NO153060B - PROCEDURE FOR PREPARING BITUMEN-POLYMER MIXTURES - Google Patents
PROCEDURE FOR PREPARING BITUMEN-POLYMER MIXTURES Download PDFInfo
- Publication number
- NO153060B NO153060B NO793609A NO793609A NO153060B NO 153060 B NO153060 B NO 153060B NO 793609 A NO793609 A NO 793609A NO 793609 A NO793609 A NO 793609A NO 153060 B NO153060 B NO 153060B
- Authority
- NO
- Norway
- Prior art keywords
- weight
- bitumen
- carboxylated
- polymer
- styrene
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 5
- 239000010426 asphalt Substances 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 9
- 229920001400 block copolymer Polymers 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 230000035515 penetration Effects 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- -1 carboxyl isoprene- Chemical compound 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Working-Up Tar And Pitch (AREA)
Description
Norsk utlegningsskrift nr. 151089 beskriver en fremgangs- Norwegian interpretation document no. 151089 describes a progress
måte ved fremstilling av blandinger av bitumen og polymerer som består av å bringe i kontakt ved en temperatur mellom 130 og 230^C 80-98 vekt-% av et bitumen med penetrasjon mellom 30 og 220 og 2-20 vekt-0/ av en styren/konjugert dien-blokk-kopolymer med midlere molekylvekt mellom 30 000 way in the production of mixtures of bitumen and polymers which consists of bringing into contact at a temperature between 130 and 230°C 80-98% by weight of a bitumen with penetration between 30 and 220 and 2-20% by weight of a styrene/conjugated diene block copolymer with average molecular weight between 30,000
og 300 000, holde den oppnådde blanding under røring i minst 2 timer, deretter tilsette 0,1-3 vekt-% elementært svovel i forhold til bitumenet og opprettholde røringen av blandingen som derved er oppnådd, i minst 20 min. for å and 300,000, keep the mixture obtained under stirring for at least 2 hours, then add 0.1-3% by weight elemental sulfur in relation to the bitumen and maintain the stirring of the mixture thus obtained for at least 20 min. in order to
oppnå vulkanisering in situ av kopolymeren. achieve in situ vulcanization of the copolymer.
Dienkomponenten i kopolymerene som beskrives i dette utleggningsskrift, er hovedsaklig butadien. The diene component in the copolymers described in this specification is mainly butadiene.
Foreliggende oppfinnelse utgjør en forbedring av denne fremgangsmåte ved fremstilling av bitumen-polymer- The present invention constitutes an improvement of this method in the production of bitumen-polymer
blandinger, hvorved 80-98 vekt-% av et bitumen blandes med 2-20 vekt-% av en styren/konjugert dien-blokk-kopolymer under tilsetning av 0,1-3 vekt-% elementært svovel i forhold til bitumen, og fremgangsmåten er karakterisert ved at man som dienkomponent anvender karboksylert butadien eller karboksylert isopren. mixtures, whereby 80-98% by weight of a bitumen is mixed with 2-20% by weight of a styrene/conjugated diene block copolymer with the addition of 0.1-3% by weight elemental sulfur relative to the bitumen, and the method is characterized by using carboxylated butadiene or carboxylated isoprene as the diene component.
De karboksylerte polystyren-polyisopren- eller karboksylerte polystyren-polubutadien-blokk-kopolymerer er fortrinnsvis disekvens-kopolymerer med et innhold av polystyren som ligger mellom 15 og 25 vekt%. The carboxylated polystyrene-polyisoprene or carboxylated polystyrene-polybutadiene block copolymers are preferably disequence copolymers with a polystyrene content of between 15 and 25% by weight.
Deres molekylvekt er fortrinnsvis mellom 70 000 og 90 000. Their molecular weight is preferably between 70,000 and 90,000.
Innholdet av karboksylgrupper ligger fortrinnsvis mellom The content of carboxyl groups is preferably between
0.05 og 0,1 vekt-% i forhold til polymeren. 0.05 and 0.1% by weight in relation to the polymer.
Karboksylgruppene sitter fortrinnsvis i endene av polydienkjedene og kan innføres enten gjennom omsetning av endene med CO^ ved anionisk polymerisasjon eller ved maleinreaksjon eller oppvarming av den ikke-karboksylerte The carboxyl groups are preferably at the ends of the polydiene chains and can be introduced either through reaction of the ends with CO^ by anionic polymerization or by male reaction or heating of the non-carboxylated
polymer med akrylsyre. polymer with acrylic acid.
Vulkaniseringen in situ av en karboksylert disekvens-polystyren-polybutadien-kopolymer i bitumen gir forbedrede elastomere egenskaper ved kulde samtidig som produktet beholder en viskositet ved varme som er nær identisk med et bitumen-produkt på basis av disekvens-polystyren-polybutadien-kopolymer. The in-situ vulcanization of a carboxylated di-sequence polystyrene-polybutadiene copolymer in bitumen provides improved elastomeric properties in the cold while the product retains a viscosity in heat that is almost identical to a bitumen product based on di-sequence polystyrene-polybutadiene copolymer.
Disse forbedringer kan forklares ved at den doble kryssbinding som foreligger mellom polymerkjedene. Den ene, som er reversibel, kommer av karboksylgruppene i polymeren som danner salter med metall-ionene som foreligger i bitumenet (Fe, Ni, V) når blandingstemperaturen svekker overføringen av ikke-elastomere di-blokk-kjeder til elastomere poly-blokk-kjeder. These improvements can be explained by the double cross-linking that exists between the polymer chains. One, which is reversible, comes from the carboxyl groups in the polymer forming salts with the metal ions present in the bitumen (Fe, Ni, V) when the mixing temperature weakens the transfer of non-elastomeric di-block chains to elastomeric poly-block chains .
Den andre, som er irreversibel, fremkommer ved de svovelbroer som skapes mellom polymerkjedene hvis nærvær bibeholdes ved høyere temperaturer. The other, which is irreversible, arises from the sulfur bridges that are created between the polymer chains whose presence is maintained at higher temperatures.
Den doble kryssbinding som fremskynder bitumenets elastomere egenskaper tillater således å redusere andelen av polymerer som skal til for å oppnå nødvendige egenskaper for å tilfredstille driftsbetingelsene ved den tilsiktede bruk og vil derfor ha en direkte innflytelse på produktets fabrikasjonspris. The double cross-linking that accelerates the bitumen's elastomeric properties thus allows to reduce the proportion of polymers needed to achieve the necessary properties to satisfy the operating conditions of the intended use and will therefore have a direct influence on the product's manufacturing price.
Reversibiliteten av den ioniske kryssbindingen muliggjør en lettere benyttelse av produktet fordi det bibeholdes en viskositet som er identisk med den som oppnås ved en ikke-karboksylisk disekvenskopolymer som anvendes i samme mengde. The reversibility of the ionic cross-linking enables an easier use of the product because a viscosity is maintained which is identical to that obtained by a non-carboxylic disequence copolymer used in the same amount.
De følgende eksempler belyser forbedringen av egenskaper som oppnås ved å tilsette karboksylerte styren-isopren- The following examples illustrate the improvement in properties achieved by adding carboxylated styrene-isoprene-
og styren-butadien-kopolymere. and styrene-butadiene copolymers.
SAMMENLIGNINGSEKSEMPEL 1 COMPARISON EXAMPLE 1
Man blander 100 deler av en bitumen 80-100 med en Bille et Anneau-temperatur på 48°C og et Fraass-punkt på -18°C og 10 deler av en isopren-styren-disekvenskopolymer med midlere molekylvekt 80 000 og forhold isopren , ., 3. One mixes 100 parts of a bitumen 80-100 with a Bille et Anneau temperature of 48°C and a Fraass point of -18°C and 10 parts of an isoprene-styrene disequence copolymer with an average molecular weight of 80,000 and a ratio of isoprene, ., 3.
_, J_ lic j • _, J_ lic j •
styren styrene
Man holder blandingen på 17 0°C i 3 timer 3 0 min. under røring, tilsetter 0,2 deler elementært svovel og fortsetter røringen i en halv time. The mixture is kept at 170°C for 3 hours 30 minutes. while stirring, add 0.2 parts of elemental sulfur and continue stirring for half an hour.
De karakteristiske egenskaper hos den erholdte bitumen-polymer fremgår av tabell I. The characteristic properties of the obtained bitumen polymer appear in table I.
SAMMENLIGNINGSEKSEMPEL 2 COMPARISON EXAMPLE 2
Man gjentar sammenligningseksempel 1 under utelatelse av tilsetning av svovel og holder blandingen under røring i 4 timer. Man fastslår at blandingen er ubestandig ved strekk-prøver ved -10°C i 10 mm/mn. Comparative example 1 is repeated, omitting the addition of sulphur, and the mixture is kept under stirring for 4 hours. It is established that the mixture is unstable in tensile tests at -10°C for 10 mm/min.
EKSEMPEL I EXAMPLE I
Man går frem som i sammenligningseksempel 1, men erstatter One proceeds as in comparison example 1, but replaces
i disekvenskopolymeren isoprensekvensen med en karboksylert butadiensekvens, hvilket bedrer de elastiske egenskaper som man kan se av tabell I. Karboksyl-gruppeinnholdet ligger mellom 0,05 og 0,1 vekt-% i forhold til polymeren. in the disequence copolymer the isoprene sequence with a carboxylated butadiene sequence, which improves the elastic properties as can be seen from Table I. The carboxyl group content is between 0.05 and 0.1% by weight in relation to the polymer.
SAMMENLIGNINGSEKSEMPEL 3 COMPARISON EXAMPLE 3
Dette eksempelet er en sammenligning med eksempel I, hvor sistnevnte gjentas uten vulkanisering in situ, dvs. ved utelatelse av tilsetting av elementært svovel. This example is a comparison with example I, where the latter is repeated without vulcanization in situ, i.e. by omitting the addition of elemental sulphur.
Man fastslår som tilsynelatende ubestandighet for strekk- It is determined as apparent instability for tensile
prøver ved -10°C 500 mrr/mn. samples at -10°C 500 mrr/mn.
EKSEMPEL II EXAMPLE II
Fordi de forbedrede elastiske egenskaper oppnås ved karboksylert butadien i enden av kjeden, går man frem som i de foregående eksempler men innfører en mindre andel av ko- Because the improved elastic properties are achieved by carboxylated butadiene at the end of the chain, one proceeds as in the previous examples but introduces a smaller proportion of co-
A S M A.-S 15.000 6 84 A S M A.-S 15,000 6 84
polymer: bare 3 %. polymer: only 3%.
SAMMENLIGNINGSEKSEMPEL 4 COMPARISON EXAMPLE 4
Man arbeider i sammenligning med eksempel II med en andel In comparison with example II, one works with a proportion
på 3 % av en ikke-karboksylert styren-butadien-kopolymer. of 3% of a non-carboxylated styrene-butadiene copolymer.
Slike produkter som man oppnår innenfor rammen av foreliggende oppfinnelse er produkter med en sterk elastisk karakter og et betydelig plastisitetsinterval hvilket fører til spesielt inter-essante egenskaper slik at man kan bruke dem: - for fremstilling av skotøy og industriell bekledning (over-trekk, overflatebelegg, asfaltbelegg, - for nevnte industrielle applikasjoner slik som tetninger (be-legg, filt, takspon, maling, produkter for bilunderstell, produkter for termisk-, elektrisk- og lydisolasjon.) Such products that are obtained within the framework of the present invention are products with a strong elastic character and a significant plasticity interval, which leads to particularly interesting properties so that they can be used: - for the production of footwear and industrial clothing (overcoats, surface coatings , asphalt coating, - for mentioned industrial applications such as seals (coating, felt, roofing shavings, paint, products for car chassis, products for thermal, electrical and sound insulation.)
EKSEMPEL III EXAMPLE III
Man fremstiller en blanding av 100 deler bitumen 80-100 med A mixture of 100 parts bitumen 80-100 med
en Ball og Ring temperatur på 48°C og Fraas-punkt på a Ball and Ring temperature of 48°C and Fraas point on
-18°C, og 10 deler av en styreri/karboksyler isopren- -18°C, and 10 parts of a styrene/carboxyl isoprene-
kopolymer inneholdende 0,55 vekt-% karboksylgrupper (i forhold til kopolymerens vekt) og med et vektforhold lik 3 copolymer containing 0.55% by weight carboxyl groups (in relation to the weight of the copolymer) and with a weight ratio equal to 3
mellom karboksylert isopren og styren. Blandingen blir viderebehandlet som i sammenligningseksempel 1. between carboxylated isoprene and styrene. The mixture is further processed as in comparative example 1.
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7831689A FR2440967A2 (en) | 1976-12-28 | 1978-11-09 | Bitumen-polymer compsn. for road and industrial coatings etc. - contains styrene!-conjugated diene! copolymer and sulphur |
Publications (3)
Publication Number | Publication Date |
---|---|
NO793609L NO793609L (en) | 1980-05-12 |
NO153060B true NO153060B (en) | 1985-09-30 |
NO153060C NO153060C (en) | 1986-01-08 |
Family
ID=9214660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO793609A NO153060C (en) | 1978-11-09 | 1979-11-08 | PROCEDURE FOR PREPARING BITUMEN-POLYMER MIXTURES |
Country Status (14)
Country | Link |
---|---|
JP (1) | JPS5831107B2 (en) |
AT (1) | AT369778B (en) |
BE (1) | BE879847A (en) |
BR (1) | BR7907255A (en) |
CA (1) | CA1137243A (en) |
CH (1) | CH643282A5 (en) |
DE (1) | DE2945365C2 (en) |
DK (1) | DK168074B1 (en) |
ES (1) | ES485814A1 (en) |
GB (1) | GB2038848A (en) |
IT (1) | IT1127205B (en) |
NL (1) | NL188044C (en) |
NO (1) | NO153060C (en) |
SE (1) | SE437529B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3037829C2 (en) * | 1980-10-07 | 1983-08-25 | Rütgerswerke AG, 6000 Frankfurt | Process for the production of modified pitches and low-boiling aromatics or olefins and the use of these pitches |
JPS57139143A (en) * | 1981-02-23 | 1982-08-27 | Asahi Chem Ind Co Ltd | Bituminous composition |
US4485201A (en) * | 1983-11-21 | 1984-11-27 | Midwest Elastomers, Inc. | Method of modifying asphalt with thermoplastic polymers, ground rubber and composition produced |
US4933384A (en) * | 1986-01-10 | 1990-06-12 | The Dow Chemical Company | Bituminous materials |
US5270361A (en) * | 1992-02-25 | 1993-12-14 | Bitumar R. & D. (2768836 Canada Inc.) | Asphalt composition and process for obtaining same |
GB2305667A (en) * | 1995-09-27 | 1997-04-16 | Lawrence Lester | Bitumen-polymer compositions |
CA2359173A1 (en) | 1999-01-27 | 2000-08-03 | Polyphalt Inc. | Modified bituminous composition for roof membranes |
EA021407B1 (en) * | 2010-02-23 | 2015-06-30 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Bituminous composition |
US9249304B2 (en) | 2013-11-01 | 2016-02-02 | Saudi Arabian Oil Company | Heavy oil ash in roofing, damp-proofing, and water proofing applications |
US9637635B2 (en) | 2013-11-01 | 2017-05-02 | Saudi Arabian Oil Company | Sulfur asphalt in roofing, damp-proofing and water proofing |
WO2015066567A1 (en) * | 2013-11-01 | 2015-05-07 | Saudi Arabian Oil Company | Sulfur asphalt in roofing, damp-proofing and water proofing |
US9309441B2 (en) | 2013-11-01 | 2016-04-12 | Saudi Arabian Oil Company | Sulfur asphalt in roofing, damp-proofing and water proofing |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2376188A1 (en) * | 1976-12-28 | 1978-07-28 | Elf Union | PROCESS FOR PREPARING COMPOSITIONS OF POLYMERIC BITUMES |
-
1979
- 1979-11-06 BE BE0/197982A patent/BE879847A/en not_active IP Right Cessation
- 1979-11-07 GB GB7938486A patent/GB2038848A/en not_active Expired - Lifetime
- 1979-11-08 SE SE7909260A patent/SE437529B/en not_active IP Right Cessation
- 1979-11-08 JP JP54144912A patent/JPS5831107B2/en not_active Expired
- 1979-11-08 BR BR7907255A patent/BR7907255A/en not_active IP Right Cessation
- 1979-11-08 CH CH1000679A patent/CH643282A5/en not_active IP Right Cessation
- 1979-11-08 NO NO793609A patent/NO153060C/en unknown
- 1979-11-08 DK DK472979A patent/DK168074B1/en not_active IP Right Cessation
- 1979-11-08 IT IT27120/79A patent/IT1127205B/en active
- 1979-11-08 AT AT0718479A patent/AT369778B/en not_active IP Right Cessation
- 1979-11-08 CA CA000339463A patent/CA1137243A/en not_active Expired
- 1979-11-08 ES ES485814A patent/ES485814A1/en not_active Expired
- 1979-11-09 DE DE2945365A patent/DE2945365C2/en not_active Expired
- 1979-11-09 NL NLAANVRAGE7908230,A patent/NL188044C/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
GB2038848A (en) | 1980-07-30 |
JPS5569650A (en) | 1980-05-26 |
SE7909260L (en) | 1980-05-10 |
ES485814A1 (en) | 1980-05-16 |
NO153060C (en) | 1986-01-08 |
NL7908230A (en) | 1980-05-13 |
AT369778B (en) | 1983-01-25 |
NO793609L (en) | 1980-05-12 |
DE2945365C2 (en) | 1984-03-15 |
NL188044B (en) | 1991-10-16 |
NL188044C (en) | 1992-03-16 |
IT7927120A0 (en) | 1979-11-08 |
SE437529B (en) | 1985-03-04 |
IT1127205B (en) | 1986-05-21 |
DK168074B1 (en) | 1994-01-31 |
DK472979A (en) | 1980-05-10 |
DE2945365A1 (en) | 1980-05-22 |
CA1137243A (en) | 1982-12-07 |
BR7907255A (en) | 1980-07-08 |
CH643282A5 (en) | 1984-05-30 |
BE879847A (en) | 1980-03-03 |
JPS5831107B2 (en) | 1983-07-04 |
ATA718479A (en) | 1982-06-15 |
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