DE1273823B - Process for the production of liquid 2-chlorobutadiene (1, 3) polymers - Google Patents

Process for the production of liquid 2-chlorobutadiene (1, 3) polymers

Info

Publication number
DE1273823B
DE1273823B DE1962P0029204 DEP0029204A DE1273823B DE 1273823 B DE1273823 B DE 1273823B DE 1962P0029204 DE1962P0029204 DE 1962P0029204 DE P0029204 A DEP0029204 A DE P0029204A DE 1273823 B DE1273823 B DE 1273823B
Authority
DE
Germany
Prior art keywords
chlorobutadiene
polymers
liquid
polymerization
production
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DE1962P0029204
Other languages
German (de)
Inventor
Kenneth Leron Miller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of DE1273823B publication Critical patent/DE1273823B/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C08F36/14—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 containing elements other than carbon and hydrogen
    • C08F36/16—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 containing elements other than carbon and hydrogen containing halogen
    • 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
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—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
    • C08F236/04—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
    • C08F236/14—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 containing elements other than carbon and hydrogen
    • C08F236/16—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 containing elements other than carbon and hydrogen containing halogen

Description

BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES vlfffttisk PATENTAMT FEDERAL REPUBLIC OF GERMANY GERMAN vlfffttisk PATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. CL:Int. CL:

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

C08fC08f

C08dC08d

Deutsche Kl.: 39 c-25/05 German class: 39 c -25/05

P 12 73 823.7-44 (P 29204) P 12 73 823.7-44 (P 29204)

17. April 1962April 17, 1962

25. Juli 1968July 25, 1968

Die Patentanmeldung P 26804 IVd/39c (deutsche Auslegeschrift 1 266 980) betrifft ein Verfahren zur Herstellung von flüssigen 2-Chlorbutadien-(l,3)-Polymerisaten durch Polymerisation eines Chloropren-Monomeren allein oder im Gemisch mit einem geringeren Anteil eines damit mischpolymerisierbaren Monomeren in wäßriger Emulsion in Gegenwart eines Dialkylxanthogendisulfids der Formel "The patent application P 26804 IVd / 39c (German Auslegeschrift 1 266 980) relates to a method for Production of liquid 2-chlorobutadiene (l, 3) polymers by polymerizing a chloroprene monomer alone or in a mixture with a smaller proportion of one which is copolymerizable therewith Monomers in aqueous emulsion in the presence of a dialkylxanthogen disulfide of the formula "

Ri-ORi-O

S-C-O-R2 SCOR 2

in der Ri und' R2 Alkylreste mit 1 bis 8 Kohlenstoffatomen bedeuten, das dadurch gekennzeichnet ist, daß man die Emulsionspolymerisation des Chloropren-Monomeren allein oder im Gemisch mit einem geringeren Anteil eines damit mischpolymerisierbaren Monomeren, vorzugsweise 2,3-Dichlorbutadien-(l,3), in Gegenwart von 5 bis 18 Gewichtsteilen Dialkylxanthogendisulfid je 100 Teile Monomeres durchführt und die Polymerisation abbricht, wenn ein Polymerisat mit einer Brookfield-Viskosität zwischen 30 00OcP bei 210C und 400 00OcP bei 50C entstanden ist.in which Ri and 'R 2 denote alkyl radicals with 1 to 8 carbon atoms, which is characterized in that the emulsion polymerization of the chloroprene monomer alone or in a mixture with a smaller proportion of a monomer copolymerizable therewith, preferably 2,3-dichlorobutadiene (l , 3), in presence of 5 to 18 parts by weight per 100 parts dialkylxanthogen disulfide performs monomer and the polymerization terminates when a polymer is formed having a Brookfield viscosity between 30 00OcP at 21 0 C and 400 00OcP at 50C.

Es hat sich nun herausgestellt, daß es nicht erforderlich ist, die Polymerisation bzw. Mischpolymerisation des Chloropren-Monomeren in Gegenwart von Dialkylxanthogendisulfid so durchzuführen, daß ein Polymerisat mit einer oberen Viskositätsgrenze von 400 00OcP bei 500C gewonnen wird, sondern daß man besonders günstige Ergebnisse erzielt, wenn man die Polymerisation bzw. Mischpolymerisation unter solchen Bedingungen vornimmt, daß ein Polymerisat mit einer Brookfield-Viskosität bis zu 500 000 bis 550 000 cP bei 5O0C gewonnen wird.It has now been found that it is not necessary to perform the polymerization or copolymerization of chloroprene monomers in the presence of dialkyl xanthogen so that a polymer having an upper viscosity limit of 400 00OcP is obtained at 50 0 C, but that particularly favorable achieved results when the polymerization is carried or copolymerization under such conditions that a polymer having a Brookfield viscosity is obtained up to 500,000 to 550,000 cps at 5O 0 C.

Das erfindungsgemäße Verfahren zur Herstellung von flüssigen 2-Chlorbutadien-( 1,3 ^Polymerisaten durch Polymerisation eines Chloropren-Monomeren allein oder im Gemisch mit einem geringeren Anteil eines damit mischpolymerisierbaren Monomeren, vorzugsweise 2,3-Dichlorbutadien-(l,3), in wäßriger Emulsion in Gegenwart von 5 bis 18 Gewichtsteilen eines Dialkylxanthogendisulfids der FormelThe inventive method for the preparation of liquid 2-chlorobutadiene (1,3 ^ polymers by polymerizing a chloroprene monomer alone or in a mixture with a smaller proportion a monomer copolymerizable therewith, preferably 2,3-dichlorobutadiene- (1,3), in aqueous Emulsion in the presence of 5 to 18 parts by weight of a dialkylxanthogen disulfide of the formula

R1-O-C-S-S-C-O-R2 R 1 -OCSSCOR 2

S SS S

in der Ri und R2 Alkylreste mit 1 bis 8 Kohlenstoffatomen bedeuten, je 100 Teile Monomeres, nach Patentanmeldung P 26804 IVd/39c (deutsche Auslegeschrift 1 266 980). besteht darin, daß man die Polymerisation abbricht, wenn ein Polymerisat mit Verfahren zur Herstellung von flüssigen 2-Chlorbutadien-(l,3)-Polymerisatenin which Ri and R2 are alkyl radicals with 1 to 8 carbon atoms mean, per 100 parts of monomer, according to patent application P 26804 IVd / 39c (German Auslegeschrift 1,266,980). is that you stop the polymerization if a polymer with Process for the production of liquid 2-chlorobutadiene (1,3) polymers

Zusatz zur Anmeldung: P 26804IV d/39 c Auslegeschrift 1266 980Addition to registration: P 26804IV d / 39 c Auslegeschrift 1266 980

Anmelder:Applicant:

E. I. du Pont de Nemours and Company, Wilmington, Del. (V. St. A.)E.I. du Pont de Nemours and Company, Wilmington, Del. (V. St. A.)

Vertreter:Representative:

Dr.-Ing. W. Abitz, Patentanwalt, 8000 München 27, Pienzenauer Str. 28Dr.-Ing. W. Abitz, patent attorney, 8000 Munich 27, Pienzenauer Str. 28

Als Erfinder benannt:
Kenneth Leron Miller,
Lyndon, Ky. (V. St. A.)Named as inventor:
Kenneth Leron Miller,
Lyndon, Ky. (V. St. A.)

Beanspruchte Priorität:Claimed priority:

V. St. v. Amerika vom 24. April 1961 (104 853)V. St. v. America April 24, 1961 (104 853)

einer Brookfield-Viskosität zwischen 400 000 und 000 bis 550 000 cP bei 5OC entstanden ist.a Brookfield viscosity between 400,000 and 000 to 550,000 cP at 5OC.

Beispielexample

Ein Polymerisat wird gemäß Beispiel 1 der Hauptpatentanmeldung, jedoch aus den folgenden Ausgangsstoffen hergestellt:A polymer is made according to Example 1 of the main patent application, but from the following starting materials manufactured:

ChloroprenlÖSUng GewichtsteileChloroprene SOLUTION Parts by weight

2-Chlorbutadien-(l,3) 92,502-chlorobutadiene- (1,3) 92.50

2,3-Dichlorbutadien-(l,3) 7,502,3-dichlorobutadiene- (1,3) 7.50

Disproportioniertes Kolophonium .. 4,00Disproportionate rosin .. 4.00

Dodecylmercaptan 0,20Dodecyl mercaptan 0.20

Diisopropylxanthogendisulfid 5,50Diisopropylxanthogen disulfide 5.50

Wäßrige LösungAqueous solution

Wasser 149,00Water 149.00

Natriumhydroxyd 0,15Sodium hydroxide 0.15

Ammoniumhydroxyd (28%) 0.83Ammonium hydroxide (28%) 0.83

Als Katalysator dient (erstens) eine Lösung, die 5"/o Kaliumpersulfat und 0,15% Natrium-2-anthrachinon-The catalyst used is (firstly) a solution which is 5 "/ o Potassium persulfate and 0.15% sodium 2-anthraquinone

809 587/547809 587/547

sulfonat enthält, und (zweitens) eine 10%ige Natriumhydrosulfitlösung. Beide Lösungen werden dem Polymerisationsgemisch in gesonderten Strömen zugeführt. Das Produkt hat eine Brookfield-Viskosität von 540 000 cP bei 5O0C.contains sulfonate, and (second) a 10% sodium hydrosulfite solution. Both solutions are fed to the polymerization mixture in separate streams. The product has a Brookfield viscosity of 540 000 cps at 5O 0 C.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von flüssigen , 2-Chlorbutadien-(l,3)-Polymerisaten durch Polymerisation eines Chloropren-Monomeren allein oder im Gemisch mit einem geringeren Anteil eines damit mischpolymerisierbaren Monomeren, vorzugsweise 2,3-Dichlorbutadien-(l,3), in wäßriger Emulsion in Gegenwart von 5 bis 18 Gewichtsteilen eines Dialkylxanthogendisulfids der FormelProcess for the production of liquid 2-chlorobutadiene (1,3) polymers by polymerization a chloroprene monomer alone or in a mixture with a smaller proportion of a monomer copolymerizable therewith, preferably 2,3-dichlorobutadiene- (1,3), in an aqueous emulsion in the presence of 5 to 18 parts by weight a dialkylxanthogen disulfide of the formula Ri- O — C — S — S — C — O — R2 R - O - C - S - S - C - O - R 2 in der Ri und R2 Alkylreste mit 1 bis 8 Kohlenstoffatomen bedeuten, je 100 Teile Monomeres, nach Patentanmeldung P 26804IV d/39c (deutsche Auslegeschrift 1 266980), dadurch gekennzeichnet, daß man die Polymerisation abbricht, wenn ein Polymerisat mit einer Brookfield-Viskosität zwischen 400 000 und 500 000 bis 550 00OcP bei 500C entstanden ist.in which R 1 and R 2 are alkyl radicals with 1 to 8 carbon atoms, 100 parts of monomer each, according to patent application P 26804IV d / 39c (German Auslegeschrift 1 266980), characterized in that the polymerization is terminated when a polymer with a Brookfield viscosity between 400 000 and 500 000 came to 550 00OcP at 50 0 C. ei» »7/547 7. M β Bundewfcuckerei Berlinei »» 7/547 7. M β Bundewfcuckerei Berlin
DE1962P0029204 1960-03-23 1962-04-17 Process for the production of liquid 2-chlorobutadiene (1, 3) polymers Pending DE1273823B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1696060A 1960-03-23 1960-03-23
US10485361A 1961-04-24 1961-04-24

Publications (1)

Publication Number Publication Date
DE1273823B true DE1273823B (en) 1968-07-25

Family

ID=30447787

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1962P0029204 Pending DE1273823B (en) 1960-03-23 1962-04-17 Process for the production of liquid 2-chlorobutadiene (1, 3) polymers

Country Status (3)

Country Link
DE (1) DE1273823B (en)
GB (1) GB963075A (en)
NL (1) NL276915A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5039703B2 (en) * 1973-05-17 1975-12-18
US4054731A (en) 1973-05-17 1977-10-18 Denki Kagaku Kogyo Kabushiki Kaisha Process for curing liquid chloroprene polymer containing xanthate active terminal groups using polyfunctional amines
US5357010A (en) * 1988-04-08 1994-10-18 Enichem Elastomeres France Sa Process for the preparation of a polychloroprene polymer
FR2629826B1 (en) * 1988-04-08 1991-01-18 Distugil PROCESS FOR PRODUCING POLYCHLOROPRENE

Also Published As

Publication number Publication date
NL276915A (en) 1964-10-26
GB963075A (en) 1964-07-08

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Legal Events

Date Code Title Description
E77 Valid patent as to the heymanns-index 1977