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US 2003/0225231 A1Published application
Polymers
AssigneeQinetiq Limited
InventorAlam W Hall
Life of this patent
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AssigneeQinetiq Limited
InventorAlam W Hall
Estimating the term…
A copolymer containing repeat units formed from the monomers (I) and (II), wherein each R1, if present, is independently hydrogen or hydrocarbyl; r is 0, 1 or 2; s is either 2 or 3; R2-R4 are each independently hydrogen or hydrocarbyl; R5 and R6 are each independently hydrogen, halo or hydrocarbyl; Pd− is the anion formed by loss of a proton from a proton donating group Pd-H; Z is either a bond or hydrocarbyl; R7 and R8 are each independently hydrogen, halo or hydrocarbyl; and either (a) A is an electron accepting group and W is either hydrogen or hydrocarbyl, (b) W is an electron accepting group and A is either a bond or hydrocarbyl or (c) both A and W are electron accepting groups. The invention also provides a method for preparing the copolymer by polymerising a mixture of (I) and (II) or their non-ionised precursors, preferably by exposure to ultraviolet radiation. The invention also relates to the uses of the copolymer in adhesive, coating, sealant and stereolithographic compositions.
1 A copolymer containing repeat units formed from both the monomer (I):
2 A copolymer according to claim 1, wherein in the monomer (II) the proton donating group Pd-H is OH.
3 A copolymer according to claim 1 or claim 2, wherein in the monomer (II) an electron accepting group A or W is, or contains, C═O, O═S═O or P═O.
4 A copolymer according to any one of the preceding claims, wherein in the monomer (II) Z is a bond.
5 A copolymer according to any one of the preceding claims, wherein in the monomer (II) R7 and R8 are both hydrogen.
6 A copolymer according to any one of the preceding claims, wherein the monomer (II) is an optionally substituted acrylate, methacrylate, itaconate, vinyl sulphonate or vinyl phosphonate.
7 A copolymer according to any one of the preceding claims, wherein the monomer (II) has the general formula (IX):
8 A copolymer according to claim 7, wherein v is 2.
9 A copolymer according to claim 8, wherein B1 is H2C—C(O)—O—(CH2)w—O—C(O)—CH2, where w is an integer from 1 to 20, or H2C—C(O)—O—CH2—(CF2)y—CH2—O—C(O)—CH2, where y is an integer from 1 to 10.
10 A copolymer according to any one of the preceding claims, wherein in the monomer (I) r is 1.
11 A copolymer according to any one of the preceding claims, wherein in the monomer (I), R2-R6 are all hydrogen.
12 A copolymer according to any one of the preceding claims, wherein in the monomer (I), R1 is either hydrogen or hydroxyalkyl.
13 A copolymer according to any one of the preceding claims, wherein in the monomer (I), s is 2.
14 A copolymer according to claim 13, wherein in the monomer (I), R1 is hydrogen.
15 A copolymer according to claim 13, wherein in the monomer (I), R1 is not hydrogen.
16 A copolymer according to any one of claims 1 to 12, wherein in the monomer (I), s is 3.
17 A copolymer according to any one of claims 1 to 15, wherein the monomer (I) has the formula (X):
18 A copolymer according to claim 17, wherein a is 2.
19 A copolymer according to claim 18, wherein B2 is —(CH2)b where b is an integer from 1 to 20.
20 A copolymer according to any one of the preceding claims, containing stoichiometrically equivalent amounts of the monomers (I) and (II).
21 A copolymer according to any one of claims 1 to 19, containing a stoichiometric excess of the monomer (II).
22 A copolymer according to any one of the preceding claims, containing at least 40% w/w of the monomer (I).
23 A copolymer according to any one of the preceding claims, containing at least 40% w/w of the monomer (II).
24 A copolymer according to any one of the preceding claims, which is water impermeable or substantially so.
25 A copolymer substantially as herein described.
26 A method for preparing a copolymer according to any one of the preceding claims, the method comprising polymerising a mixture of the monomers (I) and (II).
27 A method according to claim 26, wherein the monomer mixture is prepared by mixing together the precursor allylamine (III):
28 A method according to claim 26, wherein the monomer mixture is prepared by mixing together the already ionised monomers (I) and (II), each stabilised by a suitable counterion.
29 A method according to any one of claims 26 to 28, wherein the monomer mixture is polymerised by exposure to ultraviolet radiation.
30 A polymerisable mixture of the monomers (I) and (II) as defined in any one of claims 1 to 25, and/or of their precursors (III) and (IV) as defined in claim 27.
31 A monomer mixture according to claim 30, which is polymerisable on exposure to ultraviolet radiation.
32 A monomer mixture according to claim 30 or claim 31, containing a stoichiometric excess of the monomer (II)/(IV).
33 A monomer mixture according to any one of claims 30 to 32, which comprises either:
34 A monomer mixture substantially as herein described.
35 Use of a monomer mixture according to any one of claims 30 to 34, in preparing a copolymer according to any one of claims 1 to 25.
36 Use of a monomer mixture according to any one of claims 30 to 34, in the preparation of a coating, adhesive or sealant composition.
37 Use of a monomer mixture according to any one of claims 30 to 34, in a method for applying a coating, adhesive or sealant to a substrate, wherein the coating, adhesive or sealant contains a copolymer according to any one of claims 1 to 25.
38 Use of a monomer (II) as defined in any one of claims 1 to 25, and/or of a monomer precursor (IV) as defined in claim 27, in the preparation of a copolymer according to any one of claims 1 to 25.
39 Use of a monomer (II) as defined in any one of claims 1 to 25, and/or of a monomer precursor (IV) as defined in claim 27, in the preparation of a coating, adhesive or sealant composition containing a copolymer according to any one of claims 1 to 25.
40 Use of a monomer (II) as defined in any one of claims 1 to 25, and/or of a monomer precursor (IV) as defined in claim 27, in a method for applying a coating, adhesive or sealant to a substrate, wherein the coating, adhesive or sealant contains a copolymer according to any one of claims 1 to 25.
41 Use of a monomer (I) as defined in any one of claims 1 to 25, and/or of a monomer precursor (III) as defined in claim 27, in the preparation of a copolymer according to any one of claims 1 to 25.
42 Use of a monomer (I) as defined in any one of claims 1 to 25, and/or of a monomer precursor (III) as defined in claim 27, in the preparation of a coating, adhesive or sealant composition containing a copolymer according to any one of claims 1 to 25.
43 Use of a monomer (I) as defined in any one of claims 1 to 25, and/or of a monomer precursor (III) as defined in claim 27, in a method for applying a coating, adhesive or sealant to a substrate, wherein the coating, adhesive or sealant contains a copolymer according to any one of claims 1 to 25.
44 A coating, adhesive or sealant composition containing a copolymer according to any one of claims 1 to 25 and/or a monomer mixture according to any one of claims 30 to 34.
45 A coating, adhesive or sealant composition according to claim 44, which contains greater than 60% w/w of the copolymer or of the monomer mixture.
46 A coating, adhesive or sealant composition substantially as herein described.
47 A kit for preparing an adhesive, coating or sealant composition, the kit comprising a quantity of a monomer (I) as defined in any one of claims 1 to 25 and/or of a monomer precursor (III) as defined in claim 27;
48 A kit according to claim 47, which comprises a photoinitiator capable of promoting ultraviolet curing of a mixture of (I)/(III) and (II)/(IV).
49 A kit according to claim 47 or claim 48, containing a stoichiometric excess of the monomer (II)/(IV).
50 A kit according to any one of claims 47 to 49, which is for preparing an adhesive composition.
51 A method for preparing a coating, adhesive or sealant composition, the method comprising mixing together (a) a monomer (I) as defined in any as defined in any one of claims 1 to 25 and/or a monomer precursor (III) as defined in claim 27 and (b) a monomer (II) as defined in any one of claims 1 to 25 and/or a monomer precursor (IV) as defined in claim 27, and polymerising the mixture.
52 A method for applying a coating, adhesive or sealant to a substrate, the method comprising applying to the substrate a monomer mixture according to any one of claims 30 to 34, optionally with a polymerisation initiator, and inducing polymerisation of the mixture on the substrate.
53 A method of adhering surfaces to one another and/or of applying a seal between them, the method comprising applying to a first surface a monomer mixture according to any one of claims 30 to 34, contacting the treated first surface with a second surface to which it is to be adhered and/or sealed, and inducing polymerisation of the monomer mixture.
54 A method according to claim 53, which comprises applying to the first surface a monomer (I) as defined in any one of claims 1 to 25, and/or a monomer precursor (III) as defined in claim 27;
55 A method according to any one of claims 51 to 54, wherein polymerisation is induced by ultraviolet radiation.
56 A method according to any one of claims 26 to 29 or 51 to 55, which is substantially as herein described.
57 A product having deposited thereon a coating, adhesive or sealant comprising a copolymer according to any one of claims 1 to 25, and/or a monomer mixture according to any one of claims 30 to 34, and/or a coating, adhesive or sealant composition according to any one of claims 44 to 46.
58 A product according to claim 57, which is substantially as herein described.
59 Use of a copolymer according to any one of claims 1 to 25, and/or of a monomer mixture according to any one of claims 30 to 34, in a stereolithographic process.
60 A stereolithographic composition containing a copolymer according to any one of claims 1 to 25, and/or a monomer mixture according to any one of claims 30 to 34.
61 A stereolithographic process which involves the use of a copolymer according to any one of claims 1 to 25, and/or of a monomer mixture according to any one of claims 30 to 34, and/or of a stereolithographic composition according to claim 60, to produce a three dimensional object.
62 A three dimensional object produced using a stereolithographic process according to claim 61.
63 A copolymer containing repeat units formed from both the monomer (I) as defined in any one of claims 1 to 25, and a proton donating monomer containing (a) a proton donating group, (b) a carbon-carbon double bond and (c) an electron accepting group, wherein there are no more than four chain atoms between (a) and (b) and between (b) and (c).