IP Library Granted Patent US 7,034,086
Granted Patent B2
US 7,034,086 · App. 10/403,442 · Granted Apr 25, 2006

Melamine and guanamine-based crosslinking composition

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Quick Facts
Patent No.
US 7,034,086
App. No.
10/403,442
Granted
Apr 25, 2006
Kind
B2
Abstract

This invention relates to a crosslinking composition comprising a compound having the structure of Formula I: where Z is a hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of about 6 to about 24 carbon atoms, an aralkyl of about 7 to about 24 carbon atoms, or —NR 2 R 2 ; each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 18 carbon atoms or R 3 ; where R 3 is —CHROR 1 or where R is alkyl, halogenated alkyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; R 1 is a hydrogen, alkyl, aryl, aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; and where the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure; B is a residue of a poly(alkylaldehyde) with n aldehyde groups; n is an integer of 2 to about 4; and A is an amino moiety derived from the group consisting of guanamine and melamine. The above composition may be prepared by reacting a melamine or guanamine with a mono(alkylaldehyde), a poly(alkylaldehyde) and an alcohol.

Claims (51)

1. A crosslinking composition comprising a compound having the structure of Formula I:

wherein Z is a hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of about 6 to about 24 carbon atoms, an aralkyl of about 7 to about 24 carbon atoms, or —NR 2 R 2 ;

each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 18 carbon atoms or R 3 ;

wherein R 3 is —CHROR 1 , or

wherein R is alkyl, halogenated alkyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl, having from 1 to about 24 carbon atoms; R 1 is a hydrogen, alkyl, aryl, aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; and wherein the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure;

B is a residue of a poly(alkylaldehyde) with n aldehyde groups;

n is an integer of 2 to about 8;

A is an amino moiety derived from the group consisting of guanamines and melamines.

2. The composition of claim 1 , wherein said compound having the Formula I is an oligomer having an number average molecular weight of from about 500 to about 5000.

3. A crosslinking composition comprising a compound having the structure of Formula II:

wherein Z is a hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of 6 to about 24 carbon atoms, an aralkyl of 7 to about 24 carbon atoms, or —NHR 2 ;

each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 18 carbon atoms or R 3 ;

wherein R 3 is —CHROR 1 , or

wherein R is alkyl, halogenated alkyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; R 1 is a hydrogen, alkyl, aryl, aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; and wherein the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure;

B is a residue of a poly(alkylaldehyde) with n aldehyde groups;

n is an integer of 2 to about 8;

A is an amino moiety derived from the group consisting of guanamines and melamines.

4. The composition of claim 3 , wherein said compound having the Formula II is in the form of an oligomer having an number average molecular weight of from about 500 to about 5000.

5. The crosslinking composition of claim 3 , wherein R 1 is derived from an alcohol selected from the group consisting of: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, cyclohexanol, phenol, benzyl alcohol, monoalkyl ether of ethylene or propylene glycol and mixtures thereof.

6. The crosslinking composition of claim 3 , wherein Z is —NHR 2 , an alkyl of 1 to about 8 carbon atoms or an aryl of 6 to about 24 carbon atoms.

7. The crosslinking composition of claim 3 , wherein B is derived from glutaraldehyde, the reaction products of crotonaldehyde and polyhydritic alcohols or adducts and polymers of α,β-unsaturated aldehydes.

8. The crosslinking composition of claim 6 , wherein R is C 1 to C 8 alkyl and R 1 is a C 1 to C 8 alkyl or a C 1 to C 8 alkoxyalkyl.

9. The crosslinking composition of claim 1 , wherein about 10% to about 90% of the R 2 groups on a molar basis are —CHROR 1 .

10. The crosslinking composition of claim 3 , wherein R 1 is derived from methanol, butanol, monomethyl ether of ethylene glycol or monomethyl ether of propylene glycol.

11. A crosslinking composition comprising a compound having the structure of Formula III:

wherein Z is a hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of 6 to about 24 carbon atoms, an aralkyl of 7 to about 24 carbon atoms, or —NR 2 R 2 ;

each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 24 carbon atoms or R 3 ;

R 3 is —CHROR 1 ; wherein R 1 is hydrogen, alkyl, aryl, aralkyl, or an alkaryl having from 1 to about 24 carbon atoms; and R is ethyl, or an aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms;

wherein the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure and with the provisos that at least some R 1 groups are derived from a mixture of two or more alcohols and at least one R 2 is R 3 .

12. A crosslinking composition comprising the structure of formula:

wherein Z is a hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of 6 to about 24 carbon atoms, an aralkyl of 7 to about 24 carbon atoms, or —NHR 2 ;

each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 24 carbon atoms or R 3 ;

R 3 is —CHROR 1 ; wherein R 1 is hydrogen, alkyl, aryl, aralkyl or an alkaryl having from 1 to about 24 carbon atoms; and R is ethyl, or an aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms;

wherein the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure and with the provisos that at least some R 1 groups are derived from a mixture of two or more alcohols and at least one R 2 is R 3 .

13. The crosslinking composition of claim 12 , wherein R is ethyl.

14. The crosslinking composition of claim 13 , wherein R 1 is derived from two or more alcohols selected from the group consisting of: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, cyclohexanol, phenol, benzyl alcohol, monoalkyl ether of ethylene or propylene glycol and mixtures thereof.

15. The crosslinking composition of claim 13 , wherein about 10% to about 90% of the R 2 groups on a molar basis are R 3.

16. The crosslinking composition of claim 13 , wherein Z is -NHR 2 , an alkyl of 1 to 8 carbon atoms or an aryl of 6 to 24 carbon atoms.

17. The crosslinking composition of claim 16 , wherein R 1 is a C 1 to C 8 alkyl or a C 1 to C 8 alkoxyalkyl.

18. A crosslinking composition comprising an oligomer compound having the Formula IV:

wherein Z is hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of 6 to about 24 carbon atoms, an aralkyl of 7 to about 20 carbon atoms, or −NR 2 R 2 ;

each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 24 carbon atoms or R 3;

R 3 is −CHROR 1 ; wherein R 1 is hydrogen, an alkyl, aryl, aralkyl, or an alkaryl having from 1 to about 24 carbon atoms and R is ethyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to 24 carbon atoms;

n is 2 to about 50;

wherein the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure and with the provisos that at least some R groups are derived from a mixture of two or more alcohols and at least one R 2 is R 3 .

19. A crosslinking composition comprising an oligomer compound having the Formula V:

wherein Z is a hydrogen, an alkyl of 1 to about 18 carbon atoms, an aryl of 6 to about 24 carbon atoms, an aralkyl of 7 to about 24 carbon atoms, or —NR 2 R 2 ;

each R 2 is independently hydrogen, an alkyl, aryl or an aralkyl of 1 to about 18 carbon atoms or R 3 ;

R 3 is —CHROR 1 ; wherein R 1 is hydrogen, an alkyl, aryl, aralkyl, or an alkaryl, having from 1 to about 24 carbon atoms and R is ethyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl, having from 1 to about 24 carbon atoms;

n is 2 to about 50;

wherein the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure and with the provisos that at least some R 1 groups are derived from a mixture of two or more alcohols and at least one R 2 is R 3 .

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2018
From: ALLNEX HOLDING INTERNATIONAL B.V.
To: ALLNEX NETHERLANDS B.V.
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MERGER Recorded Apr 26, 2018
From: ALLNEX IP S.A.R.L.
To: ALLNEX HOLDING INTERNATIONAL B.V.
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TERMINATION AND RELEASE OF FIRST LIEN SECURITY INTEREST IN PATENTS RECORDED AT REEL 030147 FRAME 0492 Recorded Sep 16, 2016
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: AL CHEM & CY US ACQUICO, INC.
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TERMINATION AND RELEASE OF SECOND LIEN SECURITY INTEREST IN PATENTS RECORDED AT REEL 030147 FRAME 0511 Recorded Sep 16, 2016
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: AL CHEM & CY US ACQUICO, INC.
Reel/Frame 040059/0119 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2015
From: ALLNEX USA INC.
To: ALLNEX IP S.À.R.L.
Reel/Frame 036852/0610 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2014
From: CYTEC TECHNOLOGY CORP.
To: AI CHEM & CY US ACQUICO, INC.
Reel/Frame 032502/0332 →
CHANGE OF NAME Recorded Mar 22, 2014
From: AI CHEM & CY US ACQUICO, INC.
To: ALLNEX USA INC.
Reel/Frame 032503/0265 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: AI CHEM & CY US ACQUICO, INC.
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 030147/0492 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: AI CHEM & CY US ACQUICO, INC.
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 030147/0511 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2003
From: LIN, LON-TANG WILSON; JACOBS III, WILLIAM; VERHAGE, DIMITRI; WU, KUANG-JONG
To: CYTEC TECHNOLOGY CORP.
Reel/Frame 014501/0138 →