EP3183324A1 - Hydraulic fluids in plastic injection molding processes - Google Patents
Hydraulic fluids in plastic injection molding processesInfo
- Publication number
- EP3183324A1 EP3183324A1 EP15750369.9A EP15750369A EP3183324A1 EP 3183324 A1 EP3183324 A1 EP 3183324A1 EP 15750369 A EP15750369 A EP 15750369A EP 3183324 A1 EP3183324 A1 EP 3183324A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- meth
- group
- viscosity index
- acrylate
- carbon atoms
- 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
- 239000012530 fluid Substances 0.000 title claims abstract description 57
- 238000001746 injection moulding Methods 0.000 title claims abstract description 34
- 239000004033 plastic Substances 0.000 title claims abstract description 23
- 229920003023 plastic Polymers 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 43
- 230000008569 process Effects 0.000 claims abstract description 12
- 238000005265 energy consumption Methods 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 53
- 239000000178 monomer Substances 0.000 claims description 37
- -1 ester compounds Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000003921 oil Substances 0.000 claims description 20
- 239000002199 base oil Substances 0.000 claims description 19
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 11
- 239000002270 dispersing agent Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- JNDVNJWCRZQGFQ-UHFFFAOYSA-N 2-methyl-N,N-bis(methylamino)hex-2-enamide Chemical compound CCCC=C(C)C(=O)N(NC)NC JNDVNJWCRZQGFQ-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000000465 moulding Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 229920013639 polyalphaolefin Polymers 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000000011 acetone peroxide Substances 0.000 description 1
- 235000019401 acetone peroxide Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 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 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 229940069096 dodecene Drugs 0.000 description 1
- 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 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 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 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001196 nonadecyl 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])[H] 0.000 description 1
- 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 1
- 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 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 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 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
- C10M145/14—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/18—Anti-foaming property
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/54—Fuel economy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the present invention relates to the use of hydraulic fluids in plastic injection molding processes.
- PIM plastic injection molding processes
- Injection molding is a manufacturing process for producing parts by injecting material into a mould at well controlled temperatures, pressures and cycle times. Injection moulding can be performed with a host of materials, including metals, glasses, elastomers, confections, and most commonly thermoplastic and thermosetting polymers. Material for the part is fed into a heated barrel, mixed, and forced into a mold cavity, where it cools and hardens to the configuration of the cavity.
- Injection moulding machine is actuated by hydraulic system, wherein the electrical energy is transformed into mechanical energy through hydraulic energy. The energy reaches the actuators in the form of pressure and volume flow. While transmitting power through hydraulic forces, a loss of energy is observed due to flow losses and friction. In addition, the compression of hydraulic fluid develops frictional heat, which has to be controlled for example by cooling. Pump type and control of that pump also contribute heavily to how efficient a molding machine is in processing the plastic.
- EP 2337832 discloses a method of reducing noise generation in a hydraulic system, comprising contacting a hydraulic fluid comprising a polyalkyl(meth)acrylate polymer with the hydraulic system.
- the hydraulic fluid has a Viscosity Index VI of at least 130.
- the polyalkyl(meth)acrylate has a molecular weight in the range of 10 000 to 200 000 g/mol and is obtained by polymerizing a mixture of olefinically unsaturated monomers, said mixture comprising preferably 50 to 95 wt% C9 to C16 and 1 to 30 wt% of
- Target of the invention described in EP 2337832 was the reduction of noise which is achieved by increasing oil viscosities at higher temperatures.
- high viscosities and high densities are beneficial and the high VI of the fluids is used to increase the viscosity at the operating temperature.
- a completely different approach is used to increase the energy efficiency.
- a high VI is used to enable a reduction of the base fluid viscosity. This reduced viscosity in combination with a low density of the hydraulic base fluid increases the efficiency of the injection molding process.
- hydraulic fluids according to the present invention decrease the noise level.
- EP 2157159 discloses a hydraulic fluid containing, as a base oil, an ester containing at least two ring structures. It is described that the hydraulic fluid has low energy loss due to compression and exhibits excellent responsiveness when being used in a hydraulic circuit. Consequently, the hydraulic fluid realizes energy-saving, high-speed operation and high precision of control in the hydraulic circuit.
- EP 19871 18 discloses the use of a fluid with a viscosity improving index of at least 130 for the use in hydraulic systems like engines or electric motors.
- This fluid comprises a copolymer of Ci to C6 (meth)acrylates, C7 to C40 (meth)acrylates and optionally further with (meth)acrylates copolymerizable monomers in a mixture of an API group II or III mineral oil and a polyalphaolefine with a molecular weight below 10,000 g/mol. It is neither shown here that such a fluid is also usable in an injection molding machine nor which specific composition of the fluid would be applicable in such a machine.
- the improvement of energy efficiency is a common object in the technical field of injection molding. Usually such objects are achieved by construction improvements of the unit providing mechanical energy of the hydraulic system. However, there is still a need for further improvements with regard to that object. Accordingly, the purpose of the present invention was to provide a method for saving energy, increase productivity, avoid heating, improve air release and avoid cavitation over a broad temperature operating window in a hydraulic system used in plastic injection molding processes.
- the object of the present invention to improve the performance of a hydraulic system in a plastic injection molding machine with energy savings of at least 5% and of up to 10%, compared to the performance of a machine when run with a standard fluid having a VI around 100 as recommended by the producers of injection molding machines. It was also object to realize an energy saving for single, very energy consuming process steps of more than 10%.
- a hydraulic fluid is used in a plastic injection molding process.
- the hydraulic fluid composition thereby comprises (i) a polyalkyl(meth)acrylate viscosity index improver and (ii) a base oil.
- the polyalkyl(meth)acrylate viscosity index improver (i) thereby comprises at least monomer units a) and b) and optionally monomer units c) and/or d).
- the component (i) has a weight average molecular weight (Mw) from 20,000 to 100,000 g/mol. More preferred the molecular weight M w is between 30,000 and 85,000 g/mol and especially preferred between 40,000 and 70,000 g/mol.
- the polydispersity index of the polyalkyl(meth)acrylate viscosity index improver is between 1 and 4, preferred between 1.2 and 3.0 and most preferred between 1 .5 and 2.5.
- the polyalkyl(meth)acrylate viscosity index improver (i) contains 5 to 40 wt.%, preferred 7 to 30 wt.%, more especially preferred 10 to 25 wt.% of repeating units that have been obtained by the copolymerization of monomers a) and 50 to 95 wt.%, preferred 60 to 93 wt.%, more especially preferred 70 to 90 wt.% of repeating units that have been obtained by the copolymerization of monomers b).
- the amount of the compound of formula (II) is between 75 and 90 wt.%, especially preferred between 70 and 80 wt.%.
- Monomers a) thereby are one or more eth lenically unsaturated ester compounds of formula (I)
- R is equal to H or Ch
- R represents a linear or branched alkyl group with 1 to 6 carbon atoms
- R 2 and R 3 independently represent H or a group of the formula -COOR', wherein R' is H or an alkyl group with 1 to 5 carbon atoms.
- component a) examples are, among others, (meth)acrylates, fumarates and maleates, which derived from saturated alcohols such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate and/or pentyl (meth)acrylate; cycloalkyl (meth)acrylates, like cyclopentyl (meth)acrylate. Methacrylates are even preferred over acrylates.
- Monomers b) are one or more ethylenically unsaturated ester compounds of formula (II)
- R is equal to H or Ch
- R 4 represents a linear or branched alkyl group with 7 to 15 carbon atoms
- R 5 and R 6 independently represent H or a group of the formula -COOR", wherein R" is H or an alkyl group with 6 to 15 carbon atoms.
- (meth)acrylates, fumarates and maleates that derive from saturated alco-hols such as n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, 2-tert-butylheptyl (meth)acrylate, octyl (meth)acrylate, 3-isopropylheptyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, 5-methylundecyl (meth)acrylate, dodecyl (meth)acrylate, 2- methyldodecyl (meth)acrylate, tridecyl (meth)acrylate, 5-methyltridecyl (meth)acrylate, tetradecyl (meth)acrylate and/or pentadecyl (meth)acrylate.
- saturated alco-hols
- the polyalkyl(meth)acrylate viscosity index improver (i) may also contain further components that are in form of a monomer copolymerizable with at least one of the components a) and b). These further monomers are especially the components c) and d), with c) in a maximal concentration of 30 wt.% and d) in a maximal concentration of 10 wt.%. Monomers c) thereby repre
- R is equal to H or Ch
- R 7 represents a linear or branched alkyl group with 16 to 30 carbon atoms
- R 8 and R 9 independently represent H or a group of the formula -COOR'", wherein R'" is H or an alkyl group with 16 to 30 carbon atoms.
- component c) are, among others, (meth)acrylates, fumarates and maleates, which derived from saturated alcohols such as 2-methylhexadecyl (meth)acrylate, heptadecyl (meth)acrylate, 5- isopropylheptadecyl (meth)acrylate, 4-tert-butyloctadecyl (meth)acrylate, 5-ethyloctadecyl (meth)acrylate, 3-isopropyloctadecyl (meth)acrylate, octadecyl (meth)acrylate, nonadecyl (meth)acrylate, eicosyl (meth)acrylate, cetyleicosyl (meth)acrylate, stearyleicosyl (meth)acrylate and/or docosyl (meth)acrylate.
- saturated alcohols such as 2-methylhexadecyl (meth)acrylate, heptadecyl (meth)
- the polyalkyl(meth)acrylate viscosity index improver (i) contains 5 to 20 wt.% of the monomers a), 70 to 90 wt.% of the monomers b) and 2 to 25 wt.% of the monomers c) in polymerized form.
- Monomers d are at least one N-dispersant monomer. Preferred this N-dispersant monomer is of the
- R 4 represents a linear or branched alkyl group with 1 to 20 carbon atoms which is substituted by a group NR 6 R 17 , where R 6 and R 7 independently represent H or a linear or branched alkyl group with 1 to 8 carbon atoms, or wherein R 6 and R 7 are part of a 4 to 8 membered saturated or unsaturated ring containing optionally one or more hetero atoms chosen from the group consisting of nitrogen, oxygen or sulfur, wherein said ring may be further substituted with alkyl or aryl groups.
- R 3 is a group NR 8 R 19 , wherein R 8 and R 9 are part of a 4 to 8 membered saturated or unsaturated ring, containing at least one carbon atom as part of the ring which forms a double bond to a hetero atom chosen from the group consisting of nitrogen, oxygen or sulfur, wherein said ring may be further substituted with alkyl or aryl groups.
- said dispersant monomer d) of polymer (i) is at least one monomer selected from the group consisting of N-vinylic monomers, (meth)acrylic esters, (meth)acrylic amides, (meth)acrylic imides each with N-containing, dispersing moieties in the side chain.
- the N-dispersant monomer is at least one monomer selected from the group consisting of N-vinyl pyrrolidone, N,N- dimethylaminoethyl methacrylate and N,N-dimethylaminopropylmethacrylamide.
- the polyalkyl(meth)acrylate viscosity index improver (i) contains 5 to 25 wt.% of the monomers c) and 1 to 7 wt.% of the monomers d), both in polymerized form.
- the viscosity index improver (i) contains 10 to 20 wt.% of the monomers c) and 2 to 5 wt.% of at least one N- dispersant monomer d) in polymerized form.
- the base oil (ii) is selected from API group I, II, III or IV base oils or a mixture thereof.
- the formulated hydraulic fluid of this invention has a fresh oil viscosity index of at least 160, a viscosity at 40°C of 15 cSt to 51 cSt and a density at 15°C of 800 kg/m 3 to 890 kg/m 3 .
- API group IV base oils in form of polyalphaolefin (PAO) or mixtures of API group I to IV base oils containing at least 50 wt.% polyalphaolefins.
- Synthetic hydrocarbons especially polyolefins are well known in the art as API group IV base oils. These compounds are obtainable by polymerization of alkenes, especially alkenes having 3 to 12 carbon atoms, like propene, 1-hexene, 1-octene, 1-decene and 1-dodecene, or mixtures of these alkenes.
- Preferred PAOs have a number average molecular weight in the range of 200 to 10000 g/mol, more preferably 500 to 5000 g/mol.
- the hydraulic fluid composition comprises 70 to 95 wt.%, more preferably 80 to 95 wt.% and even more preferably 80 to 90 wt.% of the base oil (ii) selected from API group I, II, III or IV base oils or mixture thereof and 5 to 30 wt.%, more preferably 5 to 20 wt.% and even more preferred 10 to 20 wt.% of the polyalkyl(meth)acrylate viscosity index improver (i).
- the base oil (ii) selected from API group I, II, III or IV base oils or mixture thereof
- 5 to 30 wt.% more preferably 5 to 20 wt.% and even more preferred 10 to 20 wt.% of the polyalkyl(meth)acrylate viscosity index improver (i).
- hydraulic fluids corresponding to this invention having a viscosity index of at least 180, preferred of at least 200, especially preferred of at least 250 and a viscosity at 40°C of 15 cSt to 36 cSt, preferred between 15 cSt and 28 cSt, especially preferred between 19 cST and 28 cST. Furthermore it is advantageous, if the hydraulic fluid has a density at 15°C of 800 kg/m 3 to 860 kg/m 3 , preferred of 800 kg/m 3 to 840 kg/m 3 .
- the viscosity index improver might be added in a solvent.
- this solvent is also an API group I, II, III or IV oil. It is especially preferred that this solvent is identical to the base oil of the composition. Independently from the solvent that is used here it has to be calculated as part of the base oil in the composition.
- the VII solution that is added contains 20 to 40 wt.% solvent.
- the viscosity index can be determined according to ASTM D 2270.
- the hydraulic fluid composition according to this invention may also contain a Dispersant-lnhibitor package (Dl package) to improve parameters like foam, corrosion, oxidation, wear and others.
- This Dl package may comprise antioxidants, antifoam agents, anticorrosion agents and/or at least one Phosphorous or Sulfur containing antiwear agent.
- High VI hydraulic fluids are typically applied in mobile applications such as excavators. In these applications the hydraulic fluid has to deal with a broad variety of temperatures - very low starting temperatures in winter and very high temperatures under heavy load conditions.
- the high VI of the fluid is required to keep the viscosity as close as possible to the optimum.
- the optimum is defined by the balance between mechanical efficiency which requires a thin oil and volumetric efficiency which requires a thick oil to minimize losses by internal leakage in the pump. In regular operating conditions and especially under heavy load conditions volumetric efficiency becomes the dominant factor and the viscosity index improver can greatly improve the efficiency by increasing the viscosity of the fluid.
- the injection molding application is completely different compared to an excavator. The outside temperature is constant, the work cycle is well defined and heavy load conditions are avoided if possible. For this reason the oil temperature is rather constant and high VI base fluids are generally not used. Usually IS046 monograde fluids are recommended by the producers of injection molding machines.
- system performance of the hydraulic system can be improved.
- the expression system performance means the work productivity being done by the hydraulic system within a defined period of time.
- the system performance can be improved at least 5%, more preferably at least 10 %.
- the work cycles per hour can be improved.
- the monomer mixtures described above can be polymerized by any known method.
- Conventional radical initiators can be used to perform a classic radical polymerization. These initiators are well known in the art. Examples for these radical initiators are azo initiators like 2,2'-azodiisobutyronitrile (AIBN), 2,2'-azobis(2-methylbutyronitrile) and 1 ,1 azo-biscyclohexane carbonitrile; peroxide compounds, e.g.
- methyl ethyl ketone peroxide acetyl acetone peroxide, dilauryl peroxide, tert.-butyl per-2-ethyl hexanoate, ketone peroxide, me-thyl isobutyl ketone peroxide, cyclohexanone peroxide, dibenzoyl peroxide, tert.-butyl per-benzoate, tert.-butyl peroxy isopropyl carbonate, 2,5-bis(2-ethylhexanoyl-peroxy)-2,5-dimethyl hexane, tert.-butyl peroxy 2- ethyl hexanoate, tert.-butyl peroxy- 3,5,5-trimethyl hexanoate, dicumene peroxide, 1 ,1 bis(tert.
- butyl peroxy cyclohexane, 1 ,1 bis(tert. butyl peroxy) 3,3,5-trimethyl cyclohexane, cumene hydroperoxide and tert.-butyl hydroperoxide.
- Poly(meth)acrylates with a lower molecular weight can be obtained by using chain transfer agents. This technology is ubiquitously known and practiced in the polymer industry and is de-scribed in Odian, Principles of Polymerization, 1991 .
- ATRP Atom Transfer Radical Polymerization
- RAFT Reversible Addition Fragmentation Chain Transfer
- the polymerization can be carried out at normal pressure, reduced pressure or elevated pressure.
- the polymerization temperature is also not critical. However, in general it lies in the range of -20 to 200°C, preferably 60 to 120°C, without any limitation intended by this.
- the polymerization can be carried out with or without solvents.
- solvent is to be broadly understood here.
- the polymer is obtainable by a polymerization in API Group I, II or III mineral oil or in API group IV synthetic oil.
- the following hydraulic fluids are used:
- the injection molding machine that was used to create the data was Krauss Maffei KM 80/380 CX.
- the energy consumption of the hydraulic pump was calculated by measuring voltage and current of the pump motor with external test equipment (measuring amplifier MX 840 PAKAP; element for voltage recording MX 403 B, 1000V; both from Hottinger Baldwin Messtechnik GmbH). Before testing the system was flushed with the hydraulic fluid to be used and the oil parameters were checked to ensure that the previous oil was properly purged and no mixing with previous oils occurred.
- Table 1 shows viscometric data for fresh oils, oil fill for trial and for the oil collected after the trial.
- Figure 1 Description of a typical injection molding cycle
- the cycle begins when the mold closes (Step 1 ), followed by building up a pressure (Step 2a) which is required to keep the mold closed during injection.
- Step 2a After moving the extruder to the mold (Step 2b), material is injected (Step 3) and a working pressure is maintained to compensate material shrinkage during molding (Step 4).
- the work piece can be coated with a CoverForm ® process step (Step 4.1 , applied in Cycle A).
- the extruder is moved back when the cooling phase has started (Steps 5 and 6). At the end of the cooling phase the mold is opened (Step 7) and the work piece can be removed (Step 8).
- Table 2 shows the differences in energy consumption (savings are negative values) found for cycle A, cycle B and an evaluation of Step 1 and Step 2 taken from cycle A data.
- Steps 1 , 2, 4.1 , 7 and 8 are independent of the material which is injected. Consequently, the energy savings are independent on the plastic material properties.
- the coating step 4.1 is optional and part of the CoverForm ® process. Cycle A (with coating) and cycle B (without coating) evaluate the influence of this step on energy savings.
- Cycle A process steps which are material independent, with CoverForm ® process step
- Cycle B process steps which are material independent, without CoverForm ® process step
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Priority Applications (1)
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PL15750369T PL3183324T3 (en) | 2014-08-18 | 2015-08-07 | Hydraulic fluids in plastic injection molding processes |
Applications Claiming Priority (2)
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EP14181237 | 2014-08-18 | ||
PCT/EP2015/068272 WO2016026719A1 (en) | 2014-08-18 | 2015-08-07 | Hydraulic fluids in plastic injection molding processes |
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EP3183324A1 true EP3183324A1 (en) | 2017-06-28 |
EP3183324B1 EP3183324B1 (en) | 2020-12-30 |
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US (1) | US20170218295A1 (en) |
EP (1) | EP3183324B1 (en) |
CN (1) | CN106661490B (en) |
CA (1) | CA2957330C (en) |
PL (1) | PL3183324T3 (en) |
WO (1) | WO2016026719A1 (en) |
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WO2018108869A1 (en) | 2016-12-14 | 2018-06-21 | Evonik Oil Additives Gmbh | Use of polyesters as viscosity index improvers for aircraft hydraulic fluids |
CN116438282A (en) * | 2020-11-18 | 2023-07-14 | 赢创运营有限公司 | Compressor oil with high viscosity index |
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US5821313A (en) * | 1995-06-19 | 1998-10-13 | The Lubrizol Corporation | Dispersant-viscosity improvers for lubricating oil compositions |
JP3831203B2 (en) * | 2001-04-06 | 2006-10-11 | 三洋化成工業株式会社 | Viscosity index improver and lubricating oil composition |
US20070197410A1 (en) * | 2006-02-21 | 2007-08-23 | Rohmax Additives Gmbh | Energy efficiency in hydraulic systems |
WO2010043503A1 (en) * | 2008-10-14 | 2010-04-22 | Evonik Rohmax Additives Gmbh | Hydraulic fluid composition that reduces hydraulic system noise |
DE102010038615A1 (en) * | 2010-07-29 | 2012-02-02 | Evonik Rohmax Additives Gmbh | Polyalkyl (meth) acrylate for improving lubricating oil properties |
-
2015
- 2015-08-07 WO PCT/EP2015/068272 patent/WO2016026719A1/en active Application Filing
- 2015-08-07 CA CA2957330A patent/CA2957330C/en active Active
- 2015-08-07 CN CN201580043890.7A patent/CN106661490B/en active Active
- 2015-08-07 PL PL15750369T patent/PL3183324T3/en unknown
- 2015-08-07 US US15/326,076 patent/US20170218295A1/en not_active Abandoned
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PL3183324T3 (en) | 2021-08-02 |
WO2016026719A1 (en) | 2016-02-25 |
EP3183324B1 (en) | 2020-12-30 |
CN106661490A (en) | 2017-05-10 |
CA2957330C (en) | 2022-04-26 |
CA2957330A1 (en) | 2016-02-25 |
CN106661490B (en) | 2020-02-28 |
US20170218295A1 (en) | 2017-08-03 |
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