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  1. #1
    Ian Grant's Avatar
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    Modern Rodinal Substitutes Part II

    Apologies for having to start a new thread but I can't read or even access the first to reply to posts.

    So with a bit of telepathy

    Quote Originally Posted by Kirk Keyes View Post
    Well, there's a problem there, as it's really hard to measure pH accurately when it gets much above 12.5 or so. You have to start getting special electrodes and the like.

    But for MSDS work, it doesn't have to be too precise.
    __________________
    Kirk

    A point that's being missed is that A&O give a figure of 2.7% Potassium Hydroxide not 3% in older Agfa MSDS.

    The pH is around 14 sure, but the actual requirement is the pH of the working dilute solution rather than the concentrate which is given elsewhere as pH 11.55, which I commented on in the first post of the thread.

    Way back Ron (PE) mentioned adjustments to Rodinal before bottling, the question we need to ask is are they adjusting on the basis of the concentrate, or also doing some tests on a dilute sample, as this will be a far more accurate indicator.

    Can someone please post a link to this continuation on the original post.

    Ian

  2. #281
    Ian Grant's Avatar
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    Look at USP 4095982. Fuji are using Sodium benzenesulfonate (Benzenesulfonic acid sodium salt) as an anti-oxidant. As it's use as an anti-oxidant is referenced in a number of other Photographic Patents I think we can be 100% certain that Pavel's got it right. It's used as an anti-oxidant in many other field too and made & sold in bulk quantities.

    I have another Polish source calling it "Benzosulifinian sodow" in Orwo RO9. But I suspect this is a Typo or translation in a publication as the sulphonic group translates as Sulfonian as Ron says.

    Ian

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    Photo Engineer's Avatar
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    Maybe David Goldfarb could step in here and give us a definitive reading on the Polish translation.

    PE

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    Quote Originally Posted by Ian Grant View Post
    Look at USP 4095982. Fuji are using Sodium benzenesulfonate (Benzenesulfonic acid sodium salt) as an anti-oxidant.
    Ian, are you quite sure about that?

    That sulfonate is a soap as well as a biocide and is mentioned as a coating aid, not as an antioxidant, (as far as I was willing to read anyway)...

    Did they tuck that info somewhere I did not look,
    or did you give us the wrong number?

    In anycase, I think the comment that it acts to "decrease" the diffusion of oxygen is much more interesting however. I gather this can be done by forming at least 2 phases of different oxygen solubilty... from my lack of knoweledge of how soaps work, I can only say that it sounds like it might at least be plausable.

    Ray

  5. #284
    Ian Grant's Avatar
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    Quote Originally Posted by Photo Engineer View Post
    Maybe David Goldfarb could step in here and give us a definitive reading on the Polish translation.
    PE
    Not needed as it's almost certainly an error probably of translation into Polish originally, I've now confirmed the Agfa link to Sodium Benzenesulfonate use in developers in the 1930, which fits the time frame for these additives in Rodinal.

    About 7 or 8 years ago I was given a list of Eastern European formulae in Polish but with translations of every chemical name except "Benzosulifinian sodow" which was why I'd put the formula to one side.

    However it turns out that Kodak reference Benezesulfonates specifically in USP 2,618,558 and the cited references link Sodium benzenesulfonate directly to a 1930's Agfa Ansco Patent USP 2,000,353 (German 506,838), others cite different German Patents. Some of the other German pre-WWII Patents may be more specific and useful.

    Quote Originally Posted by Ray Rogers View Post
    Ian, are you quite sure about that?

    That sulfonate is a soap as well as a biocide and is mentioned as a coating aid, not as an antioxidant, (as far as I was willing to read anyway)...

    Did they tuck that info somewhere I did not look, or did you give us the wrong number?

    Ray
    It's in a few Fuji Patents, perhaps this one is better USP 2618558 where Sodium Benzenesulfonate is specifically mentioned as an anti-foggant, see attachment.

    What's important is that the Patents show Agfa, Kodak and Fuji using Benzenesulfonates as anti-foggants, Agfa as far back as the 1930's.

    Ian
    Attached Thumbnails Attached Thumbnails skeptic.jpg  

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    Ian, are you quite sure about that?

    That sulfonate is a soap as well as a biocide and is mentioned as a coating aid, not as an antioxidant, (as far as I was willing to read anyway)...

    Did they tuck that info somewhere I did not look, or did you give us the wrong number?

    Ray


    Quote Originally Posted by Ian Grant View Post
    It's in a few Fuji Patents, perhaps this one is better USP 2618558 where Sodium Benzenesulfonate is specifically mentioned as an anti-foggant, see attachment.

    What's important is that the Patents show Agfa, Kodak and Fuji using Benzenesulfonates as anti-foggants, Agfa as far back as the 1930's.

    Ian
    Ian,

    Please slow down and take another lookat those patents.

    This is twice you have stated a certain patent claims sulphonates as antioxidants yet in both cases that does not seem to be the case.

    Here, you also have provided an attachment that says Benzene sulfonate is an anti-oxidant, and by sentence structure, you imply it is from the named patent, but that does not seem to be the case either.

    What is the correct source of the attachment?
    (It actually looks familiar to me...)

    I have been aware of the use of both sulfonates and sulfinates and I am not inspired by any of these examples; they are known technologies.

    I am a little worried about your claim that those patents say something that they appearently do not. (I SURE hope I did not overlook it -if I did I do apologize, but...) Perhaps we all might fare better if we slow down a bit.

    For me at least,
    it would be better to get solid information at a snails pace,
    than flimsy info faster than a speeding bullet.

    I lost a few hours today as a result of those speeding bullets.

    Ray
    Last edited by Ray Rogers; 10-05-2009 at 04:49 AM. Click to view previous post history.

  7. #286
    Ian Grant's Avatar
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    You need to read things , but I could have given all the Patent No's use the search feature in Adobe Acrobat: Try another US 3765892 this is the one I cut & pasted from. I'm skipping between Patents rather fast looking at it's uses, and the Fuji Patents are interlinked through citations etc.



    2nd line states . . . . . . sodium benzenene-sulfonate, ascorbic acid, diethylhydroxylamine, etc are used as antioxidants. Page 3 of the Patent bottom of Column 3.

    The fact that Fuji refer to it in at least 4 Patents, and that many other companies/patents refer to it as an antioxidant is rather conclusive that it can be used as such.
    :
    Quote Originally Posted by Kirk Keyes View Post
    Sulfonic acids, as a class, are often used as detergents/wetting agents. Benzene sulfonic acid is probably not used for that much as it's rather reactive, I thought. But longer chained sulfonic acids are, as you can have an alkane or aromatic on an alkane chain and the sulfonic acid group on the other end, and that's good for detergents.
    Sodium Benzenesulfonate may well fall somewhere between what Mason (& Levenson) cal anti-oxidants and wetting agents - which include sodium alkyl sulphonates.

    I was more interested in finding a link to it's use by Agfa, I've save some of the other Patents for later reading but didn't think they were of that much interest.

    Ian

  8. #287
    Photo Engineer's Avatar
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    Well, with the help of a friend, and after an exhaustive search of my Kodak literature and his German literature, we find only references to Benzenesulfinic acid as an antioxidant and generic sulfonates as wetting agents.

    This is quite perplexing to find the sulfinic acids in both places as antioxidants and the sulfonic acids as wetting agents, and neither agreeing with what has gone on above. The above posts indicate that the sulfonic acids have both functions.

    Either this is a "new" discovery on the part of researchers into the properties of sulfonates, or it is a very serious misprint/typo in the published literature. The materials we have come from our notes and actual usage.

    PE

  9. #288
    Ian Grant's Avatar
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    Well the wealth of Patents that I've uncovered using Sodium Benzenesulfonate as an antioxidant in developers and thermal imaging emulsions plus what you say, and Mason (Levenson) seems to indicate it may have potential duel uses.

    The early 30's Agfa Patent is using a wetting agent sodium dibutyl-napthalene-a(alpha)sulphonate in a p-Aminophenol developer to overcome uneven development. This compound is the only link to the Kodak & Fuji patent(s) that cite it, and they all use Sodium Benzesulphonate or other derivatives as well in some..

    So what else did the Germans discover about using a sulphonate with a p-Aminophenol developer? Something that Fuji understood (much later), and Kodak (in the 40's). They are being used in ppd colour developers by Kodak at too high a level to be a wetting agent in USP 2618558 other cross citations go to other compounds used as antioxidants like Salicylic acid, andother sulphonic acids etc, USP 2444803 which is about anti-oxidants.

    There's to many cross links to just be a coincidence:

    Agfa/Bayer manufacture Sodium Benzenesulphonate
    A related derivative is in an Agfa Patent, alongside p-Aminophenol.
    Then Sodium Benzenesulphonate and derivatives are in Kodak Patent(s) not as wetting agents, there's only a trace of sulphite 0.5g to 5g PPD but 100g of the Sulphonate so it's the preservative. .
    More recently they appear again as anti-oxidants in Fuji Patents for developers and thermal imaging products, and also as an anti-oxidant in thermal imaging materials in the US

    Finally it's in the RO9 Formula that Pavel postedn and there must be some logic. There so many cross linked Patents Citations in two directions and often just hidden away but important

    Ian
    Last edited by Ian Grant; 10-05-2009 at 10:47 AM. Click to view previous post history. Reason: add quantities

  10. #289

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    Quote Originally Posted by Ian Grant View Post
    You need to read things , : Try another [...]
    US 3765892
    this is the one I cut & pasted from. I'm skipping between Patents rather fast... Ian
    Well Ian yes you need to read things.

    I don't understand why you are not more sensitive regarding your release of misinformation /misdirection but well, OK. whatever. You did finally get it right on your third try!

    I thought that text looked famaliar... I still have notes notes from Dr. Iwano's lectures - He is a very cheerful person. The last time I spoke to him was when the director of IPI was here, some months ago. (Photographer Eiko Hosoe was there as well - if you are one of those who like his work/ideas)

    Anyway I was quite happy to be reminded of Dr. Iwano.
    I think I gave him a really hard time!
    Be free of all deception, Be safe from bodily harm
    Love without exception, Be a saint in any form
    (Patti Smith)

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    I tried a search of USP 3765892 and find no reference to benzene sulfonates. The "find" utility in the PDF file does not find it, but it is found in the search of the text version. It becomes clear though that there are errors such as the claim of an antioxidant called potassium fulfite!

    Errors do happen. The point is that we do not know for sure in spite of that patent.

    I might add, in support of my comments, that diethy hydroxyl amine, which is claimed as an antioxidant, would be a very poor one for B&W developing agents, especially at that pH.

    PE



 

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