How do they make lipstick red?

09 Mar.,2024

 

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Pigment, aluminum salt of carminic acid

Carmine ( ) – also called cochineal (when it is extracted from the cochineal insect), cochineal extract, crimson lake, or carmine lake – is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid.[1] Specific code names for the pigment include natural red 4, C.I. 75470, or E120. Carmine is also a general term for a particularly deep-red color.

Etymology

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The English word "carmine" is derived from the French word carmin (12th century), from Medieval Latin carminium, from Persian قرمز qirmiz ("crimson"), which itself derives from Middle Persian carmir ("red, crimson").[2] The Persian term carmir is likely cognate with Sanskrit krimiga ("insect-produced"), from krmi ("worm, insect"). The Persian word for "worm, insect" is kirm, and in Iran (Persia) the red colorant carmine was extracted from the bodies of dead female insects such as Kermes vermilio and cochineal.[3]: 131  The form of the term may also have been influenced in Latin by minium ("red lead, cinnabar"), said to be of Iberian origin.

The word "carmine" has been used as a color name as early as 1799.[4] It is a popular food color, used in yogurt, candy, gelatin, meat, and beverages including fruit juices.[5][6][7]

History

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Female Dactylopius coccus (cochineal) insects were used for their red coloring power as early as 700 BC. South American civilizations crushed the bugs present on cacti to extract the carmine they contain. Carmine pigment was extensively used by the Aztec civilization to dye textiles. It was imported later to Europe during the 16th century.[8]: 255 

Red is a color often associated with power and social status. Through the centuries, red has been worn by tribal chiefs, kings and queens, and military officers.[9]: 166 

Cochineal was a major source of income for the Spanish Crown. By weight, it was a far more valuable commodity than sugar, making it especially lucrative for overseas trade. As part of the triangular trade, its production and consumption were intertwined with slavery.[9]: 64 

In European markets, the Spanish Crown had a monopoly on cochineal until 1820 when the French learned to cultivate them. Later, German and British scientists created a chemical red dye that competed with carmine. The combination of these factors contributed to the end of the Spanish monopoly and considerably lowered the price of carmine, making it accessible to a wider audience.[citation needed]  

Production

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The pigment is produced from carminic acid, which is extracted from some scale insects such as the cochineal scale (Prima), and certain Porphyrophora species (Armenian cochineal and Polish cochineal). Attempts have been made to farm cochineal.

Carmine is a colorant used in the manufacture of artificial flowers, paints, crimson ink, rouge and other cosmetics, and some medications.[10]

Synthetic carminic acid is complex and expensive to produce. Therefore, natural cochineal carmine is predominant on the market. Its instability presents challenges for use in art and textiles, but this is less of a hindrance in the context of cosmetics.[8]: 263 

Preparation

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To prepare carmine, the powdered scale insect bodies are boiled in an ammonia or sodium carbonate solution. After separating the insoluble matter, the extract is treated with alum to precipitate the red solid. This precipitate is called "carmine lake" or "crimson lake". Purity of color is ensured by the absence of iron. Stannous chloride, citric acid, borax, or gelatin may be added to modify the precipitation. The traditional crimson color is affected not only by carminic acid but also by choice of its chelating metal salt ion. For shades of purple, lime is added to the alum.[11][12]

To obtain 1 pound of red dye, 70,000 cochineal insects are required.[9]: 82 

Identification and characteristics

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Carminic acid structure Structure proposed for carmine.

Scientists can detect the presence of carminic acid through liquid chromatography and a diode array detector combined with a mass spectrometer with a quadruple-time-of-flight analyzer (LC-DAD-QTOF). The process is used for identifying carmine in works of art.[9]: 102 

Scientific methods can also distinguish among the different species of cochineal used in artworks.[citation needed]

Wavelength

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As confirmed by reflectance spectroscopy, carmine reflects mostly red light. Its hue ranges from 497 nm for a dark purplish red and 612 nm for a vibrant red.[8]: 264 

Hue

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Carmine's hue is dependent on the metallic ions present in the pigment. For instance, carmine combined with zinc or aluminum yields a crimson hue.[8]: 266 

Translucence

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The translucence of carmine depends on its binding medium. Mixed with oil, carmine remains translucent and adequate for glazes. Combined with tempera or glue, carmine turns opaque.[8]: 264 

Value

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On the Munsell color scale, carmine's value can range between 3.32 and 6.35.[8]: 264 

Permanence

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Carmine is a fugitive color, whose fading is influenced by different factors such as light, humidity, or even the color of the glass of a frame.[13]: 140–152  It is highly sensitive to light and tends to fade into brownish tones.[13]: 141–144 

In painting, its durability depends on the type of binding. For instance, pigments are more stable if mixed with linseed oil rather than with gum arabic.[14]: 1  It is especially sensitive to light in watercolor.[15] Carmine can be stabilized when precipitated with alum and when combined with tin salt mordants.[16]: 698–9 

Notable occurrences in art

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Carmine was used in dyeing textiles and in painting since antiquity. Numerous examples are found among Inca remains such as textile artifacts. The Aztecs also used carmine.

In Europe, the 16th century Italian painter Jacopo Tintoretto used carmine in several of his paintings, the most notable being Portrait of Vincenzo Morosini (1575-80) and Christ Washing the Feet of the Disciples(1575-80).[17][18]

Carmine was also used by nineteenth-century artists such as Vincent van Gogh in Bedroom in Arles (1889). The floor of the bedroom is painted with carmine cochineal lake, geranium lake and indigo. This produced a reddish color, which over time changed to blueish.[19]          

Analysis of J. M. W. Turner's palettes found that he used cochineal carmine.[20] The fading of this pigment affected the appearance of the sky in The Fighting Temeraire (1839).[21]

Other uses

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Architecture

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Sebastien Le Prestre de Vauban, Plan of Lille's Citadelle and harbour

Carmine red has been used in military cartography at least since the 17th century. Sébastien Le Prestre de Vauban, General Engineer of France, recommended the use of this red pigment to represent fortifications (ramparts, wood timbers, and brick buildings being reddish).[22]: 70–71  This made buildings more distinct on maps[23]: 104 

Cosmetics

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Carmine is present in numerous cosmetics because of its red color. This use has continued from antiquity to the present.[9]: 29  It can be found in lipstick, eye shadow, nail polish. It may cause allergies.[24]

Histology

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Carmine can be used in histology, as Best's carmine to stain glycogen, mucicarmine to stain acidic mucopolysaccharides, and carmalum to stain cell nuclei. In these applications, it is applied together with a mordant, usually an Al(III) salt.[citation needed]

Medicine

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Cochineal, the insect used to make carmine, also has medical properties that were exploited by the Aztecs.[9]: 30  It is said to help cure wounds when mixed with vinegar and applied to lesions. Aztecs used it to clean teeth.[citation needed]

Regulations for use in foods

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Extract of carmine was used from the Middle Ages until the 19th century to make crimson dye. Now it is used as a coloring for yogurt and other food products.

United States

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In January 2006, the United States Food and Drug Administration (FDA) evaluated a proposal that would require food products containing carmine to list it by name on the ingredient label.[25] It was also announced that the FDA will separately review the ingredient labels of prescription drugs that contain colorings derived from carmine. A request from the Center for Science in the Public Interest urging the FDA to require ingredient labels to explicitly state that carmine is derived from insects and may cause severe allergic reactions and anaphylactic shock was declined by the FDA.[26][27] Food industries were aggressively opposed to the idea of writing "insect-based" on the label, and the FDA agreed to allow "cochineal extract" or "carmine".[28]

European Union

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In the European Union (EU), the use of carmine in foods is regulated under the European Commission's directives governing food additives in general[29][30] and food dyes in particular[31] and listed under the names Cochineal, Carminic acid, Carmines and Natural Red 4 as additive E 120 in the list of EU-approved food additives.[32] The directive governing food dyes approves the use of carmine for certain groups of foods only[33] and specifies a maximum amount which is permitted or restricts it to the quantum satis.[citation needed]

The EU-Directive 2000/13/EC[34] on food labeling mandates that carmines (like all food additives) must be included in the list of ingredients of a food product with its additive category and listed name or additive number, that is either as Food colour carmines or as Food colour E 120 in the local language(s) of the market(s) the product is sold in.[citation needed]

As of January 2012 , EFSA has changed the way they allow use of Carmine E120 for pharmaceutical products. The EFSA had raised concerns over the increasing number of allergic reactions to carmine derived from insects (E120.360), when used within the British Pharmacopoeia. Pharmaceutical products which had previously contained insect-derived carmine, have been replaced with a synthesized version of the food colorant. Internal studies have shown that the new formulations of popular anti-nausea and weight-gain liquid medication had a significantly lower risk in terms of allergic reactions.[citation needed] The new formulation is known to be of plant origin, using calcium oxide to gauge color depth.[further explanation needed]

References

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Attribution

See also

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Further reading

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  • Carmine as pigment in painting, at ColourLex



MICA



BENEFITS – Natural, Vegan (no animal by-products), Cruelty-Free (not tested on animals), available in a wide range of shades. DISADVANTAGES – Mica pigments are sometimes referred to as “pearl” pigments and always have a sheen, shine or sparkle.

NOTE: Pure Anada Petal Perfect Lipsticks are pigmented with mica. They have a satin, pearly sheen.



– Mica pigments are sometimes referred to as “pearl” pigments and always have a sheen, shine or sparkle.

– Natural, Vegan (no animal by-products), Cruelty-Free (not tested on animals), available in a wide range of shades.

Mica is mined from the earth, and for that reason there is valid concern that it is mined ethically, without the use of child or slave labour. Pure Anada's supplier confirms it pays its workers fairly and even goes so far as providing daycare, medical and schools for the employee and their families. Please request more information if you would like to learn more about this issue.

Cosmetic grade mica is the most common substrate used to pigment “natural” lip colours. The mica mineral is available in a wide variety of shades, the different hues achieved from how the particle is cut (refractive properties), and what it is coated with. Mica pigments are often coated with other minerals such as red and yellow iron oxides or titanium dioxide (white).

Below I will explain in detail the various pigment options available to cosmetic formulators. This will help decipher ingredient lists, and help you make buying decisions based on your values. It will also help you identify counterfeit lists of ingredients. Things that are different, are not the same! So if your lipstick glides on like a dream and feels scarily too much like your former conventional brand, maybe it's too good to be true. Unfortunately.

IRON OXIDES



BENEFITS – Natural, Vegan (no animal by-products), Cruelty-Free (not tested on animals), available in red tones, matte (no shimmer or shine). DISADVANTAGES – The red tones that are achieved from oxides are always WARM, with an orange, earthy undertone. It is impossible to achieve a cool, true, vibrant red with oxides. NOTE: Pure Anada Petal Perfect lipsticks incorporate some iron oxides in the formulation, along with mica to achieve a broader selection of colours.



FD&C DYES







BENEFITS – Vegan, Matte, Vibrant Shades, When mixed with Titanium Dioxide can achieve beautiful nude tones. Anything is possible. DISADVANTAGES – Derived from petroleum. Not natural, or approved in organic formulas. NOTE – Pure Anada cosmetics do not use FD&C dyes in our formulations, however we do produce lip colours for other brands who choose this option.



CARMINE




BENEFITS – Natural, True Red/Pink, Matte DISADVANTAGES – not considered Vegan NOTE – Pure Anada Lavish Lipstick, Exquisite Lip Gloss and Lip & Cheek Rouge all contain Carmine, aside from a few shades within each range, where a pink pigment wasn’t necessary.



PLANT PIGMENTS







BENEFITS – Sounds like an amazing idea! Why isn’t everyone doing it? DISADVANTAGES – Cannot find a supplier for the mysterious “fruit and flower” pigments. NOTE – At this point we do not have the knowledge of, or access to fruit, flower or plant based pigments that function in cosmetics.



TITANIUM DIOXIDE





BENEFITS – Vegan (mineral based), Matte DISADVANTAGES – Only available in white, some controversy over safety NOTE: Pure Anada Petal Perfect lipsticks incorporate mica minerals that are coated with TD, Pure Anada Lavish Lipsticks use TD to lighten the other mineral pigments.



ULTRAMARINES


BENEFITS – Vegan, Matte DISADVANTAGES – Not permitted for use in lips (FDA), Sheer (not a lot of colour pay-off) NOTE – Pure Anada used to incorporate ultramarines in their Petal Perfect lipstick range, but due to formulation challenges - no longer produces these shades.


– Pure Anada used to incorporate ultramarines in their Petal Perfect lipstick range, but due to formulation challenges - no longer produces these shades.

– Not permitted for use in lips (FDA), Sheer (not a lot of colour pay-off)

– Vegan, Matte

Ultramarines are used in mineral makeup and natural cosmetics to offer a vegan and matte alternative to FD&C dyes. They are indispensable to help cool down unwanted warm tones, as a result of using iron oxides to pigment foundations and cheek colours especially. Without the use of Ultramarine Pink in cheek colors, natural mineral makeup would be either very warm (orange-based) due to the iron oxides, or very shiny/luminous, due to the mica. Other alternatives for matte pigments in the pink tones are carmine (not vegan), or FD&C dyes.

Pure Anada Petal Perfect lipsticks incorporate mica minerals that are coated with TD, Pure Anada Lavish Lipsticks use TD to lighten the other mineral pigments.

– Only available in white, some controversy over safety

– Vegan (mineral based), Matte

The TD used in Pure Anada products is approved by COSMOS Ecocert, and has a particle size of approximately 30 microns (NOT nano-sized particles). Titanium Dioxide is used in lipstick formulations to whiten, or lighten the shade. It is also used to coat some mica pigments to give them a light/white hue. You will find titanium dioxide listed on cosmetic labels as CI 77891

It’s also available in different particle sizes. A larger particle size offers a more opaque finish (more coverage). The smaller particle size creates a product that is more translucent. A concern that many scientists have regarding minerals are those which are micronized into nano-sized particles (under 100nm). TD in nano-sized particles is often used in sunscreen products because it applies translucent. There isn’t enough research as to the safety of nano-minerals. Do they absorb into the bloodstream? What happens when they are inhaled? Do they pass through the blood/brain barrier?

Titanium dioxide sounds like a villainous ingredient and I’ve replied to many concerns regarding its safety over the years. It’s an ingredient used in many different industries. TD is used in everything from paint, to candy. There are different grades, ensuring different levels of purity.

Is a bright white mineral which gives makeup “coverage”. Without it, mineral makeup (and most traditional makeup for that matter) would be sheer, with little to no coverage. It has natural sun-blocking properties. The more TD in a formula, the greater sun protection the product has to offer.

– At this point we do not have the knowledge of, or access to fruit, flower or plant based pigments that function in cosmetics.

– Cannot find a supplier for the mysterious “fruit and flower” pigments.

– Sounds like an amazing idea! Why isn’t everyone doing it?

Here’s the scoop – some brands load their formulas with fruit, flower, or plant extracts and put a marketing emphasis on these ingredients, leading consumers to believe it is these ingredients that are creating the pigmentation. Some brands even state – pigmented with fruit and flower extracts. To my knowledge thereis no such thing. This is misleading. Especially if they do not list the pigments they are ACTUALLY using to colour their product.

Then there are fruit and flower EXTRACTS or WAXES. These are beautiful additions to formulas, but they do not provide any color.

There is one company who produces oil soluable plant pigments which they call microzests. When I first heard of them years ago I was SO excited! Finally, I could pigment lipstick with “microzest” from rose or bamboo. I sampled them, and unfortunately, they were a tremendous disappointment. The pigments were sheer, with virtually no color pay-off, and weren’t at all what we had hoped.

In a nutshell, there ARE colorants available which are derived from plant sources: annatto and beta carotene for example. They are drab, dull, and not light-stable. Furthermore, the majority of them are only water soluble. For lip colors, one needs a pigment that is soluble in OIL. An extract of Alkenet Root can be made to be dispersed into oil-based products - but there isn't bold payoff.

To give myself some credibility in this matter, I will briefly share some of my experience. I’ve been crafting makeup for 12 years. Not only do we manufacture cosmetics for our own brand (Pure Anada), but we also manufacture for other brands. Several of these brands are respected and well-known in their territory. Some even have organic certification status. Together, along with the product development managers of these brands, we have scoured the globe to find plant pigments to use in their products. We have communicated with technical departments of the lead cosmetic pigment suppliers in the world.

“Why don’t you just use fruit, vegetable or flower pigment to colour your products?” I am asked this question regularly. I will be the first to admit that I have not learned everything there is to know about formulating colour cosmetics. However, I do feel I have researched and scoured the globe for these elusive 100% pure fruit and vegetable pigments to use in cosmetics.

– Pure Anada Lavish Lipstick, Exquisite Lip Gloss and Lip & Cheek Rouge all contain Carmine, aside from a few shades within each range, where a pink pigment wasn’t necessary.

– not considered Vegan

– Natural, True Red/Pink, Matte

You will find carmine listed on the ingredient label as: CI 75470. Certain varieties are approved by Ecocert to be used in COSMOS certified organic products.

The catch…it’s a pigment derived from crushed beetles (cochineal). However it’s also approved for use in food and you’ve probably ingested it several times in your life when drinking a “naturally” coloured beverage. (Fruitopia for example).

This natural pigment has the ability to produce a true pink hue that is matte. On its own, it’s a fairly vibrant cool-toned red. Mixed with other iron oxides and titanium dioxide, it is possible to achieve a variety of lovely shades.

– Pure Anada cosmetics do not use FD&C dyes in our formulations, however we do produce lip colours for other brands who choose this option.

– Derived from petroleum. Not natural, or approved in organic formulas.

– Vegan, Matte, Vibrant Shades, When mixed with Titanium Dioxide can achieve beautiful nude tones. Anything is possible.

The infinite array of colours that can be achieved using FD&C dyes would be very appealing to makeup artists who need a large selection of shades, but don’t want to use a completely synthetic formula. It fills a niche market of consumers who want to make a better choice, but aren’t complete purists. FD&C Dyes will be listed on the ingredient list as a wide variety of CI (colour index) numbers.

I question brands who somehow achieve vibrant, cool and/or matte shades with apparently just the use of minerals. I know it’s impossible, so there has to be a link of miss-information either from their manufacturer (since MOST makeup brands do not produce their own product), OR they are knowingly being dishonest.

Some brands opt for using FD&C dyes in lip colours, in a base made from healthy plant oils and waxes. These brands have become popular in the “green beauty” circles because they can rival the shades of the big brands people are used to using. I personally respect that these brands are honest and disclose that they DO use dyes to achieve their colours.

This is the largest stumbling block to brands and consumers. What they want is the shades that can be achieved with FD&C dyes, but unfortunately it cannot be claimed as “all natural”. FD&C dyes are NOT approved for use in certified organic cosmetics (COSMOS Ecocert, USDA, etc). Ironically, these dyes are sometimes referred to by pigment manufacturers as “organic” dyes because they are derived from petroleum (living matter), even though they aren’t organic as far as we would typically classify other organic ingredients such as plant oils and waxes with USDA certification (for example). Minerals on the other hand, are referred to as “inorganic” pigments because they are non-living.

FD&C dyes are the ONLY way it is possible to achieve vibrant, colour-rich, vegan, matte pigments in cosmetics in a wide variety of hues. It’s possible to achieve vibrant hues with mica – but it won’t be matte. It’s possible to achieve matte with iron oxides – but it won’t be vibrant. It’s possible to achieve cool matte tones with carmine – but it won’t be vegan.

FD&C stand for Food, Drug and Cosmetic. While these colorants are derived from petro-chemicals, they are the most regulated of all pigments worldwide. Over the years, these dyes have caused controversy due to severe adverse reactions. Many have been banned and others restricted for use. We are now left with 12 FD&C dyes, which are approved for use in food in the USA, however many more are approved for use in just cosmetics.

: Pure Anada Petal Perfect lipsticks incorporate some iron oxides in the formulation, along with mica to achieve a broader selection of colours.

– The red tones that are achieved from oxides are always WARM, with an orange, earthy undertone. It is impossible to achieve a cool, true, vibrant red with oxides.

– Natural, Vegan (no animal by-products), Cruelty-Free (not tested on animals), available in red tones, matte (no shimmer or shine).

In lipsticks, red oxides are the only way to produce a red shade that is both NATURAL and VEGAN. You will find iron oxides listed on cosmetic labels as - CI 77489, CI 77491, CI 77492, CI 77499

Iron oxides are iron salts. They are available in various WARM shades of yellow, red and umber.There is also a black iron oxide, that when mixed with yellow and red can create a plethora of beige and brown shades. Iron oxides, combined with Titanium Dioxide are the minerals responsible to create the various shades of foundation for skin tones ranging from pale porcelain to deep ebony black. Iron Oxides are also used to coat mica minerals (see above).

Lipsticks are one of the most difficult products to formulate with natural ingredients. Eco-savvy consumers want their lipstick to perform like their favourite conventional brand: vibrant shades, bold colour, and long-lasting. But they also want it to be vegan and free from everything "synthetic". It's a bold request that puts a lot of cosmetic manufacturers and the brands they produce for - under a lot of pressure to perform! For that reason, sometimes when it comes to eco-friendly lip colours, not everything is as it seems. Due to my experience over the last number of years, I sometimes come across ingredient lists for lip colours that don't match up with the brand's impressive range of colours. Before you become enraged, keep in mind that approximately 98% of makeup brands do not produce their own products. They hire contract manufacturers who may or may not be honest with their clients about what's REALLY making their lipstick red (or pink).

How do they make lipstick red?

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