GB540167A - Improvement in insoluble polymers and processes of producing same - Google Patents
Improvement in insoluble polymers and processes of producing sameInfo
- Publication number
- GB540167A GB540167A GB32999/39A GB3299939A GB540167A GB 540167 A GB540167 A GB 540167A GB 32999/39 A GB32999/39 A GB 32999/39A GB 3299939 A GB3299939 A GB 3299939A GB 540167 A GB540167 A GB 540167A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compositions
- heated
- vinyl acetate
- mixture
- resin
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 229920000642 polymer Polymers 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 12
- 239000011347 resin Substances 0.000 abstract 6
- 229920005989 resin Polymers 0.000 abstract 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 4
- -1 ethylene compound Chemical class 0.000 abstract 4
- 239000005977 Ethylene Substances 0.000 abstract 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 3
- 238000006116 polymerization reaction Methods 0.000 abstract 3
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 239000001263 FEMA 3042 Substances 0.000 abstract 2
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 abstract 2
- 229960005070 ascorbic acid Drugs 0.000 abstract 2
- 235000010323 ascorbic acid Nutrition 0.000 abstract 2
- 239000011668 ascorbic acid Substances 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- 230000002028 premature Effects 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 abstract 2
- 229940033123 tannic acid Drugs 0.000 abstract 2
- 235000015523 tannic acid Nutrition 0.000 abstract 2
- 229920002258 tannic acid Polymers 0.000 abstract 2
- PVLVQTYSRICFCB-ODZAUARKSA-N (z)-but-2-enedioic acid;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.OC(=O)\C=C/C(O)=O PVLVQTYSRICFCB-ODZAUARKSA-N 0.000 abstract 1
- MKEPGIQTWYTRIW-ODZAUARKSA-N (z)-but-2-enedioic acid;ethane-1,2-diol Chemical compound OCCO.OC(=O)\C=C/C(O)=O MKEPGIQTWYTRIW-ODZAUARKSA-N 0.000 abstract 1
- HTKIMDWJJMPDFE-UHFFFAOYSA-N C(C)(=O)OC=C.C(C=C/C(=O)O)(=O)O.C(C(C)O)O Chemical compound C(C)(=O)OC=C.C(C=C/C(=O)O)(=O)O.C(C(C)O)O HTKIMDWJJMPDFE-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000001879 gelation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 150000008442 polyphenolic compounds Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 229920001864 tannin Polymers 0.000 abstract 1
- 235000018553 tannin Nutrition 0.000 abstract 1
- 239000001648 tannin 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
- C08K5/0008—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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
540,167. Synthetic resinous compositions. AMERICAN CYANAMID CO. Dec. 28, 1939, No. 32999. Convention date, Dec. 30, 1938. [Class 2 (iii)] In process of producing resinous compositions comprising a polyhydric alcohol polyester of an olefine a, #-dicarboxylic acid and a miscible polymerizable α-substituted ethylene compound containing the group CH 2 =C<, premature polymerization of the composition is prevented by the incorporation of a phenol, particularly a di- or polyhydroxy phenol, an aromatic amine, particularly symmetrical a, #-naphthyl p-phenylene diamine, tannin, laevo ascorbic acid, benzaldehyde or α-naphthol. Polymerization of the compositions to infusible insoluble resins is effected by heat and/or lighc, with or without pressure, in the presence of a polymerization catalyst ; when heat is employed, the composition is heated to a temperature of 70‹-100‹C., so that it becomes on the verge of gelation, before the addition of the catalyst, and, to prevent a too rapid rise in viscosity, the ethylene compound may be added in stages. In examples, (1) a mixture of diethylene glycol maleate resin is heated with vinyl acetate, and resorcinol, symmetrical α, #-naphthyl p-phenylene diamine, or hydroquinone is either incorporated in the resin during its preparation or is added to the mixture before or after heating ; (2) and (5) a mixture of ethylene glycol maleate resin, vinyl acetate and benzoyl peroxide is added to tannic acid and allowed to stand at room temperature or is heated with tannic acid, hydroquinone or α-naphthol; (3) and (4) a mixture of propylene glycol maleate vinyl acetate and benzoyl peroxide is heated with laevo ascorbic acid or benzaldehyde. Specifications 497,175, 540,168 and 540,169 are referred to. According to the Specification as open to inspection under Sect. 91, (1) sulphur compounds may be used to prevent premature polymerization, (2) when styrene is an ingredient of the composition, the resin is derived from a glycol which if straight-chained contains at least 8 carbon atoms and if branch-chained at least 5 carbon atoms ; examples of such resins are specified; (3) examples are given of compositions in which the ethylene compound is styrene or vinyl acetate, some of which compositions do not contain an inhibitor. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US540167XA | 1938-12-30 | 1938-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB540167A true GB540167A (en) | 1941-10-08 |
Family
ID=21988202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32999/39A Expired GB540167A (en) | 1938-12-30 | 1939-12-28 | Improvement in insoluble polymers and processes of producing same |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE474835A (en) |
| CA (1) | CA456692A (en) |
| FR (1) | FR949717A (en) |
| GB (1) | GB540167A (en) |
| IT (1) | IT432313A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2452669A (en) * | 1945-02-08 | 1948-11-02 | Cornell Aeronautical Labor Inc | Copolymerization of polyesters and vinyl compounds |
| US2505039A (en) * | 1947-04-05 | 1950-04-25 | Hercules Powder Co Ltd | Cellulose derivative plastic composition |
| US2514688A (en) * | 1948-02-03 | 1950-07-11 | Shell Dev | Stabilization of 3, 4-dihydro-1, 2-pyran-2-carboxaldehyde |
| US2558047A (en) * | 1947-04-05 | 1951-06-26 | Hercules Powder Co Ltd | Cellulose derivative plastic composition |
| US2593787A (en) * | 1951-03-30 | 1952-04-22 | Pittsburgh Plate Glass Co | Stabilization of polymerizable unsaturated dicarboxylic acid polyesters and mixtures thereof withvinylic monomers |
| US2627510A (en) * | 1948-01-19 | 1953-02-03 | Pittsburgh Plate Glass Co | Inhibition of gelation of polymerizable mixtures |
| US2643985A (en) * | 1951-04-21 | 1953-06-30 | Pittsburgh Plate Glass Co | Stabilizing polyester materials with phenyl substituted catechols |
| US2646416A (en) * | 1950-10-20 | 1953-07-21 | Pittsburgh Plate Glass Co | Inhibition of gelation in unsaturated polyesters with salts of amines |
| US4352900A (en) | 1980-12-31 | 1982-10-05 | Mobil Oil Corporation | Stabilized thermosetting polyester |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1269619A (en) * | 1960-05-09 | 1961-08-18 | Rhone Poulenc Sa | New process for preparing polystyrene-polyester composite panels |
-
0
- BE BE474835D patent/BE474835A/xx unknown
- CA CA456692A patent/CA456692A/en not_active Expired
- IT IT432313D patent/IT432313A/it unknown
-
1939
- 1939-12-28 GB GB32999/39A patent/GB540167A/en not_active Expired
-
1947
- 1947-07-09 FR FR949717D patent/FR949717A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2452669A (en) * | 1945-02-08 | 1948-11-02 | Cornell Aeronautical Labor Inc | Copolymerization of polyesters and vinyl compounds |
| US2505039A (en) * | 1947-04-05 | 1950-04-25 | Hercules Powder Co Ltd | Cellulose derivative plastic composition |
| US2558047A (en) * | 1947-04-05 | 1951-06-26 | Hercules Powder Co Ltd | Cellulose derivative plastic composition |
| US2627510A (en) * | 1948-01-19 | 1953-02-03 | Pittsburgh Plate Glass Co | Inhibition of gelation of polymerizable mixtures |
| US2514688A (en) * | 1948-02-03 | 1950-07-11 | Shell Dev | Stabilization of 3, 4-dihydro-1, 2-pyran-2-carboxaldehyde |
| US2646416A (en) * | 1950-10-20 | 1953-07-21 | Pittsburgh Plate Glass Co | Inhibition of gelation in unsaturated polyesters with salts of amines |
| US2593787A (en) * | 1951-03-30 | 1952-04-22 | Pittsburgh Plate Glass Co | Stabilization of polymerizable unsaturated dicarboxylic acid polyesters and mixtures thereof withvinylic monomers |
| US2643985A (en) * | 1951-04-21 | 1953-06-30 | Pittsburgh Plate Glass Co | Stabilizing polyester materials with phenyl substituted catechols |
| US4352900A (en) | 1980-12-31 | 1982-10-05 | Mobil Oil Corporation | Stabilized thermosetting polyester |
Also Published As
| Publication number | Publication date |
|---|---|
| IT432313A (en) | |
| BE474835A (en) | |
| FR949717A (en) | 1949-09-07 |
| CA456692A (en) | 1949-05-17 |
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