ZA200200382B - Antistatic Agent. - Google Patents
Antistatic Agent. Download PDFInfo
- Publication number
- ZA200200382B ZA200200382B ZA200200382A ZA200200382A ZA200200382B ZA 200200382 B ZA200200382 B ZA 200200382B ZA 200200382 A ZA200200382 A ZA 200200382A ZA 200200382 A ZA200200382 A ZA 200200382A ZA 200200382 B ZA200200382 B ZA 200200382B
- Authority
- ZA
- South Africa
- Prior art keywords
- plastics
- acid
- salt
- dust
- bis
- Prior art date
Links
- 239000002216 antistatic agent Substances 0.000 title claims description 22
- 229920003023 plastic Polymers 0.000 claims description 40
- 239000004033 plastic Substances 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000465 moulding Methods 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 24
- 239000000428 dust Substances 0.000 description 23
- 229920000515 polycarbonate Polymers 0.000 description 18
- 239000004417 polycarbonate Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 11
- -1 acids salts Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 5
- 150000003460 sulfonic acids Chemical class 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- 239000004416 thermosoftening plastic Substances 0.000 description 5
- RTNVDKBRTXEWQE-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O RTNVDKBRTXEWQE-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 3
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 239000004425 Makrolon Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229920006352 transparent thermoplastic Polymers 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 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
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical class OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- YOLRCEIAJYYYOL-UHFFFAOYSA-M C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCCCCCCC)C1=C(C=CC=C1)S(=O)(=O)[O-] Chemical compound C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCCCCCCC)C1=C(C=CC=C1)S(=O)(=O)[O-] YOLRCEIAJYYYOL-UHFFFAOYSA-M 0.000 description 1
- 239000004608 Heat Stabiliser Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 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
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002817 coal dust Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 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
- 239000004088 foaming agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000007731 hot pressing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920002397 thermoplastic olefin Polymers 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical class C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Injection Moulding Of Plastics Or The Like (AREA)
Description
Antistatic agent
This application relates to the use of fluorinated alkylsulfonic acids salts as an antistatic agent in particular in plastics and to plastics containing fluorinated alkylsulfonic acid salts and to mouldings producible therefrom.
The deposition of dust to form dust figures is a widespread problem with plastics mouldings, c.f in this connection for example Saechtling Kunststoff-Taschenbuch, 26" edition, Hanser Verlag, 1995, Munich, pp. 140 et seq.. Dust deposits on transparent mouldings are particularly troublesome and restrict function. Such mouldings are used, for example, for applications in optical data storage media, electrical engineering, automotive engineering, in the building sector, for liquids containers or for other optical applications. Dust deposition is undesirable for all these applications and may impair function.
One known method for reducing the deposition of dust on plastics articles is to use antistatic agents. The literature contains descriptions of antistatic agents for thermoplastics which restrict dust deposition (c.f for example Géchter, Miiller,
Plastic Additives, Hanser Verlag, Munich, 1996, pp. 749 et seq.). These antistatic agents improve the electrical conductivity of the plastics moulding compositions and thus dissipate any surface charges which develop during production and use. Dust particles are thus less attracted and dust deposition is consequently reduced.
A distinction is generally drawn between internal and external antistatic agents. An external antistatic agent is applied onto the plastics moulding after processing, while an internal antistatic agent is added as an additive to the plastics moulding compositions. On economic grounds, it is usually desirable to use internal antistatic agents, as no further operations for applying the antistatic agent are required after processing. Few internal antistatic agents have hitherto been described in the literature which also form completely transparent mouldings, especially with polycarbonate. JP-06228420 A 940816 describes aliphatic sulfonic acid ammonium salts as an antistatic agent in polycarbonate. However, these compounds bring about a reduction in molecular weight. JP-62230835 describes the addition of 4% of nonylphenylsulfonic acid tetrabutylphosphonium to polycarbonate.
One disadvantage of known antistatic agents is that they must be used in relatively high-coneentrations in order to achieve the-antistatic-effect. However, such addition — modifies the material properties of the plastics in an unwanted manner.
The object of the invention is accordingly to provide antistatic agents which have no negative impact on the material properties of plastics.
It has surprisingly been found that perfluoroalkylsulfonic acid salts are particularly suitable as antistatic agents for the production of injection moulded and extruded mouldings. Even small quantities of perfluoroalkylsulfonic acid salt give rise to mouldings which no longer attract dust.
This application accordingly provides the use of perfluoroalkylsulfonic acid salts as antistatic agents, in particular for plastics, in particular for transparent plastics, as well as plastics, plastics moulding compositions and plastics mouldings containing at least one perfluoroalkylsulfonic acid salt.
Preferably suitable perfluoroalkylsulfonic acid salts are salts of the type (I)
RA-SO,; X @ in which
R means perfluorinated linear or branched carbon chains having 1 to 30 carbon atoms, preferably 4 to 8 carbon atoms;
A means a direct bond or an aromatic nucleus, for example and preferably fluorinated or non-fluorinated o-, m- or p-phenylene;
X means an alkylated and/or arylated ammonium ion NR'R"R"™R"", phosphonium ion PRR"R"R"", sulfonium ion SR'R"R", and a substituted or unsubstituted imidazolinium ion, pyridinium ion-or tropylium ion, in which
R', R", R™, R"" mutually independently denote halogenated or non- halogenated, linear or branched carbon chains having 1 to 30 carbon atoms, preferably 1 to 4 carbon atoms, in particular methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, tert.-butyl, neopentyl or aromatic residues or alkylaromatic residues such as for example and preferably phenyl, benzyl, alkylphenyl in each case having 1 to 4 carbon atoms in the alkyl portion.
The following are preferred: - perfluorooctanesulfonic acid tetraethylammonium salt, - perfluorobutanesulfonic acid tetraecthylammonium salt, - perfluorooctanesulfonic acid tetrabutylphosphonium salt, - perfluorobutanesulfonic acid tetrabutylphosphonium salt, - perfluorooctanesulfonic acid benzyltrimethylammonium salt, - perfluorobutanesulfonic acid benzyltrimethylammonium salt, - perfluorooctanesulfonic acid trimethylphenylammonium salt, - perfluorobutanesulfonic acid trimethylphenylammonium salt, - perfluorobutanesulfonic acid dimethyldiphenylammonium salt, - perfluorooctanesulfonic acid dimethyldiphenylammonium salt, - perfluorobutanesulfonic acid trimethylneopentylammonium salt, - perfluorooctanesulfonic acid trimethylneopentylammonium salt, - perfluorobutanesulfonic acid dimethyldineopentylammonium salt, - perfluorooctanesulfonic acid dimethyldineopentylammonium salt, - perfluorobutanesulfonic acid tetrabutylphosphonium salt, - perfluorooctanesulfonic acid tetrabutylphosphonium salt.
Mixtures of sulfonic acid salts, in particular of the above-stated sulfonic acid salts, are also preferred.
Perfluorooctanesulfonic acid tetraecthylammonium salt is particularly preferred.
Perfluoroalkylsulfonic- acid salts are known or may be produced using known methods. The salts of the sulfonic acids may be produced by combining equimolar quantities of the free sulfonic acid with the hydroxy form of the corresponding cation in water at room temperature and evaporating the solution.
The perfluoroalkylsulfonic acids are preferably added to the plastics in quantities of 0.001 to 2 wt.%, preferably of 0.1 to 1 wt.%.
Plastics are preferably taken to mean thermoplastics, in particular transparent thermoplastics, preferably the polymers of ethylenically unsaturated monomers and/or polycondensation products of difunctional reactive compounds.
Particularly suitable plastics are polycarbonates or copolycarbonates based on diphenols, poly- or copolyacrylates and poly- or copolymethacrylates such as for example and preferably polymethyl methacrylate, poly- or copolymers with styrene such as for example and preferably transparent polystyrene or styrene/acrylonitrile copolymer (SAN), transparent thermoplastic polyurethanes, and polyolefins, such as for example and preferably transparent grades of polypropylene or polyolefins based on cyclic olefins (for example TOPAS®, Hoechst), poly- or copolycondensation products of terephthalic acid, such as for example and preferably poly- or copolyethylene terephthalate (PET or CoPET) or glycol-modified PET (PETG).
Polycarbonates or copolycarbonates are particularly preferred, in particular non-halogenated polycarbonates and/or copolycarbonates having molecular weights
M,, of 500 to 100,000, preferably of 10,000 to 50,000, particularly preferably of 15,000 to 40,000.
For the purposes of the present invention, thermoplastic, aromatic polycarbonates comprise both homopolycarbonates and copolycarbonates; the polycarbonates may be linear or branched in known manner.
The polycarbonates. according to the invention may also be present in entirely or _ partially brominated form.
These polycarbonates are produced in known manner from diphenols, carbonic acid derivatives, optionally chain terminators and optionally branching agents.
Details of the production of polycarbonates have been described in many patents over the last 40 years or so. Reference is made purely by way of example to Schnell, "Chemistry & Physics of Polycarbonates", Polymer Reviews, vol. 9, Interscience
Publishers, New York, London, Sydney 1964, to D. Freitag, U. Grigo, P.R. Miiller,
H. Nouvertne', Bayer AG, "Polycarbonates" in Encyclopedia of Polymer Science &
Engineering, vol. 11, 2™ edition, 1988, pp. 648-718 and finally to Dr. U. Grigo, Dr.
K. Kirchner and Dr. P.R. Miiller, "Polycarbonate" in Becker/Braun, Kunststoff-
Handbuch, vol. 3/1, Polycarbonate, Polyacetale, Polyester, Celluloseester, Carl
Hanser Verlag, Munich/Vienna, 1992, pp. 117-299.
Preferred diphenols for the production of polycarbonates are: 4,4'-dihydroxydiphenyl, 2,2-bis-(4-hydroxyphenyl)propane, 2,4-bis-(4-hydroxy- phenyl)-2-methylbutane, 1,1-bis-(4-hydroxyphenyl)-p-diisopropylbenzene, 2,2-bis- (3-methyl-4-hydroxyphenyl)propane, 2,2-bis-(3-chloro-4-hydroxyphenyl)propane, bis-(3,5-dimethyl-4-hydroxyphenyl)methane, 2,2-bis-(3,5-dimethyl-4- hydroxyphenyl)propane, bis-(3,5-dimethyl-4-hydroxyphenyl) sulfone, 2,4-bis-(3,5- dimethyl-4-hydroxyphenyl)-2-methylbutane, 1,1-bis-(3,5-dimethyl-4- hydroxyphenyl)-p-diisopropylbenzene, 2,2-bis-(3,5-dichloro-4- hydroxyphenyl)propane, 2,2-bis-(3,5-dibromo-4-hydroxyphenyl)propane and 1,1- bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.
Particularly preferred diphenols are 2,2-bis-(4-hydroxyphenyl)propane, 2,2-bis-(3,5- dimethyl-4-hydroxyphenyl)propane, 2,2-bis-(3,5-dichloro-4- hydroxyphenyl)propane, 2,2-bis-(3,5-dibromo-4-hydroxyphenyl)propane, 1,1-bis-(4- hydroxyphenyl)cyclohexane and 1,1-bis-(4-hydroxyphenyl)-3,3,5- trimethylcyclohexane. : _
Preferred branching agents are triphenols, trimesic acid (trichloride), cyanuric acid trichloride and 3,3-bis-(3-methyl-4-hydroxyphenyl)-2-oxo0-2,3-dihydroindole.
Improved plastics compositions may be obtained by incorporating at least one further additive conventionally present in thermoplastics, preferably poly- and copolycarbonates, such as for example stabilisers (as described, for example, in
EP 0839 623 Al or EP 0 500 496 Al), especially heat stabilisers, in particular organic phosphites or phosphines, for example and preferably triphenylphosphine, mould release agents, for example and preferably fatty acid esters of glycerol or tetramethanolmethane, wherein unsaturated fatty acids may be entirely or partially epoxidised, in particular glycerol monostearate or pentaerythritol tetrastearate (PETS), flame retardants, UV absorbents, for example and preferably hydroxybenzo- triazoles and hydroxytriazines, fillers, foaming agents, dyes, pigments, optical brighteners, transesterification catalysts and nucleating agents or the like, preferably in quantities of in each case up to 5 wt.%, preferably of 0.01 to 5 wt.%, relative to the entire mixture, particularly preferably of 0.01 wt.% to 1 wt.%, relative to the quantity of plastics.
The perfluoroalkylsulfonic acid salts and optionally the additives or mixtures of additives are generally incorporated in the conventional manner for example before or during polymerisation or by subsequent mixing with the plastic.
The plastics compositions obtained in this manner are generally in the form of solutions, dispersions, emulsions, finely divided solids, powders, pellets, platelets or flakes (moulding compositions) and are used for the production of shaped articles (mouldings).
Shaped articles are for example and preferably light-transmitting articles such as for example and preferably light diffusers for motor vehicles, lenses, such as for example--spectacle lenses; films; tapes, sheets; multi-wall sheets, multiple wall - sheets, containers, tubes and other profiles which are produced using conventional methods, such as for example hot pressing, spinning, extrusion or injection moulding. The polymer compositions may also be converted mto cast films.
It is also of interest to use the plastics composition according to the invention for the production of multilayer systems. In such cases, the plastics composition according to the invention is applied in a thin layer onto a shaped article of a plastic which does not have an antistatic finish or additive. Application may proceed simultaneously with or immediately after shaping of the moulding, for example by coextrusion or multi-component injection moulding. Application may, however, also be performed onto the pre-shaped substrate, for example by lamination with a film or by coating with a solution.
It is furthermore of interest to use the plastics compositions according to the invention for the production of casings for electrical and electronic appliances, such as for example televisions, monitors, computers, printers, mobile telephones, clocks, hi-fi systems and the like in any desired colours with a transparent, translucent or opaque formulation, optionally with a flame-retardant finish or additive.
Plastics compositions containing perfluoroalkylsulfonic acid ammonium salts are preferably used for the production of light diffusers for motor vehicles.
It is also of particular interest to use plastics compositions containing perfluoroalkyl- sulfonic acid salts for the production of sheet, double-wall sheet, coextruded sheet and film.
The advantage of the plastics mouldings provided with the antistatic agents according to the invention is that these mouldings no longer develop a static charge, for example during production, when the conventionally used protective films are peeled off or during transport and storage.
The following Examples illustrate the invention. The invention is not limited to the
Examples. The percentages stated below are weight percentages.
Dust test
In order to test dust deposition in a laboratory test, the injection moulded sheets are exposed to an atmosphere containing suspended dust. To this end, a 2 litre beaker containing an 80 mm long magnetic stirrer rod of a triangular cross-section is filled to a depth of approx. 1 cm with dust (coal dust/20 g activated carbon, Riedel de -
Haen, Seelze, Germany, item no. 18003). The dust is suspended in the atmosphere with a magnetic stirrer. Once the stirrer has been shut off, the test specimen is exposed to this dusty atmosphere for 7 seconds. Depending upon the test specimen used, a greater or lesser amount of dust is deposited on the test specimens.
Evaluation of dust deposition (dust figures) is performed visually. Sheets exhibiting dust figures were rated (-), while virtually dust-free sheets were rated (+).
Example 1
In order to produce the test specimens, an additive-free, unstabilised polycarbonate (Makrolon® 2808 from Bayer AG, Leverkusen) having an average molecular weight of approx. 30,000 (M,, by GPC), solution viscosity: n = 1.293 at 340°C, is compounded in a twin screw extruder with the quantity of perfluorooctanesulfonic acid tetraecthylammonium salt (Bayowet 248® from Bayer AG, Leverkusen) and the other stated additives shown in Table 1 and then pelletised.
Rectangular sheets (155 mm x 75 mm x 2 mm) are then injection moulded from these pellets at various melt temperatures and subjected to the dust test. The results are stated in Table 2.
Table 1: Plastics compositions 1.1 1% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'-hydroxy- 3'-(2-butyl)-5'-(tert-butyl)phenyl)benzotriazole (Tinuvin® 350, Ciba
Spezialititenchemie, Basel) 1.2 10.6% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'- oe 1.3 0.4% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'- eo 1.4 0.3% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'- eo 1.5 0.25% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'-
Rl sg 1.6 0.2% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'- eee 1.7 0.15% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'-
Ill dg 1.8 0.1% Bayowet 248® + 0.025% triphenylphosphine + 0.3% 2-(2'- er
All the colour sample sheets produced from the plastics compositions of Examples 1.1 to 1.8 at melt temperatures a), b) and c) are completely transparent on visual inspection.
Table 2: Results of dust test
I EE EE
EE
IEC EC EC EC
ILC EC EC EA
CA CR EA A
EL CR CR EA
Example 2:
Polycarbonate films of a thickness of 0.25 mm based on the polycarbonate Makrolon 3100® from Bayer AG, Leverkusen and the antistatic agent contents stated in Table 3 are produced by extrusion at a melt temperature of 280°C. Antistatic action is determined by measuring surface conductivity to DIN IEC 93 (Q).
Table 3: Plastics film composition
CC cc
ICAI LC EC LAC
Surface resistance is reduced by almost 2 orders of magnitude by the addition of 0.3 wt.% of Bayowet® 248 and by more than 4 orders of magnitude by the addition of 1.5 wt.%. This is significantly better than the values hitherto described for antistatic agents in this range of concentrations in polycarbonate.
Example 3:
The compositions stated in Table 4 are produced according to Example 1 and subjected to the dust test. The perfluorobutanesulfonic acid and perfluorooctane- - sulfonic-acid-may be liberated by the-action of concentrated sulfuric-acid on the — potassium salts of the sulfonic acids and isolated by distillation. The potassium salts are obtainable from Aldrich or from Bayer AG, Leverkusen. Trimethylphenyl- ammonium hydroxide may be produced from trimethylphenylammonium chloride (Aldrich) by means of ion exchange on the anion exchanger Lewatit® 500 (Bayer AG). Tetracthylammonium hydroxide and benzyltrimethylammonium hydroxide are obtainable from Aldrich.
Table 4: Plastics compositions
Example Composition Melt Dust test [= 3.1 0.3% perfluorobutanesulfonic acid 320°C + tetraethylammonium salt + 0.025% - | triphenylphosphine + 0.3% 2-(2'-hydroxy-3'- (2-butyl)-5'-(tert-butyl)phenyl)benzotriazole 3.2 0.3% perfluorobutanesulfonic acid 320°C + benzyltrimethylammonium salt + 0.025% triphenylphosphine + 0.3% 2-(2'-hydroxy-3'- (2-butyl)-5'-(tert-butyl)phenyl)benzotriazole 33 0.3% perfluorooctanesulfonic acid 300°C + trimethylphenylammonium salt + 0.025% triphenylphosphine + 0.3% 2-(2'-hydroxy-3'- (2-butyl)-5'-(tert-butyl)phenyl)benzotriazole 34 1% perfluorooctanesulfonic acid 300°C + tetraethylammonium salt + 1% titanium dioxide Cronos C12230 + 0.2% perfluorobutanesulfonic acid potassium salt (Bayer) + 0.09% Teflon 6CN (DuPont) 35 1% perfluorooctanesulfonic acid 300°C + tetraethylammonium salt + 1% titanium dioxide Cronos C12230
Example 4:
In a similar manner to Example 1, plastics compositions are produced from
Bayblend® (blend of ABS and bisphenol A polycarbonate of Bayer AG), Apec® (copolycarbonate of Bayer AG) and Pocan® (unreinforced polybutylene terephthalate of Bayer AG) with the quantities of antistatic agent and at the melt temperatures stated in Table 5 and were subjected to the dust test. The results are given in Table 5.
Table 5: Action of sulfonic acid salts in further thermoplastics
Example Composition Melt
I EA 0 4 4.5 Apec® HT KU1-9201=9330 + 0.5% Bayowet 300°C +
IE a 4.6 Apec® HT KU1-9201=9330 + 0.5% Bayowet 340°C +
Rha a
Claims (7)
1. Use of perfluoroalkylsulfonic acid salts as an antistatic agent.
2. Use of perfluoroalkylsulfonic acid salts to impart antistatic properties to — plastics:
3. Plastics compositions containing at least one perfluoroalkylsulfonic acid salt.
4. Process for the production of plastics compositions as defined in claim 3, characterised in that at least one perfluoroalkylsulfonic acid salt is added before, during or after polymerisation of the plastics.
5. Use of plastics compositions containing perfluoroalkylsulfonic acid salt for the production of mouldings.
6. Process for the production of mouldings having antistatic properties, characterised in that at least one plastics composition as defined in claim 3 is used as the starting material.
7. Plastics mouldings containing at least one perfluoroalkylsulfonic acid salt.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19938735 | 1999-08-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200200382B true ZA200200382B (en) | 2003-03-26 |
Family
ID=7918512
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200200382A ZA200200382B (en) | 1999-08-16 | 2002-01-16 | Antistatic Agent. |
Country Status (7)
Country | Link |
---|---|
JP (1) | JP4803932B2 (en) |
KR (1) | KR20020027545A (en) |
AR (1) | AR025295A1 (en) |
DE (2) | DE19943637A1 (en) |
HK (1) | HK1049677A1 (en) |
IL (1) | IL147680A (en) |
ZA (1) | ZA200200382B (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1290106B1 (en) * | 2000-05-12 | 2009-08-12 | Bayer MaterialScience AG | Antistatic agent |
DE10119416A1 (en) * | 2001-04-20 | 2002-10-24 | Bayer Ag | Layer system comprising at least two layers of thermoplastics, useful for the production of molded articles and extrudate, has at least one layer that contains a sulfonate antistatic compound. |
DE10131764A1 (en) * | 2001-06-30 | 2003-01-09 | Cognis Deutschland Gmbh | Use of fluoroalkanesulfonic acids to stabilize halogen-containing organic plastics |
DE60310739T2 (en) * | 2002-08-27 | 2007-10-11 | Jsr Corp. | ANISOTROPE CONDUCTIVE FILM AND IMPEDANCE MEASURING PROBE |
JP2006137106A (en) * | 2004-11-12 | 2006-06-01 | Nitto Denko Corp | Adhesive sheet for removing solvent containing matter |
US20070203271A1 (en) * | 2006-01-27 | 2007-08-30 | Alms Gregory R | Coating process for thermoplastics |
US8093317B2 (en) | 2006-02-13 | 2012-01-10 | Toray Industries, Inc. | Antistatic thermoplastic resin composition and molded article composed thereof |
WO2007119631A1 (en) * | 2006-03-31 | 2007-10-25 | Koei Chemical Company, Limited | Antistatic agent, and antistatic resin composition comprising the same |
EP2157133A1 (en) * | 2008-08-19 | 2010-02-24 | Bayer MaterialScience AG | Films with improved characteristics |
KR101367404B1 (en) * | 2010-04-28 | 2014-02-25 | 주식회사 엘지화학 | Thermoplastic composition for smart card |
JP6766709B2 (en) * | 2017-03-15 | 2020-10-14 | 三菱エンジニアリングプラスチックス株式会社 | Polycarbonate resin composition and its molded product |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4112206A (en) * | 1977-07-05 | 1978-09-05 | Continental Oil Company | Polyvinyl chloride having improved antistatic properties |
US4570197A (en) * | 1983-01-03 | 1986-02-11 | Minnesota Mining & Manufacturing Company | Static reduction in magnetic recording cassettes |
US4505990A (en) * | 1983-07-14 | 1985-03-19 | Hercules Incorporated | Coating compositions |
JPS61285232A (en) * | 1985-06-13 | 1986-12-16 | Daikin Ind Ltd | Antistatic agent composition |
JP2767772B2 (en) * | 1987-09-30 | 1998-06-18 | 竹本油脂株式会社 | Antistatic agent for synthetic polymer materials |
US4806571A (en) * | 1988-05-06 | 1989-02-21 | The Dow Chemical Company | Organic composition containing a fluoroalkyl sulfonic acid salt |
DE4015184A1 (en) * | 1990-05-11 | 1991-11-14 | Hoechst Ag | ANTISTATICALLY EQUIPPED PLASTIC MOLDING |
US5176943A (en) * | 1991-07-09 | 1993-01-05 | Minnesota Mining And Manufacturing Company | Optical recording medium with antistatic hard coating |
JPH10265673A (en) * | 1997-03-25 | 1998-10-06 | Mitsubishi Chem Corp | Polymer compound composite material and its production |
US6194497B1 (en) * | 1997-07-23 | 2001-02-27 | General Electric Company | Anti-static resin composition containing fluorinated phosphonium sulfonates |
-
1999
- 1999-09-13 DE DE19943637A patent/DE19943637A1/en not_active Withdrawn
-
2000
- 2000-08-03 JP JP2001517603A patent/JP4803932B2/en not_active Expired - Lifetime
- 2000-08-03 DE DE50006899T patent/DE50006899D1/en not_active Expired - Lifetime
- 2000-08-03 KR KR1020027001962A patent/KR20020027545A/en active Search and Examination
- 2000-08-16 AR ARP000104237A patent/AR025295A1/en not_active Application Discontinuation
-
2002
- 2002-01-16 ZA ZA200200382A patent/ZA200200382B/en unknown
- 2002-01-17 IL IL147680A patent/IL147680A/en not_active IP Right Cessation
-
2003
- 2003-03-07 HK HK03101683.7A patent/HK1049677A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
HK1049677A1 (en) | 2003-05-23 |
JP4803932B2 (en) | 2011-10-26 |
KR20020027545A (en) | 2002-04-13 |
JP2003507510A (en) | 2003-02-25 |
IL147680A (en) | 2010-12-30 |
DE19943637A1 (en) | 2001-02-22 |
DE50006899D1 (en) | 2004-07-29 |
AR025295A1 (en) | 2002-11-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU760642B2 (en) | Antistatic agent | |
US5674928A (en) | Thermoplastic resin compositions containing a high hydroxyl polyester and a polycarbonate, and articles made therefrom | |
JP2002537464A (en) | Flame resistant thermoplastic molding composition | |
CA2407968C (en) | Antistatic agent | |
ZA200200382B (en) | Antistatic Agent. | |
KR20150065774A (en) | Enhanced polycarbonate extrusion grades | |
JP2004523643A (en) | Flame retardant polycarbonate-containing composition having antistatic properties | |
US9290590B2 (en) | Polymeric anti-static agent | |
AU5069200A (en) | Polycarbonate molding compounds for producing articles with reduced dust attraction | |
JP2008127557A (en) | Polycarbonate resin composition containing red dyestuff, and molded article made from the resin composition | |
JP2003507510A5 (en) | ||
JP2018141076A (en) | Polycarbonate resin composition and molding | |
US20110230595A1 (en) | Process for the production of impact-modified polyalkylene terephthalate/polycarbonate compositions | |
JP2009511667A (en) | Irradiation stable aromatic carbonate polymer composition | |
JP2021532222A (en) | Mineral-filled polycarbonate-polyalkylene terephthalate composition, molding compound and moldings with good impact toughness | |
US6737457B2 (en) | Use of zwitterionic compounds as mold release agents in thermoplastics | |
JP2003096291A (en) | Antistatic polycarbonate resin composition | |
JP2002020609A (en) | Antistatic polycarbonate resin composition | |
JP2003012915A (en) | Antistatic polycarbonate resin composition | |
JP2002020608A (en) | Antistatic polycarbonate resin composition | |
JP2002144393A (en) | Method for molding antistatic polycarbonate resin and molded article thereof |