NO126795B - - Google Patents
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- Publication number
- NO126795B NO126795B NO451469A NO451469A NO126795B NO 126795 B NO126795 B NO 126795B NO 451469 A NO451469 A NO 451469A NO 451469 A NO451469 A NO 451469A NO 126795 B NO126795 B NO 126795B
- Authority
- NO
- Norway
- Prior art keywords
- initiator
- polymerization
- peroxydicarbonate
- vinyl
- cetyl
- Prior art date
Links
- 239000003999 initiator Substances 0.000 claims description 16
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical group CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- -1 chemical compound dicetylperoxydicarbonate Chemical class 0.000 description 8
- 241000251468 Actinopterygii Species 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QVCQPIJMAAOGKX-UHFFFAOYSA-N (2,4,5-trimethylphenyl)thiourea Chemical compound CC1=CC(C)=C(NC(N)=S)C=C1C QVCQPIJMAAOGKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000385654 Gymnothorax tile Species 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Di-cetylperoksydikarbonat :for anvendelse som initiator for polymerisas jon av umettede forbindelser. Di-cetylperoxydicarbonate: for use as an initiator for the polymerization of unsaturated compounds.
Nærværende oppfinnelse vedrorer den kjemiske forbindelsen di-cetylperoksydikarbonat med formelen The present invention relates to the chemical compound dicetylperoxydicarbonate with the formula
Di-cetylperoksydikarbonat anvendes som initiator ved polymerisasjon av umettede forbindelser, f.eks. vinylklorid eller andre etenisk -umettede monomerer. Di-cetylperoxydicarbonate is used as an initiator in the polymerization of unsaturated compounds, e.g. vinyl chloride or other ethylenically unsaturated monomers.
Det er kjent at lignende forbindelser, f.eks. di-isopropyl-, di-n-butyl-, di-cykloheksyl- og di-tert.-butylcykloheksylperoksy-dikarbonat, er effektive initiatorer for polyraerisasjon av umettede forbindelser, slik som eten, metylmetakrylat, ■ vinylklorid, vinylidenklorid, vinylacetat, akrylamid, allylklorofor-miat og styren. It is known that similar compounds, e.g. di-isopropyl-, di-n-butyl-, di-cyclohexyl- and di-tert.-butylcyclohexylperoxy dicarbonate, are effective initiators for the polymerization of unsaturated compounds, such as ethylene, methyl methacrylate, ■ vinyl chloride, vinylidene chloride, vinyl acetate, acrylamide, allyl chloroformate and styrene.
Disse kjente initiatorer har dog den ulempe at stabiliteten er dårlig. Konsentrert di-isopropylperoksydikarbonat spalter seg med eksplosjonslignende hastighet ved romstemperatur og ovrige kjente peroksydikarbonater har i varierende grad dårlig lagrings-bestandighet. However, these known initiators have the disadvantage that the stability is poor. Concentrated di-isopropyl peroxydicarbonate decomposes with explosion-like speed at room temperature and other known peroxydicarbonates have varying degrees of poor storage stability.
Dette innebærer at betydelige ulemper og risiko oppstår ved industriell anvendelse av forbindelser av denne type. Således må frakten av initiatoren fra tilvirkeren til forbrukeren vanligvis skje ved hjelp av kjbletransport. Også lagringsplassen til forbrukeren må tilpasses disse forbindelsers folsomhet for varme. Spesielle forsiktighetsforanstaltninger må også treffes mot risiko for oppståelse av brann på lagerplassen. This means that significant disadvantages and risks arise from the industrial use of compounds of this type. Thus, the transport of the initiator from the manufacturer to the consumer must usually take place by means of cable transport. The storage space of the consumer must also be adapted to the sensitivity of these compounds to heat. Special precautions must also be taken against the risk of fire occurring in the warehouse.
Ifolge foreligende oppfinnelse har det overraskende vist seg at di-cetylperoksydikarbonat har en overlegen lagringsstabilitet overfor de hittil kjente peroksydikarbonatinitiatorer. Den nye forbindelse kan lagres i lange tider ved romtemperatur uten risiko for selvantennelse og uten at det aktive peroksydinn-holdet synker nevneverdig. En annen fordel ved den nye forbindelsen er at den foreligger i fast form og er fritt-rennende hvilket medforer at man meget lett og uten tap kan innfore initiatoren til polymerisasjonsreaktoren. En ytterligere fordel er at det spaltningsprodukt som dannes når initiatoren reagerer under dannelse av fri radikaler består av cetylalkohol, hvilken ikke er skadelig for mennesker og av denne grunn er initiatoren meget godt egnet for fremstilling av plast som senere skal bearbeides til forpakningsmateriale for næringsmidler. According to the present invention, it has surprisingly been shown that dicetyl peroxydicarbonate has a superior storage stability compared to the previously known peroxydicarbonate initiators. The new compound can be stored for long periods at room temperature without the risk of spontaneous combustion and without the active peroxide content dropping significantly. Another advantage of the new compound is that it is in solid form and is free-flowing, which means that the initiator can be introduced into the polymerization reactor very easily and without loss. A further advantage is that the cleavage product that is formed when the initiator reacts to form free radicals consists of cetyl alcohol, which is not harmful to humans and for this reason the initiator is very well suited for the production of plastic which will later be processed into packaging material for foodstuffs.
En annen meget påtagelig ulempe hos de hittil anvendte peroksydikarbonater, f.eks. di-isopropyl- og di-tert.-butylcykloheksyl-peroksydikarbonat, er deres tilbøyelighet til å danne såkalte fiskeoyne. Ved suspensjonspolymerisasjon av vinylklorid oppnås polyvinylkloridkorn .av størrelsesordenen 100 ja, med relativt pords xnnerstruktur. Når kjente peroksydikarbonater anvendes som initiatorer, oppnås en fraksjon polyvinylkloridkorn med kompakt struktur. Ved valsing av pdlyvinylkloridharpikset med myknings-midler, -kan mykningsmidlene ikke trenge inn i disse kompakte korn slik at de smelter, men de kommer til å bli liggende i den dannede plastfolie i form av små, hårde knotter som kalles fiskeoyne. Disse fiskeoyne gjor derfor harpikset helt uanvendelig for -visse formål, f.eks. flisisolering og tynne -folier. Di-cetylperoksydikarbonat har helt uventet vist seg å ha den egen-skapen at mengden av slike fiskeoyne blir -betydelig mindre enn ved anvendelse av f.eks. di-tert.-butylcykloheksylperoksydikarbo-nat. Innskrenkninger i anvendelsesområdet for harpiks som er fremstilt med foreliggende initiator unngås på denne måte. Another very noticeable disadvantage of the previously used peroxydicarbonates, e.g. di-isopropyl- and di-tert.-butylcyclohexyl-peroxydicarbonate, is their tendency to form so-called fish eyes. In the case of suspension polymerization of vinyl chloride, polyvinyl chloride grains of the order of 100 ja are obtained, with a relatively porous internal structure. When known peroxydicarbonates are used as initiators, a fraction of polyvinyl chloride grains with a compact structure is obtained. When rolling the pdlyvinyl chloride resin with plasticizers, the plasticizers cannot penetrate these compact grains so that they melt, but they will remain in the formed plastic film in the form of small, hard knobs called fish eyes. These fish eyes therefore make the resin completely unusable for -certain purposes, e.g. tile insulation and thin foils. Di-cetylperoxydicarbonate has quite unexpectedly been shown to have the property that the quantity of such fish eyes is -significantly less than when using e.g. di-tert-butylcyclohexylperoxydicarbonate. Restrictions in the area of application for resin produced with the present initiator are avoided in this way.
Di-cetylperoksydikarbonat kan anvendes for polymerisasjon av etenisk umettede monomerer, slik som vinylaromatiske forbindelser, .f.eks. styren, p-klorstyren, estere av alifatlske alfa-metylen-monokarbonsyrer, f . eks. metylakrylat, n-:butylakrylat, etylmet-akrylat, akrylsyrenitril, vinyl estere, f.eks., vinylacetat, vinylhalogenider, f.eks. vinylklorid, vinyletere, f.eks. vinyl-metyleter, vinylidenhalogenider-, f. eks., vinylidenklorid, alfa-etenisk umettede hydrokarboner., slik som eten-, propen samt umettede .polyestere. Som polymerisasjonstype egner suspensjonspolymerisasjon -eller massepolymerisasjon seg best. Spesielt ved fremstilling av polyvinylklorid kommer di-cetylperoksydikarbo--natets egenskaper som liurtig og effektiv initiator til sin rett. Diagram 1 viser polymerisasj-.onsforlopet for vinylklorid jned di-cetylperoksydikarbonat og den konvensjonelle dilauroylperoksyd. Med di-cetylperoksydikarbonat oppnås en halvering av polymerisa-sjonstiden til tross for at -de innforte initiatormengder di-cetylperoksydikarbonat : dilauroylperoksyd står i det molare forhold 1:V. Dicetylperoxydicarbonate can be used for the polymerization of ethylenically unsaturated monomers, such as vinyl aromatic compounds, e.g. styrene, p-chlorostyrene, esters of aliphatic alpha-methylene monocarboxylic acids, e.g. e.g. methyl acrylate, n-butyl acrylate, ethyl methacrylate, acrylic nitrile, vinyl esters, e.g., vinyl acetate, vinyl halides, e.g. vinyl chloride, vinyl ethers, e.g. vinyl methyl ether, vinylidene halides, e.g. vinylidene chloride, alpha-ethenically unsaturated hydrocarbons, such as ethylene, propene and unsaturated polyesters. As type of polymerization, suspension polymerization - or mass polymerization - is best suited. Especially in the production of polyvinyl chloride, di-cetyl peroxydicarbonate's properties as a liurtic and effective initiator come into their own. Diagram 1 shows the polymerization process for vinyl chloride with dicetyl peroxydicarbonate and the conventional dilauroyl peroxide. With di-cetyl peroxydicarbonate, a halving of the polymerization time is achieved despite the fact that the introduced initiator amounts of di-cetyl peroxydicarbonate : dilauroyl peroxide are in the molar ratio 1:V.
Ved fremstilling av foreliggende forbindelse innfores flytende cetylkloroformiat under omrdring til en alkalisk vandig oppldsning In the preparation of the present compound, liquid cetyl chloroformate is introduced with stirring to an alkaline aqueous solution
E^C^. Etter reaksjonstidens slutt består produktene av hvite, faste korn. E^C^. After the end of the reaction time, the products consist of white, solid grains.
De etterfølgende ikke begrensende eksempler viser fremstillings-måten og belyser også fordelene ved den her foreliggende oppfinnelse. The following non-limiting examples show the manufacturing method and also illustrate the advantages of the present invention.
EKSEMPEL 1 EXAMPLE 1
I en.1000 ml trehalset kolbe ble 500 ml destillert vann innfort, i hvilket 32 g fast NaOH ble opplost. Med et termostatregulert bad ble temperaturen regulert til 30°C, hvoretter ^0 g av 35 vektsk vannopplosning av hydrogenperoksyd ble innfort. Under intens omroring ble 150 g cetylkloroformiat innfort dråpevis under en tid av ca. 20 min. Etter 1,5 timers reaksjon ble det dannede faste produkt filtrert fra og etter omkrystallisasjon i karbontetraklorid inneholdt produktet 98 vekts-% peroksyd bereg-net som di-cetylperoksydikarbonat. 500 ml of distilled water was introduced into a 1000 ml three-necked flask, in which 32 g of solid NaOH were dissolved. With a thermostatically controlled bath, the temperature was regulated to 30°C, after which ^0 g of a 35-weight water solution of hydrogen peroxide was introduced. Under intense stirring, 150 g of cetyl chloroformate was introduced dropwise over a period of approx. 20 min. After 1.5 hours of reaction, the formed solid product was filtered off and after recrystallization in carbon tetrachloride the product contained 98% by weight of peroxide calculated as di-cetylperoxydicarbonate.
EKSEMPEL 2 EXAMPLE 2
Ved lagring av forskjellige perol^ydikarbonater ved h0°C i et termostatregulert bad oppnås folgende aktivitetsreduksjon som funksjon av tiden. When storing different perol^ydicarbonates at h0°C in a thermostatically controlled bath, the following activity reduction is achieved as a function of time.
EKSEMPEL 3 EXAMPLE 3
For å sammenligne fiskeoyneegenskapene mellom forskjellige initiatorer blandes polyvinylkloridharpiks, som er fremstilt på eksakt samme måte bortsett fra initiatortype, med myknings-middel ifolge folgende resept. In order to compare the fisheye properties between different initiators, polyvinyl chloride resin, which is produced in exactly the same way except for the type of initiator, is mixed with plasticizer according to the following recipe.
Blandingen ble valset ved 150°C i 10 minutter, hvoretter an-tall "fiskeoyne" pr. dm 2 ble bestemt. The mixture was rolled at 150°C for 10 minutes, after which the number of "fish eyes" per dm 2 was determined.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1545868A SE324767B (en) | 1968-11-14 | 1968-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126795B true NO126795B (en) | 1973-03-26 |
Family
ID=20300677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO451469A NO126795B (en) | 1968-11-14 | 1969-11-13 |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE741719A (en) |
| DE (1) | DE1957434B2 (en) |
| FR (1) | FR2023260A1 (en) |
| GB (1) | GB1267949A (en) |
| NL (1) | NL6917105A (en) |
| NO (1) | NO126795B (en) |
| SE (1) | SE324767B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2151142A5 (en) * | 1970-08-21 | 1973-04-13 | Pennwalt Corp | |
| DD106851A5 (en) * | 1972-05-24 | 1974-07-05 | ||
| US4394328A (en) * | 1978-06-30 | 1983-07-19 | Ppg Industries, Inc. | Production of peroxydicarbonates |
| CH656299A5 (en) * | 1982-04-15 | 1986-06-30 | Veronika Senn Walti | BEDDING. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370588A (en) * | 1942-10-22 | 1945-02-27 | Pittsburgh Plate Glass Co | Organic percarbonates |
| US2464062A (en) * | 1947-11-26 | 1949-03-08 | Pittsburgh Plate Glass Co | Polymerization with a peroxydicar-bonate catalyst |
| NL125860C (en) * | 1962-12-07 | |||
| GB978875A (en) * | 1963-03-29 | Ici Ltd |
-
1968
- 1968-11-14 SE SE1545868A patent/SE324767B/xx unknown
-
1969
- 1969-11-13 FR FR6938921A patent/FR2023260A1/fr active Pending
- 1969-11-13 NO NO451469A patent/NO126795B/no unknown
- 1969-11-13 NL NL6917105A patent/NL6917105A/xx unknown
- 1969-11-13 GB GB5561969A patent/GB1267949A/en not_active Expired
- 1969-11-14 DE DE19691957434 patent/DE1957434B2/en not_active Ceased
- 1969-11-14 BE BE741719D patent/BE741719A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1957434B2 (en) | 1978-05-18 |
| SE324767B (en) | 1970-06-15 |
| NL6917105A (en) | 1970-05-19 |
| GB1267949A (en) | 1972-03-22 |
| FR2023260A1 (en) | 1970-08-07 |
| BE741719A (en) | 1970-05-14 |
| DE1957434A1 (en) | 1970-06-11 |
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