NO121259B - - Google Patents
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- NO121259B NO121259B NO518468A NO518468A NO121259B NO 121259 B NO121259 B NO 121259B NO 518468 A NO518468 A NO 518468A NO 518468 A NO518468 A NO 518468A NO 121259 B NO121259 B NO 121259B
- Authority
- NO
- Norway
- Prior art keywords
- iodine
- polyvinylpyrrolidone
- product
- parts
- addition
- Prior art date
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- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 22
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 22
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 21
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 11
- OIVUHPTVQVCONM-UHFFFAOYSA-N 6-bromo-4-methyl-1h-indazole Chemical compound CC1=CC(Br)=CC2=C1C=NN2 OIVUHPTVQVCONM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000645 desinfectant Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000004061 bleaching Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 11
- 239000011630 iodine Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- -1 silver halide Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- DSPXASHHKFVPCL-UHFFFAOYSA-N 1-isocyanocyclohexene Chemical compound [C-]#[N+]C1=CCCCC1 DSPXASHHKFVPCL-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B35/00—Vessels or similar floating structures specially adapted for specific purposes and not otherwise provided for
- B63B35/28—Barges or lighters
- B63B35/30—Barges or lighters self-discharging
- B63B35/303—Barges or lighters self-discharging discharging by suction, pressing or washing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B27/00—Arrangement of ship-based loading or unloading equipment for cargo or passengers
- B63B27/24—Arrangement of ship-based loading or unloading equipment for cargo or passengers of pipe-lines
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- Ocean & Marine Engineering (AREA)
- Transportation (AREA)
- Filling Or Discharging Of Gas Storage Vessels (AREA)
- Structures Of Non-Positive Displacement Pumps (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Fremgangsmåte til fremstilling av stabile interhalogen-addisjonsprodukter av polyvinylpyrrolidon. Process for the production of stable interhalogen addition products of polyvinylpyrrolidone.
Den foreliggende oppfinnelse angår The present invention concerns
fremstilling av interhalogen-addisjonsprodukter av polymert l-vinyl-2-pyrrolidon preparation of interhalogen addition products of polymeric 1-vinyl-2-pyrrolidone
(som heretter bare kalles polyvinylpyrrolidon). (hereinafter simply called polyvinylpyrrolidone).
Kombinasjonen av polyvinylpyrrolidon The combination of polyvinylpyrrolidone
med jod har resultert i dannelse av et with iodine has resulted in the formation of a
stabilt addisjonsprodukt. I norsk patent stable addition product. In Norwegian patent
nr. 84.024 og 87.534 er det beskrevet Nos. 84,024 and 87,534 are described
et nytt produkt av polyvinylpyrrolidon og a new product of polyvinylpyrrolidone and
jod som har vist seg å ha betydelig verdi iodine which has been shown to be of considerable value
for mange anvendelser, og i hvilket man for many applications, and in which one
utnytter den bakteriside aktivitet av joden, og ved hvilket man dessuten praktisk utilizes the bactericidal activity of the iodine, and by which one also practical
talt unngår de irriterende, sensiterende og spoken, they avoid irritating, sensitizing and
toksiske egenskaper hos jod. toxic properties of iodine.
Som angitt i den nevnte oppfinnelse As stated in the said invention
blir det nye jod-polyvinylpyrrolidon-produkt fremstill ved å tilsette en oppløsning the new iodine-polyvinylpyrrolidone product is prepared by adding a soln
av jod eller en jodtinktur til en vandig opp-løsning av polyvinylpyrrolidon. Slike pro-duker kan også fremstilles, som beskrevet of iodine or an iodine tincture to an aqueous solution of polyvinylpyrrolidone. Such products can also be produced, as described
i U. S. patent nr. 2.706.701 ved at man in U. S. patent no. 2,706,701 in that man
grundig blander tørr elementær jod med thoroughly mix dry elemental iodine with
et tørt pulverformig polyvinylpyrrolidon. a dry powdered polyvinylpyrrolidone.
Joden og den pulveriserte polymere blan-des inntil man får et homogent pulver; The iodine and the powdered polymer are mixed until a homogeneous powder is obtained;
blandingen skjer ved å male stoffene sammen i en morter med en pistill eller i en the mixture is made by grinding the substances together in a mortar with a pestle or in a
passende mekanisk blander, f. eks. en kule-mølle som er laget av materialer som ikke suitable mechanical mixer, e.g. a ball mill that is made of materials that do not
angripes av jod. Deretter blir den homo-gene blanding opphetet ved en temperatur attacked by iodine. The homogeneous mixture is then heated at a temperature
av 90—100° C i en tid av 22—64 timer. of 90-100° C for a period of 22-64 hours.
Når man ved å anvende den foran When one by applying it in front
nevnte fremgangsmåte forsøkte å frem-stille et bromaddisjonsprodukt, fikk man said method tried to produce a bromine addition product, it was obtained
et produkt som hadde mindre stabilitet. a product that had less stability.
Fremstillingen av et klor addisjonsprodukt i stabil form kunne ikke utføres. Den kjemiske industri, spesielt blekeindustrien og desinfeksjonsområder har imidlertid behov for et stabilt polyvinylpyrrolidonkompleks som inneholder tilgjengelig klor eller brom sammen med jod. The production of a chlorine addition product in stable form could not be carried out. However, the chemical industry, especially the bleaching industry and disinfection areas, need a stable polyvinylpyrrolidone complex containing available chlorine or bromine together with iodine.
Det å skaffe et interhalogent addisjonsprodukt, et polyvinylpyrrolidon som inneholder enten klor eller brom sammen med jod og som har nye industrielle anvendelser, utgjør hovedformålet for den foreliggende oppfinnelse. The main object of the present invention is to provide an interhalogen addition product, a polyvinylpyrrolidone containing either chlorine or bromine together with iodine and which has new industrial applications.
Andre formål og fordeler vil fremgå av Other purposes and benefits will be apparent from
den følgende beskrivelse. the following description.
Oppfinnerne har funnet at verdifulle produkter av polyvinylpyrrolidon, som inneholder enten klor eller brom sammen med jod og som er stabile, lett kan fremstilles ved å blande jodmonoklorid eller jodmonobromid med polyvinylpyrrolidon inntil det fåes en homogen blanding, hvoretter man oppheter blandingen i en lukket beholder i fra 1 1/2—8 timer ved en temperaur som ikke overstiger 95° C. De således erholdte produkter er ikke bare nyttige som bleke- og desinfiseringsmidler, men også som antiseptika og til å fjerne forurensninger av sennepsgass. Jodmono-kloridaddisjonsproduktet er usedvanlig godt egnet som blekemiddel i tekstilindu-strien og til å fjerne forurensninger av sennepsgass. I det siste tilfelle blir jodmo-nokloridaddisjonsforbindelsen dusjet ut i form av en vandig oppløsning som inneholder 10—25 vektdeler av jodmonoklor-addisjonsproduktet, ut i atmosfæren som er forurenset med sennepsgass. Produktet ér åv særlig verdi i kjemiske laboratorier og anlegg hvor sådan gass anvendes som et mellomprodukt eller som deltager i kjemiske reaksjoner. Hvis det opptrer en lek-kasje fra et kjemisk reaksjonssystem eller fra en sylinder som inneholder gassen, ned-settes den pinefulle blæredannende virk-ning som gassen har, og i enkelte tilfelle kan den fjernes fullstendig ved å dusje ikke bare vedkommende individ, men også hele det område som er forurenset med gassen. Jodmonoklorid- og jodmonobromid-addisjonsforbindelsene av polyvinylpyrrolidon er særlig egnet som desinfeksjons-midler, ikke bare i låver og fjøs og rundt gårdsbruk, men også i hjemmene og i hos-pitaler. The inventors have found that valuable products of polyvinylpyrrolidone, which contain either chlorine or bromine together with iodine and are stable, can be easily prepared by mixing iodine monochloride or iodine monobromide with polyvinylpyrrolidone until a homogeneous mixture is obtained, after which the mixture is heated in a closed container in from 1 1/2—8 hours at a temperature not exceeding 95° C. The products thus obtained are not only useful as bleaching and disinfecting agents, but also as antiseptics and for removing impurities of mustard gas. The iodine monochloride addition product is exceptionally well suited as a bleaching agent in the textile industry and for removing mustard gas contaminants. In the latter case, the iodine monochloride addition compound is showered out in the form of an aqueous solution containing 10-25 parts by weight of the iodine monochloride addition product into the atmosphere which is contaminated with mustard gas. The product is of particular value in chemical laboratories and plants where such gas is used as an intermediate product or as a participant in chemical reactions. If a leak occurs from a chemical reaction system or from a cylinder containing the gas, the painful blister-forming effect of the gas is reduced, and in some cases it can be completely removed by showering not only the individual concerned, but also the entire area contaminated with the gas. The iodine monochloride and iodine monobromide addition compounds of polyvinylpyrrolidone are particularly suitable as disinfectants, not only in barns and barns and around farms, but also in homes and hospitals.
Det polyvinylpyrrolidon som anvendes i henhold til den foreliggende oppfinnelse, fremstilles ved den fremgangsmåte som er beskrevet i U. S. patenter nr. 2.265.450 og 2.335.454. Alt etter polymerisasjonsgraden har de polymere molekylvekter som ligger mellom 500—200.000. Viskositetsmålinger anvendes som en indikasjon på den midle-re molekylarvekt av den polymere (polyvinylpyrrolidon) som er karakterisert ved en kjede av kullstoff atomer som er forbun-det med hverandre gjennom kjedens kvel-stof f atomer: The polyvinylpyrrolidone used in accordance with the present invention is produced by the method described in U.S. patents no. 2,265,450 and 2,335,454. Depending on the degree of polymerisation, the polymers have molecular weights between 500 and 200,000. Viscosity measurements are used as an indication of the average molecular weight of the polymer (polyvinylpyrrolidone) which is characterized by a chain of carbon atoms which are connected to each other through the chain's nitrogen atoms:
Viskositetskoeffisienten K, som er fullt beskrevet i Modern Plastics, 23, No. 3, 1957— 61, 212, 214, 216, 218 (1945), beregnes som følger: The viscosity coefficient K, which is fully described in Modern Plastics, 23, No. 3, 1957— 61, 212, 214, 216, 218 (1945), is calculated as follows:
hvor C er konsentrasjonen i gram pr. 100 ml av polymer oppløsning, og r\ rel. er for-holdet mellom viskositeten av oppløsningen og det rene oppløsningsmiddels viskositet. K-verdiene angis som 1000 ganger den be-regnede viskositetskoeffisient, for. å unngå anvendelsen av desimaler. For den foreliggende oppfinnelses formål benyttes de polymere som har en K-verdi på 10—100, fortrinnsvis 30—100, på grunn av disses viskositet ved lavere konsentrasjoner. Antallet av gjenkommende monomerenheter i den alminnelige formel •betegnet med n, som angir polymerisasjonsgraden, svarer til en kjede med 192— 980 monomerenheter. I praksis anvendes det alltid en blanding av polymere som hver inneholder et forskjellig antall (n) av monomerenheter. where C is the concentration in grams per 100 ml of polymer solution, and r\ rel. is the ratio between the viscosity of the solution and the viscosity of the pure solvent. The K values are given as 1000 times the calculated viscosity coefficient, for. to avoid the use of decimals. For the purposes of the present invention, the polymers are used which have a K-value of 10-100, preferably 30-100, due to their viscosity at lower concentrations. The number of recurring monomer units in the general formula denoted by n, which indicates the degree of polymerization, corresponds to a chain of 192-980 monomer units. In practice, a mixture of polymers is always used, each of which contains a different number (n) of monomer units.
Jodmonokloridet kan anvendes som sådant eller fremstillet av jodtriklorid. Det sistnevnte fremstilles ved å selte jod til fly-tende klor ved 95° C. Det gule produkt fikk hydrolysere til det brune jodmonoklorid, som kan anvendes i blanding med polyvinylpyrrolidon. Jodmonobromidet kan kjøpes som sådant eller fremstilles på en-kel måte ved direkte kombinering av ele-mentene ved kjente midler. The iodine monochloride can be used as such or prepared from iodine trichloride. The latter is produced by salting iodine to liquid chlorine at 95° C. The yellow product was allowed to hydrolyse to the brown iodine monochloride, which can be used in mixture with polyvinylpyrrolidone. The iodine monobromide can be purchased as such or prepared in a simple way by directly combining the elements by known means.
De følgende eksempler tjener til å il-lustrere hvorledes de forskjellige interha-logenaddisjonsprodukter av polyvinylpyrrolidon kan fremstilles i henhold til den foreliggende oppfinnelse. Imidlertid er dis-se eksempler bare rent illustrerende, og skal ikke begrense oppfinnelsens <p>g be-skyttelsens område. Alle deler er angitt som vektdeler med mindre noe annet er spesielt sagt. The following examples serve to illustrate how the various interhalogen addition products of polyvinylpyrrolidone can be prepared according to the present invention. However, these examples are purely illustrative, and shall not limit the scope of the invention and protection. All parts are given by weight unless otherwise specifically stated.
Eksempel 1. Example 1.
Til 40 deler polyvinylpyrrolidon som har en K-verdi på 30, ble det blandet 10 deler jodmonoklorid ved romtemperatur i en gassbeholder inntil det var dannet et homogent oransje produkt. Produktet ble deretter opphetet i en lukket glassbeholder ved 90° C i 2 1/2 time. Ved analyse viste det følgende halogeninnhold: To 40 parts of polyvinylpyrrolidone having a K value of 30, 10 parts of iodine monochloride were mixed at room temperature in a gas container until a homogeneous orange product was formed. The product was then heated in a closed glass container at 90° C. for 2 1/2 hours. On analysis it showed the following halogen content:
25 deler av jodmonokloridaddisjonspro-duktet av polyvinylpyrrolidon fremstilt på ovennevnte måte, ble satt til vanlig spring-vann så man fikk 100 deler av en oppløs-ning., Denne oppløsning bleket øyeblikke-lig gulaktig musselin når den kom i berø-ring med denne. Etter skylling med vann og tørking forble musselinen hvit. Hvis den samme oppløsning blir dusjet inn i et kam-mer som har ca. 1 ms volum og inneholder 150 deler sennepsgass pr. million deler luft, blir kammeret fullstendig befridd for giftig gass i løpet av ett minutt. 25 parts of the iodine monochloride addition product of polyvinylpyrrolidone prepared in the above manner was added to ordinary tap water to give 100 parts of a solution. This solution immediately bleached yellowish muslin when it came into contact with it. After rinsing with water and drying, the muslin remained white. If the same solution is showered into a chamber that has approx. 1 ms volume and contains 150 parts of mustard gas per million parts of air, the chamber is completely freed of toxic gas within one minute.
Eksempel 2. Example 2.
Til 20 deler polyvinylpyrrolidon som har en K-verdi på 30, ble sat 3,4 deler jodmonobromid fulgt av tørr blanding i en glassbeholder inntil det var dannet et homogent produkt. Produktet ble deretter opphetet ved 90° C i seks timer. Kjemisk analyse av halogeninnholdet og fenolkoef-fisienten viste følgende resultater: To 20 parts of polyvinylpyrrolidone having a K value of 30 was added 3.4 parts of iodine monobromide followed by dry mixing in a glass container until a homogeneous product was formed. The product was then heated at 90°C for six hours. Chemical analysis of the halogen content and the phenol coefficient showed the following results:
For anvendelse som desinfeksjonsmiddel og desodoriseringsmiddel blir 10—30 vektdeler av produktet fra eksempel 2 opp-løst i nok vann til at man får 100 deler vandig oppløsning. 1 del av denne oppløs-ning satt til 100 deler vann er tilstrekkelig til å desinfisere og desodorisere illeluk-tende arealer. For use as a disinfectant and deodorizer, 10-30 parts by weight of the product from example 2 are dissolved in enough water to obtain 100 parts of an aqueous solution. 1 part of this solution added to 100 parts of water is sufficient to disinfect and deodorize foul-smelling areas.
Foruten til de foran nevnte anvendel- In addition to the aforementioned applications
ser, er interhalogenaddisjonsproduktene av polyvinylpyrrolidon av særlig verdi ved fremstilling av sensitiverte gelalinsølvha-logenidemulsjoner. Ved en sådan anvendelse blir 15—25 vektdeler av enten jodmonoklorid eller jodmonobromidaddisjons-forbindelsen dispergert i en tilstrekkelig mengde av den vanlige gelatindispersjon til at man får ialt 100 vektdeler emulsjon. Til den resulterende emulsjon settes det en tilstrekkelig mengde sølvnitrat til å forene seg med det tilgjengelige halogen i dan-nelsen av blandede sølvhalogenider. Emul-sjonen vaskes flere ganger med vann på den vanlige måte, sensitiveres med et sen-sitiverende fargestoff, modnes og anbrin-ges deretter som belegg på et passende underlag av celluloseacetat. see, the interhalogen addition products of polyvinylpyrrolidone are of particular value in the preparation of sensitized gelalin silver halide emulsions. In such an application, 15-25 parts by weight of either iodine monochloride or the iodine monobromide addition compound are dispersed in a sufficient amount of the usual gelatin dispersion to obtain a total of 100 parts by weight of emulsion. To the resulting emulsion is added a sufficient amount of silver nitrate to combine with the available halogen in the formation of mixed silver halides. The emulsion is washed several times with water in the usual way, sensitized with a sensitizing dye, matured and then applied as a coating to a suitable substrate of cellulose acetate.
Claims (1)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO518468A NO121259B (en) | 1968-12-24 | 1968-12-24 | |
GB1905269A GB1218880A (en) | 1968-12-24 | 1969-04-14 | Improvements in or relating to ships |
DE19691951404 DE1951404A1 (en) | 1968-12-24 | 1969-10-11 | Device on ships |
SE1526269A SE365769B (en) | 1968-12-24 | 1969-11-06 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO518468A NO121259B (en) | 1968-12-24 | 1968-12-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO121259B true NO121259B (en) | 1971-02-01 |
Family
ID=19880823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO518468A NO121259B (en) | 1968-12-24 | 1968-12-24 |
Country Status (4)
Country | Link |
---|---|
DE (1) | DE1951404A1 (en) |
GB (1) | GB1218880A (en) |
NO (1) | NO121259B (en) |
SE (1) | SE365769B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3738305A (en) * | 1971-01-26 | 1973-06-12 | Algoship Int | Oil tank heating apparatus |
GB2143183B (en) * | 1983-07-11 | 1987-04-29 | Hitachi Shipbuilding Eng Co | Double hulled vessel |
DE4412666C1 (en) * | 1994-04-13 | 1995-07-06 | Muesing Anton Gmbh Co Kg | Hold of hopper dredger ship for handling cargo |
-
1968
- 1968-12-24 NO NO518468A patent/NO121259B/no unknown
-
1969
- 1969-04-14 GB GB1905269A patent/GB1218880A/en not_active Expired
- 1969-10-11 DE DE19691951404 patent/DE1951404A1/en active Pending
- 1969-11-06 SE SE1526269A patent/SE365769B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
SE365769B (en) | 1974-04-01 |
DE1951404A1 (en) | 1970-07-02 |
GB1218880A (en) | 1971-01-13 |
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