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Failed Experiments Starting With Dye Powders And Distilled Water


FrMark

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I really wish I knew what dye molecules are typically used in commercial inks. I don't expect them to tell me! My choices were guided by some chemical intuition and by what was on the shelves.

One company went so far as to name themselves after their signature chemicals, "Diamine". Not one chemical so much as chemical class with lots of variations. I think there used to be a lot of aniline's too.

Edited by Corona688
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Thanks. There are many classes of molecules that are dyes that are water soluble to varying degrees. Id figured diamine probably was a reference to some of the underlying compounds.

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Another thing to note, I got out a bottle of Thymol today and made an ethanol solution of it to use as a preservative until I can get my hands on something better. The resulting brew smells exactly like a ?70? year old bottle of Waterman's Carnation Red.

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You'll have to mail me one so I can know what that smell is ;)

Better: get some thyme from the grocery store, stick a tablespoon in denatured ethanol, put lid on bottle shake for a minute or so, maybe let it sit a while, un cap, and see what it smells like. It'll be similar anyway. Actual thyme has several smell chemicals in it, but I think the thymol is 60% or more from something I read. If I ever get a mixture I like I will want to trade around samples. I think that's a long way off.

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That was a joke inviting you to mail me said rare antique-smelling ink, so I can draw my own conclusions on what it smells like ;) But I already have a full bottle of W&N Carnation which smells quite weird anyway.

 

If you can use extract of thyme as a preservative, that's interesting!

Edited by Corona688
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Some other data:

 

pH of Sheaffer Blue (modern) 3.76

pH of Sheaffer Black (modern) 8.36

 

pH of a 10 mg/ml solution of FD&C red 40 with some propylene glycol (from low toxicity anti freeze) and thyme and photo Flo (none of which besides the dye should affect pH) pH 9.52

 

I added EDTA to neutralize and overshot by a lot and got to pH 4.8 and not all the EDTA had dissolved. Note to self, sometimes doing calculations is a good idea!

 

This brew works great on Strathmore 400 series drawing paper (my current notebook) I've had rather less success on other papers i.e. crazy feathering, at least with a a dip pen. Dip pens seem to put more ink down than fountain pens and I've been playing with a zebra G so I can really put some ink down but it does it even w/o pressure on the nib. I find that I have to do some testing with a dip pen because it takes to long to clean out FP's.

 

propylene glycol will confer great freeze protection, I see noodler's claims an ink that won't freeze to minus 81 Centigrade or about -114 F. I think you can get that temperature at the S. Pole in the Winter. Maybe, like in a good year. I don't see how they can do that and have an ink that writes on ordinary paper, in my hands, much beyond 10% propylene glycol the feathering gets way out of control except on great paper.

 

Addition of more than 1 drop (0.05ml?) of 1/10th strength Photo Flo to 1 mL of dye also makes for v. wet/feathering dye. Photo Flo contains both triton X100 (non ionic detergent) and propylene glycol and water. I'm not sure of the proportions beyond the MSDS which says 25-30% propylene glycol and 5-10% the detergent. The other ?60% is water, presumably.

 

I feel like I need a thickener that will make the ink stick to the nib better and not feather so much but it still has to wet the paper and pen surfaces...lots of variables here and I know almost nothing about rheology and additives for that.

 

I have my Parker 75 filled with this mix right now to see how it behaves:

 

I made a 10ml sample:

4:1 mix of FD&C Yellow 5:Blue 1 (50 mg/ml ea or 400mg Y, 100 mg B in 10 mL H2O w/ 1-1.25ml propylene glycol) about 10% Propylene Glycol, a drop of 10% w/v Thymol in Ethanol, 10 drops of 1/10 diluted photo flo. This works pretty well out of the fountain pen, better than the dip pen, not sure why. It tends to crust up on the nib a bit, but has not made any clog or hard start or fail to keep feeding ink so maybe this is a good working mix. I did not measure the pH yet. I've written maybe 10-15 pages with it on 25% cotton letterhead paper and I like it well enough.

 

I also put a 1 mL sample of Parker black in a beaker in a fume hood to dry out so I can get an idea of % solids in the ink. I'm sure each ink is different, but I have to start somewhere and it might also help me when I try to reconstitute found bottles of antique ink (I've got a bottle of Sheaffer's blue washable from ??. It's a blacker blue than I'd prefer, but it is fun to write with the dip pens. I don't feel safe putting it into my FP. Next time I will add a bit of ethanol first to dissolve the hard to dissolve in water bits first then add water.

 

I know I said I wasn't going to work on this, til at least after Easter, but it is an intriguing, if frustrating problem. Most research is endurance of frustration broken up with isolated moments of joy that usually fail to counterbalance the frustration, but sometimes way tilt the scale toward happiness.

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Some other data:

 

pH of Sheaffer Blue (modern) 3.76

That's vaguely unsettling, wonder if they realized that, or it changed over the years.

I don't see how they can do that and have an ink that writes on ordinary paper, in my hands, much beyond 10% propylene glycol the feathering gets way out of control except on great paper.

Perhaps their ink binds to the paper somehow? I get crazy feathering, but it's short-lived, as my pigments stay put.

Addition of more than 1 drop (0.05ml?) of 1/10th strength Photo Flo to 1 mL of dye also makes for v. wet/feathering dye. Photo Flo contains both triton X100 (non ionic detergent) and propylene glycol and water.

Is that what the alcohol-ether word-salad is? Thanks. I figured out the glycol, the rest had me baffled.

 

I feel like I need a thickener that will make the ink stick to the nib better and not feather so much but it still has to wet the paper and pen surfaces...lots of variables here and I know almost nothing about rheology and additives for that.

Since you're in a lab, do you have methyl cellulose? It's a powerful and inert thickener used in microscopy work but also shampoos, fake blood, etc. It does not help it stick to the nib, that's the surfactant's job, but in combination maybe...

 

The trick to dissolving the powder is to put it in hot water to prevent it dissolving (its got a weird solubility curve) then stir continuously to keep the powder dispersed until it cools.

 

Thanks for the photo! I like the 30:1 red/blue, that's both very nontraditional looking and also something nobody would bat an eye at when you use it.

 

If your paper's not white, putting something white in the picture, even just a cotton ball or something, may help your pictures. The camera should color-adjust to the white instead of the cream.

Edited by Corona688
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I don't know the pH for old Sheaffer ink. I never imagined I'd end up collecting old ink, but I'm in the hunt for it now! I have an old bottle of waterman's carnation red or red carnation, I forget which way around it is. I'll have to look at the pH of that one. I have an old bottle of Sheaffer blue #42, but it was dried out and when reconstituted it's blacker of a blue than I'd prefer, not bad, just not perfect. I like the bottle though with the well near the opening so I can stick a pen in it without getting the ink way up on the side of the pen or having to pay to close attention to the sides of the bottle when using a dip pen.

 

I haven't seen any methyl cellulose. The contents of the lab stockrooms is weird. It reflects the interests of various professors long gone, I think, crossed with the needs of what they use in v. inexpensive undergraduate teaching labs.

 

Not that I'd put it in fountain pens, but I'm pretty sure we have the ingredients in the lab to make an iron/tannic acid ink. I might use it in fountain pens if 1. I could filter the results and 2. I could buffer it so it wouldn't eat the metal parts in some fountain pens. I may read these forums again for the iron/tannin ink recipes to have some to use with the dip pens.

 

I have the feeling I'm missing something obvious that "everyone" who makes commercial fountain pen ink knows, but of course they aren't telling because this stuff is all trade secret. If it were simpler, more people would do it, kind of thing and no one would make any money selling colored water (ink). I'm probably weird in that it bugs me to pay $10-20 for a bottle ink that I know has 1/2 to 1 gram of active ingredients excluding water. Of course it is also weird to want to spend more than a nearly lifetimes supply of ink cost to figure it out! I've not spent any money on this, I've used materials that were in danger of being thrown out. Some people think there's a business lurking in this. I don't know. Noodler's is filling the space pretty well already that the "big" names left open. I'm not sure what I'd be able to offer that he isn't doing already except maybe lower toxicity and published pH's and maybe some information in each package about the history of dyes in general and the ones used in particular.

 

Ex. Fluorescein was used as an aid to finding downed military aviators in WW2 and in the space program water recoveries, and is used to help diagnose certain eye conditions and to color bubble level fluid.

 

Does anyone think people would choose an ink if it were certified organic?

 

Triton x100 or 100x or whatever is a trade name for the "word salad" name that Kodak puts on the bottle and MSDS. There must be thousands of different detergent molecules for different applications: hi/lo foam (you don't want foam in a dishwasher!), etc, etc.

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Ink binding to paper:

 

I forgot to address that. Two thoughts, yes and sort of.

 

By which I mean I'm pretty sure that for some inks Noodler's is using procion (sp?) dyes which are made to react with cellulose fibers and form a covalent bond to the cellulose and never wash out. This would work on paper, most of it is cellulose, either from trees or cotton the dyes were developed to make color fast tie dye shirts and probably more normal dye application to cotton if I understand correctly. It would not work on all writing surfaces, some are made from animal skins (?vellum?) and those are nearly 100% protein (collagen) and probably/possibly wouldn't react with the linker portion of the dyes. I have to read more but I think I read somewhere that procion dyes aren't for wool (collagen again) or silk (a different protein). I've not looked into the chemistry of those dyes yet, however. Dyes nearly created the industrial revolution, certainly the chemicals part of it so there's a history going back to the 1800's of synthetic dyes continuing to the present. It's an enormous body of work, just the dyes. formulating them is another enormous challenge!

 

Some dyes have a greater affinity for cellulose than others. you see this in paper chromatography where some dyes run with the water and others stay where you put the initial ink dot.

 

Then there's the case of colored paper where the chemicals absorb into the fibers and are changed by UV light into nano particles that are insoluble and stuck inside (not stuck in between or on the surface) the paper fibers. This is a process for printing photos though, not for fountain pens. Although, that said, it might could be used in fountain pens...hmm...but the resulting nano particles can be easily chemically bleached so you won't see them, though I'm not sure the colorless material that results is soluble so it might be available for forensic analysis. Who'd want to write with pale green and have to take out in the sunlight to make it turn dark blue, almost black. Me maybe, but who else? It'd be absolutely waterproof, more than most paper, actually. So maybe some would. And as long as you didn't raise the pH above neutral it's permanent. There are photos in this chemistry 150 years old. I have a LOT of the solution for this made up. Might have to try this.

 

As to the color of the paper, the paper on the edge of the photo with lots of writing on it is white, the paper stapled into the notebook is some stationary from church that when I arrived I found in my desk and had the name of the prior priest printed on it so I've been using it as way nice scrap paper---I like the cream color. I ought to go to the custom printing shop and buy a box of it and/or find out what it is and make some journal books with it or something.

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Pale green and blue-black -- are you talking about cyanotype? That sounds interesting. People still write with iron gall after all.

Edited by Corona688
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Pale green and blue-black -- are you talking about cyanotype? That sounds interesting. People still write with iron gall after all.

 

Yes, cyanotype, though using Dr. Mike Ware's New Cyanotype recipe. It's a one solution sensitizer with great shelf life and better Dmax/dynamic range than most recipes.

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I have the feeling I'm missing something obvious that "everyone" who makes commercial fountain pen ink knows, but of course they aren't telling because this stuff is all trade secret.

 

I suspect there's a sweet spot of density, viscosity, and surface tension we're revolving around without hitting... Density is easy to measure in the absolute, viscosity tricky to measure but straightforward to compare with flow cups. Surface tension is the trickiest to measure but perhaps the easiest to change. If the first two are imitated well enough, perhaps the third can be fudged by trial-and-error.

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I look forward to seeing the results.

Fountain pens are my preferred COLOR DELIVERY SYSTEM (in part because crayons melt in Las Vegas).

Create a Ghostly Avatar and I'll send you a letter. Check out some Ink comparisons: The Great PPS Comparison 

Don't know where to start?  Look at the Inky Topics O'day.  Then, see inks sorted by color: Blue Purple Brown Red Green Dark Green Orange Black Pinks Yellows Blue-Blacks Grey/Gray UVInks Turquoise/Teal MURKY

 

 

 

 

 

 

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Someone linked an MSDS for Pilot Varsity which looks revealing.

 

I think the black blue dye is this copper-containing word-salad: "trisodium[29H,31H-pthalocyaninetrisulphonato(5-)-N29,N30,N31,N32]cuprate(3-)", present at 0.4% by weight. Yup, its a dye.

Triethanolamine is present at 0.1 - 1.5% by weight. Wikipedia confirms that it's a surfactant, and also a chemical base.

Then there's phenol, present in 0.3-0.4%, probably just preservative.

 

Searching from that, there's one for their bravo marker which contains 1-3% triethanolamine plus a whopping 7-8% ethylene glycol.

 

One for Sheaffer Skrip doesn't reveal anything about their dyes and humectants, except that Skrip Blue-Black and Royal Blue might be iron galls!

 

The MSDS for Windsor & Newton calligraphy inks is exceptionally useless, stating they are odorless (NOT) and contain nothing harmful.

 

An MSDS for Parker Quink states "water, diethylene glycol, dyes, preservatives".

 

Pilot's MSDS seems a lot more revealing than these North American ones, probably because it's an import.

 

Pelikan "Fount India" is preserved by 0.1% isothiazolinones.

 

This one for Pelikan 4001 lists "N-methyl-chloroacetymide", probably a preservative.

"chloromethyl-isothiazolinones" - a preservative.

"6-acetoxy-2,4-dimethyl-1,3-dioxane" - a preservative.

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Looking up pthalocyanine found me a lot of stuff. There seem to be endless variations, but obviously some are more used than others - some cost $300 for 500 milli grams while others sell for hundreds of times less. This one seems particularly cheap, and as the most popular pigment in the history of mankind ought to be. But it's a pigment, not an ink - insoluble. Oops.

 

That trisodium stuff now, though - that's known as "acid blue 249 direct blue 87", is definitely soluble, generally harmless, and fans out to a lot of leads.

 

Here's an expensive book which mentions it, but from the google preview, ought to be a pretty comprehensive answer to your question - exactly what dyes are used for everything, everywhere?

 

And the dye itself, how much does it cost? In quantity, thirteen dollars per kilogram. Which, thinned out to 0.4%, ought to make about twenty liters, 357 ink bottles, or 13,000 Parker cartridges full of fountain pen ink.

 

All that for $13. Just add water.

Edited by Corona688
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I had a similar relevation about food recently, at that. You can get oats for $170 per metric tonne, meaning, a box of cheerios contains about twenty cents worth of food. All the rest is grinding, pounding, baking, shipping, packaging, and profit.

Edited by Corona688
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