Adhesives and sealants

Details Adhesives and sealants Adhesives and sealants

2001-01-03

2004-03-09

Harlan, Robert Deshon (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S305000, C526S306000, C526S310000, C526S312000

Reexamination Certificate

active

06703467

ABSTRACT:

The present invention relates to adhesive and/or sealant compositions, to novel compounds which may be used in the compositions and to methods of their production.
The applicants have found that certain unsaturated monomeric compounds can, under particular conditions, polymerise so as to form effective adhesion between surfaces.
According to the present invention there is provided an adhesive or sealant composition comprising a compound of formula (I)
where
R
1
is CH and R
6
is a bond, or R
1
and R
6
together form an electron withdrawing group;
R
2
and R
3
are independently selected from (CR
8′
R
8
)
n
, or a group CR
9
R
10
, —(CR
8′
R
6
CR
9
R
10
)— or —(CR
9
R
10
CR
8′
R
8
)— where n is 0, 1 or 2, R
8′
and R
8
are independently selected from hydrogen or alkyl, and either one of R
9
or R
10
is hydrogen and the other is an electron withdrawing group, or R
9
and R
10
together form an electron withdrawing group,
R
4
and R
5
are independently selected from CH or CR
11
where R
11
is an electron withdrawing group, and
R
7
is hydrogen, an optionally substituted hydrocarbyl group, a perhaloalkyl group or a functional group;
the dotted lines indicate the presence or absence of a bond,
and X
1
is a group CX
2
X
3
where the dotted line bond to which it is attached is absent and a group CX
2
where the dotted line bond to which it is attached is present, Y
1
is a group CY
2
Y
3
where the dotted line bond to which it is attached is absent and a group CY
2
where the dotted line bond to which it is attached is present, and X
2
, X
3
, Y
2
and Y
3
are independently selected from hydrogen and fluorine;
provided that at least one of (a) R
1
and R
6
or (b) R
2
and R
3
or (c) R
4
and R
5
includes an electron withdrawing group;
and where necessary, a polymerization initiator.
As used herein, the expression “adhesive or sealant composition” includes either an adhesive composition and/or a sealant composition. An “adhesive composition” is a glue—like material which, when interposed between surfaces, will hold the surfaces together. The resulting bond between the surface is sufficiently strong and will remain in place for a period of time which is appropriate for the desired application. Surfaces include glass, metal, wood, paper, card, ceramics, plastics, laminates, stone, construction materials as well as biological material such as tissue. The expression “sealant composition” refers to compositions which may be applied to one or more surfaces to form a protective barrier thereon, for example to prevent ingress or egress of solid, liquid or gaseous material or alternatively to allow selective permeability through the barrier to gas and/or liquid. In particular, it may provide a seal between surfaces.
Preferably, where R
2
and R
3
are both (CR
7
R
8
)
n
, at least one n is 1 or 2. Suitably in formula (I), n is 1 or 2.
As used herein, the term “alkyl” refers to straight or branched chain alkyl groups, suitably containing up to 20 and preferably up to 6 carbon atoms. The term “alkenyl” and “alkynyl” refer to unsaturated straight or branched chains which include for example from 2-20 carbon atoms, for example from 2 to 6 carbon atoms. Chains may include one or more double or triple bonds respectively. In addition, the term “aryl” refers to aromatic groups such as phenyl or naphthyl.
The term “hydrocarbyl” refers to any structure comprising carbon and hydrogen atoms. For example, these may be alkyl, alkenyl, alkynyl, aryl such as phenyl or napthyl, aralkyl, cycloalkyl, cycloalkenyl or cycloalkynyl. Suitably they will contain up to 20 and preferably up to 10 carbon atoms. The term “heterocyclyl” includes aromatic or non-aromatic rings, for example containing from 4 to 20, suitably from 5 to 10 ring atoms, at least one of which is a heteroatom such as oxygen, sulphur or nitrogen. Examples of such groups include furyl, thienyl, pyrrolyl, pyrrolidinyl, imidazolyl, triazolyl, thiazolyl, tetrazolyl, oxazolyl, isoxazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, iosquinolinyl, quinoxalinyl, benzthiazolyl, benzoxazolyl, benzothienyl or benzofuryl.
The term “functional group” refers to reactive groups such as halo, cyano, nitro, oxo, C(O)
n
R
a
, OR
a
, S(O)
t
R
a
, NR
b
R
c
, OC(O)NR
b
R
c
, C(O)NR
b
R
c
, OC(O)NR
b
R
c
, —NR
7
C(O)
n
R
6
, —NR
a
CONR
b
R
c
, NR
a
CSNR
b
R
c
, —C═NOR
a
, —N═CR
b
R
c
, S(O)
t
NR
b
R
c
, C(S)
n
R
a
, C(S)OR
a
, C(S)NR
b
R
c
or —NR
b
S(O)
t
R
a
where R
a
, R
b
and R
c
are independently selected from hydrogen or optionally substituted hydrocarbyl, or R
b
and R
c
together form an optionally substituted ring which optionally contains further heteroatoms such as S(O)
t
, oxygen and nitrogen, n is an integer of 1 or 2, t is 0 or an integer of 1-3. In particular the functional groups are groups such as halo, cyano, nitro, oxo, C(O)
n
R
a
, OR
a
, S(O)
t
R
a
, NR
b
R
c
, OC(O)NR
b
R
c
, C(O)NR
b
R
c
, OC(O)NR
b
R
c
, —NR
7
C(O)
n
R
6
, —NR
a
CONR
b
R
c
, —C═NOR
a
, —N═CR
b
R
c
, S(O)
t
NR
b
R
c
, or —NR
b
S(O)
t
R
a
where R
a
, R
b
and R
c
, n and t are as defined above.
The term “heteroatom” as used herein refers to non-carbon atoms such as oxygen, nitrogen or sulphur atoms. Where the nitrogen atoms are present, they will generally be present as part of an amino residue so that they will be substituted for example by hydrogen or alkyl.
A particular functional group for R
7
is an amide. The term “amide” is generally understood to refer to a group of formula C(O)NR
a
R
b
where R
a
and R
b
are hydrogen or an optionally substituted hydrocarbyl group.
Suitable *polymerization initiators for inclusion in the compositions of the invention will depend upon the nature of the compound of formula (I) and the intended use to which the adhesive or sealant is to be put. For instance, where an adhesive is intended for use in circumstances where it is or may be exposed to ultraviolet radiation, such as in the adhesion of transparent materials such as glass, the compound of formula (I) is suitably a compound which will polymerise or cure under the influence of u.v. radiation. In such cases, suitable polymerisations initiators will include 2,2′-azobisisobutyronitrile (AIBN) aromatic ketones such as benzophenones in particular acetophenone; chlorinated acetophenones such as di- or tri-chloroacetophenone; dialkoxyacetophenones such as dimethoxyacetophenones (sold under the Trade name “Irgacure 651”); dialkylhydroxyacetophenones such as dimethylhydroxyacetophenone (sold under the Trade name “Darocure 1173”); substituted dialkylhydroxyacetophenone alkyl ethers such compounds of formula
where R
y
is alkyl and in particular 2,2-dimethylethyl, R
x
is hydroxy or halogen such as chloro, and R
P
and R
q
are independently selected from alkyl or halogen such as chloro (examples of which are sold under the Trade names “Darocure 1116” and “Trigonal P1”); 1-benzoylcyclohexanol-2 (sold under the Trade name “Irgacure 184”); benzoin or derivatives such as benzoin acetate, benzoin alkyl ethers in particular benzoin butyl ether, dialkoxybenzoins such as dimethoxybenzoin or deoxybenzoin; dibenzyl ketone; acyloxime esters such as methyl or ethyl esters of acyloxime (sold under the trade name “Quantaqure PDO”); acylphosphine oxides, acylphosphonates such as dialkylacylphosphonate, ketosulphides for example of formula
where R
z
is alkyl and Ar is an aryl group; dibenzoyl disulphides such as 4,4′-dialkylbenzoyldisulphide; diphenyldithiocarbonate; benzophenone; 4,4′-bis(N,N-dialkylamino)benzophenone; fluorenone; thioxanthone; benzil; or a compound of formula
where Ar is an aryl group such as phenyl and R
z
is alkyl such as methyl (sold under the trade name “Speedcure BMDS”).
Such compositions may be used in applications where it is possible to deliver uv radiation, for example by means of a fibre optic conductor, so as to cause the adhesive or sealant to cure.
Other conventional polymerization initiators including free radical initiators, as are known in the art can be emplo

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