CA1070705A - Bromine-containing phosphinic acid esters - Google Patents
Bromine-containing phosphinic acid estersInfo
- Publication number
- CA1070705A CA1070705A CA261,422A CA261422A CA1070705A CA 1070705 A CA1070705 A CA 1070705A CA 261422 A CA261422 A CA 261422A CA 1070705 A CA1070705 A CA 1070705A
- Authority
- CA
- Canada
- Prior art keywords
- bromine
- carbon atoms
- substituted
- flame
- phosphinic 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.)
- Expired
Links
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 33
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title claims abstract description 31
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title abstract description 15
- 229920003023 plastic Polymers 0.000 claims abstract description 30
- 239000004033 plastic Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920001577 copolymer Polymers 0.000 claims abstract description 7
- -1 phosphinic acid ester Chemical class 0.000 claims description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 239000004793 Polystyrene Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229920002223 polystyrene Polymers 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000465 moulding Methods 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 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 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001451 organic peroxides Chemical class 0.000 claims 1
- 230000002411 adverse Effects 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 235000010210 aluminium Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZSVPWTWQAVBLNH-UHFFFAOYSA-N ClP(=O)CC=C Chemical compound ClP(=O)CC=C ZSVPWTWQAVBLNH-UHFFFAOYSA-N 0.000 description 2
- 244000228957 Ferula foetida Species 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 150000005526 organic bromine compounds Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- ZFTYTEXTMQFIEK-UHFFFAOYSA-N prop-2-enylphosphinic acid Chemical compound OP(=O)CC=C ZFTYTEXTMQFIEK-UHFFFAOYSA-N 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- HGRZLIGHKHRTRE-UHFFFAOYSA-N 1,2,3,4-tetrabromobutane Chemical compound BrCC(Br)C(Br)CBr HGRZLIGHKHRTRE-UHFFFAOYSA-N 0.000 description 1
- WJWCMZVNMUOIIY-UHFFFAOYSA-N 1,2-dibromoethyl(methyl)phosphinic acid Chemical compound CP(O)(=O)C(Br)CBr WJWCMZVNMUOIIY-UHFFFAOYSA-N 0.000 description 1
- KKGVBGGAVZGMKA-UHFFFAOYSA-N 1-bromo-2-[2-bromoethoxy(2-bromoethyl)phosphoryl]oxyethane Chemical compound BrCCOP(=O)(CCBr)OCCBr KKGVBGGAVZGMKA-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 description 1
- VDIFMFWKPVNKBM-UHFFFAOYSA-N CC=CP(=O)Cl Chemical compound CC=CP(=O)Cl VDIFMFWKPVNKBM-UHFFFAOYSA-N 0.000 description 1
- YFQFTFQTMXBZCT-UHFFFAOYSA-N CP(=O)Cl Chemical compound CP(=O)Cl YFQFTFQTMXBZCT-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000998897 Homo sapiens Serine protease HTRA3 Proteins 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 101100328463 Mus musculus Cmya5 gene Proteins 0.000 description 1
- KLHARAFICHBQOE-UHFFFAOYSA-N OP(=O)C(Br)CBr Chemical compound OP(=O)C(Br)CBr KLHARAFICHBQOE-UHFFFAOYSA-N 0.000 description 1
- 102100033197 Serine protease HTRA3 Human genes 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000613130 Tima Species 0.000 description 1
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752542009 DE2542009A1 (de) | 1975-09-20 | 1975-09-20 | Bromhaltige phosphinsaeureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070705A true CA1070705A (en) | 1980-01-29 |
Family
ID=5956992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,422A Expired CA1070705A (en) | 1975-09-20 | 1976-09-17 | Bromine-containing phosphinic acid esters |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4111900A (enExample) |
| JP (1) | JPS5239630A (enExample) |
| AT (1) | AT349215B (enExample) |
| AU (1) | AU508826B2 (enExample) |
| BE (1) | BE846380A (enExample) |
| CA (1) | CA1070705A (enExample) |
| DE (1) | DE2542009A1 (enExample) |
| DK (1) | DK420676A (enExample) |
| FR (1) | FR2324642A1 (enExample) |
| GB (1) | GB1566296A (enExample) |
| IT (1) | IT1068302B (enExample) |
| LU (1) | LU75830A1 (enExample) |
| NL (1) | NL7610265A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4321187A (en) * | 1980-07-03 | 1982-03-23 | American Cyanamid Company | Phosphinic acid flame retardants for polyphenylene ether resins |
| US4539347A (en) * | 1984-09-20 | 1985-09-03 | Celanese Corporation | Novolac based epoxy resin curing agents for use in aqueous systems |
| DE3925792A1 (de) * | 1989-08-04 | 1991-02-07 | Bayer Ag | Flammgeschuetzte, nicht tropfende polyamidformmassen |
| JP6618049B2 (ja) * | 2013-08-22 | 2019-12-11 | 株式会社Adeka | 含リン化合物及びそれを含有する硬化性エポキシ樹脂組成物 |
| CN108912174B (zh) * | 2018-06-22 | 2021-02-09 | 四川东材科技集团股份有限公司 | 一种阻燃双烷环型多元醇树脂及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495419B2 (de) * | 1962-05-08 | 1970-07-16 | The Dow Chemical Co., Midland, Mich. (V.St.A.) | Verfahren zur Herstellung von schwerentflammbaren, thermoplastischen alkenylaromatisehen Polymeren |
| US3324205A (en) * | 1963-03-05 | 1967-06-06 | Celanese Corp | Halogenated phosphates and phosphonates and method of preparation |
| SU362023A1 (ru) * | 1971-03-24 | 1972-12-13 | Ордена Трудового Красного Знамени институт органической , физической химии А. Е. Арбузова | СПОСОБ ПОЛУЧЕНИЯ АЛКИЛОВЫХ ЭФИРОВ р-БРОМЭТИЛАЛКИЛФОСФИНОВЫХ КИСЛОТECF-ооюзнАЯ 1; nATERTviO-T?KWH4?"u4f; |
| JPS4891019A (enExample) * | 1972-03-08 | 1973-11-27 | ||
| DE2402268A1 (de) * | 1974-01-18 | 1975-08-14 | Hoechst Ag | Verfahren zur herstellung von schwer entflammbaren kunststoffen |
-
1975
- 1975-09-20 DE DE19752542009 patent/DE2542009A1/de not_active Withdrawn
-
1976
- 1976-09-15 NL NL7610265A patent/NL7610265A/xx unknown
- 1976-09-17 JP JP51110900A patent/JPS5239630A/ja active Pending
- 1976-09-17 AT AT690376A patent/AT349215B/de not_active IP Right Cessation
- 1976-09-17 IT IT27371/76A patent/IT1068302B/it active
- 1976-09-17 AU AU17863/76A patent/AU508826B2/en not_active Expired
- 1976-09-17 US US05/724,252 patent/US4111900A/en not_active Expired - Lifetime
- 1976-09-17 CA CA261,422A patent/CA1070705A/en not_active Expired
- 1976-09-17 LU LU75830A patent/LU75830A1/xx unknown
- 1976-09-17 DK DK420676A patent/DK420676A/da unknown
- 1976-09-20 FR FR7628139A patent/FR2324642A1/fr not_active Withdrawn
- 1976-09-20 BE BE170773A patent/BE846380A/xx unknown
- 1976-09-20 GB GB38954/76A patent/GB1566296A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1566296A (en) | 1980-04-30 |
| AU1786376A (en) | 1978-03-23 |
| BE846380A (fr) | 1977-03-21 |
| US4111900A (en) | 1978-09-05 |
| IT1068302B (it) | 1985-03-21 |
| AU508826B2 (en) | 1980-04-03 |
| DK420676A (da) | 1977-03-21 |
| AT349215B (de) | 1979-03-26 |
| JPS5239630A (en) | 1977-03-28 |
| ATA690376A (de) | 1978-08-15 |
| NL7610265A (nl) | 1977-03-22 |
| FR2324642A1 (fr) | 1977-04-15 |
| LU75830A1 (enExample) | 1977-05-13 |
| DE2542009A1 (de) | 1977-03-24 |
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