EP0698007A1 - Improved basic calcium carboxylates - Google Patents
Improved basic calcium carboxylatesInfo
- Publication number
- EP0698007A1 EP0698007A1 EP94918321A EP94918321A EP0698007A1 EP 0698007 A1 EP0698007 A1 EP 0698007A1 EP 94918321 A EP94918321 A EP 94918321A EP 94918321 A EP94918321 A EP 94918321A EP 0698007 A1 EP0698007 A1 EP 0698007A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- calcium
- acids
- weight
- content
- carbon
- 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- Withdrawn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
- 239000011575 calcium Substances 0.000 title claims abstract description 33
- 229910052791 calcium Inorganic materials 0.000 title claims abstract description 33
- -1 calcium carboxylates Chemical class 0.000 title claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 27
- 150000007513 acids Chemical class 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000004032 superbase Substances 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000004014 plasticizer Substances 0.000 claims abstract description 9
- 239000000344 soap Substances 0.000 claims abstract description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 1
- 239000000292 calcium oxide Substances 0.000 claims 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 14
- 229920000915 polyvinyl chloride Polymers 0.000 abstract description 8
- 239000004800 polyvinyl chloride Substances 0.000 abstract description 8
- 239000003381 stabilizer Substances 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 3
- 150000004715 keto acids Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- VSAJTRPXXNCHGB-UHFFFAOYSA-N 9-methyl-decanoic acid Chemical compound CC(C)CCCCCCCC(O)=O VSAJTRPXXNCHGB-UHFFFAOYSA-N 0.000 description 1
- 102100035474 DNA polymerase kappa Human genes 0.000 description 1
- 101710108091 DNA polymerase kappa Proteins 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- ZCZLQYAECBEUBH-UHFFFAOYSA-L calcium;octadec-9-enoate Chemical compound [Ca+2].CCCCCCCCC=CCCCCCCCC([O-])=O.CCCCCCCCC=CCCCCCCCC([O-])=O ZCZLQYAECBEUBH-UHFFFAOYSA-L 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000005473 octanoic acid group Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/414—Preparation of superbasic salts
-
- 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
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
Definitions
- the present invention relates to new basic calcium carboxylate compositions, a method for their preparation and their use as polymer stabilisers, particularly stabilisers for polyvinyl chloride.
- Basic calcium carboxylates are known in many forms and are commonly used as additives in various lubricant systems and to impart anticorrosion properties to coatings such as temporary and permanent coatings for metals and as polymer stabilisers since they have a higher calcium level as possible in these products to reduce the amount of additive required to provide the desired calcium level. It
- European Patent 0234149 produces an oil solution of a high calcium content calcium carboxylate which is not useful in applications where the oil will act as a contaminant such as a plastics stabiliser. Furthermore the presence of the oil solvent increases the bulk and thus transportation costs. Other processes use organic solvents which can impart an undesirable odour to the final product.
- the present invention therefore provides a solution in a plasticiser ester of a calcium superbase soaps in the form of calcium carbonate and calcium 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:
- the invention further provides a process for the manufacture of such a solution comprising producing the overbased calcium superbase salt using the plasticiser ester as the reaction medium.
- the calcium superbase soaps are preferably prepared from saturated C ⁇ , Cg and Cio 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 calcium 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.
- this acid makes it possible to obtain calcium soaps with a very high basicity of the order of 500 or higher.
- organic carboxylic acids which are also suitable for the present invention there may also be added the derivatives which are mono- or polysubstituted in he 3-position and/or of higher rank of the acids corresponding to heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid and dodecanoic acid.
- Suitable plasticiser ester are those typically used for plasticising polyvinyl chloride such as alkyl phthalates for example dioctyl phthalate, dinonyl phthalate and adipates and trimellitates.
- the ester should have a flash point above 120 ° C, and should be compatible with polyvinyl chloride and other additives such as phosphites, UV stabilisers, other metal containing additives particularly zinc stabilisers and other plasticisers traditionally used in PVC.
- solutions of the superbase calcium carboxylate in the ester may be obtained containing as much as 10 wt% calcium, typically between 5 and 10 wt%, although the viscosity tends to be higher than desirable at the higher calcium levels.
- the molar ratio of calcium 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.
- the basicity is equal to the ratio of equivalents of calcium to the equivalents of carboxylic acids which are employed, that is to say, to the molar ratio of the calcium concentration to that of the carboxylic acids, multiplied by 2.
- the promoters are used in a proportion of 1 to 25% by weight of final calcium salt, and preferably in a proportion of 5 to 15%.
- Ca(OH)2 is reacted with Cekanoic Cs acid in the presence of injected CO2 with methanol as promoter and Exxsol D40 as reaction diluent in the following proportions.
- solid calcium salt is prepared by evaporating the solvent just by heating up the liquid sample in a cup exposed to air. Crystals are formed which then are crushed in a crucible. The resulted powder is dissolved in dinonyl phthalate and heated up to 80-120 ' C to give a solution of 0.49 g solid in 20.07 g DINP. The solution was heated for 1 hour at 120 ° C and the solution remained clear and yellow with no smell of alcohol showing effective stabilisation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9309946 | 1993-05-14 | ||
| GB939309946A GB9309946D0 (en) | 1993-05-14 | 1993-05-14 | Improved basic calcium carboxylates |
| PCT/EP1994/001566 WO1994026686A1 (en) | 1993-05-14 | 1994-05-13 | Improved basic calcium carboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0698007A1 true EP0698007A1 (en) | 1996-02-28 |
Family
ID=10735473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94918321A Withdrawn EP0698007A1 (en) | 1993-05-14 | 1994-05-13 | Improved basic calcium carboxylates |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0698007A1 (cs) |
| JP (1) | JPH08510213A (cs) |
| GB (1) | GB9309946D0 (cs) |
| TW (1) | TW251306B (cs) |
| WO (1) | WO1994026686A1 (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07286080A (ja) * | 1994-02-24 | 1995-10-31 | Nissan Fuero Yuki Kagaku Kk | ハロゲン含有樹脂組成物 |
| US5519076A (en) * | 1994-02-24 | 1996-05-21 | Nissan Ferro Organic Chemical Co, Ltd. | Halogen-containing resin composition |
| US5919741A (en) * | 1998-01-20 | 1999-07-06 | The Lubrizol Corporation | Overbased carboxylate gels |
| US6835328B2 (en) | 2002-07-08 | 2004-12-28 | Crompton Corporation | Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same |
| US20040006165A1 (en) * | 2002-07-08 | 2004-01-08 | Julius Fakinlede | Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same |
| ITVA20110032A1 (it) | 2011-11-29 | 2013-05-30 | Lamberti Spa | Composizioni di sali surbasici di calcio carbossilato/carbonato |
| CN111718655A (zh) * | 2020-07-01 | 2020-09-29 | 中山华明泰科技股份有限公司 | 一种复合异辛酸钙制备方法及应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1528804A (fr) * | 1967-04-27 | 1968-06-14 | Prod Chim Et De Synthese Soc D | Stabilisants liquides au plomb pour les polymères et copolymères du chlorure de vinyle |
| FR2592391B1 (fr) * | 1985-12-30 | 1988-02-05 | Charbonnages Ste Chimique | Savons de calcium possedant une reserve de basicite elevee. |
| GB9121736D0 (en) * | 1991-10-14 | 1991-11-27 | Exxon Chemical Patents Inc | Improved overbased carboxylates |
-
1993
- 1993-05-14 GB GB939309946A patent/GB9309946D0/en active Pending
-
1994
- 1994-05-13 WO PCT/EP1994/001566 patent/WO1994026686A1/en not_active Ceased
- 1994-05-13 EP EP94918321A patent/EP0698007A1/en not_active Withdrawn
- 1994-05-13 JP JP6524676A patent/JPH08510213A/ja active Pending
- 1994-06-09 TW TW83105255A patent/TW251306B/zh active
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9426686A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994026686A1 (en) | 1994-11-24 |
| JPH08510213A (ja) | 1996-10-29 |
| TW251306B (cs) | 1995-07-11 |
| GB9309946D0 (en) | 1993-06-30 |
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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: 19951123 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE |
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| D17P | Request for examination filed (deleted) | ||
| R17P | Request for examination filed (corrected) |
Effective date: 19951121 |
|
| 17Q | First examination report despatched |
Effective date: 19961111 |
|
| ET | Fr: translation filed | ||
| 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: 19970522 |