EP0804404A1 - Basische zinkcarboxylate - Google Patents
Basische zinkcarboxylateInfo
- Publication number
- EP0804404A1 EP0804404A1 EP95923295A EP95923295A EP0804404A1 EP 0804404 A1 EP0804404 A1 EP 0804404A1 EP 95923295 A EP95923295 A EP 95923295A EP 95923295 A EP95923295 A EP 95923295A EP 0804404 A1 EP0804404 A1 EP 0804404A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acids
- weight
- content
- carbon
- zinc
- 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.)
- Withdrawn
Links
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 31
- 239000011701 zinc Substances 0.000 title claims abstract description 31
- -1 zinc carboxylates Chemical class 0.000 title claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 40
- 150000007513 acids Chemical class 0.000 claims abstract description 24
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000344 soap Substances 0.000 claims abstract description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000004032 superbase Substances 0.000 claims abstract description 11
- 239000003381 stabilizer Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims abstract description 5
- 239000004800 polyvinyl chloride Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000007525 superbases Chemical class 0.000 claims abstract description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- 239000001569 carbon dioxide Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011787 zinc oxide Substances 0.000 claims description 5
- 150000004715 keto acids Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000005587 bubbling Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 229940007718 zinc hydroxide Drugs 0.000 claims description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NZQMQVJXSRMTCJ-UHFFFAOYSA-N 3-Methyl-hexanoic acid Chemical compound CCCC(C)CC(O)=O NZQMQVJXSRMTCJ-UHFFFAOYSA-N 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- QJRRBVNPIKYRQJ-UHFFFAOYSA-N 10-methylundecanoic acid Chemical compound CC(C)CCCCCCCCC(O)=O QJRRBVNPIKYRQJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- DGZZHLSSAUIDSX-UHFFFAOYSA-N 3-ethyloctanoic acid Chemical compound CCCCCC(CC)CC(O)=O DGZZHLSSAUIDSX-UHFFFAOYSA-N 0.000 description 1
- HHGZJCMMPUJXIF-UHFFFAOYSA-N 4,5-dimethylhexanoic acid Chemical compound CC(C)C(C)CCC(O)=O HHGZJCMMPUJXIF-UHFFFAOYSA-N 0.000 description 1
- CNQGBTJIGDAYTK-UHFFFAOYSA-N 4-ethylnonanoic acid Chemical compound CCCCCC(CC)CCC(O)=O CNQGBTJIGDAYTK-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000005473 octanoic acid group Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
Definitions
- the present invention relates to new basic zinc carboxylate, both liquid and solid compositions, a method for their preparation and their use as lubricant additives, as polymer stabilisers, as promoters or emuisifiers for rubber and fungicides.
- the invention provides an effective stabiliser for use in polyvinyl chloride which, may replace the more toxic Cadmin, Lead and Barium stabilisers currently used.
- the present invention therefore provides solid zinc superbase soaps in the form of zinc carboxylates, the carboxylic acids consisting of a mixture or otherwise of saturated organic carboxylic acids containing from 7 to 13 carbon atoms, having the following characteristics, optionally the products may also contain zinc carbonate. a linear acid content of between 0 and 40% by weight,
- the zinc superbase soaps are preferably prepared from saturated C ⁇ , Cg and C10 organic carboxylic acids which consist of isomeric mixtures and which are generally known as oxo acids. These oxo acids are characterized by a low linear acid content, generally less than or equal to 10% by weight, a low content of acids which are branched on carbon 2, generally less than or equal to 10% by weight, and a high content of acids which are mono- or polysubstituted on carbon 3 and/or carbons of higher rank, which is generally greater than 80% by weight.
- the oxo acids are obtained by hydroformylation of C7, C ⁇ and Cg olefins, followed by an oxidation.
- the zinc soaps according to the invention are prepared from the C ⁇ saturated carboxylic acid (that is containing 8 carbon atoms) marketed under the trademark Cekanoic, this acid consisting of an isomeric mixture of octanoic acids containing at most 10% by weight of n-octanoic acid, at most 10% by weight of C ⁇ acids which are branched on carbon 2 and at least 80% by weight of C ⁇ acids which are branched on carbon 3 and/or the carbons of higher rank.
- Cekanoic this acid consisting of an isomeric mixture of octanoic acids containing at most 10% by weight of n-octanoic acid, at most 10% by weight of C ⁇ acids which are branched on carbon 2 and at least 80% by weight of C ⁇ acids which are branched on carbon 3 and/or the carbons of higher rank.
- Cekanoic C 10 ac 'd
- organic carboxylic acids which are also suitable for the present invention there may also be added the derivatives which are mono- or polysubstituted in the 3-position and/or of higher rank of the acids corresponding to heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undeca ⁇ oic acid and dodeca ⁇ oic acid.
- these include, for example, 3-methylhexanoic acid, isooctanoic acid, 4,5-dimethylhexanoic acid, isononanoic acid,
- the present invention also relates to a process for the preparation of the zinc superbase soaps described above, according to which a zinc oxide and/or hydroxide is reacted with the appropriate acid, with stirring.
- the reaction may include the addition of carbon dioxide (CO2) which is bubbled through the reaction mixture and at least one organic carboxylic acid, in the presence of at least one promoter which make CO2 fixation easier and at least one catalyst, and in that the water formed during the reaction is removed.
- CO2 carbon dioxide
- the process is characterized in that the reaction is performed in at least one organic solvent at a temperature of between 80 and 120°C, and in that the said acid is a saturated organic carboxylic acid containing from 7 to 13 carbon atoms, in which the content of linear acids is less than or equal to 40% by weight, in which the content of acids branched on carbon 2 is less than or equal to 20% by weight, and in which the content of acids branched on carbon 3 and/or the carbons of higher rank is equal to or higher than 40% by weight.
- the organic solvent may be removed preferably by evaporation.
- the organic solvent is allowed to evaporate during the reaction and is recycled into the reaction mixture so as to produce therein a bubbling action which promotes the reaction.
- a plasticiser ester such as a phthalate or adipate may be used as the solvent which is particularly useful when the zinc carboxylate is to be used as a stabiliser for polyvinyl chloride.
- At least one nonpolar organic solvent chosen from naphtha, hexane, kerosene, benzene, toluene or xylene is used among the organic solvents which can be used in the process according to the invention. It is also possible to use a mixture of paraffinic hydrocarbons of mineral or synthetic origin, preferably containing a low proportion of aromatic and/or naphthenic hydrocarbons, such as white spirit.
- polar organic solvents such as alcohols, for example 1-butanol, 2-butanol, ethylene glycol, propylene glycol, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol and its ethers, mixtures of alcohols derived from paraffin, or methyl ethyl ketone.
- the molar ratio of zinc to the organic carboxylic acid employed in the reaction is generally between 0.55 and 2, which corresponds to a basicity of between 1.1 and 4.
- an hourly flow rate of carbon dioxide is imposed such that the hourly mass ratio of carbon dioxide to zinc is between 0.5 and 2, and preferably between 0.7 and 1.5.
- metal oxides for example, aluminium oxide AI2O3, silver oxide Ag2 ⁇ , magnesium oxide MgO, and zinc carboxylates such as zinc octanoate.
- labile hydrogen compounds such as alcohols, for example methanol, 2-propanol, octyl alcohol, ethylene glycol, triethylene glycol, strearyl alcohol, cyclohexylene glycol alcohol, cyclohexyl alcohol, aromatic alcohols such as phenol; amines, for example aniline, phenylenediamine, or dodecylamine; or, yet again, a mixture of alcohols and/or amines, for example of methanol and aqueous ammonia.
- alcohols for example methanol, 2-propanol, octyl alcohol, ethylene glycol, triethylene glycol, strearyl alcohol, cyclohexylene glycol alcohol, cyclohexyl alcohol, aromatic alcohols such as phenol; amines, for example aniline, phenylenediamine, or dodecylamine; or, yet again, a mixture of alcohols and/or amines, for example of methanol and a
- the material used in methanol which gives the highest basicities and the shortest filtration times during the preparation of the calcium soap according to the invention.
- the promoters are used in a proportion of 1 to 25% by weight of final zinc salt, and preferably in a proportion of 5 to 15%.
- the solution was slowly heated to 165°C to remove the water from the reactor 15 and maintained at 165°C until no more water comes over.
- the solution was slowly heated to 110°C and then put vacuum on it to remove the water from the reactor. Filtration was carried out at 110°C to yield the end 25 product as a viscous light yellow liquid.
- the end product is a clear product. 35
- the Toluene is evaporated and a white solid paste is formed.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9411698 | 1994-06-10 | ||
| GB9411698A GB9411698D0 (en) | 1994-06-10 | 1994-06-10 | Improved basic zinc carboxylates |
| PCT/EP1995/002247 WO1995034524A1 (en) | 1994-06-10 | 1995-06-08 | Basic zinc carboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0804404A1 true EP0804404A1 (de) | 1997-11-05 |
Family
ID=10756558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP95923295A Withdrawn EP0804404A1 (de) | 1994-06-10 | 1995-06-08 | Basische zinkcarboxylate |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0804404A1 (de) |
| CA (1) | CA2200777A1 (de) |
| GB (1) | GB9411698D0 (de) |
| WO (1) | WO1995034524A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19904139A1 (de) | 1999-02-03 | 2000-08-10 | Cognis Deutschland Gmbh | Verfahren zur Herstellung überbasischer Zinkseifen |
| JP2003522734A (ja) | 1999-06-25 | 2003-07-29 | アーチ ケミカルズ，インコーポレイテッド | 銀、銅、又は亜鉛イオンにより効力増大したピリチオン殺生物剤 |
| BRPI0309457B1 (pt) | 2002-04-22 | 2017-02-21 | Procter & Gamble | composições para cuidados pessoais que contém um material contendo zinco em uma composição aquosa de tensoativo |
| US8491877B2 (en) * | 2003-03-18 | 2013-07-23 | The Procter & Gamble Company | Composition comprising zinc-containing layered material with a high relative zinc lability |
| US9381148B2 (en) | 2003-03-18 | 2016-07-05 | The Procter & Gamble Company | Composition comprising particulate zinc material with a high relative zinc lability |
| US9381382B2 (en) | 2002-06-04 | 2016-07-05 | The Procter & Gamble Company | Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network |
| US9353026B2 (en) * | 2013-07-19 | 2016-05-31 | Baker Hughes Incorporated | Oil soluble hydrogen sulfide scavenger |
| CN115397800B (zh) * | 2020-04-23 | 2026-02-06 | 日油株式会社 | 羧酸锌组合物及含有羧酸锌组合物的羧酸锌溶液 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3730943A (en) * | 1965-09-03 | 1973-05-01 | Cincinnati Milacron Chem | Stabilized vinyl chloride polymers |
| CA1204755A (en) * | 1978-10-26 | 1986-05-20 | Jacobus J. Zeilstra | Derivatives of branched-chain monocarboxylic acids, engine lubricating oils, lubricant compositions for polymers, wax compositions in which these derivatives are incorporated and a process for preparing said branched-chain monocarboxylic acids |
| GB9121736D0 (en) * | 1991-10-14 | 1991-11-27 | Exxon Chemical Patents Inc | Improved overbased carboxylates |
-
1994
- 1994-06-10 GB GB9411698A patent/GB9411698D0/en active Pending
-
1995
- 1995-06-08 CA CA 2200777 patent/CA2200777A1/en not_active Abandoned
- 1995-06-08 EP EP95923295A patent/EP0804404A1/de not_active Withdrawn
- 1995-06-08 WO PCT/EP1995/002247 patent/WO1995034524A1/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9534524A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2200777A1 (en) | 1995-12-21 |
| WO1995034524A1 (en) | 1995-12-21 |
| GB9411698D0 (en) | 1994-08-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4810398A (en) | Preparation of a basic salt | |
| US5501807A (en) | Overbased carboxylates | |
| US10407558B2 (en) | Liquid compositions of overbased calcium carboxylate and process for its preparation | |
| US4824585A (en) | Calcium soaps possessing a high basicity reserve | |
| WO1995034524A1 (en) | Basic zinc carboxylates | |
| EP0450874A2 (de) | Überbasische Calixarate, Verfahren zu deren Herstellung, diese enthaltende Zusammensetzungen und deren Anwendung als Schmierölzusatzstoffe | |
| JP2004527634A5 (de) | ||
| WO1994026686A1 (en) | Improved basic calcium carboxylates | |
| US11702386B2 (en) | Processes for the manufacture of secondary fatty alcohols, internal olefins and internal olefin sulfonates | |
| EP0690837A1 (de) | Basische calciumcarboxylate | |
| US4014910A (en) | Process for the preparation of an (ar)alkane carboxylic acid | |
| US6613723B2 (en) | Overbased barium complexes of C8 to C10 carboxylic acids | |
| US5021598A (en) | Process for making bismuth carboxylates | |
| EP0553251B1 (de) | Metallcarboxylate | |
| US5861523A (en) | Metal carboxylates | |
| US2829156A (en) | alpha-hydroperoxyisopropylbenzoic acids, their salts and esters and method of preparation | |
| RU2239625C2 (ru) | Способ получения солей бета-(4-гидрокси-3,5-ди-трет-бутилфенил)-пропионовой кислоты |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19970317 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): BE CH DE ES FR GB IT LI LU NL SE |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: EXXONMOBIL CHEMICAL PATENTS INC. |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20020103 |