DE1569260A1 - Flammen- und wetterbestaendige Masse auf der Grundlage von Methacrylsaeuremethylester - Google Patents
Flammen- und wetterbestaendige Masse auf der Grundlage von MethacrylsaeuremethylesterInfo
- Publication number
- DE1569260A1 DE1569260A1 DE19631569260 DE1569260A DE1569260A1 DE 1569260 A1 DE1569260 A1 DE 1569260A1 DE 19631569260 DE19631569260 DE 19631569260 DE 1569260 A DE1569260 A DE 1569260A DE 1569260 A1 DE1569260 A1 DE 1569260A1
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- substituted
- percent
- weight
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 title description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 33
- 235000011007 phosphoric acid Nutrition 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 239000003365 glass fiber Substances 0.000 claims description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 10
- -1 phosphorus compound Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 8
- 150000004702 methyl esters Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 17
- 238000007792 addition Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- IAQNLUJLASSNLX-UHFFFAOYSA-N 2-bromoethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCBr IAQNLUJLASSNLX-UHFFFAOYSA-N 0.000 description 4
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 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 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- ANHAEBWRQNIPEV-UHFFFAOYSA-N 2-chloroethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCCl ANHAEBWRQNIPEV-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 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
- PMGHIGLOERPWGC-UHFFFAOYSA-N Bis-(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(O)OCCCl PMGHIGLOERPWGC-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical class CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003058 plasma substitute Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US241134A US3347818A (en) | 1962-11-30 | 1962-11-30 | Methyl methacrylate compositions containing halogen substituted acid alkyl esters of orthophosphoric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1569260A1 true DE1569260A1 (de) | 1970-05-06 |
Family
ID=22909400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631569260 Pending DE1569260A1 (de) | 1962-11-30 | 1963-11-13 | Flammen- und wetterbestaendige Masse auf der Grundlage von Methacrylsaeuremethylester |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3347818A (en, 2012) |
| BE (1) | BE640389A (en, 2012) |
| DE (1) | DE1569260A1 (en, 2012) |
| GB (1) | GB1062598A (en, 2012) |
| NL (2) | NL301173A (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666712A (en) * | 1970-01-02 | 1972-05-30 | Stauffer Chemical Co | Flame retardant polymethyl methacrylate compositions |
| DE2237875B2 (de) * | 1972-08-02 | 1975-02-06 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zum Flammwidrig-Ausrüsten brennbarer Thermoplaste |
| JPS5610337B2 (en, 2012) * | 1972-09-08 | 1981-03-07 | ||
| JPS5534267A (en) * | 1978-09-04 | 1980-03-10 | Mitsui Toatsu Chem Inc | Fiberglass reinforced resin composition |
| DE3311832A1 (de) * | 1983-03-31 | 1984-10-04 | Röhm GmbH, 6100 Darmstadt | Flammhemmend ausgeruestete polymethylmethacrylat-formmasse |
| FR2831545B1 (fr) * | 2001-10-31 | 2005-07-01 | Atofina | Materiau polymere methacrylique resistant au test du fil incandescent |
| EP1461383B2 (en) * | 2001-12-05 | 2012-06-06 | Isola Laminate Systems, Corp. | Thermosetting resin composition for high performance laminates |
| FR2863621B1 (fr) * | 2003-12-12 | 2006-03-03 | Arkema | Materiau polymere methacrylique a resistance au feu amelioree |
| FR2863622B1 (fr) * | 2003-12-12 | 2006-03-03 | Arkema | Materiau polymere methacrylique a resistance au feu amelioree |
| US11548245B2 (en) | 2013-11-22 | 2023-01-10 | Johns Manville | Fiber-containing prepregs and methods and systems of making |
| US9815954B2 (en) | 2013-11-22 | 2017-11-14 | Johns Manville | System for producing a fully impregnated thermoplastic prepreg |
| US11198259B2 (en) | 2015-07-08 | 2021-12-14 | Johns Manville | System for producing a fully impregnated thermoplastic prepreg |
| US12319016B2 (en) | 2015-07-08 | 2025-06-03 | Johns Manville | System for producing a fully impregnated thermoplastic prepreg |
| US11534991B2 (en) | 2015-07-08 | 2022-12-27 | Johns Manville | System for producing a fully impregnated thermoplastic prepreg |
| SI3138870T1 (sl) * | 2015-09-03 | 2024-07-31 | Johns Manville | Sistem in postopek za izdelavo popolnoma impregniranega termoplastičnega preprega in prepreg |
| US10857744B2 (en) | 2018-04-03 | 2020-12-08 | Johns Manville | System for producing a fully impregnated thermoplastic prepreg |
| US10717245B2 (en) | 2018-04-03 | 2020-07-21 | Johns Manville | System for producing a fully impregnated thermoplastic prepreg |
| US12220879B2 (en) | 2021-02-11 | 2025-02-11 | Johns Manville | Lightweight thermoplastic composite products and methods of making same |
| US11879042B2 (en) * | 2021-08-02 | 2024-01-23 | B/E Aerospace, Inc. | Fire resistant thermoplastic-based resin for fiber-reinforced composites |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500023A (en) * | 1946-03-16 | 1950-03-07 | Du Pont | Polymerization of substituted ethylenes containing organic coloring matter in presence of azo compounds |
| GB721447A (en) * | 1951-09-05 | 1955-01-05 | Peter Dumaresq Sheridan Young | Improvements in or relating to a method of making laminated structures |
| BE598179A (en, 2012) * | 1959-12-14 | |||
| US3251785A (en) * | 1961-02-14 | 1966-05-17 | Socony Mobil Oil Co Inc | Flame retardant polyurethane foam and method for forming same |
-
0
- NL NL124954D patent/NL124954C/xx active
- NL NL301173D patent/NL301173A/xx unknown
-
1962
- 1962-11-30 US US241134A patent/US3347818A/en not_active Expired - Lifetime
-
1963
- 1963-11-13 DE DE19631569260 patent/DE1569260A1/de active Pending
- 1963-11-25 BE BE640389A patent/BE640389A/xx unknown
- 1963-11-27 GB GB46927/63A patent/GB1062598A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1062598A (en) | 1967-03-22 |
| NL301173A (en, 2012) | |
| NL124954C (en, 2012) | |
| US3347818A (en) | 1967-10-17 |
| BE640389A (en, 2012) | 1964-05-25 |
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