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Old 10-11-2008, 11:19 AM
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Azo Yellow vs Cad Yellow

I recently saw an Azo Yellow offered my M. Graham. It is about half the cost as Cad Yellow, which I've used for years.

Can anyone tell me if Azo Yellow mixes well with other colors and does it have approximately the same mixing properties as Cad Yellow?

Thanks!
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Old 10-11-2008, 06:30 PM
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Re: Azo Yellow vs Cad Yellow

It doesn't compare with Cad Yellow for opacity or tinting strength. It was one of the pigments that turned me off to Graham paints (that, and Napthol Red).
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Old 10-12-2008, 04:07 PM
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Re: Azo Yellow vs Cad Yellow

Thanks for the evaluation!
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Old 10-12-2008, 07:00 PM
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Re: Azo Yellow vs Cad Yellow

Winsor & Newton makes "Transparent Yellow 653", which is an AZO Condensation, and is identified as PY 128.

It is a transparent paint, and it mixes with other colors to provide some of the deepest colors, and "near-blacks" that you can imagine. It is especially effective when used for dark greens. When mixed with white, it springs to life with brilliant color, making it quite suitable to use for painting flowers, and for mixing with other colors to create extremely clean secondaries.

It is a wonderful Yellow, and except for the fact that it costs over twice the price of Cadmium Yellow, I would use it almost exclusively, as I consider it to be as close to true, primary yellow as any yellow I've used. As it is, I use it in a pinch, when I want deep, dark colors with a decided yellow cast, and for demonstration purposes to the oil painting students that I teach. It appears quite unremarkable, when freshly-squeezed from the tube, simply because it is a transparent Yellow, and transparent colors appear quite dull, dark, and lifeless in their masstone state. But, its advantages are in the use of it for mixing, and this includes both dark AND light colors. Cadmium Yellow is not as appropriate for making deep greens, simply because it brings to the mix, too much "white" content (other reflectances). In short, it is too opaque, and light to be useful for mixing dark values of any color, including greens.

This Transparent Yellow 653 is one of those colors that has to be used appropriately, or it might otherwise be considered a rather useless color. It is extraordinarily useful for certain applications, and for those applications, is nearly indispensable.

Bill
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Last edited by WFMartin : 10-12-2008 at 07:02 PM.
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Old 10-12-2008, 07:09 PM
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Re: Azo Yellow vs Cad Yellow

Quote:
Originally Posted by WFMartin
Winsor & Newton makes "Transparent Yellow 653", which is an AZO Condensation, and is identified as PY 128.

It is a transparent paint, and it mixes with other colors to provide some of the deepest colors, and "near-blacks" that you can imagine. It is especially effective when used for dark greens. When mixed with white, it springs to life with brilliant color, making it quite suitable to use for painting flowers, and for mixing with other colors to create extremely clean secondaries.

It is a wonderful Yellow, and except for the fact that it costs over twice the price of Cadmium Yellow, I would use it almost exclusively, as I consider it to be as close to true, primary yellow as any yellow I've used. As it is, I use it in a pinch, when I want deep, dark colors with a decided yellow cast, and for demonstration purposes to the oil painting students that I teach. It appears quite unremarkable, when freshly-squeezed from the tube, simply because it is a transparent Yellow, and transparent colors appear quite dull, dark, and lifeless in their masstone state. But, its advantages are in the use of it for mixing, and this includes both dark AND light colors. Cadmium Yellow is not as appropriate for making deep greens, simply because it brings to the mix, too much "white" content (other reflectances). In short, it is too opaque, and light to be useful for mixing dark values of any color, including greens.

This Transparent Yellow 653 is one of those colors that has to be used appropriately, or it might otherwise be considered a rather useless color. It is extraordinarily useful for certain applications, and for those applications, is nearly indispensable.

Bill

Bill,

Interesting! The M Graham is half the price of the Cad Yellow. Thus my interest.
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Old 10-13-2008, 08:57 AM
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Quote:
Originally Posted by WFMartin
Winsor & Newton makes "Transparent Yellow 653", which is an AZO Condensation, and is identified as PY 128.
Different pigment Bill! Pigments from the same family can have little similarity to each other, not least in colour, e.g. the strengths of weaknesses of some naphthol reds don't equate with all naphthol reds.


Brian, are you interested in the oil, acrylic, watercolour or gouache version? The colour of this name is made from a mix in acrylic and oil (PY74 & PY151, an arylide/azo/hansa yellow and a benzimidazolone yellow) and just the second pigment in watercolour and gouache.

As gunzorro says it'll be less opaque (much less opaque) and lower in tinting strength. It will also be much more transparent, although not truly transparent like the paint Bill waxed lyrical on.

If it doesn't matter that it's not the same in those respects it's made from reliable pigments and it's a bright, 'clear' yellow that will mix both oranges and greens well. It would make a very solid choice for a primary yellow on the palette in the semitransparent range but if you value opacity in your yellow and in the mixes made from it then you pretty much have no choice but to stick with cadmiums.

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Old 10-13-2008, 10:50 AM
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Re: Azo Yellow vs Cad Yellow

Quote:
Originally Posted by brianc
I recently saw an Azo Yellow offered my M. Graham. It is about half the cost as Cad Yellow, which I've used for years.

Can anyone tell me if Azo Yellow mixes well with other colors and does it have approximately the same mixing properties as Cad Yellow?

Thanks!

Brian, as I understand your question, you are asking if Azo Yellow mixes well with other colors, and has the same mixing properties as Cad Yellow.

The Winsor Newton "Transparent Yellow 653" that I mentioned, IS identified as an "Azo Yellow Condensation". And, if that isn't the "Azo" about which you're speaking, I'm afraid I wouldn't know what else to call it. Perhaps M. Graham's version of Azo is different, and perhaps an "Azo Condensation" is different than an "Azo". But, I can state from experience, it not only mixes with other colors as Cadmium Yellow does, but it mixes with other colors MUCH BETTER than Cadmium Yellow does, in terms of being more versatile, and mixing a greater gamut of possible colors (both dark AND light), than Cad Yellow. In terms of quality and practicality, it is an extraordinarily useful pigment, if those are the qualities you're seeking, regardless of its identification.

My point is that I'm recommending a very useful paint. Whether it is precisely the identical "Azo" pigment you're seeking, or not, I'm not sure, but that didn't seem to be your primary concern, initially. Apparently you are interested in replacing Cadmium Yellow, and this will most certainly do that, and IN SPADES--no matter what it may be called. For that purpose, you may find it well worth the price. And that ain't "waxing" anything!

However, if your primary concern is strictly based upon price, or upon some urge to try M. Graham paint, I'm afraid that I can't offer much advice that would interest you. I'm simply trying to steer you toward a very useful paint, that will perform as you requested, or better.

Bill
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Last edited by WFMartin : 10-13-2008 at 11:00 AM.
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Old 10-13-2008, 03:07 PM
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Quote:
Originally Posted by WFMartin
The Winsor Newton "Transparent Yellow 653" that I mentioned, IS identified as an "Azo Yellow Condensation". And, if that isn't the "Azo" about which you're speaking, I'm afraid I wouldn't know what else to call it. Perhaps M. Graham's version of Azo is different, and perhaps an "Azo Condensation" is different than an "Azo".
Oi vey Bill

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Old 10-13-2008, 05:05 PM
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Re: Azo Yellow vs Cad Yellow

Well, I'm willing to try to turn this thread around into more of a learning thread, in hopes that something productive may come from it.

Is it true that "Azo Yellow" from one company (M. Graham, for example) is likely to be a totally different pigment than "Azo Yellow" from another company, such as Winsor & Newton? In this respect, perhaps it is a similar condition to that of the term, "Cinnabar". I know from some experience that Cinnabar from one company may be red, while Cinnabar from another company may actually be green. In this case, I believe the term, "Cinnabar" refers to something other than "color".

Another good example of meaningless "names" for paint colors is the term that Old Holland uses to describe many of their colors, for which they use the term, Schevenengen (sp). I believe that Schevenengen is actually some town in Holland, and could be just as useful in describing a red as in describing a blue--which, quite honestly, is not of much real "use," whatsoever.

So, the Azo Condensation color that I've been describing has a pigment ID of "PY128". What is the pigment ID of the M. Graham Azo Yellow? I simply don't own a tube of that brand of yellow, or I would look at it.

If, indeed, an "Azo" is different than an "Azo Condensation," I would honestly like to know that, as well. Perhaps it represents the same pigment, but also represents a difference in the manufacture, and, therefore, a different color. This would also be nice to know.

Again, this Winsor & Newton Transparent Yellow 653, that I am recommending as an excellent replacement for almost ANYBODY'S Cad Yellow Light, it IS called an "Azo Condensation", it IS transparent, and its Identification IS PY128.

Please inform us all of the pigment ID of M. Graham's Azo Yellow oil paint. I am quite interested in knowing that, if nothing else, for the sake of pure academia. Being a results-oriented person, the color that comes out of a tube is nearly always more important to me and my operation, than the markings, names, and ID's printed all over the tube, itself.

Sorry if I seem to be ignorant of the facts regarding specific pigments, and the manufacture thereof, especially regarding paint manufacturers whose paint I only own a few tubes of, but here is an opportunity to "set me straight".

Now, I don't speak French, but "grisaille", "trompe' l'oeil", "oi vey", "hasta la vista" and "verdaccio" to you, too!

***(I'm not kiddin' 'bout my yellow bein' a GOOD ONE, though.)

Take care,

Bill
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Last edited by WFMartin : 10-13-2008 at 05:18 PM.
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Old 10-13-2008, 06:11 PM
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Post #6 Bill... the one immediately above your second one!

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Old 10-13-2008, 09:01 PM
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Re: Azo Yellow vs Cad Yellow

So, will the REAL "Azo Yellow" please stand up!? Is it,....then,....PY 74 and PY 151 mixed, by M. Graham? Or is it.....PY 128, as manufactured by Winsor & Newton?

And, the chief difference (either in color, manufacture, or pigment) between "Azo Yellow", and "Azo Condensation" Yellow would be....???

Then, can we assume that because of the seemingly ambiguous nature of the term, "Azo", that it has very little to do with the particular color OR pigment of which it is composed? Does this mean that when we buy a tube whose color is termed, "Azo Yellow", that we might expect just about ANY color of yellow to emerge from the tube?

If this is true, it seems to place the term, "Azo Yellow" in about the same category as that of "Cinnabar", or the term, "Scheveningen," to which I alluded, earlier, except, of course, that would encompass the same basic hue of "Yellow", instead of its hue bouncing all over the color wheel.

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Last edited by WFMartin : 10-13-2008 at 09:28 PM.
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Old 10-13-2008, 11:06 PM
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Re: Azo Yellow vs Cad Yellow

Sorry Bill, that's not exactly the case. "Azo" describes a family of chemically similar pigments, like, say how cadmiums would be the same chemically, but look completely different depending on if they were PR108 (red) or PY35 (yellow).
The arylides and di-arylides are common place pigments with adequete permanence in oil paints (usually ASTM II, but sometimes III -- some are ASTM I, hence many are not as permanent as you might like, depending on the exact pigment). As such, their color (hue) and transparency are the chief distinction between the pigment numbers. One is not interchangeable with another, as you see.
For anyone interested in painting brilliant bananas, I would hesitate to recommend cadmium red, a cadmium pigment.

From Handprint (probably hugely overkill, but it goes to the point of the confusion over the broad family of Azo pigments):

Monoazo (arylide). A family of about 30 azo pigments, identified by the term arylide, providing almost exclusively yellow hues. Many (PY3, PY65, PY73, PY74, PY97 and PY98) are commonly marketed under the trademark name Hansa Yellow, first introduced in 1909. The two orange (PO1 and PO6) and red (PR211) monoazos are not used as artists' pigments.

The structure of PY3 is characteristic: a pair of carbon rings, joined by nitrogen to a central cluster of four carbon atoms (note the double nitrogen atoms just left of center). Variations in the hue arise from additional atoms hung asymmetrically off the outer carbon rings. About 5 different monoazo pigments are commercially available in watercolor paints. In general the monoazos are serviceable and relatively inexpensive colorants, semitransparent with good tinting strength. Unfortunately they have only moderately good lightfastness in artists' materials. They work very well as student paints, but always should be tested carefully for lightfastness before using in a major work. (The naphthol pigments are also sometimes classified as monoazo pigments, for example by the Colour Index International.)

Disazo (diarylide). Another family of about 30 azo pigments developed around 1940, identified by the term diarylide, and (like the monoazos) providing mostly yellow hues of special significance to the printing industries. The three orange hue diarylide pigments are relatively impermanent.

The structure of PY83 is representative: two identical arylide molecules, in opposing orientation, joined at the same carbon ring. Variations in the hue arise from differences in the atoms arranged around the outer (end) carbon rings. Diarylide pigments are very important in printing inks, but only one (PY83) is currently offered in watercolor paints. Although the diarylides are often more saturated and have higher tinting strength than the arylides, the doubling of the molecule unfortunately also significantly reduces the lightfastness. For that reason these pigments are generally not suitable in artists' colors, especially watercolors.

Disazo Condensation. A small group of 17 azo pigments formed, like the diarylides, of two coupled arylide molecules: but these are joined in condensation with a bifunctional hydrocarbon molecule — hence the name. An industrially economical process to do this was discovered in 1951 by M. Schmid at CIBA, but use in artists' paints has been very limited. Available hues range from yellow (PY93, PY95, PY128, PY166), orange (PO31), red (PR144, PR166, PR214, PR220, PR221, PR242, PR248, PR262), and brown (PBr23, PBr41, PBr42). The few available as watercolor paints are semitransparent, have high tinting strength, and are typically very lightfast (more lightfast than analogous monoazo pigments, though also more expensive).

Benzimidazolone. An important group of about 20 azo pigments with a broad range of hues, from yellow (PY120, PY151, PY154, PY175, PY180, PY181, PY194), through orange (PO36, PO37, PO60, PO62, PO72) and red (PR171, PR175, PR176, PR185, PR208) to a maroon of fair lightfastness (PV32), and a delicious brown (PBr25). Developed and patented by Hoechst in 1960, the benzimidazolones were first used as watercolor pigments in the late 1970's. They are relatively expensive, but are also among the most durable pigments used in artists' paints. (Winsor & Newton, for example, has chosen a benzimidazolone pigment for their "winsor yellow" and "winsor orange.")

The structure of PY151 is representative: a base structure very similar to the arylides, but with a charactertistic triangle of two nitrogen atoms and a carbon atom attached to the righthand carbon ring. Variations in hue arise from different arrangements of atoms attached to the lefthand (and sometimes the righthand) benzine rings. As a group the benzimidazolones are nontoxic, saturated, semitransparent and nonstaining, provide beautifully clear if somewhat bland colors (on all counts, cadmium pigments provide a revealing standard for comparison). For lightfastness alone the benzimidazolones should usually be preferred to comparable arylide or diarylide pigments in artists' colors (although there are a few benzimidazolones with only good lightfastness, such as PY120). The widest range of benzimidazolone colors are available in watercolor paints made by Winsor & Newton, Rembrandt and Daniel Smith. Curiously, "benzimidazolone" is also the pigment name most often replaced by "permanent," "winsor," "azo" or some other marketing moniker (I especially like DaVinci's "benzimida" as a nickname). To my ear, "benzimidazolone" is no harder to say (or remember) than "Benji, my dad's alone!" and everyone seems to be getting along just fine with the label "quinacridone" ... but marketing prejudices about artists die hard — very hard.

Beta Naphthol. A relatively small group of azo pigments, among the oldest synthetic organic pigments, providing primarily red (toluidine red PR3, PR49, PR53, PR68) and a few orange (dinitraline orange PO5, PO17, PO46) hues. First produced around 1870, only a few of these pigments are still used today, and primarily for inexpensive applications because the pigments are cheap to manufacture and only moderately lightfast. (The 16 BON arylide pigments, with few exceptions all middle red to bluish red hues, are also acceptably lightfast when laked to manganese salts.) Most beta naphthols not sufficiently lightfast for use in watercolor paints and are now found only in student paints (Blockx stopped using them in their ³professional² paints in 2006).

Naphthol. (Naphtol is a registered trademark of Hoechst AG; the generic label for the same compounds manufactured by other companies is naphthol, with a second h. The word is from the Greek for "mineral oil", and salutes the origin of these pigments in petroleum.) Developed and patented in 1911, the naphthol compounds represent the single largest group of azo dyes and pigments. (In fact, about 20% of all synthetic organics available, over 50 in the red category alone, are naphthol pigments.) Originally used as cotton dyes, they were soon laked as pigments and were first used in artists' paints in the 1920's. The most important group for artists is the naphthol AS pigments. The color range is concentrated in the long wavelength end of the spectrum, including warm orange (PO24, PO38), scarlet (PO5, PR188, PR261), many reds (PR2, PR3, PR5, PR7, PR8, PR9, PR17, PR22, PR112, PR150, etc.), carmines (PR23, PR146, the many pigments listed under PR170), maroon violet (PV13, PV25, PV44), and brown (PBr1).

The structure for PR112 (for artists, one of the most important naphthol AS pigments) is typical: two carbon rings linked by nitrogen to a central structure of two overlapping carbon rings. Variations in the hue arise from a different arrangement of atoms attached to both the lefthand and/or righthand carbon rings (in PR112, the three chlorine atoms on the left). Naphthols are nontoxic, often extremely saturated, and in watercolors are semitransparent and strongly staining pigments. The middle reds are especially brilliant: they are traditionally used to make lipstick. Lightfastness in watercolors varies from poor to very good, so it matters which specific pigments you choose.

Reputable watercolor manufacturers seem to accept PR112, PR170 and PR188 as "lightfast enough" pigments; PR112 and PR188 have held up well in my own lightfastness tests, but PR170 seems to me marginal and better left in the tube. Admittedly these are splendidly vibrant and sexy pigments, but if you worry whether your hot date has the permanency your mom requires, always do your own lightfastness tests.

Last edited by gunzorro : 10-13-2008 at 11:11 PM.
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Old 10-14-2008, 02:10 AM
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Re: Azo Yellow vs Cad Yellow

Well, that was nice.

However, it did answer my questions. So let me restate the questions and answers so those who are not chemical engineers might understand it.
_________________________

So what is the "real" Azo Yellow?

And, the answer would be that there basically IS not ONE, particular "Azo Yellow". Funny, then, how that doesn't make my initial comment regarding MY choice of an "Azo Yellow" to seem quite so ignorant, since MY choice of "Azo Yellow" is not any more "illegitimate" than M. Graham's is--in fact, possibly a bit MORE legitimate, because mine represents a single pigment. And, I'm not sure that I really want any "atoms hung assymetrically, off my outer carbon ring". LOL
________________________

What is the difference between "Azo Yellow", and "Azo Condensation Yellow".

Apparently mostly chemical, rather than of color, and something that most of us will never need to actually know, in order to buy the color of yellow that we require for our work.
________________________

Does this mean that when we buy a tube labeled, "Azo Yellow" that we can expect nearly ANY color of yellow to emerge from the tube?

Apparently.....Yes. In this respect, it seems as elusive as the names, "Cinnabar", which can be either Red or Green, and "Schevenengen," which can be nearly ANY color.
________________________

Wow! It must have taken some work to copy all that off the Handprint site. Personally, I gave up paying much attention to the author of that site when he once claimed that there were no such things as primary colors, and that one could effectively select ANY colors off the color wheel to use as primary colors. As one who has worked with, and taught color behavior for over 40 years, I could disprove those comments about a dozen ways. But, he's probably correct about all these chemical considerations, though.

Bill
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Old 10-14-2008, 02:31 AM
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Quote:
Originally Posted by WFMartin
And, I'm not sure that I really want any "atoms hung assymetrically, off my outer carbon ring". LOL


Quote:
Originally Posted by WFMartin
Apparently.....Yes. In this respect, it seems as elusive as the names, "Cinnabar", which can be either Red or Green, and "Schevenengen," which can be nearly ANY color.
If you think about it that's no different from Cadmium Orange (q.v. the differences between the one you have and the average one). It's nothing unique, not even unusual, to this family of pigments.

Quote:
Originally Posted by WFMartin
Wow! It must have taken some work to copy all that off the Handprint site. Personally, I gave up paying much attention to the author of that site when he once claimed that there were no such things as primary colors, and that one could effectively select ANY colors off the color wheel to use as primary colors.
That's not quite what he says, the comments have to be read in context.

Regardless, it would be a grave error to overlook the site just because of differences in philosophic outlook regarding one thing, given that it proves its validity in so many other ways.

Quote:
Originally Posted by WFMartin
As one who has worked with, and taught color behavior for over 40 years, I could disprove those comments about a dozen ways.
And the reverse Bill, and the reverse! As we've discussed before, given the difference between theory and paint in this area the points about the non-primary nature of 'primary' paints, as well as what perfect primaries would actually mean in practice, can't be brushed away because they're inconvenient. Lots of things about actual paint, compared to colour in the abstract, are inconvenient.

...

Remember people, one can paint without any primaries - i.e. without Yellow, Cyan or Magenta paints - ergo their importance to the painter is much less than is often supposed. And that's something so fundamental that it should be taught in every 'colour theory' class in the world

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Old 10-14-2008, 09:21 AM
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Re: Azo Yellow vs Cad Yellow

Well, in terms of your own vernacular......oi vey!

Paint on.

Bill
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