JPH01204937A - Plasticizer composition - Google Patents
Plasticizer compositionInfo
- Publication number
- JPH01204937A JPH01204937A JP2952488A JP2952488A JPH01204937A JP H01204937 A JPH01204937 A JP H01204937A JP 2952488 A JP2952488 A JP 2952488A JP 2952488 A JP2952488 A JP 2952488A JP H01204937 A JPH01204937 A JP H01204937A
- Authority
- JP
- Japan
- Prior art keywords
- plasticizer
- rubber
- formulas
- tables
- crown
- 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
- 239000004014 plasticizer Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 16
- 229920001971 elastomer Polymers 0.000 claims abstract description 21
- 239000005060 rubber Substances 0.000 claims abstract description 21
- 239000004033 plastic Substances 0.000 claims abstract description 19
- 229920003023 plastic Polymers 0.000 claims abstract description 19
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 11
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract description 5
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract description 5
- 238000004040 coloring Methods 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 abstract description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract description 2
- MBGYSHXGENGTBP-UHFFFAOYSA-N 6-(2-ethylhexoxy)-6-oxohexanoic acid Chemical compound CCCCC(CC)COC(=O)CCCCC(O)=O MBGYSHXGENGTBP-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 229920003048 styrene butadiene rubber Polymers 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- -1 xylenyl diphenyl phosphate Chemical compound 0.000 description 3
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 2
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- VDIFKDMFGPIVCQ-UHFFFAOYSA-N (2-tert-butylphenyl) diphenyl phosphate Chemical compound CC(C)(C)C1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 VDIFKDMFGPIVCQ-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- 241000283730 Bos primigenius Species 0.000 description 1
- GOJCZVPJCKEBQV-UHFFFAOYSA-N Butyl phthalyl butylglycolate Chemical compound CCCCOC(=O)COC(=O)C1=CC=CC=C1C(=O)OCCCC GOJCZVPJCKEBQV-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- ROPXFXOUUANXRR-YPKPFQOOSA-N bis(2-ethylhexyl) (z)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)\C=C/C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-YPKPFQOOSA-N 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- RXDDZPRSFAQJOC-UHFFFAOYSA-N butylbenzene;phthalic acid Chemical compound CCCCC1=CC=CC=C1.OC(=O)C1=CC=CC=C1C(O)=O RXDDZPRSFAQJOC-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MJOKHGMXPJXFTG-UHFFFAOYSA-N dihexyl nonanedioate Chemical compound CCCCCCOC(=O)CCCCCCCC(=O)OCCCCCC MJOKHGMXPJXFTG-UHFFFAOYSA-N 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 1
- QQVHEQUEHCEAKS-UHFFFAOYSA-N diundecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC QQVHEQUEHCEAKS-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- FJFYFBRNDHRTHL-UHFFFAOYSA-N tris(8-methylnonyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C(C(=O)OCCCCCCCC(C)C)=C1 FJFYFBRNDHRTHL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、可塑剤組成物に関する。さらに詳しくは、ゴ
ムまたはプラスチックスの導電性、帯電防止性を良好に
するメタロセン化合物を加えた可塑剤組成物に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to plasticizer compositions. More specifically, the present invention relates to a plasticizer composition containing a metallocene compound that improves the conductivity and antistatic properties of rubber or plastics.
（従来の技術）
ゴムあるいはプラスチックスは本来、体積固有抵抗の高
い絶縁材料であり、これまでこの絶縁性を利用して電気
電子技術の分野で広く応用されてきたが、同時に静電気
を帯電し、ホコリを吸着したり、ｌＩＰ電気を放電する
ときノイズを発生し、通信機、制ｆ２Ｉ１機を誤動作す
るなど問題も生じている。(Prior art) Rubber or plastics are originally insulating materials with high volume resistivity, and have been widely applied in the field of electrical and electronic technology by taking advantage of this insulating property. They attract dust and generate noise when discharging IP electricity, causing problems such as malfunctioning of communication equipment and F2I control equipment.
このため最近では、ゴムあるいはプラスチックスの体積
固有抵抗を低く導電性を付与することにより、帯電防止
性を良好にする試みが盛んになってきた。この様な傾向
は材料に新しくより高度な機能を与え付加価値を得よう
とする動きの現われであり、近い将来いろいろな形で電
気製品等の中に応用されるとか期待できる。ゴムあるい
はプラスチックスの静電気の帯電を防止する対策として
は、摩擦によって生じた静電気を素早く逃がしてやるた
めに、ゴムあるいはプラスチックスの体積固有抵抗を下
げることである。For this reason, recently, attempts have been made to improve antistatic properties by lowering the volume resistivity of rubber or plastics and imparting electrical conductivity to them. This trend is an expression of the movement to add new value to materials by giving them new and more advanced functions, and we can expect that they will be applied to various forms of electrical products in the near future. A measure to prevent rubber or plastics from being charged with static electricity is to lower the volume resistivity of the rubber or plastics in order to quickly dissipate static electricity generated by friction.
ゴムあるいはプラスチックスの体積固有抵抗を下げ導電
性、帯電防止性を良好にする方法としては、次の様なも
のなどがこれまで知られている。The following methods have been known as methods for lowering the volume resistivity of rubber or plastics to improve conductivity and antistatic properties.
■） ゴムあるいはプラスチックスに導電性の高い銀、
銅、ステンレ人 ニラゲル等の金属粉や金属繊維を添加
する方法。■) Rubber or plastic with highly conductive silver,
A method of adding metal powder or metal fibers such as copper and stainless steel.
２） ゴムあるいはプラスチックスにカーボンブラック
やカーボン繊維を添加する方法。2) A method of adding carbon black or carbon fiber to rubber or plastics.
３） ゴムあるいはプラスチックスに帯電防止剤と呼ば
れる界面活性剤やこれに類するものを添加する方法。3) A method of adding surfactants called antistatic agents or similar substances to rubber or plastics.
（発明の開示）
これらのゴムあるいはプラスチックスの体積固有抵抗を
下げ導電性、帯電防止性を良好にする方法は、次の様な
問題点もある。(Disclosure of the Invention) These methods of lowering the volume resistivity of rubber or plastics to improve conductivity and antistatic properties have the following problems.
１）の方法は体積固有抵抗を下げ帯電防止性は非常に効
果的であるが、自由な色に着色できず、メタリック色に
制限され、多量に添加しなければならず、また非常に高
価であり経済性に欠ける。Method 1) is very effective in reducing the volume resistivity and providing antistatic properties, but it cannot be colored in any desired color, is limited to metallic colors, must be added in large quantities, and is very expensive. However, it lacks economic efficiency.
２）の方法では、特にカーボンブラックが高価な導電性
付与剤としてよく使用されているが、色相が黒色に制限
されてしまうという欠点がある。In method 2), carbon black is often used as an expensive conductivity imparting agent, but it has the drawback that the hue is limited to black.
３）の方法は自由に着色できるという長所があるものの
、ｌ）や２）に比べると、十分な帯電防止効果が得られ
る物が見い出されていないのが実情である。Although method 3) has the advantage of being able to be colored freely, compared to methods 1) and 2), the reality is that no material has been found that provides a sufficient antistatic effect.
以上の記載から明らかなように、本発明の目的は、十分
な導電性、帯電防止性を良好にすると共に自由な着色を
可能とした、ゴムあるいはプラスチックス用可塑剤組成
物を提供することである。As is clear from the above description, an object of the present invention is to provide a plasticizer composition for rubber or plastics that has sufficient conductivity and good antistatic properties, and also allows for free coloring. be.
本発明者らは、十分な帯電防止効果が得られると共に自
由に着色できる点を改良すべく鋭意研究を重ねた。この
結果、ゴムあるいはプラスチックスに特定な化合物を含
有した可塑剤組成物を、単に添加する事により、体積固
有抵抗を下げ導電性、帯電防止性を良好にすると共に自
由に着色できる事を見いだし、本発明を完成するに至っ
た。The present inventors have conducted extensive research in order to improve the ability to obtain a sufficient antistatic effect and to freely color the material. As a result, we discovered that by simply adding a plasticizer composition containing a specific compound to rubber or plastics, it is possible to lower the volume resistivity, improve conductivity and antistatic properties, and freely color the material. The present invention has now been completed.
すなわち本発明の構成は下記の通りである。That is, the configuration of the present invention is as follows.
ゴムまたは／およびプラスチックス用可塑剤組成物にお
いて、メタロセン化合物を添加するこを特徴とする可塑
剤組成物ン
本発明の可塑剤組成物を用いるゴムまたは／およびプラ
スチックスは、ＳＢＲ（スチレン・ブタジェン・ラバー
）、 ＢＲ（ブタジェン、ラバー）、ＮＢＲにトリル・
ブタジェン・ラバー）、ＣＲ（クロロプレン・ラバー）
、ＥＰＴ（エチレン・プロピレン・コポリマー）などの
重合体、また塩化ビニル、ウレタン、酢酸ビニル、アク
リル酸エステル、塩化ビニリデンなどの単独重合体およ
びこれらの２Ｎ以上の混合物もしくは共重合体を挙げる
事ができ、さらにこれらを混合することかでき る。In the plasticizer composition for rubber and/or plastics, the plasticizer composition is characterized by adding a metallocene compound.・Rubber), BR (butadiene, rubber), NBR to trill・
butadiene rubber), CR (chloroprene rubber)
, EPT (ethylene propylene copolymer), homopolymers such as vinyl chloride, urethane, vinyl acetate, acrylic acid ester, vinylidene chloride, and mixtures or copolymers of 2N or higher. It is also possible to mix these.
本発明に用いる可塑剤は、ゴムあるいはプラスチックス
と相溶性が良く、しかも可塑化作用のある物質である０
例えば、フタル酸ジメチル（ＤＭＰ）、フタル酸ジエチ
ル（ＤＥＰ）、フタル酸ジブチル（ＤＢＰ＞、フタル酸
ブチルベンゼン（ＢＢＰ）、フタル酸ジヘプチル（ＤＨ
Ｐ）、フタル酸ジイソデシル（ＤＩＤＰ）、 フタル
酸ジイソノニル（ＤＩＮＰ）、フタル酸ジ２−エチルヘ
キシル（ＤＯＰ）、フタル酸ジｎ−オクチル（ＤｎＯＰ
＞、フタル酸ジトリデシル、フタル酸ジウンデシル（Ｄ
ＵＰ）、更に、フタル酸系混合エステル等各種フタル酸
系エステルおよびリン酸クレジルジフェニル、 リン酸
トリスクロロエチル、リン酸トリスジクロロプロピル、
リン酸トリクレジル、 リン酸トリエチル、リン酸ト
リキシレニル、リン酸キシレニルジフェニル、 リン酸
クレジルジフェニル、 リン酸オクチルジフェニル、
リン酸イソプロピルフエニルジフェニル、リン酸トリフ
ェニル、 リン酸ターシャリ−ブチルフエニルジフェニ
ル、 リン酸トリス（ベータクロロエチル）等各種リン
酸系エステルおよびオレイン酸ブチル、セバシン酸ジブ
チル、セバシン酸ジ２−エチルヘキシル等脂肪酸系エス
テルおよびアジピン酸ジイソブチル、アジピン酸ジイソ
ノニル、アジピン酸ジイソデシル、アジピン酸ジ２−エ
チルヘキシル、更に各種アジピン酸系混合エステル、お
よびトリメリット酸トリブチル、 トリメリット酸トリ
イソデシル、 トリメリット酸トリ２−エチルヘキシル
（ＴＯＴＭ）、 トリメリット酸トリーｎ−オクチル更
にトリメリット酸系混合エステルおよびアセチルクエン
酸トリブチル、ブチルフタリルブチルグリコレート、
２．２．４−）ジメチル−１，３−ベンタンジオールジ
イソブチレート（Ｃ３−１６）、フマル酸ジブチル、マ
レイン酸ジブチル、アゼライン酸ジｎ−ヘキシル、ドデ
カンニ酸ジオクチル、ドデカンニ酸ジ２−エチルヘキシ
ル、マレイン酸ジ２−エチルヘキシル、アゼライン酸ジ
ー２−エチルヘキシル、アジピン酸系ポリエステル、フ
タル酸系ポリエステル、セパチン酸系ポリエステル等の
可塑剤を例示することができ、ゴムあるいはプラスチッ
クスと相溶性のある可塑剤であればこれらに限ったもの
ではない。The plasticizer used in the present invention is a substance that has good compatibility with rubber or plastics and has a plasticizing effect.
For example, dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP>, butylbenzene phthalate (BBP), diheptyl phthalate (DH
P), diisodecyl phthalate (DIDP), diisononyl phthalate (DINP), di-2-ethylhexyl phthalate (DOP), di-n-octyl phthalate (DnOP)
>, ditridecyl phthalate, diundecyl phthalate (D
UP), and various phthalic acid esters such as phthalic acid mixed esters, cresyl diphenyl phosphate, trischloroethyl phosphate, trisdichloropropyl phosphate,
Tricresyl phosphate, triethyl phosphate, tricylenyl phosphate, xylenyl diphenyl phosphate, cresyl diphenyl phosphate, octyldiphenyl phosphate,
Isopropylphenyl diphenyl phosphate, triphenyl phosphate, tert-butylphenyl diphenyl phosphate, various phosphoric acid esters such as tris(betachloroethyl) phosphate, butyl oleate, dibutyl sebacate, di2-ethylhexyl sebacate fatty acid esters, diisobutyl adipate, diisononyl adipate, diisodecyl adipate, di-2-ethylhexyl adipate, various mixed esters of adipic acid, and tributyl trimellitate, triisodecyl trimellitate, tri-2-ethylhexyl trimellitate (TOTM), tri-n-octyl trimellitate, trimellitic acid mixed ester, acetyl tributyl citrate, butylphthalyl butyl glycolate,
2.2.4-) dimethyl-1,3-bentanediol diisobutyrate (C3-16), dibutyl fumarate, dibutyl maleate, di-n-hexyl azelaate, dioctyl dodecanoate, di2-ethylhexyl dodecanoate, Examples of plasticizers include di-2-ethylhexyl maleate, di-2-ethylhexyl azelaate, adipic acid polyester, phthalic acid polyester, and sepatic acid polyester, which are compatible with rubber or plastics. If so, it is not limited to these.
本発明において用いられるメタロセン化合物は、ビスシ
クロペンタジェニル金属化合物の内サンドイッチ構造か
らなる化合物の誘導体であり、Ｆｅ、Ｃｏ、Ｎｉ、Ｃｒ
などの金属錯体からなるものである。さらに好ましくは
、下記のメタロセン誘導体である。The metallocene compound used in the present invention is a derivative of a compound consisting of a sandwich structure within a biscyclopentagenyl metal compound, and includes Fe, Co, Ni, and Cr.
It consists of metal complexes such as. More preferred are the following metallocene derivatives.
Ｐ
ｐ
ｐ
但し、Ｃｐ：ペンタハプトシクロペンタジェニル基ｐｈ
・ヘキサハプトフェニル基
Ｂｅｎｚｏ−ｃｒｏｗｎ−ＮＨ：フェニル基にアミノ基
を持つベンゾ−クラウン−１５−エーテル−５である。P p p However, Cp: pentahaptocyclopentagenyl group ph
- Hexahaptophenyl group Benzo-crown-NH: Benzo-crown-15-ether-5 having an amino group in the phenyl group.
これらのメタロセン化合物は単独であるいは２種以上の
混合物として使用する事ができる０本発明に必要なメタ
ロセン化合物の添加量は特に限定−するものではないが
、好ましくは、可塑剤１００重量部に対しメタロセン化
合物０．Ｏ１〜１．０重量部であり、さらに好ましくは
０．０５〜０．２重量部である。These metallocene compounds can be used alone or as a mixture of two or more. The amount of the metallocene compound required for the present invention is not particularly limited, but is preferably in the amount of 100 parts by weight of the plasticizer. Metallocene compound 0. O1 to 1.0 parts by weight, more preferably 0.05 to 0.2 parts by weight.
可塑剤に対しメタロセン化合物が少なすぎては、体積固
有抵抗を低下させる効果が乏しく、多過ぎては耐熱性を
損ねたり、ブリード、ブルームを起こしたりするので好
ましくない。If the amount of the metallocene compound is too small relative to the plasticizer, the effect of lowering the volume resistivity will be poor, and if it is too large, it will impair heat resistance or cause bleeding or blooming, which is not preferable.
本発明の可塑剤組成物は、可塑剤にメタロセン化合物を
添加することにより、可塑剤組成物の体積固有抵抗を１
０〜１０ Ωｃｍ程度低下することがて゛き、目的とす
るゴムあるいはプラスチックスを十分に導電性を良好に
するとかでき、帯電防止を良好にするとができる。The plasticizer composition of the present invention has a volume resistivity of 1 by adding a metallocene compound to the plasticizer.
It can be reduced by about 0 to 10 Ωcm, and the target rubber or plastic can be sufficiently made to have good conductivity, and can be made to have good antistatic properties.
またメタロセン化合物特有の着色も、可塑剤にメタロセ
ン化合物を少量添加するので、可塑剤組成物としては着
色は僅かであり、さらにゴムあるいはプラスチックスに
本発明の可塑剤組成物を添加しても問題なく使用するこ
とができ、十分な導電性、帯電防止効果が得られると共
に自由に着色できる。In addition, the coloration peculiar to metallocene compounds is caused by adding a small amount of the metallocene compound to the plasticizer, so the coloring is slight for the plasticizer composition, and there is no problem even if the plasticizer composition of the present invention is added to rubber or plastics. It can be used freely, has sufficient conductivity and antistatic effect, and can be colored freely.
（実施例）
以下、実施例でもって本発明の効果を詳細に説明するが
、本発明はこれらに限定されるものではない。(Example) Hereinafter, the effects of the present invention will be explained in detail with reference to Examples, but the present invention is not limited thereto.
尚、本実施例に示す体積固有抵抗はＹＯＫＯＧＡＷＡ・
ＨＥＷＬＥＴＴ −ＰＡＣＫＲＤ社４３２９Ａ 型
）１１ＧＨＲ１１ＳＩＳＴＡＮＣ１’ＭＥＴＥＲ，電極
は液体セル２７６１型 Ｃ＝９０．０ＰＦＫ１０１７ｃ
ｍを使用して測定した。In addition, the volume resistivity shown in this example is YOKOGAWA・
HEWLETT-PACKRD company 4329A type
)11GHR11SISTANC1'METER, electrode is liquid cell type 2761 C=90.0PFK1017c
Measured using m.
実施例−９比較例−
可塑剤として、フタル酸ジ２−エチルヘキシル（ＤＯＰ
）、フタル酸ジヘプチル（ＤＨＰ）、フタル酸ジイソノ
ニル（ＤＩＮＰ）、トリメリット酸トリ２−エチルヘキ
シル（ＴＯＴＭ）を用い、メタロセン化合物として、先
に記載したＩ■■■ＶＶＩ■■■のメタロセン化合物を
用いた。Example-9 Comparative Example- As a plasticizer, di-2-ethylhexyl phthalate (DOP
), diheptyl phthalate (DHP), diisononyl phthalate (DINP), and tri-2-ethylhexyl trimellitate (TOTM), and as the metallocene compound, the metallocene compound of I■■■VVI■■■ described earlier was used. there was.
可塑剤１００重量部に対し所定量のメタロセン化合物を
溶解し、可塑剤組成物とした。この可塑剤組成物を液体
セルに導入し３０℃の恒温槽に３時間放置後、体積固有
抵抗を測定した。このときのメタロセン化合物の穫類、
添加量と体積固有抵抗の測定結果を表に示した。A predetermined amount of metallocene compound was dissolved in 100 parts by weight of plasticizer to prepare a plasticizer composition. This plasticizer composition was introduced into a liquid cell and left in a constant temperature bath at 30° C. for 3 hours, after which the volume resistivity was measured. The harvest of metallocene compounds at this time,
The measurement results of the amount added and the volume resistivity are shown in the table.
一以上一 同 上 野牛 克彦one or more one Same as above Wild Ox Katsuhiko
Claims (1)
おいて、メタロセン化合物を添加するこを特徴とする可
塑剤組成物。 ２）メタロセン化合物が、 I ▲数式、化学式、表等があります▼ II ▲数式、化学式、表等があります▼ III ▲数式、化学式、表等があります▼ IV ▲数式、化学式、表等があります▼ Ｖ ▲数式、化学式、表等があります▼ VI ▲数式、化学式、表等があります▼ VII ▲数式、化学式、表等があります▼ VIII ▲数式、化学式、表等があります▼ IX ▲数式、化学式、表等があります▼ 但し、Ｃｐ：ペンタハプトシクロペンタジエニル基 Ｐｈ：ヘキサハプトフエニル基 Ｂｅｎｚｏ−ｃｒｏｗｎ−ＮＨ：フェニル基にアミノ基
を持つベンゾ−クラウン−１５−エーテル−５であり、
このメタロセン化合物を０．０１〜１．０重量部添加し
た特許請求の範囲第１項記載の組成物。[Scope of Claims] 1) A plasticizer composition for rubber and/or plastics, characterized in that a metallocene compound is added thereto. 2) Metallocene compounds are I ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ II ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ III ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ IV ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ V ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ VI ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ VII ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ VIII ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ IX ▲ Mathematical formulas, chemical formulas, There are tables etc. ▼ However, Cp: pentahaptocyclopentadienyl group Ph: hexahaptophenyl group Benzo-crown-NH: benzo-crown-15-ether-5 having an amino group on the phenyl group,
The composition according to claim 1, to which 0.01 to 1.0 parts by weight of this metallocene compound is added.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2952488A JPH01204937A (en) | 1988-02-10 | 1988-02-10 | Plasticizer composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2952488A JPH01204937A (en) | 1988-02-10 | 1988-02-10 | Plasticizer composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01204937A true JPH01204937A (en) | 1989-08-17 |
Family
ID=12278494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2952488A Pending JPH01204937A (en) | 1988-02-10 | 1988-02-10 | Plasticizer composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01204937A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05271496A (en) * | 1992-03-24 | 1993-10-19 | Sumitomo Rubber Ind Ltd | Rubber composition |
| US5989460A (en) * | 1994-11-21 | 1999-11-23 | Garland Floor Co. | Electrically conductive coating |
-
1988
- 1988-02-10 JP JP2952488A patent/JPH01204937A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05271496A (en) * | 1992-03-24 | 1993-10-19 | Sumitomo Rubber Ind Ltd | Rubber composition |
| US5989460A (en) * | 1994-11-21 | 1999-11-23 | Garland Floor Co. | Electrically conductive coating |
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