GB2212807A - Polymeric compositions containing flame retardant and oxanilide - Google Patents
Polymeric compositions containing flame retardant and oxanilide Download PDFInfo
- Publication number
- GB2212807A GB2212807A GB8827132A GB8827132A GB2212807A GB 2212807 A GB2212807 A GB 2212807A GB 8827132 A GB8827132 A GB 8827132A GB 8827132 A GB8827132 A GB 8827132A GB 2212807 A GB2212807 A GB 2212807A
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- Prior art keywords
- hydrogen
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- 4alkyl
- halogen
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- 239000000203 mixture Substances 0.000 title claims description 18
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 title description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title description 5
- 239000003063 flame retardant Substances 0.000 title description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- -1 hydroxy, phenyl Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 3
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Hydrogenated Pyridines (AREA)
Description
1 Case 153-5218 2212807 POLYMERIC COMPOSITIONS CONTAINING FLAME RETARDANT
AND OXANILIDE The invention relates to a polymeric composition containing a phosphorus- containing flame retardant and an oxanilide or hindered amine light stabiliser.
According to the invention there is provided a methylmethacrylate homopolymer or copolymer composition containing a) an oxanilide or 2,2,6,6tetramethylpiperidine light stabiliser (hereinafter defined as component a); and b) a phosphorus-containing flame retardant (hereinafter defined as component b).
Preferably when component a) is an oxanilide light stabiliser, it is a compound of formula I 2)2 (R -CO-CO-N- R.
1 R 2)2 (1) in which each R, independently is selected from hydrogen, Cl-lealkyl, Cl-lealkoxy, halogen, hydroxy, phenyl and phenoxy; and each R2, independently, is selected from hydrogen, halogen, hydroxy, Cl-8alkyl and Cl-Balkoxy; and each R, independently, is hydrogen or methyl.
Case 153-5218 Preferably R, is R,, where R,, is selected from hydrogen, hydroxy, Cl- 4alkyl and Cl-4alkoxy, more preferably R, is hydrogen.
Preferably R2 is R2F where R2 is selected from hydrogen, hydroxy, Cl4alkyl and Cl-4alkoxy, more preferably on phenyl group A and B, one R2 is hydrogen and the other R2 is R211 where R2'T is Cl-4alkyl or Cl-4alkoxy. Preferably R211 on ring A is a Cl-4alkyl and on ring B R211 is a Cl4alkoxy.
Preferably R is hydrogen.
Preferably R2 is in the ortho position.
Preferably when component a) is a 2,2,6,6-tetramethylpiperidine compound, it is a compound of formula II CH3 H " 3 12 R_ -N /. 11 CH 3 CH3 (H) in which RIO is selected from hydrogen, Cl-ealkyl, oxygen or -COR15; where RI5 is C(R)CH2, Cl-6alkyl, phenyl, -NR17Rle, -CO-C6Hs, -CH2C6H5, CO0C1-12alkyl or -COOH; R17 is hydrogen, Cl-12alkyl, CS-6cycloalkyl (preferably cyclohexyl), phenyl, pheny1C1-4alkyl or Cl-12alkylphenyl and R18 is hydrogen or Cl-12alkyl; R,, is hydrogen, Cl-22alkyl, Cl-22alkoxy, -N(R)-CO-CO-R20; or -N-C(R)=N- 121; 1 H where R20 is an amide forming group and R21 is Cl-18alkyl, phenyl, unsubstituted or substituted by 1 to 3 groups selected from Cl-lealkyl, Cl-4alkoxy and halogen; or R,, is CH3, CH3 R12 "" Cru H3 H 3 v 1 Case 153-5218 and R12 is hydrogen or Cl-8alkyl; or R,, and R12 together with the C-atom to which they are attached, form a group of formula a) /(CH) 11 O-L'/ "I C /, 1 // c- N-C 2-4 alkylene-COOCI-22alkyl (a) More preferred 2,2,6,6-tetramethylpiperidinyl compounds are of formula IIa or IIb CH 3 CH 33 tCH3 H R 1 2 3 R' to - R C-(CH)-g--C-0 2 bl CH3 H3 0 0 H3 H3 CH 3 3 /(CH2)11 ---V R'0-N-CH2CH2-CO0C8-18alkyl CH H 3 3 (Ha) (IIb) where R101 is hydrogen -Cl-4alkyl or -CO-BI5twhere R151's C1-4alkyl or - CO-OC1-4alkyl; and R12f is hydrogen or methyl (preferably R12r is hydrogen).
Preferably component b) is a compound of formula III or IV 11 5 0 R 4 0 R 0-P CHO-P--HO-P-OR 3 1 3 1 1 R 3 0 R 3 0---1R 3 n (M) i 1 R R CH-0 R 7 H 0 R \X U P-O-R 6 2 Case 153-5218 C-(CH 2 R 5)2 (IV) in which each R3, independently, is selected from Cl-6alkyl, unsubstituted or mono- or di-substituted by halogen, C2-6alkenyl, unsubstituted or substituted by one halogen and/or by one Cl-4alkoxy; or R3 is a phenyl group or hydrogen; n is an integr from 1 to 10; R4 is Cl- 17alkyl; R is hydrogen or methyl; each Rr, independently is halogen or hydrogen; each R6 independently is Cl-4alkylene; X is 0 or S; and R7 has a significance of R3 independent of R3 Preferably R20 has the preferred significances of R4 of GB Published Patent Application No. 2180537 (Application No. 8621894); the contents of which and preferences of which are incorporated herein by reference.
Any Cl-lealkyl is preferably Cl-ealkyl; any Cl-salkyl is preferably Cl4alkyl and any Cl-4alkyl is preferably methyl or ethyl.
Preferably in this Specification, any halogen is fluoro, chloro, bromo or iodo, more preferably chloro or bromo.
Preferably R3 is R3F where R3t is Cl-4alkyl monosubstituted by chloro or bromo; more preferably R3 is R311 where R311 is -CH2CH2C11 Preferably R4 is R4t where R4t is Cl-4alkyl; more preferably R4 is R41' where R4" is -CH3 or -C2H5, most preferably -CH3.
t' Case 153-5218 Preferably R4 is R4f where R4r is Cl-4alkyl; more preferably R4 is R411 where R411 is -CH3 or -C2H5, most preferably -CH3.
Preferably n is, on average, 2.
Preferably R5 is R51 where R51 is hydrogen, chloro or bromo, more preferably chloro.
Preferably R6 is R61 where R60 is methylene or ethylene; more preferably methylene.
Preferred compounds of formula III are those of formula III, 0 7 CH 0 CH 0 (R CH CH 11 1 3 if 1 1 3 U 19 2 20+2;r--P--CH-0-P j CH- 0-P-CH 2 CH 2 R 19 1 n# OCH2 CH 2 R, 9 OCH 2 CH 2 R 19 where n, is 2; and each R19, independently, is a halogen; preferably each R19 is chlorine.
Preferred compounds of formula IV are of formula IV, R CH-0 2 R/ \CH 0 7 2 P-O -CH C(CH 2 c]) 2 2 where each R7t, independently, is hydrogen, ethyl or methyl; preferably R7t is methyl; and X is 0 or S. Preferably X is 0.
(IV,) Preferably 0.05 to 1 %, more preferably 0.1 to 0.5 % of Component a is present in a composition according to the invention.
Case 153-5218 Preferably 5 to 20 %, more preferably 10 to 15 % of Component b is present in a composition according to the invention. All percentages are based on the amount of polymer present in the composition.
Compounds of formula I to III are known or may be prepared by known methods from known compounds.
Methylmethacrylate polymers according to the invention can be prepared according to known methods from appropriate reactants, optionally with comonomers.
For copolymerisation the following alpha, beta-unsaturated comonomers may be used.
C2_8alkyl ester of methacrylic acid, Cl-Balkyl ester of acrylic acid, Clealkyl ester of alpha-cyanoacrylic acid, (as the ethyl, butyl or cyclohexyl ester), styrene, methylstyrene, acrylonitrile, methacrylonitrile or alpha-chloroacrylonitrile.
A preferred copolymer according to the invention is formed by the polymerisation of methylmethacrylate in the presence of glycidylacrylate and/or glycidylmethaerylate, preferably in the presence of glycidyl methacrylate. Preferably in such copolymer 0.1 to 10 X, more preferably 0. 5 to 6 % by weight (based on the weight of methacrylate and other comonomers if present) of the glycidyl compound is present in the copolymer of the invention.
The working of components a) and b) into a polymer or copolymer according to the invention, can be carried out according to known methods. For example, components a) and b) can be added to the monomer or prepolymer at room or elevated temperatures. The polymers and copolymers according to the invention can be prepared by known methods from appropriate reactants, preferably by block polymerisation in the presence of a polymerisation catalyst, for example azo-bis-iso-butyronitrile, dibenzoylperoxide, dilaurylperoxide or tertiary butoxyperpivalate. Components a) and b) can also be worked into the melted polymer or copolymer by known methods such as k Case 153-5218 extrusion and the polymers can be converted into shaped articles. Preferably 3 to 30 %, more preferably 5 to 25 % by weight of components a) and b) in the polymer based on the weight of polymer or monomers is used.
- one preferred method for preparing a copolymer according to the invention is copolymerisation with glycidyl acrylate or glycidylmethacrylate. By using the glycidyl acrylate or glycidyl methacrylate a lesser amount of component a) and b) may be used to achieve flameproofing. In such a case the preferred amount of components a) and b) is from 3 to 25 % more preferably 8 to 15 % by weight of the polymer or of the comonomer used.
Further additives can be added to a polymer or copolymer according to the invention such as polymerisation regulators, softeners, U.V. light stabilisers, antioxidants and pigments.
The polymers and copolymers of the invention an be made into various shaped articles such as sheets, tubing or foils by known methods.
For the avoidance of doubt, reference to component a) or b) includes mixtures of component a) or b) or a mixture of one of more compounds of component a) or b) with one or more other flameproofing agents. Further, in this specification where a range is given, the figures defining the range are included therein.
Polymethylmethacrylate polymers and copolymers according to the invention have good light fastness properties and as well as good flameproofing properties.
The invention will now be illustrated by the following Examples in which all parts and percentages are by weight and all temperatures are in OC.
ple 1 47.5 g of freshly distilled methylmethacrylate are mixed with 0.04 g of dilaurylperoxide, 0.03 g of azoisobutyric acid dinitrile and 2.5 g of the compound of formula la Case 153-5218 - CH OCH CH Cl CH H CH Cl 3 a 2 2 a 3 2 2 (Cl CH 2 CH20) T_ p H-0 -p CHO-p==0 11 0 where n is on average 2 and 0.1 g of the compound of formula 1b cc H-CO-CO-M-P C2H5 6 H 2 CH2 1 0b) 0C2H5 0a) The transparent solution is kept at 115C for 7 minutes and then poured between glass plates, which are separated by a 3 mm thick rubber spacer and sealed with pressure sensitive tape. Subsequently, the glass plates are kept for 16 hours at 50C in a water bath and then for 4 hours at 115C in an oven.
The resulting cast polymethylmethacrylate sheets have good flameproofing properties and good light fastness properties.
Exaaple, 2 Mold injection polymethyl methacrylate specimens are prepared by dry blending 0.1 g of the compound of formula lb (of Example 1) and 2.5 g of'the compound of formula 2a CH 3 CHj--0 0 ----OCH >111 2 C (CH 2 C]) 2 (2a CH CH-0 3 2 2 io Case 153-5218 with commercially available mold grade PMMA (polymethylmethacrylate). Injection moulding to form 3 mm plates is carried out in an Arburg 200 injection moulding extruder machine at 200-2200C.
The polymethylmethacrylate that is extruded has good light fastness and good flameproofing properties.
Exaaples 3 and 4 Example 2 is repeated using instead of the U.V. absorber 0.1 g of the compound of formula 3a or 4a 3 H3 AH2)11 ---V H1 1 0-N-CH2CH2-COOC 12 H25(n) (3a) CH H, 3 3 CH 3 CH 30 CHn3 H 3 H C-(CH H tR 2 CH3 3 0 0 H3 H3 (4a) CTIAIMS containing a) - Case 153-5218 A methylmethacrylate polymer or copolymer composition an oxanilide or 2,2,6,6-tetramethylpiperidine light stabiliser (hereinafter defined as component a); and b) a phosphorus-containing flame retardant (hereinafter defined as component b).
Claims (1)
- 2. A composition according to Claim 1, in which component a) is a compoundof formula I91 (R 2)2 -CO-CO-N-, 1 1 j OR K 1 R2) 2 (I) in which each R, independently is selected from hydrogen, Cl-16alkyl. Cl- 18alkoxy, halogen, hydroxy, phenyl and phenoxy; and each R2, independently, is selected from hydrogen, halogen, hydroxy. Cl _Balkyl and Cl-8alkoxy; and each R. independently, is hydrogen or methyl.3. A composition according to Claim 2, in which R, is R,' where R,, is hydrogen. hydroxy, Cl-4alkyl or Cl-4alkyl, R2 is R2' where R2' is hydrogen.. hydroxy, Cl-4alkyl or Cl-4alkoxy and R is hydrogen.4_ A composition according to Claim 1, in which component a) is a compound of formula II r 1 CH 1H3 "3 12 R-0N / - ' 11 CH 3 CH3 Case 153-5218 (I I) in which R10 is selected from hydrogen, Cl-Balkyl, oxygen or -COR15: where R15 is C(R)=CH2, Cl-6alkyl, phenyl, -NR17R,B, -CO-C6H5, -CH2C6BS, CO0C1-12alkyl or -COOB; R17 is hydrogen, Cl-12alkyl, CS-6cycloalkyl (preferably cyclohexyl), phenyl, pheny1C1-4alkyl or Cl-12alkylphenyl and R18 is hydrogen or Cl-12alkyl; R,, is hydrogen. ("1-22alkyl, Cl-22alkoxy, -N(R)-CO-CO-R20; or -N-C(R)N- R211 H where R20 is an amide forming group and R21 is Cl-18alkyl, phenyl, unsubstituted or substituted by 1 to 3 groups selected from Cl-lealkyl, Cl-4alkoxy and halogen; or R21 is CH3, CH3 R12 H 3 H3 and R12 is hydrogen or Cl-salkyl; or R,, and R12 together with the C-atom to which they are attached, form a group of formula a) /(CH 2)11 O-LI/ I-C alkylene-COOC alkyl (a) 2-4 1-22 0 Case 153-5218 5. A composition according to Claim 4, in which Component a) is a compound of formula IIa or IIb CH 3 CH 3 2 -R / 1 i tC5 R ' RI CH3 H 3 H C - (CH2) jCee -C -R,'Q CH3 3 0 0 H3 H3 CH3 (CH2)11 3 Rto tO-N.-CH2CH2-CO0C8-,8alkyl CH H 3 3 (IIa) (M) where R101 is hydrogen -Cl-4alkyl or -CO-Rs' where R51 is Cl-4alkyl or -CO-OC1-4alkyl; and R12' is hydrogen or methyl 6. A composition according to any one of the preceding claims in which Component b) is a compound of formula III or IV 0 0 4 es R 3 0-P- CHO-P- 1 1 R 301 R 3 0 1 n R 1 R CH-01\ c R CH-0 7 1 R R 0 A at -CHO-P-OR R 3 P-O-R6 3 2 (III) C- (CH 2 R 5)2 (IV) in which each R3, independently, is selected from Cl6alkyl, I Q p 1 Case 153-5218 unsubstituted or mono- or di-substituted by halogen, C2-6alkenyl, unsubstituted or substituted by one halogen and/or by one CI-4alkoxy; or R3 is a phenyl group or hydrogen; n is an integer from 1 to 10; R4 is Cl-17alkyl; R is hydrogen or methyl; each R.5 independently is halogen; or hydrogen each R6 independently is Cl-4alkylene; X is 0 or S; and R7 has a significance of R3 independent of R3 7. A composition according to Claim 6, in which the compound of formula III is of formula III' $1 CH 3 0 CH 0 (R CH CH G-,p. 3 to 19 2 2 2 H-0'Ll P-CH2CH 2 R, 9 L /P n 1 '- '-1 CH R OCH 2CH2R 19 u2 2 19 (111.) in which n' is 2; and each R19 is a halogen.8. A composition according to Claim 6, in which the compound of formula IV is of formula IV' L_ R ' CH-0 7 2 X R /. c \ CH-0 / P-O-CHf- 7 -C(CH 2 c]) 2 (IV I) where each R7f independently, is hydrogen, ethyl or methyl.14 - Case 153-5218 9. A process for flameproofing a methylmethacrylate polymer comprising applying Component a) and Component b) as defined in any one of the preceding claims.r !P 10. A methylmethacrylate composition substantially as herein described with reference to Examples 1 to 3.3700/DMIKC z Published 1989 atThe Patent Offloe, State House, 66171 High Holborn, London WCIR 4TP. Further copies maybe obtained from The patent oince. Sales Branch, St Mary Cray, Orpington. Kent BES 3RD. Printed by Multiplex techniques ltd, St Mary Cray, Kent, Con. 1187
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878727452A GB8727452D0 (en) | 1987-11-24 | 1987-11-24 | Organic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8827132D0 GB8827132D0 (en) | 1988-12-29 |
| GB2212807A true GB2212807A (en) | 1989-08-02 |
| GB2212807B GB2212807B (en) | 1991-08-14 |
Family
ID=10627436
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878727452A Pending GB8727452D0 (en) | 1987-11-24 | 1987-11-24 | Organic compounds |
| GB8827132A Expired - Lifetime GB2212807B (en) | 1987-11-24 | 1988-11-21 | Light stabilized flame retarding methylmethacrylate polymer |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878727452A Pending GB8727452D0 (en) | 1987-11-24 | 1987-11-24 | Organic compounds |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH01167357A (en) |
| CH (1) | CH676242A5 (en) |
| DE (1) | DE3838480A1 (en) |
| FR (1) | FR2623515A1 (en) |
| GB (2) | GB8727452D0 (en) |
| IT (1) | IT1224575B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018033502A1 (en) * | 2016-08-15 | 2018-02-22 | Evonik Röhm Gmbh | Acrylic materials for use in an ultraviolet light engine |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9121575D0 (en) * | 1991-10-11 | 1991-11-27 | Sandoz Ltd | Improvements in or relating to organic compounds |
| EP1148090A1 (en) * | 2000-04-17 | 2001-10-24 | Clariant Finance (BVI) Limited | Flame retardant polymers |
| DE10040060A1 (en) * | 2000-08-11 | 2002-02-28 | Roehm Gmbh | Improved tanning bed material |
| DE10311641A1 (en) * | 2003-03-14 | 2004-09-23 | Röhm GmbH & Co. KG | Polymethyl methacrylate shaped body or molding useful as a tanning aid contains UV-stabilizers and UV-absorbers with specified transmission values |
| FR2892422B1 (en) * | 2005-10-20 | 2011-08-05 | Arkema | FLAME RETARDANT METHACRYLIC COMPOSITION |
| EP1777257B1 (en) * | 2005-10-20 | 2018-08-22 | Arkema France | Fireproof methacrylic composition |
| US8466096B2 (en) | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
| DE102008043719A1 (en) | 2008-11-13 | 2010-05-20 | Evonik Röhm Gmbh | Molding compounds for the production of solar cell modules |
| DE102008043713A1 (en) | 2008-11-13 | 2010-05-20 | Evonik Röhm Gmbh | Production of solar cell modules |
| DE102010030508A1 (en) | 2010-06-25 | 2011-12-29 | Evonik Röhm Gmbh | Production of solar cell modules |
| JP6346305B2 (en) * | 2014-12-05 | 2018-06-20 | 大日精化工業株式会社 | Manufacturing method of additive for granular resin, additive for granular resin, thermoplastic resin composition, and molded product obtained by the manufacturing method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH501699A (en) * | 1965-12-08 | 1971-02-26 | Ciba Geigy Ag | Use of symmetrical oxalic acid diarylamides as ultraviolet protection agents for organic materials outside the textile industry |
| DE2913853A1 (en) * | 1979-04-06 | 1980-10-23 | Roehm Gmbh | METHOD FOR POLYMERIZING METHYL METHACRYLATE |
| CH667275A5 (en) * | 1985-03-22 | 1988-09-30 | Sandoz Ag | FLAME RETARDED METHYL METHACRYLATE POLYMER AND COPOLYMER. |
-
1987
- 1987-11-24 GB GB878727452A patent/GB8727452D0/en active Pending
-
1988
- 1988-11-12 DE DE3838480A patent/DE3838480A1/en not_active Withdrawn
- 1988-11-17 FR FR8815082A patent/FR2623515A1/en not_active Withdrawn
- 1988-11-21 IT IT8848573A patent/IT1224575B/en active
- 1988-11-21 GB GB8827132A patent/GB2212807B/en not_active Expired - Lifetime
- 1988-11-21 CH CH4307/88A patent/CH676242A5/de not_active IP Right Cessation
- 1988-11-22 JP JP63293733A patent/JPH01167357A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018033502A1 (en) * | 2016-08-15 | 2018-02-22 | Evonik Röhm Gmbh | Acrylic materials for use in an ultraviolet light engine |
Also Published As
| Publication number | Publication date |
|---|---|
| CH676242A5 (en) | 1990-12-28 |
| DE3838480A1 (en) | 1989-06-08 |
| GB2212807B (en) | 1991-08-14 |
| GB8727452D0 (en) | 1987-12-23 |
| IT8848573A0 (en) | 1988-11-21 |
| JPH01167357A (en) | 1989-07-03 |
| GB8827132D0 (en) | 1988-12-29 |
| FR2623515A1 (en) | 1989-05-26 |
| IT1224575B (en) | 1990-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921121 |