Homo- or copolymers of 1,3-dienes carrying reactive silyl groups, their preparation and use

• US 4,381,377 A
• Filed: 02/02/1981
• Issued: 04/26/1983
• Est. Priority Date: 02/02/1980
• Status: Expired due to Fees

• Current Assignee: Chemische Werke Huls Aktiengesellschaft
• Original Assignee: Chemische Werke Huls Aktiengesellschaft
• Inventors: Streck, Roland, Kampf, Wolfgang, Haag, Horst-guenter
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US06/230,483
• Time in Patent Office: 813 Days
• Field of Search: 556/482, 556/465, 556/446, 556/486, 556/442, 556/422, 556/419, 556/489, 525/375
• US Class Current: 525/375
• CPC Class Codes: C08C 19/25 Incorporating silicon atoms into the molecule
• CPC Class Codes: C08C 19/28 Reaction with compounds containing carbon-to-carbon unsaturated bonds graft polymers C08F279/00
• CPC Class Codes: C08K 9/06 with silicon-containing compounds

Abstract

A homo- or copolymer of a 1,3-diene bound to reactive silyl groups, whereby it contains 0.4-12% by weight of bound silicon, is prepared by reacting, at a temperature of 190°-300° C., a 1,3-diene homo- or copolymer, with more than 1% of its aliphatic double bonds in conjugation and having a molecular weight (Mn) of 400-6,000, with a silane of the formula ##STR1## wherein R is an unsaturated aliphatic hydrocarbon radical of 2-20 carbon atoms,

X is halogen, C_1-6 alkoxy, C_1-6 alkoxyalkoxy, C_6-12 aryloxy, C_1-8 alkanoyloxy, C_1-6 ketoximato or C_1-10 hydrocarbylamido, and

Y and Z are independently one of the X groups, hydrogen, alkyl of 1-8 carbon atoms, cycloalkyl of 5-12 carbon atoms, or optionally substituted phenyl.

Claims

1. A homo- or copolymer of a 1,3-diene bound to reactive silyl groups, whereby it contains 0.4-12% by weight of bound silicon,

prepared by reacting, at a temperature of 190-300°

C., a 1,3-diene homo- or copolymer, with more than 1% of its aliphatic double bonds in conjugation and having a molecular weight (Mn) of 400-6,000, with a silane of the formula ##STR5## wherein R is an unsaturated aliphatic hydrocarbon radical of 2-20 carbon atoms,

X is halogen, C_1-6 alkoxy, C_1-6 alkoxyalkoxy, C_6-12 aryloxy, C_1-8 alkanoyloxy, C_1-6 ketoximato, C_1-12 hydrocarbylamido,

Y and Z are independently one of the X groups, hydrogen, alkyl of 1-8 carbon atoms, cycloalkyl of 5-12 carbon atoms, or optionally substituted phenyl.

2. A polymer of claim 1, wherein in the preparative reaction, the temperature is 200°

-260°

C.

3. A polymer of claim 1 wherein, the starting diene polymer is a polybutadiene of a molecular weight (Mn) of 600-2000.

4. A polymer of claim 1 or 3, wherein the starting diene polymer has a conjugated double bond content of 1-70% and was pretreated by isomerization of its double bond content.

5. A polymer of claim 1, wherein X is halo or C_1-4 alkoxy.

6. A process for preparing a homo- or copolymer of a 1,3-diene carrying reactive silyl groups of claim 1 consisting essentially of reacting at a temperature of 190°

-300°

C., a 1,3-diene homo- or copolymer having a molecular weight (Mn) of 400-6,000 and containing more than 1% of its aliphatic double bond in conjugation, with a silane of the formula ##STR6## wherein R, X, Y and Z are defined as in claim 1.

7. A process of claim 6, wherein the reaction is conducted at a temperature of 200°

-260°

C.

8. A process of claim 6, wherein the reaction is conducted in the presence of a stabilizer which suppresses the radical polymerization of the unsaturated silane.

9. A composition comprising a polymer, a mineral filler and an effective amount of an adhesion promoter, wherein the adhesion promoter is a silyl-containing polymer of claim 1.

10. A composition of claim 9, wherein the polymer is a natural or synthetic elastomer.