DE2265659C2 - Verfahren zur Herstellung von metallhaltigen Copolymeren - Google Patents
Verfahren zur Herstellung von metallhaltigen CopolymerenInfo
- Publication number
- DE2265659C2 DE2265659C2 DE2265659A DE2265659A DE2265659C2 DE 2265659 C2 DE2265659 C2 DE 2265659C2 DE 2265659 A DE2265659 A DE 2265659A DE 2265659 A DE2265659 A DE 2265659A DE 2265659 C2 DE2265659 C2 DE 2265659C2
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- metal
- degree
- copolymers
- neutralization
- 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.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 title claims description 126
- 229910052751 metal Inorganic materials 0.000 title claims description 50
- 239000002184 metal Substances 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 48
- 238000007127 saponification reaction Methods 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000003819 basic metal compounds Chemical class 0.000 claims description 6
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical group 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229910021645 metal ion Inorganic materials 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000004698 Polyethylene Substances 0.000 description 10
- 238000005342 ion exchange Methods 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- 239000000155 melt Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 239000002344 surface layer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229920001038 ethylene copolymer Polymers 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920003182 Surlyn® Polymers 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 229920005680 ethylene-methyl methacrylate copolymer Polymers 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004063 acid-resistant material Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 229920006225 ethylene-methyl acrylate Polymers 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920005588 metal-containing polymer Polymers 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/08—Copolymers of ethene
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7950371A JPS5318544B2 (OSRAM) | 1971-10-11 | 1971-10-11 | |
| JP10321771A JPS535716B2 (OSRAM) | 1971-12-21 | 1971-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2265659C2 true DE2265659C2 (de) | 1985-03-07 |
Family
ID=26420521
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2265659A Expired DE2265659C2 (de) | 1971-10-11 | 1972-10-10 | Verfahren zur Herstellung von metallhaltigen Copolymeren |
| DE2249578A Expired DE2249578C2 (de) | 1971-10-11 | 1972-10-10 | Verfahren zur Herstellung von metallhaltigen Copolymerisaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2249578A Expired DE2249578C2 (de) | 1971-10-11 | 1972-10-10 | Verfahren zur Herstellung von metallhaltigen Copolymerisaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3789035A (OSRAM) |
| CA (1) | CA978697A (OSRAM) |
| DE (2) | DE2265659C2 (OSRAM) |
| FR (1) | FR2157382A5 (OSRAM) |
| NL (1) | NL153213B (OSRAM) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3943111A (en) * | 1972-03-29 | 1976-03-09 | Hoechst Aktiengesellschaft | Process for preparing modified copolymers |
| US3976723A (en) * | 1972-12-15 | 1976-08-24 | Rohm And Haas Company | Preparation and use of acrylic ionomer elastomers |
| JPS5223673B2 (OSRAM) * | 1975-03-18 | 1977-06-25 | ||
| US4196267A (en) * | 1975-03-25 | 1980-04-01 | Asahi-Dow Limited | Extrusion foamed article and process for producing the same |
| US4071669A (en) * | 1976-06-24 | 1978-01-31 | The Goodyear Tire & Rubber Company | Metal salts of modified anhydride resin |
| GB1543136A (en) * | 1976-10-18 | 1979-03-28 | Sumitomo Chemical Co | Method for the preparation of water-insoluble hydrophilic gels |
| GB1587307A (en) * | 1977-03-04 | 1981-04-01 | Nitto Electric Ind Co | Antibacterial and antifungal material |
| US4346196A (en) * | 1980-09-10 | 1982-08-24 | E. I. Du Pont De Nemours And Company | Heat seal composition comprising a blend of metal neutralized polymers |
| US4469754A (en) * | 1980-09-10 | 1984-09-04 | E. I. Du Pont De Nemours And Company | Heat seal composition |
| DE3046144A1 (de) * | 1980-12-06 | 1982-07-15 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von mischpolymerisaten des ethylens |
| US4381376A (en) * | 1980-12-29 | 1983-04-26 | Allied Corporation | Preparation of low molecular weight copolymer salts |
| JPH0678384B2 (ja) * | 1987-04-30 | 1994-10-05 | 出光興産株式会社 | アイオノマ−樹脂およびその製造法 |
| US5397840A (en) * | 1991-09-03 | 1995-03-14 | Spalding & Evenflo Companies, Inc. | Golf ball cover having an ionic copolymer/non-ionic copolymer blend |
| US5516847A (en) * | 1991-09-03 | 1996-05-14 | Lisco, Inc. | Golf ball cover having an ionic copolymer/non-ionic copolymer blend |
| US5571878A (en) * | 1991-09-24 | 1996-11-05 | Chevron Chemical Company | Ethylene-alkyl acrylate copolymers and derivatives having improved melt-point temperatures and adhesive strength and processes for preparing same |
| JP3065398B2 (ja) * | 1991-09-25 | 2000-07-17 | 住友ゴム工業株式会社 | ゴルフボール |
| JPH0654929A (ja) * | 1992-08-06 | 1994-03-01 | Sumitomo Rubber Ind Ltd | ゴルフボール |
| US5321089A (en) * | 1993-03-30 | 1994-06-14 | Dunlop Slazenger Corporation | Golf ball cover |
| US6207759B1 (en) | 1993-04-08 | 2001-03-27 | E. I. Du Pont De Nemours And Company | Composition for a cover of a golf ball |
| JP2657618B2 (ja) * | 1993-11-09 | 1997-09-24 | 住友ゴム工業株式会社 | ゴルフボール |
| JP3441010B2 (ja) * | 1994-02-09 | 2003-08-25 | ブリヂストンスポーツ株式会社 | ゴルフボール |
| US7175543B2 (en) | 2005-01-26 | 2007-02-13 | Callaway Golf Company | Golf ball and thermoplastic material |
| US7156755B2 (en) * | 2005-01-26 | 2007-01-02 | Callaway Golf Company | Golf ball with thermoplastic material |
| US7312267B2 (en) * | 2005-02-23 | 2007-12-25 | Callaway Golf Company | Golf ball and thermoplastic material |
| US7612134B2 (en) * | 2005-02-23 | 2009-11-03 | Callaway Golf Company | Golf ball and thermoplastic material |
| ES2541450T3 (es) * | 2005-03-18 | 2015-07-20 | Kuraray Co., Ltd. | Resina de poliamida semiaromática |
| US7612135B2 (en) * | 2006-02-17 | 2009-11-03 | Callaway Golf Company | Golf ball and thermoplastic material |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3132120A (en) * | 1961-02-03 | 1964-05-05 | Du Pont | Method for the preparation of ethylene copolymers |
| NL288151A (OSRAM) * | 1961-08-31 | 1900-01-01 | ||
| US3249570A (en) * | 1962-11-15 | 1966-05-03 | Union Carbide Corp | Terpolymer of ethylene, alkyl acrylate and acrylic acid |
| BE695114A (OSRAM) * | 1966-03-18 | 1967-09-07 | ||
| US3553178A (en) * | 1967-09-07 | 1971-01-05 | Gulf Research Development Co | Carbon dioxide as an ethylene polymer coagulant |
| US3536682A (en) * | 1968-03-04 | 1970-10-27 | Gulf Research Development Co | Self-emulsifiable ethylene polymer compositions |
| US3679561A (en) * | 1970-06-22 | 1972-07-25 | Gulf Research Development Co | Treatment of ethylene unsaturated acid ester copolymer with alkaline medium |
-
1972
- 1972-10-10 FR FR7235829A patent/FR2157382A5/fr not_active Expired
- 1972-10-10 DE DE2265659A patent/DE2265659C2/de not_active Expired
- 1972-10-10 DE DE2249578A patent/DE2249578C2/de not_active Expired
- 1972-10-10 US US00295875A patent/US3789035A/en not_active Expired - Lifetime
- 1972-10-10 CA CA153,564A patent/CA978697A/en not_active Expired
- 1972-10-11 NL NL727213756A patent/NL153213B/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2249578C2 (de) | 1985-02-21 |
| US3789035A (en) | 1974-01-29 |
| CA978697A (en) | 1975-11-25 |
| AU4757772A (en) | 1974-01-24 |
| FR2157382A5 (OSRAM) | 1973-06-01 |
| NL153213B (nl) | 1977-05-16 |
| DE2249578A1 (de) | 1973-04-26 |
| NL7213756A (OSRAM) | 1973-04-13 |
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