Improved radiation-hardenable diluents

Claim 2

Lower alkyl ether acrylates having the following structures: where: R = -H₂C HCH₂-, C₅ or C₆ R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H-, CH₃- or mixtures a = 1, 2 or 3 m = 0 to about 6 n = 0 to about 6 with the proviso m + n does not exceed about 6, and with the proviso when C₅ is linear, m + n is about 1 to about 6 mono-lower alkoxy trans-1,4-cyclohexane dimethylol monoacrylate, mono-lower alkoxy trans-1,4-cyclohexane dimethylol monomethacrylate, mono-lower alkoxy 2,2,4-trimethyl-1,3-pentanediol monoacrylate, mono-lower alkoxy 2,2,4-trimethyl -1,3-pentanediol monomethacrylate and where: R' = at least one of C₁ to C₆ R'' = H- or CH₃-, CH₃CH₂- or mixtures R''' = H-, CH₃- R'''' = H-, CH₃- or mixtures a = 1 m = 0 to about 6 n = 0 to about 6 m + n = 0 to about 6.

Claim 3

Lower alkyl ether acrylates of claim 1 selected from the group consisting of: mono-methoxy trimethylolpropane diacrylate mono-methoxy, ethoxylated trimethylolpropane diacrylate having an average of about three moles of ethylene oxide mono-methoxy, propoxylated trimethylolpropane diacrylate having an average of about three moles of propylene oxide mono-methoxy 1,6-hexanediol monoacrylate mono-methoxy pentaerythritol triacrylate mono-methoxy, propoxylated pentaerythritol triacrylate having an average of about four moles of propylene oxide mono-methoxy neopentyl glycol monoacrylate mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide mono-methoxy, propoxylated neopentyl glycol monoacrylate having an average of about two moles of propylene oxide mono-methoxy trans-1,4-cyclohexane dimethylol monoacrylate mono-methoxy propoxylated glycerol diacrylate having an average of about three moles of propylene oxide mono-methoxy propoxylated hexane glycol monoacrylate having an average of about two moles of propyleneoxide mono-methoxy 2,2,4-trimethyl 1,3-pentanediol monoacrylate mono-methoxy ethoxylated 2,2-bis(p-hydroxyphenyl)propane monoacrylate having an average of about four moles of ethylene oxide mono-methoxy bis(p-hydroxyphenyl)methane monoacrylate mono-methoxy trimethylolpropane dimethacrylate mono-methoxy, ethoxylated trimethylol propane dimethacrylate having an average of three moles of ethylene oxide mono-methoxy, propoxylated trimethylol propane dimethacrylate having an average of three moles of propylene oxide mono-methoxy 1,6-hexanediol monomethacrylate mono-methoxy pentaerythritol trimethacrylate mono-methoxy, propoxylated pentaerythritol trimethacrylate having an average of four moles of propylene oxide mono-methoxy neopentyl glycol monomethacrylate mono-methoxy, ethoxylated neopentyl glycol monomethacrylate having an average of two moles of ethylene oxide mono-methoxy, propoxylated neopentyl glycol monomethacrylate having an average of two moles of propylene oxide mono-methoxy trans-1,4-cyclohexane dimethylol monomethacrylate mono-methoxy propoxylated glycerol dimethacrylate having an average of three moles of propylene oxide mono-methoxy propoxylated hexane glycol monomethacrylate having an average of two moles of propylene oxide mono-methoxy 2,2,4-trimethyl 1,3-pentane diol monomethacrylate mono-methoxy ethoxylated 2,2-bis(p-hydroxyphenyl)propane monomethacrylate having an average of four moles of ethylene oxide mono-methoxy bis(p-hydroxyphenyl)methane monomethacrylate

Claim 4

A lower alkyl ether acrylate of claim 2 which is mono-methoxy neopentyl glycol monoacrylate.

Claim 5

A lower alkyl ether acrylate of claim 2 which is mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide.

Claim 6

A lower alkyl ether acrylate of claim 2 which is mono-methoxy, propoxylated neopentyl glycol monoacrylate having an average of about two moles of propylene oxide.

Claim 7

A lower alkyl ether acrylate of claim 2 which is mono-methoxy trimethylolpropane diacrylate.

Claim 8

A lower alkyl ether acrylate of claim 2 which is mono-methoxy, ethoxylated trimethylolpropane diacrylate having an average of about three moles of ethylene oxide.

Claim 9

A lower alkyl ether acrylate of claim 2 which is mono-methoxy propoxylated trimethylolpropane diacrylate having an average of about three moles of propylene oxide.

Claim 10

A lower alkyl ether acrylate of claim 2 which is mono-methoxy 1,6-hexanediol monoacrylate.

Claim 11

A lower alkyl ether acrylate of claim 2 which is mono-methoxy trans-1,4-cyclohexane dimethylol monoacrylate.

Claim 12

A lower alkyl ether acrylate of claim 2 which is mono-methoxy 2,2,4-trimethyl 1,3-pentanediol monoacrylate.

Claim 13

A lower alkyl ether acrylate of claim 2 which is mono-methoxy ethoxylated 2,2-bis(p-hydroxyphenyl) propane monoacrylate having an average of about four moles of ethylene oxide.

Claim 14

A lower alkyl ether acrylate of claim 2 which is mono-methoxy propoxylated glycerol diacrylate having an average of about three moles of propylene oxide.

Claim 15

A radiation hardenable composition comprising at least one radiation hardenable oligomer and at least one radiation hardenable diluent selected from the group consisting of: where: R = C₂ to C₆ R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H-, CH₃ or mixtures a = 1, 2 or 3 m = 0 to about 6 n = 0 to about 6 and with the proviso m + n does not exceed about 6 mono-lower alkoxy trans-1,4-cyclohexane dimethylol monoacrylate, mono-lower alkoxy trans-1,4-cyclohexane dimethylol monomethacrylate, mono-lower alkoxy 2,2,4-trimethyl-1,3-pentanediol monoacrylate, mono-lower alkoxy 2,2,4-trimethyl-1,3-pentanediol monomethacrylate and where: R' = at least one C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H- or CH₃- R'''' = H-, CH₃ or mixtures a = 1 m = 0 to about 6 n = 0 to about 6 m + n = 0 to about 6

Claim 16

A radiation hardenable composition comprising at least one radiation hardenable oligomer and at least one radiation hardenable diluent selected from the group consisting of: where: R = C₂ to C₆ R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H-, CH₃ or mixtures a = 1, 2 or 3 m = 0 to about 6 n = 0 to about 6 and with the proviso m + n does not exceed about 6 mono-lower alkoxy trans-1,4-cyclohexane dimethylol monoacrylate, mono-lower alkoxy trans-1,4-cyclohexane dimethylol monomethacrylate, mono-lower alkoxy 2,2,4-trimethyl-1,3-pentanediol monoacrylate, mono-lower alkoxy 2,2,4-trimethyl-1,3-pentanediol monomethacrylate and where: R' = at least one C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H- or CH₃- R'''' = H-, CH₃ or mixtures a = 1 m = 0 to about 6 n = 0 to about 6 m + n = 0 to about 6

Claim 17

The composition of claim 14 wherein said diluent is present in an amount of from about 5% to about 80% by weight of the composition.

Claim 18

The composition of claim 14 wherein said diluent is selected from the group consisting of: mono-methoxy trimethylolpropane diacrylate mono-methoxy, ethoxylated trimethylolpropane diacrylate having an average of about three moles of ethylene oxide mono-methoxy, propoxylated trimethylolpropane diacrylate having an average of about three moles of propylene oxide mono-methoxy 1,6-hexanediol monoacrylate mono-methoxy pentaerythritol triacrylate mono-methoxy, propoxylated pentaerythritol triacrylate having an average of about four moles of propylene oxide mono-methoxy tripropylene glycol monoacrylate mono-methoxy neopentyl glycol monoacrylate mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide mono-methoxy, propoxylated neopentyl glycol monoacrylate having an average of about two moles of propylene oxide mono n-butoxy diethylene glycol monoacrylate mono ethoxy diethylene glycol monoacrylate mono-methoxy trans-1,4-cyclohexane dimethylol monoacrylate mono-methoxy diethylene glycol monoacrylate mono-n-butoxy ethylene glycol monoacrylate mono-methoxy triethylene glycol monoacrylate mono-methoxy propylene glycol monoacrylate mono-methoxy propoxylated glycerol diacrylate having an average of about three moles of propylene oxide mono-methoxy propoxylated hexane glycerol monoacrylate having an average of about two moles of propylene oxide mono-methoxy 2,2,4-trimethyl 1,3-pentanediol monoacrylate mono-propoxy ethylene glycol monoacrylate mono-methoxy ethoxylated 2,2-bis(p-hydroxyphenyl)propane monoacrylate having an average of four moles of ethylene oxide and mono-methoxy bis(p-hydroxyphenyl)methane monoacrylate. mono-methoxy trimethylolpropane dimethacrylate mono-methoxy, ethoxylated trimethylol propane dimethacrylate having an average of three moles of ethylene oxide mono-methoxy, propoxylated trimethylol propane dimethacrylate having an average of three moles of propylene oxide mono-methoxy 1,6-hexanediol monomethacrylate mono-methoxy pentaerythritol trimethacrylate mono-methoxy, propoxylated pentaerythritol trimethacrylate having an average of four moles of propylene oxide mono-methoxy neopentyl glycol monomethacrylate mono-methoxy, ethoxylated neopentyl glycol monomethacrylate having an average of two moles of ethylene oxide mono-methoxy, propoxylated neopentyl glycol monomethacrylate having an average of two moles of propylene oxide mono-methoxy trans-1,4-cyclohexane dimethylol monomethacrylate mono-methoxy propoxylated glycerol dimethacrylate having an average of three moles of propylene oxide mono-methoxy propoxylated hexane glycol monomethacrylate having an average of two moles of propylene oxide mono-methoxy 2,2,4-trimethyl 1,3-pentane diol monomethacrylate mono-methoxy ethoxylated 2,2-bis(p-hydroxyphenyl)propane monomethacrylate having an average of four moles of ethylene oxide mono-methoxy bis(p-hydroxyphenyl)methane monomethacrylate

Claim 19

The composition of claim 16 wherein said diluent is mono-methoxy neopentyl glycol monoacrylate.

Claim 20

The composition of claim 16 wherein said diluent is mono-methoxy, ethoxylated neopentyl glycol monoacrylate having an average of about two moles of ethylene oxide.

Claim 21

The composition of claim 16 wherein said diluent is mono-methoxy, propoxylated neopentyl glycol monoacrylate having an average of about two moles of propylene oxide.

Claim 22

The composition of claim 16 wherein said diluent is mono-methoxy trimethylolpropane diacrylate.

Claim 23

The composition of claim 16 wherein said diluent is mono-methoxy, ethoxylated trimethylolpropane diacrylate having an average of about three moles of ethylene oxide.

Claim 24

The composition of claim 16 wherein said diluent is mono-methoxy propoxylated trimethylolpropane diacrylate having an average of about three moles of propylene oxide.

Claim 25

The composition of claim 16 wherein said diluent is mono-methoxy 1,6-hexanediol monoacrylate.

Claim 26

The composition of claim 16 wherein said diluent is mono-methoxy trans-1,4-cyclohexane dimethylol monoacrylate.

Claim 27

The composition of claim 16 wherein said diluent is mono-methoxy 2,2,4-trimethyl 1,3-pentanediol monoacrylate.

Claim 28

The composition of claim 16 wherein said diluent is mono-methoxy ethoxylated 2,2-bis(p-hydroxy­ phenyl)propane monoacrylate having an average of about four moles of ethylene oxide.

Claim 29

The composition of claim 16 wherein said diluent is mono-ethoxy propoxylated glycerol diacrylate having an average of about three moles of propylene oxide.

Claim 30

The radiation cured reaction products of claim 14.

Claim 31

The radiation cured reaction products of claim 15.

Claim 32

The radiation cured reaction products of claim 16.

Claim 33

Lower alkyl ethers having the following structures: where: R = -H₂C HCH₂-, C₅ or C₆ R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures a = 1 to 3 m = 0 to about 6 n = 0 to about 6 and when m + n = 0, a = 1 with the proviso m + n does not exceed about 6 and with the proviso when C₅ is linear, m + n is about 1 to about 6 mono-lower alkoxy trans-1,4-cyclohexane dimethylol, mono-­lower alkoxy 2,2,4-trimethyl-1,3-pentanediol and where: R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H- or CH₃- a = 1 m = 0 to about 6 n = 0 to about 6 with the proviso m + n = 0 to about 6.

Claim 34

Lower alkyl ethers having the following structures: where: R = -H₂C HCH₂-, C₅ or C₆ R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures a = 1 to 3 m = 0 to about 6 n = 0 to about 6 and when m + n = 0, a = 1 with the proviso m + n does not exceed about 6 and with the proviso when C₅ is linear, m + n is about 1 to about 6 mono-lower alkoxy trans-1,4-cyclohexane dimethylol, mono-­lower alkoxy 2,2,4-trimethyl-1,3-pentanediol and where: R' = at least one of C₁ to C₆ R'' = H-, CH₃-, CH₃CH₂- or mixtures R''' = H- or CH₃- a = 1 m = 0 to about 6 n = 0 to about 6 with the proviso m + n = 0 to about 6.

Claim 35

Lower alkyl ethers of claim 31 selected from the group consisting of: mono-methyl ether of propoxylated pentaerythritol having an average of about four moles of propylene oxide mono-methyl ether of ethoxylated trimethylolpropane having an average of about three moles of ethylene oxide mono-methyl ether of propoxylated trimethylolpropane having an average of about three moles of propylene oxide mono-methyl ether of 1,6-hexanediol mono-methyl ether of neopentyl glycol mono-methyl ether of ethoxylated neopentyl glycol having an average of about two moles of ethylene oxide mono-methyl ether of propoxylated neopentyl glycol having an average of about two moles of propylene oxide mono-methyl ether of propoxylated glycerol having an average of about three moles of propylene oxide mono-methyl ether of trans-1,4-cyclohexane dimethylol mono-methyl ether of 2,2-bis(p-hydroxyphenyl)propane having an average of about four moles of ethylene oxide and mono-methyl ether of bis-(p-hydroxyphenyl)methane mono-methyl ether of 2,2,4-trimethyl-1,3 pentanediol mono-methyl ether of propoxylated hexylene glycol having an average of about two moles of propylene oxide.

Claim 36

A lower alkyl ether of claim 32 which is mono-methyl ether of neopentyl glycol.

Claim 37

A lower alkyl ether of claim 32 which is mono-methyl ether of ethoxylated neopentyl glycol having an average of about two moles of ethylene oxide.

Claim 38

A lower alkyl ether of claim 32 which is mono-methyl ether of propoxylated neopentyl glycol having an average of about two moles of ethylene oxide.

Claim 39

A lower alkyl ether of claim 32 which is mono-methyl ether of trans-1,4-cyclohexane dimethylol.

Claim 40

A lower alkyl ether of claim 32 which is mono-methyl ether of 2,2,4-trimethyl 1,3-pentanediol.

Claim 41

A lower alkyl ether of claim 32 which is mono-methoxy ethoxylated 2,2-bis(p-hydroxyphenyl)propane having an average of about four moles of ethylene oxide.

Claim 42

A lower alkyl ether of claim 32 which is mono-methoxy propoxylated glycerol having an average of about three moles of propylene oxide.