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I have a weekend update to do, and some fiber to get up, but my brain is in chemistry mode right
So, there are a lot of dyes out there in the world, made by a lot of different companies.
The most common kinds you will run into are as follows:
Acid Dyes
Reactive Dyes
Direct Dyes
There are subclasses of most of these, and some crossovers. I’ll also briefly touch on a group called
“Disperse Dyes.”
Ok. So, the difference between each of these classes of dye is in the way they interact with the fiber
you’re dyeing. That is, they have a different chemistry. No, not scary! Get back here! I’m going to
explain things logically and slowly, and if you have questions, feel free to ask them. I’ll try not to
I’m going to go through them from one end of the chemical spectrum to the other, starting with my
Acid Dyes:
First, what does this group include? Some of the things you’re probably familiar with…
Kool Aid
And more! But they all work via a similar chemical mechanism.
I’ve posted about acid dyes before, but I’ll duplicate some of it here.
First, the “acid” in “acid dyes” refers not to the dyes themselves, but to the environment they bind in.
For kool aid, the acid is already present in the mix (in the form of citric acid crystals), for other dyes,
Safety Sidenote: Both acetic and citric acid are food acids, that is, they’re not terribly toxic and won’t
kill you. However, when dealing with concentrated citric acid, or any hot bath with acid in it, be
careful. Inhaling large amounts of vinegar steam can irritate your throat and lungs and eyes.
Submerging your hands in these acids for any length of time can cause irritation and some skin
Acid dyes work via a combination of interactions with the fiber. I’ll explain each one.
Ionic bonding is a bonding between different charges on two molecules. Imagine acid dyes like little
magnets. Remember how if you put two magnets together, you have to put the S and N ends
together, or they’re push instead of pull together? Some molecules work the same way.
van der Waals interactions are like mini ionic interactions. Instead of a whole magnetic pole
Hydrogen bond interactions are weaker than ionic and stronger than van der Waals interactions, but
end.
Acid dyes can therefor bind to fibers which are “cationic” meaning they have one full positive charge,
An acid dye binds, like a magnet, when its “south” end binds to a fiber’s “north.”
There are many different ways to build an acid dye to get this “south” magnet effect. Some are
You’ll notice that in all of these examples, an SO3 group (or two) is present. This is the “south pole”
Acid Orange, many reds and oranges are shaped like this.
Acid Green, many if not most greens are shaped like this. Some purples and blues as well.
Acid Blue, this overall elongated structure is what a lot of the “leveling” dyes use.
A “leveling” dye, is a dye which naturally makes for a more even color coating. The way this is done is
by making a dye molecule with weaker binding potential (a weaker south pole) so that molecules can
bind and unbind to move about the fiber evenly. This is convenient, but the trade-off is that the dyes
can come off the fiber even when you don’t want them to. This is annoying if you want to wash your
Another concern that many have with acid dyes is that to get the deeper and intense colors, especially
For example, here’s ProChem’s black dye, acid black. It’s a “true black” or “primary black” meaning
that it’s not blended. But the intensity of color comes from that “Cr” in the middle of the molecule,
which is a Chromium atom. Chromium is a heavy metal, which makes this a dye you don’t want to
(You’ll notice this dye, as well, uses the “sulfonate” SO3 group as its ion, but also has a “nitro” NO2
group as well)
As a rule, companies try to limit the amounts of these heavy metals they need to use, and some
companies like Greener Shades try to eliminate them altogether. However, some colors are hard to
So, in short…
Acid dyes are anionic (south pole) dyes, which use heat and an acidic environment to form ionic bonds
with fiber.
Direct Dyes:
Dyes in this category are…
Any “universal” dye like RIT will have a Direct Dye as one of the two components
You can see already, that in some ways they’re similar to acid dyes, but their primary binding mode
utilizes a much weaker interaction. Still, they bind similarly to similar fibers.
Direct dyes tend to be very large in order to have more “subtantivity.” This means having more
surface area to contact the fiber and engage in more of these small van der Waals interactions.
Many if not most of the direct dyes will function as acid dyes as well. Look at this Direct Red dye and
See that SO3 group? Yep, acid dyeing group. The problem with these dyes is that being as long as
they are, and generally more balanced along their length, they again are easier to dislodge. You’ll
notice it looks almost identical to the “leveling” category of dyes, that’s because… the classes overlap!
More on what this means when I get to fiber chemistry in the next Dyeing 101 post.
You’ll also notice there’s more H’s hanging off, hydrogens that can be used in hydrogen bonds to stick
this dye to fiber that doesn’t have that “north pole” that the acid binding group (the SO3) needs.
Since these dyes rely generally on weaker interactions, they are less washfast and lightfast than most
acid and reactive dyes. Being big and floppy, they also tend to be duller in color (though this trait is
not uniform). The advantage of them is that they don’t require fiber with positive “north pole” groups.
Use some ionic, but mostly hydrogen bonding and van der Waals forces to bind to fiber. Less wash
and lightfast than reactive or acid dyes, but better leveling and don’t require cationic “north pole”
groups to bind.
Reactive dyes:
Procion MX
Dylon Cold
Lanaset/Sabraset
Cibacron F
Prochem Sabracron F
Remazol
Vinyl Sulfone
Reactive dyes us primarily a singular mode of binding, though most can use another as well.
Covalent bonds are what you think of when you think of molecules. “Actual” bonds. The kind that hold
the H-O-H of water together. Those little lines in all these diagrams are covalent bonds.
Covalent bonds are the strongest bonds, as such reactive dyes are the toughest when it comes to
being washfast.
I wish there was a better picture of this, but here’s a common reactive dye molecule…
The first thing you might notice is those SO3 groups. That’s what makes this able to function as an
But here’s the important part of the molecule, over there on the left…
Funny looking bit, isn’t it? Chlorines (note that when on the dye, one chlorine is replaces with the
dye)? Negative charges? Those chlorines would really like to rip a hydrogen off of your fiber and float
off happily as HCl (Hydrochloric acid), but that would leave that ring behind it bare! But wait,
whatever is behind the H the Cl ripped off is ALSO bare, usually an O or an N (Oxygen or Nitrogen) so
the two bare things can interact and form a new covalent bond, yay!
That means when the process is done, you have a dye molecule that is actually PART of your fiber
molecule, pretty cool? And depending how those interaction groups are designed, they can react with
all SORTS of things. Neat. The highly basic environment most reactive dyeing is performed in is to
make this process easier, similar in reverse to why acid dyes are done in an acidic environment.
Covalently bonded to oxygens and nitrogens on the fiber, making them ultimately washfast.
Disperse Dyes:
Disperse dyes are horrible and gross. They’re what you have to use to dye polyester and acrylic and
similar plastics. Ok, that’s not all true. There are ways to dye polyester without having to use the
noxious chemicals and super heat, Jacquard has dyes for it. But they’re still not pleasant dyes. I’m not
Acid Dyes: Anionic (negative), bind to cationic (positive) fibers. Can’t bind nonionic fibers. Fairly
Direct Dyes: Often anionic (negative) binds to nonionic fibers, and if anionic then it can bind cationic
fibers as an acid dye. Not very washfast or lightfast. Many can be used as weak acid dyes. A
Reactive Dyes: Covalent interactors, often with anionic (negative) bits as well. Given the right
environment can bind covalently to nonionic fiber, and possibly to cationic fiber. Many can also
Now, I’m sure by now you’re waiting for me to tell you WHAT fibers are cationic, and what fibers are
nonionic. You might be wondering if there’s anionic fibers too. We’ll get to that, but not in this post.
::waves:: As I said above, feel free to ask questions, clarify, or even argue with my chemistry.
Answers to Questions:
To Velma: By wandering around the web a lot. Here’s what I can tell you about ProChem’s stuff…
Sun Yellow, Basic Red, Bright Blue Red, Turqoise, Bright Blue, and National Blue are all non-metallic.
Carbon Black (Acid Black 52) is the chromium containing one. Here’s a link which has some minimal
information. As a rule, if you Google either the systematic name or the Color Index name, you can find
the structures of things. So for example… Acid Yellow 17 Sigma can be a good place to find these.
To Krissy: Usually, that’s how those fibers are dyed, from what I understand. They’re colored in the
Kellie: Feel free to link away. And anyone who comes here from there can also feel free to ask
(or in the case of ionic bonds, things which have charge). So, like you can’t stick a magnet to plastic,
David: The next big post in this series will cover the basic difference between fibers, animal, plant,
and others.
~The Gnome
Dyeing 101
Thursday, June 11th, 2009 | Author: The Gnome
Now, I hesitate to let the cat out of the bag, but probably not for the reasons most people would
expect.
You see, most independent dyers are loathe to make a post like this because their patterns and dyeing
methods are all they have to separate them from the scads of other indie dyers out there doing similar
work.
But you see, here’s where my real deep, dark, and dirty secret arrives…
I have one trick which I think is uncommon, but that’s because it doesn’t work on a lot of fibers.
I don’t have big secrets of dyeing methodology. I use very basic methods and very basic tricks.
I’ve written before about how I don’t dye scientifically. Perhaps that was a bit disingenuous, because
the truth is that while I use dyeing like an impressionist painter’s palette, I cannot (and wouldn’t
When I say, “know your fiber” I mean you have to know why things happen like they do. Pick up any
introductory dyeing kit or go to one of the dye company pages, head over to knitty and put “dyeing”
into the search, and it will give you a set of directions. Great, you can dye now, right?
Wrong. You should, if the directions are well written, be able to reproduce whatever effect (often
solids) the directions are written for. Because, if you follow the directions, you are essentially being a
But what if, instead of leaping in and following the directions, you sat and said, “Huh, why do they say
to presoak it? Why do I need to add dawn to the soak?” Then, you’d have understanding of what you
were doing, and suddenly you’d not be a machine trying to duplicate a process, you’d be a
comprehending artist with the ability to say, “but I want THIS effect so then I should be able to…”
I don’t use fancy tricks. I use very very basic methods, with no fancy ingredients or tools, all in my
kitchen, in an oven, one really big canning pot, one medium big heavy stainless pot, and a small
stainless pot. Most of my methods use simple resists very much like what you learned at summer
Because in the end, the real “trick” to dyeing, no matter how fancy the end product, is to know your
I make the colors I do because that’s what I see in my mind. I could no more describe to you the
process by which I look at a wet fiber and say “huh, you know that needs more brown, then it will look
much more like the mottle of a sphagnum moss.” than I could describe the reason one rosemary
cutting roots while its 10 neighbors just rot off or shrivel up.
That said, I’m going to do a series of posts here about dyeing. I know, I know, I just told you I can’t
teach you to dye like me. But see, that’s good! You can dye like you instead! Cool, huh?
So, if you’ve made it this far, you’re probably asking what’s going to be in these posts, right?
As I noted waaaaay up top, before I got all verbose and circuitous, there are a lot of dyeing tutorials
out there. Many of them are excellent, so I won’t duplicate them. I will likely link a few, but the
I can hear you saying, “Ok, Gnome, so what are you going to talk about? Quit lallygagging and tell
us!”
I’m going to talk about the science of dyeing. That is, what things do what, and why. I’m not going to
tell you how I do dyeing, I’m going to tell you how i think about dyeing.
Dyeing 101: Acid vs Reactive – What’s the Difference between Acid and Reactive Dyes? Direct?
What’s that?
Dyeing 101: Animal fibers vs Plant fibers – Protein vs Cellulose and What that Means
Dyeing 101: More Structure – Alpaca, Why is it Different? Silk, Why Won’t it Get Wet? Cashmere,
Eep?
Dyeing 101: Stuff You Add – Why Detergent? Why am I Soaking it? What’s the Vinegar for? SALT?
I will try to get to as many of these as possible, they’ll be spaced out as time permits. Because you
Also, I am sore. My living room is all reorganized, though not clean yet. I might actually be able to use
it. I think I might need to get rid of my spare couch, but I don’t know for sure, or how I’d do it.
Remember how I mentioned I was gonna talk about fiber reactive dyes ages ago, when I explained
how acid dyes work? and then went on to talk a little about things you can do about insolubility?
Well here it is, finally. I was dyeing again (also fnally) last night, and was thinking about this again.
This post is a little more chemistry heavy than the last one. Feel free to ask questions if things are
unclear.
So, fiber reactive dyes are slightly different than acid dyes. Acid dyes work by loose associations with
fiber. So while they are “fast” (don’t tend to wash out) they’re not actually “bound” in the chemical
sense. That is, if you drew a picture, there are no hard dark lines between the chemical structure of
Fiber reactive dyes take those loose associations one step further to make actual chemical (covalent)
bonds with the fiber. One reason for this is that plant fibers are slightly basic, while animal fibers are
slightly acidic. That means that an acid dye (which requires an acidic environment to stick) will never
are just to make it have color. The important part is that SO3 part in the top right. That’s our
“reactive” group.
This particular dye has a masking group on the reactive part (The Na – sodium – to the right, plus one
of the O’s) which prevents the dye from reacting with water (that SO2 sulfur dioxide group LOVES to
react with things) until you either boil it or add a very basic compound like soda ash to knock the
sodium off. Then the C-SO2 can bond with an C-O-H on the fiber and make C-S-O-C which is
I suppose I should note here that this is not a typical reactive dye, structurally. Most reactive dyes are
This is a Procion Yellow dye. In this, the loops behind the chlorine (Cl) are the reactive groups. The
chlorine comes off, and the ring reacts with the cellulose to make an “ether” bond, C-O-C (the corners
of the rings are C, carbons). The chlorine (unlike the NaO above) is more than happy to fall off as
soon as you add water, so it’s called a “leaving group” instead of being a masking group that has to be
knocked off.
Dyes like Procion MX don’t have that masking group, so you can’t put water in them until you’re ready
to use them, ’cause that reactive group will react with you water! Then it can’t react with your fiber
anymore, and much sadness abounds. However, not having the group means that you don’t have to
get the masking group off at all, which means almost all your dye will react with something, even if
it’s the water. So, if you’re fast, the non-masked dyes are “more reactive” (more of it will react with
If you actually want to do fiber reactive dyeing, Knitty has a good article.
~The Gnome
Right, so yesterday I told you why your red turns to glop and your yellow won’t dissolve.
Which, of course, left you saying, “Well that’s great, but now what?”
The “easy” thing to do, would be to replace the water. Because water doesn’t get along with our
yellow (and to a lesser extent, the red), because magnets like magnets, and our yellow… well it isn’t a
magnet.
So, what would be easiest would be to make the solution the dye is dissolved in also be a not-magnet,
balanced, hydrophobic (water hating) molecule. Unfortunately, hydrophobic solvents are generally
highly caustic and thus not available. Things like… phenol and formaldehyde and benzene (Benzene is
Ew. Even if your average dyer could get those chemicals, you wouldn’t really want your yarn/fiber
soaked in gas, or flesh dissolving goop. Neither would these chemicals play nice with your green and
The answer is, anything that doesn’t affect the dyeing chemistry itself. Which means we can add quite
The most straightforward things to add are things which will interact with both hydrophillic magnet
molecules and non-magnet hydrophobic molecules. So, molecules which have a balanced end and an
unbalanced end.
Detergents. Detergents are molecules which have a hydrophillic “head” and a hydrophobic “tail.”
Your laundry “detergent” is a detergent (in the chemical sense). And the way it works is by forming
little groups around your hydrophobic dirt particles, tails (non-magnet ends) pointed in at the dirt, and
heads (magnet ends) pointed out at the water. This lets you wash the dirt off with water.
“Soaps” are a specific kind of detergent scientifically called “surfactants” or “surface active detergents”
because they have a higher than normal ability to wrap all the way around those little hydrophobic dirt
particles, even if that means pulling them off a surface (you, your clothes, etc).
So, you might be able to add some detergent to your dye bath to help the yellow go into solution. The
problem is that most commonly available detergents are soaps, which means they are really good at
sequestering things (wrapping all around and not letting it touch anything) which can inhibit your
dye’s ability to, well… dye. So, go ahead and add a little detergent (the naturally less foamy your
detergent the more likely that it will help) but it may or may not solve the problem.
Humectants. These are similar in overall structure to your detergents. They have a hydrophillic and a
hydrophobic end, just like detergents. The difference is that their hydrophillic end is REALLY
hydrophillic. They don’t just get along with water, they actually hold onto it. The other difference is
that your humectants are less able to gang up and “wrap around” hydrophobic molecules, so they
won’t stop your dye from interacting with things. Basically, they can make believe that your
hydrophobic molecule actually likes water. This is why they’re often called “wetting agents.”
These are overall a better choice than the detergents, and are fairly readily available. Glycerol and
urea are the two most common ones. Urea is generally cheaper, but smells funny and in very large
amounts can screw with things. Glycerol is a little gunkier to deal with but doesn’t interact with just
Salts. If you have especially soft water (lacking in calcium and magnesium) then a small addition of
salt can help to increase the disorder in your solution, but it’s not likely to help a great deal unless
your water is REALLY soft (if you scrub forever in the shower and that detergent never comes off you,
same reason).
So, if you’re having trouble with crashing or goopification, try adding a little detergent. If that doesn’t
Or, use the tried and true method of increasing your free energy and system entropy… put it back on
And yes, for those of you wondering, I will post about non-science stuff. Maybe even tomorrow. I
might even talk about… knitting! Or you know, that spinning stuff I do!
~The Gnome
The Gnome is a nerd. Yep. I don’t research because I have to, I have to research.
Someone on Ravelry asked a question about dyes (not an uncommon occurrence in a dyeing group).
Specifically, it was a question about why acid dyeing yellow is a pain in the butt and falls out of
solution.
Now, most people would satisfy themselves with something to the effect of, “It’s a yellow thing” or
even a “It’s a chemistry thing.” But not me, oh no, none of that simple answer for THIS gnome!
You see, I am one of those freaks you might have known in college. Remember how all the bio and
chem majors would always moan about this horrible class they had? A class who’s horror reached
almost mythic proportions, a monolith almost insurmountable? That class was called, “Orgo” short for
“Organic Chemistry.” And I was that kid, yeah, That Kid. The one who loved it. Even when I was
So when someone asked, “Why does my yellow dye always fall out of solution as soon as its cool?” I
started researching (in my spare moments when I wasn’t dunking my yeast in formaldehyde). And
So, you probably want to know what the answer is, don’t you? Well, I’ll tell you. I’m going to try to
write this such that it goes from the simplest explanation to the most complete explanation, so you
can read as far as you want and not be overwhelmed. Because the truth is, most people don’t care
about the in depth chemistry. But for those who do, I’ll try to explain things in non-jargoned terms (or
Question: Why does my yellow dye fall out of solution when cool?
Corollary Question: Why do some of my red dyes form “jello” when cooler?
Most basic corollary answer: Because your red dye likes itself
One of the most basic divisions of chemicals is between those that love water, called “hydrophillic”
(meaning, literally, “loves water”), and those that hate water, called “hydrophobic” (meaning “fears
water”).
Example: Oil is hydrophobic. That’s why it makes little bubbles when you mix it with water.
Your yellow dyes are “hydrophobic,” thus the most basic answer.
Hydrophobicity, the “amount” a molecule hates water, is controlled by how “balanced” a molecule is.
Think of an unbalanced, water loving molecule like a magnet. If a molecule is not balanced, its exactly
like a magnet, with two ends or “poles.” Those poles can attract other unbalanced magnets. Strong
magnets are all about getting together with other strong magnets. They have fun molecule parties. If
the magnets are strong enough… well you can’t pull those magnets back apart again!
So the trick is that the balanced molecules don’t get along with the unbalanced ones. All those magnet
molecules want to cluster together, so they can line up South poles near North poles and balance each
other out, right? But the balanced molecules don’t have any poles, so any magnet nearby doesn’t
So the magnet molecules all get together and line up end to end around the non-magnet molecules
and make itty bitty bubbles around them, ostracizing them from the party. Bam, you’ve got bubbles of
oil! (or yellow dye). If all those water molecules get really lined up (ordered) then you get… ice! Ice is
I can hear you now, “So wait, if my dye hates water, why does it ever go into solution? And why
Quick answer: ‘Cause your dye isn’t as hydrophobic (water hating) as oil, and not all dyes were
created equal.
When you heat up your water, all those magnets get hyper (think steam!). When they’re bouncing
around, they don’t line up very well (the ice melts) and so they can’t ostracize those non-magnet dye
particles as well, and the little bubbles burst and your dye dissolves into solution, until it cools down
But why doesn’t it happen to your blue dye? Why is yellow the worst?
Here comes the chemistry. Ooh scary. Nope, not really. Just gonna show you some pretty pictures and
point at things.
Here is the core of a yellow acid dye. This is called a “trityl” group.
See those hexagons with the little double lines? Those are very hydrophobic. They really don’t get
along with water well, because they’re very very balanced. There’s some little bits hanging off that
aren’t shown here, which make it kinda go into water if you heat it, but not enough to make it stay
there.
Again, see those rings? Hydrophobic. The little bits hanging off the two ends are what make it yellow
(by changing the way it interacts with light). Like before, they make it able to go into water, but not
well.
“But wait, if this is what my dye looks like, why doesn’t the green do this? Or the blue? If green is blue
Ah, right. Green. The answer is, depends on the green. Some greens are mixed blue and yellow, but
some are “pure” greens, that is the dye itself is green. Pure greens are similar to yellow, but with
than it’s yellow cousin. You can also see how the big rings aren’t as evenly spaced as in the yellow
example. This lets water into that center space, again making it more soluble.
“Ok, but what about my corollary question? Why the heck is my red making jello?”
Right, the jello. Ok, we’re going to go back to that second yellow dye
Remember? Now, reds are made from a similar base, but the big water-hating rings are a little further
apart, which lets water in between (like that twist in the green dye), but also the way they make them
red, and not yellow, is by adding big doo-dads on the two ends (where the HO- is and on the far end).
These moieties (doo-dads) make the whole molecule unbalanced enough to interact with the water.
But in some cases, if the end magnets are strong and the middle part water hating, your red can line
up in big long strings, end to end, making balanced ropes with water hating middles! This lining up is
called “polymerization” and is exactly what happens in jello, and is similar to the ordering of ice.
Warming up the solution makes the magnets hyper again and things move around and your red goes
So, that’s why your yellow falls out of solution and your red sometimes makes jello.
~The Gnome
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