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Divinylbenzene
Table of Contents
Divinylbenzene ........................................................................................................................... 4
The versatile cross-linking agent for improving material properties
DVB grades
Technical Information ................................................................................................................ 5-7
Properties of styrene/divinylbenzene copolymersheat distortion,
impact strength, tensile strength, hardness
Physical properties
Typical Applications of DVB ...................................................................................................... 8-10
Adhesives, Analytical, Antioxidants, Biological, Catalysis,
Ceramics, Chromatography, Coatings, Combinatorial Chemistry,
Composite Plastics, Elastomers, Electrochemical, Ion Exchange,
Membranes, Optical Applications, Pharmaceutical, Plastics,
Polymer Synthesis, Reprography, Rubber, Specialty Polymers, Star Polymers
Handling and Storage (including inhibitor handling) ................................................................. 11-13
Inhibition of DVB
Standard inhibition levels in DVB
Special cases where inhibitor removal is desired
Other factors affecting inhibitor level
Oxygen requirements of TBC
Polymer analysis and dissolved oxygen
Addition of TBC to stored monomer
Information on Storage Facilities .............................................................................................. 14-21
Tanks, Pumps, Lines and valves, Gaskets, Breathers, Level indicators,
Flexible transfer hoses
Reducing oxidation and side reactions during storage
Containers
Polymerization of stored monomer
Handling runaway polymerization
General Information ................................................................................................................... 22-23
Safe handling practices
Flammability
Fires
Spills
Disposal
Static electricity
Distribution Emergency Response
Toxicity, First Aid, and Industrial Hygiene Measures for DVB .................................................. 24-25
Inhalation
Skin contact
Eye contact
Ingestion
Patents and References Involving DVB ..................................................................................... 26-42
Adhesives, Analytical, Antioxidants, Biological, Catalysis,
Ceramics, Chromatography, Coatings, Combinatorial Chemistry,
Composite Plastics, Elastomers, Electrochemical, Ion Exchange,
Membranes, Optical Applications, Pharmaceutical, Plastics,
Polymer Synthesis, Reprography, Rubber, Specialty Polymers, Star Polymers
Customer Notice ........................................................................................................................ 43
Divinylbenzene
Technical Information
Typical Chemical Analysis and Structural Formulae1
Structural Formula
DVB-55
DVB-63
DVB-HP
Total Divinylbenzene
56%
63.5%
80%
2.3
2.3
2.3
Total Ethylvinylbenzene
43.0%
35.5%
19%
2.3
2.3
2.3
Diethylbenzene
<0.05%
<0.05%
<0.05%
Naphthalene
<0.04%
<0.04%
<0.04%
Benzene content
N.D.
N.D.
N.D.
900-1100 ppm
900-1100 ppm
Color (Gardner)
<4
<4
<4
Polymer
< 5 ppm
< 5 ppm
<5 ppm
These typical analyses are intended to serve as a guide only and not as specification limits.
Divinylbenzene CAS #001321-74-0
3
Ethylvinylbenzene CAS #028106-30-1
N.D. Not detectable with current instruments (<50 parts per billion)
2
Heat Distortion
Impact Strength
200
18
190
16
180
14
Impact Strength
(Inch PoundsIzod Test Un-notched
Properties of
Styrene/
Divinylbenzene
Copolymers
170
160
150
140
130
120
110
12
10
100
90
80
0
0
10
20
Divinylbenzene, %
30
40
20
40
60
80
Divinylbenzene, %
100
120
Tensile Strength
Hardness
105
8,000
7,000
100
6,000
Rockwell Superficial
Hardness (15 kg 1/8" Ball W )
95
5,000
4,000
3,000
85
80
2,000
1,000
75
70
0
10
20
30
40 50 60
Divinylbenzene, %
70
80
90
20
40
60
80
Divinylbenzene, %
100
120
Property
Molecular Weight
Boiling Point, C at 760 mm
Pseudocritical Pressure, Pc atm.
Pseudocritical Temperature, tc C
Vapor Density (air = 1)
Vapor Pressure, mm Hg
Physical Properties
Density, lb/gal
Vapor Pressure
1,000
200
Temp. C (DVB-55)
0
25
50
75
100
125
150
175
200
25
20
25
30
20
25
30
25
25
25
25
25
20
30
Divinylbenzene
(DVB-63)
(DVB-HP)
130.191
195
34.2
425
4.5
0.07
0.6
3.0
11.7
36.2
93.8
212.4
431.2
801.3
0.42
0.9123
0.9084
0.9044
7.61
7.58
7.55
130.191
197
34.4
427
4.5
0.08
0.6
2.9
11.4
35.0
91.1
207.1
422.3
788.2
0.42
0.9151
0.9111
0.9070
7.64
7.60
7.57
130.191
200
34.9
432
4.5
0.08
0.6
2.8
10.7
33.0
86.3
197.7
406.5
764.8
0.42
.9211
.9167
.9124
7.69
7.65
7.61
0.67-6.1
68 (155)
505 (941)
< 50
101.3
83.8
1.5585
0.0052
0.054
1.0
8.66 x 10-4
8.74 x 10-4
pale yellow
0.64-6.1
69 (156)
494 (921)
< 50
96.9
79.4
0.0052
0.054
1.0
8.66 x 10-4
8.74 x 10-4
pale yellow
0.69-6.2
70 (158)
470 (878)
< 50
94.9
77.4
0.0052
0.054
1.0
8.65 x 10-4
8.70 x 10-4
pale yellow
mm/Hg
100
20
10
0
0
10
20
60
100
140
Temperature, C
180
220
Typical Applications of
DVB
Adhesives
DVB has been found to improve the high
temperature strength of adhesives used to
bond aluminum to aluminum. Used in an
acrylic hydrosol to bond Bakelite resin and
polyester film, DVB was found to increase
creep rupture time dramatically. DVB has
found utility in cross-linked styrene/butadiene
polymers used for caulks and mastics for the
construction industry.
Catalysis
DVB has been used to create a hydrophobic
foam for use as a hydrogen-water exchange
catalyst. In another instance, a catalyst was
bonded to a DVB-containing copolymer for
hydroformylation of C2-30 alpha-olefins with CO
and H. DVB has also served as a catalyst for
hydrolyzing nitriles to amides.
Ceramics
In a polymer impregnation system, DVB has
improved both the physical and mechanical
properties of fired clay bodies. Its also been
used as part of a treatment to impregnate and
harden carbonizable material to produce a
composite C material.
Chromatographic Resins
DVB has been used in the production of
reversed-phase packings for liquid
Biological
DVB has been used to produce cell culture
micro-carrier beads. These resulting beads
have capacity comparable to dextran beads
but swell less. They also have a tighter size
distribution and can be regenerated. DVB has
also been incorporated in a hydrogel for slow
nutrient release fertilizer.
Coatings
DVB has been used as part of a system for
bonding a layer of phosphonitrilic polymer to
rubber to improve the surface properties of
rubber goods for biomedical applications. It
has also been used to create a photocurable
protective coating for wood, metal, glass,
and plastic.
Combinatorial Chemistry
Electrochemical
Pharmaceutical
bending resistance.
Ion Exchange
be attached.
DVB is used in a wide variety of ion
Polymer Synthesis
and capacity.
Composite Plastics
Membranes
Elastomers
Optical Applications
and hardness. It also increases the skidresistance of some rubber compounds and
improves the adhesion of rubber to steel,
organic, or inorganic filaments. DVB has
also been used to improve the adhesive tear
strength and elongation properties of
rubber-based sealants.
Plastics
Star Polymers
index improvers.
Reprography
Miscellaneous
When paraffin is cross-linked with
DVB, an additive is created that
diesel fuel.
Rubber
Synthetic rubber is any one of a group of
formations.
Solid makeups containing volatile
an encapsulating resin.
matter.
10
guidelines.
Inhibition of DVB
storage stability.
11
Interval
Inhibitor analysis
Polymer analysis
Color
Monthly
Monomer temperature
Daily
At least quarterly
2. Roof
Yearly
3. Sides
Yearly
4. Floor
Yearly
At least quarterly
Running log
Running log
Running log
is desired
12
on site.
than necessary.
these impurities.
handling problems.
aerated as necessary.
polymerizationrunaway polymerization
or greater.
13
Information on
Storage Facilities
dual-service purposes.
Tanks
14
15
charge buildup.
Pumps
16
Gaskets
Manhole covers for cleaning or sampling
should have gaskets made of Viton
fluoroelastomer or Teflon resin. In addition,
Dow recommends all gaskets used in handling
DVB be made of these materials. Listed below
are pump seals and gaskets which have
proven satisfactory in DVB service. Similar
materials from other manufacturers may work
equally well.
Pump Seals:
John Crane Type 9T
Teflon resin V wedge with carbon
face seal
Runs against carbon seat
Stainless steel hardware
Gaskets:
Flexitallic 304SS flanged joint spiral wound
with asbestos filler and inner ring. Flexitallic
Gasket Co., 151 Heller Place, Bellmawr, NJ
08031. Phone: 609-931-2500.
Unilon BS2815 Grade A BS1832,
1/16-inch compressed. James Walker Mfg.,
511 West 195th Street, Glenwood, IL 60425.
Breathers
Air-blanketed, non-pressurized DVB storage
tanks should be fitted with approved vents
according to local codes. You should also
install additional venting facilitiesfor both
pressure and vacuum reliefto protect
the tank in case there is a sudden pressure
buildup, or open vents are plugged. Frangible
safeties or vacuum-pressure safety relief
valves are recommended for this purpose on
smaller units. On larger storage facilities, both
manhole emergency relief venting for pressure
and a vacuum-pressure relief valve are highly
recommended to assure protection against
tank collapse. In addition, inspect all vents at
least every six months for polymer plugging.
17
Level indicators
Float-type, dial-reading gauges are acceptable,
but for remote readings, flange-mounted
differential pressure transmitters are
recommended. All storage tanks should
contain either a local temperature indicator,
or a temperature sensor for remote reading.
18
Additional comments
on storage
mechanical means.
entry is made.
handling equipment.
Containers
The type of container in which DVB is shipped
and stored is very important to monomer
purity and stability. Lined and unlined black
iron, aluminum, and stainless steel containers
are all satisfactory, and typically used to store
and transport DVB. Avoid copper and copper-
19
20
Storage Temperature
Storage Time
Aerate Within
<40F
4050F
5060F
6070F
12 months
8 months
4 months
2 months
6 months
6 months
4 months
2 months
7080F
1 month
1 month
21
Property
Value
DVB-55
155F (68C)
Autoignition temperature
941F (505C)
General Information
DVB-63
156F (69C)
Autoignition temperature
921F (494C)
Upper limit:
DVB-HP
157F (70C)
Autoignition temperature
878F (470C)
Upper limit:
Fires
Flammability
DVB will burn. Exercise the same precautions
against fire and explosion hazards that are
commonly applied to other combustible
and flammable liquids. The flammability
properties of DVB are given in the table above.
22
Spills
Disposal
designated furnace. Comply with federal, state, Dow system for advising and assisting anyone
Static electricity
DVB, with its high-volume resistivity, can pick
up and hold a static charge during transfer
from a tank truck to a storage tank. Always
make sure that the storage tank and tank truck
are well-grounded.
23
Inhalation
Inhalation of DVB can cause respiratory irritation
and, at higher concentrations, anesthetic and
narcotic effects. The ACGIH (American
Conference of Governmental and Industrial
Hygienists) Threshold Limit Value/Time
Weighted average concentration (TLV/TWA)
and the OSHA permissible exposure limit
(PEL) for DVB are 10 ppm.
24
Skin contact
Ingestion
medical attention.
Eye contact
25
Adhesives
Analytical
US 6,123,850 (2000).
Japan
Antioxidants
1. Stabilized Polyglycol Compositions, Edward O.
Ohlmann, (to The Dow Chemical Company),
US 2,665,312 (1954).
2. Spandex Fibers Stabilized with Condensates of
26
Biological
1. Cell culture microcarriers based on the
polymerization product of an aromatic
monovinyl hydrocarbon
Eduard Pieter
AKZO N. V.
Neth.
Eur. Pat. Appl. EP 109124 A2, 23 May 1984 14 pp.
Designated States: BE, DE, FR, GB, IT, NL, SE
2. Fertilizer
Heller, Harold; Schaepel, Dietmar; Hentschel, Claus;
Catalysis
US 4,914,151 (1990).
5. Synthetic Polystyrene Resin and its Use in Solid
Phase Peptide Synthesis, Hans Rink, (to Ciba-Geigy
Corporation), US 5,004,781 (1991).
6. Material for Purification of Physiological Liquids of
Organism, Vadim Davankov, (to Renal Tech
International LLC), US 6,114,466 (2000).
7. Method of Producing Material for Purification of
Chemical Research;
Japan
US 5,502,016 (1996).
Texaco Inc.
USA
US 6,127,311 (2000).
27
Chromatography
1. Process for Purifying Blocked Synthetic Peptides,
US 3,857,829 (1974).
(1998).
2. Cross-linked Polystyrene and Substituted
13. Method for Making Bis-Xylenols Containing Acid
Moieties, Geert-Jan Willems, (to General Electric
US 6,020,529 (2000).
4. High Performance Ion Exchange Composition,
15. Carbonylation Catalyst Supported on a Carbonized
Polysulfonated Divinylbenzene-Styrene Copolymer,
6,329,556 B1 (2001).
US 4,272,246 (1981).
Japan
28
US 5,786,219 (1998).
Combinatorial Chemistry
1. Microspheres with Fluorescent Spherical Zones,
Japan
Jpn. Kokai Tokkyo Koho JP 60/149402 A2
(85/149402), 6 Aug 1985, 3pp.
US 6,039,876 (2000).
US 4,959,219 (1990).
US 5,688,987 (1997).
Japan
Jpn. Kokai Tokkyo Koho JP 59/177168 A2
(84/177168), 6 Oct 1984, 4 pp.
US 6,435,240 B1 (2002).
29
Elastomers
1. Thermoplastic rubber blends for injection molding
Japan
Composite Plastics
Iseda, Yutaka
30
block polymers
Matsuda, Akira
Japan
USA
Japan
Anzai, Shiro
Japan
Japan
Diner, E. A.; et al
USSR
Yamamuro, Okimasa
Anzai, Shiro
Japan
Japan
USA
Iseda, Yutaka
Anzai, S.
Japan
Tokyo, Japan
Anzai, Shiro
Bridgestone Tire Co., Ltd.
Japan
31
US 4,295,952 (1981).
US 4,652,350 (1987).
Thomson-CSF S. A.
US 6,262,879 B1 (2001).
Fr.
Fr. Demande FR 2389922, 1 Dec 1978, 9 pp.
2. Prepreg sheets
Hitachi Chemical Co., Ltd.
Japan
Jpn. Kokai Tokkyo Koho JP 56/32526
{81/32526}, 2 Apr 1981, 5 pp.
3. Alkaline battery
Matsushita Electric Industrial Co., Ltd.
Japan
Jpn. Kokai Tokkyo Koho JP 59/189568 A2
{84/189568}, 27 Oct 1984, 4 pp.
4. Preparation of toners for electrostatic
image development
Canon K. K.
Japan
Jpn. Kokai Tokkyo Koho JP 60/57855 A2
{85/57855}, 3 Apr 1985, 7 pp.
5. Anionic Membranes, Oronzio deNora,
Ion Exchange
1. Recovering carboxylic acids
Kawabata, Nariyoshi; Yasuda, Shinichi;
Yamazaki, Takeshi
Koei Chemical Co., Ltd.
Japan
Ger. Offen. DE 3043766, 4 Jun 1981, 22 pp.
2. Synthesis of divinylbenzene-cross-linked terpolymer
consisting of heminstyrene-(1-vinyl-2-methylimidazole)
as cyanide ion exchanger
Kokufuta, Etsuo; Saito, Kiyoshi
Inst. Appl. Biochem., Univ. Tsukuba
Sakura 305, Japan
Polym. Bull. (Berlin), 14 (1), 93-8
3. Advanced treatment of industrial
wastewater using unutilized mineral resources.
(II).
Treatment of wastewater containing various
organic substances
US 4,221,642 (1980).
32
structures
US 6,413,498 B1 (2002).
US 6,420,439 B1 (2002).
US 6,478,961 B2 (2002).
Membranes
1. Electrolysis diaphragm
Bachot, Jean; Grosbois, Jean
Fr.
Optical Applications
membranes
US 5,449,462 (1995).
3. Cation-exchange membrane
Japan
US 3,607,706 (1971).
US 5,523,327 (1996).
5. Macroporous Polymeric Membranes for the
11. Phosphonic Acid Based Ion Exchange Resins,
US 5,539,003 (1996).
US 4,923,610 (1990).
US 5,298,327 (1994).
4. Manufacturing Method of a Polymer GRIN Lens
Using Sulfonation, Sang-Don Jung, (to Electronic
& Telecommunications Research Inst.),
US 5,567,363 (1996).
5. High Refractive Index Photochromic Ophthalmic
Article, Charles R. Coleman, (to PPG Industries,
Inc.), US 5,708,064 (1998).
6. Process for Production of Photochromic Cured
Product, Satoshi Imura, (to Tokuyama Corporation),
US 5,910,516 (1999).
7. Temperature Stable and Sunlight Protected
Photochromic Articles. Frederic Henri Florent,
(to Corning Incorporated), US 5,973,039 (1999).
8. Optical Resin Composition, Robert A. Smith,
(to PPG Industries Ohio, Inc.), US 5,917,006 (1999).
US 5,258,106 (1993).
33
Pharmaceutical
1. New polymer containing aminoalkyl group and its
application to enzyme- and coenzyme-support
Narita, Tadashi; Hirano, Tsuneo
Dep. Environ. Technol., Saitama Inst. Technol.
US 6,051,315 (2000).
2. A comparative study of the mechanical-physical
13. Method for Producing a Shaped Piece Suitable for
copolymerizable additives
US 6,162,853 (2000).
Timisoara, Rom.
Rev. Chir., Oncol., Radiol., ORL,
Oftalmol., Stomatol., Stomatol., 26(4), 299-304
3. Biologically active proteins bound to copolymers
Batkai, Laszlo; Kovacs, Anna; Horvath, Istvan;
Inczefi, Istvan; Li, Valentina; Marmarosi, Mrs. Tamas
Chinoin Gnogyszer es Vegyeszeti Termekek
Gyara Rt.
Hung.
US 6,329,482 B1 (2001).
Shibatani, Koichiro
34
3. Cross-linked copolymers
9. Radiation-cross-linked plasticized
PVC pipes
Repina, E. V.
Tudoric-Ghemo. J.
USSR
Japan
difunctional monomers
Arbit, Harold A.
Japan
Rhone-Poulenc Indutries S. A.
Fr.
Fr. Demande FR 2432033, 22 Feb 1980, 15 pp.
2. Copolymerization of glycidyl methacrylate-methyl
methacrylate-divinylbenzene in cyclohexane
Yasuhiro
Japan
35
Japan
Japan
Jpn. Kokai Tokkyo Koho JP 60/195133 A2
{85/195133}, 3 Oct 1985, 9 pp.
22. Thermoplastic mixture with
polyfunctional compound
Bussink, Jan; Van der Meer, Roelof
General Electric Co.
USA
Eur. Pat. Appl. EP 177988 A1, 16 Apr 1986,
17 pp. Designated States: DE, FR, GB, IT, NL
23. Propylene polymer compositions
Kobayashi, Takeshi; Tone, Fumihiro; Akiyama, Koji
Idemitsu Petrochemical Co., Ltd.
Japan
Jpn. Kokai Tokkyo Koho JP 61/85462 A2
{86/85462}, 1 May 1986, 5 pp.
24. Optical disks
Ikeno, Shinobu; Usui, Hiroaki; Nakamura,
Masashi; Takanaga, Tetsuya
Matsushita Electric Works, Ltd.
Japan
Jpn. Kokai Tokkyo Koho JP 61/142551 A2
{86/142551}, 30 Jun 1986, 6 pp.
25. Modification of propylene polymers
Kobayashi, Takeshi; Tone, Fumihiro; Akiyama, Koji
Idemitsu Petrochemical Co., Ltd.
Japan
Jpn. Kokai Tokkyo Koho JP 61/152754 A2
{86/152754}, 11 Jul 1986, 4 pp.
26. Curing of phenol-formaldehyde resins
Starks, Charles M.
Conoco, Inc.
USA
U.S. US 4200706, 29 Apr 1980, 4 pp.
36
Toshimasa
US 4,665,103 (1987).
USA
Japan
Kiyoshi
Nihon Hatsujo K. K.
Japan
USSR
USA
Japan
US 5,047,472 (1991).
US 4,464,435 (1984).
37
Ilichev, S. N.
USSR
Plast. Massy, (8), 5-7
Trbojevic-Gobac, Slobodanka
Ekon. Fak.
Zagreb, Yugoslavia
B.V.
Neth.
Ger. Offen. DE 3428402 Al, 21 Feb 1985, 17 pp.
wood-polymer composites
Akad. Roln.
Posnan 60-637, Pol.
38
Degussa A.-G.
Czech.
Japan
Zhang, Qingyu
Loktionov, Yu. D.
USSR
Lubrifiants;
Fr.
USSR
Halliburton Co.
(4), 26-8
USA
U.S. US 4070865, 31 Jan 1978, 12 pp.
20. Polymeric pseudocrown ethers. 1. Synthesis and
Kapustina, I. B.
Minsk, USSR
Rehovot, Israel
James A.
Dynapol
Hatao Masato
Ambler, Michael R.
Japan
39
US 5,338,802 (1994).
US 6,465,595 B1 (2002).
40
Reprography
1. Aromatic Diolefinic Compounds, Aromatic Diethyl
Compounds and Electrographic Photoconductors
Comprising One Aromatic Diethyl Compound,
US 6,020,401 (2000).
US 4,886,846 (1989).
US 6,126,731 (2000).
US 6,210,474 B1 (2001).
US 5,575,954 (1996).
16. Aqueous Compositions Useful as Printing Vehicles,
US 5,616,364 (1997).
B1 (2001).
US 5,322,756 (1994).
21. Toner Compositions and Processes Thereof,
8. Dry Carrier Coating and Processes, Hadi K.
Mahabadi, (to Xerox Corporation),
US 5,330,874 (1994).
22. Method to Media Mill Particles Using Cross-linked
9. Binder Resin Used in a Toner, Yoshihiko Hiyousu,
(to Canon Kabushiki Kaisha), US 5,321,091 (1994).
10. Toner for Developing Electrostatic Image and
US 5,902,711 (1999).
US 5,998,076 (1999).
41
US 5,633,323 (1997).
US 5,268,430 (1993).
US 5,141,996 (1992).
US 5,792,815 (1998).
Star Polymers
1. Hydrogenated Star-Shaped Polymer, Rudolf J. A.
Eckert, (Shell Oil Company), US 4,116,917 (1978).
2. Hydrogenated Star-Shaped Polymer, Rudolf J. A.
Eckert, (Shell Oil Company), US 4,156,673 (1979).
US 5,919,870 (1999).
42
Customer Notice
43
DVB
Divinylbenzene
Cross-link a variety of materials
for improved thermal, physical,
and chemical properties
To learn more
In the U.S. and Canada,
call 1-800-447-4369 or fax 989-832-1465
In other areas of the world,
call 989-832-1560 or fax 989-832-1465
www.dow.com
NOTICE: No freedom from any patent owned by Seller or others is to be inferred. Because use conditions and applicable laws may differ from one
location to another and may change with time, Customer is responsible for determining whether products and the information in this document are
appropriate for Customers use and for ensuring that Customers workplace and disposal practices are in compliance with applicable laws and other
governmental enactment. Seller assumes no obligation or liability for the information in this document. NO WARRANTIES ARE GIVEN; ALL
IMPLIED WARRANTIES OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE ARE EXPRESSLY EXCLUDED.
Published January 2003
Printed in U.S.A.