GB2220204A - New vinyl esters and their use in the building industry - Google Patents

New vinyl esters and their use in the building industry Download PDF

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Publication number
GB2220204A
GB2220204A GB8914922A GB8914922A GB2220204A GB 2220204 A GB2220204 A GB 2220204A GB 8914922 A GB8914922 A GB 8914922A GB 8914922 A GB8914922 A GB 8914922A GB 2220204 A GB2220204 A GB 2220204A
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compound
branched
linear
coor
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GB8914922D0 (en
GB2220204B (en
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Jose Canela
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Sandoz AG
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Sandoz AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/02—Macromolecular compounds
    • C04B26/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/02—Macromolecular compounds
    • C04B26/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B26/06—Acrylates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Ceramic Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Working Measures On Existing Buildindgs (AREA)
  • Aftertreatments Of Artificial And Natural Stones (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerization Catalysts (AREA)

Description

n2nn.
/_ 'L,-i 2 (1 4 u Case 154-0136 NEW VINYL ESTERS AND THEIR USE IN THE BUILDING INDUSTRY According to the invention there is provided a composition comprising a) one or more compounds of formula I CH = C - CO (OR) - OR 2 1 1 n 2 R in which R is hydrogen or methyl, R, is linear or branched C2-8 alkylene n is an integer from 1 to 10 inclusive R2 is a group of formula a) to i) CO (a) COOR, CO- CCH 2 " CO -OR 13 (e) CH2 OR 11 11 (h) 12 CH-C _ H 3 or (I) :::: r CO - (b) (1 coo R 3 CH 2 H- 11 -CH 2 c C-O-CH 3 CO - - (d) COOR (c) 3 OR 3 CH3 CH3 -CH 2 ----CH 2_ M (g) CH 2CH3 1 4H20 __CH2 -C where R3 is a linear or branched Cl-22 alkyl group, linear or branched G2-22 alkenyl, unsaturated or saturated C5-6 cycloalkyl (e.g.
(f) (i) Case 154-0136 cyclohexyl or cyclopentyl), phenyl, naphthyl, -H3 CH -A - or A - R, 5 where A is C1-6 alkylene or C2-6 alkenylene; R,, is hydrogen or acetyl; and R15 is C1-6 alkyl; (hereinafter ref erred to as component a) and b) optionally one or more vinyl compounds that are other than of formula I (hereinafter referred to as component b); and c) 0.1 to 10 % (based on the weight of components a) and b) present) of two or more polymerisation catalysts (hereinafter referred to as component c), all percentages being by weight of the composition.
Preferably 20-100, more preferably 50-95 % of component a) and 0 to 80, more preferably 5-50 X of component b) based on the total weight of monomers are present in a composition according to the invention.
Compositions according to the invention preferably contain d) 40-95 % based on the total weight of the composition of inorganic aggregate (hereinafter referred to as component d).
The addition of the polymerisation catalysts (component c), for example, organic hydroperoxide and aromatic amine accelerator and optionally a polyvalent metal salt complex can be made to the monomer mixture prior to application. The proportion of metal salt or complex added to the composition before application may be from 0.0005 weight percent up to about 2 weight percent, and the amount of hydroperoxide Case.154-0136 1 may be in the range of 0.1 to 5 weight percent, based on the total weight of the monomers. Similarly, the addition of an organic peroxide, with an aromatic amine accelerator; and optionally with a polyvalent metal salt or complex, can be made to the mixture prior to application. The proportion of the organic peroxide to the composition may be in the range of 0.1 to 5 weight percent and the aromatic amine accelerator is used in an effective amount, usually in the range of about 0.1 to 5 weight percent.
The polymerisation catalyst components, such as polyvalent metal. salt or complex and hydroperoxide, and amine accelerator or the aromatic amine accelerator and peroxide, may be packed and shipped separately to the site of operations where the respective components may be combined and where the composition of the present invention is to be applied, as by pouring or spraying to impregnate or seal a concrete floor or base or pavement. Alternatively, the aromatic amine accelerator and binder monomer system, and the organic peroxide (optionally together with aggregate) respectively, may be combined in packages for storing and shipping prior to combining them to provide the composition of the invention shortly before applying the composition.
The polyvalent metal salt or complex used in the invention may be any polyvalent metal-containing salt that catalyzes the oxidative curing of drying oils and, when added to oil-based varnishes'and paints, hastens the drying or curing thereof. These metal salts or complexes are also known, in the art, as 11siccatives" or "driers". Such substances include the polyvalent metal salts of higher aliphatic having from 8 to 30 carbon atoms or of naphthenic acids that provide solubility in the binder monomer system. Generally, the most useful drier salts for the compositions of the present invention are salts of naphthenic acids or Of CS-30 aliphatic acids. Examples of the polyvalent metal include calcium, copper ", zinc II, manganese 11, manganese 111, lead 'I, cobalt I', iron III, vanadium 11 and zirconium Iv. These salts or complexes accelerate the action of the organic hydroperoxide and promote oxidative curing in the organic peroxide-amine catalyst system. Other examples of the acid component Case 154-0136 or anion of the drier salt are those of resinic acids, 2-ethylhexanoic acid, lauric acid, palmitic acid, myristic acid, stearic acid, oleic acid, linoleic acid, behenic acid, cerotic acid, monotanic acid and abietic acid. A mixture of drier salts may be used.
Preferred drier salts are those of cobalt and manganese, such as cobalt octoate, cobalt naphthenate, cobalt acetylacetoriate and manganese octoate, manganese naphthenate, and manganese acetylacetonate.
Aromatic amines may be used in small amounts with the organic peroxides and generally accelerate the action of the peroxide. For example, aniline, N,N-dimethylaniline, N,N-diethylaniline, toluidine, N,N-dimethyl ptoluidine, N,N-di(hydroxyethyl)toluidine, and p-dimethylaminobenzaldehyde may be added for this purpose in an amount of 0.1 to 2 percent by weight of the binder monomer system.
The organic peroxides and hydroperoxides that may be used include the peroxides and the hydroperoxides derived from hydrocarbons which contain from about 3 to 18 carbon atoms so that they are soluble in the binder monomer system. Suitable organic hydroperoxides include tertiarybuty1hydroperoxide, cumene hydroperoxide, methyl ethyl ketone hydroperoxide and diisopropylbenzene hydroperoxide. Suitable peroxides include benzoyl peroxide, tert-butylperbenzoate, dilaurylperoxide, di-(4tert.butyl-cyclohexyl)-peroxide dicarbonate, 2-,2-bis-(tertbutylperoxy)butane, bis-(l-hydroxy-cyclohexyl)-butane, bis-(l-hydroxy -cyclohexyl)peroxide, and tert-butylperoxy-isopropyl carbonate.
A preferable polymerization catalyst is a mixture of an organic peroxide and an aromatic amine. A more preferable polymerization catalyst is a mixture of benzoyl peroxide or cumene hydroperoxide and N,N-dimethyl ptoluidine. An especially preferred polymerization catalyst is a mixture of p-dimethylaminobenzaldehyde, benzoyl peroxide or cumene hydroperoxide and cobalt naphthenate.
The aggregate material (component d) optionally used herein may be Case 154-0136 any inert inorganic substance that is resistant to such organic and inorganic acids, salts and alkalis as may be encountered in common industrial plants, e.g. hydrochloric acid, sulfuric acid, nitric acid, sulfonic acid, phosphoric acid, acetic acid, formic acid; and sodium, potassium, calcium and magnesium salts, e.g. the chlorides, sulfates and alkali metal and alkaline earth metal hydroxides. Examples of suitable aggregates include sand, silica flour, crushed rocks or stones of quartz, granite, feldspar, gneiss, basalt, porphyry, and small pebbles thereof. The sand that may be used may be of any quality or of any size. Graded sand of medium particle size such as "Ottawa" sand and "Best" sand or a mixture of the two may be used to better advantage. Ottawa sand is a silica sand of the type referred to as "round". Best sand is of the type known as "sharp". In both cases, fines will have been removed. In general, however, the sieve size of the sand may vary over a fairly wide range. In lieu of or in addition to sand, it is possible to use fractured colored glass marbles, ground glass, silica flour, emergy powder, ground slag, and fine gravel.
Further according to the invention there is provided a three package composition, adapted to be used together, a first package comprising components a) and b) a second package comprising component c) and, a third package comprising component d).
The second and third packages may also be combined together or the first and third packages may be combined together.
Preferably R, is R,' where R,' is -CH2-CH2-; C2Hs CH2-CH-; -CH2-CH- or (CH2)6- CH3 -6 Preferably n is 1.
Case 154-0136 Preferably R2 is R2t where R21 is a group of formula a' or bl CO - C) COOR 3 ' W) where R3t is as defined below.
CO - I () COOR 3 1 Preferably R3 is R3r where R30 is a linear or branched Cl-12 alkyl or C2- 12 alkenyl.
Preferably in a composition according to the invention, the compounds of formula I are those of formula II CH 2 = C -CO--ORI.1 -0 -R 2' 1 R where the symbols are as defined above.
Preferably component b), when present, is i) a compound of formula III CH = C - CO-O-R 4 1 K in which R is as defined above and, (II) (III) R4 is linear or branched Cl-22 alkyl, unsubstituted or substituted by one or more (preferably 1 to 3) groups selected from hydroxy, carboxy, thio or an amide group or R4 is CS-6 cycloalkyl, phenyl, naphthyl, (V) Case 154-0136 - A H3 C -n where A and R15 are as defined above; or ii) a compound of formula IV or - A --(:)- R, 5 CH = C-CO-(O-R)-O-R 2 1 1 n 2a R in which R, R, and n are as defined above and R2a is a group of a, to el (IV) co co co - (b (C 1) (.T> I _11\ I COOR 13 COOR 13 COOR 13 CO- (d CH OOR JH2 13 CO -OR 13 wh ere R13 is hydrogen, an alkali or alkaline earth metal cation or a mono-, di- or tri- Cl-a alkylamine, unsubstituted or substituted by 1 to 3 OH groups; or iii) a compound of formula V CH 2 = C - CO-MR 1) n 0---R10 1 R in which R, R, and n are as defined above and R10 is a group of the formula (V) Case 154-0136 CH 2 LO- CH CH-C CH 2 2 3 -CH 2 __CH2 -e CH3 1 CH12 OR, 1 11 _ CHS-C H 3 CH 2 1 --CH 2 - C 4H 20 where R,, is hydrogen or acetyl Preferably component c) is a combination of 0.1 to 5 % by weight C3-18 hydrocarbyl peroxides or C3- Is hydrocarbyl hydroperoxides and 0.005-2 % by weight of a polyvalent metal salt or a complex and/or 0.1 to 5 % of an aromatic amino group containing polymer accelerator, all percentages being based on the weight of components a) and b) present.
Further according to the invention there is provided a compound of formula VI CH = C-CO-(OR1) -0-R 2 1 ni (VI) where na is an integer of from 2 to 10 inclusive and the other symbols are as defined above.
Case 154-0136 Further according to the invention there is provided a compound of formula XX CH 2 = C - CO - 0 - R 1- 0 -CO I (xx) K in which the symbols are as defined above.
COOR 3 Further according to the invention there is provided a compound of formula V as defined above.
Further according to the invention there is provided a compound of formula XIV CH 2 C -CO 1-0 R 2 1 Ra (XIV) in which R. is methyl and R3 is other than Clo-le alkyl and the other symbols are as defined above.
Compounds of formula I where R2 is a group of formula a) to e) can be formed by i) reacting 1 mole of an anhydride of one of formulae L to LIV Qco \ ..1 0 CO (L) 0// 0 (LIII) ", CO 1 0 QCO 1-1 (11) 1 CO \ 0 (LII) CO 1.11 CO c (LIV) 0 CO with 1 mole of a compound of formula XVI R3 -OH (XVI) Case 154-0136 at an elevated temperature to form a compound of formula XVII HO-R2 (XVII) followed by ii) reacting 1 mole of a compound of formula XVII with 1 mole of a compound of formula XIX HO-(Rl-On-H (m) at an elevated temperature to form a compound of formula M R2-0-(R1-0),,- H (m) where R2 is as defined above followed by iii) reacting 1 mole of a compound of formula M with 1 mole of a compound of formula XXII CH2=C-COOH (XXII) R at an elevated temperature to form a compound of formula I.
In the above reactions, elevated temperature means a temperature from 40110'C.
A compound of formula VI where R3 is not alkenyl can be prepared Case 154-0136 by a) reacting 1 mole of a compound of formula VII CH2=C-CO-O-(R1-0)n.-OH 1 R (VII) with 1 mole of an acid anhydride of formula L to U above to form a compound of formula VIII R2,-0-(R1-0),,-CO-C=CH2 R (VIII) in which the symbols are as defined above, at an elevated temperature, the compound of formula VIII optionally being salted by reaction with alkali to form an alkali metal salt; followed by b) reacting 1 mole of the compound of formula VIII or a salt thereof with 1 mole of a compound of formula IX R3 - A, (IX) where A, is a group capable of being split off from R3, at elevated temperature.
other compounds of formula I can be made by known methods from known compounds.
Preferred compounds of formula IX are R3 - 0 - SO - Cl, C1-4 alkyl or cyclohexyl-chloro sulphites, di-R3-sulphates, tri-R3-phosphates, tri-R3phosphites or R3-halogen (in a suitable solvent such as hexamethyl phosphoric acid triamide). Reaction b can also be carried out in the presence of isonitrile and CU20.
Preferably the elevated temperature of reaction a) is 80-110'C and for reaction b) is 40-60'C.
Case 154-0136 Compounds of formula XX can be made by an analogous method using a compound of formula VII where na is 1 and a compound of formula VIII where R2. is a group of formula a,.
Compounds of formula XIV can be prepared by reacting a compound of formula VII where na is n and R is methyl with an anhydride of formula L to LIV followed by reacting the product with a compound of formula IX.
Compounds of formula I when n=l and R2. is derived from acrylic acid are known or can be made from known compounds by known methods.
Methyl esters of compounds of formula I (e.g. where R3 is methyl) can be reacted with linear or branched fatty alcohols to form appropriate fatty alcohol esters by known methods (eg. in the presence of alkali catalysts).
Compounds of formula III can be prepared by known methods from appropriate reactants.
Compounds of formula IV can be made by a method analogous to that for forming compounds of formula I from appropriate reactants.
Compounds of formula V can be prepared by reacting 1 mole of a compound of formula XII CH2=C-COOH (m) R with 1 mole of a compound of formula XIII Rio-O(R1-0),,-H (Xiii) Case 154-0136 where the symbols are as defined above, at an elevated temperature (e.g. at 4060OC).
Further according to the invention there is provided a homo- or copolymer containing at least 3 recurring units of formula XXX -[CH2 - C CO -(OR,),, - OR2] 1 R (m) in which the symbols are as defined above optionally together with 40-90% (based on the weight of the total composition) of component d).
Preferably the number of recurring units of formula XXX is from 3 to 50 inclusive.
Compositions according to the invention containing components a), [optionally b)j,c) and d) are useful for repairing concrete materials or surfaces. Such a composition is applied to the surface requiring repair and is allowed to harden at ambient temperatures.
The compositions or compounds according to the invention can be used alone or together with filler for impregnating and/or covering porous material, especially concrete, for example for filling cracks. Such uses described in US Patent 4,460,625.
Examples 1 to 6 1 mole of phthalic acid anhydride is reacted with 1 mole of methacrylic acid glycolester at a temperature of about 100 to form an intermediate of formula 1.
0 0 11 1 c C - 0 - CH2 CH- 0 -C --C = CH 2 1 COOH CH 3 (1 a) Case 154-0136 The compound of formula 1. is neutralised with sodium hydroxide and reacted at 400 with % mole of dimethyl sulphate. The resulting compound of formula 1 defined below is a liquid, with a viscosity, measured in a Brookfield viscosimeter, Spindle 2 at 60 rpm as given in the Table below. By an analogous method further compounds of formula 1 where the symbols are defined in the Table can be obtained from appropriate reactants.
0 B \"\ - //I c Table
Example A
0 CH 3 11 9 1 L -0- A - 0 -C -C =-- 1-, c B c Viscosi ty 1 ethylene o-phenylene methyl 60 2 ethylene o-phenylene isononyl 380 3 ethylene o-phenylene isopentyl 246 4 ethylene o-tetrahydro- methyl 65 4 phenylene propylene o-tetrahydro- methyl 66 3 phenylene 6 propylene o-phenylene methyl 56 Application Example The compound of formula 1 of example 1 and the intermediate of formula 1. are mixed with aggregate and catalysts according to the following recipe.
sand silica fume 229.2 g 23.2 g -is- compound of formula 1 of Ex 1 42.75g compound of formula 1. 2.25g dimethylaminobenzaldehyde 1.8 g cumenehydroperoxide 0.9 g cobalt naphthenate 0.9 g 300 g Case 154-0136 This composition hardens within 15 minutes and can be tested for strength after 12 hours. For dispatch to the building site, the aggregate, the monomer and the catalyst composition are packed in different packages.
3700/DMIMC

Claims (12)

Claims
1. A composition comprising a) one or more compounds of formula I CH 2 = C -CO-(OR 1)r- OR 2 1 R in which R is hydrogen or methyl, R, is linear or branched C2-8 alkylene n is an integer from 1 to 10 inclusive R2 is a group of formula a) to i) CO -co - Qco - (a) 0""(b) COOR G CH 2 CO- CO -OR 13 (e) C812 OR 11 11 _ CHS---C H 3 COOR 3 COOR Case 154-0136 (I) (c) R 3 H3 CH 3 -CH 2 ---CH 2 CH 11 -CH 2 CHj-c -0-CH 3 (h) or (d) (9) (f) CH 2 CH 3 (f) 1 -CH C 4H 2 - c20 where R3 is a linear or branched Cl22 alkyl group, linear or branched C2- 22 alkenyl, unsaturated or saturated Cs-6 cycloalkyl (e.g. cyclohexyl or cyclopentyl), phenyl, naphthyl, 1 17- Case 154-0136 H3 c - A --- n or - A R is where A is C1-6 alkylene or C2-6 alkenylene; R,, is hydrogen or acetyl; and R15 is Cl-6 alkyl; (hereinafter referred to as component a) and b) optionally one or more vinyl compounds that are other than of formula I (hereinafter referred to as component b); and c) 0.1 to 10 % (based on the weight of components a) and b) present) of two or more polymerisation catalysts (hereinafter referred to as component c), all percentages being by weight of the composition.
2. A composition according to Claim 1 containing 20 to 100% of component a) and 0 to 80% of component b).
3. A composition according to Claim 1 or Claim 2 containing 40-95% based on the total weight of composition of inorganic aggregate.
4. A composition according to any one of the preceding claims in which compound a) is a compound of formula II CH2 - C - CO - ORi'- 0 - R2# (II) R where R,' is -CH2 - CH2-; -CH2 - CH-; CH3 C2Hs -CH2 - CH--- or -(CH2)6R2r is a group of formula a' or bl CO - CrCOOR 3 ' W) Case 154-0136 CO - I COOR 3 ' where R31 is a linear or branched Cl-12 alkyl or C2-12 alkenyl'.group; and R is hydrogen or methyl.
5. A composition according to any one of the preceding claims in which component b) is selected from i) a compound of formula III CH 2 = C - CO O-R 4 1 K in which R is as defined above and, (III) R4 is linear or branched Cl-22 alkyl, unsubstituted or substituted by one or more (preferably 1 to 3) groups selected from hydroxy, carboxy, thio or an amide group or R4 is C5-
6 cycloalkyl, phenyl, naphthyl, H3 CH - A - n (b') o r - A R is -19where A and Rls are as defined in Claim 1; ii) a compound of formula IV CH 2 = C -CO -(0 -RI)- 0---R 2a OV) 1 R in which R, R, and n are as defined in Claim 1; R2a is a group of a, to el Case 154-0136 CO CO - CO - Q"' (b 1) (C 1) COOR 13 COOR 1 ( COOR 13 CO- CO - OOR 13 (d 1 CH2 (e "CO-OR 13 where R13 is hydrogen, an alkali or alkaline earth metal cation or a mono- , di- or tri- Ci-a alkylamine, unsubstituted or substituted by 1 to 3 OH groups; and iii) a compound of formula V CH 2 f CO-OR ix )n- 0---R10 (V) in which R, R, and n are as defined above and R10 is a group of the formula -CH, --CH CH 2 2 2 CH 2 CH -0-CH 3 1 g CH12 OR 11 11 _ CH 3 c H 3 where R,, is hydrogen or acetyl CH, CH 2 Case 154-0136 1 4H --CH 2 - c20 -QU) 2 6. A composition according to Claim 1 in which component c) is a combination of 0.1 to 5 % by weight C3-1s hydrocarbyl peroxides or C3- 1s hydrocarbyl hydroperoxides and 0.005-2 % by weight of a polyvalent metal salt or a complex and/or 0.1 to 5 % of an aromatic amino group containing polymer accelerator, all percentages being based on the weight of components a) and b) present.
7. A compound of formula VI CH 7- C-CO-(OR) j-0 -R 2 1 K I n in which R is hydrogen or methyl R, is linear or branched C2-8 alkylene na is an integer of from 2 to 10 inclusive; R2 is a group of formula a) to i) (VI) CO - -" CO - CO - 0 - (-T' (a) I (b) (I (c) OOR COOR QCOOR COOR 3 3 (d) i CO- CH2 % CO -OR CH(2 OR 11 P _ CHI-CH 3 (e) Case 154-0136 CH3 CH3 -CH 2 ----CH 2 - n M CH 2 1 CH 2 CHf-c -0- CH 3 (h) or (9) CH 2 CH 3(i) 1 -CH 2 - c - H20 where R3 is a linear or branched Cl-22 alkyl group, linear or branched C222 alkenyl, unsaturated or saturated Cs-6 cycloalkyl (e.g. cyclohexyl or cyclopentyl), phenyl, naphthyl, H3 CH -A or where A is C1-6 alkylene or C2-6 alkenylene; R,, is hydrogen or acetyl; and R15 is C1-6 alkyl.
8. A compound of formula XX CH 2 = C-CO-O-R 1 - 0 -CO -? 1 K COOR, A -0-RlS (XX) in which R is hydrogen or methyl R, is linear or branched C2-a alkylene where R3 is a linear or branched Cl-22 alkyl group, linear or branched C2-22 alkenyl, unsaturated or saturated C5-6 cycloalkyl (e.g. cyclohexyl or cyclopentyl), phenyl, naphthyl, 2 CH H3 A - n or- A -0- R is where A is C1-6 alkylene Or C2-6 alkenylene; R,, is hydrogen or acetyl; and R15 is C1-6 alkyl.
9. A compound of formula XIV CH = C -CO -0 ---R O--R 2 1 1- n 2 Ra (XIV) in which R, is methyl; R3 is a linear or branched Cl-22 alkyl group, linear or branched C2-22 alkenyl, unsaturated or saturated C5-6 cycloalkyl (e.g. cyclohexyl or cyclopentyl), phenyl, naphthyl, H3 CH -A - n - A R, 5 where A as C1-6 alkylene or C2-6 alkenylene; R,, is hydrogen or acetyl and RIS is Cl-6 alkyl; with the proviso that R3 is other than Clo-la. alkyl.
10. A process for preparing a compound of formula I according to Claim 1 where R2 is a group of formula a) to e) comprising i) reacting 1 mole of an anhydride of one of formulae L to LIV Q C0 "'CO 0 (11) C0 \ CIC0 (LII) 0 C0 -" (L) 0 1\ 0 (L 111) 0/ with 1 mole of a compound of formula XVI R3 -OH (XVI) Case 154-0136 CO CH2 / \ CO (LIV) 0 at an elevated temperature to form a compound of formula XVII HO-12 (XVII) followed by ii) reacting 1 mole of a compound of formula XVII with 1 mole of a compound of formula M HO-(Rj0)n-H (XIX) at an elevated temperature to form a compound of formula M R2-0-(R1-0),- H (m) where R2 is as defined above followed by iii) reacting 1 mole of a compound of formula M with 1 mole of a compound of formula MI CH2=C-COOH (XXII) R Case 154-0136 at an elevated temperature to form a compound of formula I.
11. A compound of formula I substantially as herein described with reference to any one of Examples 1 to 7.
12. A composition substantially as herein described with reference to the Application Example.
published 1989 atThe patentofftce, stateHouse. 66171 High HOlbO7n, London WC1R 4TP- pwther copies maybe obtaMedfrOInTb6P"enoMoe' Wes Branch, St Mary Cray, Orpington, Kent BPZ 3RD'prInted by Multiplex techniques ltd. St Mary Cray, Kent. Cox'- 1/87
GB8914922A 1988-07-01 1989-06-29 New vinyl esters and their use in the building industry Expired - Lifetime GB2220204B (en)

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GB2220204A true GB2220204A (en) 1990-01-04
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AT (1) AT397383B (en)
AU (1) AU631798B2 (en)
BE (1) BE1004043A3 (en)
CA (1) CA1335508C (en)
CH (1) CH679585A5 (en)
DE (1) DE3920795C2 (en)
ES (1) ES2017025A6 (en)
FR (1) FR2633629B1 (en)
GB (1) GB2220204B (en)
HK (1) HK10595A (en)
IT (1) IT1232153B (en)

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* Cited by examiner, † Cited by third party
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US5596036A (en) * 1991-06-14 1997-01-21 Sandoz Ltd. Hardenable acrylic monomer compositions
US5712337A (en) * 1992-06-11 1998-01-27 Mbt Holding Ag Hardenable acrylic monomer compositions
EP0843184A2 (en) * 1996-11-18 1998-05-20 Menicon Co., Ltd. Ocular lens material
EP0854369A2 (en) * 1997-01-20 1998-07-22 Menicon Co., Ltd. Ocular lens material

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Publication number Priority date Publication date Assignee Title
GB2256645A (en) * 1991-06-14 1992-12-16 Sandoz Ltd Hardenable monomer composition
FR2677656A1 (en) * 1991-06-14 1992-12-18 Sandoz Sa CIPO - Patent - 2496090 Canadian Intellectual Property Office Symbol of the Government of Canada CA 2583299 NOVEL CURABLE MONOMERIC COMPOSITIONS BASED ON (METH) ACRYLATE AND THEIR USE AS SOIL COATING AND CONCRETE SURFACES.
BE1005805A3 (en) * 1991-06-14 1994-02-01 Sandoz Sa New monomer compositions.
GB2256645B (en) * 1991-06-14 1995-03-15 Sandoz Ltd Monomer compositions
US5596036A (en) * 1991-06-14 1997-01-21 Sandoz Ltd. Hardenable acrylic monomer compositions
US5712337A (en) * 1992-06-11 1998-01-27 Mbt Holding Ag Hardenable acrylic monomer compositions
EP0603133A1 (en) * 1992-12-15 1994-06-22 Sandoz Ltd. Monomer compositions for the construction industry
EP0843184A2 (en) * 1996-11-18 1998-05-20 Menicon Co., Ltd. Ocular lens material
EP0843184A3 (en) * 1996-11-18 1999-01-07 Menicon Co., Ltd. Ocular lens material
EP0854369A2 (en) * 1997-01-20 1998-07-22 Menicon Co., Ltd. Ocular lens material
EP0854369A3 (en) * 1997-01-20 1999-01-27 Menicon Co., Ltd. Ocular lens material

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DE3920795A1 (en) 1990-02-01
CH679585A5 (en) 1992-03-13
IT8948137A0 (en) 1989-06-28
ATA160189A (en) 1993-08-15
GB8914922D0 (en) 1989-08-23
ES2017025A6 (en) 1990-12-16
GB2220204B (en) 1992-03-11
DE3920795C2 (en) 1999-06-24
JPH0247115A (en) 1990-02-16
AU631798B2 (en) 1992-12-10
HK10595A (en) 1995-02-03
FR2633629B1 (en) 1993-07-23
JP2783847B2 (en) 1998-08-06
FR2633629A1 (en) 1990-01-05
CA1335508C (en) 1995-05-09
AT397383B (en) 1994-03-25
BE1004043A3 (en) 1992-09-15
IT1232153B (en) 1992-01-25
AU3721289A (en) 1990-01-04

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