Two-component structural adhesive which is impact resistant at room temperature

Patent metadata

Field	Value
Publication number	US-9296931-B2
Application number	US-201213601280-A
Country	US
Kind code	B2
Filing date	Aug 31, 2012
Priority date	Mar 2, 2010
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

The disclosure relates to the field of two-component epoxy resin compositions and to the use thereof as a repair adhesive, in particular in vehicle manufacturing. The two-component epoxy resin compositions according to the disclosure contain a curing component K2, which comprises between 1 and 10 wt. % of an amino group-terminated polyamide B, together with an epoxy resin component K1. The compositions show that the impact resistance is highly increased while an acceptable sheer strength is simultaneously retained.

First claim

What is claimed is:

1. A two-component epoxy resin composition comprising
one epoxy resin component K1 comprising at least one epoxy resin A that contains on average more than one epoxy group per molecule;
and
one hardener component K2 comprising between 1 and 10% by weight, based on the total weight of the hardener component, of an amino group-terminated polyamide B;
wherein at least one of the components K1 and K2 further comprises at least one impact strength modifier C,
wherein the composition comprises as the impact strength modifier C an amino group terminated impact strength modifier C1 prepared by reacting a polyurethane prepolymer having isocyanate groups, a primary diamine and optionally at least one Michael acceptor, wherein the polyurethane prepolymer having isocyanate groups is prepared from at least one polyisocyanate and at least one polyester or polyether polyol having at least two hydroxyl groups,
and is a component of the hardener component K2, in an amount of from 1 to 30% by weight, based on the weight of the hardener component K2.

2. The two-component epoxy resin composition according to claim 1 , wherein the amino group terminated impact strength modifier C1 has the formula (II)

wherein Y 1 is a linear or branched polyurethane prepolymer terminated with m+m′ isocyanate groups, after removal of all terminal isocyanate groups;
Y 2 is a divalent group of a polyoxyalkylene having C 2 -C 6 alkylene groups, a polybutadiene, a butadiene/acrylonitrile copolymer or a synthetic rubber;
Y 3 independently of one another is H or an alkyl group having from 1 to 10 carbon atoms or a moiety of the formula (III),

wherein
R 4 is a hydrogen atom or a moiety selected from the group consisting of R 7 , —COOR 7 , and —CN,
and R 5 is a moiety selected from the group consisting of COOR 7 , CONH 2 , CONHR 7 , CONR 7 2 , CN, NO 2 , PO(OR 7 ) 2 , SO 2 R 7 , and SO 2 OR 7 , and
R 6 is a hydrogen atom or a moiety selected from the group consisting of —R 7 , —COOR 7 , —CH 2 COOR 7 , and —CN,
wherein R 7 is a univalent hydrocarbon moiety having from 1 to 20 carbon atoms;
Y 4 is an alkylene group having from 1 to 6 carbon atoms or provided that p and p′=0 is nothing; and
Y 5 is a divalent moiety of the formula (IV) or (IV′);

wherein
R 4′ is a hydrogen atom or a moiety selected from the group consisting of R 7 , —COOR 7 , and —CN,
and R 5′ is a moiety selected from the group consisting of COOR 7 , CONH 2 , CONHR 7 , CONR 7 2 , CN, NO 2 , PO(OR 7 ) 2 , SO 2 R 7 , and SO 2 OR 7 , and
R 6′ is a hydrogen atom or a moiety selected from the group consisting of —R 7 , —COOR 7 , —CH 2 COOR 7 , and —CN,
wherein R 7 is a univalent hydrocarbon moiety having from 1 to 20 carbon atoms;
p and p′ are each 0 or 1;
q and q′ are each 0 or 1;
m and m′ are each values of from 0 to 7, provided that m+m′ are a value of from 1 to 8.

3. The two-component epoxy resin composition according to claim 2 , wherein m and m′ are each values of 0 or 1 or 2.

4. The two-component epoxy resin composition according to claim 1 , wherein the composition further comprises as the impact strength modifier C a liquid rubber C2 which comprises an epoxy-terminated polymer,
and the liquid rubber C2 is a component of the epoxy resin component K1, in an amount of from 1 to 45% by weight, based on the weight of the epoxy resin component K1.

5. The two-component epoxy resin composition according to claim 4 , wherein the liquid rubber C2 comprises an epoxy-terminated acrylonitrile/butadiene copolymer.

6. The two-component epoxy resin composition according to claim 1 , wherein the composition further comprises as the impact strength modifier C a polymer C3 of the formula (XI)

wherein R 1 is a linear or branched polyurethane prepolymer terminated with n+n′ isocyanate groups, after removal of all terminal isocyanate groups;
R 2 and R 3 each independently of one another are a substituent selected from the group consisting of

wherein R 14 is a moiety of an aliphatic, cycloaliphatic, aromatic, or araliphatic epoxy containing a primary or secondary hydroxyl group, after removal of the hydroxy and epoxy groups;
pp represents a value of 1, 2 or 3;
R 15 , R 16 , R 17 , and R 18 each independently of one another are an alkyl or cycloalkyl or an aralkyl or arylalkyl group;
or
R 15 together with R 16 , or R 17 together with R 18 forms a part of an optionally substituted 4- to 7-membered ring;
R 19 , R 19′ , and R 20 each independently of one another are an alkyl or aralkyl or arylalkyl group or an alkyloxy or aryloxy or aralkyloxy group;
R 21 is an alkyl group;
R 23 and R 24 each independently of one another are an alkylene group having from 2 to 5 C atoms which optionally contains double bonds or is substituted, or are a phenylene group or a hydrogenated phenylene group;
R 25 , R 26 , and R 27 each independently of one another are H or an alkyl group or an aryl group or an aralkyl group;
R 28 is an aralkyl group or a mono- or polynuclear substituted or unsubstituted aromatic group which optionally has aromatic hydroxyl groups;
and n and n′ independently of one another are each values of from 0 to 7, provided that n+n′ is a value of from 1 to 8.

7. The two-component epoxy resin composition according to claim 1 , wherein the composition further comprises as the impact strength modifier C an amino group terminated acrylonitrile/butadiene copolymer C4 and the amino group terminated acrylonitrile/butadiene copolymer C4 is a component of the hardener component K2, in an amount of from 10 to 40% by weight, based on the weight of the hardener component K2.

8. The two-component epoxy resin composition according to claim 1 , wherein the composition comprises as the impact strength modifier C a combination of the amino group terminated impact strength modifier C1 with a liquid rubber C2 and/or a polymer C3 having the formula (XI) and/or an amino group terminated acrylonitrile/butadiene copolymer C4

wherein R 1 is a linear or branched polyurethane prepolymer terminated with n+n′ isocyanate groups, after removal of all terminal isocyanate groups;
R 2 and R 3 each independently of one another are a substituent selected from the group consisting of

wherein R 14 is in turn a moiety of an aliphatic, cycloaliphatic, aromatic, or araliphatic epoxy containing a primary or secondary hydroxyl group, after removal of the hydroxy and epoxy groups;
pp represents a value of 1, 2 or 3;
R 15 , R 16 , R 17 , and R 18 each independently of one another are an alkyl or cycloalkyl or an aralkyl or arylalkyl group;
or
R 15 together with R 16 , or R 17 together with R 18 forms a part of an optionally substituted 4- to 7-membered ring;
R 19 , R 19′ , and

Assignees

• Frick Karsten
• FINTER JüRGEN
• Kramer Andreas
• Gerber Ulrich
• Sika Technology Ag

Inventors

• Frick Karsten
• FINTER JüRGEN
• Kramer Andreas
• Gerber Ulrich

Classifications

• C08L2666/04

  Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C09J163/00 Primary

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08L19/006

  Rubber characterised by functional groups, e.g. telechelic diene polymers · CPC title

• C08L75/00

  Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers · CPC title