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A brief guide to polymer nomenclature (IUPAC Technical Report)

TL;DR: The universal adoption of an agreed nomenclature has never been more important for the description of chemical structures in publishing and online searching as mentioned in this paper, and the International Union of Pure and Applied Chemistry (IUPAC) and Chemical Abstracts Service (CAS) make similar recommendations.
Abstract: The universal adoption of an agreed nomenclature has never been more important for the description of chemical structures in publishing and online searching. The International Union of Pure and Applied Chemistry (IUPAC) and Chemical Abstracts Service (CAS) make similar recommendations. The main points are shown here with references to original documents. Further details can be found in the IUPAC Purple Book.

Summary (2 min read)

1) Introduction

  • The universal adoption of an agreed nomenclature has never been more important for the description of chemical structures in publishing and online searching.
  • The International Union of Pure and Applied Chemistry 1a,b and Chemical Abstracts Service (CAS)2 make similar recommendations.
  • The main points are shown here with hyperlinks to original documents.
  • Further details can be found in the IUPAC Purple Book.3.

2) Basic Concepts

  • The terms polymer and macromolecule do not mean the same thing.
  • The latter usually have a range of molar masses (unit g mol–1), the distributions of which are indicated by dispersity (Đ).
  • Alternatively, more explicit structure-based nomenclature can be used when the polymer structure is proven.
  • Where there is no confusion, some traditional names are also acceptable.

3.1 Homopolymers

  • A homopolymer is named using the name of the real or assumed monomer (the ‘source’) from which it is derived, e.g., poly(methyl methacrylate).
  • Monomers can be named using IUPAC recommendations, or well-established traditional names.
  • Should ambiguity arise, class names can be added.6.
  • The source-based name poly could correspond to either of the structures shown below.
  • Thus on the left and right, respectively, are polyalkylene:vinyloxirane and polyether: vinyloxirane.

4.1 Regular single-strand organic polymers8

  • In place of the monomer name used in source-based nomenclature, structure-based nomenclature uses that of the preferred constitutional repeating unit (CRU).
  • It can be determined as follows: (i) a large enough part of the polymer chain is drawn to show the structural repetition, e.g., (ii) the smallest repeating portion is a CRU, so all such possibilities are identified.

A brief guide to polymer nomenclature (IUPAC Technical Report)

  • ‡E-mail: polymer.nomenclature@iupac.org; Sponsoring body: IUPAC Polymer Division, Subcommittee on Polymer Terminology.
  • In the above example, the oxy subunits in the CRUs are heteroatom chains.
  • The preferred CRU is therefore oxy(1-bromoethane-1,2-diyl) and the polymer is thus named poly[oxy(1-bromoethane-1,2-diyl)].
  • Please note the enclosing marks around the subunit carrying the substituent.

4.2 Regular double-strand organic polymers10

  • Double-strand polymers consist of uninterrupted chains of rings.
  • In a spiro polymer, each ring has one atom in common with adjacent rings.
  • To identify the preferred CRU, the chain is broken so that the senior ring is retained with the maximum number of heteroatoms and the minimum number of free valences.
  • It is oriented so that the lower left atom has the lowest number.
  • The free-valence locants are written before the suffix, and they are cited clockwise from the lower left position as: lower-left, upper-left:upper-right, lowerright.

5) Nomenclature of Inorganic and Inorganic–Organic Polymers11

  • Some regular single-strand inorganic polymers can be named like organic polymers using the rules given above, e.g., [O-Si(CH3)2]n and [Sn(CH3)2]n are named poly[oxy] and poly, respectively.
  • Inorganic polymers can also be named in accordance with inorganic nomenclature, but it should be noted that the seniority of the elements is different to that in organic nomenclature.
  • Certain inorganic–organic polymers, for example those containing metallocene derivatives, are at present best named using organic nomenclature, e.g., the polymer on the left can be named poly[(dimethyl - silanediyl)ferrocene-1,1'-diyl].

7) Graphical Representations12,13

  • The bonds between atoms can be omitted, but dashes should be drawn for chain-ends.
  • The seniority of the subunits does not need to be followed.
  • For single-strand (co)polymers, a dash is drawn through the enclosing marks, e.g., poly[oxy(ethane-1,2-diyl)] shown below left.
  • For irregular polymers, the CUs are separated by slashes, and the dashes are drawn inside the enclosing marks.
  • End-groups are connected using additional dashes outside of the enclosing marks, e.g., α-methyl-ω-hydroxy-poly[oxirane-co], shown below right.

8) CA Index Names2

  • In the CAS system, the CRU is called a structural repeating unit (SRU).
  • There are minor differences in the placements of locants, e.g., poly(pyridine-3,5-diylthiophene-2,5-diyl) is poly(3,5-pyridinediyl-2,5-thiophenediyl) in the CAS registry, but otherwise polymers are named using similar methods to those of IUPAC.

R. C. HIORNS et al.2168

  • Republication or reproduction of this report or its storage and/or dissemination by electronic means is permitted without the need for formal IUPAC permission on condition that an acknowledgment, with full reference to the source, along with use of the copyright symbol ©, the name IUPAC, 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.

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A brief guide to polymer nomenclature (IUPAC
Technical Report)
Roger C. Hiorns, R.J. Boucher, R. Duhlev, K.-H. Hellwich, P. Hodge, A.D.
Jenkins, R.G. Jones, J. Kahovec, G. Moad, C.K. Ober, et al.
To cite this version:
Roger C. Hiorns, R.J. Boucher, R. Duhlev, K.-H. Hellwich, P. Hodge, et al.. A brief guide to polymer
nomenclature (IUPAC Technical Report). Pure and Applied Chemistry, De Gruyter, 2012, 84 (10),
pp.2167-2169. �10.1351/PAC-REP-12-03-05�. �hal-01601985�

1) Introduction
The universal adoption of an agreed nomenclature has never been more
important for the description of chemical structures in publishing and on-
line searching. The International Union of Pure and Applied Chemistry
(IUPAC)
1a,b
and Chemical Abstracts Service (CAS)
2
make similar recom-
mendations. The main points are shown here with hyperlinks to original
documents. Further details can be found in the IUPAC Purple Book.
3
2) Basic Concepts
The terms polymer and macromolecule do not mean the same thing. A
polymer is a substance composed of macromolecules. The latter usually
have a range of molar masses (unit g mol
–1
), the distributions of which are
indicated by dispersity (
Đ
). It is defined as the ratio of the mass-average
molar mass (M
m
) to the number-average molar mass (M
n
) i.e. (
Đ
) =
M
m
/M
n
.
4
Symbols for physical quantities or variables are in italic font but
those representing units or labels are in roman font.
Polymer nomenclature usually applies to idealised representations; minor
structural irregularities are ignored. A polymer can be named in one of two
ways. Source-based nomenclature can be used when the monomer can be
identified. Alternatively, more explicit structure-based nomenclature can
be used when the polymer structure is proven. Where there is no confusion,
some traditional names are also acceptable.
Whatever method is used, all polymer names have the prefix poly, followed
by enclosing marks around the rest of the name. The marks are used in the
order: {[( )]}. Locants indicate the position of structural features, e.g.,
poly(4-chlorostyrene). If a source-based name is one word and has no
locants, then the enclosing marks are not essential, but they should be used
when there might be confusion, e.g., poly(chlorostyrene) is a polymer
whereas polychlorostyrene might be a small, multi-substituted molecule.
End-groups are described with α- and ω-, e.g., α-chloro-ω-hydroxy-poly-
styrene.
3
3) Source-Based Nomenclature
5
3.1 Homopolymers
A homopolymer is named using the name of the real or assumed monomer
(the ‘source’) from which it is derived, e.g., poly(methyl methacrylate).
Monomers can be named using IUPAC recommendations, or well-estab-
lished traditional names. Should ambiguity arise, class names can be
added.
6
For example, the source-based name poly(vinyloxirane) could cor-
respond to either of the structures shown below. To clarify, the polymer is
named using the polymer class
name followed by a colon and the
name of the monomer, i.e., class
name:monomer name. Thus on the
left and right, respectively, are polyalkylene:vinyloxirane and polyether:
vinyloxirane.
3.2 Copolymers
7
The structure of a copolymer can be described using the most appropriate
of the connectives shown in Table 1. These are written in italic font.
3.3 Non-linear polymers
5
Non-linear polymers and copolymers, and polymer assemblies are named
using the italicized qualifiers in Table 2. The qualifier, such as branch, is
used as a prefix (P) when naming a (co)polymer, or as a connective (C),
e.g., comb, between two polymer names.
4) Structure-Based Nomenclature
4.1 Regular single-strand organic polymers
8
In place of the monomer name used in source-based nomenclature, struc-
ture-based nomenclature uses that of the preferred constitutional repeating
unit (CRU). It can be determined as follows: (i) a large enough part of the
polymer chain is drawn to show the structural repetition, e.g.,
(ii) the smallest repeating portion is a CRU, so all such possibilities are
identified. In this case:
(iii) the next step is to identify the subunits that make up each of these
structures, i.e., the largest divalent groups that can be named using IUPAC
nomenclature of organic compounds such as the examples that are listed in
Table 3; (iv) using the shortest path from the most senior subunit to the next
senior, the correct order of the subunits is determined using Fig. 1; (v) the
preferred CRU is chosen as that with the lowest possible locant(s) for sub-
stituents.
Pure Appl. Chem.
, Vol. 84, No. 10, pp. 2167–2169, 2012.
http://dx.doi.org/10.1351/PAC-REP-12-03-05
© 2012 IUPAC, Publication date (Web): 3 October 2012 (Version 1.0)
2167
1
Freely available on: (a) http://www.iupac.org/publications/pac/;
(b) http://www.chem.qmul.ac.uk/iupac/
2
http://www.cas.org/
3
IUPAC. The “Purple Book”, RSC Publishing, Cambridge, UK
(2008).
4
IUPAC. Pure Appl. Chem. 81, 351 (2009).
5
IUPAC. Pure Appl. Chem. 69, 2511 (1997).
6
IUPAC. Pure Appl. Chem. 73, 1511 (2001).
7
IUPAC. Pure Appl. Chem. 57, 1427 (1985).
8
IUPAC. Pure Appl. Chem. 74, 1921 (2002).
A brief guide to polymer nomenclature (IUPAC Technical Report)
R. C. Hiorns (France)
, R. J. Boucher (UK), R. Duhlev (UK), K.-H. Hellwich (Germany), P. Hodge (UK), A. D. Jenkins (UK), R. G. Jones (UK),
J. Kahovec (Czech Republic), G. Moad (Australia), C. K. Ober (USA), D. W. Smith (USA), R. F. T. Stepto (UK), J.-P. Vairon (France), and J. Vohlídal
(Czech Republic).
E-mail: polymer.nomenclature@iupac.org; Sponsoring body: IUPAC Polymer Division, Subcommittee on Polymer Terminology.
Table 1 Qualifiers for copolymers.
7
unspecified co (C) poly(styrene-co-isoprene)
statistical stat (C) poly[isoprene-stat-(methyl methacrylate)]
random ra
n (C)
poly[(methyl methacrylate)-ran-(butyl acrylate)]
alternating alt (C) poly[styrene-alt-(maleic anhydride)]
periodic per (C) poly[styrene-per-isoprene-per-(4-vin
ylp
yridine)]
block block (C)
poly(buta-1,3-diene)-block-poly(ethene-co-propene)
graft
a
graft (C) polystyrene-graft-poly(ethylene oxide)
a
The first name is that of the main chain.
Table 2 Qualifiers for non-linear (co)polymers and polymer assemblies.
5
blend blend (C) poly(3-hexylthiophene)-blend-
polystyrene
comb comb (C) polystyrene-comb-polyisoprene
complex compl (C) poly(2,3-dihydrothieno[3,4-b]
[1,4]dioxine)-compl-
poly(vin
ylbenzenesulfonic acid)
a
cyclic cyclo (P) cyclo-polystyrene-graft-polyethylene
branch branc
h (P) branch-poly[(1,4-divinylbenzene)-
stat-styrene]
network net (C or P) net-poly(phenol-co-formaldehyde)
interpenetrating network ipn (C) (net-polystyrene)-ipn-
[net-poly(methyl acrylate)]
semi-interpenetrating sipn (C) (net-polystyrene)-sipn-polyisoprene
network
star star (P) star-polyisoprene
a
In accordance with IUPAC organic nomenclature, square brackets enclose locants
that refer to the numbering of the components of the fused ring.
To cite, please use: IUPAC. Pure Appl. Chem. 84, 2167–2169 (2012). Publication of this document
by any means is permitted on condition that it is whole and unchanged. Copyright © IUPAC 2012.
Copolymer Qualifier Example
(Co)polymer Qualifier Example

In the above example, the oxy subunits in the CRUs are heteroatom chains.
From Fig. 1, oxy subunits are senior to the acyclic carbon chain subunits,
the largest of which are bromo-substituted -CH
2
-CH
2
- subunits. 1-Bromo -
ethane-1,2-diyl is chosen in preference to 2-bromoethane-1,2-diyl as the
former has a lower locant for the bromo-substituent. The preferred CRU is
therefore oxy(1-bromoethane-1,2-diyl) and the polymer is thus named
poly[oxy(1-bromoethane-1,2-diyl)]. Please note the enclosing marks
around the subunit carrying the substituent.
Polymers that are not made up of regular repetitions of a single CRU are
called irregular polymers. For these, each constitutional unit (CU) is sepa-
rated by a slash, e.g., poly(but-1-ene-1,4-diyl/1-vinylethane-1,2-diyl).
9
4.2 Regular double-strand organic polymers
10
Double-strand polymers consist of uninterrupted chains of rings. In a spiro
polymer, each ring has one atom in common with adjacent rings. In a lad-
der polymer, adjacent rings have two or more atoms in common. To iden-
tify the preferred CRU, the chain is broken so that the senior ring is
retained with the maximum number of heteroatoms and the minimum num-
ber of free
valences.
An example is . The preferred CRU is an acyclic subunit of 4 car-
bon atoms with 4 free valences, one at each atom, as shown below. It is ori-
ented so that the lower left atom has the lowest number
. The free-valence
locants are written before the suffix, and they are cited clockwise from the
lower left position as: lower-left, upper-left:upper-right, lower-
right. This example is thus named poly(butane-1,4:3,2-tetrayl).
For more complex structures, the order of seniority again follows
Fig. 1.
5) Nomenclature of Inorganic and Inorganic–Organic Polymers
11
Some regular single-strand inorganic polymers can be named like organic
polymers using the rules given above, e.g., [O-Si(CH
3
)
2
]
n
and [Sn(CH
3
)
2
]
n
are named poly[oxy(dimethylsilanediyl)] and poly(dimethylstannanediyl),
respectively. Inorganic polymers can also be named in accordance with
inorganic nomenclature, but it should be noted that the seniority of the ele-
ments is different to that in organic nomenclature.
However, certain inorganic–organic polymers, for exam-
ple those containing metallocene derivatives, are at pres-
ent best named using organic nomenclature, e.g., the
polymer on the left can be named poly[(dimethyl -
silanediyl)ferrocene-1,1'-diyl].
6) Traditional Names
When they fit into the general pattern of systematic nomenclature, some
traditional and trivial names for polymers in common usage, such as poly-
ethylene, polypropylene, and polystyrene, are retained.
7) Graphical Representations
12,13
The bonds between atoms can be omitted, but dashes should be drawn for
chain-ends. The seniority of the subunits does not need to be followed. For
single-strand (co)polymers, a dash is drawn through the enclosing marks,
e.g., poly[oxy(ethane-1,2-diyl)] shown below left. For irregular polymers,
the CUs are separated by slashes, and the dashes are drawn inside the
enclosing marks. End-groups are connected using additional dashes out-
side of the enclosing marks, e.g., α-methyl-ω-hydroxy-poly[oxirane-co-
(methyloxirane)], shown below right.
8) CA Index Names
2
CAS maintains a registry of substances. In the CAS system, the CRU is
called a structural repeating unit (SRU). There are minor differences in the
placements of locants, e.g., poly(pyridine-3,5-diylthiophene-2,5-diyl) is
poly(3,5-pyridinediyl-2,5-thiophenediyl) in the CAS registry, but other-
wise polymers are named using similar methods to those of IUPAC.
14,15
Fig. 1 The order of subunit seniority. The senior subunit is at the top centre. Subunits
of lower seniority are found by following the arrows. The type of subunit, be it a
heterocycle, a heteroatom chain, a carbocycle, or a carbon chain, determines the
colour of the arrow to follow
.
a
Other heteroatoms may be placed in these orders as
indicated by their positions in the periodic table.
8
R. C. HIORNS et al.
2168
© 2012, IUPAC
Pure Appl. Chem.
, Vol. 84, No. 10, pp. 2167–2169, 2012
9
IUPAC. Pure Appl. Chem. 66, 873 (1994).
10
IUPAC. Pure Appl. Chem. 65, 1561 (1993).
11
IUPAC. Pure Appl. Chem. 57, 149 (1985).
12
IUPAC. Pure Appl. Chem. 66, 2469 (1994).
13
IUPAC. Pure Appl. Chem. 80, 277 (2008).
14
Macromolecules 1, 193 (1968).
15
Polym. Prepr. 41(1), 6a (2000).
Table 3 Representations of divalent groups in polymers.
8
a
To avoid ambiguity, wavy lines drawn perpendicular to the free bond, which are
conventionally used to indicate free valences,
13
are usually omitted from graphical
representations in a polymer context.

Guide to polymer nomenclature
2169
© 2012, IUPAC
Pure Appl. Chem.
, Vol. 84, No. 10, pp. 2167–2169, 2012
MEMBERSHIP OF SPONSORING BODIES
Membership of the IUPAC Polymer Division Committee for the period 2012–2013 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: D. Dijkstra (Germany); R. C. Hiorns (France); P. Kubisa (Poland); G. Moad (Australia);
W. Mormann (Germany); D. W. Smith (USA); Associate Members: J. He (China); R. G. Jones (UK); I. Lacík (Slovakia);
M. Sawamoto (Japan); Y. Yagci (Turkey); M. Žigon (Slovenia); National Representatives: V. P. Hoven (Thailand); M. A.
Khan (Bangladesh); J.-S. Kim (Korea); M. Malinconico (Italy); N. Manolova (Bulgaria); S. Margel (Israel); G. S. Mhinzi
(Tanzania); A. M. Muzafarov (Russia); M. I. Sarwar (Pakistan); J. Vohlídal (Czech Republic).
Membership of the Subcommittee on Polymer Terminology for the period 2009–2012 is as follows: Chair:
R. G. Jones (UK); Secretary: T. Kitayama (Japan), 2008–2009; R. C. Hiorns (France), from 2010; Members: G. Allegra
(Italy); M. Barón (Argentina); T. Chang (Korea); A. Fradet (France); J. He (China); K.-H. Hellwich (Germany); M. Hess
(Germany); P. Hodge (UK); K. Horie
(Japan); A. D. Jenkins (UK); J.-I. Jin (Korea); J. Kahovec (Czech Republic);
P. Kratochvíl (Czech Republic); P. Kubisa (Poland); C. K. Luscombe (USA); S. V. Meille (Italy); I. Mita
(Japan); G. Moad
(Australia); W. Mormann (Germany); T. Nakano (Japan); C. K. Ober (USA); S. Penczek (Poland); G. T. Russell (New
Zealand); C. dos Santos (Brazil); F. Schué (France); S. Słomkowski (Poland); D. W. Smith (USA); R. F. T. Stepto (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).
Republication or reproduction of this report or its storage and/or dissemination by electronic means is permitted without the need for formal IUPAC
permission on condition that an acknowledgment, with full reference to the source, along with use of the copyright symbol ©, the name IUPAC, 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.
Deceased.
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Cites methods from "A brief guide to polymer nomenclatu..."

  • ...w re weighed pr cisely (Scheme 1), the molar ratio of SDS to hydrophobic monomer was 20, and issolv in deionized wate to form a clarified mixed solution, and the NaOH solution (30 wt%) was added until the solution had reached a pH of 6 to 7 [17]....

    [...]

  • ...precisely (Scheme 1), the molar ratio of SDS to hydrophobic monomer was 20, and dissolved in deionized water to form a clarified mixed solution, and then NaOH solution (30 wt%) was added until the solution had reached a pH of 6 to 7 [17]....

    [...]

Journal ArticleDOI
TL;DR: The adoption of a nomenclatura quimica consensuada is a herramienta clave for la comunicación eficiente en las ciencias quimicas, for the busqueda con ordenadores en bases de datos and con fine regulatorios, tales como los asociados a la salud y la seguridad o a la actividad comercial as discussed by the authors.
Abstract: INTRODUCCION La adopcion universal de una nomenclatura quimica consensuada es una herramienta clave para la comunicacion eficiente en las ciencias quimicas, para la busqueda con ordenadores en bases de datos y con fines regulatorios, tales como los asociados a la salud y la seguridad o a la actividad comercial. La Union Internacional de Quimica Pura y Aplicada (IUPAC en sus siglas inglesas) ofrece recomendaciones sobre la naturaleza y el uso de la nomenclatura quimica. Los fundamentos de esta nomenclatura se muestran aqui y en los documentos complementarios sobre los sistemas de nomenclatura de quimica organica y polimeros, con hipervinculos a los documentos originales. Un resumen general de la nomenclatura quimica se puede encontrar en Principles of Chemical Nomenclature. Detalles mayores se pueden hallar en Nomenclature of Inorganic Chemistry coloquialmente conocido como el Libro Rojo, y en las publicaciones relacionadas con compuestos organicos (el Libro Azul) y polimeros (el Libro Purpura). Cabe senalar que muchos compuestos pueden tener nombres no-sistematicos o semi-sistematicos (algunos de los cuales no son aceptados por la IUPAC, por ejemplo, porque son ambiguos) y las reglas IUPAC permiten dar mas de un nombre sistematico a un compuesto en muchos casos. La IUPAC esta elaborando la identificacion de los nombres individuales preferidos a efectos de regulacion (Preferred IUPAC Names o PINs). Nota: En este documento, el simbolo ‘=’ se utiliza para dividir los nombres que resultan ser demasiado largos para el formato de la columna, a menos que ya haya un guion presente en el nombre. Los limites entre compuestos ‘organicos’ e ‘inorganicos’ son difusos. Los tipos de nomenclatura descritos en este documento son aplicables a los compuestos, moleculas e iones que no contienen carbono y tambien a muchas estructuras que contienen carbono (Seccion 2), principalmente los que contienen elementos de los grupos 1−12. La mayoria de los compuestos de boro se tratan mediante una nomenclatura especial. 8

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