When a reactive surfactant is used as the monomer component, it is not always necessary to add an emulsifier.
本発明で用いられる重合開始剤は特に限定されず、乳化重合法おいて一般的に用いられる重合開始剤を使用することができる。その具体例としては、過硫酸カリウム、過硫酸ナトリウムおよび過硫酸アンモニウムなどの過硫酸塩に代表される無機系重合開始剤、2,2−ジ(4,4−ジ−(t−ブチルパーオキシ)シクロヘキシル)プロパン、1−ジ−(t−ヘキシルパーオキシ)シクロヘキサン、1,1−ジ−(t−ブチルパーオキシ)シクロヘキサン、4,4−ジ−(t−ブチルパーオキシ)吉草酸n−ブチル、2,2−ジ(t−ブチルパーオキシ)ブタン、t−ブチルハイドロパーオキサイド、クメンハイドロパーオキサイド、ジイソプロピルベンゼンハイドロパーオキサイド、p−メンタンハイドロパーオキサイド、1,1,3,3−テトラメチルブチルハイドロパーオキサイド、t−ブチルクミルパーオキサイド、ジ−t−ブチルパーオキサイド、ジ−t−ヘキシルパーオキサイド、ジ(2−t−ブチルパーオキシイソプロピル)ベンゼン、ジクミルパーオキサイド、ジイソブチリルパーオキサイド、ジ(3,5,5−トリメチルヘキサノイル)パーオキサイド、ジラウロイルパーオキサイド、ジコハク酸パーオキサイド、ジベンゾイルパーオキサイド、ジ(3−メチルベンゾイル)パーオキサイド、ベンゾイル(3−メチルベンゾイル)パーオキサイド、ジイソプロピルパーオキシジカーボネート、ジ−n−プロピルパーオキシジカーボネート、ジ(4−t−ブチルシクロヘキシル)パーオキシジカーボネート、ジ(2−エチルヘキシル)パーオキシジカーボネート、ジ−sec−ブチルパーオキシジカーボネート、クミルパーオキシネオデカネート、1,1,3,3−テトラメチルブチルパーオキシネオデカネート、t−ヘキシルパーオキシネオデカネート、t−ブチルパーオキシネオデカネート、t−ヘキシルパーオキシピバレート、t−ブチルパーオキシピバレート、2,5−ジメチル−2,5−ジ(2−エチルヘキサノイルパーオキシ)ヘキサン、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサネート、t−ヘキシルパーオキシ−2−エチルヘキサネート、t−ブチルパーオキシ−2−エチルヘキサネート、t−ブチルパーオキシラウレート、t−ブチルパーオキシ−3,5,5−トリメチルヘキサネート、t−ヘキシルパーオキシイソプロピルモノカーボネート、t−ブチルパーオキシイソプロピルモノカーボネート、t−ブチルパーオキシ2−エチルヘキシルモノカーボネート、2,5−ジメチル−2,5−ジ(ベンゾイルパーオキシ)ヘキサン、t−ブチルパーオキシアセテート、t−ヘキシルパーオキシベンゾエート、t−ブチルパーオキシベンゾエート、2,5−ジメチル−2,5−ジ(t−ブチルパーオキシ)ヘキサン等の有機過酸化物系の重合開始剤、ハイドロパーオキサイド、アゾビスイソブチロニトリル、4−4’−アゾビス(4−シアノ吉草酸)、2−2’−アゾビス[2−(2−イミダゾリン−2−イル)プロパン、2−2’−アゾビス(プロパン−2−カルボアミジン)2−2’−アゾビス[N−(2−カルボキシエチル)−2−メチルプロパンアミド、2−2’−アゾビス{2−[1−(2−ヒドロキシエチル)−2−イミダゾリン−2−イル]プロパン}、2−2’−アゾビス(1−イミノ−1−ピロリジノ−2−メチルプロパン)および2−2’−アゾビス{2−メチル−N−[1,1−ビス(ヒドロキシメチル)−2−ヒドロキシエチル]プロパンアミド}などのアゾ系開始剤等が挙げられる。これら重合開始剤は1種または2種以上組み合わせて用いてもよい。 The polymerization initiator used in the present invention is not particularly limited, and a polymerization initiator generally used in the emulsion polymerization method can be used. Specific examples thereof include inorganic polymerization initiators typified by persulfates such as potassium persulfate, sodium persulfate and ammonium persulfate, 2,2-di (4,5-di- (t-butylperoxy)). Cyclohexyl) propane, 1-di- (t-hexyl peroxy) cyclohexane, 1,1-di- (t-butylperoxy) cyclohexane, 4,4-di- (t-butylperoxy) n-butyl valerate , 2,2-Di (t-butylperoxy) butane, t-butylhydroperoxide, cumenehydroperoxide, diisopropylbenzenehydroperoxide, p-menthanhydroperoxide, 1,1,3,3-tetramethyl Butylhydroperoxide, t-butylcumyl peroxide, di-t-butyl peroxide, di-t-hexyl peroxide, di (2-t-butylperoxyisopropyl) benzene, dicumyl peroxide, diisobutyryl peroxide , Di (3,5,5-trimethylhexanoyl) peroxide, dilauroyl peroxide, disuccinate peroxide, dibenzoyl peroxide, di (3-methylbenzoyl) peroxide, benzoyl (3-methylbenzoyl) peroxide , Diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di (4-t-butylcyclohexyl) peroxydicarbonate, di (2-ethylhexyl) peroxydicarbonate, di-sec-butylperoxydi Carbonate, cumylperoxyneodecanate, 1,1,3,3-tetramethylbutylperoxyneodecanate, t-hexylperoxyneodecanate, t-butylperoxyneodecanate, t-hexylperoxypi Valate, t-butylperoxypivalate, 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy) hexane, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa Nate, t-hexyl peroxy-2-ethylhexanate, t-butylperoxy-2-ethylhexanate, t-butylperoxylaurate, t-butylperoxy-3,5,5-trimethylhexanate, t-Hexyl peroxyisopropyl monocarbonate, t-butylperoxyisopropyl monocarbonate, t-butylperoxy2-ethylhexyl monocarbonate, 2,5-dimethyl-2 , 5-Di (benzoylperoxy) hexane, t-butylperoxyacetate, t-hexylperoxybenzoate, t-butylperoxybenzoate, 2,5-dimethyl-2,5-di (t-butylperoxy) Organic peroxide-based polymerization initiator such as hexane, hydroperoxide, azobisisobutyronitrile, 4-4'-azobis (4-cyanovaleric acid), 2-2'-azobis [2- (2- (2-) Imidazoline-2-yl) Propane, 2-2'-azobis (Propane-2-carboamidine) 2-2'-azobis [N- (2-carboxyethyl) -2-methylpropaneamide, 2-2'-azobis {2- [1- (2-Hydroxyethyl) -2-imidazolin-2-yl] propane}, 2-2'-azobis (1-imino-1-pyrrolidino-2-methylpropane) and 2-2'- Examples thereof include azo-based initiators such as azobis {2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] propanamide}. These polymerization initiators may be used alone or in combination of two or more.
本発明で用いられる重合開始剤の使用量は乳化重合法おいて一般的に用いられる量であればよい。具体的には、仕込みのモノマー量に対して、0.01〜5質量%が好ましく、より好ましくは0.01質量%以上、更に好ましくは0.02質量%以上、より好ましくは4質量%以下、更に好ましくは3質量%以下である。 The amount of the polymerization initiator used in the present invention may be any amount generally used in the emulsion polymerization method. Specifically, 0.01 to 5% by mass is preferable, more preferably 0.01% by mass or more, still more preferably 0.02% by mass or more, and more preferably 4% by mass or less with respect to the amount of the charged monomer. , More preferably 3% by mass or less.
また、重合開始剤としての有機過酸化物および無機過酸化物は、還元剤と組み合わせることにより、レドックス系重合開始剤として使用することができる。組み合わせて用いる還元剤としては、特に限定されないが、硫酸第一鉄、ナフテン酸第一銅等の還元状態にある金属イオンを含有する化合物、メタンスルホン酸ナトリウム等のメタン化合物、ジメチルアニリン等のアミン化合物、アスコルビン酸およびその塩、亜硫酸およびチオ硫酸のアルカリ金属塩などの還元性を有する無機塩などが挙げられる。これらの還元剤は単独でまたは2種以上を組合せて用いることができる。還元剤の使用量は、仕込みモノマー100質量部に対して好ましくは0.0003〜10.0質量部である。 Further, the organic peroxide and the inorganic peroxide as the polymerization initiator can be used as a redox-based polymerization initiator by combining with a reducing agent. The reducing agent used in combination is not particularly limited, but is not particularly limited, but is a compound containing a metal ion in a reduced state such as ferrous sulfate and ferrous naphthenate, a methane compound such as sodium methanesulfonate, and an amine such as dimethylaniline. Examples thereof include compounds, ascorbic acid and salts thereof, and reducing inorganic salts such as alkali metal salts of sulfurous acid and thiosulfate. These reducing agents can be used alone or in combination of two or more. The amount of the reducing agent used is preferably 0.0003 to 10.0 parts by mass with respect to 100 parts by mass of the charged monomer.
連鎖移動剤は、必要に応じて用いることができる。連鎖移動剤の具体例としては、n−ヘキシルメルカプタン、n−オクチルメルカプタン、t−オクチルメルカプタン、n−ドデシルメルカプタン、t−ドデシルメルカプタン、n−ステアリルメルカプタン等のアルキルメルカプタン、2,4−ジフェニル−4−メチル−1−ペンテン、2,4−ジフェニル−4−メチル−2−ペンテン、ジメチルキサントゲンジサルファイド、ジイソプロピルキサントゲンジサルファイド等のキサントゲン化合物、ターピノレン、テトラメチルチウラムジスルフィド、テトラエチルチウラムジスルフィド、テトラメチルチウラムモノスルフィド等のチウラム系化合物、2,6−ジ−t−ブチル−4−メチルフェノール、スチレン化フェノール等のフェノール系化合物、アリルアルコール等のアリル化合物、ジクロルメタン、ジブロモメタン、四臭化炭素等のハロゲン化炭化水素化合物、α−ベンジルオキシスチレン、α−ベンジルオキシアクリロニトリル、α−ベンジルオキシアクリルアミド等のビニルエーテル、トリフェニルエタン、ペンタフェニルエタン、アクロレイン、メタアクロレイン、チオグリコール酸、チオリンゴ酸、2−エチルヘキシルチオグリコレート等が挙げられ、これらを1種または2種以上用いてもよい。これらの連鎖移動剤の量は特に限定されないが、通常、仕込モノマー量100質量部に対して0〜5質量部にて使用される。 Chain transfer agents can be used as needed. Specific examples of the chain transfer agent include alkyl mercaptans such as n-hexyl mercaptan, n-octyl mercaptan, t-octyl mercaptan, n-dodecyl mercaptan, t-dodecyl mercaptan, and n-stearyl mercaptan, 2,4-diphenyl-4. Xanthogen compounds such as −methyl-1-pentene, 2,4-diphenyl-4-methyl-2-pentene, dimethylxanthogen disulfide, diisopropylxanthogen disulfide, turpinolene, tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetramethylthiurammono Thiol compounds such as sulfides, phenolic compounds such as 2,6-di-t-butyl-4-methylphenol and styrated phenol, allyl compounds such as allyl alcohol, halogens such as dichloromethane, dibromomethane and carbon tetrabromide. Hydrocarbon compounds, vinyl ethers such as α-benzyloxystyrene, α-benzyloxyacrylonitrile, α-benzyloxyacrylamide, triphenylethane, pentaphenylethane, achlorine, metaacrolein, thioglycolic acid, thioallic acid, 2-ethylhexylthio Glycolate and the like can be mentioned, and one or more of these may be used. The amount of these chain transfer agents is not particularly limited, but is usually used in an amount of 0 to 5 parts by mass with respect to 100 parts by mass of the charged monomer.
重合停止剤としては、例えば、ヒドロキシルアミン、ヒドロキシアミン硫酸塩、ジエチルヒドロキシアミン、ヒドロキシアミンスルホン酸およびそのアルカリ金属塩、ジメチルジチオカルバミン酸ナトリウムおよびヒドロキノンなどのキノン化合物などが挙げられる。重合停止剤の使用量は、特に限定されないが、通常、全単量体100質量部に対して、0〜2質量部である。 Examples of the polymerization terminator include hydroxylamine, hydroxyamine sulfate, diethylhydroxyamine, hydroxyamine sulfonic acid and alkali metal salts thereof, and quinone compounds such as sodium dimethyldithiocarbamate and hydroquinone. The amount of the polymerization inhibitor used is not particularly limited, but is usually 0 to 2 parts by mass with respect to 100 parts by mass of all the monomers.
さらに上記の方法によって得られた重合体は、必要に応じてpH調整剤として塩基を用いることでpHを調整することができる。塩基の具体例としては、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、アンモニア、無機アンモニウム化合物、有機アミン化合物等が挙げられる。pHの範囲はpH1〜11が好ましく、より好ましくはpH1.5以上、更に好ましくはpH2以上であり、より好ましくはpH10.5以下、更に好ましくはpH10以下である。 Further, the pH of the polymer obtained by the above method can be adjusted by using a base as a pH adjusting agent, if necessary. Specific examples of the base include sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonia, an inorganic ammonium compound, an organic amine compound and the like. The pH range is preferably pH 1 to 11, more preferably pH 1.5 or higher, further preferably pH 2 or higher, more preferably pH 10.5 or lower, still more preferably pH 10 or lower.
これ以外にも必要に応じて、粒径調整剤、キレート化剤、酸素捕捉剤等の重合副資材を使用することができる。 In addition to this, if necessary, polymerization auxiliary materials such as a particle size adjusting agent, a chelating agent, and an oxygen scavenger can be used.
乳化重合は、回分式、半回分式、連続式のいずれでもよい。重合時間および重合温度は特に限定されない。使用する重合開始剤の種類等から適宜選択できるが、一般的に、重合温度は10〜100℃であり、重合時間は0.5〜100時間である。 The emulsion polymerization may be a batch type, a semi-batch type, or a continuous type. The polymerization time and polymerization temperature are not particularly limited. It can be appropriately selected from the type of polymerization initiator used, but generally, the polymerization temperature is 10 to 100 ° C. and the polymerization time is 0.5 to 100 hours.
上記の方法で得られた重合体を回収する方法については特に制限はなく、一般に行われている方法を採用することができる。その方法の一例として、重合液を、凝固剤を含む水溶液に連続的または回分的に供給する方法が挙げられ、この操作によって凝固スラリーが得られる。その際凝固剤を含む水溶液の温度は、モノマーの種類と使用量、撹拌等による剪断力などの凝固条件の影響を受けるため、これを一律に規定することはできないが、一般的には50℃以上、好ましくは60℃〜100℃の範囲である The method for recovering the polymer obtained by the above method is not particularly limited, and a generally used method can be adopted. As an example of the method, a method of continuously or batch-supplying the polymerization solution to an aqueous solution containing a coagulant can be mentioned, and a coagulated slurry can be obtained by this operation. At that time, the temperature of the aqueous solution containing the coagulant is affected by the coagulation conditions such as the type and amount of the monomer used and the shearing force due to stirring, etc., so this cannot be specified uniformly, but in general, it is 50 ° C. The above is preferably in the range of 60 ° C to 100 ° C.
上記の方法で得られた凝固スラリーは、凝固剤を除去するために水洗洗浄を行なうことが好ましい。水洗洗浄を全く行わなかったり、あるいは洗浄が不十分である場合凝固剤に由来するイオン残留物が成形工程で析出されてしまう恐れがある。 The coagulated slurry obtained by the above method is preferably washed with water in order to remove the coagulant. If the washing with water is not performed at all, or if the washing is insufficient, the ion residue derived from the coagulant may be precipitated in the molding process.
水洗洗浄後の凝固スラリーから水分を除去し乾燥することでマレイミドに由来する構成単位を有する重合体を得ることができる。乾燥の方法としては特に限定されないが一般的にはフラッシュドライヤーや流動乾燥機などを用いて乾燥される。また、乾燥工程の前に遠心分離機等による脱水工程を経ても良い。 A polymer having a structural unit derived from maleimide can be obtained by removing water from the solidified slurry after washing with water and drying. The drying method is not particularly limited, but is generally dried using a flash dryer, a fluidized dryer, or the like. Further, a dehydration step using a centrifuge or the like may be performed before the drying step.
<架橋用組成物>
本発明の架橋用組成物は、上記のマレイミドに由来する構成単位を有する重合体及び架橋剤を少なくとも含有する。
<Crosslink composition>
The cross-linking composition of the present invention contains at least a polymer having a structural unit derived from the above-mentioned maleimide and a cross-linking agent.
架橋剤としては、分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物であり求核置換反応において脱離できる脱離基を2個以上含有する必要があり、脱離基としては、塩素、臭素、ヨウ素等のハロゲン基(原子)、スルホン酸基を例示することができる。分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物としては、1,6-ジブロモヘキサン、1,6-ジブロモプロパン、1,6-ジヨードヘキサン、1,6-ジクロロヘキサン、1,9-ジブロモノナン、1,4-ジブロモペンタン、2,5-ジブロモヘキサン等のジハロアルキル化合物やp-キシレンジブロミド、p-キシレンジクロリド、等の芳香環含有するジハロ有機化合物や1,2,5-トリブロモヘキサンや1,2,5,6-テトラブロモヘキサン等の3つ以上の脱離基を含む有機化合物や1,4-ブタンジオールジメタンスルホナートなどのスルホニル基を2個有する化合物などを例示することができる。スルホニル基の具体例としては、メタンスルホニル基、p-トルエンスルホニル基、o-ニトロベンゼンスルホニル基、トリフルオロメタンスルホニル基などが挙げられる。
加硫速度の観点から、分子内に少なくとも2以上の脱離基が一級の位置であるジハロアルキル化合物、スルホニル基含有化合物であることがより好ましい。ジハロアルキル化合物の炭素数は1〜10であることが好ましく、2〜6であることがより好ましい。
The cross-linking agent is a polyfunctional organic compound containing at least two or more leaving groups in the molecule, and must contain two or more leaving groups that can be eliminated in the nucleophilic substitution reaction. Can exemplify halogen groups (atoms) such as chlorine, bromine, and iodine, and sulfonic acid groups. Examples of the polyfunctional organic compound containing at least two or more elimination groups in the molecule include 1,6-dibromohexane, 1,6-dibromopropane, 1,6-diiodohexane, and 1,6-dichlorohexane. Dihaloalkyl compounds such as 1,9-dibromononane, 1,4-dibromopentane, 2,5-dibromohexane, dihaloorganic compounds containing aromatic rings such as p-xylene dibromid and p-xylene chloride chloride, and 1,2. It has two sulfonyl groups such as 1,4-butanediol dimethanesulfonate and organic compounds containing three or more leaving groups such as 5-tribromohexane and 1,2,5,6-tetrabromohexane. Compounds and the like can be exemplified. Specific examples of the sulfonyl group include a methanesulfonyl group, a p-toluenesulfonyl group, an o-nitrobenzenesulfonyl group, a trifluoromethanesulfonyl group and the like.
From the viewpoint of the vulcanization rate, a dihaloalkyl compound or a sulfonyl group-containing compound in which at least two or more leaving groups are in the primary position in the molecule is more preferable. The dihaloalkyl compound preferably has 1 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
これらの架橋剤は単独で用いてもよいし、2種類以上の組み合わせで用いてもよい。架橋剤の量は、本発明のマレイミドに由来する構成単位を有する重合体100質量部に対して、0.1質量部以上であることが好ましく、0.3質量部以上であることがより好ましく、0.5質量部以上であることが特に好ましく、20質量部以下であることが好ましく、5質量部以下であることがより好ましく、3質量部以下であることが特に好ましい。 These cross-linking agents may be used alone or in combination of two or more. The amount of the cross-linking agent is preferably 0.1 part by mass or more, and more preferably 0.3 part by mass or more with respect to 100 parts by mass of the polymer having a structural unit derived from maleimide of the present invention. , 0.5 parts by mass or more, preferably 20 parts by mass or less, more preferably 5 parts by mass or less, and particularly preferably 3 parts by mass or less.
また、本発明の架橋用組成物には必要に応じて塩基を添加することができる。 In addition, a base can be added to the cross-linking composition of the present invention as needed.
塩基の具体例としては、アルカリ土類金属またはアルカリ金属の水酸化物、炭酸塩、酢酸塩等の無機塩基、アミン類等の有機塩基を例示することができ、炭酸カリウム、炭酸ナトリウム、炭酸セシウム、カリウムtert-ブトキシド、ナトリウムtert-ブトキシド等の無機塩基やトリエチルアミン、N,N-ジイソプロピルエチルアミン、ジアザビシクロウンデセン等の有機塩基使用することができる。塩基の種類としては求核性の低い塩基を使用することがより好ましい。 Specific examples of the base include inorganic bases such as alkaline earth metals or alkali metal hydroxides, carbonates and acetates, and organic bases such as amines, such as potassium carbonate, sodium carbonate and cesium carbonate. , Inorganic bases such as potassium tert-butoxide and sodium tert-butoxide and organic bases such as triethylamine, N, N-diisopropylethylamine and diazabicycloundecene can be used. It is more preferable to use a base having low nucleophilicity as the type of base.
塩基の量は、本発明のマレイミドに由来する構成単位を有する重合体100質量部に対して、0.5質量部以上であることが好ましく、1質量部以上であることがより好ましく、3質量部以上であることが特に好ましく、20質量部以下であることが好ましく、18質量部以下であることがより好ましく、15質量部以下であることが特に好ましい。特に塩基の量が少なすぎると架橋反応が十分の進行しないことがある。 The amount of the base is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and 3 parts by mass with respect to 100 parts by mass of the polymer having a structural unit derived from maleimide of the present invention. It is particularly preferably parts or more, preferably 20 parts by mass or less, more preferably 18 parts by mass or less, and particularly preferably 15 parts by mass or less. In particular, if the amount of base is too small, the cross-linking reaction may not proceed sufficiently.
また、本発明の架橋用組成物は、当該技術分野で通常使用される他の添加剤、例えば滑剤、軟化剤、老化防止剤、光安定化剤、充填剤、補強剤、可塑剤、加工助剤、顔料、着色剤、帯電防止剤、発泡剤等を任意に配合できる。 In addition, the cross-linking composition of the present invention includes other additives usually used in the art, such as lubricants, softeners, antistatic agents, light stabilizers, fillers, reinforcing agents, plasticizers, and processing aids. Agents, pigments, colorants, antistatic agents, foaming agents and the like can be arbitrarily blended.
充填剤としては、公知の充填剤を使用することができ、具体的には炭酸カルシウム、タルク、シリカ、クレー、カーボンファイバー、グラスファイバー、カーボンブラック、酸化チタン、酸化マグネシウム、ハイドロタルサイト、水酸化マグネシウム、酸化アンチモン、酸化亜鉛、カーボンブラック等が挙げられ、シリカ、カーボンブラックであることが好ましい。 As the filler, a known filler can be used, and specifically, calcium carbonate, talc, silica, clay, carbon fiber, glass fiber, carbon black, titanium oxide, magnesium oxide, hydrotalcite, and hydroxide. Examples thereof include magnesium, antimony oxide, zinc oxide and carbon black, and silica and carbon black are preferable.
充填剤の配合量はマレイミドに由来する構成単位を有する重合体100質量部に対して、15〜100質量部であってよい。20〜80質量部であることが好ましい。 The blending amount of the filler may be 15 to 100 parts by mass with respect to 100 parts by mass of the polymer having a structural unit derived from maleimide. It is preferably 20 to 80 parts by mass.
軟化剤としては、例えば潤滑油、プロセスオイル、コールタール、ヒマシ油、ステアリン酸、ステアリン酸カルシウム等を例示することができる。 Examples of the softener include lubricating oil, process oil, coal tar, castor oil, stearic acid, calcium stearate and the like.
軟化剤の配合量はマレイミドに由来する構成単位を有する重合体100質量部に対して、0.3〜10質量部であってよい。0.5〜5質量部であることが好ましい。 The blending amount of the softener may be 0.3 to 10 parts by mass with respect to 100 parts by mass of the polymer having a structural unit derived from maleimide. It is preferably 0.5 to 5 parts by mass.
老化防止剤としては、例えばアミン類、フォスフェート類、キノリン類、クレゾール類、フェノール類、ジチオカルバメート金属塩等があげられ、ジフェニルアミン誘導体、フェニレンジアミン誘導体等のアミン類が好ましい。 Examples of the antiaging agent include amines, phosphates, quinolines, cresols, phenols, dithiocarbamate metal salts and the like, and amines such as diphenylamine derivatives and phenylenediamine derivatives are preferable.
老化防止剤の配合量はマレイミドに由来する構成単位を有する重合体100質量部に対して、0.3〜10質量部であってよい。0.5〜5質量部であることが好ましい。 The blending amount of the antiaging agent may be 0.3 to 10 parts by mass with respect to 100 parts by mass of the polymer having a structural unit derived from maleimide. It is preferably 0.5 to 5 parts by mass.
更に、本発明の趣旨を逸脱しない範囲で、当該技術分野で通常行われているゴム、樹脂等とのブレンドを行うことも可能である。本発明に用いられるゴムを例示すれば、ブタジエンゴム、スチレン−ブタジエンゴム、イソプレンゴム、天然ゴム、アクリロニトリル−ブタジエンゴム、アクリロニトリル−ブタジエン−イソプレンゴム、エチレン−プロピレン−ジエンゴム、エピクロルヒドリンゴム等が挙げられ、また樹脂を例示すれば、PMMA(ポリメタクリル酸メチル)樹脂、PS(ポリスチレン)樹脂、PUR(ポリウレタン)樹脂、PVC(ポリ塩化ビニル)樹脂、EVA(エチレン/酢酸ビニル)樹脂、AS(スチレン/アクリロニトリル)樹脂、PE(ポリエチレン)樹脂等が挙げられる。 Further, it is also possible to blend with rubber, resin, etc., which are usually performed in the art, without departing from the spirit of the present invention. Examples of the rubber used in the present invention include butadiene rubber, styrene-butadiene rubber, isoprene rubber, natural rubber, acrylonitrile-butadiene rubber, acrylonitrile-butadiene-isoprene rubber, ethylene-propylene-diene rubber, epichlorohydrin rubber and the like. Examples of resins include PMMA (polymethylmethacrylate) resin, PS (polystyrene) resin, PUR (polyurethane) resin, PVC (polyvinyl chloride) resin, EVA (ethylene / vinyl acetate) resin, and AS (styrene / acrylonitrile). ) Resin, PE (polyethylene) resin and the like.
上記ゴム、樹脂の合計配合量は、本発明のマレイミドに由来する構成単位を有する重合体100質量部に対して、50質量部以下、好ましくは10質量部以下、より好ましくは1質量部以下である。 The total amount of the rubber and the resin to be blended is 50 parts by mass or less, preferably 10 parts by mass or less, and more preferably 1 part by mass or less with respect to 100 parts by mass of the polymer having the structural unit derived from the maleimide of the present invention. be.
本発明の架橋用組成物の配合方法としては、従来ポリマー加工の分野において利用されている任意の手段、例えばオープンロール、バンバリーミキサー、各種ニーダー類等を利用することができる。 As a method for blending the cross-linking composition of the present invention, any means conventionally used in the field of polymer processing, for example, an open roll, a Banbury mixer, various kneaders and the like can be used.
その配合手順としては、ポリマー加工の分野において行われている通常の手順で行うことができる。例えば、最初にポリマーのみを混練りし、次いで架橋剤以外の配合剤を投入したA練りコンパウンドを作製し、その後、架橋剤、架橋促進剤を投入するB練りを行う手順で行うことができる。 As the compounding procedure, it can be carried out by a usual procedure performed in the field of polymer processing. For example, it can be carried out by first kneading only the polymer, then preparing an A kneading compound containing a compounding agent other than the cross-linking agent, and then performing B-kneading by adding the cross-linking agent and the cross-linking accelerator.
本発明の架橋用組成物は、加熱することで架橋物とすることができる。架橋時間は温度によって異なるが、0.5〜300分の間で行われるのが普通である。架橋成型は架橋と成型を一体的に行う場合や、先に成型したアクリル共重合体含有組成物に改めて加熱することで架橋物とする場合のほか、先に加熱して架橋物を成型のために加工を施す場合のいずれでもよい。架橋成型の具体的な方法としては、金型による圧縮成型、射出成型、スチーム缶、エアーバス、赤外線、あるいはマイクロウェーブによる加熱等任意の方法を用いることができる。 The cross-linking composition of the present invention can be made into a cross-linked product by heating. The cross-linking time varies depending on the temperature, but is usually between 0.5 and 300 minutes. Cross-linking molding is performed in the case of integrally performing cross-linking and molding, in the case of forming a cross-linked product by heating the previously molded acrylic copolymer-containing composition again, or for molding the cross-linked product by heating first. It may be any of the cases where the processing is applied to. As a specific method of cross-linking molding, any method such as compression molding by a mold, injection molding, steam can, air bath, infrared rays, or heating by microwave can be used.
一般的なアクリル系エラストマーを用いて、十分に架橋を進行させた架橋物として得るには、160〜200℃で加熱することが必要となるが、本発明の架橋用組成物は幅広い温度範囲(例えば100℃〜200℃)で架橋物とすることができ、また、比較的低温(100〜150℃)でも十分に架橋を進行させた架橋物として得られる点でも好ましく、本発明の架橋用組成物を用いた低温(100〜150℃)における架橋材料の製造方法として記載することもできる。 In order to obtain a crosslinked product in which cross-linking has proceeded sufficiently using a general acrylic elastomer, it is necessary to heat at 160 to 200 ° C., but the cross-linking composition of the present invention has a wide temperature range ( For example, it can be obtained as a crosslinked product at (100 ° C. to 200 ° C.), and is also preferable in that it can be obtained as a crosslinked product in which cross-linking is sufficiently advanced even at a relatively low temperature (100 to 150 ° C.). It can also be described as a method for producing a crosslinked material at a low temperature (100 to 150 ° C.) using a material.
本発明を実施例、比較例により具体的に説明する。但し、本発明はこれらに限定されるものではない。
本実施例および比較例では、マレイミドに由来する構成単位を有する重合体の製造及び得られたマレイミドに由来する構成単位を有する重合体と架橋剤を含有する架橋用組成物、および架橋用組成物を用いて作製される架橋材料の物性を評価した。
The present invention will be specifically described with reference to Examples and Comparative Examples. However, the present invention is not limited thereto.
In this example and the comparative example, the production of a polymer having a structural unit derived from maleimide, the cross-linking composition containing the obtained polymer having a structural unit derived from maleimide and a cross-linking agent, and the cross-linking composition. The physical properties of the crosslinked material produced using the above were evaluated.
[実施例1〜4、比較例1〜4]
(重合体Aの製造)
温度計、攪拌装置、窒素導入管及び減圧装置を備えた重合反応器に、水200質量部、ポリオキシアルキレンアルキルエーテルリン酸エステル1.7質量部、モノマーとしてアクリル酸エチル49.2質量部、アクリル酸n−ブチル49.2質量部、マレイミド1.6質量部仕込み、減圧による脱気および窒素置換を繰り返して酸素を十分除去した後、アスコルビン酸ナトリウム0.1質量部および過硫酸カリウム0.1質量部を加えて常圧、常温下で乳化重合反応を開始させ、重合転化率が95%に達するまで反応を継続し、ヒドロキノンを0.0075質量部を添加して重合を停止した。得られた乳化重合液を硫酸ナトリウム水溶液で凝固させ、水洗、乾燥して重合体Aを得た。
[Examples 1 to 4, Comparative Examples 1 to 4]
(Production of Polymer A)
In a polymerization reactor equipped with a thermometer, agitator, nitrogen introduction tube and decompression device, 200 parts by mass of water, 1.7 parts by mass of polyoxyalkylene alkyl ether phosphate, 49.2 parts by mass of ethyl acrylate as a monomer, After 49.2 parts by mass of n-butyl acrylate and 1.6 parts by mass of maleimide were charged, degassing under reduced pressure and substitution with nitrogen were repeated to sufficiently remove oxygen, 0.1 part by mass of sodium ascorbate and potassium persulfate 0. 1 part by mass was added to start the emulsion polymerization reaction at normal pressure and normal temperature, the reaction was continued until the polymerization conversion rate reached 95%, and 0.0075 parts by mass of hydroquinone was added to terminate the polymerization. The obtained emulsion polymerization solution was coagulated with an aqueous sodium sulfate solution, washed with water and dried to obtain a polymer A.
[比較例2]
(アクリル共重合体Bの製造)
実施例1より、仕込むモノマーとその量を、アクリル酸エチル49.2質量部、アクリル酸n−ブチル49.2質量部、フマル酸モノエチル1.4質量部に変更した以外は、実施例1と同様に行い、アクリル共重合体Bを得た。
[Comparative Example 2]
(Production of Acrylic Copolymer B)
From Example 1, the monomer to be charged and the amount thereof were changed to 49.2 parts by mass of ethyl acrylate, 49.2 parts by mass of n-butyl acrylate, and 1.4 parts by mass of monoethyl fumarate. The same procedure was carried out to obtain an acrylic copolymer B.
[比較例3]
(アクリル共重合体Cの製造)
実施例1より、仕込むモノマーとその量を、アクリル酸エチル79.2質量部、アクリル酸n−ブチル19.0質量部およびモノクロロ酢酸ビニル1.4質量部に変更した以外は、実施例1と同様に行い、アクリル共重合体Cを得た。
[Comparative Example 3]
(Manufacture of Acrylic Copolymer C)
From Example 1, the monomer to be charged and the amount thereof were changed to 79.2 parts by mass of ethyl acrylate, 19.0 parts by mass of n-butyl acrylate and 1.4 parts by mass of vinyl monochloroacetate. The same procedure was carried out to obtain an acrylic copolymer C.
[比較例4]
(アクリル共重合体Dの製造)
実施例1より、仕込むモノマーとその量を、アクリル酸エチル52.1質量部、アクリル酸2-メトキシエチル23.0質量部、アクリル酸n−ブチル23.0質量部およびアリルグリシジルエーテル1.9質量部に変更した以外は、実施例1と同様に行い、アクリル共重合体Dを得た。
[Comparative Example 4]
(Manufacture of Acrylic Copolymer D)
From Example 1, the amount of the monomer to be charged is 52.1 parts by mass of ethyl acrylate, 23.0 parts by mass of 2-methoxyethyl acrylate, 23.0 parts by mass of n-butyl acrylate and 1.9 parts of allyl glycidyl ether. Acrylic copolymer D was obtained in the same manner as in Example 1 except that the parts were changed to parts by mass.
(架橋用組成物の製造)
まず、表1と表2に示す各配合剤を120℃のニーダーにて混練りし、A練りコンパウンドを作成した。このA練りコンパウンドを室温にてオープンロールにて混練りし、B練りコンパウンドを作成した。表中のAとはA練りコンパウンドの原料であり、Bとは、B練りコンパウンドを作成する際に、A練りコンパウンドに配合する原料を示すものである。表1、表2の配合剤に関する単位は質量部とする。
(Manufacturing of cross-linking composition)
First, each of the compounding agents shown in Tables 1 and 2 was kneaded with a kneader at 120 ° C. to prepare an A kneading compound. This A kneading compound was kneaded with an open roll at room temperature to prepare a B kneading compound. In the table, A is a raw material for the A kneading compound, and B is a raw material to be blended with the A kneading compound when the B kneading compound is prepared. The unit for the compounding agents in Tables 1 and 2 is parts by mass.
(架橋試験)
得られた架橋用組成物について、キュラストメータ「キュラストメーター7」(JSRトレーディング社製)を用いて180℃および130℃で10分間の加硫曲線を測定し最大値トルク(MH)を算出した。その結果を表1、2に示す。
(Crosslink test)
For the obtained cross-linking composition, the maximum torque (MH) was calculated by measuring the vulcanization curve for 10 minutes at 180 ° C and 130 ° C using a curast meter "Curast Meter 7" (manufactured by JSR Trading Co., Ltd.). bottom. The results are shown in Tables 1 and 2.
(未架橋シートの作製)
上記で得られた各架橋用組成物を用いて、厚さ2〜2.5mmの未架橋シートを作製した。
(Preparation of uncrosslinked sheet)
Using each of the cross-linking compositions obtained above, an uncross-linked sheet having a thickness of 2 to 2.5 mm was prepared.
(架橋材料(架橋物)の作製)
上記で得られた未架橋シートを130℃で30分プレス処理し、架橋物を得た。
(Preparation of cross-linked material (cross-linked product))
The uncrosslinked sheet obtained above was pressed at 130 ° C. for 30 minutes to obtain a crosslinked product.
(常態物性の試験)
得られた架橋物を用い、島津製作所社製 AGS-5KNYを用いて、引張試験および硬さ試験の評価を行った。引張試験はJIS K 6251、硬さ試験はJIS K6253に記載の方法に準じて行った。結果は表1、表2に示す。
(Test of normal physical characteristics)
Using the obtained crosslinked product, a tensile test and a hardness test were evaluated using AGS-5KNY manufactured by Shimadzu Corporation. The tensile test was performed according to the method described in JIS K 6251, and the hardness test was performed according to the method described in JIS K 6253. The results are shown in Tables 1 and 2.
上記、各試験方法より得られた実施例の結果を表1、比較例の試験結果を表2に示す。
各表中、架橋試験はキュラストメーターによる最大トルク、100%モジュラスは100%伸ばした時の応力、TBはJIS K6251の引張試験に定める強度、HSはJIS K6253の硬さ試験に定めるタイプAデュロメータ硬さをそれぞれ意味する。
Table 1 shows the results of the examples obtained by each of the above test methods, and Table 2 shows the test results of the comparative examples.
In each table, the cross-linking test is the maximum torque by the curast meter, 100% modulus is the stress when stretched 100%, TB is the strength specified in the tensile test of JIS K6251, HS is the type A durometer specified in the hardness test of JIS K6253. It means hardness respectively.
表中の配合剤について、以下記載する。
※1花王ケミカル社製「半硬化牛脂脂肪酸カリ石けん」
※2花王ケミカル社製「半硬化牛脂脂肪酸ソーダ石けん」
※3大内新興化学工業社製「ジメチルジチオカルバミン酸第二鉄」
※4大内新興化学工業社製「ジメチルジチオカルバミン酸亜鉛」
The compounding agents in the table are described below.
* 1 Kao Chemical Co., Ltd. "Semi-cured beef tallow fatty acid potassium soap"
* 2 Kao Chemical Co., Ltd. "Semi-cured beef tallow fatty acid soda soap"
* 3 "Ferric dimethyldithiocarbamate" manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.
* 4 "Zinc dimethyldithiocarbamate" manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.
表1で示すように、本発明の架橋用組成物はキュラストメーター試験において、低温時である130℃での最大トルク(MH)が大きく、比較例より早く架橋が進行していることから架橋特性に優れ、その架橋物は100%モジュラスや硬度(Hs)が大きいため、常態物性に優れることが実施例1〜4により示された。
比較例1において、マレイミドに由来する構成単位を有する重合体を用いた場合であっても、架橋剤を配合しない場合には架橋は進行しなかった。
比較例2において、架橋用組成物としての130℃での最大トルク(MH)が小さく、架橋材料としては、強度(TB)は大きいものの100%モジュラス及び硬度(Hs)が低く、架橋が十分進行していないと推察される。
比較例3、4は、架橋用組成物としての130℃での最大トルク(MH)が小さく、架橋材料としても、100%モジュラス、強度(TB)および硬度(Hs)が低く、架橋が十分進行していないと推察される。
As shown in Table 1, the cross-linking composition of the present invention has a large maximum torque (MH) at 130 ° C. at a low temperature in the curastometer test, and the cross-linking proceeds faster than in the comparative example. It was shown in Examples 1 to 4 that the crosslinked product is excellent in normal physical properties because it has excellent properties and its crosslinked product has a large 100% modulus and hardness (Hs).
In Comparative Example 1, even when a polymer having a structural unit derived from maleimide was used, cross-linking did not proceed unless a cross-linking agent was added.
In Comparative Example 2, the maximum torque (MH) at 130 ° C. as the cross-linking composition is small, and the cross-linking material has high strength (TB) but low 100% modulus and hardness (Hs), and the cross-linking proceeds sufficiently. It is presumed that it has not been done.
In Comparative Examples 3 and 4, the maximum torque (MH) at 130 ° C. as the cross-linking composition was small, and 100% modulus, strength (TB) and hardness (Hs) were low as the cross-linking material, and the cross-linking proceeded sufficiently. It is presumed that it has not been done.
本発明のマレイミドに由来する構成単位を有する重合体、及び分子内に少なくとも2以上の脱離基を含有する多官能性有機化合物を含有する架橋用組成物およびその架橋物は、低温短時間での架橋時における優れた常態物性から様々なゴム製品や樹脂製品の材料を低エネルギーで効率よく製造することが可能である。 The cross-linking composition containing the polymer having a structural unit derived from maleimide of the present invention and the polyfunctional organic compound containing at least two or more desorbing groups in the molecule and the cross-linked product thereof can be obtained at a low temperature for a short time. It is possible to efficiently manufacture various rubber products and resin product materials with low energy due to the excellent normal physical properties at the time of cross-linking.
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JP2005042113A (en) * | 2003-07-21 | 2005-02-17 | Clariant Gmbh | Fuel oil additive and additive-compounded fuel oil with improved low-temperature characteristic |
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