Indelible Lipsticks


As women began to put on lipstick in the early part of the twentieth century they discovered that it had an unfortunate tendency to easily come off. Attempts to make lipstick stay on the lips were made from then on and lipsticks that advertised themselves as achieving this described themselves as ‘long-lasting’, ‘deep-stain’, ‘stay-on’, and ’smeer-proof’ but I will call them ‘indelibles’.

Although lipsticks of the indelible type could be found through most of the twentieth century they were generally more popular in the United States. There they had two main periods of high levels of consumer interest; the first in the 1920s and 1930s and the second in the 1950s during what is known as the ‘lipstick wars’.

The formulation of indelible lipsticks in each of these periods was very different. In the early lipsticks the only way to make them indelible was to dyes, as pigments would quickly rub off.

Pigments and dyes

Up until the 1920s most lipsticks were coloured with the pigment carmine, a red lake pigment extracted from cochineal beetles. Carmine looked a deep red in the stick but was less intense when applied to the lips. If a brighter red shade was required, zinc oxide was added, while other lake pigments like yellow and vermillion were used to produce variations in shade. A typical formulation is listed below.

Mineral oil (Russian, heavy)64 ozs.
Petroleum jelly, white32 ozs.
Ceresine31 ozs.
Paraffin wax, 50/5233 ozs.
Oil Carmine1 oz.
Scarlet Lake, cosmetic quality15 oz.
Red Lake24 oz.

(Jannaway, 1937)

As well as lacking in intensity, as the colours were pigments they could be easily rubbed off, meaning that the lipstick would need to be frequently reapplied. To make a longer lasting lipstick, finely ground, water-soluble dyes were sometimes added to the wax-oil base along with the carmine. These would stain the lips so that a colour would remain on them after the pigment was rubbed off.

Daylight Stick, No. 1520
Carmine50
Carmosine50
Liquid paraffin50
Soft paraffin—white500
Ceresine350
 1000

(Poucher, 1932, p. 472)

As well as making the lipstick longer lasting, these dyes fitted with the prevailing idea of the time; that the primary function of a lipstick was to enhance the natural redness of the lips rather than give it an ‘artificial’ colour.

At first, natural dyes were used but these were soon supplemented with, or replaced by, synthetic dyes like eosin – a tetrabromo derivative of fluorescein that had been developed by Heinrich Caro at BASF in Germany in 1874.

Eosine stearate100
Ceresine100
Japan wax200
Lanolin400
Rectified spirit190
Jasmin, No. 105510
 1000

(Poucher, 1932)

Although these dyes made colour last longer on the lips they all suffered from the same problems. Being water-soluble, the lips had to be moistened before the lipstick was applied to enable the water soluble dyes to dissolve so that they could act on the skin of the lips. This was inconvenient, produced uneven results, and sometimes allowed the colour to run beyond the lip-line (feather) causing unsightly stains around the mouth.

One way around these problems was to use a liquid lip rouge instead and these had a reasonable following before the First World War. They consisted mostly of alkaline solutions of cochineal or carmine but there were some that contained the mercury salt merbromin (Mercurochrome). However, being liquids, they were liable to drip and were easy to spill, so when good indelible lipsticks appeared their popularity declined.

Bromo acids

Some time before 1920, water-insoluble fluorescein dyes were developed, the first of which was an acid form of eosin. It was orange in colour but at about a pH of 4 it changed to an intense red salt. Its lack of water-solubility should have meant that it would be used as a pigment – and some lipsticks were made where this was the case – but solvents were found that enabled it to be put into lipstick as a dye. This allowed it to react with the lip tissue to produce a blue-red stain more intense than anything previously generated. In addition, being water-insoluble it worked on dry lips, so many of the previous problems were avoided. Its effectiveness is reflected by the fact that it is still in use today, listed as D&C Red No. 21 or CI 45380.

Other water-insoluble fluorescein dyes followed – none of which were pure red – including dibromofluorescein (D&C Orange No. 5, CI 45370), a yellow-orange stain; tetrachlorobromofluorescein (D&C Red No. 24, CI 45366), a weak-bluish-red stain; and later tetrachlorotetrabromofluorescein (D&C Red No. 27, CI 45410), a strong bluish-red stain. These fluorescein dyes came to be known as bromo acids, a term first coined in the United States (Redgrove, 1935). The first lipsticks that used them were made by dissolving bromo acids in a solvent like stearic acid or acidic coconut oil before combining it with the waxes and other ingredients that made up the lipstick. These sticks stained well but had a tendency to crumble with age (Sagarin, 1957). By the 1930s, an improved lipstick was developed using castor oil as the bromo acid solvent; a practice that I believe also began in the United States.

Castor oil

Castor oil owes its ability to dissolve bromo acids because it is the only natural oil to contain a high content of ricinoleic acid. By modern standards it is not a great solvent for bromo acids but it has other qualities that endeared it to early formulators and it is still the main ingredient in some lipsticks on the market today. Its high viscosity, even when warm, helps delay pigments from settling out and its oily nature helps give the lipstick gloss and emollience.

Allergies and irritations

As the use of bromo acids widened, reports of irritation and allergic reactions increased even though they were still rare. Although little could be done about allergies, it was later discovered that the irritation was mainly due to impurities in the bromo acids. Whatever the cause there appeared to be a clear relationship between the concentration of bromo acids used and the likelihood of irritation, so efforts were made to lower the concentration of the dyes. To offset this, chemists search for other solvents that would dissolve the bromo acids at higher levels than was possible using castor oil. Unfortunately, the chemistry of the day was not sufficiently advanced to achieve this so the problem was not fixed and this may have contributed to the decline in consumer interest in indelibles in the 1940s.

Early alternatives

Not everyone in the 1930s used bromo acids to make indelible lipsticks. Apparently, the chemist Paul Baudecroux used eosin dissolved in propylene glycol to make Rouge Baiser (Appell, 1982), a lipstick he first introduced in France in 1927; if so, he would have been the first to do so commercially. A strong stain was produced with this lipstick as the eosin was in complete solution when it came in contact with the lips. Some said it was too strong! However, as other chemists also discovered, using propylene glycol was not without its problems. As well as having an unpalatable taste, propylene glycol is affected by changes in the atmosphere – losing water when the air was dry and picking it up when the air had a high humidity – with potential effects on the integrity of the lipstick.

Another approach was to mix the eosin-glycol into an emulsion stick, in much the same way that water-based materials are mixed with oils and waxes to make a cream. This produced nice, creamy lipsticks but they had problems similar to those suffered by Rouge Baiser and they did not last long in the marketplace.

Changeable lipsticks

When used in lipsticks, bromo acids were usually combined with pigments but lipsticks were also made where the dyes were the only source of colour. When used alone dyes produced a ‘changeable’ lipstick, an early example of which was first sold by Tangee in 1922. This lipstick looked orange in the stick (due to the eosin) but went red when applied to the lips. In a clever marketing campaign Tangee promoted the lipstick as being ‘natural’ and ran advertisements describing how it would allow the user to avoid looking ‘cheap’ and ‘painted’ and it became the best selling lipstick in the United States between the two world wars.

Unlike ordinary lipsticks
The trouble is, you never suspect yourself of a cheap appearance. Yet any ordinary lipstick hardens your mouth with a painted look. Tangee, however, is unique. Tangee cannot make your lips look painted!
Tangee isn’t paint. It’s different. It even looks different. In the stick, Tangee is orange. Does that mean orange lips, you say? Absolutely no! Put it on. Watch it change colour instantly to the one shade of blush rose perfect for you!

(Tangee advertisement, 1934).

1934-tangee

Above: 1934 Untouched, Painted and Tangee lips.

Tangee gave up on this marketing strategy when it introduced a range of coloured lipsticks after 1941, by which time the idea of using ‘paint’ had lost most of its stigma. However, it did not abandon its changeable lipstick and it is still on sale today.

A second form of changeable lipstick, that was briefly in vogue in the late 1930s, was a black lipstick that changed to red on the lips. The idea seems to have originated with Paul Baudecroux, the chemist responsible for Rouge Baiser. Introduced in 1938, the lipstick contained both oil-soluble and water-soluble dyes but no pigments. The oil-soluble dye – that deNavarre suggests was D&C Red no. 18 (deNavarre, 1975) – gave the sticks a very dark red, almost black colour. As the skin on the lips does not contain enough free oil to be stained by the oil-soluble dye, it did not become lodged on the lips and quickly rubbed off, leaving the water-soluble dye behind which stained the lips red. Moistening the lips before applying the lipstick helped the water-soluble dye to work and produced a better result. The casing of the lipstick appears to have had a twist top to help seal it, presumably to reduce the possibility of it drying out or taking up moisture with changes in the weather.

Rouge Baiser’s Black Lipstick came in six shades (Nasturtium, Light, Medium, Dark, Claret and Orange) with only the deeper shades looking black in the stick. The lipsticks were very expensive – selling for $5.00 in the United States when most lipsticks were $1.00 or less – but cheaper black lipsticks were soon released by makers like Tattoo and Tokalon. After an initial vogue, the novelty factor wore off and the lipsticks faded from the market.

In 1940, Vivaudou produced a green indelible lipstick with a minty fragrance called Viva-Caprice that also turned red on application. It came in two shades (Natural and Brunette) that Vivaudou said “you can’t drink off, smoke off or swim off”. Like the black lipsticks, it was a gimmick that did not last very long.

Pigmented lipsticks

Most lipsticks on the market contain pigments. In general, the difference between a pigmented lipstick that is indelible and one that is not, lies in the amount of bromo acids or other dyes included in the mixture.

When making indelible lipsticks that also contained pigments, formulators had to make the shade that was visible in the lipstick match the shade left on the lips as closely as possible to keep customers happy. In the 1920s this was not a major problem as shade ranges were generally limited and, as yet, it was not the fashion to match lipsticks with clothing or nail polish. Colour matching lipsticks and rouge was considered important, but as these were made with similar pigments it was fairly easy to achieve. As the 1930s progressed it became increasingly fashionable to both match lipsticks with nail polish. This could not be achieved with dyes alone and led to a greater interest in pigmented lipsticks nail and a corresponding decline in indelibles.

See also: Liquid Nail Polish

Indelibility also become less important as women gave up any pretense to using a lipstick that looked natural. The 1940s saw women move to creamier lipsticks that gave a high gloss, a moist appearance, and came in a wide colour range. Colour was heavily promoted by cosmetic companies from the late 1930s all the way up to the Second world War, as was colour coordination, both with clothing and with nail polish.

In the 1950s, in a few short years, Hazel Bishop’s Lasting Lipstick – a pigmented, indelible lipstick – captured of 25% of the American lipstick market beginning wat was known as the ‘lipstick wars’.

Introduced in 1950 – with its ‘Won’t eat-off, bite-off or kiss-off!’ and ‘It stays on you not on him‘ advertising slogans – Hazel Bishop’s Lasting Lipstick ushered in a new wave of indelibles which attempted to overcome the main problem of the creamy lipsticks of the 1940s, namely that they left marks on everything they touched.

Hazel Bishop’s solution to the problem of lipstick marks actually required a good deal of work on the part of the consumer, as a company sponsored publication from 1957 points out.

Here is the correct way to apply lipstick:
1. Make sure your lips are dry, with no traces of old lipstick.
2. With your lipstick or lipstick brush, start your design on the upper lips, moving from the center to the corners of the mouth slowly and surely. Then, in the same way apply lipstick to the lower lip. Many women like to apply the basic design with the lipstick, then fill in corners and round out small curves with a lipstick brush.
3. Check to make sure there are no uncovered areas, including the inside of the lips, so there is no sharp line of demarcation when you smile or talk.
4. Wait a few minutes, without smoking, eating or drinking, for your lipstick to set.
5. Next, to make your Hazel Bishop Long-Lasting Lipstick absolutely smearproof, blot, blot, blot until no more lip print appears on the tissue. Then you can be sure your Hazel Bishop Lipstick won‘t come off on cigarettes, coffee cups, glasses or “him”. It will stay on all day, even all through the night, until you take it off.
6. Glance at your teeth in the mirror to make sure there are no lipstick traces on them.

(Archer, 1957)

See also: Hazel Bishop

Responding to the success of Hazel Bishop many American companies increased the staining power of their lipsticks through the 1950s. These new indelibles included Coty’s Coty 24 (1955) and Revlon’s Indelible-Cream (1951) and Living Lipstick (1955). One formulation that originated in this period was to combine the advantages of using a glycol with those of castor oil by adding polyethylene glycol monoricinoleate which acted as a mutual solvent for both polyethylene glycol and castor oil.

Indelibility claims

In the United States, the rise of no-smear lipsticks in the 1950s attracted the attention of the Federal Trade Commission (FTC) who ruled on the claims being made. In a 1953 letter they deemed that ‘longer lasting’ and ‘less likely to smear’, were appropriate but disallowed the terms ‘indelible’, ‘smear-proof’ and ‘non-smear’ in advertising, unless the word ‘type’ was used with such descriptions. This of course did not apply elsewhere in the world.

Pigment plus stain

The 1950s demand for indelibles in America was largely generated by massive television advertising campaigns. However, unlike the 1930s, increasing the staining power of lipsticks was not going to be enough to ensure sales in the longer term. What women really wanted was the advantages of the creamy lipsticks they had used in the 1940s, with a lipstick that lasted longer on the lips and did not come off on everything their lips touched. Hazel Bishop knew this and strived to increase the adherence of the pigments in her lipsticks as well.

[T]he smear-proof lipstick derives its color from pigment plus stain, rather than from stain alone. This is important because, without pigment, the lip application has a “thin water-colored” look which, in my opinion, is neither satisfactory or desirable to the American women.

(Letter from Hazel Bishop, American Perfumer & Essential Oil Review, 1953)

This has been the picture ever since. Women want a lipstick that is creamy, has a good colour range and stays on their lips. This cannot be achieved by using dyes alone. Although new dyes and solvents were introduced, formulators also worked to find ways to make pigments ‘indelible’ as well. Fortunately, the chemical industry, perhaps stimulated by the war effort, was increasingly able to provide cosmetic chemists with the raw materials to realise this. So, as the 1950s moved into the 1960s, and deeper red colours gave way to corals, pinks and pearlescent shades, pigments not stains would be the dominant lipstick colours and any good quality lipstick became long lasting.

See also: Lipsticks

Updated: 25th September 2014

Sources

Albo, R. (1971). Indelible lipsticks: Some technical aspects. Soap Perfumes & Cosmetics. February, 92-93, 104.

Appell, L. (1982). Cosmetics, fragrances and flavors: Their formulation and preparation with an introduction to the physical aspects of odor and selected syntheses of aromatic chemicals. Whiting, NJ: Novox.

Archer, A. (1957). Your power as a woman: How to develop and use it. New York: Hazel Bishop, Inc.

deNavarre, M. G. (1975). The chemistry and manufacture of cosmetics (2nd. ed., Vol. IV). Orlando: Continental Press.

Fishbach, A. L. (1955). Lipsticks—their formulation, manufacture and analysis. The American Perfumer & Essential Oil Review. March, 31-35.

Hilfer, H. (1951). Indelible lipsticks. The Drug and Cosmetic Industry. 69(3). 314-315, 417.

Jannaway, S. P. (1946). Lipsticks: Part 1. The Perfumery & Essential Oil Record. January, 3-9.

Kalish, J. (1938). Tested formulas for liquid lip rouges. The Drug and Cosmetic Industry. 43(6). 668-669.

Redgrove, H. S. (1935). A note on lipstick manufacture. The Manufacturing Chemist. April, 123-124.

Sagarin, E. (Ed.). (1957). Cosmetics: Science and technology. New York: Interscience Publishers, Inc.