Quaternium-15 is a formaldehyde releaser?

[Jorpho]

So I somehow found myself today at the Wikipedia article for Quaternium-15, which is a darn sexy name for a compound if nothing else.

Wikipedia calls it a "formaldehyde releaser", but gives no details. The molecule contains no oxygen atoms, so how exactly would it release formaldehyde?

[Mr Pete]

Wild stab in the dark:

Hydrolysis of the N⁺ - C bond to give a protonated NR₃H⁺ and HO-CH₂-N. Which then breaks down to formaldehyde and a secondary nitrogen.

The vinyl chloride could also be involved in some way.

[AvatarIII]

the fact it is Quaternium-15 made me think perhaps it contains an isotope that turns into oxygen, but Carbon-15 decays into Nitrogen-15 which is stable. although Nitrogen-16 decays into oxygen, in fact every isotope of Nitrogen higher than N-15 decays predominantly into oxygen.

[PM 2Ring]

Somehow, I doubt that "a preservative [used] in many cosmetics and industrial substances" would be manufactured with a radioisotope as a principal ingredient.

[AvatarIII]

Somehow, I doubt that "a preservative [used] in many cosmetics and industrial substances" would be manufactured with a radioisotope as a principal ingredient.

well, potassium is radioactive and we regularly eat it.

although saying that, surely it's equally unlikely that cosmetics would contain a compound that released formaldehyde? perhaps it has a very long half life and therefore only releases radioactive particles, and formaldehyde very slowly.

[Jorpho]

Hydrolysis of the N⁺ - C bond to give a protonated NR₃H⁺ and HO-CH₂-N. Which then breaks down to formaldehyde and a secondary nitrogen.

Sounds plausible, I guess.

the fact it is Quaternium-15 made me think perhaps it contains an isotope that turns into oxygen, but Carbon-15 decays into Nitrogen-15 which is stable. although Nitrogen-16 decays into oxygen, in fact every isotope of Nitrogen higher than N-15 decays predominantly into oxygen.

None of those appears to have any kind of meaningful half-life. The production and purification of such isotopes in adequate quantities would surely be too expensive to make the compound useful.

well, potassium is radioactive and we regularly eat it.

Apprently only 0.012% is radioactive, and even then it has a long half life.

although saying that, surely it's equally unlikely that cosmetics would contain a compound that released formaldehyde?

Formaldehyde does occurs naturally in some fruits and vegetables; in the quantities involved it is probably no worse than some of the other harsh chemicals that end up in cosmetics. (There's probably a better-written article than this one out there, but it will do for now.)

[AvatarIII]

so why's it called quaternium-15?

[qetzal]

Quaternium is almost certainly short for 'quaternary ammonium,' which refers to the postively-charged nitrogen atom that's bonded to four different carbons (see the structure in the Wikipedia link in the OP). 15 is probably just an arbitrary number to distinguish from other quaterniums (e.g. 18, 22, 26, 87, according to Google).

However, I can't find any actual reference on where the name came from.

[gmalivuk]

You both noticed the Wikipedia link in the OP, right?

[Jorpho]

Alas, said link offers no details regarding nomenclature.

[gmalivuk]

No, but it does explain what "quaternium" means, and contains a link to the polyquaternium page which states, "The numbers are assigned in the order in which they are registered rather than because of their chemical structure."

[qetzal]

Nope. Saw the link in the OP, of course, but didn't see that particular link in the link. Thanks.

I also never did find real data on the supposed formaldehyde release mechanism. In fact, there's apparently disagreement over whether it really does so at all: abstract.

[Carlington]

the fact it is Quaternium-15 made me think perhaps it contains an isotope that turns into oxygen, but Carbon-15 decays into Nitrogen-15 which is stable. although Nitrogen-16 decays into oxygen, in fact every isotope of Nitrogen higher than N-15 decays predominantly into oxygen.

This and this beg to differ, good sir. Also, I apologise for being late, I realise that we've all already accepted that it's not radioactive.