GB2124221A - Coated powder of ???,???- ethylenically unsaturated carboxylic acid metal salt and production thereof - Google Patents
Coated powder of ???,???- ethylenically unsaturated carboxylic acid metal salt and production thereof Download PDFInfo
- Publication number
- GB2124221A GB2124221A GB08318294A GB8318294A GB2124221A GB 2124221 A GB2124221 A GB 2124221A GB 08318294 A GB08318294 A GB 08318294A GB 8318294 A GB8318294 A GB 8318294A GB 2124221 A GB2124221 A GB 2124221A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- unsaturated carboxylic
- carboxylic acid
- ethylenically unsaturated
- fatty acid
- 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 32
- 239000000843 powder Substances 0.000 title claims abstract description 27
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 25
- 239000002184 metal Substances 0.000 title claims abstract description 25
- 150000003839 salts Chemical class 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 claims abstract description 28
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 24
- 229930195729 fatty acid Natural products 0.000 claims abstract description 24
- 239000000194 fatty acid Substances 0.000 claims abstract description 24
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 20
- 238000002844 melting Methods 0.000 claims abstract description 13
- 230000008018 melting Effects 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 24
- 235000021355 Stearic acid Nutrition 0.000 claims description 16
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 16
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 239000008117 stearic acid Substances 0.000 claims description 16
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 13
- 235000021314 Palmitic acid Nutrition 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 8
- 239000011787 zinc oxide Substances 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000011667 zinc carbonate Substances 0.000 claims 1
- 229910000010 zinc carbonate Inorganic materials 0.000 claims 1
- 235000004416 zinc carbonate Nutrition 0.000 claims 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims 1
- 229940007718 zinc hydroxide Drugs 0.000 claims 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 abstract description 12
- 239000005060 rubber Substances 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000015271 coagulation Effects 0.000 description 12
- 238000005345 coagulation Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 150000003751 zinc Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 alkaryl carboxylic acid Chemical class 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Powder of ???,???-ethylenically unsaturated carboxylic acid metal salt is coated with a C10-C24 fatty acid having a melting point of at least 30 DEG C. A powder of ???,???-ethylenically unsaturated carboxylic acid metal salt, especially zinc acrylate, is useful as a component to make a solid golf ball, but is disadvantageously liable to coagulate in a rubber composition or to adhere to the roll or to the inner surface of a blender during the preparation of the rubber compound. In order to avoid such problems a powder of the metal salt is coated with the fatty acid mentioned above.
Description
SPECIFICATION
Coated powder of a ethylenically unsaturated carboxylic acid metal salt and production thereof
The present invention relates to a coated powder of a,P, ethylenically unsaturated carboxylic acid metal salt and production thereof.
It has been known that properties of a golf ball or a tyre can be improved by blending an ethylenically unsaturated carboxylic acid metal salt into rubber composition thereof. Especially, the improvement in core hardness, impact resistance and durability of solid golf ball is achieved by the addition of the metal salt.
On the contrary, the cg, -ethylenically unsaturated carboxylic acid metal salt is liable to adhere to blender and to coagulate in rubber at the formation, which causes a crack and a distortion and deteriorates the workability.
Additionally, the a,-ethylenically unsaturated carboxylic acid metal salt, which is prepared by the mixing of the acid and metal compound in a solvent, adheres to reaction vessel or stirrer during the reaction, and is contaminated into recovered solvent by bumping at the removement of the solvent, so that the recovery of the solvent as well as the yield of the reaction product reduces, which makes remarkable economical loss.
The present invention relates to a powder of an cu,P-ethylenically unsaturated carboxylic acid metal salt free from coagulation and the production thereof improved in such problems.
According to the present invention, powder of a,$ethylenically unsaturated carboxylic acid metal salt coated with a C,0424 fatty acid having a melting point of at least 300C is provided.
The cr,P-ethylenically unsaturated carboxylic acid of the present invention is preferably selected from aliphatic or arylaliphatic, alkaryl carboxylic acid having carbon atoms of from 3 to 9 such as acrylic acid, methacrylic acid, crotonic acid, sorbic acid, isocrotonic acid, cinnamic acid, isocinnamic acid, itaconic acid and the like. Particularly preferable cg,-ethylenically unsaturated carboxylic acid is acrylic acid or methacrylic acid, especially acrylic acid.
Metal compound used for forming the acid salt of the present invention includes oxides, carbonates, hydroxides or others polyvalent metal such as zinc, magnesium, cadmium, calcium, aluminum, barium, strontium, copper(ic), cobalt(ic), tin and the like. Most preferable one is zinc compound, particularly zinc oxide. Zinc salt of the acrylic or the methacrylic acid is the most useful compound for the improvement of the properties of solid gold ball and liable to cause to aforementioned problems such as coagulation, adhesion and loss during the production.
Preferable fatty acid in accordance with the present invention has carbon atoms of from ten to twenty-four and a melting point of at least 300C.
A fatty acid of less than ten carbon atoms may replace the metal salt with the a,-ethylenically unsaturated carboxylic acid, and a fatty acid having carbon atoms of more than 24 is economically unsuitable. Preferable fatty acid of the present invention includes capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachic acid, behenic acid, lignoceric acid, and the like. Most preferable fatty acid is stearic acid and palmitic acid.The fatty acid may have a branch or an unsaturated group provided that the melting point thereof is at least 300C. In case of the melting point being less than 300C the coated film of the fatty acid melts at room temperature, and on the contrary being more than 850C of the melting point, an uneven coated film may be formed so as to cause coagulation or adhesion at the intermixture of the salt into rubber or plastics. Preferable melting point is from 40 to 750C.
The amount of the fatty acid is preferably about 5 to 20 parts of weight based on 100 parts by weight of o',-ethylenically unsaturated carboxylic acid. The fatty acid of less than about 5 parts by weight is insufficient to coat the metal salt, whereas the fatty acid of more than 20 parts by weight may ionically decompose peroxide incorporated into rubber or plastic compound as a radical initiator for polymerization of a ethylenically unsaturated carboxylic acid metal salt, so that the physical properties of an obtained cured rubber or plastics deteriorate in some cases.
Further aspect of the present invention is a production of the coated powder of a,P- ethylenically unsaturated carboxylic acid metal salt which comprises reacting the unsaturated carbocylic acid with metallic compound in the presence of solvent, adding a C1OC24 fatty acid having a melting point of at least 300C to the reaction product with stirring and then drying the resultant.
According to the present invention, the reaction of the cr"ss-ethylenically unsaturated carboxylic acid and the metalic compound is preferably carried out in the presence of an organic solvent, preferably hydrocarbon solvent such as benzene, toluene, xylene, n-heptane, nhexane and the like and alcohols such as methanol, ethanol and the like, which may contain a small amount of water.
A preferable temperature of the reaction is about 20 to 700C but not restricted. After the reaction of the unsaturated carboxylic acid with metalic compound, C1OC24 fatty acid having a melting point of at least 30"C is added to the reaction product in the amount of 5 to 20 parts by weight based on 100 parts by weight of the unsaturated carboxylic acid. The fatty acid may be added to the solution or dispersion of the reaction product in the form of a powder, a solution or a melt at or to about 40--90"C. After mixing, the solution is dried by a conventional method such as evaporation of the solvent under a reduced pressure to give a coated fine powder of a.,B- ethylenically unsaturated carboxylic acid metal salt free from coagulation in a high yield.
In the present invention, the unsaturated carboxylic acid may contain polymerizationinhibitor such as hydroquinone and hydroquinone monomethyl ether, which does not affect on curing of the rubber or plastics at all.
According to the present invention, the yield of the unsaturated carboxylic acid salt powder increases remarkably, and the coagulation of the salt in rubber or plastics and adhesion on rolls are not formed during the formulation of the rubber or plastics. In addition, a golf ball made from the rubber containing the coated ez,-ethylenically unsaturated carboxylic acid metal salt of the present invention is remarkably improved in physical properties such as core hardness, durability and so in comparison to a golf ball produced using a non-coated unsaturated carboxylic acid.This is unexpected from a common sense that a free carboxylic acid acts as an organic acid to decompose radical catalyst such as peroxides and ionic degradation of peroxide catalyst due to free carboxylic acid, that is, free fatty acid used as coatings in the present invention, would have been expected to cause a deterioration of the physical properties of the golf ball.
Example 1
Zinc oxide (600 g) and toluene (200 ml) are charged into a jacket type vertical mixer (5 litre) and suspended by stirring. To the resultant mixture, acrylic acid (1060 g) is added dropwise with stirring over 30 minutes to react at room temperature for 60 minutes to give zinc acrylate.
After the reaction, a solution prepared by dissolving stearic acid (130 g) into toluene (100 ml) at 45 to 500C is added to the zinc acrylate solution, followed by the stirring of the mixture for 30 minutes to form a slurry of zinc acrylate coated with stearic acid. The slurry is heated at 500C for 3 hours under 20 to 60 mmHg to evaporate the toluene and water to be dried without substantial amount of scattering and adhesion of the zinc salt. The dried coated zinc acrylate is a fine powder free from coagulation. The yield is 1620 g, heating loss of which is about 0.3 percent.
Comparative Example 1
Zinc acrylate is prepared by the same manner as described in Example 1 excepting coating with stearic acid. Yield of the zinc acrylate is 1120 g.
In the above process, the zinc acrylate is remarkably scattered during the removal of the solvent so as to mix into the removed solvent. It is difficult to collect the scattered and zinc acrylate contaminant during the removed solvent and to clean the internal surface of the reaction vessel, on which the zinc acrylate adheres. In addition to the loss of the zinc acrylate, a partial lump of the zinc acrylate is formed, which is difficult to be crushed to fine powder.
Comparative Example 2
Zinc acrylate as obtained in Comparative
Example 1 is crushed to a powder of 10 to 1 7 by grinder. The grinded zinc acrylate (30 parts by weight) is blended into polybutadiene (100 parts by weight) using 6 inch roll. The resultant rubber compound contains many coagulations of larger than 0.5 mm and adheres remarkably on the roll.
Example 2
In the manner of Example 1, palmitic acid (130 g) is used replacing the stearic acid to give a fine powder of zinc acrylate coated with palmitic acid free from coagulation, the yield of which is 1620 g and heating loss is 0.3 percent.
During the removal of the solvent, the scattering and adhesion of zinc acrylate are not observed.
Example 3
Zinc oxide (1400 g) and toluene (1960 ml) are charged into a jacket type kneader (10 litter) and homogenized by kneading. While kneading, acrylic acid (2477 g) is added dropwise to the mixture over 60 minutes and reacts for one hour at 40 to 500C. After the reaction, stearic acid (376 g) is added to the reaction mixture with the continuation of kneading, heated to 750C and stirred for 30 minutes to coat the resultant zinc acrylate with the stearic acid. The toluene and water are removed by heating for two hours under 300 to 200 mmHg to give a dried fine powder of the zinc acrylate free from coagulation. The yield of the salt is 3720 g, heating loss of which is about 0.25 percent. In the above process a substantial amount of scattering and adhesion of the zinc salt are not observed.
Example 4
In the manner of Example 3, palmitic acid (376 g) is used replacing the stearic acid to give a fine powder of zinc acrylate coated with palmitic acid free from coagulation, the yield of which is 3720 g, and the heating loss is 0.25 percent.
During the removal of the solvent, the scattering and adhesion of zinc acrylate are not observed.
Example 5
Zinc oxide (2260 g) and methanol (2000 ml) are charged into a jacket type kneader (101itter) to make a slurry by kneading, followed by the dropwise addition of acrylic acid (4000 g) over 30 minutes. After the addition, the reaction is continued for about one hour, and then stearic acid (820 g) is added to the reaction mixture at 40 to 500C with stirring to coat zinc acrylate in the reaction mixture. The methanol is removed at 700C by the passing of vapor through the jacket, and the residue is taken out from the kneader to be dried at a low temperature, i.e. 400C to give zinc acrylate (6290 g), the heating loss of which is 0.25 percent.
In the above process, a substantial amount of scattering and adhesion of the zinc salt are not observed.
Example 6
In the manner of Example 5, palmitic acid (820 g) is used replacing the stearic acid to give a fine powder of zinc acrylate coated with palmitic acid free from coagulation, the yield of which is 620 g and heating loss is 0.25 percent.
During the removal of the solvent, the scattering and adhesion of zinc acrylate are not observed.
Example 7
Zinc oxide (900 g) and benzene (3000 ml) are charged into a jacket type vertical mixer (5 litter) and stirred to form a suspension. After acrylic acid (1590 g) is added dropwise to the suspension over 30 minutes with stirring, the reaction is continued for 60 minutes at a room temperature.
To the reaction mixture, a solution of stearic acid (80 g) in benzene (500 ml), which is prepared by heating the mixture thereof at 45 to 50"C, is added with stirring for 30 minutes to form a slurry, which is then heated at 500C under 275 to 100 mmHg for two hours to remove the solvent and water to give zinc acrylate coated with stearic acid (492 g), the heating loss of which is 0.25 percent.
In the above process, a substantial amount of scattering and adhesion of the zinc salt are not observed.
Example 8
In the manner of Example 7, palmitic acid (80 g) is used replacing the stearic acid to give a fine powder of zinc acrylate coated with palmitic acid free from coagulation, the yield of which is 492 g, and heating loss is 0.25 percent.
At the removal of the solvent, the scattering and adhesion of zinc acrylate are not observed.
Claims (14)
1. Powder of a,gethylenically unsaturated carboxylic acid metal salt, which is coated with a C10-C24 fatty acid having a melting point of at least 30"C.
2. The powder according to Claim 1, in which the ,p,ethylenically unsaturated carboxylic acid is acrylic acid or methacrylic acid.
3. The powder according to Claim 1, in which metal is one selected from the group consisting of zinc, magnesium, cadmium, calcium, aluminum, barium, strontium, copper(ic), cobalt(ic) and tin.
4. The powder according to Claim 3, in which metal is zinc.
5. The powder according to Claim 1, in which the cr,P-ethylenically unsaturated carboxylic acid metal salt is zinc acrylate.
6. The powder according to Claim 1, in which the melting point of the fatty acid is 40 to 750C.
7. The powder according to Claim 1, in which the fatty acid is palmitic acid or stearic acid.
8. A process for a production of a,/3-ethyleni- cally unsaturated carboxylic acid metal salt coated with a C10-C24 fatty acid, which comprises reacting the a,/3-ethylenically unsaturated carboxylic acid with a metallic compound in organic solvent, adding a C10-C24 fatty acid having a melting point of at least 300C to the reaction product with stirring and then drying the resultant.
9. The process according to Claim 8, in which the ,-ethylenically unsaturated carboxylic acid is acrylic acid of methacrylic acid.
1 0. The process according to Claim 8, in which the metalic compound is oxides, carbonates or hydroxides of polyvalent metal.
11. The process according to Claim 8, in which the metal compound is zinc oxide, zinc hydroxide or zinc carbonate.
12. the process according to Claim 8, in which the melting point of the fatty acid is from 40 to 750C.
13. The process according to Claim 8, in which the fatty acid is palmitic acid or stearic acid.
14. The process according to Claim 8, in which the fatty acid is used in an amount from 5 to 20 parts by weight based on 100 parts by weight of ,-ethylenically unsaturated carboxylic acid.
1 5. The process according to Claim 8, in which the solvent is hydrocarbon or alcohol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11806982A JPS5921640A (en) | 1982-07-07 | 1982-07-07 | Preparation of zinc acrylate |
| JP9552083A JPS59219250A (en) | 1983-05-30 | 1983-05-30 | Production of unsaturated carboxylic acid metal salt |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8318294D0 GB8318294D0 (en) | 1983-08-10 |
| GB2124221A true GB2124221A (en) | 1984-02-15 |
| GB2124221B GB2124221B (en) | 1985-11-13 |
Family
ID=26436742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08318294A Expired GB2124221B (en) | 1982-07-07 | 1983-07-06 | Coated powder of a,b-ethylenically unsaturated carboxylic acid metal salt and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2124221B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7217829B2 (en) | 2002-11-11 | 2007-05-15 | Nippon Shokubai Co., Ltd. | Zinc acrylate and method for production thereof |
-
1983
- 1983-07-06 GB GB08318294A patent/GB2124221B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7217829B2 (en) | 2002-11-11 | 2007-05-15 | Nippon Shokubai Co., Ltd. | Zinc acrylate and method for production thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2124221B (en) | 1985-11-13 |
| GB8318294D0 (en) | 1983-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PE20 | Patent expired after termination of 20 years |