GB884660A - Pentaerythritol and polypentaerithritol esters and chlorinated polymers containing them - Google Patents

Pentaerythritol and polypentaerithritol esters and chlorinated polymers containing them

Info

Publication number
GB884660A
GB884660A GB10882/58A GB1088258A GB884660A GB 884660 A GB884660 A GB 884660A GB 10882/58 A GB10882/58 A GB 10882/58A GB 1088258 A GB1088258 A GB 1088258A GB 884660 A GB884660 A GB 884660A
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United Kingdom
Prior art keywords
esters
ester
groups
average
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
Application number
GB10882/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB884660A publication Critical patent/GB884660A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/10Esters; Ether-esters
    • C08K5/101Esters; Ether-esters of monocarboxylic acids
    • C08K5/103Esters; Ether-esters of monocarboxylic acids with polyalcohols

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyethers (AREA)

Abstract

Chlorine-containing polymers of one or more monomers containing a single CH2 = C< group are plasticized by an ester of the general formula <FORM:0884660/IV (a)/1> wherein the R groups, which may be the same or different, represent hydrocarbon groups which are free of aliphatic and cycloaliphatic unsaturation and are such that the RCO- groups each contain 5-7, or an average of 5 to about 7,5 carbon atoms and x represents an integer from 1 to 3, the ester having a melting point not exceeding about 35 DEG C., and having an H number in the range of 8 to 16,5 or an average H number in the range 8 to 25,5, or are plasticized by a mixture of esters, each of the above general formula wherein the R groups represent the same or different hydrocarbon groups free from aliphatic and cycloaliphatic unsaturation and x represents an integer from 1 to 14, the mixture of esters being such that its melting point is not above about 35 DEG C., the H number is from 8 to 16,5 or the average H number is from 8 to 25,5, the RCO- groups therein each contain 5 to 7, or an average of 5 to 7,5, carbon atoms and the value of x in each ester molecule is an integer of 1 to 3 or the average value of x in the mixture is from 1 to 3. The H number of a carboxylic acid is computed by summing prescribed values allotted to the number and character of the carbon atoms a -, b - and g - to the carboxylic group and to the number and position of any aromatic rings present. H numbers are given for numerous carboxylic acids whose acyl groups may be present singly or in admixture in the esters or ester mixtures, including straight and branched chain alkanoic, cycloalkanoic, cycloalkylalkanoic, alkylcycloalkanoic, aromatic, aralkanoic and alkylaromatic acids; typical acids and their H numbers are acetic 0, benzoic 1, n-hexanoic 65, a -methylbutyric 10, triphenylacetic 13,5 and tri(t-butyl)acetic 37,5. Many examples are given of simple, mixed and mixtures of esters including dipentaerythritol hexa (a -ethylbutyrate), pentaerythritol tetra(a -ethyl-methylbutyrate) and tripentaerythritol tetra(diisopropylacetate)-tri(acetate)-myristate. The esters preferably have a purity corresponding to an acid number below 2 and a hydroxyl number below 15. Specified polymers are polyvinyl chloride and copolymers of vinyl chloride with vinylidene chloride or a vinyl ester of a lower aliphatic acid such as acetic or propionic acid. The esters may be used with other plasticizers such as a phthalate ester or a conventional dipentaerythritol ester. There may also be present anti-oxidants such as phosphites, amines and phenols, pigments, clay fillers, lubricants and polymer stabilizers such as complex lead silicatelead sulphate salt. The plasticized polymers may be used as electrical insulators of improved stability. The preparation of the esters is described (see Group IV(b)).ALSO:The invention comprises esters of the general formula <FORM:0884660/IV (b)/1> wherein the R groups, which may be the same or different, represent hydrocarbon groups which are free of aliphatic and cycloaliphatic unsaturation and are such that the RCO-groups each contain 5-7, or an average of 5 to about 7.5, carbon atoms and x represents an integer from 1 to 3, the ester having a melting point not exceeding about 35 DEG C., and having an H number in the range 8 to 16.5 or an average H number in the range 8 to 25.5. The invention also comprises a mixture of esters each of the above general formula wherein the R groups represent the same or different hydrocarbon groups free from aliphatic and cycloaliphatic unsaturation and x represents an integer from 1 to 14, the mixture of esters being such that its melting point is not above about 35 DEG C., the H number is from 8 to 16.5 or the average H number is from 8 to 25.5, the RCO-groups therein each contain 5 to 7, or an average of 5 to 7.5, carbon atoms and the value of x in each ester molecule is an integer of 1 to 3 or the average value of x in the mixture is from 1 to 3. The H number of a carboxylic acid is computed by summing prescribed values allotted to the number and character of the carbon atoms a -, b - and g - to the carboxylic group and to the number and position of any aromatic rings present. H numbers are given for numerous carboxylic acids whose acyl groups may be present singly or in admixture in the esters or ester mixtures, including straight and branched chain alkanoic, cycloalkanoic, cycloalkylalkanoic, alkylcycloalkanoic, aromatic, aralkanoic and alkylaromatic acids; typical acids and their H numbers are acetic 0, benzoic 1, n-hexanoic 6.5, a -methylbutyric 10, triphenylacetic 13.5 and tri (t-butyl) acetic 37.5. Many examples are given of simple, mixed and mixtures of esters including dipentaerythritol hexa (a -ethylbutyrate), pentaerythritol tetra (a -ethylmethylbutyrate) and tripentaerythritol tetra (diisopropylacetate)-tri(acetate)-myristate. The esters or ester mixtures may be prepared by esterifying an appropriate polyol or mixture of polyols with an appropriate carboxylic acid or mixture of acids or with the anhydrides thereof. Suitably, the reaction is effected at about 125 DEG C. to 250 DEG C., under conditions favouring water removal in the presence of an esterification catalyst and if desired a solvent, using an excess of the carboxylic acid. Many suitable catalysts are specified. Alternatively, a polyol esterified with lower aliphatic acids may be heated under transesterification conditions with the required amount of appropriate acid or lower alkyl ester thereof until the desired ester is formed. The product is recovered by stripping off unchanged reagent and/or solvent under reduced pressure and may then be treated with carbon black. A product of minimum hydroxyl number may be obtained by treatment of the crude ester with e.g., acetic, propionic or butyric anhydride, acetyl chloride or a ketene and a product of minimum acidity by alkaline washing of the stripped ester. The esters may be used as plasticizers for chlorine-containing vinyl-type polymers (see Group IV(a)). Comparative experiments describe the preparation of various hexa-esters of dipentaerythritol not having the above specified characteristics and these esters are incompatible with polyvinyl chloride.
GB10882/58A 1957-04-09 1958-04-03 Pentaerythritol and polypentaerithritol esters and chlorinated polymers containing them Expired GB884660A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US884660XA 1957-04-09 1957-04-09

Publications (1)

Publication Number Publication Date
GB884660A true GB884660A (en) 1961-12-13

Family

ID=22211543

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10882/58A Expired GB884660A (en) 1957-04-09 1958-04-03 Pentaerythritol and polypentaerithritol esters and chlorinated polymers containing them

Country Status (1)

Country Link
GB (1) GB884660A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0067813A1 (en) * 1980-12-31 1982-12-29 Du Pont Acrylic resin with antiplasticizer.
EP0351142A2 (en) * 1988-07-13 1990-01-17 Neste Oy Crosslinkable silyl polymer composition
WO2012026861A1 (en) * 2010-08-23 2012-03-01 Perstorp Ab Non-phthalic plasticiser

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0067813A1 (en) * 1980-12-31 1982-12-29 Du Pont Acrylic resin with antiplasticizer.
EP0067813A4 (en) * 1980-12-31 1983-06-08 Du Pont Acrylic resin with antiplasticizer.
EP0351142A2 (en) * 1988-07-13 1990-01-17 Neste Oy Crosslinkable silyl polymer composition
EP0351142A3 (en) * 1988-07-13 1990-11-07 Bp Chemicals Limited Crosslinkable silyl polymer composition
US5028680A (en) * 1988-07-13 1991-07-02 Bp Chemicals Limited Crosslinkable silyl polymer composition
WO2012026861A1 (en) * 2010-08-23 2012-03-01 Perstorp Ab Non-phthalic plasticiser
CN103201328A (en) * 2010-08-23 2013-07-10 佩什托普公司 Non-phthalic plasticiser
CN103201328B (en) * 2010-08-23 2015-03-25 佩什托普公司 Non-phthalic plasticiser
US20150203657A1 (en) * 2010-08-23 2015-07-23 Perstorp Ab Non-phthalic plasticiser
RU2559449C2 (en) * 2010-08-23 2015-08-10 Персторп АБ Naphthalate plasticiser
CN105061807A (en) * 2010-08-23 2015-11-18 佩什托普公司 Non-Phthalic Plasticiser
CN105061807B (en) * 2010-08-23 2018-03-02 佩什托普公司 Non-neighboring terephthalate-type plasticizer
US10815361B2 (en) * 2010-08-23 2020-10-27 Perstorp Ab Non-phthalic plasticiser

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