JPH0428745A - Chlorine-containing resin composition having excellent antistatic property - Google Patents
Chlorine-containing resin composition having excellent antistatic propertyInfo
- Publication number
- JPH0428745A JPH0428745A JP13471490A JP13471490A JPH0428745A JP H0428745 A JPH0428745 A JP H0428745A JP 13471490 A JP13471490 A JP 13471490A JP 13471490 A JP13471490 A JP 13471490A JP H0428745 A JPH0428745 A JP H0428745A
- Authority
- JP
- Japan
- Prior art keywords
- group
- chlorine
- carbon atoms
- containing resin
- alkyl
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000000460 chlorine Substances 0.000 title claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 title claims abstract description 23
- 239000011342 resin composition Substances 0.000 title claims description 7
- -1 quaternary ammonium compound perchloric acid salt Chemical class 0.000 claims abstract description 74
- 229920005989 resin Polymers 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 12
- 230000000740 bleeding effect Effects 0.000 abstract description 4
- 229920000915 polyvinyl chloride Polymers 0.000 abstract description 3
- 239000004800 polyvinyl chloride Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 description 15
- 239000002216 antistatic agent Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 241000156978 Erebia Species 0.000 description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 8
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 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 description 5
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 229920006280 packaging film Polymers 0.000 description 3
- 239000012785 packaging film Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000006023 1-pentenyl group Chemical group 0.000 description 2
- LVAGMBHLXLZJKZ-UHFFFAOYSA-N 2-o-decyl 1-o-octyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC LVAGMBHLXLZJKZ-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000009408 flooring Methods 0.000 description 2
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- GOLSFPMYASLXJC-UHFFFAOYSA-N 2-(dimethylamino)ethyl acetate Chemical compound CN(C)CCOC(C)=O GOLSFPMYASLXJC-UHFFFAOYSA-N 0.000 description 1
- VXLCSWZJLRTYDR-UHFFFAOYSA-N 2-acetyloxyethyl-benzyl-dimethylazanium Chemical compound CC(=O)OCC[N+](C)(C)CC1=CC=CC=C1 VXLCSWZJLRTYDR-UHFFFAOYSA-N 0.000 description 1
- WUKXCOUDBACATH-UHFFFAOYSA-N 2-acetyloxyethyl-butyl-dimethylazanium Chemical compound CCCC[N+](C)(C)CCOC(C)=O WUKXCOUDBACATH-UHFFFAOYSA-N 0.000 description 1
- GNKMDDLLHSOOEF-UHFFFAOYSA-N 2-acetyloxyethyl-dodecyl-dimethylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)CCOC(C)=O GNKMDDLLHSOOEF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- WYRIQSJBDPBLDQ-UHFFFAOYSA-O 2-hydroxyethyl-dimethyl-[3-(octadecanoylamino)propyl]azanium Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCC[N+](C)(C)CCO WYRIQSJBDPBLDQ-UHFFFAOYSA-O 0.000 description 1
- OCAPHIRVDIMADR-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-octylazanium Chemical compound CCCCCCCC[N+](C)(C)CCO OCAPHIRVDIMADR-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- HBVZRPAKZOLBPL-UHFFFAOYSA-N O-Acetylethanolamine Chemical compound CC(=O)OCCN HBVZRPAKZOLBPL-UHFFFAOYSA-N 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- 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 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 1
- GOBKHNHHHSPHEX-UHFFFAOYSA-N bis[2-(2-butoxyethoxy)ethyl] benzene-1,2-dicarboxylate Chemical compound CCCCOCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCOCCCC GOBKHNHHHSPHEX-UHFFFAOYSA-N 0.000 description 1
- SCABKEBYDRTODC-UHFFFAOYSA-N bis[2-(2-butoxyethoxy)ethyl] hexanedioate Chemical compound CCCCOCCOCCOC(=O)CCCCC(=O)OCCOCCOCCCC SCABKEBYDRTODC-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- SQNNHEYXAJPPKH-UHFFFAOYSA-N chloroethene;prop-2-enoic acid Chemical compound ClC=C.OC(=O)C=C SQNNHEYXAJPPKH-UHFFFAOYSA-N 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- QBQLPWLODYZCLE-UHFFFAOYSA-M dodecyl-(2-hydroxyethyl)-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CCO QBQLPWLODYZCLE-UHFFFAOYSA-M 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035936 sexual power Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- YETJDUSSMZWBME-UHFFFAOYSA-N tris[2-(2-butoxyethoxy)ethyl] phosphate Chemical compound CCCCOCCOCCOP(=O)(OCCOCCOCCCC)OCCOCCOCCCC YETJDUSSMZWBME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明はアシル化された過塩素酸の第四級アンモニウム
塩化合物を添加してなる、帯電防止性に優れた塩素含有
樹脂組成物に関し、詳しくは、過塩素酸のアシル化され
た脂肪族第四級アンモニウム塩化合物を添加してなる、
特に帯電防止性及びブリード性の改良された塩素含有樹
脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a chlorine-containing resin composition with excellent antistatic properties, which is prepared by adding an acylated quaternary ammonium salt compound of perchloric acid. It is formed by adding an acylated aliphatic quaternary ammonium salt compound,
In particular, it relates to a chlorine-containing resin composition with improved antistatic properties and bleed properties.
ポリ塩化ビニル樹脂等の塩素含有樹脂は、可塑剤を比較
的多量に加えた軟質製品あるいは可塑剤を比較的少量加
えたいわゆる半硬質製品として、各種の包装フィルムあ
るいは容器、農業用フィルム、シート、床材、壁材等に
広く使用されている。Chlorine-containing resins such as polyvinyl chloride resins are used in various packaging films and containers, agricultural films, sheets, Widely used for flooring, walling, etc.
これらの塩素含有樹脂は一般に電気絶縁性が良好であり
、電線被覆材料等の電気絶縁性を要求される分野におい
ては好ましい性質ではあるが、摩擦により静電気を蓄積
するため、例えば、工場、電算機室等の間仕切り、ＩＣ
の運搬・保護用のケース、電子通信関係の被覆材等の包
装用フィルムやシートに用いる場合にはいわゆる静電気
障害を引き起こすことが多い。These chlorine-containing resins generally have good electrical insulation properties, which is desirable in fields that require electrical insulation properties such as wire coating materials, but because they accumulate static electricity due to friction, they are used in factories, computers, etc. Room partitions, IC
When used in packaging films and sheets such as cases for transporting and protecting electronic communications, covering materials for electronic communication, etc., it often causes so-called static electricity damage.
また、塩素含有樹脂を床材として用いる場合にも静電気
により汚れを吸着し、外観を損なうという不利益もあっ
た。Further, when using a chlorine-containing resin as a flooring material, there is also the disadvantage that it attracts dirt due to static electricity, impairing its appearance.
更に、塩素含有樹脂は水との親和性に乏しいため、食品
包装用フィルムあるいは容器、農業用フィルム等に用い
た場合に表面に水滴が付着し、曇りを生じる欠点もあり
、塩素含有樹脂の帯電を防止することが要望されていた
。Furthermore, chlorine-containing resins have poor affinity with water, so when used in food packaging films, containers, agricultural films, etc., water droplets may adhere to the surface, causing cloudiness. It was desired to prevent this.
これらの欠点を解消するために、例えば、特公昭３９−
２１１１４号公報にはエーテルアルコールのエステルを
可塑剤として用いることが提案されているが、その効果
は全く不充分であり、実用上は満足できるものではなか
った。In order to eliminate these drawbacks, for example,
Although Japanese Patent No. 21114 proposes the use of an ether alcohol ester as a plasticizer, the effect was completely insufficient and was not satisfactory in practice.
このため、一般には、各種の帯電防止剤を塩素含有樹脂
に添加あるいは塗布し、帯電防止性を改良しようとする
試みがなされているが、これらの帯電防止剤の多くは塩
素含有樹脂の熱安定性を著しく低下させるためその使用
に制限を受けていたのが実情である。For this reason, attempts have generally been made to improve the antistatic properties by adding or coating various antistatic agents to chlorine-containing resins, but many of these antistatic agents do not improve the thermal stability of chlorine-containing resins. The reality is that its use has been restricted because it significantly reduces sexual performance.
例えば、特公昭４０−７３６６号公報には、汎用の可塑
剤であるジオクチルフタレートを配合した塩化ビニル樹
脂に第四級アンモニウム塩型の帯電防止剤を添加した場
合の影響が詳細に記載されており、トリメチル・ドデシ
ルアンモニウムクロライド、ジメチル・ヒドロキシエチ
ル・ドデシルアンモニウムブロマイド等の第四級アンモ
ニウムハライド系の帯電防止剤は塩化ビニル樹脂の熱分
解を著しく促進すること、陰イオンとして過塩素酸また
は有機スルホン酸のアニオンを用いた第四級アンモニウ
ム塩型の帯電防止剤は悪影響が小さく、特に有機スルホ
ン酸アニオンを用いた化き物は悪影響が極めて小さいこ
とが記載されている。For example, Japanese Patent Publication No. 40-7366 describes in detail the effects of adding a quaternary ammonium salt type antistatic agent to vinyl chloride resin blended with dioctyl phthalate, a general-purpose plasticizer. , quaternary ammonium halide antistatic agents such as trimethyl dodecylammonium chloride and dimethyl hydroxyethyl dodecylammonium bromide significantly accelerate thermal decomposition of vinyl chloride resin, and perchloric acid or organic sulfonic acid as anions. It is described that quaternary ammonium salt type antistatic agents using the anion have little adverse effect, and in particular, compounds using organic sulfonic acid anions have very little adverse effect.
しかしながら、上記公報記載の有機スルホン酸アニオン
を用いた化合物は塩素含有樹脂の加熱による着色変化が
極めて大きく、しかも帯電防止効果も不十分であり、ま
た過塩素酸アニオンを用いた第四級アンモニウム塩型の
帯電防止剤を用いた場合においても熱安定性の低下は無
視できるものではなく、実際上は満足できるものではな
かった。However, the compound using an organic sulfonic acid anion described in the above-mentioned publication shows an extremely large color change due to heating of the chlorine-containing resin, and also has insufficient antistatic effect, and the quaternary ammonium salt using a perchlorate anion Even when a type of antistatic agent was used, the decrease in thermal stability was not negligible and was not satisfactory in practice.
このため、熱安定性に悪影響を及ぼさないノニオン系の
帯電防止剤を使用することも提案されており、例えば、
特公昭４４−２２６１６号公報にはエーテルアルコール
のエステルとノニオン系の帯電防止剤を併用することに
より、その帯電防止性がさらに改善されることが記載さ
れているが、その改良効果は未だ満足しえるものではな
く、また、エーテル系のため、樹脂との相溶性が小さく
、ブリードする事も懸念され、改善することが強く望ま
れていた。For this reason, it has been proposed to use nonionic antistatic agents that do not adversely affect thermal stability; for example,
Japanese Patent Publication No. 44-22616 describes that the antistatic property can be further improved by using an ether alcohol ester and a nonionic antistatic agent in combination, but the improvement effect is still not satisfactory. In addition, since it is an ether type, it has low compatibility with resins, and there is a concern that it may bleed, so there was a strong desire to improve it.
本発明者等は、上記現状に鑑み、帯電防止性及び熱安定
性が良好であり、しかも、ブリード性の優れた塩素含有
樹脂組成物を得るために鋭意検討を重ねた結果、アシル
化された過塩素酸の脂肪族第四級アンモニウム塩化合物
を使用した場合には帯電防止性及び熱安定性に優れるば
かりが、ブリード性に優れることを見出し、本発明に到
達した。In view of the above-mentioned current situation, the present inventors have conducted intensive studies to obtain a chlorine-containing resin composition that has good antistatic properties and thermal stability, and has excellent bleeding properties. It has been found that when an aliphatic quaternary ammonium salt compound of perchloric acid is used, it not only has excellent antistatic properties and thermal stability, but also has excellent bleeding properties, and has thus arrived at the present invention.
即ち、本発明は塩素含有樹脂１００重量部に対し、次の
一般式（１）で表されるアシル化された過塩素酸の第四
級アンモニウム塩化合物０．０１〜５重量部を添加して
なる塩素含有樹脂組成物を提供するものである。That is, in the present invention, 0.01 to 5 parts by weight of an acylated quaternary ammonium salt compound of perchloric acid represented by the following general formula (1) is added to 100 parts by weight of the chlorine-containing resin. The present invention provides a chlorine-containing resin composition.
（式中、Ｒ１は炭素原子数４〜２２のアルキル基、炭素
原子数７〜２０のアラルキル基または基Ｒ’Ｃ０ＮＨＲ
”−を示し、Ｒ゛は炭素原子数１〜２０のアルキル基ま
たはアルケニル基を示し、Ｒ”は炭素原子数１〜１０の
アルキレン基を示し、Ｒ２及、びＲ３は各々独立に炭素
原子数１〜２０のアラキル基または（Ａ−〇ｈＸを示し
、Ａは炭素数２〜〜４のアルキレン基を示し、Ｘは水素
原子、アルキル基、アリール基または−ＣＲ４を示し、
ｎは１〜２０の整数を示し、Ｒ４は炭素原子数１〜２０
のアルキル基を示す。）
以下、上記要旨をもってなる本発明について詳述する。(In the formula, R1 is an alkyl group having 4 to 22 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a group R'C0NHR
``-'', R'' represents an alkyl group or alkenyl group having 1 to 20 carbon atoms, R'' represents an alkylene group having 1 to 10 carbon atoms, and R2 and R3 each independently have a number of carbon atoms. 1 to 20 aralyl group or (A-〇hX, A represents an alkylene group having 2 to 4 carbon atoms, X represents a hydrogen atom, an alkyl group, an aryl group, or -CR4,
n represents an integer of 1 to 20, and R4 has 1 to 20 carbon atoms.
represents an alkyl group. ) Hereinafter, the present invention having the above-mentioned summary will be explained in detail.
上記式中１、Ｒ５で表される炭素原子数４〜２２のアル
キル基としては、ブチル基、第ニブチル基、第三ブチル
基、イソブチル基、アミル基、第三アミル基、ヘキシル
基、ヘプチル基、オクチル基、イソオクチル基、２−エ
チルヘキシル基、第三オクチル基、ノニル基、第三ノニ
ル基、デシル基、イソデシル基、ドデシル基、テトラデ
シル基、ヘキサデシル基、オクタデシル基、エイコシル
基、トコシル基等が挙げられ、炭素原子数７〜２０のア
ラルキル基としては、ベンジル基、ジフェニルメチル基
、シンナミル基、フェネチル基、スチリル基等が挙げら
れる。Examples of the alkyl group having 4 to 22 carbon atoms represented by 1 and R5 in the above formula include butyl group, nibutyl group, tertiary butyl group, isobutyl group, amyl group, tertiary amyl group, hexyl group, heptyl group. , octyl group, isooctyl group, 2-ethylhexyl group, tertiary octyl group, nonyl group, tertiary nonyl group, decyl group, isodecyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, eicosyl group, tocosyl group, etc. Examples of the aralkyl group having 7 to 20 carbon atoms include a benzyl group, a diphenylmethyl group, a cinnamyl group, a phenethyl group, and a styryl group.
Ｒ′、Ｒ２、Ｒ３及びＲ４で表される炭素原子数１〜２
０のアルキル基としては、メチル基、エチル基、プロピ
ル基、イソプロピル基、ブチル基、第ニブチル基、第三
ブチル基、イソブチル基、アミル基、第三アミル基、ヘ
キシル基、ヘプチル基、オクチル基、イソオクチル基、
２−エチルヘキシル基、第三オクチル基、ノニル基、第
三ノニル基、デシル基、イソデシル基、ドデシル基、テ
トラデシル基、ヘキサデシル基、オクタデシル基、エイ
コシル基等が挙げられ、アルケニル基としては、ビニル
基、１−プロペニル基、２−プロペニル基、１−プテニ
ル基、２−ブテニル基、３−ブテニル基、１−ペンテニ
ル基、１−ペンテニル基、２−ペンテニル基、３−ペン
テニル基、４−ペンテニル基、１−へブテニル基、２−
へブテニル基、１−ノネニル基、３−ノネニル基、８−
ノネニルｉ、１−ウンデエニル基、２−ウンデエニル基
、２−ウンデエニル基、４−ウンデエニル基、１０−ウ
ンデエニル基、３−トリデカニル基、４−トリデカニル
基、８−トリデカニル基、１−ペンタデセニル基、６−
ペンタデセニル基、８−ペンタデ基セニル基、５−へブ
タデセニル基、８−へブタデセニル基、１０−ノナデカ
ニル基、８−へニコサニル基、１０−へニコサニル基等
が挙げられ、Ｒ”で表される炭素原子数１〜１０のアル
キレン基としては、エチレン基、プロピレン基、トリメ
チレン基、ブチレン基、イソブチレン基、テトラメチレ
ン基、ペンタメチレン基、ヘキサメチレン基等が挙げら
れ、Ａで表される炭素数２〜４のアルキレン基としては
、エチレン基、プロピレン基、ブチレン基、イソブチレ
ン基等が挙げられ、Ｘで表されるアルキル基としては、
メチル基、エチル基、プロピル基、イソプロピル基、ブ
チル基、第ニブチル基、第三ブチル基、イソブチル基、
アミル基、第三アミル基、ヘキシル基、ヘプチル基、オ
クチル基、イソオクチル基、２７エチルヘキシル基、第
三オクチル基、ノニル基等が挙げられ、アリール基とし
ては、フェニル基、メチルフェニル基、ジメチルフェニ
ル基エチルフェニル基、ジエチルフェニル基、プロピル
フェニル基、ジプロピルフェニル基、イソプロピルフェ
ニル基、ジイソプロピルフェニル基、ブチルフェニル基
、イソブチルフェニル基、オクチルフェニル基、ノニル
フェニル基、ドデシルフェニル基、メトキシフェニル基
、エトキシフェニル基、プロポキシフェニル基等が挙げ
られる。1 to 2 carbon atoms represented by R', R2, R3 and R4
Examples of the alkyl group of 0 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, nibutyl group, tertiary butyl group, isobutyl group, amyl group, tertiary amyl group, hexyl group, heptyl group, octyl group. , isooctyl group,
Examples include 2-ethylhexyl group, tertiary octyl group, nonyl group, tertiary nonyl group, decyl group, isodecyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, eicosyl group, etc. As the alkenyl group, vinyl group , 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group , 1-hebutenyl group, 2-
Hebutenyl group, 1-nonenyl group, 3-nonenyl group, 8-
Nonenyl i, 1-undenyl group, 2-undenyl group, 2-undenyl group, 4-undenyl group, 10-undenyl group, 3-tridecanyl group, 4-tridecanyl group, 8-tridecanyl group, 1-pentadecenyl group, 6-
Examples include pentadecenyl group, 8-pentadecenyl group, 5-hebutadecenyl group, 8-hebutadecenyl group, 10-nonadecanyl group, 8-henicosanyl group, 10-henicosanyl group, and the carbon represented by R'' Examples of the alkylene group having 1 to 10 atoms include an ethylene group, a propylene group, a trimethylene group, a butylene group, an isobutylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, and the carbon number represented by A is 2. Examples of the alkylene group of ~4 include ethylene group, propylene group, butylene group, isobutylene group, etc., and the alkyl group represented by X is:
Methyl group, ethyl group, propyl group, isopropyl group, butyl group, nibutyl group, tertiary butyl group, isobutyl group,
Examples of the aryl group include an amyl group, a tertiary amyl group, a hexyl group, a heptyl group, an octyl group, an isooctyl group, a 27 ethylhexyl group, a tertiary octyl group, a nonyl group, and examples of the aryl group include a phenyl group, a methylphenyl group, and a dimethylphenyl group. Group ethylphenyl group, diethylphenyl group, propylphenyl group, dipropylphenyl group, isopropylphenyl group, diisopropylphenyl group, butylphenyl group, isobutylphenyl group, octylphenyl group, nonylphenyl group, dodecylphenyl group, methoxyphenyl group, Examples include ethoxyphenyl group and propoxyphenyl group.
上記一般式（１）で表されるアシル化された過塩素酸の
四級アンモニウム塩型帯電防止側は、市販の水酸基を有
する過塩素酸の第四級アンモニウム塩型化合物、または
水酸基を有する第四級アンモニウムヒドロキシドと過塩
素酸を反応させた化合物に酸無水物を反応させることに
よって容易に合成することができる。The antistatic side of the acylated quaternary ammonium salt of perchloric acid represented by the above general formula (1) is a commercially available quaternary ammonium salt type compound of perchloric acid having a hydroxyl group, or a quaternary ammonium salt type compound of perchloric acid having a hydroxyl group, or It can be easily synthesized by reacting a compound obtained by reacting quaternary ammonium hydroxide and perchloric acid with an acid anhydride.
上記一般式（１）で表されるアシル化された過塩素酸の
第四級アンモニウム塩としては、ジメチル・ｎ−ブチル
・−β−アセトキシエチルアンモニウムバークロレート
、ル・ｎ−ブチル・−α−メチル−β−アセトキシエチ
ルアンモニウムバークロレート、ジメチル・２−エチル
ヘキシル・−β−アセトキシエチルアンモニウムバーク
ロレート、ジメチル・２−エチルヘキシル・−α−メチ
ル−β−アセトキシエチルアンモニウムバークロレート
、ジメチル・ｎ−オクチル・−β−アセトキシエチルア
ンモニウムバークロレート、ジメチル・ｎ−オクチル・
−α−メチル−β−アセトキジエチルアンモニウムバー
クロレート、ジメチル・ｎ−デシル・−β−アセトキシ
エチルアンモニウムバークロレート、ジメチル・ドデシ
ル・−β−アセトキシエチルアンモニウムバークロレー
ト、ジメチル・ドデシル・−α−メチル−β−アセトキ
シエチルアンモニウムバークロレート、ジメチル・ステ
アリル・−β−アセトキシエチルアンモニウムバークロ
レート、ジメチル・ベンジル・−β−アセトキシエチル
アンモニウムバークロレート、ジメチル・ベンジル・−
α−メチル−β−アセトキシエチルアンモニウムバーク
ロレート、ジメチル・２−エチルヘキシル・アセトキシ
エチルオキシエチルアンモニウムバークロレート、ジメ
チル・ステアリル・アセトキシエチルオキシエチルアン
モニウムバークロレート、ジメチル・ベンジル・アセト
キシエチルオキシエチルアンモニウムバークロレート、
ラウラミドプロピルジメチルーβ−アセトキシエチルア
ンモニウムバークロレート、ステアラミドプロピルジメ
チル−β−アセトキシエチルアンモニウムバークロレー
ト、ステアラミドプロピルジメチル−α−メチル−β−
アセトキシエチルアンモニウムバークロレート、オレア
ラミドプロビルジメチル−β−アセトキシエチルアンモ
ニウムバークロレート等があげられる。Examples of the quaternary ammonium salt of acylated perchloric acid represented by the above general formula (1) include dimethyl n-butyl -β-acetoxyethylammonium verchlorate, n-butyl -α- Methyl-β-acetoxyethylammonium verchlorate, dimethyl 2-ethylhexyl-β-acetoxyethylammonium verchlorate, dimethyl 2-ethylhexyl-α-methyl-β-acetoxyethylammonium verchlorate, dimethyl n-octyl -β-acetoxyethylammonium verchlorate, dimethyl n-octyl
-α-Methyl-β-acetoxyethylammonium verchlorate, dimethyl n-decyl-β-acetoxyethylammonium verchlorate, dimethyl dodecyl-β-acetoxyethylammonium verchlorate, dimethyl dodecyl-α-methyl -β-acetoxyethylammonium verchlorate, dimethyl stearyl-β-acetoxyethylammonium verchlorate, dimethyl benzyl-β-acetoxyethylammonium verchlorate, dimethyl benzyl-
α-Methyl-β-acetoxyethylammonium verchlorate, dimethyl 2-ethylhexyl acetoxyethyloxyethylammonium verchlorate, dimethyl stearyl acetoxyethyloxyethylammonium verchlorate, dimethyl benzyl acetoxyethyloxyethylammonium verchlorate,
Lauramidopropyldimethyl-β-acetoxyethylammonium verchlorate, stearamidepropyldimethyl-β-acetoxyethylammonium verchlorate, stearamidepropyldimethyl-α-methyl-β-
Examples include acetoxyethylammonium verchlorate, olearamideprobyl dimethyl-β-acetoxyethylammonium verchlorate, and the like.
上記アシル化された過塩素酸の第四級アンモニウム塩の
配合量は、塩素含有樹脂１００重量部に対し０．０１〜
５重量部、より好ましくは０．１〜３重量部である。The amount of the above-mentioned acylated quaternary ammonium salt of perchloric acid is 0.01 to 100 parts by weight per 100 parts by weight of the chlorine-containing resin.
It is 5 parts by weight, more preferably 0.1 to 3 parts by weight.
本発明で用いられる塩素含有樹脂としては、ポリ塩化ビ
ニル、ポリ塩化ビニリデン、塩化ビニル酢酸ビニル共重
合体、塩化ビニル−エチレン共重合体、塩化ビニル−ア
クリル酸エステル共重合体あるいは上記の含塩素樹脂と
ＡＢＳ樹脂、ＭＢＳ樹脂、ＮＢＲ等とのブレンド物をあ
げることができる。The chlorine-containing resin used in the present invention includes polyvinyl chloride, polyvinylidene chloride, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-acrylic acid ester copolymer, or the above-mentioned chlorine-containing resin. Blends with ABS resin, MBS resin, NBR, etc. can be mentioned.
本発明の帯電防止性に優れた塩素含有樹脂は、特に可塑
剤を含有する半硬質または軟質に有効である。用いられ
る可塑剤としては、例えば、フタル酸エステル可塑剤（
ジブチルフタレート、ジ・２−エチルヘキシル・フタレ
ート、ビス（ブトキシエトキシエチル）フタレート、ジ
・ｎ−オクチル・フタレート、ジノニル・フタレート、
ジデシル・フタレート、ジイソデシル・フタレート、ｎ
オクチル・ｎ−デシル・フタレート、ブチルベンジルフ
タレート等）、リン酸エステル可塑剤（トリクレジル・
ホスフェート、トリー２−エチルヘキシル・ホスフェー
ト、トリス（ブトキシエトキシエチル）ホスフェート、
トリフェニル・ホスフェート、２−エチルへキシルジフ
ェニル・ホスフェート等）、アジピン酸エステル可塑剤
（ジ・２−エチルヘキシル・アジペート、ビス（ブトキ
シエトキシエチル）アジペート、ジイソデシル・アジペ
ート等）、セパチン酸エステル可塑剤（ジブチル・セバ
ケート、ジ・２−エチルヘキシル・セバケート等）、ア
ゼライン酸エステル可塑剤（ジ・２−エチルヘキシル・
アゼレート等）、トリメリット酸エステル可塑剤（トリ
ブチルトリメリテート、トリ・２−エチルヘキシル・ト
リメリテート等）、ポリエステル型可塑剤（ポリプロピ
レン・アジペート、ポリプロピレン・セバケート等）エ
ポキシ基型可塑剤（エポキシ化大豆油、エポキシ化アマ
ニ油等）、塩素化パラフィン、塩素化脂肪酸エステル等
を挙げることができる。The chlorine-containing resin excellent in antistatic properties of the present invention is particularly effective for semi-rigid or soft resins containing plasticizers. Examples of plasticizers used include phthalate plasticizers (
Dibutyl phthalate, di-2-ethylhexyl phthalate, bis(butoxyethoxyethyl) phthalate, di-n-octyl phthalate, dinonyl phthalate,
Didecyl phthalate, diisodecyl phthalate, n
octyl n-decyl phthalate, butylbenzyl phthalate, etc.), phosphate ester plasticizers (tricresyl,
phosphate, tri-2-ethylhexyl phosphate, tris(butoxyethoxyethyl) phosphate,
triphenyl phosphate, 2-ethylhexyldiphenyl phosphate, etc.), adipate ester plasticizers (di-2-ethylhexyl adipate, bis(butoxyethoxyethyl) adipate, diisodecyl adipate, etc.), sepatate ester plasticizers ( dibutyl sebacate, di-2-ethylhexyl sebacate, etc.), azelaic acid ester plasticizer (di-2-ethylhexyl
azelate, etc.), trimellitic acid ester plasticizers (tributyl trimellitate, tri-2-ethylhexyl trimellitate, etc.), polyester plasticizers (polypropylene adipate, polypropylene sebacate, etc.), epoxy-based plasticizers (epoxidized soybean oil) , epoxidized linseed oil, etc.), chlorinated paraffins, chlorinated fatty acid esters, etc.
本発明の塩素含有樹脂には、通常配合される他の添加剤
、例えば、Ｃａ、 Ｂａ、 Ｍｇ、 ＺｎＸＣｄ、 Ｓ
ｎ、 Ｐｂのカルボン酸塩、フェルレート、有機ホスフ
ェート塩等の有機酸塩、上記金属の酸化物、水酸化物、
炭酸塩、ケイ酸塩、リン酸塩、亜リン酸塩、アルミン酸
塩あるいはこれらの複塩等の無機金属化合物、有機錫化
合物等の汎用の熱安定剤、エポキシ化大豆油、エボキソ
樹脂等のエポキシ化合物、有機ホスファイト化合物、紫
外線吸収剤、光安定剤、顔料、染料、充填剤、発泡剤、
滑剤、難燃剤、βジケトン化合物、フェノール化合物等
を配合することができる。The chlorine-containing resin of the present invention may contain other additives that are normally blended, such as Ca, Ba, Mg, ZnXCd, S
n, Pb carboxylates, ferulates, organic acid salts such as organic phosphate salts, oxides and hydroxides of the above metals,
Inorganic metal compounds such as carbonates, silicates, phosphates, phosphites, aluminates, or their double salts, general-purpose heat stabilizers such as organic tin compounds, epoxidized soybean oil, epoxo resin, etc. Epoxy compounds, organic phosphite compounds, ultraviolet absorbers, light stabilizers, pigments, dyes, fillers, blowing agents,
A lubricant, a flame retardant, a β-diketone compound, a phenol compound, etc. can be blended.
以下、実施例によって本発明を更に詳細に説明するが、
本発明は下記の実施例によって制限を受けるものではな
い。Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited by the following examples.
合成例
ジメチル・ｎ−オクチル・−β−ヒドロキシエチルアン
モニウムバークロレート、６０．３ｇ（０，２モル）に
無水酢酸２２．４ｇ （０，２１モル）を加え、攪拌し
ながら、１１０〜１２０°Ｃにて、２時間反応後、減圧
（１０ｍｍＨｇ）にて脱酢酸を行ない、理論量のジメチ
ル・ｎ−オクチル・−β−アセトキシエチルアンモニウ
ムバークロレートを得た。Synthesis Example 22.4 g (0.21 mol) of acetic anhydride was added to 60.3 g (0.2 mol) of dimethyl n-octyl -β-hydroxyethylammonium verchlorate, and heated at 110 to 120°C while stirring. After reaction for 2 hours, acetic acid was removed under reduced pressure (10 mmHg) to obtain a theoretical amount of dimethyl/n-octyl/-β-acetoxyethylammonium verchlorate.
上記記載の方法に準じ、次の表−１に示す化合物を合成
した。According to the method described above, the compounds shown in Table 1 below were synthesized.
表−１
実施例１
下記の配合物を、１８０℃で５分間ロール混練し、次い
で１６０°Ｃ１２００Ｋｇ／ｃｍ！の条件で５分間プレ
ス加工して厚さ１■のシートを作成した。Table 1 Example 1 The following formulation was roll-kneaded at 180°C for 5 minutes, then 160°C at 1200Kg/cm! A sheet with a thickness of 1 inch was prepared by pressing for 5 minutes under the following conditions.
〔配合〕 重量部塩化ビニ
ル樹脂 １００フタル酸ジー２−エ
チルヘキシル ２０ＭＡＲＫ ＡＣ−２１６２，
８
（アデカ・アーガス化学製Ｂａ／Ｚｎ系液状安定剤）Ａ
ＤＫ ＣＴＺＥＲ０−１３０Ｐ ２．０（アデ
カ・アーガス化学製エポキシ化大豆油）帯電防止剤（表
−１） １．０／２．０このシートを用い
、３０℃、関係湿度６０％の条件で体積固有抵抗（０ｃ
ｍ）および表面固有抵抗（Ω）を測定した。[Formulation] Parts by weight Vinyl chloride resin 100 Di-2-ethylhexyl phthalate 20 MARK AC-2162,
8 (Ba/Zn liquid stabilizer manufactured by Adeka Argus Chemical) A
DK CTZER0-130P 2.0 (Epoxidized soybean oil manufactured by Adeka Argus Chemical) Antistatic agent (Table-1) 1.0/2.0 Using this sheet, the volume specificity was measured at 30°C and relative humidity of 60%. Resistance (0c
m) and surface resistivity (Ω) were measured.
また、このシートを用い、透明性及び１７５°Ｃのギヤ
ーオープン中で熱安定性（分）を測定した。Further, using this sheet, transparency and thermal stability (minutes) in gear open at 175°C were measured.
透明性は１０点法により測定した。Transparency was measured using a 10-point method.
良好 １ １０ 悪
ブリード性はシートを室温及び７０°Ｃ（相対湿度１０
０％）にて、おのおの６ケ月および１ケ月放置後、その
表面状態を観察評価した。Good 1 10 Bad bleed resistance is measured at room temperature and 70°C (relative humidity 10
0%) for 6 months and 1 month, respectively, and then the surface condition was observed and evaluated.
◎二表面光沢有り ○：やや光沢有り △：曇り ×：ブツブツ発生 尚、比較例として、次の化合物を使用した。◎Dual surface gloss ○: Slightly glossy △：Cloudy ×: Bumps occur Incidentally, the following compound was used as a comparative example.
比較化合物Ｉ ステアラミドプロピルジメチル−β−ヒ
ドロキシエチルアンモニウ
ムバークロレート
比較化合物■ ソルビタン・モノパルミテートその結果
を表−２に示す。Comparative Compound I Stearamidopropyl dimethyl-β-hydroxyethylammonium verchlorate Comparative Compound ■ Sorbitan monopalmitate The results are shown in Table 2.
実施例２
可塑剤の量による影響をみるために、下記の配合物によ
り実施例１と同様の操作によりシートを作成し、試験を
行った。Example 2 In order to examine the effect of the amount of plasticizer, a sheet was prepared using the following formulation in the same manner as in Example 1, and tested.
その結果を表−３に示す。The results are shown in Table-3.
〔配合〕 重量部塩化ビニ
ル樹脂 １００フタル酸ジー２−エ
チルヘキシル ３０ＭＡＲＫ ＡＣ−２１６２，
８
（アデカ・アーガス化学製Ｂａ／Ｚｎ系液状安定荊）Ａ
ＤＫ ＣＩＺＥＲ０−１３０Ｆ ２．０（アデ
カ・アーガス化学製エポキシ化大豆油）帯電防止剤（表
−１） １．０／２．０実施例３
軟質配合における効果をみるために、下記の配合物を、
１７０°Ｃで５分間ロール混練し、次いで１６０°Ｃ１
２００Ｋｇ／ｃｍ２の条件で５分間プレス加工して厚さ
１圓のシートを作成した。[Formulation] Parts by weight Vinyl chloride resin 100 Di-2-ethylhexyl phthalate 30 MARK AC-2162,
8 (Ba/Zn-based liquid stabilizer made by Adeka Argus Chemical) A
DK CIZER0-130F 2.0 (Epoxidized soybean oil manufactured by Adeka Argus Chemical) Antistatic agent (Table-1) 1.0/2.0 Example 3 In order to see the effect in soft formulation, the following formulation was used. ,
Roll kneading at 170°C for 5 minutes, then 160°C1
A sheet having a thickness of 1 round was produced by pressing for 5 minutes at 200 kg/cm2.
その結果を表−４に示す。The results are shown in Table-4.
〔配合〕 重量部塩化ビニ
ル樹脂 １００フタル酸ジー２−エ
チルヘキシル ５０ＭＡＲＫ ＡＣ−１６９２，
５
（アデカ・アーガス化学製Ｂａ／Ｚｎ系液状安定剤）Ａ
ＤＫ ＣＩＺＥＲ０−１３０Ｐ ３．０（アデ
カ・アーガス化学製エポキシ化大豆油）帯電防止剤（表
−１） １．０／２．０実施例４
可塑剤の種類による影響をみるために、下記の配合物を
、１７０°Ｃで５分間ロール混練し、次いで１６０℃、
２００ Ｋｇ／ｃｓ！の条件で５分間プレス加工して厚
さ１閣のシートを作成した。[Formulation] Part by weight Vinyl chloride resin 100 Di-2-ethylhexyl phthalate 50 MARK AC-1692,
5 (Ba/Zn liquid stabilizer manufactured by Adeka Argus Chemical) A
DK CIZER0-130P 3.0 (Epoxidized soybean oil manufactured by Adeka Argus Chemical) Antistatic agent (Table 1) 1.0/2.0 Example 4 In order to see the influence of the type of plasticizer, the following formulation was used. The material was roll kneaded at 170°C for 5 minutes, then at 160°C,
200 kg/cs! A sheet with a thickness of 1 inch was created by pressing for 5 minutes under the following conditions.
その結果を表−５に示す。The results are shown in Table-5.
〔配合〕 重量部塩化ビニ
ル樹脂 １００ＭＡＲＫ ＡＣ−
１６９２，５
（アデカ・アーガス化学製Ｂａ／Ｚｎ系液状安定剤）Ａ
ＤＫ ＣＩＺＥＲ０−１３０Ｐ ３．０（アデ
カ・アーガス化学製エポキシ化大豆油）化合物 ■１
可塑剤（表−４） ５０上記の各
実施例の結果から、本発明のアシル化された過塩素酸の
第四級アンモニウム塩化合物を配合することにより、帯
電防止能（体積固有抵抗及び表面固有抵抗）が著しく改
善され、また、帯電防止剤の添加による熱安定性の低下
もなく、しかもブリード性の少ないことが理解される。[Formulation] Part by weight Vinyl chloride resin 100MARK AC-
1692,5 (Ba/Zn liquid stabilizer manufactured by Adeka Argus Chemical) A
DK CIZER0-130P 3.0 (Epoxidized soybean oil manufactured by Adeka Argus Chemical) Compound ■1 Plasticizer (Table 4) 50 From the results of each of the above examples, the By incorporating a quaternary ammonium salt compound, the antistatic ability (volume resistivity and surface resistivity) is significantly improved, and there is no decrease in thermal stability due to the addition of an antistatic agent, and there is little bleeding. is understood.
〔発明の効果］ 本発明の塩素含有樹脂組成物は、 ブリード性や 熱安定性の低下をさせることなく、 帯電防止性を 著しく改善したものである。〔Effect of the invention] The chlorine-containing resin composition of the present invention is Bleedability and without reducing thermal stability. Antistatic properties This is a marked improvement.
Claims (1)
で表されるアシル化された過塩素酸の第四級アンモニウ
ム塩化合物０．０１〜５重量部を添加してなる、帯電防
止性に優れた塩素含有樹脂組成物。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＿１は炭素原子数４〜２２のアルキル基、炭
素原子数７〜２０のアラルキル基または基Ｒ’ＣＯＮＨ
Ｒ”を示し、Ｒ’は炭素原子数１〜２０のアルキル基ま
たはアルケニル基を示し、Ｒ”は炭素原子数１〜１０の
アルキレン基を示し、Ｒ＿２及びＲ＿３は各々独立に炭
素原子数１〜２０のアルキルキ基または▲数式、化学式
、表等があります▼を示し、Ａは炭素数２〜〜４のアル
キレン基を示し、Ｘは水素原子、アルキル基、アリール
基または▲数式、化学式、表等があります▼を示し、ｎ
は１〜２０の整数を示し、Ｒ＿４は炭素原子数１〜２０
のアルキル基を示す。）[Claims] For 100 parts by weight of chlorine-containing resin, the following general formula (I)
A chlorine-containing resin composition with excellent antistatic properties, which contains 0.01 to 5 parts by weight of an acylated quaternary ammonium salt compound of perchloric acid represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 is an alkyl group having 4 to 22 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a group R'CONH
R'' represents an alkyl group or alkenyl group having 1 to 20 carbon atoms, R'' represents an alkylene group having 1 to 10 carbon atoms, and R_2 and R_3 each independently represent an alkyl group or alkenyl group having 1 to 20 carbon atoms. 20 alkyl groups or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, A represents an alkylene group having 2 to 4 carbon atoms, and X is a hydrogen atom, an alkyl group, an aryl group, or ▲numerical formulas, chemical formulas, tables, etc. There is ▼, n
represents an integer of 1 to 20, R_4 is a carbon atom number of 1 to 20
represents an alkyl group. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2134714A JP2981757B2 (en) | 1990-05-24 | 1990-05-24 | Chlorine-containing resin composition with excellent antistatic properties |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2134714A JP2981757B2 (en) | 1990-05-24 | 1990-05-24 | Chlorine-containing resin composition with excellent antistatic properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0428745A true JPH0428745A (en) | 1992-01-31 |
| JP2981757B2 JP2981757B2 (en) | 1999-11-22 |
Family
ID=15134881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2134714A Expired - Fee Related JP2981757B2 (en) | 1990-05-24 | 1990-05-24 | Chlorine-containing resin composition with excellent antistatic properties |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2981757B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5538937A (en) * | 1992-11-13 | 1996-07-23 | Hasebe; Keiko | Agricultural chemical composition comprising quaternary ammonium enhancers |
| JP2005130689A (en) * | 2003-08-02 | 2005-05-19 | Yukio Kinoshita | Rotating electric machine |
-
1990
- 1990-05-24 JP JP2134714A patent/JP2981757B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5538937A (en) * | 1992-11-13 | 1996-07-23 | Hasebe; Keiko | Agricultural chemical composition comprising quaternary ammonium enhancers |
| US5728649A (en) * | 1992-11-13 | 1998-03-17 | Kao Corporation | Agricultural chemical composition |
| US5985794A (en) * | 1992-11-13 | 1999-11-16 | Kao Corporation | Agricultural chemical composition |
| JP2005130689A (en) * | 2003-08-02 | 2005-05-19 | Yukio Kinoshita | Rotating electric machine |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2981757B2 (en) | 1999-11-22 |
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