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Composition of butadiene/polar comonomer copolymer, aromatic reactive end group-containing prepolymer and epoxy resin

Assignee: Novartis Corp
•
Filing: 1989-07-25
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Granted: 1991-12-17
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Expires: 2009-07-25
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Abstract

Abstract The invention relates to compositions containing A) a liquid copolymer based on butadiene and at least one polar, ethylenically unsaturated comonomer, and B) a polyether prepolymer capped with hydroxyarylcarboxylic or hydroxyaralkylcarboxylic acids, or a capped polyester, polythioester or polyamide containing polyether segments. The phenolic hydroxyl group in component B) can also be etherified with epichlorohydrin and this product can be converted to an episulfide, if desired, or the phenolic hydroxyl group can be reacted with cyanogen halide to form a cyanate group. The stock compositions can be used in combination with epoxy resins to manufacture structural adhesives or sealing compounds.

Inventors

  • 👤 Rolf Mulhaupt
  • 👤 Werner Rufenacht

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 11:21
CPC Classifications
C; C08; C08L; C08L9/00; C08L101/00; C08L63/00

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 236 words
A composition comprising A) a liquid copolymer based on butadiene and at least one polar, ethylenically unsaturated comonomer; B) a prepolymer of formula I: ##STR13## wherein m is 1 or 2, n is 2 to 6, X is --O--, --S-- or --NR 3 --, Y is a radical selected from the group consisting of --OH, --NHR 3 , --OH reacted with a cyanogen halide to introduce --OCN, --OH reacted with an epichlorohydrin to introduce ##STR14## and --OH reacted with an epichlorohydrin to introduce an epoxide which is reacted with potassium thiocyanate or thiourea to introduce ##STR15## R 1 is a radical of a polyether, prepolymer with hydroxyl mercapto or amino end groups or of a segmented polyester, polythioester or polyamide prepolymer with hydroxyl, mercapto or amino end groups, containing at least +mol%, based on said segmented prepolymer, of polyether segments after removal of the functional end groups, R 2 is a carbocyclic aromatic or araliphatic radical of valency m+1 with groups Y bonded directly to the aromatic ring, R 3 is hydrogen, C 1 -C 6 -alkyl or phenyl and R 4 is methyl or hydrogen; C) an epoxy resin with at least two 1,2-epoxy groups per molecule; and D) an effective amount of a hardener based on an aromatic polyamine with at least two primary or secondary amino groups or an aromatic polyamine with at least two primary and secondary amino groups or an amidine.
Claim 2
Dependent Claim 236 words
A composition comprising A) a liquid copolymer based on butadiene and at least one polar, ethylenically unsaturated comonomer; B) a prepolymer of formula I: ##STR13## wherein m is 1 or 2, n is 2 to 6, X is --O--, --S-- or --NR 3 --, Y is a radical selected from the group consisting of --OH, --NHR 3 , --OH reacted with a cyanogen halide to introduce --OCN, --OH reacted with an epichlorohydrin to introduce ##STR14## and --OH reacted with an epichlorohydrin to introduce an epoxide which is reacted with potassium thiocyanate or thiourea to introduce ##STR15## R 1 is a radical of a polyether, prepolymer with hydroxyl mercapto or amino end groups or of a segmented polyester, polythioester or polyamide prepolymer with hydroxyl, mercapto or amino end groups, containing at least +mol%, based on said segmented prepolymer, of polyether segments after removal of the functional end groups, R 2 is a carbocyclic aromatic or araliphatic radical of valency m+1 with groups Y bonded directly to the aromatic ring, R 3 is hydrogen, C 1 -C 6 -alkyl or phenyl and R 4 is methyl or hydrogen; C) an epoxy resin with at least two 1,2-epoxy groups per molecule; and D) an effective amount of a hardener based on an aromatic polyamine with at least two primary or secondary amino groups or an aromatic polyamine with at least two primary and secondary amino groups or an amidine.
Claim 3
Dependent Claim 10 words
A composition according to claim 1 further containing an accelerator.
Claim 4
Dependent Claim 79 words
A composition according to claim 1 selected from the group consisting of a composition containing components A), B), C) and said hardener; a composition containing an adduct of component A) and an epoxy resin, component B), component C) and said hardener, a composition containing component A), an adduct of compound B) and an epoxy resin component C) and said hardener; and a composition containing an adduct of component A), an adduct of component B), component C) and said hardener.
Claim 5
Dependent Claim 14 words
A composition according to claim 1, wherein component A) is a liquid butadiene/acrylonitrile copolymer.
Claim 6
Dependent Claim 28 words
A composition according to claim 1, wherein component A) is an adduct of a butadiene/acrylonitrile copolymer containing functional groups which react with epoxy resins, and an epoxy resin.
Claim 7
Dependent Claim 28 words
A composition according to claim 1, in which R 1 is a polyalkylene glycol radical with hydroxyl, mercapto or amino end groups, after removal of the functional groups.
Claim 8
Dependent Claim 21 words
A composition according to claim 6, in which the polyalkylene glycol radical is a polypropylene glycol or a polybutylene glycol radical.
Claim 9
Dependent Claim 17 words
A composition according to claim 1, in which n is 2 or 3 and m is 1.
Claim 10
Dependent Claim 14 words
A composition according to claim 1, in which X is --O--, --S-- or --NH--.
Claim 11
Dependent Claim 15 words
A composition according to claim 1, in which Y is --NH 2 ----OH, --OCN, ##STR16##
Claim 12
Dependent Claim 13 words
A composition according to claim 10, in which Y is --OH, --OCN, ##STR17##
Claim 13
Dependent Claim 11 words
A composition according to claim 1, in which Y is --OH.
Claim 14
Dependent Claim 83 words
A composition according to claim 1, in which R 2 is a radical of formula IVa, IVb or ##STR18## wherein R 7 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, halogen or phenyl, p is an integer from 0 to 3, q is 1,2 or 3 and Q is a direct bond, --C q H 2q --, --O--, --S--, --SO 2 --, --CO -- or --C(CF 3 ) 2 .
Claim 15
Dependent Claim 29 words
A composition according to claim 13 in which p is 0 or 1, q is 1 or 2 and Q is --CH 2 --or --C(CH 3 ) 2 --.
Claim 16
Dependent Claim 51 words
A composition according to claim 1 in which m is 1, n is 2 or 3, R 1 is a radical of a polyalkylene glycol with hydroxyl, mercapto or amino end groups, after removal of the functional groups, and R 2 is a radial formula IVd, IVe, IVf or IVg; ##STR19##
Claim 17
Dependent Claim 16 words
A compound of formula I according to claim 1 in which Y is --OCN or ##STR20##
Claim 18
Dependent Claim 19 words
A composition according to claim 2 in which the hardener is dicyandiamide and the accelerator is a urea-based accelerator.
Claim 19
Dependent Claim 17 words
A cured product obtained by heating a composition according to claim 1 in order to cure it.

References Cited (Backward Citations)

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US3943096A Cited
DE2910020A1 Cited
US4602071A Cited
US4609691A Cited
US4820789A Cited
EP0247476A1 Cited
EP0247483A2 Cited
US4680076A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-12-16 1995-06-17 1995-12-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-12-16 1999-06-17 1999-12-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-12-16 2003-06-17 2003-12-17 $7700.00 Window Closed / Lapsed

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