GB823224A - Improvements in and relating to the preparation of polyesters - Google Patents
Improvements in and relating to the preparation of polyestersInfo
- Publication number
- GB823224A GB823224A GB2387/56A GB238756A GB823224A GB 823224 A GB823224 A GB 823224A GB 2387/56 A GB2387/56 A GB 2387/56A GB 238756 A GB238756 A GB 238756A GB 823224 A GB823224 A GB 823224A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- polyester
- dienophilic
- diol
- polyesters
- 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
- 229920000728 polyester Polymers 0.000 title abstract 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001993 dienes Chemical class 0.000 abstract 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- -1 maleic or fumaric Chemical class 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 abstract 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 abstract 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 229920000178 Acrylic resin Polymers 0.000 abstract 1
- 239000004925 Acrylic resin Substances 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 238000007259 addition reaction Methods 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- ZVSONHCDFQDFNN-UHFFFAOYSA-N hexa-1,3-dien-1-ol Chemical class CCC=CC=CO ZVSONHCDFQDFNN-UHFFFAOYSA-N 0.000 abstract 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229920001169 thermoplastic Polymers 0.000 abstract 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/918—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Thermoplastic polyesters containing D 4-tetrahydrophthalic acid groups of the formula <FORM:0823224/IV (a)/1> where R1-6 are any of H, alkyl, aryl, or acyl, or OH and esters thereof, R1 or R2 may form endo(m)ethylene bridges with R5 or R6, and R7-8 are H or lower alkyl groups, the polyester having more than 10 ester groups in the molecule and an M.W. of at least 2000, are prepared by subjecting a linear polyester containing dienophilic groups to a dienic addition reaction with a compound having a single system of conjugated double bonds. This reaction is preferably performed at 0-120 DEG C. in the presence of an inhibitor such as 1,2-dinitrobenzene or hydroquinone, and the conjugated diene may be used in an equivalent or less than equivalent amount with respect to the dienophilic groups in the polyester. The polyesters may be derived from butene dioic acids such as maleic or fumaric, with or without such saturated acids as succinic, glutaric, adipic, sebacic, tartaric, acetonedicarboxylic, 3-ketopimelic, or terephthalic and from diols such as hexane diol (1,6), butane diol (1,4), butylene glycol, butene diol and diethylene glycol, with or without such monohydric alcohols as octanol. Conjugated dienes specified are butadiene, cyclopentadiene, cyclohexadiene, and 2-ethyl, 1,3-hexadien-1-ol esters (e.g. acetate). The resultant polymers may be dissolved in chlorobenzene, mixed with unspecified vinyl or acrylic resins or with cellulosic derivatives, or may have their D 4 unsaturation epoxidized, halogenated, hydrogenated or hydrohalogenated. Addition polymers.-In the case when the conjugated diene is used in less than the equivalent amount with respect to the dienophilic groups in the polyester, the remaining ethylenically unsaturated groups may be copolymerized with styrene in the presence of methyl ethyl ketone peroxide and either cobalt naphthenate or dimethyl aniline.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER0015895 | 1955-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823224A true GB823224A (en) | 1959-11-11 |
Family
ID=6745647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2387/56A Expired GB823224A (en) | 1955-01-29 | 1956-01-24 | Improvements in and relating to the preparation of polyesters |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1178211B (en) |
| GB (1) | GB823224A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3333022A (en) * | 1963-10-30 | 1967-07-25 | Albert Ag Chem Werke | Flame retardant resins prepared from unsaturated polyesters and dicyclopentadiene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1860730A (en) * | 1930-06-16 | 1932-05-31 | Benjamin T Brooks | Organic acid-polyhydric alcohol resins |
| DE943495C (en) * | 1951-03-15 | 1956-05-24 | Philips Nv | Process for the production of plastics as such or as fillers or coating compounds for electrical insulation |
-
1955
- 1955-01-29 DE DER15895A patent/DE1178211B/en active Pending
-
1956
- 1956-01-24 GB GB2387/56A patent/GB823224A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3333022A (en) * | 1963-10-30 | 1967-07-25 | Albert Ag Chem Werke | Flame retardant resins prepared from unsaturated polyesters and dicyclopentadiene |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1178211B (en) | 1964-09-17 |
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