DE2521843C3 - Verfahren zur Herstellung eines chlorierten Polymerisates, Mischpolymerisates oder Pfropfpolymerisates aus Vinylchlorid - Google Patents
Verfahren zur Herstellung eines chlorierten Polymerisates, Mischpolymerisates oder Pfropfpolymerisates aus VinylchloridInfo
- Publication number
- DE2521843C3 DE2521843C3 DE2521843A DE2521843A DE2521843C3 DE 2521843 C3 DE2521843 C3 DE 2521843C3 DE 2521843 A DE2521843 A DE 2521843A DE 2521843 A DE2521843 A DE 2521843A DE 2521843 C3 DE2521843 C3 DE 2521843C3
- Authority
- DE
- Germany
- Prior art keywords
- pvc
- reaction
- chlorine
- polymer
- copolymer
- 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
- 238000000034 method Methods 0.000 title claims description 31
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 21
- 229920000642 polymer Polymers 0.000 title claims description 21
- 229920001577 copolymer Polymers 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 17
- 229920000578 graft copolymer Polymers 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000000460 chlorine Substances 0.000 claims description 106
- 229910052801 chlorine Inorganic materials 0.000 claims description 99
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 98
- 230000005855 radiation Effects 0.000 claims description 13
- 229940057995 liquid paraffin Drugs 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 5
- 239000002250 absorbent Substances 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 117
- 239000004800 polyvinyl chloride Substances 0.000 description 117
- 238000006243 chemical reaction Methods 0.000 description 84
- 230000000052 comparative effect Effects 0.000 description 33
- 230000004044 response Effects 0.000 description 28
- 238000005660 chlorination reaction Methods 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 230000001105 regulatory effect Effects 0.000 description 16
- 230000035484 reaction time Effects 0.000 description 15
- 230000035515 penetration Effects 0.000 description 11
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- 230000036632 reaction speed Effects 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000498 cooling water Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004801 Chlorinated PVC Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 3
- 150000001804 chlorine Chemical class 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- -1 Ethylene, propylene Chemical group 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000002186 photoactivation Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- 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
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49055794A JPS5148795B2 (enExample) | 1974-05-18 | 1974-05-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2521843A1 DE2521843A1 (de) | 1975-11-27 |
| DE2521843B2 DE2521843B2 (de) | 1980-08-14 |
| DE2521843C3 true DE2521843C3 (de) | 1981-09-03 |
Family
ID=13008805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2521843A Expired DE2521843C3 (de) | 1974-05-18 | 1975-05-16 | Verfahren zur Herstellung eines chlorierten Polymerisates, Mischpolymerisates oder Pfropfpolymerisates aus Vinylchlorid |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4049517A (enExample) |
| JP (1) | JPS5148795B2 (enExample) |
| DE (1) | DE2521843C3 (enExample) |
| ES (1) | ES437745A1 (enExample) |
| IT (1) | IT1038192B (enExample) |
| NL (1) | NL159119B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0058171B1 (en) * | 1980-08-26 | 1985-05-29 | The B.F. GOODRICH Company | Process for chlorination of pvc in water without use of swelling agents |
| US4412898A (en) * | 1980-08-26 | 1983-11-01 | The B.F. Goodrich Company | Process for chlorination of PVC in water without use of swelling agents |
| US4350798A (en) * | 1981-01-26 | 1982-09-21 | The B. F. Goodrich Company | Chlorination of poly(vinyl chloride) in liquid chlorine, and chlorinated poly(vinyl chloride) composition |
| US4386189A (en) * | 1981-05-05 | 1983-05-31 | Delaware City Plastics Corporation | Process for the post-chlorination of vinyl chloride polymers |
| DE3324642A1 (de) * | 1983-07-08 | 1985-01-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur stabilisierung von photopolymerisierbaren mischungen |
| US4680343A (en) * | 1986-03-27 | 1987-07-14 | The B. F. Goodrich Company | Chlorinated poly(vinyl chloride) thermoplastic alloys |
| US4874823A (en) * | 1987-11-25 | 1989-10-17 | The B. F. Goodrich Company | Chlorinated polyvinyl chloride-vinyl acetate copolymers having good low and high temperature stability |
| US4983687A (en) * | 1988-05-23 | 1991-01-08 | The B. F. Goodrich Company | Crosslinked chlorinated polyvinyl chloride resin compositions |
| US5086122A (en) * | 1988-05-23 | 1992-02-04 | The B. F. Goodrich Company | Crosslinked chlorinated polyvinyl chloride resin compositions |
| DE69506048T2 (de) * | 1994-08-05 | 1999-07-15 | The B.F. Goodrich Co., Akron, Ohio | Material aus chloriertem Polyvinylchlorid mit verbesserter Zähigkeit und Stabilität, sowie niedrige Rauch- und Wärmeabgabe |
| US6187868B1 (en) | 1996-05-24 | 2001-02-13 | The B. F. Goodrich Company | Chlorinated polyvinyl chloride compound having excellent physical, chemical resistance and processing properties |
| US5821304A (en) * | 1996-05-24 | 1998-10-13 | The B. F. Goodrich Company | Chlorinated polyvinyl chloride compound having excellent physical, chemical resistance and processing properties |
| US5981663A (en) * | 1996-05-24 | 1999-11-09 | The B.F. Goodrich Company | Chlorinated polyvinyl chloride compound having excellent physical, chemical resistance and processing properties |
| JP3814733B2 (ja) * | 1997-07-29 | 2006-08-30 | 株式会社カネカ | 塩素化塩化ビニル系樹脂の製造方法 |
| US6025407A (en) * | 1997-10-30 | 2000-02-15 | Occidental Chemical Corporation | Photo-polymerization of vinyl chloride using metallocene catalysts |
| US6590041B1 (en) | 1998-01-14 | 2003-07-08 | Sekisui Chemical Co., Ltd. | Chlorinated vinyl chloride-based resin and molded articles |
| US6306945B1 (en) | 1998-09-10 | 2001-10-23 | Pmd Holdings Corporation | Halogen containing polymer compounds containing modified zeolite stabilizers |
| US6180549B1 (en) | 1998-09-10 | 2001-01-30 | The B. F. Goodrich Company | Modified zeolites and methods of making thereof |
| US6531526B1 (en) | 1998-09-10 | 2003-03-11 | Noveon Ip Holdings Corp. | Halogen containing polymer compounds containing modified zeolite stabilizers |
| JP4610877B2 (ja) * | 2003-10-22 | 2011-01-12 | 徳山積水工業株式会社 | 塩素化塩化ビニル系樹脂の製造方法 |
| US20050112311A1 (en) * | 2003-11-26 | 2005-05-26 | Dalal Girish T. | CPVC compositions having good impact strength and heat stability, and smooth surfaces |
| MXPA04011608A (es) | 2004-11-23 | 2006-05-25 | Servicios Condumex Sa | Formulaciones termoplasticas para fabricar tuberia y accesorios para fluidos de uso domestico e industrial y proceso. |
| JP4728701B2 (ja) * | 2005-05-25 | 2011-07-20 | 積水化学工業株式会社 | 塩素化塩化ビニル系樹脂の製造方法 |
| IN2014DN03471A (enExample) * | 2011-11-07 | 2015-06-05 | Kaneka Corp | |
| TWI580699B (zh) | 2012-05-01 | 2017-05-01 | 盧伯利索先進材料有限公司 | 具改良性質的自潤滑氯化聚氯乙烯樹脂、由其製成之物品及提供該物品之方法 |
| SG11201502965QA (en) | 2012-10-18 | 2015-05-28 | Reliance Ind Ltd | Halogenation of hydrocarbons |
| US9399687B2 (en) * | 2013-03-29 | 2016-07-26 | Kaneka Corportion | Method and apparatus for producing chlorinated vinyl chloride-based resin |
| US9944762B2 (en) * | 2013-05-02 | 2018-04-17 | Kaneka Corporation | Method for producing chlorinated polyvinyl chloride resin |
| US10035865B2 (en) * | 2014-07-22 | 2018-07-31 | Reliance Industries Limited | Preparation of chlorinated polyvinyl chloride |
| CA2971418C (en) | 2014-12-19 | 2024-01-09 | Lubrizol Advanced Materials, Inc. | Cpvc pipe having improved resistance to environmental stress cracking |
| KR102429997B1 (ko) | 2014-12-19 | 2022-08-04 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 환경적 응력 균열에 대한 개선된 저항성을 지니는 cpvc 파이프 피팅 |
| US10081687B2 (en) * | 2015-07-29 | 2018-09-25 | Reliance Industries Limited | Process for chlorination of a polymer |
| CN113646339B (zh) * | 2019-03-29 | 2022-12-23 | 积水化学工业株式会社 | 氯化聚氯乙烯系树脂 |
| WO2021065946A1 (ja) | 2019-09-30 | 2021-04-08 | 積水化学工業株式会社 | 成形用樹脂組成物及び成形体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB548486A (en) * | 1941-04-09 | 1942-10-13 | James Chapman | Chlorination of polyvinyl chloride |
| DE1210561B (de) * | 1963-10-15 | 1966-02-10 | Dynamit Nobel Ag | Verfahren zur Nachchlorierung von Homo- oder Mischpolymerisaten des Vinylchlorids |
| US3487129A (en) * | 1964-03-02 | 1969-12-30 | Monsanto Co | Novel chlorinated graft copolymer of polyvinyl chloride onto an ethylene polymer backbone |
| GB1131318A (en) * | 1965-11-20 | 1968-10-23 | Shinetsu Chem Ind Co | Heat stabilized polyvinyl chloride compositions |
| US3585117A (en) * | 1967-08-25 | 1971-06-15 | Dynamit Nobel Ag | Chlorination of homopolymers or copolymers of vinyl chloride and/or ethylene in suspension in the presence of dimethylsulfoxide |
| US3925337A (en) * | 1969-07-31 | 1975-12-09 | Air Prod & Chem | Post chlorinated vinyl chloride copolymers |
| US3700632A (en) * | 1971-06-08 | 1972-10-24 | Air Prod & Chem | Readily extruded chlorinated copolymers and process of preparing same |
-
1974
- 1974-05-18 JP JP49055794A patent/JPS5148795B2/ja not_active Expired
-
1975
- 1975-05-02 US US05/573,830 patent/US4049517A/en not_active Expired - Lifetime
- 1975-05-15 NL NL7505714.A patent/NL159119B/xx not_active IP Right Cessation
- 1975-05-16 ES ES437745A patent/ES437745A1/es not_active Expired
- 1975-05-16 DE DE2521843A patent/DE2521843C3/de not_active Expired
- 1975-05-16 IT IT23416/75A patent/IT1038192B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7505714A (nl) | 1975-11-20 |
| US4049517A (en) | 1977-09-20 |
| NL159119B (nl) | 1979-01-15 |
| DE2521843A1 (de) | 1975-11-27 |
| JPS5148795B2 (enExample) | 1976-12-22 |
| IT1038192B (it) | 1979-11-20 |
| DE2521843B2 (de) | 1980-08-14 |
| JPS50148495A (enExample) | 1975-11-28 |
| ES437745A1 (es) | 1977-02-16 |
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