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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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Volume 88, Issue 10-11

Issues

Source-based nomenclature for single-strand homopolymers and copolymers (IUPAC Recommendations 2016)

Richard G. Jones
  • Corresponding author
  • Functional Materials Group, School of Physical Sciences, University of Kent, Canterbury CT2 7NH, UK
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/ Tatsuki Kitayama
  • Corresponding author
  • Department of Chemistry, Graduate School of Engineering, Osaka University, Toyonaka, Osaka 560-8531, Japan
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/ Karl-Heinz Hellwich / Michael Hess
  • FB-8, Makromolekulare Chemie, Universität Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany
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/ Aubrey D. Jenkins / Jaroslav Kahovec
  • Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovsky Sq. 2, CZ 162 06 Praha 6, Czech Republic
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/ Pavel Kratochvíl
  • Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovsky Sq. 2, CZ 162 06 Praha 6, Czech Republic
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/ Itaru Mita / Werner Mormann
  • FB-8, Makromolekulare Chemie, Universität Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, Germany
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/ Christopher K. Ober
  • Department of Materials Science and Engineering, Cornell University, 310, Bard Hall, Ithaca, NY, USA
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/ Stanisław Penczek
  • Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódz, Poland
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/ Robert F. T. Stepto / Kevin Thurlow
  • Chemical Nomenclature Advisory Service, LGC Ltd., Queens Road, Teddington, Middlesex TW11 0LY, UK
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/ Jiří Vohlídal
  • Functional Materials Group, School of Physical Sciences, University of Kent, Canterbury CT2 7NH, UK
  • Faculty of Science, Charles University in Prague, Albertov 2030, CZ-128 40 Praha 2, Czech Republic
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/ Edward S. Wilks
  • Functional Materials Group, School of Physical Sciences, University of Kent, Canterbury CT2 7NH, UK
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Published Online: 2016-11-26 | DOI: https://doi.org/10.1515/pac-2015-0702

Abstract

IUPAC recommendations on source-based nomenclature for single-strand polymers have so far addressed its application mainly to copolymers, non-linear polymers and polymer assemblies, and within generic source-based nomenclature of polymers. In this document, rules are formulated for devising a satisfactory source-based name for a polymer, whether homopolymer or copolymer, which are as clear and rigorous as possible. Thus, the source-based system for naming polymers is presented in a totality that serves as a user-friendly alternative to the structure-based system of polymer nomenclature. In addition, because of their widespread and established use, recommendations for the use of traditional names of polymers are also elaborated.

Keywords: apparent monomer; copolymer; end-groups; homopolymer; IUPAC; IUPAC nomenclature; monomer; nomenclature; polymers; polymer nomenclature; source-based names; traditional names

Dedicated to: The memory of Robert (Bob) Stepto, former president of the Polymer Division of IUPAC, whose recent death denied him the satisfaction of witnessing the publication of this manuscript on which he expended much effort.

Article note:

Sponsoring bodies: IUPAC Division of Chemical Nomenclature and Structure Representation and IUPAC Polymer Division, Sub-Committee on Polymer Terminology: see more details on p. 1098.

SB-0 Introduction

A polymer can be named in one of two principal ways by using either the ‘source-based’ or the ‘structure-based’ systems of nomenclature. Source-based nomenclature does not contain information on the structure of the polymer it names. To draw a polymer structure from a source-based name, knowledge of the chemistry of the polymerization process is required. Structure-based nomenclature is in many cases more complicated but allows the drawing of the polymer structure directly from the name without requiring knowledge of the chemistry involved in the polymer formation.

The general principle that systematic chemical nomenclature should reflect the real structure of compounds to be named is fulfilled in the case of organic polymers through the use of structure-based nomenclature, in which the strict rules of IUPAC organic-chemical nomenclature are adapted to the naming of the constitutional units of a polymer. Under the auspices of either the former Commission on Macromolecular Nomenclature or the present day Division of Chemical Nomenclature and Structure Representation, IUPAC has published four documents [1], [2], [3], [4] on structure-based nomenclature which enable the naming of most organic polymers. Typically, regardless of how it might have been formed, a polymer known to comprise constitutional repeating units with the formula –CH(C6H5)CH2– would be named poly(1-phenylethylene) or, alternatively, poly(1-phenylethane-1,2-diyl). However, despite the rigour afforded by the structure-based system, over many years scientists in both industry and academia have continued to use the source-based system of polymer nomenclature and still favour it for being familiar, simpler to apply, and, for most purposes, more immediately comprehensible (see Appendix SB-7). Under the source-based system, the above structure would probably have been prepared (sourced) from the monomer styrene and is therefore named polystyrene. As a consequence of the continuing use of this system of polymer nomenclature, the present day IUPAC Polymer Division and the Division of Chemical Nomenclature and Structure Representation accepted it as an alternative official nomenclature system for polymers. However, although the former Commission produced documents on the source-based nomenclature of linear copolymers [5], the source-based nomenclature of non-linear polymers and polymer assemblies [6], and generic source-based polymer nomenclature [7], to date there has been no document that formalises in any detail the source-based nomenclature of single-strand (linear) homopolymers.

In this document, rules for generating source-based names of single-strand polymers are elaborated and, since the system has commonly used names for monomers that are no longer retained in IUPAC nomenclature, guidelines for the use of traditional polymer names are presented. In order that rules for all single-strand polymers are collected together in a single document, the content of the recommendations on ‘Source-Based Nomenclature for Copolymers’ [5] is updated and included here.

Though the IUPAC recommendations for ‘Source-Based Nomenclature for Non-Linear Macromolecules and Macromolecular Assemblies’ [6], which describe non-linear polymer structures (branched, crosslinked, etc.) and polymer assemblies, are given better foundation by the content of the present document, they are not included here. Generic source-based polymer nomenclature is also not addressed and the earlier recommendations, ‘Generic Source-Based Nomenclature for Polymers’ [7], should be viewed as dealing with some additional issues not covered herein. However, Refs. [6, 7] should only be used as if they were revised according to recommendations in the current document and Ref. [8].

In the present document, terminology is used much of which derives from usage in the IUPAC ‘Blue Book’, the ‘Nomenclature of Organic Chemistry’ [8]. The relevant terms and their meanings are as follows:

Preferred IUPAC name (PIN)

A name preferred among two or more names generated from two or more IUPAC recommendations including the many synonyms that have been coined and used over the years.

General IUPAC nomenclature

The principles, rules, and conventions by which IUPAC names other than preferred IUPAC names (PINs) are generated.

Traditional name

A name in common use within one or more sectors of the chemical community.

Retained name

A traditional name or a name in common use either as the preferred IUPAC name or as an alternative name in general IUPAC nomenclature.

SB-1 Glossary

Some of the terms defined in this section are extractions of the essence of primary definitions in Refs. [9, 10]. This is done for the sake of brevity and to avoid subjecting the reader to tedious cross referencing. All such instances are indicated. These definitions are not to be taken as new primary definitions.

Cross references to terms defined elsewhere in this section are denoted in italic typeface.

SB-1.1 apparent monomer

Monomer which from the name of a polymer appears to have been used in the synthesis of the latter when it has actually been prepared from different precursor(s). See also Section SB-2.1.1.

  • Note:

    The term replaces both of the formerly used terms ‘hypothetical monomer’ and ‘implicit monomer’ [5], [9], [10], which are now deemed to be obsolete.

SB-1.2 block

Portion of a macromolecule, comprising many constitutional units, that has at least one constitutional or configurational feature which is not present in the adjacent portions [9], [10].

  • Note:

    Where appropriate, definitions relating to macromolecule may also be applied to block.

SB-1.3 block polymer

Polymer composed of block macromolecules [9], [10].

SB-1.4 chain

Whole or part of a macromolecule, an oligomer molecule, or a block, comprising a linear or branched sequence of constitutional units between two boundary constitutional units, each of which may be either an end-group, a branch point, or an otherwise-designated characteristic feature of the macromolecule [9], [10].

  • Note 1:

    Except in linear single-strand macromolecules, the definition of a chain may be somewhat arbitrary.

  • Note 2:

    A cyclic macromolecule has no end-groups but may nevertheless be regarded as a chain.

  • Note 3:

    Any number of branch points may be present between the boundary units.

  • Note 4:

    Where appropriate, definitions relating to macromolecule may also be applied to chain.

SB-1.4.1 main chain

That linear chain to which all other chains, long or short or both, may be regarded as being pendant [9], [10].

SB-1.4.2 side chain

Oligomeric or polymeric offshoot from a macromolecular chain [9], [10].

SB-1.5 chain polymerization

Chain reaction [10] in which the growth of a macromolecular chain proceeds exclusively by reaction(s) between monomer molecule(s) and active site(s) on the macromolecular chain with regeneration of the active site(s) at the end of each growth step [11].

  • Note 1:

    A chain polymerization consists of chain initiation and chain propagation reactions, and may also include chain deactivation or chain transfer reactions, or both.

  • Note 2:

    The adjective ‘chain’ in ‘chain polymerization’ denotes ‘chain reaction’ rather than a ‘macromolecular chain’.

  • Note 3:

    Propagation in chain polymerization usually occurs without the formation of small molecules. However, cases exist where a low-molar-mass by-product is formed, as in the polymerization of oxazolidine-2,5-diones derived from amino acids (termed N-carboxyamino acid anhydrides). When a low-molar-mass by-product is formed, the additional adjective condensative is recommended to form the term ‘condensative chain polymerization’.

  • Note 4:

    The growth steps are expressed by Px+M→Px+1 (+L) x ∈ {1, 2,... ∞} where Px denotes the growing chain of degree of polymerization x, M a monomer, and L a low-molar-mass by-product formed in the case of condensative chain polymerization.

  • Note 5:

    The term ‘chain polymerization’ may be qualified further, if necessary, to specify the type of chemical reactions involved in the growth step, e.g. ring-opening chain polymerization, cationic chain polymerization.

  • Note 6:

    There exist, exceptionally, some polymerizations that proceed via chain reactions that, according to the definition, are not chain polymerizations. For example, the polymerization

HS–X–SH + H2C=CH–Y–CH=CH2(–S–X–S–CH2–CH2–Y–CH2–CH2–)n

proceeds via a radical chain reaction with intermolecular transfer of the radical center.

The growth step in such polymerizations involves reactions between molecules of all degrees of polymerization and, hence, they are classified as polyadditions. If required, the classification can be made more precise and the polymerizations described as chain-reaction polyadditions.

  • Note 7:

    Adapted from the definition in [11].

SB-1.6 constitutional unit

Atom or group of atoms (with pendant atoms or groups, if any) comprising a part of the essential structure of a macromolecule, an oligomer molecule, a block or a chain [9], [10].

SB-1.7 constitutional repeating unit (CRU)

Smallest constitutional unit, the repetition of which constitutes a regular macromolecule, a regular oligomer molecule, a regular block or a regular chain [9], [10].

SB-1.8 copolymer

Polymer derived from more than one species of monomer or apparent monomer.

  • Note 1:

    Copolymers that are obtained by copolymerization of two monomer species are sometimes termed bipolymers, those obtained from three monomers terpolymers, those obtained from four monomers quaterpolymers, etc.

  • Note 2:

    Adapted from the definition in [9], [10].

SB-1.8.1 alternating copolymer

Copolymer consisting of macromolecules comprising two species of monomeric units in alternating sequence.

  • Note 1:

    An alternating copolymer may be considered as a homopolymer derived from an apparent monomer.

  • Note 2:

    Adapted from the definition in [9], [10].

SB-1.8.2 block copolymer

Copolymer that is a block polymer [9], [10].

  • Note:

    In the constituent macromolecules of a block copolymer, adjacent blocks are constitutionally different, i.e. adjacent blocks comprise constitutional units derived from different species of monomer or from the same species of monomer but with a different composition or sequence distribution of constitutional units.

SB-1.8.3 graft copolymer

Copolymer that is a graft polymer [9], [10].

  • Note:

    In the constituent macromolecules of a graft copolymer, adjacent blocks in the main chain or side-chains, or both, are constitutionally different, i.e. adjacent blocks comprise constitutional units derived from different species of monomer or from the same species of monomer but with a different composition or sequence distribution of constitutional units.

SB-1.8.4 periodic copolymer

Copolymer consisting of macromolecules comprising more than two species of monomeric units in regular sequence [9], [10].

SB-1.8.5 random copolymer

Copolymer consisting of macromolecules in which the probability of finding a given monomeric unit at any given site in the chain is independent of the nature of the adjacent units [9], [10].

  • Note:

    In a random copolymer, the sequence distribution of monomeric units follows Bernoullian statistics.

SB-1.8.6 statistical copolymer

Copolymer consisting of macromolecules in which the sequential distribution of the monomeric units obeys known statistical laws [9], [10].

  • Note:

    An example of a statistical copolymer is one consisting of macromolecules in which the sequential distribution of monomeric units follows Markovian statistics.

SB-1.9 end group

Constitutional unit that is an extremity of a macromolecule or oligomer molecule [9], [10].

SB-1.10 graft polymer

Polymer composed of graft macromolecules, i.e. macromolecules with one or more species of block connected to the main chain as side chains, these side chains having constitutional or configurational features that differ from those in the main chain.

See also graft homopolymer.

  • Note:

    Combination of definitions 1.28 (graft macromolecule) and 2.23 (graft polymer) in [9].

SB-1.11 homopolymer

Polymer derived from one species of a real monomer or an apparent monomer.

  • Note:

    Adapted from the definition in [9], [10].

SB-1.11.1 block homopolymer

Homopolymer that is composed of macromolecules comprising blocks that have at least one constitutional or configurational feature which is not present in the adjacent portions.

SB-1.11.2 graft homopolymer

Homopolymer composed of macromolecules with one or more species of block connected to the main chain as side chains, these side chains having constitutional or configurational features that differ from those in the main chain.

SB-1.12 irregular polymer

Polymer composed of irregular macromolecules, i.e. macromolecules the structures of which essentially comprise the repetition of more than one type of constitutional unit, or macromolecules the structures of which comprise constitutional units not all connected identically with respect to directional sense.

  • Note:

    Combination of definitions 1.5 (irregular macromolecule) and 2.16 (irregular polymer) in [9].

SB-1.13 locant

Numeral or letter that identifies position in a structure [1].

  • Note:

    A locant appears in a name or general expression such as ‘2-substituted’.

SB-1.14 macromolecule

Molecule of high relative molecular mass, the structure of which essentially comprises the multiple repetition of units derived, actually or conceptually, from molecules of low relative molecular mass [9], [10].

SB-1.14.1 regular macromolecule

Macromolecule, the structure of which essentially comprises the repetition of a single constitutional unit with all units connected identically with respect to directional sense [9], [10].

SB-1.15 monomer

Substance composed of monomer molecules [9], [10].

SB-1.16 monomeric unit

Largest constitutional unit contributed by a single monomer molecule to the structure of a macromolecule or oligomer molecule [9], [10].

  • Note:

    The largest constitutional unit contributed by a single monomer molecule to the structure of a macromolecule or oligomer molecule may be described as either monomeric, or by ‘monomer’ used adjectivally.

SB-1.17 monomer molecule

Molecule which contributes constitutional units to the essential structure of a macromolecule.

  • Note:

    Corrected from [9], [10] in which the definition implies that a single molecule can undergo polymerization.

SB-1.18 oligomer molecule

Molecule of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass [9], [10].

  • Note 1:

    A molecule is regarded as having an intermediate relative molecular mass if it has properties which do vary significantly with the removal of one or a few of the units.

  • Note 2:

    If a part or the whole of the molecule has an intermediate relative molecular mass and essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass, it may be described as oligomeric, or by ‘oligomer’ used adjectivally.

SB-1.19 polyaddition

Polymerization in which the growth of polymer chains proceeds by addition reactions between molecules of all degrees of polymerization [9], [10].

SB-1.20 polycondensation

Polymerization in which the growth of polymer chains proceeds by condensation reactions between molecules of all degrees of polymerization [9], [10].

SB-1.21 polymer

Substance composed of macromolecules [9], [10].

SB-1.22 regular polymer

Polymer composed of regular macromolecules, regular star macromolecules or regular comb macromolecules [9], [10].

SB-1.23 ring-opening polymerization

Polymerization in which a cyclic monomer yields a monomeric unit which is acyclic or contains fewer cycles than the monomer [9], [10].

  • Note:

    If the monomer is polycyclic, the opening of a single ring is sufficient to classify the reaction as a ring-opening polymerization.

SB-1.24 single-strand polymer

Polymer, the macromolecules of which are single-strand macromolecules, i.e.macromolecules comprising constitutional units connected in such a way that adjacent constitutional units are joined to each other through two atoms, one on each constitutional unit [1].

  • Note:

    Combination of definitions 1.39 (single-strand macromolecule) and 2.29 (single-strand polymer) in [9].

SB-1.25 stereodescriptor

Prefix to specify configuration (absolute or relative) or conformation.

  • Note:

    Typical examples are R, S; r, s; P, M; Re, Si; E, Z; ap, sp; t, g+, g-, d, l [12].

SB-2 Source-based names of homopolymers

SB-2.1 Monomer names

Rule 1

The monomer names recommended for use in the source-based nomenclature of polymers shall be systematic names or retained trivial names presently recommended by the IUPAC rules of organic and inorganic nomenclature [8], [13].

  • Note 1:

    Where there are alternative names, unless otherwise indicated in Appendix SB-7, it is recommended that the preferred IUPAC name (PIN) is used. A typical exception is styrene which is used in preference to the PIN, ethenylbenzene.

  • Note 2:

    There is a limited number of commonly encountered inorganic monomers. Within source-based polymer nomenclature it is recommended that these are named in accordance with the IUPAC rules of inorganic nomenclature [13] but where there are alternative names it is proposed that the one closer to organic-chemical usage is used.

Examples

1.1
styrene
vinylbenzene
ethenylbenzene (PIN)
1.2
methyl acrylate
methyl prop-2-enoate (PIN)
1.3
methyl acetate
ethenyl acetate (PIN)
1.4
azepan-2-one (PIN)
hexane-6-lactam
1.5
1,1′-(dimethylsilanediyl)ferrocene

SB-2.1.1 Apparent monomers

Sometimes the structure of a polymer makes it appear that it might have been made by the polymerization of a monomer which has either not been used or might not even exist. Such a monomer is known as an apparent monomer (see SB-1.1). For example, poly(vinyl alcohol) has a repeating unit which suggests that it is the polymerization product of the monomer vinyl alcohol [14], the unstable enolic tautomer of acetaldehyde depicted in Example 1.6. However, the monomer normally used in the preparation of this polymer is vinyl acetate that polymerizes to poly(vinyl acetate), after which hydrolysis gives poly(vinyl alcohol). A similar though contrasting situation applies to poly[N,N′-(hexane-1,6-diyl)adipamide], i.e. nylon 6,6, which might be considered to result from the polymerization of a cyclic monomer called N,N′-(hexane-1,6-diyl)adipamide (Example 1.7). Another such instance is that of poly(ethylene terephthalate), which appears to be the polymerization product of a monomer, ethylene terephthalate (Example 1.8). Likewise, the condensation polymer prepared from 1,4-dichlorobenzene and sodium sulfide is named poly(1,4-phenylene sulfide), apparently being derived from a non-existent monomer, 1,4-phenylene sulfide (Example 1.9).

Examples

1.6
vinyl alcohol
1.7
N,N′-(hexane-1,6-diyl)adipamide
1,8-diazacyclotetradecane-2,7-dione
1.8
ethylene terephthalate
1.9
1,4-phenylene sulfide

SB-2.2 Source-based names of homopolymers formed by chain polymerization, ring-opening polymerization or polyaddition

Rule 2

The source-based name of a homopolymer formed by chain polymerization, ring-opening polymerization or polyaddition is made by prefixing the monomer name with ‘poly’. The name of the monomer is parenthesized if it consists of more than one word (e.g. acrylic acid), includes prefixes expressing substituents (e.g. chloroethene), one or more locants or stereodescriptors (e.g. but-1-ene), or if ambiguity in meaning might arise.

  • Note 1:

    Ambiguity can in most cases arise if the monomer name starts with a part or prefix that can be multiplied to produce a different monomer, e.g. poly(chlorostyrene) is a polymer whereas polychlorostyrene might be a multi-substituted styrene monomer. Similarly the polymer poly(oxetane) is distinguished from the class name polyoxetane which applies to four-membered rings with more than one oxygen atom.

  • Note 2:

    Depending on the polymerization conditions, a single monomer may give rise to two or more polymer structures, as in the case of buta-1,3-diene. In this instance, it is possible to induce the polymerization to proceed almost exclusively by 1,4- or 1,2- addition of the monomer to the growing chain. Both products are regular homopolymers, but with different repeating units. However, under different polymerization conditions, combinations of the 1,4- and 1,2- modes of polymerization lead to irregular homopolymers. Accordingly, in instances such as these in which a certain monomer can contribute two or more types of constitutional unit to the polymer structure, the nominal distinction between the different products is made by using generic source-based nomenclature [7] or structure-based nomenclature [3].

  • Note 3:

    When a cyclic monomer is an oligomer (dimer, trimer, etc.) of a smaller monomer, then the constitutional repeating unit will be deemed to be derived from the smaller monomer. For example, the monomer 1,3,5-trioxane is a cyclic trimer of formaldehyde, so the polymer derived from it is named polyformaldehyde and not poly(1,3,5-trioxane).

  • Note 4:

    The specification of quantitative properties of a polymer, such as relative molecular mass, degree of polymerization, or, in the case of copolymers, composition, is not usually incorporated in a polymer name but if relevant may be added afterwards in parentheses. Thus, for example, one can write ‘polystyrene (Mr,n=30 200)’ (see Ref. [15], p. 49) to indicate a polymer of styrene with a number-average relative molecular mass of 30 200. For full details, the reader is referred to Section 8 in Ref. [5].

Examples

2.1
polyethene
2.2
polypropene
2.3
polyacrylonitrile
2.4
poly(vinyl alcohol)
2.5
poly(buta-1,3-diene)
  • Note:

    The preferred graphic representation of the polymer is with the double bond in the 1-position (lowest possible locant for unsaturation), i.e. that which corresponds to the structure-based name poly(but-1-ene-1,4-diyl) [1], [16].

2.6
polystyrene
2.7
poly(3-methylstyrene)
2.8
poly(isopropenylbenzene)
2.9
poly(methyl methacrylate)
2.10
poly(9-vinyl-9H-carbazole)
2.11
poly(oxirane)
2.12
polyformaldehyde
2.13
poly(oxetan-2-one)
2.14
poly(4-isocyanatobutan-1-ol)
  • Note:

    While the name given for Example 2.14 is correct, the polymer, notionally the product of a one-monomer polyaddition, can only be formed using protecting-group chemistry. The monomer indicated is thereby an apparent monomer. The more familiar products of two-monomer polyaddition reactions are classified as alternating copolymers. Their nomenclature is covered in Section SB-3.2 and typified in Example 3.12.

SB-2.3 Source-based names of polymers formed by polycondensation

There are two distinct types of polycondensation: polycondensation of a single monomer, denoted by x-A-y, and that of a pair of monomers, x-A-x and y-B-y, where x and y are mutually-reactive functional groups. For example, x might be a hydroxy, alkoxy, amino, or alkylamino group, while y might be a carboxy or carboxylate group. In order that the source-based nomenclature of their polymers is as far as possible consistent with the principles elaborated in the foregoing sections, it is recommended that both types of polycondensation use the apparent monomer approach.

Rule 3

The source-based name of the homopolymeric product of a polycondensation is made by prefixing the apparent monomer name with ‘poly’. In accordance with the guidance of Rule 2, the name of the apparent monomer is parenthesized if it consists of more than one word, includes one or more substituent prefixes, locants or stereodescriptors, or if ambiguity in meaning can arise.

  • Note 1:

    In some instances of polycondensation of a single monomer denoted by x-A-y the custom has been to derive the name of the polymer in accordance with Rule 2, i.e. from the name of a monomer rather than from that of an apparent monomer, polyalanine (Example 2.15) and poly(lactic acid) (Example 2.16) being such instances. This is the preferred practice as long as the monomer name is retained within IUPAC nomenclature [8], [13].

  • Note 2:

    In the case of the polycondensation of two monomers, a particular polymer structure might be synthesised from more than just one pair of monomers. For example, poly(ethylene terephthalate) can be prepared by the reaction of ethane-1,2-diol (or oxirane), x-A-x, and terephthalic acid (or its derivatives, such as esters or halides), y-B-y. According to Rule 5 (see Section SB-3.2) the name of the polymer could be poly[oxirane-alt-(terephthalic acid)] or poly[(ethylene glycol)-alt-(terephthaloyl dichloride)]; other names are also possible, depending on the particular selection of the two monomers. Many of these polycondensations are indeed met in practice, in contrast to the rather rare cases of the self-condensation of different single monomers to give the same polymer. The fact that a given polymer, with a particular structure, can have many different source-based names could lead to confusion, so names of the type poly(A-alt-B) are not acceptable except in the very rare instances that an apparent monomer cannot be named.

Examples

2.15
polyalanine
poly(2-aminopropanoic acid)
poly(3-methylaziridin-2-one)
2.16
poly(lactic acid)
poly(2-hydroxypropanoic acid
poly(3-methyloxiran-2-one)
2.17
poly(oxolan-2-one)
poly(4-hydroxybutanoic acid)
2.18
poly(azepan-2-one)
poly(6-aminohexanoic acid)
2.19
poly(hexane-1,6-diyl adipate)
2.20
poly(ethylene terephthalate)
2.21
poly[N,N′-(propane-1,3-diyl)isophthalamide]
2.22
poly[N,N′-(hexane-1,6-diyl)hexanediamide]
poly[N,N′-(hexane-1,6-diyl)adipamide]
2.23
poly[(dimethylmethylene)bis (4,1-phenylene) carbonate]

SB-3 Source-based names of copolymers

There are three types of source-based names for copolymers, depending on the sequential arrangement of the monomeric units [5]:

  1. copolymers with an unspecified sequential arrangement of monomeric units;

  2. linear copolymers with random, statistical, alternating, or periodic distributions of monomeric units;

  3. block and graft polymers.

SB-3.1 Copolymers with an unspecified sequential arrangement of monomeric units

Rule 4

If the sequential arrangement of monomeric units in a copolymer is not known, the source-based name of the copolymer is made by combining the prefix ‘poly’ and, in parentheses, the monomer or apparent monomer names (A, B, etc.), in alphabetical order, separated by the italicized connective -co-.

Examples

3.1
poly(ethene-co-propene)
3.2
poly(acrylonitrile-co-styrene)
3.3
poly[(methyl methacrylate)-co-styrene]
3.4
poly[(isopropenylbenzene)-co-(methyl methacrylate)]
3.5
poly[(buta-1,3-diene)-co- (2-chlorobuta-1,3-diene)]
  • Note:

    Concerning the graphic representation, see the note to Example 2.5.

3.6
poly[(ethylene isophthalate)-co-(ethylene terephthalate)]
3.7
poly[(butane-1,4-diyl terephthalate)-co-(ethylene terephthalate)]

SB-3.2 Random, statistical, alternating and periodic copolymers

Rule 5

If the sequential arrangement of monomeric units in a copolymer is known to be random, statistical, alternating, or periodic, the source-based name of the copolymer is made by combining the prefix ‘poly’ and, in parentheses, the monomer or apparent monomer names (A, B, etc.), separated by the italicized connectives -ran-, -stat-, -alt-, or -per-, respectively. The order of citation of the monomer names should be alphabetical except in the case of periodic copolymers for which it must agree with the sequence distribution of monomeric units in the copolymer.

  • Note 1:

    The source-based names of random, statistical, alternating and periodic copolymers would typically be represented as poly(A-ran-B), poly(A-stat-B), poly(A-alt-B) and poly(A-per-B-per-C).

  • Note 2:

    The adjective ‘periodic’ should not be used for copolymers consisting of only two types of alternating monomeric units; these should be treated as alternating copolymers.

  • Note 3:

    A random copolymer is a special case of a statistical copolymer in which the probability of finding a given monomeric unit at any given site in the chain is independent of the nature of the neighbouring units at that position (Bernoullian distribution).

  • Note 4:

    The alternative nomenclature for copolymers, outlined in the Appendix of Ref. [5] which gave rise to such names as alt-copoly(A/B), has long been abandoned and is no longer acceptable.

Examples

3.8
poly[ethene-ran-(vinyl acetate)]
3.9
poly[(isopropenylbenzene)-stat-styrene]
3.10
poly[(maleic anhydride)-alt-styrene]
3.11
poly(oxirane-per-oxirane-per-formaldehyde)
3.12
poly[(1,4-diisocyanatobenzene)-alt-(hexane-1,6-diol)]

Rule 6

If copolymer structures comprise several types of periodicity, some of which are always characterized by the sequencing of particular monomer units (A, B, …), and others of which are always characterized by the sequencing of two or more other monomer units (U, V, …) in irregular arrangement, the polymers are considered as extended alternating or periodic copolymers. The source-based name of the copolymer should lead with the monomer that appears earliest in alphabetical order. Thereafter, within their respective groups the order of citation of the other monomers should be alphabetical. Unless there is only a single name, the names within the groups are embraced by parentheses and separated by semicolon(s) without spaces.

  • Note:

    The following illustrate some typical representations:

poly[A-alt-(U;V)]-AUAVAVAUAVAUAU-
poly[(A;B)-alt-U]-AUBUAUAUAUBUAUBU-
poly[(A;B)-alt-(U;V)]-AVAVBUAUBUBVBUAVBU-
poly[A-per-B-per-(U;V)]-ABUABUABVABUABVABVABU-
poly[A-per-(U;V)-per-B-per-(U;V)]-AUAUBVBUAVBVBUBVAUBUAUAV-

Example

3.13

poly[(isopropenylbenzene;styrene)-alt-(maleic anhydride)]
3.14

poly{[(diethyl fumarate);(maleic anhydride)]-alt-(isopropenylbenzene;styrene)}

SB-3.3 Block polymers

The names of block polymers differ from the names of the copolymers described in SB-3.1 and SB-3.2. Every block is named as if it were an individual polymer, i.e. polyA, polyB, etc. for a homopolymer block, or poly(A-co-B), etc. for a copolymer block; the name of the block copolymer is then made by arranging the names of the blocks in the appropriate order separated by the italicized connective, -block-.

Rule 7

A block polymer or copolymer consisting of several blocks is named by arranging the names of the blocks, separated by the connective -block-, in the order of their sequence in the copolymer chain, but when two or more blocks are repeated in the same sequence two or more times in a polymer chain the name should be shortened by using the appropriate prefix – bis, tris, tetrakis, etc. The order of citation of the monomer names should be alphabetical except in cases where the sequence distribution of monomeric units in the copolymer dictates otherwise.

  • Note 1:

    Both sides of the connective -block- must be attached to the names of the blocks (polyA, polyB, etc.) and not to the names of the monomers. Thus, the following names are wrong: poly[(methyl methacrylate)-block-styrene] and poly[(buta-1,3-diene)-block-styrene-block-(buta-1,3-diene-stat-styrene)]; the correct names are given in examples 3.15 and 3.19 respectively.

  • Note 2:

    The following illustrate typical representations:

    polyA-block-polyB(a di-block copolymer)
    bis(polyA-block-polyB)(a tetra-block copolymer of alternating blocks)
    poly(polyA-block-polyB)(a multi-block copolymer of alternating blocks)
    poly(A-stat-B)-block-polyA-block-polyB(a tri-block copolymer in which one of the blocks is a statistical copolymer)

  • Note 3:

    Tris(polyA-block-polyB) is a shorter representation of polyA-block-polyB-block-polyA-block- polyB-block-polyA-block-polyB, and bis(polyA-block-polyB-block-polyC) of polyA-block-polyB- block-polyC-block-polyA-block-polyB-block-polyC.

  • Note 4:

    For short blocks the prefix ‘oligo’ may be used in place of ‘poly’.

  • Note 5:

    For blocks of a defined length a numerical prefix should be used in place of ‘poly’.

  • Note 6:

    Retained traditional polymer names as defined in Section SB-5 are allowed for blocks.

  • Note 7:

    The alternative nomenclature for block copolymers, outlined in the Appendix of Ref. [5] which gave rise to such names as block-copoly(A/B), has long been abandoned and its use is no longer acceptable.

Examples

3.15
poly(methyl methacrylate)-block-polystyrene
3.16
polystyrene-block-poly(methyl methacrylate)-block-polystyrene
3.17

bis[poly(buta-1,3-diene)-block-polystyrene]1
  • Note:

    This is a shorter representation of poly(buta-1,3-diene)-block-polystyrene-block-poly(buta-1,3-diene)-block-polystyrene.

3.18
poly{poly[methyl(phenyl)silane]-block-poly(oxirane)}
3.19

poly(buta-1,3-diene)-block-polystyrene-block-poly(buta-1,3-diene-stat-styrene)1

Rule 8

A block polymer or copolymer in which the blocks are connected through a link unit, X, is named by arranging the names of the blocks, in alphabetical order, separated by the compound connective -block-X-block- in which X is named as a constitutional unit [1] in accordance with IUPAC nomenclature rules [8], [13], [16].

Examples

3.20

poly(methyl methacrylate)-block-(1,1-dimethyl-2-oxoethylene)oxyethyleneoxy-block-poly[methyl(phenyl)silane]
3.21

poly(chloroethene)-block-(dimethylsilanediyl)-block-poly(oxirane)

SB-3.4 Graft polymers

Rule 9

The names of graft homopolymers and copolymers are formed by citing the name(s) of the main-chain polymer or block(s), followed by the connective -graft-, and then the name of the side chain; this order of citation is important. If two or more different chains are randomly grafted onto the main chain, semicolons without spaces are used to separate the names of the grafts and the totality of the names of the side chains is parenthesized (cf. Rule 6). If the numbers of graft chains per molecule are known then they are named using prefixes (bis, tris, etc.).

  • Note 1:

    The following illustrate typical representations:

    polyA-graft-polyU

    poly(A-co-B)-graft-polyU

    poly(A-alt-B)-graft-polyU

    (polyA-block-polyB)-graft-(polyU-block-polyV)(a graft copolymer in which the chains of one block copolymer are grafted onto unspecified main-chain blocks of another)
    polyA-graft-(polyU;polyV)(a graft copolymer in which polyU and polyV chains are grafted to a main chain)
    (polyA-graft-polyU)-block-(polyB-graft-polyV)(a diblock copolymer in which polyU chains are grafted to one block and polyV chains to the other)
    (polyA-block-polyB-block-polyC)-graft-polyU(a graft copolymer in which polyU chains are grafted at unspecified main-chain blocks)
    polyA-block-[polyB-graft-polyU]-block-polyC(a graft copolymer in which polyU chains are grafted at main-chain block polyB)
    polyA-tris(graft-polyB)(a graft copolymer in which three polyB chains are grafted to a main-chain polyA)

  • Note 2:

    For short blocks or grafts the prefix ‘oligo’ may be used in place of ‘poly’.

  • Note 3:

    For blocks or grafts of a defined length a numerical prefix should be used in place of ‘poly’.

  • Note 4:

    Retained traditional polymer names as defined in Section SB-5 are allowed for blocks and grafts.

Examples

3.22

polyethylene-graft-poly(butyl acrylate)
3.23

poly(methyl methacrylate)-graft-[poly(dimethylsiloxane);poly(oxirane)]
3.24

poly(methyl methacrylate)-graft-{poly(dimethylsiloxane)-block-[poly(methyl methacrylate)-graft-poly(oxirane)]}
3.25

poly(buta-1,3-diene)-tris(graft-polystyrene) 2
  • Note:

    In the above graphical representation, the horizontal line indicates grafting at unknown positions in the main-chain units.

Rule 10

A graft homopolymer or copolymer in which the main-chain blocks are connected through a link unit, X, to which a graft, polyY, is attached is named by arranging the names of the blocks, separated by the compound connective -block-(X-graft-polyY)-block- in which X is named as a constitutional unit [1] in accordance with the IUPAC Rules of Organic or Inorganic Nomenclature [8], [13], [16].

Example

3.26

deca(buta-1,3-diene)-block-[(methylsilanetriyl)-graft-polystyrene]-block-pentadeca(buta-1,3-diene)3

SB-4 Naming end-groups

Rule 11

When the end groups of a polymer are to be specified, the name of the polymer is preceded by the systematic names of the end groups prefixed by α and ω, typically as α-X-ω-YpolyA.

  • Note 1:

    In general, the source-based naming of a polymer with end groups takes no account of the orientation of the monomeric units in the polymer chain and therefore no specification of which end group is at the beginning of the chain and which at the end of the chain. If, however, the mechanism of the polymer formation is known and the graphical representation of the structure [17] depicts the correct orientation of the monomeric unit then, in many instances, it will be clear as to which end group is better associated with α and which with ω.

  • Note 2:

    For those polymers in which the structures of the monomeric units and end groups allow for the reversal of the orientation of the monomeric unit, the chosen orientation is that for which the end groups can be cited in alphabetical order.

Examples

4.1
α-hydro-ω-butylpoly(3,5-dimethylstyrene)
4.2
α-hydro-ω-methoxypoly(oxirane)
[not α-methyl-ω-hydroxypoly(oxirane)]
4.3
α,ω-bis(benzoyloxy)poly(9-vinyl-9H-carbazole)

SB-5 Traditional names of homopolymers

Because of their widespread use within industry and academia, a limited number of well-established traditional names of homopolymers are retained (see Appendix SB-7). In most cases these were derived from now obsolete names of their corresponding monomers. If the monomer names are not retained in IUPAC nomenclature it is no longer acceptable to use them regardless of the prevalence of their appearance in scientific, technical and commercial literature. Thus, even though retained traditional polymer names based on obsolete monomer names have every appearance of being source-based polymer names they are no longer so. Traditional polymer names which are not retained should be replaced by their proper source-based (or structure-based) polymer names as IUPAC nomenclature becomes used more widely in polymer science. Appendix SB-7 contains a comprehensive listing of which the following are some of the more important examples:

Examples

Retained traditional polymer nameSource-based name
5.1 polyethylenepolyethene
5.2 polypropylenepolypropene
5.3 polyisobutenepoly(2-methylpropene)
5.4 polytetrafluoroethylenepoly(tetrafluoroethene)
  • Note 1:

    In general, a traditional name of a polymer is a source-based name if it is based on a retained IUPAC name of the monomer. In such an instance, the name is listed in column 1 in Appendix SB-7.

  • Note 2:

    Notwithstanding the retention of the corresponding monomer name in IUPAC nomenclature, some traditional polymer names are not retained and are no longer acceptable, for example, poly(ethylene glycol).

  • Note 3:

    In some instances for which the monomer name is not retained in organic or inorganic nomenclature, neither is the traditional polymer name. Typically, polybutylene, for which the corresponding monomer is but-1-ene, has the obsolete name butylene, which is not retained in IUPAC nomenclature, being easily confused with butane-1,4-diyl.

Rule 12

The retained traditional polymer names as listed in Appendix SB-7 are also retained for use as components in block and graft polymer names and the names of modified polymers [18].

SB-6 Summary

SB-6.1 General

  1. Source-based nomenclature of single-strand polymers is an accepted IUPAC nomenclature. It is a convenient alternative to structure-based nomenclature.

  2. IUPAC uses the general term ‘preferred IUPAC name’ (PIN) to recommend a single name from amongst several possible variants for a given monomer. This approach helps to remove one of the shortcomings of source-based nomenclature by reducing the number of names used for a given polymer when rigour is essential.

SB-6.2 Naming homopolymers made by chain polymerization, ring-opening polymerization or polyaddition

  1. The names of the monomers to be used in source-based nomenclature should conform to the IUPAC recommendations concerning organic and inorganic chemical nomenclature.

  2. The concept of an apparent monomer is introduced.

  3. In developing source-based names of homopolymers formed by chain polymerization, ring-opening polymerization, or polyaddition, the monomer names following ‘poly’ should be parenthesized for those with substituents, locants, or stereodescriptors, and for names consisting of two or more words.

SB-6.3 Polymers made by polycondensation

For the polycondensation products of a single monomer of the type x-A-y or of two monomers of the types x-A-x and y-B-y, a name based on an apparent monomer such as (cyclic) ethylene terephthalate is recommended.

SB-6.4 Copolymers

  1. The source-based names of copolymers with an unspecified distribution of monomeric units are based on names of the monomers or apparent monomers separated by the connective -co-.

  2. The names of linear copolymers with random, statistical, alternating, or periodic distributions of monomeric units are based on the names of the monomers separated by the connectives -ran-, -stat-, -alt-, and -per-, respectively.

  3. The names of block and graft polymers (homopolymers and copolymers) are based on the homopolymer names separated by the connectives -block- or -graft-, respectively.

  4. The nomenclature for graft polymers allows for the naming of polymers with graft chains distributed onto all types or selected types of constitutional units of the main chain.

  5. The formerly used nomenclature system using the prefix ‘copoly’ for copolymers has been abandoned and is no longer acceptable.

SB-6.5 Naming end groups

A method for the inclusion of end-group names where required is elaborated.

SB-6.6 Traditional polymer names

Because of their widespread use within industry and academia, a limited number of well-established traditional names of homopolymers are retained for use with, or in place of, source-based or structure-based names.

SB-7 Appendix

Source-based, structure-based and traditional names of common polymers

Entries are listed in the alphabetical order of alternative source-based names except for those instances where there are preferred names (those indicated in bold typeface) which are always listed first.

Memberships of sponsoring bodies

Membership of the IUPAC Division of Chemical Nomenclature and Structure Representation for the period 2014–2015 is as follows:

President: K.-H. Hellwich (Germany); Secretary: T. Damhus (Denmark); Past President: R. M. Hartshorn (New Zealand); Titular Members: M. A. Beckett (UK); P. Hodge (UK); A. T. Hutton (South Africa); R. S. Laitinen (Finland); E. Nordlander (Sweden); A. P. Rauter (Portugal); H. Rey (Germany); Associate Members: K. Degtyarenko (Spain); Md. A. Hashem (Bangladesh); M. M. Rogers (USA); J. B. Todd (USA); J. Vohlídal (Czech Republic); A. Yerin (Russia); National Representatives: V. Ahsen (Turkey); D. J. Choo (Republic of Korea); G. A. Eller (Austria); W. Huang (China); T. L. Lowary (Canada); J. Nagy (Hungary); M. Putala (Slovakia); S. Tangpitayakul (Thailand); L. Varga-Defterdarović (Croatia); Ex Officio: G. P. Moss (UK).

Membership of the IUPAC Polymer Division Committee for the period 2014–2015 is as follows: President: M. Buback (Germany); Vice President: G. T. Russell (New Zealand); Secretary: M. Hess (Germany); Past President: C. K. Ober (USA); Titular Members: S. Beuermann (Germany); B. Charleux (France); J. He (China); R. C. Hiorns (France); G. Moad (Australia); W. Mormann (Germany); M. Sawamoto (Japan); Associate Members: D. Dijkstra (Germany); R. Hutchinson (Canada); I. Lacík (Slovakia); T. Long (USA); D. W. Smith (USA); Y. Yagci (Turkey); National Representatives: T. Dingemans (Netherlands); C. dos Santos (Brazil); C.-C. Han (Malaysia); V. P. Hoven (Thailand); C.-S. Hsu (Taiwan); R. G. Jones (UK); D. S. Lee (Korea); A. M. Muzafarov (Russia); M. Siddiq (Pakistan); J. Vohlídal (Czech Republic).

Membership of the Subcommittee on Polymer Terminology (until 2005, the Subcommittee on Macromolecular Terminology) for the period 2003–2015 was as follows: Chair: M. Hess (Germany), until 2005; R. G. Jones (UK), 2006–2013; R. C. Hiorns (France), from 2014; Secretary: R. G. Jones (UK), until 2005; M. Hess (Germany) 2006–2007; T. Kitayama (Japan), 2008–2009; R. C. Hiorns (France), 2010–2013; C. K. Luscombe (USA), 2014–2015; Members: R. Adhikari (Nepal); G. Allegra (Italy); M. Barón (Argentina); R. Boucher (UK); T. Chang (Korea); J. Chen (USA); A. Fradet (France); K. Hatada (Japan); J. He (China); K.-H. Hellwich (Germany); M. Hess (Germany); R. C. Hiorns (France); P. Hodge (UK); K. Horie4 (Japan); A. D. Jenkins (UK); J.-I. Jin (Korea); R. G. Jones (UK); J. Kahovec (Czech Republic); T. Kitayama (Japan); P. Kratochvíl (Czech Republic); P. Kubisa (Poland); C. K. Luscombe (USA); E. Maréchal (France); S. V. Meille (Italy); I. Meisel (Germany); W. V. Metanomski4 (USA); I. Mita4 (Japan); G. Moad (Australia); W. Mormann (Germany); N. Nakabayashi (Japan); T. Nakano (Japan), C. K. Ober (USA); S. Penczek (Poland); M. D. Purbrick (UK); L. P. Rebelo (Portugal); M. Rinaudo (France); G. Russell (USA); C. dos Santos (Brazil); I. Schopov (Bulgaria); C. Scholz (USA); F. Schué4 (France); V. P. Shibaev (Russia); S. Slomkowski (Poland); D. W. Smith (USA), R. F. T. Stepto4 (UK); N. Stingelin (UK); D. Tabak (Brazil); J.-P. Vairon (France); M. Vert (France); J. Vohlídal (Czech Republic); M. G. Walter (USA); E. S. Wilks (USA); W. J. Work (USA).

This manuscript (PAC-REC-15-07-02) was prepared in the framework of IUPAC project 2003-042-1-800.

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Note:

Republication or reproduction of this report or its storage and/or dissemination by electronic means is permitted without the need for formal IUPAC or De Gruyter permission on condition that an acknowledgment, with full reference to the source, along with use of the copyright symbol ©, the name IUPAC, the name De Gruyter, and the year of publication, are prominently visible. Publication of a translation into another language is subject to the additional condition of prior approval from the relevant IUPAC National Adhering Organization and De Gruyter.

Footnotes

  • 1

    The preferred graphical representation of butadiene units in poly(buta-1,3-diene) corresponds to the structure-based name poly(but-1-ene-1,4-diyl) [[1], [17]], i.e. with the double bond in the 1-position rather than the 2-position. 

  • 2

    See footnote to Example 3.17 

  • 3

    See footnote to Example 3.17 

  • 4

    Deceased. 

About the article

Deceased


Received: 2015-07-10

Accepted: 2016-06-27

Published Online: 2016-11-26

Published in Print: 2016-11-01


Citation Information: Pure and Applied Chemistry, Volume 88, Issue 10-11, Pages 1073–1100, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2015-0702.

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