CA1056549A - Process for the production of flame-resistant phenolic resin foam plastics - Google Patents
Process for the production of flame-resistant phenolic resin foam plasticsInfo
- Publication number
- CA1056549A CA1056549A CA221,595A CA221595A CA1056549A CA 1056549 A CA1056549 A CA 1056549A CA 221595 A CA221595 A CA 221595A CA 1056549 A CA1056549 A CA 1056549A
- Authority
- CA
- Canada
- Prior art keywords
- percent
- volume
- acid
- curing agent
- mixture
- 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.)
- Expired
Links
- 239000006260 foam Substances 0.000 title claims abstract description 45
- 239000004033 plastic Substances 0.000 title claims abstract description 28
- 229920003023 plastic Polymers 0.000 title claims abstract description 28
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229920001568 phenolic resin Polymers 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 21
- 239000005011 phenolic resin Substances 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 53
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 34
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 18
- 230000002378 acidificating effect Effects 0.000 claims abstract description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 28
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 238000005187 foaming Methods 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 229960004279 formaldehyde Drugs 0.000 claims description 10
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 claims description 9
- 235000019256 formaldehyde Nutrition 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 229940044654 phenolsulfonic acid Drugs 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- -1 aromatic sulfonic acids Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- NGZXDRGWBULKFA-NSOVKSMOSA-N (+)-Bebeerine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 NGZXDRGWBULKFA-NSOVKSMOSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003340 retarding agent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- BBGJFAYGMNGEIW-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[4-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]piperazin-1-yl]methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2CCN(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)CC2)=C1 BBGJFAYGMNGEIW-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-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
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- OASOQJKCZXXDMI-UHFFFAOYSA-N ethane-1,2-diol;hydrochloride Chemical compound Cl.OCCO OASOQJKCZXXDMI-UHFFFAOYSA-N 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0095—Mixtures of at least two compounding ingredients belonging to different one-dot groups
-
- 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
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/011—Crosslinking or vulcanising agents, e.g. accelerators
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/907—Nonurethane flameproofed cellular product
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742413567 DE2413567C3 (de) | 1974-03-21 | Verfahren zur Herstellung von flammfesten Phenolharz-Schaumstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1056549A true CA1056549A (en) | 1979-06-12 |
Family
ID=5910718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,595A Expired CA1056549A (en) | 1974-03-21 | 1975-03-07 | Process for the production of flame-resistant phenolic resin foam plastics |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4001148A (enExample) |
| JP (1) | JPS50127962A (enExample) |
| BE (1) | BE826931A (enExample) |
| CA (1) | CA1056549A (enExample) |
| FR (1) | FR2264838B1 (enExample) |
| GB (1) | GB1457241A (enExample) |
| IT (1) | IT1034153B (enExample) |
| NL (1) | NL7503097A (enExample) |
| NO (1) | NO143628C (enExample) |
| SE (1) | SE404532B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4219623A (en) * | 1977-07-26 | 1980-08-26 | Reichhold Limited | Phenol formaldehyde resin foams |
| US4176106A (en) * | 1977-07-28 | 1979-11-27 | Union Carbide Corporation | Phenol/formaldehyde resoles and cellular products derived therefrom |
| US4176216A (en) * | 1977-07-28 | 1979-11-27 | Union Carbide Corporation | Cellular products derived from phenol/formaldehyde resoles |
| CA1150450A (en) * | 1978-09-14 | 1983-07-19 | Company 'a' (Foam) Limited | Foamed plastics materials |
| US4202945A (en) * | 1979-04-03 | 1980-05-13 | Leinhardt Franklyn J | Phenolic foam materials and method of making same |
| US4478958A (en) * | 1981-07-10 | 1984-10-23 | Kopper Company, Inc. | Method for preparing phenolic foams using anhydrous aryl sulfonic acid catalysts |
| US4444912A (en) * | 1981-07-10 | 1984-04-24 | Koppers Company, Inc. | Phenolic foam and composition and method for preparing the same |
| US4429075A (en) * | 1982-05-17 | 1984-01-31 | Chem-Nuclear Systems, Inc. | Cross-linked urea-formaldehyde polymer matrix compositions containing cyclic intermediate structures |
| US4539338A (en) * | 1982-07-09 | 1985-09-03 | Koppers Company, Inc. | Phenol formaldehyde resoles for making phenolic foam |
| CA1238149A (en) * | 1984-10-30 | 1988-06-14 | Jacynthe Cote | Closed cell phenolic foams |
| JPH01201341A (ja) * | 1988-02-06 | 1989-08-14 | Showa Highpolymer Co Ltd | レゾール型フェノール樹脂発泡体の製造方法 |
| CA3093201C (en) * | 2018-03-06 | 2023-08-22 | Hexion Inc. | Catalyst system for curing phenolic resole resins |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772246A (en) * | 1952-08-06 | 1956-11-27 | Lockheed Aircraft Corp | Cellular phenol aldehyde plastic resins |
| US2728741A (en) * | 1952-11-01 | 1955-12-27 | Lockheed Aircraft Corp | Phenol-formaldehyde resins for foaming compositions |
| DE2058663B2 (de) * | 1970-11-28 | 1975-08-28 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Phenolharzschaumstoffen |
| US3779955A (en) * | 1972-01-31 | 1973-12-18 | Resitron Corp | Non-burning resinous compounds and structures prepared from furan resins |
-
1975
- 1975-03-03 US US05/554,899 patent/US4001148A/en not_active Expired - Lifetime
- 1975-03-07 CA CA221,595A patent/CA1056549A/en not_active Expired
- 1975-03-11 IT IT21114/75A patent/IT1034153B/it active
- 1975-03-12 NO NO750831A patent/NO143628C/no unknown
- 1975-03-13 JP JP50030637A patent/JPS50127962A/ja active Pending
- 1975-03-14 NL NL7503097A patent/NL7503097A/xx not_active Application Discontinuation
- 1975-03-17 GB GB1104475A patent/GB1457241A/en not_active Expired
- 1975-03-19 SE SE7503163A patent/SE404532B/xx unknown
- 1975-03-20 FR FR7508795A patent/FR2264838B1/fr not_active Expired
- 1975-03-20 BE BE154544A patent/BE826931A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO750831L (enExample) | 1975-09-23 |
| SE7503163L (enExample) | 1975-09-22 |
| NO143628B (no) | 1980-12-08 |
| FR2264838A1 (enExample) | 1975-10-17 |
| NL7503097A (nl) | 1975-09-23 |
| NO143628C (no) | 1981-03-18 |
| JPS50127962A (enExample) | 1975-10-08 |
| GB1457241A (en) | 1976-12-01 |
| IT1034153B (it) | 1979-09-10 |
| DE2413567A1 (de) | 1975-10-02 |
| BE826931A (fr) | 1975-09-22 |
| US4001148A (en) | 1977-01-04 |
| SE404532B (sv) | 1978-10-09 |
| FR2264838B1 (enExample) | 1979-08-03 |
| DE2413567B2 (de) | 1976-02-05 |
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