GB954086A - Process for the production of modified alkyd resins - Google Patents
Process for the production of modified alkyd resinsInfo
- Publication number
- GB954086A GB954086A GB26783/61A GB2678361A GB954086A GB 954086 A GB954086 A GB 954086A GB 26783/61 A GB26783/61 A GB 26783/61A GB 2678361 A GB2678361 A GB 2678361A GB 954086 A GB954086 A GB 954086A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- acids
- hydroxy
- formaldehyde
- ester
- 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
- 229920000180 alkyd Polymers 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 9
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229940114072 12-hydroxystearic acid Drugs 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 3
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 3
- 239000004593 Epoxy Substances 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- -1 bromates chlorites Chemical class 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000000576 coating method Methods 0.000 abstract 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002596 lactones Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 235000010215 titanium dioxide Nutrition 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000010959 steel Substances 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 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
- C08G63/02—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
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- 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
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Abstract
A process for the production of an alkyd resin comprises reacting a polycarboxylic acid and/or anhydride thereof with an epoxy alkyl ester of an a -mono-alkyl or a , a -dialkyl-alkane mono-carboxylic acid and/or a partial ester of a polyhydroxy compound and an a -monoalkyl or a , a -dialkyl-alkane monocarboxylic acid, which partial ester contains on an average more than one free hydroxyl group per molecule, and in addition with a hydroxy carboxylic acid and/or ester, lactide or lactone thereof, at least one trifunctional or polyfunctional compound being present in the reaction mixture. The hydroxy acids include glycollic, lactic, hydroxy-butyric or valeric, 12-hydroxy stearic, citric, malic and tartaric acids' esters of hydroxy carboxylic acids and glycerol, glycidol and other alcohols, hydrogenated castor oil and monoglycerides. The monocarboxylic acids containing a tertiary or quaternary carbon atom can be those produced by the processes of Specifications 871,278 and 873,738. Catalysts for the esterification are sulphuric, phosphoric and sulphonic acids, halides of boron, magnesium, zinc or aluminium, alkali metal hydroxides, amines, quaternary ammonium complexes and BF3 complexes. Colour and colour stability can be improved by treating the products with an oxidising agent the standard potential of which is at least 0.6 volt e.g. nitric acid, chlorates, bromates chlorites, hypochlorites, chromates, permanganates, chlorine, bromine, hydrogen peroxide and ozone. The products can be used in paints, lacquers and varnishes, with pigments, phenol, formaldehyde resins, urea-formaldehyde resins melamine-formaldehyde resins and thickeners. In examples the C9-11 acid used is obtained from a mixture of C8-10 alkenes, (unbranched, branched, and cyclic), and has an equivalent weight of 151.5 and contains 90% of acids in which the carboxyl group is attached to a quaternary carbon atom and 10% in which it is attached to a tertiary atom. Reacted together are (1) and (2) phthalic anhydride, glycerol, glycidyl esters of C9 to C11 monocarboxylic acids and 12-hydroxystearic acid, in xylene; (4) a similar mixture in which, however, glycollic acid replaces the 12-hydroxystearic acid and the product is heated with hydrogen peroxide. The resin of (1) is mixed with urea formaldehyde resin and titanium white to give a stoving enamel. Specifications 936,808, 942,465 and 946,432 also are referred to.ALSO:A process for covering articles with protective or decorative coatings is characterized in that for this purpose there are used alkyd resins obtained by reacting a polycarboxylic acid and/or anhydride thereof with an epoxy alkyl ester of an a -monoalkyl or a -dialkyl-alkane monocarboxylic acid and/or partial ester of a polyhydroxy compound and an a -mono alkyl or a ,a -dialkyl-alkane monocarboxylic acid, which partial ester contains on an average more than one free hydroxyl group per molecule, and in addition with a hydroxycarboxylic acid and/or ester, lactide or lactone thereof, at least one trifunctional or polyfunctional compound being present in the reaction mixture. Suitable components for the alkyds are specified (see Division C3). Pigments, diluents, phenol-formaldehyde, urea-formaldehyde and melamine-formaldehyde resins may also be added to the coatings. In an example (1) an alkyd prepared from phthalic anhydride, glycerol, glycidyl esters of C9 to C11 monocarboxylic acids branched at the alpha position and 12-hydroxy-stearic acid by heating in xylene is mixed with urea-formaldehyde resin and titanium white, applied to thin steel panels and baked at 150 DEG C. Specifications 871,278, 873,738, 936,808, 942,465 and 946,432 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL254156A NL128222C (en) | 1960-07-25 | 1960-07-25 | Method for preparing modified alkyd resins |
| NL260607A NL260607A (en) | 1960-07-25 | 1961-01-30 | Method for improving the colour of alkyd resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB954086A true GB954086A (en) | 1964-04-02 |
Family
ID=29714411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26783/61A Expired GB954086A (en) | 1960-07-25 | 1961-07-24 | Process for the production of modified alkyd resins |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE606449A (en) |
| FR (1) | FR1295843A (en) |
| GB (1) | GB954086A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013169702A1 (en) * | 2012-05-09 | 2013-11-14 | Ppg Industries Ohio, Inc. | Basecoat with improved adhesion to bioplastic |
| US10617617B1 (en) | 2018-12-04 | 2020-04-14 | Momentive Performance Materials Inc. | Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| WO2020117516A1 (en) | 2018-12-04 | 2020-06-11 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrous amino acid based substrates, especially hair |
| US11179312B2 (en) | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1408141A (en) * | 1971-12-09 | 1975-10-01 | Laporte Ind | Polymeric compositions |
-
1961
- 1961-07-24 FR FR868807A patent/FR1295843A/en not_active Expired
- 1961-07-24 GB GB26783/61A patent/GB954086A/en not_active Expired
- 1961-07-24 BE BE606449A patent/BE606449A/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013169702A1 (en) * | 2012-05-09 | 2013-11-14 | Ppg Industries Ohio, Inc. | Basecoat with improved adhesion to bioplastic |
| US11179312B2 (en) | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
| US10617617B1 (en) | 2018-12-04 | 2020-04-14 | Momentive Performance Materials Inc. | Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| WO2020117516A1 (en) | 2018-12-04 | 2020-06-11 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrous amino acid based substrates, especially hair |
| WO2020117509A1 (en) | 2018-12-04 | 2020-06-11 | Momentive Performance Materials Inc. | Polycarboxylic acid compounds for the treatment of fibrous amino acid based substrates, especially hair |
| US11090255B2 (en) | 2018-12-04 | 2021-08-17 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1295843A (en) | 1962-06-08 |
| BE606449A (en) | 1962-01-24 |
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