CA1116768A - Craze-resistant plasticized sulfur compositions - Google Patents
Craze-resistant plasticized sulfur compositionsInfo
- Publication number
- CA1116768A CA1116768A CA000309502A CA309502A CA1116768A CA 1116768 A CA1116768 A CA 1116768A CA 000309502 A CA000309502 A CA 000309502A CA 309502 A CA309502 A CA 309502A CA 1116768 A CA1116768 A CA 1116768A
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- Canada
- Prior art keywords
- sulfur
- composition according
- composition
- triarylphosphate
- plasticizer
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D1/00—Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
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- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A composition comprising sulfur, a sulfur plasticizer other than styrene or dipentene dimercaptan a filler,and a triarylphosphate has exceptional craze resistance when used as a coating formulation.
A composition comprising sulfur, a sulfur plasticizer other than styrene or dipentene dimercaptan a filler,and a triarylphosphate has exceptional craze resistance when used as a coating formulation.
Description
'7~
BACKGROUND OF ~IE INVENTION
The present invention concerns a plasticized-sulfur composi-tion and concentrates useful in its preparation. In particular, the - fully formulated composition comprises sulfur, a sulfur plasticizer, a filler and a triarylphosphate. The composition is particularly useful as a coating material due to its surprising resistance to crazing under freeze-thaw cyclic weather conditions.
Plasticized-sulfur compositions are well known in the coating art. Various references disclose and compare the properties of these compositions. For instance, United States Patent 3,823,019 describes plasticized-sulfur compositions comprising sulfur, dicyclopentadiene, glass fiber and talc. United States Patent 3,290,266 describes plas-ticized-sulfur compositions comprising sulfur and a polymeric plasti-cizer. United States Patent 4,026,719 describes various plasticized-sulfur compositions. In particular, this patent discloses the use of mica as a filler which imparts exceptional strength to the composi-tions.
As the general state of the suLfur and plasticized-sulfur coating art developed it became clear that these compositions were limited by their tendency to craze or crack when exposed to expansion or contraction stresses. Many coating applications, such as the coating of vessels intended to hold corrosive materials, require an essentially craze-free coating Thus, in many cases the useful life of the coating is determined by its craze-resistance.
SU~ARY OF THE INVENTION
It has been found that the craze-resistance of ~ conventional plasticized-sulfur compositions can be signif:l.cantly : enhanced by adding from about 0.1% to about 30%, by weight, of a triarylphosphate to the fully formulated composition.
Concentrates which comprise from about 40% to about 80%, by weight of the triarylphosphate and a sulfur-plasticizer facilit-ate formulation of the improved composition.
DETAILED DESCRIPTION OF THE INVENTION
Among other factors, the present invention is based upon the improved properties of plasticized-sulfur coating compositions which result from the addition of a triarylphos-phate to the composition. Accordingly, this invention provides a plasticized-sulfur composition comprising sulfur, a sulfur plasticizer other than styrene or dipentene dimercaptan, a filler, and a triarylphosphate. The composition is useful as `
a coating material in applications such as water impoundment, floorin~, embankment consolidation, vessel lining, and the like.
In all such applications the craze-resistance of the composition is important. A plasticized-sulfur composition containing a triarylphosphate has been found -to provide significantly im-proved craze-resis-tance. Thus, the advantages of the composition of this invention over previously proposed compositions can be readily appreciated.
The concentrations of the various ingredients which make up the fully formulated composition may vary over a broad ; range. However, for general guidance best results have been ` observed where the fully formulated composition comprises from about 50~ to about 98~ sulfur, from about 0.1% to about 30%
sulfur plasticizer, from about 1% to 40% filler, and from about 0~1% to about 30~ triarylphosphate (all percent concentrations used to describe the invention, unless otherwise stated, are in weight percent based upon total weight of sulfur, filler and triarylphosphate in the composition)~
Sulfur is the major ingredient of the composition.
~hen fully formulated, the composition will typically comprise at least 50% sulfur, preferably from about 60% to about 95%, and 6~
most preferably from about 70~ to about 90%. The sulfur may be present in the composition as an element of the sulfur plastic-izer, but normally the other ingredients of the composition are added to molten elemental sulfur to form a sulfur-based formu-lation.
The composition of this invention includes a sulfur plasticizer. When fully formulated, the composition will typically comprise at least 0~1% plasticizer, preferably from about 0.5% to about 25%, and most preferably from about 1% to about 5%. Sulfur plasticizers are well known materials. The term is generally used to describe materials which combine with sulfux and lower its melting point. Plasticized-sulfur therefore requires a longer time to crystallize than molten elemental sulfur. The rate of crystallization can be measured by melting a fixed amount of the material on a microscopic slide at 130C, maintaining the sample at about 78C using a surface pyrometer to determine temperature, seeding a corner of the sample with a crystal of the material, and recording the time required for complete crystallization of the sample. Accordingly, as used herein and in conventional use the term "sulfur plasticizer"
contemplates materials which, when added to molten elemental sulfur, increase the crystallization time in reference to the elemental sulfur itself.
Both inorganic and organic sulfur plasticizers are well known. Inorganic plasticizers include, for example, iron, arsenic, and phosphorus sulfides. However, organic plasticizers which xeact with sulfur are more commonly used to plasticize sulfur. Suitable organic sulfur plasticizers include, for example, aliphatic polysulfides, aromatic polysulfides, dicyclo-pentadiene, dioctylphthalate, acrylic acid, epoxidized soybeanoil, triglycerides, and tall oil fatty acids. The I ~
, ~ - 4 -aliphatic and aromatic polysulfides are preferred sulfur plasticizers, particularly those which do not form significantly cross-linked materials.
Thus, linear aliphatic polysulfides are one class of preferred polysul-fide plasticizer. They may be branched such as the linear polysulfides described by the recurring unit:
-Sx-C-c-sx-wherein x is an integer from 2 to about 6 and Z is a hydrogen~ alkyl, aryl, halogen, nitrile, ester or amide moiety~ Thus, the chain with sulfur is a linear aliphatic chain, but may contain aromatic or hetero side groups. For instance, styrene can be used to form a phenyl substi-tuted linear aliphatic polysulfide. The aliphatic polysulfides may also be unbranched such as those described by the recurring unit -SXcll2ctl2oc~l2oc~l2c~l2sx-wherein x has an average value of about 12. The ether function of the polysulfide is relatively inert. Other suitable aliphatic polysulfides havln~ recurring ~mits such as -Sx~C1~123ySx~, -SX~CH2CH2-S-CH2CH23ySx~, or ~, -SX~cH2cH2-o-cH2cH2~ysx wherein x is an integer from 2 to about 5 and y is an integer from 2 to about 10. Aromatic polysulfides formed by reacting at , least two mols of sulfur with one mol of an aromatic carbocyclic ! or heterocyclic compound substituted by at least one functional _ 5 _ ~,~
~67~
group of the class -OH or ~NHR in which R is hydrogen or lower alkyl are another class of preferred polysulfide plasticizer.
These as well as other suitable sulfur plasticizers are disclosed in United States Patent 4,026,219. For example, the reaction product of phenol and sulfur is a preferred plasticizer and is generally called a phenol-sulfur adduct. In particular, these disclosures describe suitable mixtures of sulfur plasticizers such as mixtures of aliphatic polysulfides with dicyclopenta-diene.
The third ingredient of the composition of this inven-tion is a filler. Organic and inorganic, particulate and fibrous fillers are conventionally included in plasticized-sulfur coating compositions. In general, when fully formulated, the composition will comprise at least 1% filler, preerably from about 5% to about 30%, and most preferably from about 10% to about 20%.
Suitable fillers include, for example, glass fibers, asbestos, talc, clay, mica, and the like. Mica is particularly suited.
United States Patent 4,026,719 thoroughly describes mica fillers which are preferred for use in the composition of this invention.
As indicated in the previous description of the composi-tion of this invention, a triarylphosphate is the most critical ingredient of the composition. In general, the fully formulated composition will comprise at least 0.1% triarylphosphate, pre-ferably from about 0.5% to about 25%, and most preferably from about 1% to about 5~. The triarylphosphates have some plasticiz-ing properties, but for purposes of this description, they are distinguished from the sulfur plasticizer which is an ingredient of the composition. Thus, the total concentration o~E triaryl-phosphate in the fully formulated composition may exceed 30%, if the amount of sulfur plasticizer is less than 30%.
6~
Suitable triarylphosphates include, for example, phosphates having from 6 to about 12 carbon atoms in cach aryl substituent. The aryl substitu-ents can be similar or dissimilar and may have a condensed or fused ring system. Accordingly, preferred triarylphosphates have the structure o Ar-O-P-O-Ar o Ar wherein Ar is an aryl group containing from 6 to about 12 carbon atoms, optionally substituted with from 1 ~o 5 halogen atoms, preferably chlor-ine. The three Ar groups may be the same or different. Specific suit-able aryl group include, for e~cample, phenyl, benzyl, naphthyl, tolyl, xylyl, mixed ethyl phenyls, 4-t-butylphenyl, pentachlorophenyl, 3-bromophenyl, p-phenylphenyl, 2-methyl-1-naphthyl, and the like. Aryls which are substituted by alkyl groups containing more than one carbon atom, i.e., al~ylaryls "~hile s~litable are less proferred since they may liberate ~12S or CS2 cluring formulation. Triphellylphosphate and tribenzylphosphate are the preferred triarylphosphates.
Aryl phosphates are made by the reaction of the phenol with phosphorus o~ychloride:
3ArOH I POC13~ ~ArO)3P0 ~ 3HCl.
In addition to the four essential ingredients described above, the composition of this invention may optionally comprise various other adjuvants such as pigments, stabilizers, aggregates including sand, gravel, or rock, and the like. Particularly where aggregate is included, t1~e adjuvants may be present in amounts up to as moch as 90% by weight of the total composition.
r ~L6~B
The composition of this invention can be prepared in molten form by mi~ing the ingredients at a temperature above the melting point of the composition. For most embodiments, a - temperature between about 110 C and 180 C, preferably between about 125 C and 150 C, is sufficient. ~lowever, for most applications, the composition is prepared from a concentrate comprising the sulfur plasticizer and the triarylphosphate. In addition, the concentrate may contain the filler or a fraction of the filler and/or a fraction of the sulfur present in the fully formulated composition. Thus, this invention contemplates a con-centrate which when diluted by the addition of sulfur and filler provi(les a fully formulated plasticized-sulfur coating composition.
The relative concentration of the plasticizer and triarylphosphate in the concentrate will depend upon the desired relative concen-tration in the fully formulated composition. A concentrate comprisin~ the sulfur plasticizer and tho triarylphosphate in a weight ratio of plasticizer to phosphate of from about 3:1 to about 1:3 is satisfactory for most applications.
The most practical method of preparing the composition of this invention from a concentrate is to add the concentrate and additional filler as well as any other optional adjuvant to molten sulfur at a temperature above the melting point of the composition. The order of addition is not critical, although for thorough mi~ing aggregate, if used, should be added a fraction at a time or continuously during the entire formulation process.
The fully formulated composition is usually applied in molten form by, for e~ample~ spraying or painting a coat onto the surface to be covered. For most surfaces a llS" to 1/4" uniform coat will provide complete coverage.
E~IPLES
The following examples illustrate a variety of embodiments of the composition and concentrate of this invention.
The examples also suggest numerous modifications within the scope of the claims which follow, and therefore are not presented to limit the scope of the invention.
Examples 1-10 The plasticized-sulfur coatings summari~ed in Table I
which comprise sulfur, a sulfur plastici7er, a filler, and a triarylphosphate are prepared in molten form by heating and mixing the components at a temperature of about 130C.
, 1~
TABLE I
Ex.
No. Sulfur, % Plasticizer, % Filler, % Triarylphosphate,%
1 50 DCP 5 Talc 40 Triphenyl-phosphate 5
BACKGROUND OF ~IE INVENTION
The present invention concerns a plasticized-sulfur composi-tion and concentrates useful in its preparation. In particular, the - fully formulated composition comprises sulfur, a sulfur plasticizer, a filler and a triarylphosphate. The composition is particularly useful as a coating material due to its surprising resistance to crazing under freeze-thaw cyclic weather conditions.
Plasticized-sulfur compositions are well known in the coating art. Various references disclose and compare the properties of these compositions. For instance, United States Patent 3,823,019 describes plasticized-sulfur compositions comprising sulfur, dicyclopentadiene, glass fiber and talc. United States Patent 3,290,266 describes plas-ticized-sulfur compositions comprising sulfur and a polymeric plasti-cizer. United States Patent 4,026,719 describes various plasticized-sulfur compositions. In particular, this patent discloses the use of mica as a filler which imparts exceptional strength to the composi-tions.
As the general state of the suLfur and plasticized-sulfur coating art developed it became clear that these compositions were limited by their tendency to craze or crack when exposed to expansion or contraction stresses. Many coating applications, such as the coating of vessels intended to hold corrosive materials, require an essentially craze-free coating Thus, in many cases the useful life of the coating is determined by its craze-resistance.
SU~ARY OF THE INVENTION
It has been found that the craze-resistance of ~ conventional plasticized-sulfur compositions can be signif:l.cantly : enhanced by adding from about 0.1% to about 30%, by weight, of a triarylphosphate to the fully formulated composition.
Concentrates which comprise from about 40% to about 80%, by weight of the triarylphosphate and a sulfur-plasticizer facilit-ate formulation of the improved composition.
DETAILED DESCRIPTION OF THE INVENTION
Among other factors, the present invention is based upon the improved properties of plasticized-sulfur coating compositions which result from the addition of a triarylphos-phate to the composition. Accordingly, this invention provides a plasticized-sulfur composition comprising sulfur, a sulfur plasticizer other than styrene or dipentene dimercaptan, a filler, and a triarylphosphate. The composition is useful as `
a coating material in applications such as water impoundment, floorin~, embankment consolidation, vessel lining, and the like.
In all such applications the craze-resistance of the composition is important. A plasticized-sulfur composition containing a triarylphosphate has been found -to provide significantly im-proved craze-resis-tance. Thus, the advantages of the composition of this invention over previously proposed compositions can be readily appreciated.
The concentrations of the various ingredients which make up the fully formulated composition may vary over a broad ; range. However, for general guidance best results have been ` observed where the fully formulated composition comprises from about 50~ to about 98~ sulfur, from about 0.1% to about 30%
sulfur plasticizer, from about 1% to 40% filler, and from about 0~1% to about 30~ triarylphosphate (all percent concentrations used to describe the invention, unless otherwise stated, are in weight percent based upon total weight of sulfur, filler and triarylphosphate in the composition)~
Sulfur is the major ingredient of the composition.
~hen fully formulated, the composition will typically comprise at least 50% sulfur, preferably from about 60% to about 95%, and 6~
most preferably from about 70~ to about 90%. The sulfur may be present in the composition as an element of the sulfur plastic-izer, but normally the other ingredients of the composition are added to molten elemental sulfur to form a sulfur-based formu-lation.
The composition of this invention includes a sulfur plasticizer. When fully formulated, the composition will typically comprise at least 0~1% plasticizer, preferably from about 0.5% to about 25%, and most preferably from about 1% to about 5%. Sulfur plasticizers are well known materials. The term is generally used to describe materials which combine with sulfux and lower its melting point. Plasticized-sulfur therefore requires a longer time to crystallize than molten elemental sulfur. The rate of crystallization can be measured by melting a fixed amount of the material on a microscopic slide at 130C, maintaining the sample at about 78C using a surface pyrometer to determine temperature, seeding a corner of the sample with a crystal of the material, and recording the time required for complete crystallization of the sample. Accordingly, as used herein and in conventional use the term "sulfur plasticizer"
contemplates materials which, when added to molten elemental sulfur, increase the crystallization time in reference to the elemental sulfur itself.
Both inorganic and organic sulfur plasticizers are well known. Inorganic plasticizers include, for example, iron, arsenic, and phosphorus sulfides. However, organic plasticizers which xeact with sulfur are more commonly used to plasticize sulfur. Suitable organic sulfur plasticizers include, for example, aliphatic polysulfides, aromatic polysulfides, dicyclo-pentadiene, dioctylphthalate, acrylic acid, epoxidized soybeanoil, triglycerides, and tall oil fatty acids. The I ~
, ~ - 4 -aliphatic and aromatic polysulfides are preferred sulfur plasticizers, particularly those which do not form significantly cross-linked materials.
Thus, linear aliphatic polysulfides are one class of preferred polysul-fide plasticizer. They may be branched such as the linear polysulfides described by the recurring unit:
-Sx-C-c-sx-wherein x is an integer from 2 to about 6 and Z is a hydrogen~ alkyl, aryl, halogen, nitrile, ester or amide moiety~ Thus, the chain with sulfur is a linear aliphatic chain, but may contain aromatic or hetero side groups. For instance, styrene can be used to form a phenyl substi-tuted linear aliphatic polysulfide. The aliphatic polysulfides may also be unbranched such as those described by the recurring unit -SXcll2ctl2oc~l2oc~l2c~l2sx-wherein x has an average value of about 12. The ether function of the polysulfide is relatively inert. Other suitable aliphatic polysulfides havln~ recurring ~mits such as -Sx~C1~123ySx~, -SX~CH2CH2-S-CH2CH23ySx~, or ~, -SX~cH2cH2-o-cH2cH2~ysx wherein x is an integer from 2 to about 5 and y is an integer from 2 to about 10. Aromatic polysulfides formed by reacting at , least two mols of sulfur with one mol of an aromatic carbocyclic ! or heterocyclic compound substituted by at least one functional _ 5 _ ~,~
~67~
group of the class -OH or ~NHR in which R is hydrogen or lower alkyl are another class of preferred polysulfide plasticizer.
These as well as other suitable sulfur plasticizers are disclosed in United States Patent 4,026,219. For example, the reaction product of phenol and sulfur is a preferred plasticizer and is generally called a phenol-sulfur adduct. In particular, these disclosures describe suitable mixtures of sulfur plasticizers such as mixtures of aliphatic polysulfides with dicyclopenta-diene.
The third ingredient of the composition of this inven-tion is a filler. Organic and inorganic, particulate and fibrous fillers are conventionally included in plasticized-sulfur coating compositions. In general, when fully formulated, the composition will comprise at least 1% filler, preerably from about 5% to about 30%, and most preferably from about 10% to about 20%.
Suitable fillers include, for example, glass fibers, asbestos, talc, clay, mica, and the like. Mica is particularly suited.
United States Patent 4,026,719 thoroughly describes mica fillers which are preferred for use in the composition of this invention.
As indicated in the previous description of the composi-tion of this invention, a triarylphosphate is the most critical ingredient of the composition. In general, the fully formulated composition will comprise at least 0.1% triarylphosphate, pre-ferably from about 0.5% to about 25%, and most preferably from about 1% to about 5~. The triarylphosphates have some plasticiz-ing properties, but for purposes of this description, they are distinguished from the sulfur plasticizer which is an ingredient of the composition. Thus, the total concentration o~E triaryl-phosphate in the fully formulated composition may exceed 30%, if the amount of sulfur plasticizer is less than 30%.
6~
Suitable triarylphosphates include, for example, phosphates having from 6 to about 12 carbon atoms in cach aryl substituent. The aryl substitu-ents can be similar or dissimilar and may have a condensed or fused ring system. Accordingly, preferred triarylphosphates have the structure o Ar-O-P-O-Ar o Ar wherein Ar is an aryl group containing from 6 to about 12 carbon atoms, optionally substituted with from 1 ~o 5 halogen atoms, preferably chlor-ine. The three Ar groups may be the same or different. Specific suit-able aryl group include, for e~cample, phenyl, benzyl, naphthyl, tolyl, xylyl, mixed ethyl phenyls, 4-t-butylphenyl, pentachlorophenyl, 3-bromophenyl, p-phenylphenyl, 2-methyl-1-naphthyl, and the like. Aryls which are substituted by alkyl groups containing more than one carbon atom, i.e., al~ylaryls "~hile s~litable are less proferred since they may liberate ~12S or CS2 cluring formulation. Triphellylphosphate and tribenzylphosphate are the preferred triarylphosphates.
Aryl phosphates are made by the reaction of the phenol with phosphorus o~ychloride:
3ArOH I POC13~ ~ArO)3P0 ~ 3HCl.
In addition to the four essential ingredients described above, the composition of this invention may optionally comprise various other adjuvants such as pigments, stabilizers, aggregates including sand, gravel, or rock, and the like. Particularly where aggregate is included, t1~e adjuvants may be present in amounts up to as moch as 90% by weight of the total composition.
r ~L6~B
The composition of this invention can be prepared in molten form by mi~ing the ingredients at a temperature above the melting point of the composition. For most embodiments, a - temperature between about 110 C and 180 C, preferably between about 125 C and 150 C, is sufficient. ~lowever, for most applications, the composition is prepared from a concentrate comprising the sulfur plasticizer and the triarylphosphate. In addition, the concentrate may contain the filler or a fraction of the filler and/or a fraction of the sulfur present in the fully formulated composition. Thus, this invention contemplates a con-centrate which when diluted by the addition of sulfur and filler provi(les a fully formulated plasticized-sulfur coating composition.
The relative concentration of the plasticizer and triarylphosphate in the concentrate will depend upon the desired relative concen-tration in the fully formulated composition. A concentrate comprisin~ the sulfur plasticizer and tho triarylphosphate in a weight ratio of plasticizer to phosphate of from about 3:1 to about 1:3 is satisfactory for most applications.
The most practical method of preparing the composition of this invention from a concentrate is to add the concentrate and additional filler as well as any other optional adjuvant to molten sulfur at a temperature above the melting point of the composition. The order of addition is not critical, although for thorough mi~ing aggregate, if used, should be added a fraction at a time or continuously during the entire formulation process.
The fully formulated composition is usually applied in molten form by, for e~ample~ spraying or painting a coat onto the surface to be covered. For most surfaces a llS" to 1/4" uniform coat will provide complete coverage.
E~IPLES
The following examples illustrate a variety of embodiments of the composition and concentrate of this invention.
The examples also suggest numerous modifications within the scope of the claims which follow, and therefore are not presented to limit the scope of the invention.
Examples 1-10 The plasticized-sulfur coatings summari~ed in Table I
which comprise sulfur, a sulfur plastici7er, a filler, and a triarylphosphate are prepared in molten form by heating and mixing the components at a temperature of about 130C.
, 1~
TABLE I
Ex.
No. Sulfur, % Plasticizer, % Filler, % Triarylphosphate,%
1 50 DCP 5 Talc 40 Triphenyl-phosphate 5
2 60 LP-3 * 1 Mica5 30 Tribenzyl-phosphate 9
3 80 PSA3 2 Abestos 16 Tri(ethylphenyl)-phosphate 2
4 90 PSA 2 Clay 2 Trinaphthyl-LP-3 1 phosphate 5 DCP 10 Glass7 25 Triphenyl-phospha-te 5 6 60 PSA 2 Mica 20 Tri(dimethylphen-yl)-phosphate 18 7 70 LP-3* 5 CaCO 20 Tritolyl-3 phosphate 5 8 80 DCP 5 Mica 15 Tritbisphenyl)-phosphate 10 9 90 DCP 2 Talc 1 Tri(butylphenyl)-LP-3* 1 Asbestos 1 phosphate 5 LP-3* 1 Mica 1 Triphenyl-phosphate 3 Dicyclopentadiene.
3I.inear aliphatic polysulfide sold by Thiokol Co.
Phenol-sulfur adduct.
4Mistron Vapor.*
C-3000* sold by English Mica Co. having a 6 particle size of 5-10 microns by 0.5 micron.
7Kaopague-30*.
0.25" milled glass fiber.
Example 11 A plasticized-sulfur coating composition was prepared by heating and mixing 79% sulfur, ~% phenol-sulfur adduct, 18%
mica, and 1% triphenylphosphate at a temperature of abc,ut 130 C.
The resulting composition was applied to a 10-foot by 6-foot T-shaped mortarless cinderbrick wall. The composition was thixo-tropic and did not sag or drip during application.
The composition was evaluated for flexural strength, tensile strength, and compressive strength. These properties are summarized in Table II.
* Trademarks ~, - 1 0 -TABLE II
Flexural Tensile Compressive Strength Strength Strength psi psi psi The composition was also evaluated for craze-resistance under cycling temperature conditions. In these tests the composition con-tained 7g% sulfur, 2% phenol-sulfur adduct, and 18% mica. The results are given in Table III.
TABLE III
Ex. Anti-Crazing Tes~ I, Cycles~ ) Test II, Cycles No. Additive, % Failure No Failure Failure No Failure 12 LP-~2)) 1 60 6 14 TCP(3)4) 1 38 lS BPDPP 1 38 (1) LP-3 is a linear aliphatic polysulfide.
(2) Triphenylphosphate.
~3) Tricresylphosphate.
(4) t-Butylphenyl diphenyl phosphate.
3I.inear aliphatic polysulfide sold by Thiokol Co.
Phenol-sulfur adduct.
4Mistron Vapor.*
C-3000* sold by English Mica Co. having a 6 particle size of 5-10 microns by 0.5 micron.
7Kaopague-30*.
0.25" milled glass fiber.
Example 11 A plasticized-sulfur coating composition was prepared by heating and mixing 79% sulfur, ~% phenol-sulfur adduct, 18%
mica, and 1% triphenylphosphate at a temperature of abc,ut 130 C.
The resulting composition was applied to a 10-foot by 6-foot T-shaped mortarless cinderbrick wall. The composition was thixo-tropic and did not sag or drip during application.
The composition was evaluated for flexural strength, tensile strength, and compressive strength. These properties are summarized in Table II.
* Trademarks ~, - 1 0 -TABLE II
Flexural Tensile Compressive Strength Strength Strength psi psi psi The composition was also evaluated for craze-resistance under cycling temperature conditions. In these tests the composition con-tained 7g% sulfur, 2% phenol-sulfur adduct, and 18% mica. The results are given in Table III.
TABLE III
Ex. Anti-Crazing Tes~ I, Cycles~ ) Test II, Cycles No. Additive, % Failure No Failure Failure No Failure 12 LP-~2)) 1 60 6 14 TCP(3)4) 1 38 lS BPDPP 1 38 (1) LP-3 is a linear aliphatic polysulfide.
(2) Triphenylphosphate.
~3) Tricresylphosphate.
(4) t-Butylphenyl diphenyl phosphate.
(5) 1 cycle equals 8 houOrs at 70C and 16 hours at about 5 C.
~6) 1 cycle equalO S hours at 70C and 16 hours at 0 C.
E~ample 12, a good non-crazing composition without a triaryl phosphate, resisted crazing for 60 cycles in Test I and for 6 cycles in Test II, ~hereas a comparative composition containing triphenyl phosphate did not craze until 90 and 28 cycles respectively.
In Test I, compositions containing different aliphatic phosphates failed after 7 to 9 cycles.
~6) 1 cycle equalO S hours at 70C and 16 hours at 0 C.
E~ample 12, a good non-crazing composition without a triaryl phosphate, resisted crazing for 60 cycles in Test I and for 6 cycles in Test II, ~hereas a comparative composition containing triphenyl phosphate did not craze until 90 and 28 cycles respectively.
In Test I, compositions containing different aliphatic phosphates failed after 7 to 9 cycles.
Claims (15)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A composition comprising from about 50% to about 98%
sulfur, from about 0.1% to about 30% sulfur plasticizer other than styrene or dipentene dimercaptan, from about 1% to about 40% filler, and from about 0.1% to about 30% triarylphosphate.
sulfur, from about 0.1% to about 30% sulfur plasticizer other than styrene or dipentene dimercaptan, from about 1% to about 40% filler, and from about 0.1% to about 30% triarylphosphate.
2. A composition according to claim 1 comprising from about 60% to about 95% sulfur, from about 0.5% to about 25%
sulfur plasticizer, from about 5% to about 30% filler, and from about 0.5% to about 25% triarylphosphate.
sulfur plasticizer, from about 5% to about 30% filler, and from about 0.5% to about 25% triarylphosphate.
3. A composition according to claim 2 comprising from about 70% to about 90% sulfur, from about 1% to about 5% sulfur plasticizer, from about 10% to about 20% filler, and from about 1% to about 5% triarylphosphate.
4. A composition according to claim 1 wherein said sulfur plasticizer is a linear aliphatic polysulfide; an aromatic polysulfide formed by reacting at least two moles of sulfur per mol of an aromatic carbocyclic or a heterocyclic compound, sub-stituted by at least one function group of the class -OH or -NHR
in which R is hydrogen or lower alkyl; dicyclopentadiene; acrylic acid; tall oil fatty acids; dioctylphthalate; or mixtures there-of.
in which R is hydrogen or lower alkyl; dicyclopentadiene; acrylic acid; tall oil fatty acids; dioctylphthalate; or mixtures there-of.
5. A composition according to claim 1 wherein said filler is talc, clay, glass fiber, asbestos, mica, or mixtures thereof.
6. A composition according to claim 1 wherein said triaryl-phosphate contains from 6 to about 12 carbon atoms in each aryl substituent.
7. A composition according to claim 1 wherein the sulfur plasticizer is an aromatic polysulfide formed by reacting at least two mols of sulfur per mol of an aromatic carbocyclic or heterocyclic compound substituted by at least one functional group of the class -OH or -NHR in which R is hydrogen or lower alkyl; the filler is mica; and the triarylphosphate is triphenyl-phosphate.
8. A composition according to claim 7 comprising sulfur, a phenol-sulfur adduct formed by reacting at least two moles of sulfur per mol of phenol, mica, and triphenylphosphate.
9. A composition according to claim 7 comprising about 79% sulfur, about 2% phenol-sulfur adduct, about 18% mica, and about 1% triphenylphosphate.
10. A composition according to claim 1 wherein said tri-arylphosphate is triphenylphosphate.
11. A composition according to claim 1 wherein said com-position includes from about 1% to about 25% triarylphosphate.
12. A composition according to claim 1 wherein said com-position includes from about 1% to about 5% triarylphosphate.
13. A concentrate, which is useful to prepare a plastic-ized sulfur composition, comprising a sulfur plasticizer other than styrene and dipentene dimercaptan and a triarylphosphate and wherein the weight ratio of said plasticizer to said tri-arylphosphate is from about 3:1 to about 1:3.
14. A concentrate according to claim 13 wherein said weight ratio is 2:1.
15. A concentrate according to claim 13 wherein said con-centrate includes a fraction of the sulfur and filler used in the fully formulated composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83285477A | 1977-09-13 | 1977-09-13 | |
| US832,854 | 1977-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1116768A true CA1116768A (en) | 1982-01-19 |
Family
ID=25262781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000309502A Expired CA1116768A (en) | 1977-09-13 | 1978-08-17 | Craze-resistant plasticized sulfur compositions |
Country Status (7)
| Country | Link |
|---|---|
| CA (1) | CA1116768A (en) |
| DE (1) | DE2839348A1 (en) |
| FR (1) | FR2402691A1 (en) |
| GB (1) | GB2004261B (en) |
| IT (1) | IT1099067B (en) |
| MX (1) | MX4111E (en) |
| NL (1) | NL7809247A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5320871A (en) * | 1992-06-05 | 1994-06-14 | Springborn Laboratories, Inc. | Underwater coating for submerged substrates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1526113A (en) * | 1966-04-04 | 1968-05-24 | Aquitaine Petrole | Process for making sulfur non-flammable or self-extinguishing and composition |
-
1978
- 1978-08-17 CA CA000309502A patent/CA1116768A/en not_active Expired
- 1978-08-25 FR FR7824719A patent/FR2402691A1/en not_active Withdrawn
- 1978-09-09 DE DE19782839348 patent/DE2839348A1/en not_active Withdrawn
- 1978-09-11 NL NL7809247A patent/NL7809247A/en not_active Application Discontinuation
- 1978-09-12 GB GB7836425A patent/GB2004261B/en not_active Expired
- 1978-09-12 MX MX787387U patent/MX4111E/en unknown
- 1978-09-13 IT IT27630/78A patent/IT1099067B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2004261A (en) | 1979-03-28 |
| GB2004261B (en) | 1982-03-24 |
| DE2839348A1 (en) | 1979-03-22 |
| IT7827630A0 (en) | 1978-09-13 |
| FR2402691A1 (en) | 1979-04-06 |
| IT1099067B (en) | 1985-09-18 |
| NL7809247A (en) | 1979-03-15 |
| MX4111E (en) | 1981-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |