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POLYMER NOMENCLATURE
49
POLYMER NOMENCLATURE L H. SPERLING^ W. V. METANOMSKI^ AND CHARLES E. CARRAHER, JR.° a. Center for Polymer Science and Engineering, Materials Research Center and Departments of Chemical Engineering and Materials Science and Engineering, Lehigh University, Bethlehem, PA 18015-3194 b. Chemical Abstracts Service, PO Box 3012, Columbus, OH 43210-0012 c. Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431 and, Florida Center for Environmental Studies, NorthCorp Center, Palm Beach Gardens, FL 33410
Introduction Homopolymers Trade Names, Brand Names and Abbreviations Copolymers Readings Introduction Polymers come in a wide variety of shapes and composition. Here we will focus only on the naming of synthetic polymers. Because of the diversity and universality of polymeric materials there existed few guiding principles in the naming of polymeric materials as polymers were emerging. Homopolvmers Common Names. Little reason is associated with the common names of many important polymeric materials. Some are based on the place of origin such as Hevea brasiliensis, which literally means "rubber from Brazil". Others are named after the discoverer. Bakelite, which is a three-dimensional polymer synthesized from the reaction of phenol and formaldehyde, was discovered by Leo Baekeland. Some are named after an element found within the polymer such as thiokols which are polymers that contain sulfur. Special systems and names were developed to name some polymers and polymer
LH. Sperling, W.V. Metanomski and C.E. Carraher, Jr.
50
groupings (see Table 1). Thus, the products of the reaction between diacids and diamines forming polyamides are called "nylons" after DuPont's tradename product, Nylon.. In turn, nylons are named according to the number of carbons in the diamine and dicarboxylic acid or acid chloride used for their synthesis. The nylon produced from reaction of 1,6hexanediamine (six carbons) and sebacic acid (ten carbons) is given the common name nylon-6,10, nylon 610 or nylon 6,10. The product derived from reaction of 1,6hexanediamine and adipic acid (six carbons) is called nylon-6,6. The product derived from reaction of the single reactant caprolactam (six carbons) Is called nylon-6. The recommended name today is polyamide. Thus, the materials above become polyamide 6,10, etc.
Table 1. Common polymer names and groupings. Common name/grouping
Description
Nylons
Polymeric products from reactions of amines with acids or add chlorides Polymers made from acrylic acid or a derivative of acrylic acid Polyester containing a fatty acid Polymer generally containing large amounts of ethylene units but containing units containing Ionic groups-such as acrylic acid units. Polymer produced from reaction of an aromatic alcohol, generally phenol, and an aldehyde, generally formaldehyde. Polymers derived from hydrocarbon monomers including polyethylene and polypropylene; also known as hydrocarbon polymers.. Polymers produced from vinyl monomers.
Acrylics Alkyds lonomers Phenollcs
Polyolefins
Polyvinyls
Source-Based Names. The majority of names used in the common literature for "simple" polymers are source-based. They are based on the common name of the reactant monomer preceded by the prefix poly. Thus, the polymer formed from reaction of vinyl chloride is called poly(vinyl chloride). The polymer formed from the monomer 1phenylethene (or simply phenylethene), which has the common name of styrene, is called polystyrene. This practice holds for many of the polymers formed from reaction of the vinyl group.
HCH=CH —> -(-HCH-CH-)„ -
I
I
X
X
Polymer Nomenclature
51
The appearance of this practice holds true for vinyl-derived polymers that are not directly derived from the monomer. Thus, poly(vinyl alcohol), which is not derived from from the monomer vinyl alcohol but rather from hydrolysis of poly(vinyl acetate), is named as though it were derived from vinyl alcohol. Many condensation polymers are similarly named. In the case of the polyester poly(ethylene terephthalate) the glycol portion of the name of the monomer, ethylene glycol, is employed in constructing the polymer name so that the name is really a hybrid of a source-based named and a structure-based name. 0 -(-0-HCH-HCH-O-C Structure-Based Names. While the majority of common polymers are known by common or source-based names, the "correct" or so-called scientific names are based on rules described by the international body responsible for systematic nomenclature of chemicalscompounds. lUPAC and others have published a series of reports for naming polymers that are used for more complex polymers (1-6). Along with these formal reports. Polymer Chemistry, PC, and Polymeric Materials: Science and Engineering, PMSE periodically publishes updates derived from several study groups (7,8). For linear polymers, the lUPAC system names the components of the repeating unit, arranged in a prescribed order. The rules for selecting the order of the components to be used as the repeating unit are found elsewhere (1-8). Once the order is selected, the naming is straightforward. Following are several illustrations. For polystyrene (source-based name), the lUPAC name is poly(l-phenylethylene); for poly(methyl methacrylate) the lUPAC name is poly[1(methoxycarbonyl)-l -methylethylene]; and for nylon-6,6 (common name) or polyamide 6,6 (source-based) the lUPAC name is poly(iminohexamethyleneiminoadipoyl). Linkage-Based Names. Many polymer "families" are referred to by the name of the particular linkage that connects the polymers (Table 2). The family name is "poly" followed by the linkage-name. Thus, those polymers that contain the amide linkage are known as polyamides; those containing the ester linkage are called polyesters, etc. Tradenames. Brandnames. and Abbreviations Trade (and or brand) names and abbreviations are often used to describe materials. They may be used to identify the product of a manufacturer, processor or fabricator and may be associated with a particular product or with a material or modified material. Trade names are used to describe specific groups of materials that are produced by a specific company or under licence of that company. Thus, a rug whose contents are described as containing Fortrel (TM) polyester fibers contain polyester fibers that are "protected" under the Fortrel trademark and produced or licenced to be produced by the holder of the Fortrel (TM) trademark. Also, Lexan, Merlon, Baylon and Lupilon (TM) are all trade names for polycarbonates manufactured by different companies. Some polymers are better known
LH. Sperling, W.V. Metanomski and C.E. Carraher, Jr.
52
by their trade name than their generic name. For instance polytetrafluoroethylene is better known as Teflon (TM), the trade name held by DuPont. Table 2. Linkage-based names. Family name
Linkage
Family name
Linkage
Polyvinyl
-C-C-
0 Polyamide
Polyester
II
-N-C0
0
0
II
II
II
-0-C-
Polyanhydride
0
0 Polyurethane
II -0-C-N-
-C-O-C-
II Polyurea
-N-C-N0
Polyether
-0-
Polycarbonate
II
-0-C-O0
Polysiloxane
-0-Si-
Polysulfide
-S-R-
II
Polyphosphate ester -0-P-O-R0 R
Abbreviations are also employed to describe materials. Table 3 contains a listing of some of the more widely employed abbreviations and the polymer associated with the abbreviation.
Polymer Nomenclature
53
Table 3. Abbreviations for selected polymeric materials. Abbreviation
Polymer
Abbreviation
Polymer
CA
Cellulose acetate
EP MF PAN
Acrylonitrilebutadiene-styrene copolymer Epoxy Melamine-formaldehyde polymer Polyacrylonitrile
HIPS PAA SBR, PBS
PBT PE
Poly(butylene terephthalate) Polyethylene
PC PET
PF PP PS PU PVC
Phenol-formaldehyde polymer Polypropylene Polystyrene Polyurethane Poly(vinyl alcohol) Poly(vinyl chloride)
High-impact polystyrene Poly(acrylic acid) B utadiene-styrene copolymer Polycarbonate P o l y ( e t h y l e n e terephthalate) Poly(methyl methacrylate) Poly(phenylene oxide) Polytetrafluoroethylene Poly(vinyl acetate) Poly(vinyl butyral) Styrene-acrylonitrile copolymer
UF
Urea-formaldehyde polymer
ABS
PVA, PVAI
PMMA
PPO PTFE PVA, PVAc
PVB SAN
Copolvmers Generally, copolymers are defined as polymeric materials containing two or more kinds of mers. It is important to distinguish between two kinds of copolymers-those with statistical distributions of mers, or at most, short sequences of mers (Table 4) and those containing long sequences of mers connected in some fashion (Table 5). Table 4. Short sequence copolymer nomenclature. Type Homopolymer Unspecified Statistical Random Periodic Alternating Network
Connective
Example
none
PolyA Po/y(A-co-B) Poly(A-sfaf-B) Poly(A-ran-B) Poly(A-per-B-per...) Poly(A-a/f-B) nef-PolyA
'00-
'Stat-ran-per'altnet'
54
LH. Sperling, W.V. Metanomski and C.E. Carraher, Jr.
Table 5. Long sequence copolymer nomenclature. Type
Connective
Example
Block copolymer Graft copolymer AB-Crosslinked Polymer blend Interpenetrating network polymer Starblock
'block-graft-net-blend-
PolyA-6/oc/c-polyB PolyA-gra/?-polyB PolyA-nef-polyB PolyA-6/e/7cf-polyB
-ipn- or 'interstar-
nef-PolyA-/p/?-nef-polyB Sfar-(PolyA-6/oc/c-polyB)
Literature Cited 1. lUPAC Report on Nomenclature In the Field of Macromolecules, J. Polvm. Sci..1952. 8 257. 2. A Structure-Based Nomenclature for Linear Polymers, Macromolecules. 1968,1,193. 3. lUPAC, PureAppl. Chem.. 1976, 48, 373; 1985, 57,149,1427; 1993, 65,1561; 1994, 66, 873; 1997, 69, 2511, 1998, 70, 701. 4. lUPAC, "Compendium of Macromolecular Nomenclature", W. V. Metanomski, Ed., Blackwell, Oxford, 1991. 5. Carraher, C. E., Hess, G., Sperling, L H., J. Chem. Ed., 1987, 64, 36. 6. Bikales, N. M., "Encyclopedia of Polymer Science and Engineering", 2"** Ed., Vol. 10, 191, Wiley, NY, 1987. 7. Polymer Prepr., 1991.32(1). 655; 1992, 33(21, 6; 1993, 34(1). 6; 1993, 34(2).6:1994, 35(1)6:1995, 36(1). 6; 1995. 36(2). 6:1996.37(1). 6; 1998. 39(1). 9; 1998,39(2). 6; 1999, 40(1). In press. 8. Polym. Mater. Sci. Eng., 1993, 68, 341; 1993, 69, 575; 1995, 72, 612; 1996, 74, 445; 1998, 78, Back Page; 1998, 79, Back Page; 1999, 80, Back Page.
POLYMER NOMENCLATURE L H. SPERLING^ W. V. METANOMSKI^ AND CHARLES E. CARRAHER, JR.° a. Center for Polymer Science and Engineering, Materials Research Center and Departments of Chemical Engineering and Materials Science and Engineering, Lehigh University, Bethlehem, PA 18015-3194 b. Chemical Abstracts Service, PO Box 3012, Columbus, OH 43210-0012 c. Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431 and, Florida Center for Environmental Studies, NorthCorp Center, Palm Beach Gardens, FL 33410
Introduction Homopolymers Trade Names, Brand Names and Abbreviations Copolymers Readings Introduction Polymers come in a wide variety of shapes and composition. Here we will focus only on the naming of synthetic polymers. Because of the diversity and universality of polymeric materials there existed few guiding principles in the naming of polymeric materials as polymers were emerging. Homopolvmers Common Names. Little reason is associated with the common names of many important polymeric materials. Some are based on the place of origin such as Hevea brasiliensis, which literally means "rubber from Brazil". Others are named after the discoverer. Bakelite, which is a three-dimensional polymer synthesized from the reaction of phenol and formaldehyde, was discovered by Leo Baekeland. Some are named after an element found within the polymer such as thiokols which are polymers that contain sulfur. Special systems and names were developed to name some polymers and polymer
LH. Sperling, W.V. Metanomski and C.E. Carraher, Jr.
50
groupings (see Table 1). Thus, the products of the reaction between diacids and diamines forming polyamides are called "nylons" after DuPont's tradename product, Nylon.. In turn, nylons are named according to the number of carbons in the diamine and dicarboxylic acid or acid chloride used for their synthesis. The nylon produced from reaction of 1,6hexanediamine (six carbons) and sebacic acid (ten carbons) is given the common name nylon-6,10, nylon 610 or nylon 6,10. The product derived from reaction of 1,6hexanediamine and adipic acid (six carbons) is called nylon-6,6. The product derived from reaction of the single reactant caprolactam (six carbons) Is called nylon-6. The recommended name today is polyamide. Thus, the materials above become polyamide 6,10, etc.
Table 1. Common polymer names and groupings. Common name/grouping
Description
Nylons
Polymeric products from reactions of amines with acids or add chlorides Polymers made from acrylic acid or a derivative of acrylic acid Polyester containing a fatty acid Polymer generally containing large amounts of ethylene units but containing units containing Ionic groups-such as acrylic acid units. Polymer produced from reaction of an aromatic alcohol, generally phenol, and an aldehyde, generally formaldehyde. Polymers derived from hydrocarbon monomers including polyethylene and polypropylene; also known as hydrocarbon polymers.. Polymers produced from vinyl monomers.
Acrylics Alkyds lonomers Phenollcs
Polyolefins
Polyvinyls
Source-Based Names. The majority of names used in the common literature for "simple" polymers are source-based. They are based on the common name of the reactant monomer preceded by the prefix poly. Thus, the polymer formed from reaction of vinyl chloride is called poly(vinyl chloride). The polymer formed from the monomer 1phenylethene (or simply phenylethene), which has the common name of styrene, is called polystyrene. This practice holds for many of the polymers formed from reaction of the vinyl group.
HCH=CH —> -(-HCH-CH-)„ -
I
I
X
X
Polymer Nomenclature
51
The appearance of this practice holds true for vinyl-derived polymers that are not directly derived from the monomer. Thus, poly(vinyl alcohol), which is not derived from from the monomer vinyl alcohol but rather from hydrolysis of poly(vinyl acetate), is named as though it were derived from vinyl alcohol. Many condensation polymers are similarly named. In the case of the polyester poly(ethylene terephthalate) the glycol portion of the name of the monomer, ethylene glycol, is employed in constructing the polymer name so that the name is really a hybrid of a source-based named and a structure-based name. 0 -(-0-HCH-HCH-O-C Structure-Based Names. While the majority of common polymers are known by common or source-based names, the "correct" or so-called scientific names are based on rules described by the international body responsible for systematic nomenclature of chemicalscompounds. lUPAC and others have published a series of reports for naming polymers that are used for more complex polymers (1-6). Along with these formal reports. Polymer Chemistry, PC, and Polymeric Materials: Science and Engineering, PMSE periodically publishes updates derived from several study groups (7,8). For linear polymers, the lUPAC system names the components of the repeating unit, arranged in a prescribed order. The rules for selecting the order of the components to be used as the repeating unit are found elsewhere (1-8). Once the order is selected, the naming is straightforward. Following are several illustrations. For polystyrene (source-based name), the lUPAC name is poly(l-phenylethylene); for poly(methyl methacrylate) the lUPAC name is poly[1(methoxycarbonyl)-l -methylethylene]; and for nylon-6,6 (common name) or polyamide 6,6 (source-based) the lUPAC name is poly(iminohexamethyleneiminoadipoyl). Linkage-Based Names. Many polymer "families" are referred to by the name of the particular linkage that connects the polymers (Table 2). The family name is "poly" followed by the linkage-name. Thus, those polymers that contain the amide linkage are known as polyamides; those containing the ester linkage are called polyesters, etc. Tradenames. Brandnames. and Abbreviations Trade (and or brand) names and abbreviations are often used to describe materials. They may be used to identify the product of a manufacturer, processor or fabricator and may be associated with a particular product or with a material or modified material. Trade names are used to describe specific groups of materials that are produced by a specific company or under licence of that company. Thus, a rug whose contents are described as containing Fortrel (TM) polyester fibers contain polyester fibers that are "protected" under the Fortrel trademark and produced or licenced to be produced by the holder of the Fortrel (TM) trademark. Also, Lexan, Merlon, Baylon and Lupilon (TM) are all trade names for polycarbonates manufactured by different companies. Some polymers are better known
LH. Sperling, W.V. Metanomski and C.E. Carraher, Jr.
52
by their trade name than their generic name. For instance polytetrafluoroethylene is better known as Teflon (TM), the trade name held by DuPont. Table 2. Linkage-based names. Family name
Linkage
Family name
Linkage
Polyvinyl
-C-C-
0 Polyamide
Polyester
II
-N-C0
0
0
II
II
II
-0-C-
Polyanhydride
0
0 Polyurethane
II -0-C-N-
-C-O-C-
II Polyurea
-N-C-N0
Polyether
-0-
Polycarbonate
II
-0-C-O0
Polysiloxane
-0-Si-
Polysulfide
-S-R-
II
Polyphosphate ester -0-P-O-R0 R
Abbreviations are also employed to describe materials. Table 3 contains a listing of some of the more widely employed abbreviations and the polymer associated with the abbreviation.
Polymer Nomenclature
53
Table 3. Abbreviations for selected polymeric materials. Abbreviation
Polymer
Abbreviation
Polymer
CA
Cellulose acetate
EP MF PAN
Acrylonitrilebutadiene-styrene copolymer Epoxy Melamine-formaldehyde polymer Polyacrylonitrile
HIPS PAA SBR, PBS
PBT PE
Poly(butylene terephthalate) Polyethylene
PC PET
PF PP PS PU PVC
Phenol-formaldehyde polymer Polypropylene Polystyrene Polyurethane Poly(vinyl alcohol) Poly(vinyl chloride)
High-impact polystyrene Poly(acrylic acid) B utadiene-styrene copolymer Polycarbonate P o l y ( e t h y l e n e terephthalate) Poly(methyl methacrylate) Poly(phenylene oxide) Polytetrafluoroethylene Poly(vinyl acetate) Poly(vinyl butyral) Styrene-acrylonitrile copolymer
UF
Urea-formaldehyde polymer
ABS
PVA, PVAI
PMMA
PPO PTFE PVA, PVAc
PVB SAN
Copolvmers Generally, copolymers are defined as polymeric materials containing two or more kinds of mers. It is important to distinguish between two kinds of copolymers-those with statistical distributions of mers, or at most, short sequences of mers (Table 4) and those containing long sequences of mers connected in some fashion (Table 5). Table 4. Short sequence copolymer nomenclature. Type Homopolymer Unspecified Statistical Random Periodic Alternating Network
Connective
Example
none
PolyA Po/y(A-co-B) Poly(A-sfaf-B) Poly(A-ran-B) Poly(A-per-B-per...) Poly(A-a/f-B) nef-PolyA
'00-
'Stat-ran-per'altnet'
54
LH. Sperling, W.V. Metanomski and C.E. Carraher, Jr.
Table 5. Long sequence copolymer nomenclature. Type
Connective
Example
Block copolymer Graft copolymer AB-Crosslinked Polymer blend Interpenetrating network polymer Starblock
'block-graft-net-blend-
PolyA-6/oc/c-polyB PolyA-gra/?-polyB PolyA-nef-polyB PolyA-6/e/7cf-polyB
-ipn- or 'interstar-
nef-PolyA-/p/?-nef-polyB Sfar-(PolyA-6/oc/c-polyB)
Literature Cited 1. lUPAC Report on Nomenclature In the Field of Macromolecules, J. Polvm. Sci..1952. 8 257. 2. A Structure-Based Nomenclature for Linear Polymers, Macromolecules. 1968,1,193. 3. lUPAC, PureAppl. Chem.. 1976, 48, 373; 1985, 57,149,1427; 1993, 65,1561; 1994, 66, 873; 1997, 69, 2511, 1998, 70, 701. 4. lUPAC, "Compendium of Macromolecular Nomenclature", W. V. Metanomski, Ed., Blackwell, Oxford, 1991. 5. Carraher, C. E., Hess, G., Sperling, L H., J. Chem. Ed., 1987, 64, 36. 6. Bikales, N. M., "Encyclopedia of Polymer Science and Engineering", 2"** Ed., Vol. 10, 191, Wiley, NY, 1987. 7. Polymer Prepr., 1991.32(1). 655; 1992, 33(21, 6; 1993, 34(1). 6; 1993, 34(2).6:1994, 35(1)6:1995, 36(1). 6; 1995. 36(2). 6:1996.37(1). 6; 1998. 39(1). 9; 1998,39(2). 6; 1999, 40(1). In press. 8. Polym. Mater. Sci. Eng., 1993, 68, 341; 1993, 69, 575; 1995, 72, 612; 1996, 74, 445; 1998, 78, Back Page; 1998, 79, Back Page; 1999, 80, Back Page.