US1058056A - Caoutchouc substances and process of making same. - Google Patents

Caoutchouc substances and process of making same. Download PDF

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Publication number
US1058056A
US1058056A US65853611A US1911658536A US1058056A US 1058056 A US1058056 A US 1058056A US 65853611 A US65853611 A US 65853611A US 1911658536 A US1911658536 A US 1911658536A US 1058056 A US1058056 A US 1058056A
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Prior art keywords
caoutchouc
substances
butadiene
making same
sodium
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Expired - Lifetime
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US65853611A
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Carl Harries
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Bayer AG
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Farbenfabriken Vorm Friedr Bayer and Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated

Definitions

  • alkali-forming metals namely, the alkali and alkaline earth metals,both in an isolated "state and in the form of their mixtures, al-
  • the vessel is closed and allowed to stand for a week or two.
  • the sodium is then destroyed by alcohol or water and the caoutchouc substance which has been formed is rolled into sheets.
  • It is an elastic whitish substance soluble inbenzene. It forms a nitrosite which is a yellowish powder which becomes brown and is decomposed on being heated to 140 C.
  • Its brom addition product is a whitish powder.
  • Its ozonid obtained with ozone (6-7 per cent.) is a colorless oil which detonates when heated:
  • the new caoutchouc substances are whitish substances soluble in benzene. They are free from protein substances which are always. contained in the natural caoutchouc and play an important part in it with regard to the elasticity of the natural caoutchouc. They form ozonids, nitrosites and brom addition products which are in the vulcanized form grayish, non-adhesive substances.
  • the new compounds thus obtained are different from the caoutchouc hitherto obtained from butadieneor its homologues, etc., and yield different derivatives.
  • the insoluble nitrosite for instance of the known isoprene caoutchouc (probably formula C H N O decomposes at about 120 C. the soluble one (formula of soluble.
  • benzene being free from protein substances and forming nitrosites; ozonids and brom addition products and in the vulcanized roac es form are whitish to grayish substances which are not adhesive and the ozonids of which on decomposition with water do not show the pyrrol test or show it only very weakly, substantially as described.
  • a new caoutchouc substance comprising butadiene caoutchouc obtained b treat- 3.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

UNITED STATES PATENT OFFICE.
CARL HARRIES, F KIEL, GERMANY, ASSIGNOR TO EARBENFABRIKEN VORM. FRIED-R. BAYEKGa 00., OF EL BEBFELD, GERMANY, A CORPORATION OF GERMANYU CAOUTCHOUO SUBSTANCES AND PROCESS OF MAKING SAME.
1,058,056. No Drawing.
Td'aZl whom it may concern:
Be it known that I, CARL HARRIES, professor of chemistry, doctor of philosophy, citizen of the German Empire, residing at Kiel, Germany, have invented new and useful Improvements in Caoutch-ouc Substances and Processes of Making Same, 0t which the following is a specification.
I have made the surprising discovery that the alkali-forming metals, namely, the alkali and alkaline earth metals,both in an isolated "state and in the form of their mixtures, al-
dium wire prepared in the usual way arepressed into 1000 parts of butadiene (condensed, by strong'cooling) having the. formula: v
tin
The vessel is closed and allowed to stand for a week or two. The sodium is then destroyed by alcohol or water and the caoutchouc substance which has been formed is rolled into sheets. It is an elastic whitish substance soluble inbenzene. It forms a nitrosite which is a yellowish powder which becomes brown and is decomposed on being heated to 140 C. Its brom addition product is a whitish powder. Its ozonid obtained with ozone (6-7 per cent.) is a colorless oil which detonates when heated: In
the vulcanized state it is whitish and nonadhesive. g
If in the example the quantity of sodium is replaced by 100 parts of sodium amalgam containing 10 per cent. of sodium, theproduct obtained from the mixture after several days standing is identical with the caoutchouc described in the exainple.
100 parts of isoprene are mixed with 3 parts of sodium and the mixture is heated in Specification of Letters Patent, Application med November 4, 1911. serial 1m 658,536.
the butadiene series,
Patented Apr. 8, 1913.
an autoclave to 36 C. for 6 weeks. The mass is then further treated as above described.
Instead of sodium, calcium, potassium, lithium'or mixtures of these metals such as calcium-sodium and instead of sodium amalgam other amalgams such as ammonium amalgam, etc., may be used. These metals, whether used in an isolated condition alone or in the form of mixtures or alloys or amalgams, are all embraced within the generic term,alkali-forming metals. Other hydrocarbons of the butadiene series can be employed e. g. alpha-methyL, alpha-alphadin1ethyl'-, beta-gamma-dimethyl-, gammametl1yl-, beta-isobutyl-, beta-normalpropyl butadiene, etc. I The new caoutchouc substances are whitish substances soluble in benzene. They are free from protein substances which are always. contained in the natural caoutchouc and play an important part in it with regard to the elasticity of the natural caoutchouc. They form ozonids, nitrosites and brom addition products which are in the vulcanized form grayish, non-adhesive substances.
The new compounds thus obtained are different from the caoutchouc hitherto obtained from butadieneor its homologues, etc., and yield different derivatives.
The insoluble nitrosite for instance of the known isoprene caoutchouc (probably formula C H N O decomposes at about 120 C. the soluble one (formula of soluble.
product C H N O decomposes at about 162 C. while the corresponding derivatives obtained from the products of the present application (probably formula of solubleproduct C 'H N O are not even -decomposed at 220 C. The ozonids show'characteristic diflierences. The decomposition products obtained by the action of water or 1. The process of producing caoutchouc of glacial acetic acid on the ozonids presubstances which comprises subjecting hydrocarbons of the'butadiene series to the action of an alkali-forming metal.
2. The process of producing caoutchouc substances which comprises subjecting. hy-
drocarbons of the butadiene series to the action of an alkali metal.
substances which comprises subjecting hydrocarbons of the butadiene series to the action,- of sodium.
4.. The process of producing caoutchouc substances which comprises subjecting butadiene to the action of an alkaliforming metal.
5. The process of producing caoutchouc substances which comprises subjecting butadiene to the action of an alkali metal.
6. The process of producing caoutchouc substances which comprises subjecting butadiene to the action of sodium.
benzene, being free from protein substances and forming nitrosites; ozonids and brom addition products and in the vulcanized roac es form are whitish to grayish substances which are not adhesive and the ozonids of which on decomposition with water do not show the pyrrol test or show it only very weakly, substantially as described.
8. A new caoutchouc substance comprising butadiene caoutchouc obtained b treat- 3. The process of producing caoutchouc ment of butadiene with an alkali orming metal which is a whitish substance soluble in beiizene, forming a nitrosite which is a yellowish powder which becomes brown and is decomposed on being heated to 140 0.; forming a brom addition product which is a whitish powder, forming an ozonid which is a colorless oil detonating when heated and which on decomposition withwater does not show the 'pyrrol test or shows it only very weakly; and in the vulcanized form is a whitish not adhesive powder, substantially as described.
In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.
CARL HARRIES.
Witnesses:
JULIUS Borne, Fmnnmon Burrow.
US65853611A 1911-11-04 1911-11-04 Caoutchouc substances and process of making same. Expired - Lifetime US1058056A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2458378A (en) * 1946-01-07 1949-01-04 Phillips Petroleum Co Process of separating metallic sodium from high molecular weight polymers made by polymerization of vinyl compounds
US2856391A (en) * 1956-01-09 1958-10-14 Goodrich Co B F Polymerization of 2-substituted butadiene-1,3 hydrocarbons with a catalyst comprising a lithium alkoxide and an alkenyl lithium compound
US2908672A (en) * 1957-03-21 1959-10-13 Du Pont Polymerization of conjugated diolefins with a catalyst consisting of a binary alloy of a group ii-a metal and lithium
US2908673A (en) * 1957-03-21 1959-10-13 Du Pont Polymerization of conjugated diolefins with a catalyst consisting of a binary alloy of a group h-a metal and a group iii-a metal
US2913444A (en) * 1956-01-09 1959-11-17 Goodrich Co B F Process for polymerizing conjugated diolefins using a mixture of metallic lithium and alkyl lithium as the catalyst
US2947737A (en) * 1956-02-08 1960-08-02 Firestone Tire & Rubber Co Polymerization of conjugated diolefines with a catalyst comprising metallic lithium dispersed in a crystalline salt
US3004012A (en) * 1958-02-05 1961-10-10 Du Pont Catalytic process for polymerizing chloroprene to a solid elastomer
US3004011A (en) * 1958-02-05 1961-10-10 Du Pont Catalytic process for polymerizing chloroprene to a solid elastomer
US3049528A (en) * 1958-12-30 1962-08-14 Goodrich Co B F Polymerization of butadiene-1, 3 hydrocarbons
US3050513A (en) * 1955-10-17 1962-08-21 Phillips Petroleum Co Process and catalyst for production of rubbery polymers
US3114743A (en) * 1954-12-02 1963-12-17 Goodrich Gulf Chem Inc Method of preparing synthetic rubber

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2458378A (en) * 1946-01-07 1949-01-04 Phillips Petroleum Co Process of separating metallic sodium from high molecular weight polymers made by polymerization of vinyl compounds
US3114743A (en) * 1954-12-02 1963-12-17 Goodrich Gulf Chem Inc Method of preparing synthetic rubber
US3050513A (en) * 1955-10-17 1962-08-21 Phillips Petroleum Co Process and catalyst for production of rubbery polymers
US2856391A (en) * 1956-01-09 1958-10-14 Goodrich Co B F Polymerization of 2-substituted butadiene-1,3 hydrocarbons with a catalyst comprising a lithium alkoxide and an alkenyl lithium compound
US2913444A (en) * 1956-01-09 1959-11-17 Goodrich Co B F Process for polymerizing conjugated diolefins using a mixture of metallic lithium and alkyl lithium as the catalyst
US2947737A (en) * 1956-02-08 1960-08-02 Firestone Tire & Rubber Co Polymerization of conjugated diolefines with a catalyst comprising metallic lithium dispersed in a crystalline salt
US2908672A (en) * 1957-03-21 1959-10-13 Du Pont Polymerization of conjugated diolefins with a catalyst consisting of a binary alloy of a group ii-a metal and lithium
US2908673A (en) * 1957-03-21 1959-10-13 Du Pont Polymerization of conjugated diolefins with a catalyst consisting of a binary alloy of a group h-a metal and a group iii-a metal
US3004012A (en) * 1958-02-05 1961-10-10 Du Pont Catalytic process for polymerizing chloroprene to a solid elastomer
US3004011A (en) * 1958-02-05 1961-10-10 Du Pont Catalytic process for polymerizing chloroprene to a solid elastomer
US3049528A (en) * 1958-12-30 1962-08-14 Goodrich Co B F Polymerization of butadiene-1, 3 hydrocarbons

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