GB1529567A - Reinforced plastics material based on phenol-aldehyde resins - Google Patents
Reinforced plastics material based on phenol-aldehyde resinsInfo
- Publication number
- GB1529567A GB1529567A GB47192/74A GB4719274A GB1529567A GB 1529567 A GB1529567 A GB 1529567A GB 47192/74 A GB47192/74 A GB 47192/74A GB 4719274 A GB4719274 A GB 4719274A GB 1529567 A GB1529567 A GB 1529567A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- hcho
- catalyst
- novolac
- resole
- 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
- 229920005989 resin Polymers 0.000 title abstract 5
- 239000011347 resin Substances 0.000 title abstract 5
- 239000002990 reinforced plastic Substances 0.000 title abstract 3
- 239000000463 material Substances 0.000 title 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 11
- 239000003054 catalyst Substances 0.000 abstract 8
- 229920003987 resole Polymers 0.000 abstract 8
- -1 methylol group Chemical group 0.000 abstract 6
- 229920003986 novolac Polymers 0.000 abstract 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 5
- 239000004202 carbamide Substances 0.000 abstract 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 3
- 239000011342 resin composition Substances 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000003365 glass fiber Substances 0.000 abstract 2
- 150000004324 hydroxyarenes Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 2
- 239000003495 polar organic solvent Substances 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 1
- 125000001477 organic nitrogen group Chemical group 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000005011 phenolic resin Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/248—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using pre-treated fibres
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
1529567 Reinforced phenolic resins UNILEVER Ltd 30 Oct 1975 [31 Oct 1974] 47192/74 Heading C3R [Also in Division D1] Reinforced plastics comprise a fibrous base, e.g. paper, glass or textile fibres, and a cured phenol-aldehyde or phenol-ketone resin composition obtained by curing a liquid resole resin with a hydroxy arene sulphonic acid catalyst in the presence of an oxygen-containing polar organic solvent. The amount of fibrous base with respect to the dry weight of the resole and catalyst generally varies from 10- 60% wt. In an embodiment a phenol-aldehyde or phenol-ketone resin composition suitable for manufacturing reinforced plastics comprises a liquid resole resin, a hydroxy arene sulphonic acid catalyst and an organic polar solvent which is an alcohol in which any hydroxyl group is a methylol group. The oxygen-containing polar organic solvent may be inert, e.g. an alcohol, ester or nitroalkane or reactive with respect to the activated hydrogen atoms of the resole, e.g. alcohols containing a methylol group attached to a ring structure, e.g. furfuryl alcohol, benzyl alcohol and salicyl alcohol; aldehydes and ketones. The resoles are obtained by reacting an excess of an aldehyde or ketone, preferably formaldehyde, with a phenolic compound, preferably phenol in the presence of an alkaline catalyst. The catalyst may comprise one or more aromatic rings and may be a sulphonated dihydroxy diphenyl alkane, a nucleus sulphonated phenol-HCHO novolac or such novolac modified with a nitrogen containing organic compound such as urea, thiourea, dicyandiamide or melamine. The novolac catalysts may be prepared either by reacting phenol with H 2 SO 4 or chlorosulphonic acid and then with the optional nitrogencontaining organic compound and aqueous HCHO, or by sulphonating an optionally nitrogen-modified phenol-HCHO novolac or by partially sulphonating phenol before condensation with HCHO and the optional nitrogencontaining organic compound, followed by further sulphonation with H 2 SO 4 . The pot life of the resin composition can be increased by the incorporation of an organic nitrogen base such as an amine, amide or nitrile, e.g. alkylamines, melamine, aniline, acetamide, urea or acrylonitrile, either in the free form, or in the co-condensed form in the catalyst, or in the form of a sulphonic acid salt. The amount of catalyst generally ranges from 1-100 p.b.w. per 100 p.b.w. of resole. The impregnated fibrous base may be cured at ambient temperature and atmospheric pressure, or at elevated temperature and under pressure. In the examples any one of the following liquid catalysts:- (1) a sulphonated phenol/urea/ HCHO novolac alone and in admixture with either (i) glycerol, or (ii) glycerol and urea; (2) a sulphonated phenol/HCHO novolac in admixture with either (i) glycerol or (ii) glycerol and urea is mixed with a liquid phenol.HCHO resole resin alone or in admixture with either (i) benzyl alcohol, (ii) acetone or (iii) furfuraldehyde and used to impregnate glass fibre mats which are cured either under ambient conditions or at elevated temperature and under pressure. In other examples glass fibre rovings, the resole resin and the catalyst are pulverized simultaneously and then cured.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47192/74A GB1529567A (en) | 1974-10-31 | 1974-10-31 | Reinforced plastics material based on phenol-aldehyde resins |
| DE19752548476 DE2548476A1 (en) | 1974-10-31 | 1975-10-29 | REINFORCED PLASTIC MATERIAL |
| FR7533096A FR2289567A1 (en) | 1974-10-31 | 1975-10-29 | REINFORCED PLASTIC MATERIAL CONSISTING OF A FIBROUS MATERIAL IMPREGNATED WITH A CROSS-LINKED PHENOL / ALDEHYDE RESIN |
| DK488875A DK488875A (en) | 1974-10-31 | 1975-10-30 | REINFORCED PLASTIC MATERIAL AND PHENOLALDEHYDE RESIN USE, AND PROCEDURE FOR ITM |
| BE161514A BE835166A (en) | 1974-10-31 | 1975-10-31 | REINFORCED PLASTIC MATERIAL |
| NL7512829A NL7512829A (en) | 1974-10-31 | 1975-10-31 | METHOD FOR PREPARING PENOL RESINS. |
| LU73698A LU73698A1 (en) | 1974-10-31 | 1975-10-31 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47192/74A GB1529567A (en) | 1974-10-31 | 1974-10-31 | Reinforced plastics material based on phenol-aldehyde resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1529567A true GB1529567A (en) | 1978-10-25 |
Family
ID=10444086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47192/74A Expired GB1529567A (en) | 1974-10-31 | 1974-10-31 | Reinforced plastics material based on phenol-aldehyde resins |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE835166A (en) |
| DE (1) | DE2548476A1 (en) |
| DK (1) | DK488875A (en) |
| FR (1) | FR2289567A1 (en) |
| GB (1) | GB1529567A (en) |
| LU (1) | LU73698A1 (en) |
| NL (1) | NL7512829A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2283764A (en) * | 1993-11-09 | 1995-05-17 | Tba Composites Limited | Resin and carbon fibre moulding material |
| RU2321605C1 (en) * | 2006-10-09 | 2008-04-10 | Федеральное государственное унитарное предприятие "Обнинское научно-производственное предприятие "Технология" | Method of manufacture of articles from glass-reinforced plastics |
| JP2011074218A (en) * | 2009-09-30 | 2011-04-14 | Dic Corp | Method for producing phenol resin |
| WO2014073557A1 (en) * | 2012-11-12 | 2014-05-15 | Dic株式会社 | Phenolic-hydroxyl-containing resin, epoxy resin, curable resin composition, substance obtained by curing same, and semiconductor sealant |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3346153C2 (en) * | 1983-12-21 | 1994-04-07 | Deutsche Texaco Ag, 2000 Hamburg | Process for the production of modified phenolic resin wood binders and their application in the production of particle boards |
-
1974
- 1974-10-31 GB GB47192/74A patent/GB1529567A/en not_active Expired
-
1975
- 1975-10-29 DE DE19752548476 patent/DE2548476A1/en active Pending
- 1975-10-29 FR FR7533096A patent/FR2289567A1/en active Granted
- 1975-10-30 DK DK488875A patent/DK488875A/en unknown
- 1975-10-31 BE BE161514A patent/BE835166A/en not_active IP Right Cessation
- 1975-10-31 LU LU73698A patent/LU73698A1/xx unknown
- 1975-10-31 NL NL7512829A patent/NL7512829A/en not_active Application Discontinuation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2283764A (en) * | 1993-11-09 | 1995-05-17 | Tba Composites Limited | Resin and carbon fibre moulding material |
| RU2321605C1 (en) * | 2006-10-09 | 2008-04-10 | Федеральное государственное унитарное предприятие "Обнинское научно-производственное предприятие "Технология" | Method of manufacture of articles from glass-reinforced plastics |
| JP2011074218A (en) * | 2009-09-30 | 2011-04-14 | Dic Corp | Method for producing phenol resin |
| WO2014073557A1 (en) * | 2012-11-12 | 2014-05-15 | Dic株式会社 | Phenolic-hydroxyl-containing resin, epoxy resin, curable resin composition, substance obtained by curing same, and semiconductor sealant |
| CN104822722A (en) * | 2012-11-12 | 2015-08-05 | Dic株式会社 | Phenolic-hydroxyl-containing resin, epoxy resin, curable resin composition, substance obtained by curing same, and semiconductor sealant |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7512829A (en) | 1976-05-04 |
| DK488875A (en) | 1976-05-01 |
| FR2289567A1 (en) | 1976-05-28 |
| FR2289567B1 (en) | 1981-08-21 |
| DE2548476A1 (en) | 1976-05-06 |
| LU73698A1 (en) | 1976-08-13 |
| BE835166A (en) | 1976-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921030 |