CA2137111A1 - Clea, expandable, flame-retardant coating compositions - Google Patents
Clea, expandable, flame-retardant coating compositionsInfo
- Publication number
- CA2137111A1 CA2137111A1 CA002137111A CA2137111A CA2137111A1 CA 2137111 A1 CA2137111 A1 CA 2137111A1 CA 002137111 A CA002137111 A CA 002137111A CA 2137111 A CA2137111 A CA 2137111A CA 2137111 A1 CA2137111 A1 CA 2137111A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- coating composition
- substituted ammonium
- coating
- salts
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
- C09D5/185—Intumescent paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Fireproofing Substances (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Abstract
The clear, expandable, flame-retardant coating composi-tions comprise at least from 10 to 70% by weight of a film-forming binder, from 0 to 40% by weight of at least one substance which is carbonized under the effect of heat, from 0 to 40% by weight of an expansion agent, from 0 to 5% by weight of dispersants and from 0 to 25% by weight of fillers.
In these compositions, aqueous synthetic-resin disper-sions are present as binder and ammonium salts of alkyl phosphates are present as substance which is carbonized under the effect of heat and/or as expansion agent, and as acid donor, in a quantity of from 1 to 50% by weight.
In these compositions, aqueous synthetic-resin disper-sions are present as binder and ammonium salts of alkyl phosphates are present as substance which is carbonized under the effect of heat and/or as expansion agent, and as acid donor, in a quantity of from 1 to 50% by weight.
Description
The present invention relates to clear, ~YpAn~Ahle, flame-retardant coating compositions which comprise at least from 10 to 70% by weight of a film-forming b5 from O to 40% by weight of at least one substance which i8 carbonized under the effect of heat, from O to 40% by weight of an ~YpAn~ion agent, from O to 5% by weight of dispersants and from O to 25% by weight of fillers.
Clear, flame-retardant coating compositions are known, for example for wood or plastics, which are based on a binder dissolved in organic solvents and which contain a substantial proportion of chlorinated paraffins (cf.
Bhatnagar and Vergnaud in: "Fire Safety Journal" 4 (3), 163-7 and "Paintindia" 32 (1) 3-6, 14; 1982).
Disadvantages of the known clear, flame-retardant coating compositions are that they give off solvent vapors on drying and contain organically bonded halogen, whereby corrosive and toxic gases are released as the coating compositions break down.
The object of the present invention is therefore to specify clear, expandable coating compositions which possess flame-retardant properties but which break down without releasing halogen-contA;n;ng compounds. This is ~I371Il achieved in accordance with the invention in that the coating compositions contain aqueous synthetic-resin dispersions as builder, and ammonium salts of alkyl phosphates as substance which is carbonized under the effect of heat and/or as ~Yr~n~ion agent and as acid donor.
Furthermore, the coating compositions according to the invention may also, optionally, have compositions in which a) mo~o~lkyl phosphates are present;
b) dialkyl phosphates are present;
c) the salts are hydroxyalkyl-substituted ammonium salts;
d) monoethanolamine is used as hydroxyalkyl-substituted ammonium;
e) diethanolamine is used as hydroxyalkyl-substituted ~mmonium;
f) triethanolamine is used as hydroxyalkyl-substituted ammonium;
0 g) the ~alts are alkyl-substituted ammonium salts;
~137111 h) the alkyl radical has 1 to 6 carbon atoms;
i) the salts are aryl-substituted ammonium salts.
The ammonium salts of alkyl phosphates which are present in the coating compositions according to the invention can be prepared, for example, by the process known from US-A-4,118,443.
In the coating compositions according to the invention it is also possible for mixtures of monoalkyl phosphates and dialkyl phosphates to be present.
The ammonium salts of alkyl phosphates which are present in the coating compositions according to the invention do not only have a flame-retardant action but also give the compositions plasticizing properties. They therefore have a positive effect on the film tear resistance of the flame-retardant coating compositions and can therefore be used as complete substitutes for chlorinated paraffins and other halogen-cont~;ning additives, for example tris(2-chloroethyl) phosphate (TCEP) or tris(2-chloro-isopropyl) phosphate (TCPP).
In the examples below, flame-retardant coating composi-tions are prepared and their effectiveness is determined.
The insulation efficiency of the intumescent paints prepared using these coating compositions was tested in accordance with DIN 4102, part 2 (1977) in a small-scale 213711 ~
test set-up according to DIN 4102, part 8 (1986), while the testing of the surface quality was carried out visually.
Example 1 (Cn~rArative example) The following components were introduced in succession into a stirred vessel fitted with a dissolver disk:
16.8 % by weight of water 3 % by weight of ~Tylose 0.2 % by weight of ~Lopon 890 11 % by weight of A~;um dihydrogen phosphate % by weight of tris(hydroxyethyl) isocyanurate 62 % by weight of ~Maprenal LH 692 2 % by weight of chlorinated paraffin 50, liquid.
Example 2 (Comparative example) The same coating composition as in Example 1 was prepared, but ~Urecoll HM was used instead of ~Maprenal LH 692.
The coating was clear and the surface of the metal panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 3 (Comparative example) The same coating compoæition as in Example 1 was prepared, but without the chlorinated paraffin component.
The coating was clear and the surface of the panel provided with this coating composition was rough and traversed by fine crackæ.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 4 (Comparative example) The same coating composition as in Example 1 was prepared, but 59% by weight of ~Urecoll HM and 4% by weight of ~Rauramin were u~ed instead of 62% by weight of ~Maprenal LH 692.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 met the requirements of the fire resistance class F 30.
Example 5 (Comparative example) The same coating composition as in Example 1 was prepared, but 2% by weight of tris(2-chloroethyl) phos-phate were used instead of 2% by weight of chlorinated paraffin 50, liquid.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 6 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin 50, liquid, 14% by weight of a monoethanol-ammonium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, were used. At the same time the tris(hydroxy-ethyl) isocyanurate was reduced to 4% by weight.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 7 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of - ~;um dihydrogen phosphate and 2% by weight of chlorinated paraffin, 15% by weight of a monoethanol~mmonium salt of the ~Rnapsack cleaner component MPS, adjusted to a pH of 7, were used; at the same time the quantity of tris-(hydroxyethyl) isocyanurate was reduced to 3% by weight.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 8 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin, 15% by weight of a triethanolammonium salt of the ~Knapsack phosphate MDE, adjusted to a pH of 7, were used; at the same time the tris(hydroxyethyl) iso-cyanurate was replaced by 2% by weight of dicyandiamide.
The coating was clear and the surface of the panelprovided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 9 (according to the invention) The same coating composition as in Example l was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin, 14% by weight of a triethanolammonium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, were used; at the same time the tris(hydroxyethyl) iso-cyanurate was replaced by 3% by weight of dicyandiamide.
The coating was clear and the surface of the panelpro~ided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 10 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin 50, liquid, 8% by weight of a diethanolammonium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, and 7% by weight of a triphenylammonium salt of the ~Rnapsack cleaner component NPS, adjusted to a pH of 7, - ~1371`11 g were used; at the same time the tris(hydroxyethyl) isocyanurate was replaced by 2% by weight of di-cyandiamide.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 11 (according to the in~ention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of æ onium dihydrogen phosphate and 2% by weight of chlorinated paraffin 50, liquid, 8% by weight of a diethanol~onium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, and 7% by weight of a tribenzyl æ onium salt of the ~Rnapsack cleaner component MPS, adjusted to a pH of 7, were used; at the same time the tris(hydroxyethyl) isocyanurate was replaced by 2% by weight of dicyan-diamide.
The coating was clear and the surface of the panel pro~ided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 ga~e the fire resistance class F 30.
Clear, flame-retardant coating compositions are known, for example for wood or plastics, which are based on a binder dissolved in organic solvents and which contain a substantial proportion of chlorinated paraffins (cf.
Bhatnagar and Vergnaud in: "Fire Safety Journal" 4 (3), 163-7 and "Paintindia" 32 (1) 3-6, 14; 1982).
Disadvantages of the known clear, flame-retardant coating compositions are that they give off solvent vapors on drying and contain organically bonded halogen, whereby corrosive and toxic gases are released as the coating compositions break down.
The object of the present invention is therefore to specify clear, expandable coating compositions which possess flame-retardant properties but which break down without releasing halogen-contA;n;ng compounds. This is ~I371Il achieved in accordance with the invention in that the coating compositions contain aqueous synthetic-resin dispersions as builder, and ammonium salts of alkyl phosphates as substance which is carbonized under the effect of heat and/or as ~Yr~n~ion agent and as acid donor.
Furthermore, the coating compositions according to the invention may also, optionally, have compositions in which a) mo~o~lkyl phosphates are present;
b) dialkyl phosphates are present;
c) the salts are hydroxyalkyl-substituted ammonium salts;
d) monoethanolamine is used as hydroxyalkyl-substituted ammonium;
e) diethanolamine is used as hydroxyalkyl-substituted ~mmonium;
f) triethanolamine is used as hydroxyalkyl-substituted ammonium;
0 g) the ~alts are alkyl-substituted ammonium salts;
~137111 h) the alkyl radical has 1 to 6 carbon atoms;
i) the salts are aryl-substituted ammonium salts.
The ammonium salts of alkyl phosphates which are present in the coating compositions according to the invention can be prepared, for example, by the process known from US-A-4,118,443.
In the coating compositions according to the invention it is also possible for mixtures of monoalkyl phosphates and dialkyl phosphates to be present.
The ammonium salts of alkyl phosphates which are present in the coating compositions according to the invention do not only have a flame-retardant action but also give the compositions plasticizing properties. They therefore have a positive effect on the film tear resistance of the flame-retardant coating compositions and can therefore be used as complete substitutes for chlorinated paraffins and other halogen-cont~;ning additives, for example tris(2-chloroethyl) phosphate (TCEP) or tris(2-chloro-isopropyl) phosphate (TCPP).
In the examples below, flame-retardant coating composi-tions are prepared and their effectiveness is determined.
The insulation efficiency of the intumescent paints prepared using these coating compositions was tested in accordance with DIN 4102, part 2 (1977) in a small-scale 213711 ~
test set-up according to DIN 4102, part 8 (1986), while the testing of the surface quality was carried out visually.
Example 1 (Cn~rArative example) The following components were introduced in succession into a stirred vessel fitted with a dissolver disk:
16.8 % by weight of water 3 % by weight of ~Tylose 0.2 % by weight of ~Lopon 890 11 % by weight of A~;um dihydrogen phosphate % by weight of tris(hydroxyethyl) isocyanurate 62 % by weight of ~Maprenal LH 692 2 % by weight of chlorinated paraffin 50, liquid.
Example 2 (Comparative example) The same coating composition as in Example 1 was prepared, but ~Urecoll HM was used instead of ~Maprenal LH 692.
The coating was clear and the surface of the metal panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 3 (Comparative example) The same coating compoæition as in Example 1 was prepared, but without the chlorinated paraffin component.
The coating was clear and the surface of the panel provided with this coating composition was rough and traversed by fine crackæ.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 4 (Comparative example) The same coating composition as in Example 1 was prepared, but 59% by weight of ~Urecoll HM and 4% by weight of ~Rauramin were u~ed instead of 62% by weight of ~Maprenal LH 692.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 met the requirements of the fire resistance class F 30.
Example 5 (Comparative example) The same coating composition as in Example 1 was prepared, but 2% by weight of tris(2-chloroethyl) phos-phate were used instead of 2% by weight of chlorinated paraffin 50, liquid.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 6 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin 50, liquid, 14% by weight of a monoethanol-ammonium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, were used. At the same time the tris(hydroxy-ethyl) isocyanurate was reduced to 4% by weight.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 7 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of - ~;um dihydrogen phosphate and 2% by weight of chlorinated paraffin, 15% by weight of a monoethanol~mmonium salt of the ~Rnapsack cleaner component MPS, adjusted to a pH of 7, were used; at the same time the quantity of tris-(hydroxyethyl) isocyanurate was reduced to 3% by weight.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 8 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin, 15% by weight of a triethanolammonium salt of the ~Knapsack phosphate MDE, adjusted to a pH of 7, were used; at the same time the tris(hydroxyethyl) iso-cyanurate was replaced by 2% by weight of dicyandiamide.
The coating was clear and the surface of the panelprovided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 9 (according to the invention) The same coating composition as in Example l was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin, 14% by weight of a triethanolammonium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, were used; at the same time the tris(hydroxyethyl) iso-cyanurate was replaced by 3% by weight of dicyandiamide.
The coating was clear and the surface of the panelpro~ided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 10 (according to the invention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of ammonium dihydrogen phosphate and 2% by weight of chlorinated paraffin 50, liquid, 8% by weight of a diethanolammonium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, and 7% by weight of a triphenylammonium salt of the ~Rnapsack cleaner component NPS, adjusted to a pH of 7, - ~1371`11 g were used; at the same time the tris(hydroxyethyl) isocyanurate was replaced by 2% by weight of di-cyandiamide.
The coating was clear and the surface of the panel provided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 gave the fire resistance class F 30.
Example 11 (according to the in~ention) The same coating composition as in Example 1 was prepared, but instead of 11% by weight of æ onium dihydrogen phosphate and 2% by weight of chlorinated paraffin 50, liquid, 8% by weight of a diethanol~onium salt of the ~Rnapsack phosphate MDE, adjusted to a pH of 7, and 7% by weight of a tribenzyl æ onium salt of the ~Rnapsack cleaner component MPS, adjusted to a pH of 7, were used; at the same time the tris(hydroxyethyl) isocyanurate was replaced by 2% by weight of dicyan-diamide.
The coating was clear and the surface of the panel pro~ided with this coating composition was smooth and free from cracks.
The fire testing of the coated panel according to DIN 4102 ga~e the fire resistance class F 30.
Claims (10)
1. A clear, expandable, flame-retardant coating compos-ition comprising at least from 10 to 70% by weight of a film-forming binder, from 0 to 40% by weight of at least one substance which is carbonized under the effect of heat, from 0 to 40% by weight of an expansion agent, from 0 to 5% by weight of dispersants and from 0 to 25% by weight of fillers, wherein aqueous synthetic-resin dispersions are present as binder and ammonium salts of alkyl phos-phates are present as substance which is carbonized under the effect of heat and as expansion agent, in a quantity of from 1 to 50% by weight.
2. A coating composition as claimed in claim 1, wherein monoalkyl phosphates are present as alkyl phos-phates.
3. A coating composition as claimed in claim 1, wherein dialkyl phosphates are present as alkyl phosphates.
4. A coating composition as claimed in claim 1, wherein the salts are hydroxyalkyl-substituted ammonium salts.
5. A coating composition as claimed in claim 4, wherein monoethanolamine is used as hydroxyalkyl-substituted ammonium.
6. A coating composition as claimed in claim 4, wherein diethanolamine is used as hydroxyalkyl-substituted ammonium.
7. A coating composition as claimed in claim 4, wherein triethanolamine is used as hydroxyalkyl-substituted ammonium.
8. A coating composition as claimed in claim 1, wherein the salts are alkyl-substituted ammonium salts.
9. A coating composition as claimed in claim 8, wherein the alkyl radical has 1 to 6 carbon atoms.
10. A coating composition as claimed in claim 1, wherein the salts are aryl-substituted ammonium salts.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4343669A DE4343669A1 (en) | 1993-12-21 | 1993-12-21 | Clear, inflatable, flame-retardant coating compounds |
| DEP4343669.2 | 1993-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2137111A1 true CA2137111A1 (en) | 1995-06-22 |
Family
ID=6505660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002137111A Abandoned CA2137111A1 (en) | 1993-12-21 | 1994-12-01 | Clea, expandable, flame-retardant coating compositions |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0659849B1 (en) |
| JP (1) | JPH07252439A (en) |
| AT (1) | ATE170901T1 (en) |
| CA (1) | CA2137111A1 (en) |
| DE (2) | DE4343669A1 (en) |
| ES (1) | ES2122127T3 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19751434A1 (en) * | 1997-11-20 | 1999-07-29 | Clariant Gmbh | Intumescent, flame-retardant coating compounds |
| JP6316138B2 (en) * | 2013-08-08 | 2018-04-25 | 積水化学工業株式会社 | Flame retardant paint composition |
| TW202122516A (en) | 2019-08-30 | 2021-06-16 | 瑞士商克萊瑞特國際股份有限公司 | Intumescent flame-retardant clearcoat formulations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2602289C2 (en) | 1976-01-22 | 1983-11-03 | Hoechst Ag, 6230 Frankfurt | Process for the preparation of acidic phosphoric acid ester salts |
| JPS54113999A (en) * | 1978-02-27 | 1979-09-05 | Goou Kagaku Kougiyou Kk | Fire fighting chemicals |
| US4247435A (en) * | 1978-10-02 | 1981-01-27 | Monsanto Company | Intumescent fire retardant coating compositions |
| DE4023310A1 (en) * | 1990-07-21 | 1992-01-23 | Bayer Ag | INTUMESCENT CARRIERS AND THEIR USE |
-
1993
- 1993-12-21 DE DE4343669A patent/DE4343669A1/en not_active Withdrawn
-
1994
- 1994-11-18 DE DE59406880T patent/DE59406880D1/en not_active Expired - Fee Related
- 1994-11-18 ES ES94118173T patent/ES2122127T3/en not_active Expired - Lifetime
- 1994-11-18 EP EP94118173A patent/EP0659849B1/en not_active Expired - Lifetime
- 1994-11-18 AT AT94118173T patent/ATE170901T1/en not_active IP Right Cessation
- 1994-12-01 CA CA002137111A patent/CA2137111A1/en not_active Abandoned
- 1994-12-20 JP JP6317007A patent/JPH07252439A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0659849B1 (en) | 1998-09-09 |
| EP0659849A3 (en) | 1996-09-18 |
| ES2122127T3 (en) | 1998-12-16 |
| EP0659849A2 (en) | 1995-06-28 |
| DE59406880D1 (en) | 1998-10-15 |
| JPH07252439A (en) | 1995-10-03 |
| DE4343669A1 (en) | 1995-06-22 |
| ATE170901T1 (en) | 1998-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |