Cosmetic Ingredients PPT

Cosmetic ingredients, their functions and nomenclature TOPIC 3. COSMETIC CHEMISTRY AND Materials Science Dr. Lamees HEJAZI ENTHNS The main legislation/legal act governing the functions and nomenclature of ingredients Commission's decision in 2005 February 9, amendi...

Cosmetic ingredients, their functions and nomenclature TOPIC 3. COSMETIC CHEMISTRY AND Materials Science Dr. Lamees HEJAZI ENTHNS The main legislation/legal act governing the functions and nomenclature of ingredients Commission's decision in 2005 February 9, amending Decision 96/335/EC establishing the inventory and common nomenclature of ingredients used in cosmetic products no. 2006/257/EC (EC 2006) 2019 April 5 Commission Decision (EU) 2019/701, establishing a glossary of common ingredient names used in the labeling of cosmetic products (Text with EEA relevance)- supplementary to above 1. Cosmetic ingredients and their functions Ingredients Latin, Ingredient - a part or component of a mixture. Cosmetic ingredient - a component of a cosmetic product. Each ingredient in a cosmetic product has a certain purpose - a function. Features of the use of ingredients in cosmetic products ABRASIVE BUFFERING MATERIALS ABSORBENT BULK DENSITY REDUCTION LIQUID SUBSTANCE ANTI-CORROSION SUBSTANCES COMPLEXION ANTI-FLAKING Substances CLEANER PREVENTING AGENTS COSMETIC DYE ANTIMICROBIAL AGENTS DENATURANT ANTIOXIDANTS DEODORANT ANTIPERSPIRANTS DEPILATORY ANTI-TARTAR DETANGLER ANTI-GREASE/lipidic SUBSTANCE SOFTENER ANTISTATICS EMULSIFIER EMULSION STABILIZER STABILIZERS FILM Agent BINDERS FOAMING Agent BLEACH FOAMING PROMOTER GELLING Agent HAIR BALM COMPRESSED GAS HAIR DYE REDUCER HAIR FIXATOR LIPID LAYER REDUCING AGENT HAIR CURLING AND COOLER STRAIGHTENING MATERIAL SKIN CONDITIONER MOISTURIZER SKIN PROTECTION AGENT HYDROTROPIC EQUALIZER KERATOLITIC SOLVENT ODOR AND TASTE ABSORBER SOOTHING SUBSTANCE NAIL CONDITIONER STABILIZER OPACIFIER SURFACE TENSION REDUCING SUBSTANCE ORAL CARE MATERIAL SELF-TANNING SUBSTANCE OXIDATING AGENT TONIC PEARL GLOSS UV ABSORBER PLASTICIZER UV FILTER PRESERVATIVE VISCOSITY ADJUSTER All are in the EC 2006 legislation from page 4. 2. Nomenclature of cosmetic ingredients Nomenclature Latin Nomenclature - list of names; a set of names (terms) used in a certain field. INCI (International Nomenclature of Cosmetic Ingredients) Each cosmetic ingredient has its own identification number and name The IUPAC nomenclature is a naming system for chemical compounds created by the International Union of Pure and Applied Chemistry (IUPAC) and first published publicly in 1979. The names of organic chemical compounds in the IUPAC nomenclature consist of numbers and words, numbers are separated from each other by commas, and words are separated by hyphens (e.g. 2,3- dimethylpentane). Each chemical compound has an identifying CAS number assigned to it by the Chemical Abstracts Service (CAS). A short story In 1867 the term "cosmetics" was used for the first time at an international exhibition in Paris to describe perfumery and soap production. The Cosmetic, Toiletry, and Fragrance Association (CTFA) in 1894 , and since 2007 - Personal Care Products Council (PCPC) - US association of cosmetic, toiletry and fragrance manufacturers has published over 15 personal care product directories: 1st - 1973 (5000 ingredients according to the Chemical Abbreviations Service (CAS), 5th - 1994 (6000 ingredients) International Cosmetic Ingredient Dictionary, 11th - 2006 (13000 ingredients) International Nomenclature of Cosmetic Ingredient (INCI), 13th - 2010 (17500 ingredients) International Cosmetic Ingredient Dictionary and Handbook, 15th - 2016 (> 22500 ingredients), from 2019 (> 26500 ingredients)... Basic chemical concepts Element, atom, molecule, compound Physical and chemical properties Physical mixtures Organic and inorganic chemistry SEMINAR Inorganic compounds and their names CLASS COMPOUND NAME Oxides CaO Calcium oxide Peroxides H2O2 Hydrogen peroxide Hydroxides NaOH Sodium hydroxide Acids HCl Hydrochloric acid/hydrogen chloride Salt NaCl Sodium chloride Organic compounds and their names The simplest organic compounds are hydrocarbons. Their molecules consist only of carbon (C) and hydrogen (H) atoms. By replacing H atoms in them with other atoms or their groups (-OH, -COOH, -Cl, etc.), many hydrocarbon derivatives can be obtained - practically all classes of organic compounds. They differ from each other in the number of C atoms in a hydrocarbon chain, by the bond between them (- single, = double, ≡ triple) and can be divided according to the following scheme: Basic rules for forming names of organic compounds Names : In general, the base part of the name reflects the number of carbons assigned in the parent chain. The suffix of the name reflects the type(s) of functional group(s) present on (or within) the parent chain. Other groups which are attached to the parent chain are called substituents. C - always forms 4 chemical bonds OH The complete formula of the compound Abbreviated structural formula The simplest hydrocarbons are ALKANES.  For example: Methane Ethane Propane Butane  Hydrocarbons are further classified into classes based on the functional groups present in their structure. Structural parts of a molecule (groups of several atoms) are called functional groups, which are characteristic only of a certain class of organic compounds and determine the chemical properties of the compound. Functional groups in the hydrocarbon chain can be in different places, one or several, but necessarily preserving the rule of 4 chemical bonds of C atoms. For example: C atoms with H Alkyl Group methylbutane  Alkanes Alkanes - saturated hydrocarbons The names of the straight chain saturated hydrocarbons end with -ane. The names of the substituents formed by the removal of one hydrogen from the end of the chain is obtained by changing the suffix -ane to -yl. 1. Identify the longest carbon chain. This chain is called the parent chain. 2. Identify all of the substituents (groups appending from the parent chain). 3. Number the carbons of the parent chain from the end that gives the substituents the lowest numbers. When comparing a series of numbers, the series that is the "lowest" is the one which contains the lowest number at the occasion of the first difference. If two or more side chains are in equivalent positions, assign the lowest number to the one which will come first in the name. 4. If the same substituent occurs more than once, the location of each point on which the substituent occurs is given. In addition, the number of times the substituent group occurs is indicated by a prefix (di, tri, tetra, etc.). 5. If there are two or more different substituents they are listed in alphabetical order using the base name (ignore the prefixes). The only prefix which is used when putting the substituents in alphabetical order is iso as in isopropyl or isobutyl. The prefixes sec- and tert- are not used in determining alphabetical order except when compared with each other. 6. If chains of equal length are competing for selection as the parent chain, then the choice goes in series to: a) the chain which has the greatest number of side chains. b) the chain whose substituents have the lowest- numbers. c) the chain having the greatest number of carbon atoms in the smaller side chain. d)the chain having the least branched side chains. 7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo- which appears directly in front of Alkyl Group methylbutane Alkyl Halides The halogen is treated as a substituent on an alkane chain. The halo- substituent is considered of equal rank with an alkyl substituent in the numbering of the parent chain Alkenes & Alkynes Alkenes and Alkynes - unsaturated hydrocarbons 1. Double bonds in hydrocarbons indicated by suffix -ene. 2. The carbon atoms of the longest chain are numbered from the side where the double or triple bond is closest. 3. If there is more than one double bond, the suffix is expanded to include a prefix that indicates the number of double bonds present (-adiene, -atriene, etc.). 4. Triple bonds, suffix -yne. The position of the multiple bond(s) within the parent chain is(are) indicated by placing the number(s) of the first carbon of the multiple bond(s) directly in front of the base name. 5. The parent chain is numbered so that the multiple bonds have the lowest numbers (double and triple bonds have priority over alkyl and halo substituents). 6. When both double and triple bonds are present, numbers as low as possible are given to double and triple bonds even though this may at times give "-yne" a lower number than "-ene". When there is a choice in numbering, the double bonds are given the lowest numbers. 7. When both double and triple bonds are present, the -en suffix follows the parent chain directly and the -yne suffix follows the -en suffix (notice that the e is left off, -en instead of -ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the location of the triple bond(s) is(are) indicated between the -en and -yne suffixes. 8. For a branched unsaturated acyclic hydrocarbon, the parent chain is the longest carbon chain that contains the maximum number of double and triple bonds. If there are two or more chains competing for selection as the parent chain (chain with the most multiple bonds), the choice goes to (1) the chain with the greatest number of carbon atoms, (2) the # of carbon atoms being equal, the chain containing the maximum number of double bonds 9. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. Alcohols Alcohols, suffix -anol. If there is more than one hydroxyl group (-OH), the suffix is expanded to include a prefix that indicates the number of hydroxyl groups present (- anediol, -anetriol, etc.). The position of the hydroxyl group(s) on the parent chain is(are) indicated by placing the number(s) corresponding to the location(s) on the parent chain directly in front of the base name (same as alkenes). The hydroxyl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. When both double bonds and hydroxyl groups are present, the -en suffix follows the parent chain directly and the -ol suffix follows the -en suffix (notice that the e is left off, -en instead of -ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the location of the hydroxyl group(s) is(are) indicated between the -en and -ol suffixes. Again, the hydroxyl gets priority in the numbering of the parent chain. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. Examples of names of organic compounds 5 4 3 2 1 3-methylpentane 6 5 4 3 2 1 5-chloro-3-propyl-1-hexanol Ethers You are only expected to know how to name ethers by their common names. The two alkyl groups attached to the oxygen are put in alphabetical order with spaces between the names and they are followed by the word ether. The prefix di- is used if both alkyl groups are the same.  Aldehydes 1. Aldehydes are named by replacing the suffix -ane with -anal. 2. If there is more than one -CHO group, the suffix is expanded to include a prefix that indicates the number of -CHO groups present (-anedial - there should not be more than 2 of these groups on the parent chain as they must occur at the ends). It is not necessary to indicate the position of the -CHO group because this group will be at the end of the parent chain and its carbon is automatically assigned as C-1. 3. The carbonyl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. 4. When both double bonds and carbonyl groups are present, the -en suffix follows the parent chain directly and the -al suffix follows the -en suffix (notice that the e is left off, - en instead of -ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the -al suffix follows the -en suffix directly. Remember it is not necessary to specify the location of the carbonyl group because it will automatically be carbon #1. 5. Again, the carbonyl gets priority in the numbering of the parent chain. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. Ketones 1. Ketones are named by replacing the suffix -ane with -anone. 2. If there is more than one carbonyl group (C=O), the suffix is expanded to include a prefix that indicates the number of carbonyl groups present (-anedione, -anetrione, etc.). The position of the carbonyl group(s) on the parent chain is(are) indicated by placing the number(s) corresponding to the location(s) on the parent chain directly in front of the base name (same as alkenes). 3. The carbonyl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. 4. When both double bonds and carbonyl groups are present, the -en suffix follows the parent chain directly and the -one suffix follows the -en suffix (notice that the e is left off, -en instead of -ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the location of the carbonyl group(s) is(are) indicated between the -en and -one suffixes. 5. Again, the carbonyl gets priority in the numbering of the parent chain. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. Carboxylic Acid 1. Carboxylic acids are named by counting the number of carbons in the longest continuous chain including the carboxyl group and by replacing the suffix -ane of the corresponding alkane with -anoic acid. 2. If there are two -COOH groups, the suffix is expanded to include a prefix that indicates the number of -COOH groups present (-anedioic acid - there should not be more than 2 of these groups on the parent chain as they must occur at the ends). It is not necessary to indicate the position of the -COOH group because this group will be at the end of the parent chain and its carbon is automatically assigned as C-1. 3. The carboxyl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. 4. If the carboxyl group is attached to a ring the parent ring is named and the suffix - carboxylic acid is added. 5. When both double bonds and carboxyl groups are present, the -en suffix follows the parent chain directly and the -oic acid suffix follows the -en suffix (notice that the e is left off, -en instead of -ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the -oic acid suffix follows the -en suffix directly. Remember it is not necessary to specify the location of the carboxyl group because it will automatically be carbon #1. 6. Again, the carboxyl gets priority in the numbering of the parent chain. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference.  3 2 1 3,3-dichloro-propane-carboxylic acid Esters Systematic names of esters are based on the name of the corresponding carboxylic acid. The alkyl group is named like a substituent using the -yl ending. This is followed by a space. The acyl portion of the name (what is left over) is named by replacing the -ic acid suffix of the corresponding carboxylic acid with -ate. Amines You are only expected to know how to name amines by their common names. They are named like ethers, the alkyl (R) groups attached to the nitrogen are put in alphabetical order with no spaces between the names and these are followed by the word amine. The prefixes di- and tri- are used if two or three of the alkyl groups are the same. Sources used Decision of the Commission in 2005 February 9 amending Decision 96/335/EC establishing the inventory and common nomenclature of ingredients used in cosmetic products no. 2006/257/EC: https://eur-lex.europa.eu/eli/dec/ 2006/257/oj Clayden J., Greeves N., Warren S. Organic chemistry 2000.