WO1999030903A1 - Powder coating compositions based on empd polyester resins - Google Patents

Powder coating compositions based on empd polyester resins Download PDF

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Publication number
WO1999030903A1
WO1999030903A1 PCT/US1998/027285 US9827285W WO9930903A1 WO 1999030903 A1 WO1999030903 A1 WO 1999030903A1 US 9827285 W US9827285 W US 9827285W WO 9930903 A1 WO9930903 A1 WO 9930903A1
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WO
WIPO (PCT)
Prior art keywords
empd
polyester resins
powder coating
resin
propanediol
Prior art date
Application number
PCT/US1998/027285
Other languages
French (fr)
Inventor
Yeong-Ho Chang
Jamie Alicia Vaughn
Original Assignee
Eastman Chemical Company
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 Eastman Chemical Company filed Critical Eastman Chemical Company
Priority to PCT/US1998/027285 priority Critical patent/WO1999030903A1/en
Publication of WO1999030903A1 publication Critical patent/WO1999030903A1/en

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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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
    • C08G18/4219—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from aromatic dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/20—Compositions for powder coatings

Definitions

  • polyester resins for powder coatings are mostly based on terephthalic acid and isophthalic acid as diacids and neopentyl glycol as diol with minor variations.
  • Powder coatings based on these aromatic polyester resins provide good general properties but only fair appearance.
  • WO 97/16401 describes reaction mixtures containing substituted hydrocarbon diols and their preparation and using in coatings.
  • the disclosure includes preparation of 2,2-disubstituted hydrocarbon diols and more specifically
  • polyesters derived from such diols and their utility in coatings, ink, sealant and adhesive composition.
  • polyesters and processes for preparing same are prepared from a diacids such as terephthalic acid or isophthalic acid and a diol, preferably, from 2,2-disubstituted 1 ,3-propanediol and more specifically 2-ethyl-2-methyl-1,3-propanediol.
  • the application further described curable coating, ink, sealant and adhesive compositions based on such polyesters.
  • the present invention describes polyesters specifically derived from 1- ethyl-2-methyl-1 ,3-propanediol (EMPD) and the coatings derived from such polyesters. It has been found that polyester resins based on 1-ethyl-2-methyl-1 ,3- propanediol (EMPD) meets the basic Tg (glass transition temperature) requirement for powder coatings and can be formulated into thermosetting powder coatings with excellent appearance.
  • EMPD 1- ethyl-2-methyl-1 ,3-propanediol
  • This invention relates to polyester resins made of neopentyl glycol (NPG) and 1-ethyl-2-methyl-1 ,3-propanediol (EMPD), CAS registry number 149-31-9, and the thermosetting powder coatings based on these polyester resins.
  • the powder coatings exhibit better appearance than those without EMPD.
  • the resins of the present invention are mainly based on diols (glycols) from EMPD, NPG and on diacids mainly from terephthalic acid or isophthalic acid.
  • the resin may be modified with other diacids or diols. It has been found that these polyester resins meet the basic requirements of powder coating and have excellent appearance when formulated into powder coatings.
  • the polyester resins may be terminated predominately with hydroxyl groups or acid groups.
  • the polyester resin has a number average molecular weight ( Mn ) of from about 1 ,500 to about 10,000, preferably from about 2,000 to 6,000 , a glass transition temperature ( Tg ) of about 45°C to 100°C, preferably 50° to 70°C and hydroxyl number or acid number of from about 20 to 100, preferably from about 30 to about 80, for crosslinking.
  • the polyester resins are those composed of diols consisting of 1-55 mole % of EMPD and 99-45 mole % of NPG based on the total diols and diacids consisting of terephthalic acid or isophtahlic or combination thereof , and optionally branchers with more than three functional groups such as hydroxyl, carboxyl or a combination.
  • branchers are trimethylolpropane or trimethylolethane , trimelletic acid or dimethylopropionic acid.
  • the powder coatings of the present invention may be of different crosslinking chemistries utilizing the hydroxyl functional groups or the acid functional groups of polyester resins.
  • powder coatings based on hydroxyl polyester resins are ; (1) a polyurethane system made from hydroxyl resins and a polyisocyanate, (2) a glycoluril system from a hyroxyl resin and a glycoluril crosslinker such as tetramethoxymethyl glycoluril.
  • a polyurethane powder coating of this invention comprises of (a) a hydroxyl polyester resin described above , (b) a blocked polyisocyanate crosslinker, and (c) optionally, additives such as benzoin, flow aids , pigments and catalysts.
  • the blocked polyisocyanate crosslinker are those well known in the art of powder coatings. Examples include those which based on caprolactam blocked isophoronediisocyanates such as Huls B1530 , McWhorter 2400 , Ruco NI-2 or those which are based on caprolactam-blocked toluene 2,4-diisocyanate such as commercial McWhorter 2450 crosslinker or the self blocked uretdione of isophoronediisocyanate commercially available as Huls BF1540.
  • Additives commonly used include benzoin for reducing entrapped air or volatiles, flow aid such as Modaflow III or Modaflow 2000, catalysts such as dibutyltin dilaurate and pigments such as titanium dioxide.
  • a glycoluril powder coating of this invention comprises of (a) a hydroxyl polyester resin described above (b) a glycoluril family of "aminoplast” crosslinking agent, such as tetramethoxymethyl glycouril commercially available as Powderlink 1174, and (3) optionally, additives such as benzoin, flow aids , pigments and catalysts.
  • the powder coating of this invention may be of different crosslinking chemistries utilizing the acid functional group of the polyester resins.
  • powder coating system from (a) carboxyl polyester resins as described above, (b) an epoxy crosslinker such as triglycidylisocyanurate (TGIC) commercially available as Aradite PT-810 by Ciba Geigy or alternatively an activated B-hydroxylalkyl amide such as Bis(N,N-dihydroxyethyl)adipamide commercially available from EMS as PRIMID XL552 or PRIMID QM1260, or epoxy resins that are based on bisphenol A and (c) optionally, additives such as benzoin, flow aids , pigments and catalyst.
  • TGIC triglycidylisocyanurate
  • Additives commonly used ar$ benzoin for reducing entrapped air or volatiles flow aid such as Modaflow III, catalyst such as dibutyltin dilaurate and pigments such as titanium dioxide or stabilizer such as UV absorber (UVA) and hindered amine light stabilizer (HALS).
  • flow aid such as Modaflow III
  • catalyst such as dibutyltin dilaurate
  • pigments such as titanium dioxide or stabilizer
  • UV absorber UV absorber
  • HALS hindered amine light stabilizer
  • the acid number and hydroxyl number are determined by titration and reported as miligram (mg ) of KOH consumed for each gram of resin.
  • the glass transition temperature (Tg), is determined by differential scanning calorimetry (DSC) on the second heating cycle with a scanning rate of 20° C / minute after the sample has been heated to melt and quenched to below the resin Tg. Tg values are reported as midpoint.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) are determined by gel permeation chromatography in tetrahydrofuran (THF) using polystyrene standard and a UV detector.
  • the conical mandrel is performed using a Gardener Laboratory Inc., conical mandrel of specified size according to ASTM-522.
  • the 20 and 60 degree gloss are measured using a gloss meter (Gardener Laboratory, Inc. Model GC-9095) according to ASTM D-523.
  • Resin Examples 1 , 2 and 3 Resin preparation for hydroxyl resins. To a 2-liter reactor equipped with mechanical stirrer, heated packed column, distillation condenser, thermocouples, nitrogen stream and accessories needed for computer and Camile control are charged reactants, catalyst and excess glycol.
  • the content is heated gradually to melt the glycols to result in a slurry mix.
  • the mix is stirred as it becomes possible.
  • the reaction is maintained with a nitrogen stream and stirrer speed at 300 rpm and the cook schedule maintained by a heat control with computer control (Camile) as follows:
  • Water from the reaction is removed through a heated column and distillation condenser until an acid number of less than 5 is reached.
  • TMP Trimethylolpropane
  • Resin, crosslinker and additives are mixed in a Henschel mixer and compounded in a ZSK 30 extruder with temperature profile and screw speed as specified.
  • the extrudate is cooled through a chili roll, granulated and pulverized using a Bantam mill with liquid nitrogen bled into the grinding chamber.
  • the powder is classified through a 200 mesh screen.
  • the powder is electrostatically applied to 3 in. x 9 in. metal panels and cured in oven as specified temperature and time.
  • Table 2 Powder Coating Formulation
  • Zone 1 100 100 100 Zone 2 110 110 110 Feed Rate 200 200 200 Screw rpm 300 300 300

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)

Abstract

The present invention describes polyesters specifically derived from 1-ethyl-2-methyl-1,3-propanediol (EMPD) and the coatings derived from such polyesters. It has been found that polyester resins based on 1-ethyl-2-methyl-1,3-propanediol (EMPD) meets the basic Tg (glass transition temperature) requirement for powder coatings and can be formulated into thermosetting powder coatings with excellent appearence.

Description

POWDER COATING COMPOSITIONS BASED ON EMPD POLYESTER RESINS
Background of the Invention Powder coatings with good film appearance are becoming increasingly important as applications expand to replace traditional liquid coatings.
Examples where appearance is of utmost importance are automotive top coats, bath fixtures and home or office furnitures. Commercial polyester resins for powder coatings are mostly based on terephthalic acid and isophthalic acid as diacids and neopentyl glycol as diol with minor variations.
Powder coatings based on these aromatic polyester resins provide good general properties but only fair appearance.
WO 97/16401 describes reaction mixtures containing substituted hydrocarbon diols and their preparation and using in coatings. The disclosure includes preparation of 2,2-disubstituted hydrocarbon diols and more specifically
2-ethyl-2-methyl-1 ,3-propanediol. The application further described the polyesters derived from such diols and their utility in coatings, ink, sealant and adhesive composition.
WO 97/16473 describes polyesters and processes for preparing same. The polyester are prepared from a diacids such as terephthalic acid or isophthalic acid and a diol, preferably, from 2,2-disubstituted 1 ,3-propanediol and more specifically 2-ethyl-2-methyl-1,3-propanediol. The application further described curable coating, ink, sealant and adhesive compositions based on such polyesters. Brief Description of the Invention
The present invention describes polyesters specifically derived from 1- ethyl-2-methyl-1 ,3-propanediol (EMPD) and the coatings derived from such polyesters. It has been found that polyester resins based on 1-ethyl-2-methyl-1 ,3- propanediol (EMPD) meets the basic Tg (glass transition temperature) requirement for powder coatings and can be formulated into thermosetting powder coatings with excellent appearance. Description of Invention
This invention relates to polyester resins made of neopentyl glycol (NPG) and 1-ethyl-2-methyl-1 ,3-propanediol (EMPD), CAS registry number 149-31-9, and the thermosetting powder coatings based on these polyester resins. The powder coatings exhibit better appearance than those without EMPD. The resins of the present invention are mainly based on diols (glycols) from EMPD, NPG and on diacids mainly from terephthalic acid or isophthalic acid. The resin may be modified with other diacids or diols. It has been found that these polyester resins meet the basic requirements of powder coating and have excellent appearance when formulated into powder coatings. The polyester resins may be terminated predominately with hydroxyl groups or acid groups. The polyester resin has a number average molecular weight ( Mn ) of from about 1 ,500 to about 10,000, preferably from about 2,000 to 6,000 , a glass transition temperature ( Tg ) of about 45°C to 100°C, preferably 50° to 70°C and hydroxyl number or acid number of from about 20 to 100, preferably from about 30 to about 80, for crosslinking. The polyester resins are those composed of diols consisting of 1-55 mole % of EMPD and 99-45 mole % of NPG based on the total diols and diacids consisting of terephthalic acid or isophtahlic or combination thereof , and optionally branchers with more than three functional groups such as hydroxyl, carboxyl or a combination. Examples of branchers are trimethylolpropane or trimethylolethane , trimelletic acid or dimethylopropionic acid.
The powder coatings of the present invention may be of different crosslinking chemistries utilizing the hydroxyl functional groups or the acid functional groups of polyester resins. Examples of powder coatings based on hydroxyl polyester resins are ; (1) a polyurethane system made from hydroxyl resins and a polyisocyanate, (2) a glycoluril system from a hyroxyl resin and a glycoluril crosslinker such as tetramethoxymethyl glycoluril. A polyurethane powder coating of this invention comprises of (a) a hydroxyl polyester resin described above , (b) a blocked polyisocyanate crosslinker, and (c) optionally, additives such as benzoin, flow aids , pigments and catalysts. The blocked polyisocyanate crosslinker are those well known in the art of powder coatings. Examples include those which based on caprolactam blocked isophoronediisocyanates such as Huls B1530 , McWhorter 2400 , Ruco NI-2 or those which are based on caprolactam-blocked toluene 2,4-diisocyanate such as commercial McWhorter 2450 crosslinker or the self blocked uretdione of isophoronediisocyanate commercially available as Huls BF1540.
Additives commonly used include benzoin for reducing entrapped air or volatiles, flow aid such as Modaflow III or Modaflow 2000, catalysts such as dibutyltin dilaurate and pigments such as titanium dioxide.
A glycoluril powder coating of this invention comprises of (a) a hydroxyl polyester resin described above (b) a glycoluril family of "aminoplast" crosslinking agent, such as tetramethoxymethyl glycouril commercially available as Powderlink 1174, and (3) optionally, additives such as benzoin, flow aids , pigments and catalysts.
Alternatively, the powder coating of this invention may be of different crosslinking chemistries utilizing the acid functional group of the polyester resins. For example, powder coating system from (a) carboxyl polyester resins as described above, (b) an epoxy crosslinker such as triglycidylisocyanurate (TGIC) commercially available as Aradite PT-810 by Ciba Geigy or alternatively an activated B-hydroxylalkyl amide such as Bis(N,N-dihydroxyethyl)adipamide commercially available from EMS as PRIMID XL552 or PRIMID QM1260, or epoxy resins that are based on bisphenol A and (c) optionally, additives such as benzoin, flow aids , pigments and catalyst. Additives commonly used ar$ benzoin for reducing entrapped air or volatiles, flow aid such as Modaflow III, catalyst such as dibutyltin dilaurate and pigments such as titanium dioxide or stabilizer such as UV absorber (UVA) and hindered amine light stabilizer (HALS). This invention can be further illustrated by the following examples of preferred embodiments thereof, although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention unless otherwise specifically indicated.
EXAMPLES The inherent viscosity (IN.), in dl/g is determined in phenol/tetrachloroethane ( 60/40 w/w ) at a concentration of 0.5g/100 ml. The resin melt viscosity, in poise, is determined using an ICI melt viscometer at 200° C.
The acid number and hydroxyl number are determined by titration and reported as miligram (mg ) of KOH consumed for each gram of resin.
The glass transition temperature (Tg), is determined by differential scanning calorimetry (DSC) on the second heating cycle with a scanning rate of 20° C / minute after the sample has been heated to melt and quenched to below the resin Tg. Tg values are reported as midpoint. The weight average molecular weight (Mw) and number average molecular weight (Mn) are determined by gel permeation chromatography in tetrahydrofuran (THF) using polystyrene standard and a UV detector.
Impact strengths are determined using a Gardner Laboratory, Inc., impact tester per ASTM D 2794-84. Pencil hardness is determined using ASTM D 3363-74. The hardness is reported as the hardest pencil which will not cut into the coating. The resultsare expressed according to the following scale:
(softest)6B,5B,4B,3B,2B,B,HB,F,H,2H,3H,4H,5H,6H(hardest) The conical mandrel is performed using a Gardener Laboratory Inc., conical mandrel of specified size according to ASTM-522. The 20 and 60 degree gloss are measured using a gloss meter (Gardener Laboratory, Inc. Model GC-9095) according to ASTM D-523. Resin Examples 1 , 2 and 3 Resin preparation for hydroxyl resins. To a 2-liter reactor equipped with mechanical stirrer, heated packed column, distillation condenser, thermocouples, nitrogen stream and accessories needed for computer and Camile control are charged reactants, catalyst and excess glycol. The content is heated gradually to melt the glycols to result in a slurry mix. The mix is stirred as it becomes possible. The reaction is maintained with a nitrogen stream and stirrer speed at 300 rpm and the cook schedule maintained by a heat control with computer control (Camile) as follows:
25° C - 180° C over 1.3 hours
180° C - 235° C over 6 hours 235° C hold for 5 hours
Water from the reaction is removed through a heated column and distillation condenser until an acid number of less than 5 is reached.
Table I. Resin Examples 1 , 2 and 3
Resin example 1 2 3
Purified terephthalic acid (PTA) 817.85 812.82 807.53
Neopentyl Glycol ( NPG)* 523.86 465.83 408.57 2-Methyl-1 ,3-pentanediol( EMPD) 0 62.18 123.66
Trimethylolpropane (TMP) 35.51 35.29 35.09 Fascat 4100 catalyst 1.2 1.2 1.2
Resin properties
Mole % replacement of NPG 0 10 20
Glycol
Acid number (mg KOH/g resin) 4 6 5
Hydroxyl number(mg KOH/g 35 36 40 resin)
ICI viscosity at 200°C (poise) 59 60 32
Intrinsic viscosity 0.204 0.221 0.19
Mw 13333 13401 10683
Mn 3584 3562 3178
Glass transition temperature( Tg) , 64/61 63/60 58/54 midpoint/onset (°C)
Diols Ratio NPG/EMPD/TMP 95/0/5 85/10/5 75/20/5
*A 1 % excess of NPG is used in addition to the charge shown above to allow for losses to the distillate.
Powder Coating Examples 4. 5, 6
Resin, crosslinker and additives are mixed in a Henschel mixer and compounded in a ZSK 30 extruder with temperature profile and screw speed as specified. The extrudate is cooled through a chili roll, granulated and pulverized using a Bantam mill with liquid nitrogen bled into the grinding chamber. The powder is classified through a 200 mesh screen. The powder is electrostatically applied to 3 in. x 9 in. metal panels and cured in oven as specified temperature and time. Table 2: Powder Coating Formulation
Powder examples 4 5 6
Comparative Resin from example 1 (control) 560
Resin from example 2 ( with 10% — 560
EMPD)
Resin from example 3 ( with 20% — — 560
EMPD)
Huls B1530 140 140 140
Dibutyltin dilaurate, 60% active 11.7 11.7 11.7 powder
Modaflow 2000 10.5 10.5 10.5
Benzoin 7 7 7
TiO2, R-960 350 350 350
Total Weight 1079.2 1079.2 1079.2
ZSK 30 conditions Zone 1 100 100 100 Zone 2 110 110 110 Feed Rate 200 200 200 Screw rpm 300 300 300
Table 3: Physical Properties of Powder Coating Enamels
:>owder example 4 5 6
Cure temperature 350° 375°F 350°F 375°F 350°F 375° (20 min. bake) F
Thickness, mil 1.9 1.9 1.9 1.9 1.9 1.9
20° gloss 45 44 68 65 75 74 60° gloss 77 76 90 88 89 89
Impact resistance, 90/18 258/54 114/90 258/150 210/78 258/114 front/reverse, in-lb
Pencil Hardness (cut) 3H 3H 3H 3H 3H 4H (Mar) F F F H H H
1/8" Conical Mandrel Pass Pass Pass Pass Pass Pass
MEK double rubs 200+ 200+ 200+ 200+ 200+ 200+
Orange Peel ( Visual 5 5 6 6 7 7 Standard, scale of 1-10 with 10 being smoothest)
Incline plate flow @ 200° C , 97 88 116 mm
Gel time @ 204° C, in seconds 76 82 94
Caking stability @ 40° C for 3 99.3 99.1 98.7 days, % pass
The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.

Claims

CLAIMSWhat is Claimed Is:
1. A polyester resin comprising 1-ethyl-2-methyl-1 ,3-propanediol and neopentyl glycol reacted with compounds selected from the group consisting of diols and diacids.
2. A powder coating composition comprising the resin of claim 1 and a crosslinker.
PCT/US1998/027285 1998-12-22 1998-12-22 Powder coating compositions based on empd polyester resins WO1999030903A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027285 WO1999030903A1 (en) 1998-12-22 1998-12-22 Powder coating compositions based on empd polyester resins

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Application Number Priority Date Filing Date Title
PCT/US1998/027285 WO1999030903A1 (en) 1998-12-22 1998-12-22 Powder coating compositions based on empd polyester resins

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Publication Number Publication Date
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010026066A1 (en) * 2008-09-04 2010-03-11 Basf Se Use of substituted 2-aryl-2-alkyl-1,3-propanediols or substituted 2-cyclohexyl-2-alkyl-1,3-propanediols for manufacturing polymers

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5442023A (en) * 1994-06-30 1995-08-15 Union Carbide Chemicals & Plastics Technology Corporation Hindered-hydroxyl functional (meth)acrylate monomers containing di(meth)acrylates and compositions including same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5442023A (en) * 1994-06-30 1995-08-15 Union Carbide Chemicals & Plastics Technology Corporation Hindered-hydroxyl functional (meth)acrylate monomers containing di(meth)acrylates and compositions including same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010026066A1 (en) * 2008-09-04 2010-03-11 Basf Se Use of substituted 2-aryl-2-alkyl-1,3-propanediols or substituted 2-cyclohexyl-2-alkyl-1,3-propanediols for manufacturing polymers

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