A bit of Chem: Flavonoids and Anthraquinones

So, someone asked a question while I was away. It was a good question.

It had to do with natural dyes and flavonoids, and how they compare to anthraquinones.

“What?” some of you are no doubt querying.

The Difference Between Dyes

Fiber Chemistry

Anthraquinones are a common structure for acid dyes to be based off. Flavonoids are a common structure for some natural dyes.

So here’s the most basic structure of an anthraquinone:

Anthraquinone

And here’s the most basic structure of a flavenoid:
Flavone

You can see, they’re pretty similar. Big difference is that the phenol rings (the hexagons) have a linker in flavenoid, and not in the anthraquinone. As you get more complicated, that starts to seem a little less important.

One important thing to note here is that these basic structures make the chemical colored, that’s actually the most defining feature of a dye chemical. The “dye” aspect is usually added on after the fact, or if it’s a natural dye, is a lucky chance addition for the dyer.

Here are some simple-ish anthraquinone dyes:

dyes

Acid Blue, Vat Violet, the dye that makes your gas blue, and Disperse Red

These are dyes made synthetically, but the colors from lichen, fungi, rhubarb, buckthorn, and senna are all anthraquinone colors as well.

Here’s an example of a far more complex flavenoid dye. This is marigold dye, “patulitin.”

marigold

And here’s a few flavenoid colors…

Luteolin, the yellow from weld:

Luteolin

Quercitin, the yellow from onions (and part of the color from oak and tea):

Quercitin

Which is all a very long, roundabout way to say that structurally they are very similar. Most of the natural dye flavenoids are in the yellow/orange range (but not universally so), while the anthraquinones are mostly in the blue range (but not universally so). The main difference between them as DYES, is that with most flavenoids you need a mordant in order to serve as a linker to bind it to the fiber, while most anthraquinone dyes are synthesized with an acid moiety like a sulfate or the like. But the natural ones (aforementioned lichen, etc) will need a mordant, just like the flavenoids.

Hope that answers your question!

That’s all for now!
~The Gnome

Fae

Spinning for Socks: Q & A

WilyG asks: What do you mean by 2×2 Chain-ply?

A: What I mean is actually “cable” ply. For some reason I keep calling it chain plying, which is the same as Navajo plying (plying via a giant crochet chain). Cable-ply is when you take a plied yarn and ply it to another plied yarn. A 2×2 cable-plied yarn would be two two-ply yarns plied together. So, a 4 ply yarn, made of 2 2-plies.

———

Ted: What is “hosiery twist?”

A: Hosiery twist is a tight plying. In most technical terms, it’s 15.35 tpi (twists per inch)

———

Feel free to ask any more questions you’ve got!

EDIT: Fixed the bit about cable/chain plying.

That’s all for now!

~The Gnome
Gnome

Spinning for Socks

This post will be about spinning handspun yarn for knitting into socks. If you want the supershort bullet point version, it’s at the end of the post.

First a couple of disclaimers.

1) This is, of course, all my own opinion. It will match with some other people’s in some places and differ in others. It is neither expected nor intended to be the be-all end-all treatise on the subject. As with most things, if it works for you… it doesn’t much matter if it’s “right” or not.

2) Example socks were knitted by a very dear friend of mine who is a far faster and more skilled knitter than I. I have knit socks, these just aren’t them.

3) In case it’s not clear, these are recommendations and assume all else is equal. Fiber choice, for instance, assumes you can pick any fiber you want. It does not mean you “shouldn’t” use corriedale if that’s what you have in your stash that you love.

Ok, now, the meat and potatoes… oh wait, no first an appetizer. A side salad if you will.

Millspun Yarn

Before I talk about handspun, I need to note that millspun is not the same. I will write quite a bit here (Spoiler alert!) about how Merino is wrong for handspun socks. I’ll get more into why I believe that to be the case shortly, but for now it’s enough to say that much of that is due to my views on spinning in general.

Those who’ve followed me a little more closely will be saying, “But, Gnome! What about Phouka?” Indeed, indeed. My own sock yarn, Phouka, is a merino/nylon blend. Like I said, millspun is not handspun. I have quite a few millspun merino socks, and they’re lovely. With a soft spun single and a hosiery twist in the ply they can be springy and have a very nice stitch definition.

Phouka Socks
Cables

And I can wash and dry these without ever worrying about them at all. I love them.

I also have some millspun dorset socks. They are also fabulous. The yarn, however, is quite different. The socks are springier, but with less stitch definition. Similar to the difference between dress socks and SmartWool hiking socks.

Dorset
Dorset

Both yarns are fabulous. Both pairs of socks are fabulous. The Merino socks have less squish, so they fit in dress shoes better, and have better stitch definition for cables and the like. But I wouldn’t go hiking in them (which I have in the Dorset socks).

So yeah, that’s millspun. It’s not the same as handspun. Now, on to the meat and potatoes!

Handspun Sock Yarn

From what I’ve been able to glean, reading, talking, etc. with people around “the community” most philosophies of spinning can be grouped into one of two main categories.

Spin the yarn to the fiber – Pick your fiber so it naturally makes the yarn you want to make

Spin the fiber to the yarn – Modify your spinning to make the yarn you want out of the fiber.

There’s nothing inherently “better” about either method. There are very talented and “famous” spinners (how famous are any of us, really, in the scale of pop culture?) on both sides of this amiable venn diagram. They’re simply different ways of approaching the same problem, how do you get the yarn you want?

Myself, I am a member of the “Spin the yarn to the fiber” school of thought. [/insert tongue in cheek] Clearly, this means spinning the yarn to the fiber is the right way to do it. The One and Only Way. Clearly. Oh wait. I just said it wasn’t. Ahem. I mean… uh…

Right! So, any time you’re going to spin a particular yarn, you need to know the essential elements of the yarn you’re making.

For a sock the most important aspects are

1) Durability – You don’t want them to wear out, and your feet put a lot of wear on things.

2) Comfort – You’re going to be standing on them.

3) Memory – Spring, sproing, cushy. They need to support you, have enough spring to hug your foot, etc.

There are other features that can be important depending on your needs. We’ll get to some of those later.

Fiber Choice:

Since I said my philosophy for spinning means picking a fiber that lends itself to the yarn, I should talk about picking fiber. Feature numbers one and three in the above list are the largest reasons I lean towards the downs wools and the almost-downs wools for handspun socks.

Downs wools (dorset, tunis, cheviot, shouthdown, hampshire, etc) have a spiral crimp rather than a wavy one. This makes them look, and act, like a spring. If you squash it or stretch it, it will bounce back to its former shape. This is called “memory” and gives you that nice cushioned feel under your feet. The springy effect also makes for a bouncy fabric with a nice negative ease that hugs your foot.

Here’s where comfort and durability cross…

These downs wools aren’t as fine as merino but that actually can be a good thing. Super fine fibers tend not to be very strong. Silk is an obvious exception, however silk’s strength is almost entirely tensile. That is, you can pull hard on it and it won’t snap. But abrade it, rub it on something rough, and you’ll wear right through it. Merino can be made to be slightly more durable (like in the better millspun yarns) with things like hard plying that packs the fibers closer together.

This is where the philosophy of spinning thing comes most into play. By spinning it right (plying tightly), you can make a fine wool like merino or rambouillet or polwarth durable enough to be a sock yarn. Or, you can use a downs wool. The downs wools tend to be in the “medium” category of fineness, so they’re naturally more durable. You don’t have to spin/ply nearly as tightly to get the same durability. This means in the end, you end up with similar softness either way, but a different overall handle. Downs wools will tend to make a squishier, springier fabric.

All that said, these aren’t hard and fast rules set in stone. What it tells you about is the overall ideals for getting particular kinds of fabric. Downs wools felt poorly and are springy. The wools I mentioned before are ideal for that reason. However, other wools will work. These, for instance, are shetland.

Shetland. Handspun from a top prep. (Note, they’re fat from my calves, I put them on briefly before taking the photo)
Shetland
Shetland

Shetland felts more easily than the “true downs wools” but that isn’t necessarily a bad thing. If you’re gentle with them they will only felt a little bit on the edges of the yarn. This can make for an even more durable fabric that wears really well. I have found I need to be a little more careful with them, however. They will shrink slowly even in cold/cold wash.

Spinning Method:

Again, there’s several theories here. So we’ll take them back to the points I mentioned above. The big ones here are one and two, durability and comfort, with a side of durability.

So you’ve got two(ish) spinning methods, right? Longdraw and shortdraw, worsted and woolen.

I’ve read more recommendations for worsted/shortdraw spun yarn because it makes a smooth, tight yarn which in theory could be more durable…

But I can’t say I’ve noticed a difference in durability between my worsted and woolen spun socks. The first sock yarn I spun was also my first longdraw project. And the socks are wearing fabulously. My guess would be that this is because with a springy fiber, the halo from longdraw actually helps protect the core of the yarn as long as the core is still spun tightly enough.

These are handspun longdraw (by me) from a hand drum carded prep. Romney with a little silk and mohair.

Socks

You’ll notice I said that was from a carded prep. Indeed. Like the suggestion of a worsted spin, most would suggest a true worsted spin, which means from a top prep, not a carded prep. But again, I haven’t had any problem with these. If you’re worried, I find a short draw spin even with a carded prep tends to make a fairly “worstedish” yarn.

I’ve also read a lot of recommendations for three or more ply yarn because it’s rounder and more durable (because it’s more rounded). This is also a matter of comfort, and as always, “It depends.”

These are handspun socks from two-ply yarns spun from Shetland and Black Welsh wool
Shetland/Black Welsh

They are super comfy and wonderful. Again, my guess is that the Shetland slightly felted to the nearby yarns, making the fabric smoother than it would be otherwise.

I’ve heard great things about 2×2 cable-ply yarns, though I haven’t worn socks from that myself. A spinning advantage of this ply is that you can do it with a single long single, ply back on itself then ply back on itself again. Which is convenient. I want to spin up some of this soon and I’ll report back.

Bullet Points Version:

Fiber:
First choice wools – Dorset, Cheviot, Tunis, Hampshire, Portland, Black Welsh, some blends (stage whisper: my New England Blend)
Second choice wools – Shetland, Romney, soft Jacob, Perendale, etc.
Other wools – As noted in the disclaimer, this is NOT to imply that you can’t use fibers not on this list and be happy with them. These are the common fibers I’d choose if I had access to every fiber out there.

Spinning:
Prep – Advantages to both carded and combed preps. I haven’t seen a massive advantage to either. Top may be more durable for washing.
Method – Again, no massive advantages. Short draw may be more washing durable.
Ply – In general I like three or more plies. But a two-ply can work very well, depending.

Care:
Everyone will tell you to wash handspun socks by hand. This is definitely the wisest thing. I am lazy and do not do this. My socks are pretty much either superwash or downswools. Superwash doesn’t felt (mostly) and downswools felt very poorly. I wash in a lingerie bag on cold/cold with very light detergent. It’s worked very well for me.

Fine Wools:
A final note on “Merino is r-o-n-g wrong.” I would not use merino for handspun socks. Other people would, do, and are happy with the results. And it *does* have the advantage that it comes in superwash, which little else does (BFL, and recently, Cheviot). If I was going to spin a fine wool (say you have super special snowflake feet, or that’s the fiber you have in the “right” color) then I would probably use one of the springier/coilier fine wools. Targhee or Rambouillet would probably be decent finewool choices. If you were going to use these, I would recommend a worsted (short draw) spin and a tight plying to maximize durability.

I think that’s all for now. Feel free to weigh in, ask questions, etc.

EDIT: “Chain” switched to the correct “cable” in plying section

Gratuitous Puppy: Gobo sleeping with Mokey’s dollie
Gobo

~The Gnome
Gnome

Dyeing 101: The Chemistry of Fibers – Soy, Milk, Chitin, Etc.

Allo! Another chemistry lesson!

So, a lot of people know that fibers are largely divided into two classes. Protein, and cellulose. Proteins are what make the strong flexible fibers in animals, hair, skin, muscles, even collagen. Cellulose is the main ingredient in plant cell walls. It’s what gives the plant its strength and shape.

Many of the fibers are thus obvious to categorize. Wool and alpaca and dog and bunny and goat are all animal fibers, and all protein fibers. Cotton, flax, hemp, and nettle, are all cellulose, plant fibers. But many fibers are not obvious, like chitin, or seem obvious but actually aren’t, like soy or even silk.

So the first thing to understand is the basic chemistry of a “protein” fiber or a “cellulose” fiber. How are they the same, how are they different?

Protein Fibers:

We’ll start with a protein fiber. Protein fibers are actually made of multiple layers of proteins bound to each other in different ways to make the many different types of fibers you’re familiar with. However, here’s the important part.

Protein molecule

This is a simple, four amino acid (piece) protein. If you stuck a bunch of these together you’d have a “polypeptide,” a protein fiber. You can tell it’s four pieces, or amino acids, because I’ve conveniently labeled each amino acid’s “R group” with a number. That’s because what’s in the R group doesn’t really matter for this part of the discussion. They affect things like durability, crimp, and tensile strength, but not dyeing.

What’s most important for your dyeing purposes are those N-H bits, called “amine” groups (which is how amin-o acids get their name!). These amine groups are the signifying feature of a protein. And, if you remember my previous post on the difference between acid and reactive dyes, they’re the part that acid dyes bind to.

So, any fibre that’s made up of these amino acids, with their NH and NH2 groups, is a protein fiber, and will dye with acid dyes. Got it?

Cellulose Fibers:

Cellulose fibers have a different structure, with no amino groups. Celluose is made of strings of glucose sugar instead of amino acids. Like protein fibers, natural cellulose fibers are more complicated than this, with layers and such, but also similarly, this is the important part.

Cellulose

The important part here is those “OH” groups hanging off the edges, called “hydroxide” groups (’cause they have a HYDRogen and an OXygen). Those are the parts that interact with reactive dyes (when you put the fiber in a basic solution). So, any fiber made with cellulose molecules, is a cellulose fiber, dyed with reactive dyes.

“Odd” Fibers:

So, that’s the easy part. Now lets look at some weirder ones. We’ll start with soy. Soy is a plant, right? Of course! It’s where we get edamame and soy beans and tofu. Mmm tofu. Yay plants! So it should be a cellulose fiber, that dyes with reactive dyes, riiiight?

Well… no. (Bet you didn’t see that coming!)

You see, there’s another way to divide fibers, though it’s not as all-around helpful for things like dyeing. Synthetic and natural. That is, fibers which are used more-or-less “as is” and fibers which we have to create.

The obvious “fibers which are used more-or-less ‘as is'” are the wool/hair/fur/cotton fibers. We pluck or shear them off the animal or plant, clean them, and use them, simple. Slightly less obvious are the “bast” fibers which are cellulose fibers that naturally grow for strength and flexibility in some plants. Flax and hemp are excellent examples of bast fibers. To collect these we “ret” (partially rot, how’d you guess?) the rest of the plant away from the bast fiber, clean it up, and spin it. Examples include of bast fibers are flax/linen, hemp, ramie, some bamboo, nettle, wisteria, and milkweed.

So the “natural” fibers are the fibers which already exist and we just collect and use them.

The “synthetic” fibers are fibers that we have to make. Most people, when they think of “synthetic” think of things like acrylic, plastics. And, of course, acrylic is synthetic. But in this case, I use synthetic in its more complete sense of synthesized, or combined from two or more parts. Again, there are some fairly clear cut examples of this, and more confusing ones.

A clear example is milk, and a confusing one is the soy I mentioned above. We’ll start with milk.

Milk is clearly… not a fiber. And not particular fibrous to boot. If you’re like most non-chemists you probably wonder where in the heck they found fiber in milk! And you’d be right, there IS no fiber in milk! What there is, is casein, a protein made of many amino acids. In fact, it’s the majority of the protein in whey protein you can get as a dietary supplement. Another protein that looks roughly like…

Protein molecule

So you string a bunch of those together, and you get a fiber! And, as you’d expect looking at the chemistry, this is a protein fiber, made with lots of amino (NH and NH2) groups and thus dyes with acid dyes.

Now, back to soy. Soy is, indeed, a plant, but the thing to know about soy fiber is that it is not a bast fiber. That is, the soy fiber doesn’t come out of the stalk of the plant as a fiber. Instead, soy fiber, like milk fiber, is a synthetic fiber, actually made from the bean. The leftovers of the bean after they make other products have a high quantity of the amino acid lysine in them. So, they take the amino acid lysine, stick it all together in strings, and you again get…

Protein molecule

A protein molecule all stuck together into long fibers, and thus a protein fiber that dyes with acid dyes, even though it came from a plant!

The Odd Case of Synthetic Cellulose:

Many of the other “new” fibers are in this synthetic class, but are made slightly differently than soy and milk. Seacell, Viscose, Tencel, Rayon, and Lyocell are all examples of what is called “regenerated cellulose.” These terms can be a bit confusing as they’re all essentially the same fiber with variations in word choice or fiber origin.

Basically, they take an already existing cellulose (wood, seaweed) and then break it down and string it back together into fibers to look like this again.

Cellulose

Bamboo is an interesting example in that it exists in two forms. There is “bamboo rayon” which is a regenerated form of bamboo and far far more common. However, bamboo does also have a bast fiber that can be harvested and used. Both are still cellulose fibers, of course, so will dye with reactive dyes.

“Combination” Fibers:

Finally, two of the odder examples of fibers… silk and chitin. We’ll start with chitin.

Chitin fiber, also called crab fiber, comes from exactly that. The chitin (shell) of crabs. It could also come from the chitin in insect shells or shrimp shells or any other arthropod. So… clearly not a cellulose fiber, right? Since there’s no cellulose in a crab.

So what is “chitin” actually made of? Well, the chemical answer is “polymerized N-acetylglucosamine.” Now, what do you notice about that long, complicated word? The first thing with any complex chemistry word is to split it into it’s pieces.

So… “polymerized” means it’s something all strung together, interesting but not useful. “N” well that’s boring, useful to a biochemist to know where it came from, but not for anyone else. Ok, what else? There’s “acetyl,” “glucos,” and “amine.” Ah, now these could be useful.

Depending on your memory, you’ll have already locked onto the second two words, “glucos” which looks a lot like “glucose” and “amine.” Good job, those are the important parts to us.

But now you’re thinking, “But Gnome, wait, glucose is what you said cellulose is made of! And amines are what you said proteins are made of! What are you trying to pull here?!”

Well… I also told you chitin was weird, didn’t I? Because you’re right, glucose is what cellulose is made of, and amines are what proteins are made of! And “glucosamine” is a glucose with an amine group! Ok… so… lets draw out the chemistry and see if that tells us anything, ok?

Chitin Fiber

Chitin fiber is made of strings of this. You’ll notice overall it looks a lot like the cellulose fiber, and in fact you can actually make half-cellulose half-chitin fibers! But remember how I said what the important parts of the protein and cellulose fibers were in terms of dyeing?

Chitin Important Parts

In pink are the OH, hydroxide, groups that are useful in reactive dyeing. In green are the NH2, amine, groups that are useful in acid dyeing. So you can see that chitin is odd in that it will bind with both acid and reactive dyes. But you can also see that it will bind better with reactive dyes, as there are more hydroxide binding sites. And you can guess that overall it will behave like a regenerated cellulose fiber.

Now, silk. Similarly odd. Silk is an animal fibre, but unlike most animal fibers, it’s not a hair/wool/fur fiber. Instead, silk is formed of protein polymers layered on top of each other. Each repeating motifs of this sequence…

Silk Structure

If you look at it the same way as we looked at the chitin fiber, you can see that there’s a lot of amine (NH and NH2) and only one hydroxide (OH) per stretch of silk. So, in reverse of chitin, silk dyes more easily (and usually more deeply) with acid dyes though reactive dyes will also bind to it.

Summary:

So, that’s the dyeing chemistry of fiber, with a focus on how they differ and the odd fibers.

Protein fibers are made of amino acids and include: wool, alpaca, dog, goat, rabbit, milk, silk, and soy.

Cellulose fibers are made of strings of glucose and include: cotton, flax/linen, ramie, bamboo, seacell (seaweed), tencel (wood), hemp, wisteria, nettle, and milkweed.

Chitin dyes as if it was a cellulose fiber, even though it’s not cellulose. Silk dyes as the protein fiber you’d expect but will also dye like a cellulose fiber though not well.

So. Any questions?

And, of course, your requisite gratuitous puppy.

Dogs

~The Gnome
Fae

Bottom Whorl Spindle Myths (A Video)

So I’ve had this for a while now (as evidenced by the fact it was filmed at my old apartment).

I keep thinking that I’ll do an addendum to it, or add something or what have you. But I don’t. So… I’ll post it as is. If it needs a new version, or an addendum, then you – dear readers – can tell me what you’d like to see.

So, here’s a small video I made about bottom whorls. Specifically it was meant to address two of the big myths I’ve seen spread about.

1) Bottom whorl spindles are heavy

2) You can’t spin fine on a bottom whorl

There’s also some basic explanation of how to use a bottom whorl, if you’re interested. Personally, I love my bottom whorls. I want to get another at some point, since my big one tends to be full of plying projects as it’s my longest shafted spindle (see earlier post with 4.2oz of icelandic plied onto it).

So, without further ado, here it is. Bottom/low whorl spindles.

Let me know if you have questions, comments, etc!

P.S. Thanks here to Tom, for filming this for me.

That’s all for now…

~The Gnome
gnome